Organotin compound, method for preparing same, and method for forming thin film using same

Abstract

The present invention relates to a novel organotin compound, a method for preparing same, and a method for producing a tin-containing thin film using same. The organotin compound according to the present invention exhibits good thermal stability, high volatility, and vapor pressure, and thus is very useful as a precursor for a tin-containing thin film. Furthermore, the compound exists in a liquid state at room temperature and atmospheric pressure, which facilitates handling. Therefore, a high-quality tin-containing thin film can be manufactured using the thin-film deposition composition comprising the organotin compound according to the present invention. In addition, the organotin compound according to the present invention has high extreme ultraviolet (EUV) sensitivity, and thus a photoresist composition comprising same can form a photoresist pattern with excellent resolution and sensitivity.

Description

Organotin compound, method for preparing the same, and method for forming a thin film using the same

[0001] The present invention relates to a novel organotin compound, a method for producing the same, and a method for producing a tin-containing thin film using the same.

[0002] Recently, as the semiconductor industry progresses in miniaturization of devices, various metal atoms can be used as materials for thin film semiconductors. However, indium (In) and gallium (Ga) are expensive due to limited reserves, and cadmium (Cd) has disadvantages such as being toxic.

[0003] Photolithography, a semiconductor manufacturing process, is the process of creating precise circuit patterns on semiconductors. Photoresist, a type of photosensitive liquid that reacts with light to undergo chemical changes, is applied to the substrate. This, along with the exposure light source, determines the degree of detail achieved through photolithography. Research is actively underway to utilize extreme ultraviolet (EUV) light as the exposure light source. Due to the short wavelength and high energy of EUV, EUV lithography is more advantageous than other photolithography processes in producing finer patterns.

[0004] In the development of high-sensitivity EUV photoresists, the development of materials with excellent photosensitivity to extreme ultraviolet rays is important. Among metallic elements, elements with d orbitals have high EUV absorbance, and precursors containing these elements can have high absorbance, making them suitable as materials for manufacturing high-performance EUV photoresist materials.

[0005] Tin oxide is attracting attention as a substitute for the aforementioned thin film semiconductor materials because it is transparent, maintains high conductivity, and EUV absorbance. Chemical vapor deposition (CVD) or atomic layer deposition (ALD) are mainly used as processes for forming thin films. When forming thin films using the above processes, differences in the structure, deposition degree, deposition control characteristics, purity, etc. of the thin film can occur depending on the characteristics of the metal precursor. Therefore, the development of a tin oxide precursor with excellent characteristics is essential.

[0006] The present invention aims to provide a novel organotin compound.

[0007] Specifically, one object of the present invention is to provide an organotin compound having thermal stability, high volatility and vapor pressure useful as a tin-containing thin film precursor.

[0008] In addition, the present invention aims to provide a method for producing a high-quality tin-containing thin film using the above-mentioned organotin compound.

[0009] In addition, the present invention aims to provide a photoresist composition for extreme ultraviolet (EUV) comprising the above organotin compound.

[0010] In addition, the present invention aims to provide a method for producing the above organotin compound.

[0011] The organotin compound according to the present invention is represented by the following chemical formula 1.

[0012] [Chemical Formula 1]

[0013]

[0014] (In the above chemical formula 1,

[0015] R 1 and R 2 are independently straight or branched (C1-C10) alkyl;

[0016] R 3 Inland R 5are independently straight or branched chain (C1-C10)alkyl, (C6-C12)aryl or (C1-C10)alkyl(C6-C12)aryl.

[0017] More preferably, R of the above chemical formula 1 1 and R 2 are independently straight or branched (C1-C5) alkyl, and R 3 Inland R 5 can be independently a straight or branched chain (C1-C5)alkyl, (C6-C8)aryl or (C1-C5)alkyl(C6-C8)aryl.

[0018] More preferably, the above R 3 Inland R 5 may be a straight chain (C1-C3) alkyl, more preferably R 3 Inland R 5 can be methyl.

[0019] In addition, the present invention provides a method for producing an organotin compound of the following chemical formula 1 by reacting a halogenated tin compound of the following chemical formula 2 with an alkoxyalkylamide metal salt compound of the following chemical formula 3.

[0020] [Chemical Formula 1]

[0021]

[0022] [Chemical Formula 2]

[0023]

[0024] [Chemical Formula 3]

[0025]

[0026] (In the above chemical formulas 1 to 3,

[0027] R 1 and R 2 are independently straight or branched (C1-C10) alkyl;

[0028] R 3 Inland R 5are independently straight-chain or branched (C1-C10)alkyl, (C6-C12)aryl or (C1-C10)alkyl(C6-C12)aryl;

[0029] X is a halogen;

[0030] M is Li, Na or K.)

[0031] More preferably, the above R 1 Inland R 5 are independently straight or branched (C1-C5) alkyl,

[0032] X can be Cl and M can be Na.

[0033] In addition, the present invention provides a composition for thin film deposition comprising the above-described organotin compound.

[0034] In addition, the present invention provides a method for manufacturing a tin-containing thin film using the above-described thin film deposition composition.

[0035] The organotin compound of the present invention has a novel structure including an alkoxyalkylamide ligand, and is very useful as a precursor for tin-containing thin films due to its excellent thermal stability and high volatility and vapor pressure. Furthermore, it exists in a liquid state at room temperature and pressure, making it easy to handle. Therefore, a high-quality tin-containing thin film can be produced using a thin film deposition composition including the organotin compound according to the present invention.

[0036] In addition, the organotin compound according to the present invention has high extreme ultraviolet (EUV) sensitivity, so that a photoresist composition including the organotin compound can form a photoresist pattern with excellent resolution and sensitivity.

[0037] In addition, the method for producing an organotin compound according to the present invention can produce an organotin compound in good yield through a relatively simple process.

[0038] Figure 1 is a thermogravimetric analysis result spectrum of the organotin compounds prepared in Examples 1 to 4.

[0039] Hereinafter, the present invention will be described in more detail. Unless otherwise defined, the technical and scientific terms used herein have the meanings commonly understood by those of ordinary skill in the art to which this invention pertains. In the following description, descriptions of well-known functions and configurations that may unnecessarily obscure the gist of the present invention will be omitted.

[0040] The term “comprises” in this specification is an open-ended description equivalent to “comprises,” “contains,” “has,” or “characterizes,” and does not exclude additional elements, materials, or processes not listed herein.

[0041] As used herein, the singular forms may be intended to include the plural forms as well, unless the context clearly indicates otherwise.

[0042] The term “organotin compound” in this specification can be represented by Chemical Formula 1 and has a meaning equivalent to expressions such as “tin-containing thin film precursor”.

[0043] Additionally, the term “thermal stability” in this specification may mean that the physical properties do not change even during a continuous heating process or a high temperature process, and specifically means that the structural changes do not occur even when exposed for a long period of time under the harsh conditions described above.

[0044] The term “alkyl” as used herein means a monovalent straight-chain or branched saturated hydrocarbon atom group composed solely of carbon and hydrogen atoms, examples of which include, but are not limited to, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, pentyl, hexyl, and the like.

[0045] The term “aryl” as used herein refers to a functional group derived from an aromatic hydrocarbon by the removal of one hydrogen, and representative examples include, but are not limited to, phenyl, tolyl, xylyl, naphthyl, tetrahydronaphthyl, anthracenyl, fluorenyl, indenyl, azulenyl, and the like. The term “alkylaryl” as used herein refers to an alkyl group as defined above directly bonded to an aryl group as defined above, and includes, but is not limited to, -C6H4CH3 and -C6H4C2H5.

[0046] The term “halo” or “halogen” as used herein means fluorine, chlorine, bromine or iodine.

[0047] In this specification, “room temperature” means a temperature of 20±5℃.

[0048] In this specification, “Ph” means a phenyl group (-C6C5).

[0049] The term "CA-CB" in this specification means "having carbon atoms greater than or equal to A and less than or equal to B."

[0050] The term “edpa” in this specification is an abbreviation for N-ethoxy-2,2-dimethylpropanamide.

[0051] The term “” in this specification is an abbreviation for N-methoxy-2,2-dimethylpropanamide.

[0052] The term “empa” in this specification is an abbreviation for N-ethoxy-2-methylpropanamide.

[0053] The term “mpa” in this specification is an abbreviation for N-methoxy-propanamide.

[0054] The term “btsa” in this specification is an abbreviation for bistrimethylsilylamide.

[0055] The present invention provides a novel organotin precursor capable of producing a tin-containing thin film, and an organotin compound represented by the following chemical formula 1.

[0056] [Chemical Formula 1]

[0057]

[0058] (In the above chemical formula 1,

[0059] R 1 and R 2 are independently straight or branched (C1-C10) alkyl;

[0060] R 3 Inland R 5 are independently straight or branched chain (C1-C10)alkyl, (C6-C12)aryl or (C1-C10)alkyl(C6-C12)aryl.

[0061] The organotin compound of the present invention is a compound having a novel structure containing an alkoxyalkylamide ligand, and can be usefully used as a precursor for producing a tin-containing thin film.

[0062] The organotin compound of the present invention has excellent thermal stability and high volatility and vapor pressure, making it very useful as a precursor for tin-containing thin films. Furthermore, it exists in a liquid state at room temperature and pressure, making it easy to handle.

[0063] In one embodiment, R in chemical formula 1 1 and R 2 are independently straight or branched (C1-C5) alkyl; R 3 Inland R 5 can be independently a straight or branched chain (C1-C5)alkyl, (C6-C8)aryl or (C1-C5)alkyl(C6-C8)aryl.

[0064] More specifically, R 1 and R 2 are independently methyl, ethyl n-propyl, i-propyl, n-butyl, i-butyl, t-butyl; R 3Inland R 5 may be methyl, ethyl, n-propyl, phenyl or tolyl, preferably methyl or phenyl.

[0065] In one specific example, R in the chemical formula 1 1 is methyl, ethyl or n-propyl, and R 2 is i-propyl or t-butyl, and R 3 Inland R 5 can be either methyl or phenyl, which are identical to each other.

[0066] In a preferred embodiment, R in the above formula 1 1 is a straight chain (C1-C5) alkyl, and R 2 is a branched chain (C1-C5) alkyl, and R 3 Inland R 5 can be a straight chain (C1-C5) alkyl group identical to each other. For example, R 1 is ethyl and R 2 is t-butyl and R 3 Inland R 5 can be methyl.

[0067] R in the above range 1 and R 2 The alkyl group of the compound can lower the melting point by interfering with the packing between molecules, thereby realizing an organotin compound that is more thermally stable and has higher volatility.

[0068] In one embodiment, R in chemical formula 1 3 Inland R 5 may be identical to each other as straight-chain (C1-C3) alkyl and may have improved volatility.

[0069] In a preferred embodiment, in the chemical formula 1, R 3 Inland R 5 can be methyl.

[0070] The organotin compound according to one embodiment may be selected from the following structures, but is not limited thereto.

[0071]

[0072] The organotin compound of the present invention has excellent thermal stability, enhanced volatility, and vapor pressure due to the introduction of an alkoxyalkylamide ligand, a chelating ligand that strongly binds to the central metal ion, tin. In addition, it exists in a liquid state at room temperature and pressure, making it easy to handle. Therefore, when this is employed as a thin film precursor to manufacture a thin film, a high-quality thin film with excellent reliability and uniformity can be formed at a relatively low temperature.

[0073] In addition, the present invention provides a method for producing an organotin compound of the following chemical formula 1 by reacting a halogenated tin compound of the following chemical formula 2 with an alkoxyalkylamide metal salt compound of the following chemical formula 3.

[0074] [Chemical Formula 1]

[0075]

[0076] [Chemical Formula 2]

[0077]

[0078] [Chemical Formula 3]

[0079]

[0080] (In the above chemical formulas 1 to 3,

[0081] R 1 and R 2 are independently straight or branched (C1-C10) alkyl;

[0082] R 3 Inland R 5 are independently straight-chain or branched (C1-C10)alkyl, (C6-C12)aryl or (C1-C10)alkyl(C6-C12)aryl;

[0083] X is a halogen;

[0084] M is Li, Na or K.)

[0085] In a manufacturing method according to a preferred embodiment, the R 1 Inland R 5 are each independently a straight or branched chain (C1-C5)alkyl; X is Cl; and M can be Na.

[0086] In a manufacturing method according to one embodiment, the halogenated tin compound of the chemical formula 2 and the alkoxyalkylamide metal salt compound of the chemical formula 3 may be used in a molar ratio of 1:1 to 1:3, preferably in a molar ratio of 1:1 to 1:2, and more preferably in a molar ratio of 1:1 to 1:1.5.

[0087] In a manufacturing method according to one embodiment, the reaction can be performed at 20 to 30°C for 8 to 16 hours.

[0088] In a manufacturing method according to one embodiment, the reaction may be performed in an organic solvent, and any organic solvent having high solubility in the reactants may be used without limitation. Specifically, one or more mixed organic solvents selected from hexane, diethyl ether, toluene, tetrahydrofuran, etc. may be used. Diethyl ether or toluene may be preferably used.

[0089] In a manufacturing method according to one embodiment, the reaction can be performed under an inert gas atmosphere such as nitrogen or argon.

[0090] After the above reaction, if necessary, the purity can be maximized by purification using filtration, extraction, recrystallization, distillation, sublimation, chromatography, etc.

[0091] The organotin compound manufactured by the above-described manufacturing method not only has excellent thermal stability, improved volatility and vapor pressure, but also exists in a liquid state at room temperature and pressure, making it easy to handle, making it very useful as a thin film precursor.

[0092] In addition, the present invention provides a composition for thin film deposition comprising the above-described organotin compound.

[0093] A composition for thin film deposition according to one embodiment of the present invention includes an organotin compound represented by the above chemical formula 1, and the content of the organotin compound in the composition of the present invention may be included within a range that can be recognized by a person skilled in the art in consideration of the film formation conditions of the thin film, or the thickness and characteristics of the thin film. For example, the composition for thin film deposition may include only an organotin compound, and may include a hydrocarbon solvent such as pentane, hexane, heptane, octane, decane, dodecane, ethylcyclohexane, propylcyclohexane, benzene, toluene, ethylbenzene, xylene, mesitylene, diethylbenzene, ethyl toluene, etc.; an alcohol solvent such as methanol, ethanol, propanol, isopropanol, butanol, isobutanol, etc.; an ether solvent such as diethyl ether, dipropyl ether, dibutyl ether, butyl ethyl ether, tetrahydrofuran, etc. It may include one or more mixed organic solvents selected from ester solvents such as methyl butyrate, ethyl butyrate, and propyl propionate.

[0094] The thin film deposition composition of the present invention can form a high-quality thin film with high purity, reliability, and uniformity by including the organotin compound of the above chemical formula 1.

[0095] In addition, the present invention provides a method for manufacturing a tin-containing thin film using the above-described thin film deposition composition.

[0096] A method for manufacturing a tin-containing thin film according to one embodiment can be performed on a substrate using a deposition method known in the art. Specifically, the deposition method can be a solution process or vacuum deposition, and the vacuum deposition can specifically be chemical vapor deposition (CVD), plasma-enhanced chemical vapor deposition (PECVD), atomic layer deposition (ALD), low-pressure vapor deposition, plasma-enhanced atomic layer deposition, etc.

[0097] In a method for manufacturing a tin-containing thin film according to one embodiment, the tin-containing thin film may be a tin metal thin film, a tin oxide thin film, a tin nitride thin film, or a tin nitride thin film.

[0098] The method for manufacturing a tin-containing thin film of the present invention employs an organotin compound of the above chemical formula 1, which has excellent thermal stability, improved volatility and vapor pressure, and exists in a liquid state at room temperature and pressure, as a precursor, so that it is easy to handle, does not spontaneously decompose or cause side reactions even during a continuous heating process, and has a good thin film growth rate, thereby enabling the realization of a high-quality thin film with excellent reliability and uniformity, making it very useful industrially.

[0099] In one embodiment, the method for manufacturing the thin film may include the steps of: a) heating a substrate mounted in a chamber; b) injecting an organic tin compound according to one embodiment or a composition for thin film deposition containing the same into the chamber and adsorbing the organic tin compound or a composition for thin film deposition containing the organic tin compound onto the substrate; and c) injecting a reaction gas to manufacture a thin film on the substrate. Steps b) and c) may be repeated several times depending on the thickness of the tin-containing thin film.

[0100] In one embodiment, the method for manufacturing the thin film can be controlled by the deposition conditions according to the structure or thermal characteristics of the desired thin film, and the deposition conditions may include, but are not limited to, the input flow rate of the organotin compound or the organotin-containing thin film deposition composition including the organotin compound, the input flow rate of the reaction gas, the input flow rate of the carrier gas, the pressure, the RF power, the substrate temperature, etc. of the organotin compound or the organotin-containing thin film deposition composition including the organotin compound, and the deposition conditions may be exemplified by, but not limited to, the input flow rate of the organotin-containing thin film deposition composition may be 10 to 1000 cc / min, the carrier gas may be 10 to 1000 cc / min, the reaction gas may be 1 to 1000 cc / min, the pressure may be 0.5 to 10 torr, the RF power may be 200 to 1000 W, and the substrate temperature may be controlled in the range of 80 to 400°C, preferably 200 to 400°C.

[0101] The above reaction gas is not limited, but one or more mixed gases selected from oxygen (O2), ozone (O3), water vapor (H2O), hydrogen peroxide (H2O2), nitrogen monoxide (NO), nitrous oxide (N2O), nitrogen dioxide (NO2), ammonia (NH3), nitrogen (N2), hydrazine (N2H4), amine, diamine, hydrogen (H2), argon (Ar), and helium (He) can be used, and the carrier gas is not limited as long as it is a common gas that does not react with the organotin compound of the present invention, and a non-limiting example thereof may be one or more mixed gases selected from nitrogen, helium, neon, argon, krypton, xenon, radon, etc.

[0102] The above substrate is not limited to a conventional substrate, and non-limiting examples thereof include a substrate including one or more semiconductor materials selected from Ru, TiN, Si, Ge, SiGe, GaP, GaAs, SiC, SiGeC, InAs, and InP, a rigid substrate such as a silicon on insulator (SOI) substrate, a quartz substrate, or a glass substrate for a display, or a flexible plastic substrate such as polyimide, polyethylene terephthalate (PET, PolyEthylene Terephthalate), polyethylene naphthalate (PEN, PolyEthylene Naphthalate), polymethyl methacrylate (PMMA, Poly Methyl MethAcrylate), polycarbonate (PC, PolyCarbonate), polyethersulfone (PES), and polyester.

[0103] In addition, the present invention provides a photoresist composition comprising the above-described organotin compound.

[0104] In a photoresist composition according to one embodiment, the photoresist may be a photoresist for extreme ultraviolet (EUV).

[0105] A photoresist composition according to one embodiment of the present invention includes an organotin compound represented by the above chemical formula 1, and the content of the organotin compound in the photoresist composition of the present invention may be included within a range that can be recognized by a person skilled in the art. For example, the photoresist composition may include only the organotin compound, and may include hydrocarbon solvents such as pentane, hexane, heptane, octane, decane, dodecane, ethylcyclohexane, propylcyclohexane, benzene, toluene, ethylbenzene, xylene, mesitylene, diethylbenzene, and ethyl toluene; alcohol solvents such as methanol, ethanol, propanol, isopropanol, butanol, and isobutanol; ether solvents such as diethyl ether, dipropyl ether, dibutyl ether, butyl ethyl ether, and tetrahydrofuran; ester solvents such as methyl butyrate, ethyl butyrate, and propylpropionate; It may further include one or more mixed organic solvents selected from .

[0106] The organotin compound according to the present invention comprises tin as a central metal having a very high photoionization cross-section for extreme ultraviolet photons, and one alkoxyalkylamide chelate ligand and R in the chemical formula 1 3 Inland R 5 Due to the specific combination of structures in which three alkyl groups corresponding to the same are combined, the volume change due to exposure is small, and thus, excellent mechanical properties can be realized while having further improved photosensitivity. Therefore, a photoresist composition including the same can be used to form a robust photoresist pattern with excellent resolution and photosensitivity, making it very useful in the semiconductor industry.

[0107] Hereinafter, embodiments of the present invention will be described in detail so that those skilled in the art can easily implement them. However, the present invention may be implemented in various different forms and is not limited to the embodiments described herein.

[0108] The synthesis of the organotin compound according to the present invention was performed under an inert argon or nitrogen atmosphere. 1 The structure of the obtained organotin compounds was analyzed through H NMR spectra and elemental analysis (EA).

[0109] In addition, thermogravimetric analysis (TGA) was used to determine the thermal stability, volatility, and decomposition temperature of the prepared organotin compounds. TGA analysis was performed by heating the obtained organotin compounds to 500°C at a rate of 10°C min under a nitrogen atmosphere, while injecting nitrogen gas at a rate of 5 mL / min.

[0110] [Example 1] Preparation of organotin compound SnMe3(edpa)

[0111]

[0112] SnMe3Cl (1.0 mmol) was dissolved in toluene in a Schlenk flask, and then Na(edpa) (1 mmol) was added. The mixture was stirred at room temperature for 12 h. The reaction product was filtered, and the resulting solution was distilled under reduced pressure to remove byproducts that were not soluble in the solvent, and the resulting solution was distilled (60 ℃ mTorr) to obtain a transparent liquid compound SnMe3(edpa) (0.81 mmol, yield 81%).

[0113] EA: Anal. Calcd (Found) for C 10 H 23 NOSn: C, 39.00 (38.41); H, 7.53 (7.70); N, 4.55 (4.50).

[0114] 1 H NMR (400 MHz, C6D6) δ(ppm): 3.90 (q, 2H), 1.33 (s, 9H), 1.15 (t, 3H), 0.30 (s, 9H)

[0115] 13C NMR (101 MHz, C6D6) δ(ppm): 166.81, 68.12, 36.85, 28.06, 15.03, -0.73

[0116] As shown in Fig. 1, the TG analysis results of SnMe3(edpa) manufactured in Example 1 showed one mass reduction above 70°C, resulting in a total mass reduction of 100%.

[0117] [Example 2] Preparation of organotin compound SnMe3(mdpa)

[0118]

[0119] SnMe3Cl (1.0 mmol) was dissolved in diethyl ether in a Schlenk flask, and then Na(mdpa) (1 mmol) was added. The mixture was stirred at room temperature for 12 hours. The reaction mixture was filtered, and the resulting solution was distilled (50 ℃ mTorr) to remove any byproducts that were insoluble in the solvent. The resulting solution was distilled (0.84 mmol, yield 84%) to obtain a transparent liquid compound SnMe3(mdpa).

[0120] EA: Anal. Calcd (Found) for C9H 21 NOSn: C, 36.77 (36.55); H, 7.20 (7.23); N, 4.76 (4.73).

[0121] 1 H NMR (400 MHz, C6D6) δ(ppm): 3.53(s, 3H), 1.32(s, 9H), 0.26(s, 9H)

[0122] 13 C NMR (101 MHz, C6D6) δ(ppm): 167.58, 59.68, 36.69, 27.98, -1.20

[0123] As shown in Fig. 1, the TG analysis results of SnMe3(mdpa) manufactured in Example 2 showed one mass reduction above 70°C, resulting in a total mass reduction of 100%.

[0124] [Example 3] Preparation of organotin compound SnMe3(empa)

[0125]

[0126] SnMe3Cl (1.0 mmol) was dissolved in diethyl ether in a Schlenk flask, and then Na(empa) (1 mmol) was added. The mixture was stirred at room temperature for 12 hours. The reaction mixture was filtered, and the resulting solution was distilled (45 ℃ mTorr) to remove any byproducts that were insoluble in the solvent. The resulting solution was distilled (0.65 mmol, yield 65%) to obtain a transparent liquid compound SnMe3(empa).

[0127] 1 H NMR (400 MHz, C6D6) δ(ppm): 3.88(q, 2H), 2.60 (m, 1H), 1.21 (d, 6H), 1.16(t, 3H), 0.31 (s, 9H)

[0128] 13 C NMR (101 MHz, C6D6) δ(ppm): 165.23, 68.06, 32.91, 20.17, 15.03, -0.56

[0129] As shown in Fig. 1, the TG analysis results of SnMe3(empa) manufactured in Example 3 showed one mass reduction above 70°C, resulting in a total mass reduction of 92%.

[0130] [Example 4] Preparation of organotin compound SnMe3(mpa)

[0131]

[0132] SnMe3Cl (1.0 mmol) was dissolved in diethyl ether in a Schlenk flask, and then Na(mpa) (1 mmol) was added. The mixture was stirred at room temperature for 12 hours. The reaction mixture was filtered, and the resulting solution was distilled (40 ℃ mTorr) to remove byproducts that were not soluble in the solvent. The resulting solution was distilled (0.74 mmol, yield 74%) to obtain a transparent liquid compound SnMe3(mpa).

[0133] EA: Anal. Calcd (Found) for C7H 17 NOSn: C, 31.62 (31.11); H, 6.44 (6.51); N, 5.27 (5.15).

[0134] 1 H NMR (400 MHz, C6D6) δ(ppm): 3.53 (s, 3H), 2.23 (q, 2H), 1.16 (t, 3H), 0.28 (s, 9H)

[0135] 13 C NMR (101 MHz, C6D6) δ(ppm): 163.38, 59.64, 26.85, 11.14, -0.80

[0136] As shown in Fig. 1, the TG analysis results of SnMe3(mpa) manufactured in Example 4 showed one mass reduction above 70°C, resulting in a total mass reduction of 100%.

[0137] [Comparative Example 1] Preparation of organotin compound Sn(edpa)2

[0138]

[0139] Sn(btsa)2 (1.0 mmol) was dissolved in diethyl ether, edpaH (2.0 mmol) was added, and the mixture was stirred at room temperature for 12 hours. The reaction product was filtered, and the resulting solution was distilled (90 ℃ mTorr) under reduced pressure to remove byproducts that were not soluble in the solvent, and a transparent liquid compound, Sn(edpa)2, was obtained (0.34 mmol, yield 34%).

[0140] The TG analysis results of Sn(edpa)2 manufactured in Comparative Example 1 showed one mass reduction above 100°C, resulting in a total mass reduction of 82%.

[0141] Through the above examples and comparative examples, it was confirmed that the method for producing an organotin compound according to the present invention significantly improves the yield of the desired product, and in the case of the compound of Comparative Example 1, which has a structure in which only two alkoxyalkylamide chelate ligands are bonded to a central metal, it was confirmed that it has significantly lower thermal stability and volatility compared to the organotin compound according to the present invention.

[0142] That is, the organotin compound according to the present invention is in a liquid state at room temperature and pressure, is thermally stable, and has high volatility. Therefore, when employed as a thin film precursor in a thin film deposition process, it is expected to be advantageously used to grow a high-quality thin film with excellent reliability and uniformity at a relatively low temperature, making the deposition process easy.

[0143] While the embodiments of the present invention have been described in detail above, those skilled in the art will appreciate that various modifications and variations can be made to the present invention without departing from the spirit and scope of the invention as defined in the appended claims. Therefore, modifications to future embodiments of the present invention will not depart from the scope of the invention.

Claims

1. An organotin compound represented by the following chemical formula 1: [Chemical Formula 1] In the above chemical formula 1, R 1 and R 2 are independently straight or branched (C1-C10) alkyl; R 3 Inland R 5 are independently straight or branched chain (C1-C10)alkyl, (C6-C12)aryl or (C1-C10)alkyl(C6-C12)aryl.

2. In paragraph 1, The above R 1 and R 2 are independently straight or branched (C1-C5)alkyl; R 3 Inland R 5 An organotin compound which is independently a straight or branched chain (C1-C5)alkyl, (C6-C8)aryl or (C1-C5)alkyl(C6-C8)aryl.

3. In paragraph 1, The above R 3 Inland R 5 are organotin compounds that are identically straight-chain (C1-C3) alkyl.

4. In paragraph 1, The above R 3 Inland R 5 is a methyl, organotin compound.

5. In paragraph 1, An organotin compound, wherein the organotin compound is selected from the following structures.

6. A method for producing an organotin compound of the following chemical formula 1 by reacting a halogenated tin compound of the following chemical formula 2 with an alkoxyalkylamide metal salt compound of the following chemical formula 3. [Chemical Formula 1] [Chemical Formula 2] [Chemical Formula 3] In the above chemical formulas 1 to 3, R 1 and R 2 are independently straight or branched (C1-C10) alkyl; R 3 Inland R 5 are independently straight-chain or branched (C1-C10)alkyl, (C6-C12)aryl or (C1-C10)alkyl(C6-C12)aryl; X is a halogen; M is Li, Na or K.

7. In paragraph 6, The above R 1 Inland R 5 are independently straight or branched (C1-C5)alkyl; X is Cl; A method for preparing an organotin compound, wherein M is Na.

8. A composition for thin film deposition, comprising an organotin compound according to any one of claims 1 to 5.

9. A method for manufacturing a tin-containing thin film using a thin film deposition composition according to Article 8.

10. In paragraph 9, A method for manufacturing a tin-containing thin film by chemical vapor deposition (CVD) or atomic layer deposition (ALD).

11. In paragraph 9, A method for manufacturing a tin-containing thin film, wherein the tin-containing thin film is a tin metal thin film, a tin oxide thin film, a tin nitride thin film or a tin nitride thin film.

12. A photoresist composition comprising an organotin compound according to any one of claims 1 to 5.

13. In paragraph 12, The above photoresist is a photoresist for extreme ultraviolet (EUV) lithography, a photoresist composition.

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