KR100700632B1 - The organometallic compounds for a thin film deposition with metals by using CVD or ALD and the method thereof - Google Patents

Abstract

The multipurpose organometallic compound for chemical vapor deposition or atomic layer deposition of a thin film including the present metal and a method of preparing the same include an organometallic compound having a structure of Formula 1 below.

<Formula 1>

In Formula 1, M is an element belonging to Group 3A (Al, Ga, In), Group 4A (Si, Ge, Sn), Group 4B (Ti, Zr, Hf), Group 5B (V, Nb, Ta) on the periodic table. The amide ligand and a beta-dikentonate ligand or beta-chitoester of Formula 1a, a dialkoxide of Formula 1b, an N-alkylaminoalkoxide of Formula 1c, and 1d Is bound to any one of the alkoxyalkoxides of n, wherein n has an integer of 3 (group 3A), 4 (group 4A, 4B), or 5 (group 5B), and m is a group containing a central element It is a positive integer less than n.

Chemical Vapor Deposition, Atomic Layer Deposition, Organic Metal Compounds

Description

The organometallic compounds for a thin film deposition with metals by using CVD or ALD and the method

The present invention is to deposit various thin films applied to semiconductor devices, such as metal nitride, metal oxide, and metal silicide using chemical vapor deposition (CVD) or atomic layer deposition (ALD). A multipurpose organometallic compound and a method for producing the same.

As the degree of integration of memory and non-memory semiconductor devices increases day by day, and the structure thereof becomes more complex, the importance of step coverage in depositing various thin films on a substrate is increasing. MOCVD (Metal Organic Vapor Deposition) method, which uses volatile organometallic compounds, is classified into two types according to the vaporization and transport method of raw materials. The bubbler method of bubbling and sublimation and the vaporizer method of increasing the volatilization rate of the compound by dropping the compound solution in which the organometallic compound is dissolved in a suitable solvent on a hot plate heated to a high temperature and vaporizing it together with the solvent. have. Here, the vaporizer method is also referred to as a liquid delivery system (hereinafter referred to as LDS) because the raw material is transferred in a liquid state.

On the other hand, in the chemical vapor deposition method, the conditions that the organometallic compound should have include high vaporization characteristics, a large gap between the vaporization temperature and decomposition temperature, low toxicity, chemical stability, thermal stability, and easy compound synthesis and pyrolysis. In addition, there should be no side reaction that spontaneously decomposes or reacts with other substances in the process of vaporization and transfer to the gas phase, and in particular, the composition of each component metal introduced into the thin film during the preparation of the multi-component thin film should be easily controlled. At the deposition temperature, the organometallic compounds have similar decomposition behaviors to form high quality thin films.

Here, the characteristics of metal nitride, metal oxide, metal silicide and the like used in the thin film for semiconductor will be described. Titanium nitride (TiN), tantalum nitride (TaN), and zirconium nitride (ZrN), which are representative metal thin films, are applied to a contact portion with a silicon layer of a doped semiconductor or used as an interlayer wiring material. It is used as a diffusion barrier with (Cu) and is also used as an adhesion layer when depositing a tungsten (W) thin film on a substrate.

In addition, titanium (Ti) and tantalum (Ta), which are used as thin metal silicide films, are used as an adhesive layer between a silicon substrate, an electrode, a wiring material, and a diffusion barrier film. It is used as a thin film to form (TaSi) to improve adhesion to a silicon substrate.

In addition, metal oxides such as alumina (Al ₂ O ₃ ), titania (TiO ₂ ), and tantalum (Ta ₂ O ₅ ) are applied to a capacitor of a semiconductor device and have a higher dielectric than silicon oxide (SiO ₂ ). The constant? Is applied to high density, high capacity memory semiconductors.

For example, as described above, in order to deposit a thin film of excellent physical properties, the selection of an organometallic compound may be the most important requirement. For example, in order to deposit a representative titanium nitride (TiN) among the metal nitrides, titanium chloride (TiCl _{4) may be used.} ) Is used mainly. However, despite the excellent economics of this metal, there are some problems as follows. First, the chlorine atoms present in the compound itself may be introduced into the deposited titanium nitride thin film to cause corrosion of the wiring material aluminum. Second, in the case of aluminum wiring having a low melting point because the process is performed at a high temperature of about 600 ° C. It is difficult to apply, and during the third process, non-volatile by-products such as titanium chloride ammonia complex [TiCl ₄ : (NH ₃ ) _x ] and ammonium chloride salt (NH ₄ Cl) deposit particles in the thin film, thus causing a fatal disadvantage in the semiconductor chip manufacturing process. cause.

Further, the process using the tantalum nitride (TaN) or zirconium nitride (ZrN) chloride, tantalum (TaCl _5), zirconium chloride (TaCl ₅₎ in order to deposit or the like is now these compounds to provide enough vapor pressure to deposit as a solid compound It is difficult to deliver the compound.

In addition, the production of titanium nitride (TiN) thin films using titanium amide [Ti (NR ₂ ) ₄ : R = Me (CH ₃ ), Et (C ₂ H ₅ )], and tantalum ethoxide used as dielectric thin films ( Although a method for producing tantalum (Ta ₂ O ₅ ) using tantalumethoxide has been developed, the process development is difficult due to the instability and risk of the compound itself.

The present invention has been made to solve the above problems, the manufacturing process of the metal nitride, metal oxide, and metal silicide thin film used for the diffusion barrier film, dielectric film, adhesive film, etc. in the next-generation semiconductor device process using the chemical vapor deposition method It improves process problems due to thermal and chemical instability of organometallic compounds, so it does not react sensitively to excellent thermal stability, high vapor pressure, moisture, air, etc., and only changes process conditions such as change of reaction gas and deposition temperature. An object of the present invention is to provide an organometallic compound for chemical vapor deposition or atomic layer deposition of a thin film containing a metal capable of continuous deposition of a metal and a method of manufacturing the same.

Hereinafter, the present invention will be described in more detail.

In Formula 1, M is an element belonging to Group 3A (Al, Ga, In), Group 4A (Si, Ge, Sn), Group 4B (Ti, Zr, Hf), Group 5B (V, Nb, Ta) on the periodic table. The amide ligand and the beta-dikentonate ligand or beta-chitoester of Formula 1a, the dialkoxide of Formula 1b, and the N-alkylamino of Formula 1c. An alkoxide, which is combined with any one of the alkoxyalkoxides of Formula 1d. In addition, n has an integer of 3 (group 3A), 4 (group 4A, 4B), 5 (group 5B) in the formula, m is a positive integer less than n depending on the group containing the central element, m 'takes an integer from 1 to 6.

In addition, the amide ligands R ¹ and R ² are each independently selected from an alkyl group having 1 to 4 carbon atoms or a perfluoroalkyl group, alkylsilicone, aminoalkyl, alkoxyalkyl, R ³ , R ⁴ , R ⁵ R ⁶ , R ⁷ , R ⁸ and R ⁹ are each independently hydrogen (H), fluorine (F), or an alkyl or perfluoroalkyl group having 1 to 8 carbon atoms, alkylsilicone, aminoalkyl, alkoxyalkyl, alkoxy And any of amino groups are used.

Furthermore, according to the present invention, beta-dikentonate ligands used in the following Chemical Formula 1a include 2,4-pentanedione [2,4-pentandione (hereinafter acacH): R ³ = H, R ⁴ = R ⁵ = Me (CH ₃ )] and 2,2,6,6-tetramethylheptanedione [2,2,6,6-tentramethylheptandione (hereinafter tmhdH): R ³ = H, R ⁴ = R ⁵ = Bu (C ₄ H ₉ )], 1,1,1,5,5,5-hexafluoropentanedione [1,1,1,5,5,5-hexafluoropentandione (hereinafter hfacH) : R ³ = H, R ⁴ = R ⁵ = CF ₃ )] is typically used.

Preferably, in Formula 2, R ³ may be taken from hydrogen (H), fluorine (F), or an alkyl or perfluoroalkyl group having 1 to 8 carbon atoms, alkylsilicone, aminoalkyl, alkoxyalkyl, alkoxy, amino group , R ⁴ and R ⁵ are each independently an alkyl group, alkylsilicone or perfluoroalkyl group, aminoalkyl, alkoxyalkyl, alkoxy, amino group having 1 to 8 carbon atoms, acacH, tmhdH, hfacH are most commonly used.

According to the present invention, in the case of Formula 1b, a case of dial alcohol represented by the following formula may be applied, wherein R is hydrogen or 1 to 5 alkyl groups, perfluoroalkyl group, alkylsilicone, aminoalkyl, alkoxyalkyl , Alkoxy and amino groups are used. Most representative examples include ethylene glycol, propane-1, 2-diol, butane-1, 2-diol, 2-methylpentane, 4-diol, and the like.

In addition, in the case of Formula 1c, the case of N-alkylaminoalcohol represented by the following formula may be applied, wherein R is hydrogen or 1 to 5 alkyl groups, perfluoroalkyl group, alkylsilicone, aminoalkyl, alkoxyalkyl , Alkoxy and amino groups are used. The most representative ones include N-dimethylaminoethanol and N-dimethylaminopropane.

In addition, in the case of Formula 1d, N-alkoxyalcohol represented by the following formula may be applied, wherein R is hydrogen or 1 to 5 alkyl groups, perfluoroalkyl group, alkylsilicone, aminoalkyl, alkoxyalkyl, alkoxy And amino groups are used. The most representative ones are methoxy ethanol, ethoxy ethanol, propoxy ethanol and the like.

According to the present invention, preferably, in the compound of Chemical Formula 1, M may be silicon (Si), germanium (Ge), tin (Sn), or titanium (Ti), which belongs to group 4A, on the periodic table. ), Zirconium (Zr), hafnium (Hf), m may be defined as an integer from 3 to 1, of which titanium is preferred.

In addition, in the compound of Formula 1, M is vanadium (V), niobium (Nb), and tantalum (Ta) belonging to Group 5B on the periodic table, and m may be defined as an integer from 4 to 1. And tantalum are preferable.

In addition, according to the present invention, in the compound of Chemical Formula 1, as shown in Chemical Formula 5 below, the compound includes aluminum (Al), gallium (Ga), and indium (In), in which M belongs to group 3A on the periodic table, and m is 2 to 1. It can be defined as an integer of, of which aluminum is representative.

According to the present invention, the organometallic compounds defined by Chemical Formula 1 are semiconductor processes such as diffusion barrier films (TiN, TaN), adhesive films (Ti, Ta), dielectric films (Ta ₂ O ₅ , TiO ₂ , Al ₂ O ₃ ), and the like. Can be used as a raw material for producing a thin film, the compounds developed as described above are prepared by the manufacturing process as shown in Schemes 1 to 3. At this time, all the reaction process is carried out in the inert air stream (Ar, N ₂ ) to exclude contact with air.

Scheme 1 is a secondary amine defined by R ¹ and R ² as shown in Formula 1 to a nucleic acid solution of normal-butyllithium (n-BuLi) cooled to low temperature using dry ice / acetone Stirring at room temperature with slow addition produces the product R ¹ R ² NLi. The metal dialkylamide [Ti (NR ¹ R ² ) ₄ , Zr (Ti (NR ¹ R ² ) ₄ , Zr () was added to the nucleic acid suspension solution of the prepared amide by heating and stirring the metal chloride TiCl ₄ , ZrCl ₄ , TaCl ₅ , AlCl _3, etc. NR ¹ R ² ) ₄ , Ta (NR ¹ R ² ) ₅ , Al (NR ¹ R ² ) ₃ ] are prepared, such as R ¹ R ² = CH ₃ (Me), R ¹ R ² = C ₂ H ₅ Preference is given to (Et), R ¹ R ² = CH ₃ , C ₂ H ₅ .

Titanium and tantalum amide compounds to replace a part of the amide ligand is a compound of the present invention defined as the following formulas 6 and 7 when reacted with acacH, hfacH, tmhdH and the like in the beta-dikitonate defined as Formula 3 Can be easily produced. In this case, m is 2 and 3, and the main product is effectively prepared when beta-dikitonate is acacH, hfacH.

Of the titanium compound of Formula 6, R ¹ R ² = C ₂ H ₅ (Et), m = 1, 2 (Et ₂ N) ₂ Ti (hfac) ₂ , (Et ₂ N) ₂ Ti (hfac) ₃ , (Et ₂ N) ₂ Ti (acac) ₂ is a liquid or solid compound exhibiting high vapor pressure at low temperatures and is excellent in stability as an organometallic compound which is not sensitive to air and moisture.

In addition, in the tantalum compound represented by Chemical Formula 7, R ¹ R ² = CH ₃ (Me), and m = 3 (Me ₂ N) ₂ Ta (hfac) ₃ and (Me ₂ N) ₂ Ta (acac) ₃ are low. It is a solid compound exhibiting high vapor pressure at temperature and is excellent in characteristics as a stable organometallic compound which is not sensitive to air and moisture.

In addition, the metal amide compound to replace a part of the amide ligand may be reacted with dialcohols, alkylaminoalcohols, and alkoxyalcohols as in Scheme 3 to prepare compounds represented by Chemical Formulas 1b, 1c, and 1d. The detailed reaction conditions are similar to those of the beta-dikitone described above, and are the same as those of ethylene glycol, 2-methylpentan-2,4-ol, dimethylaminoethanol, dimethylaminopropanol, and me (eth) ethoxyethanol. Manufactured effectively.

Hereinafter, a method for preparing the compound will be described.

Preparation of (Et ₂ N) ₂ Ti (acac) ₂

5 moles of 2,4-pentanedione (acacH) under nitrogen stream in 500 ml solution of 1 mole of yellow nucleic acid (Tetrakis (diethylamino) titanium; When slowly added, the nucleic acid solution turns orange immediately and after stirring for 4 hours at room temperature, the nucleic acid solution turns red and dark red. At this time, when the supernatant and the precipitate are separated and dried, the precipitate produces an ocher solid, and the supernatant produces a yellow liquid. Here, by distilling the dried yellow liquid at 48 ~ 55 ℃ / 10 ^-2 torr (Et ₂ N) ₂ Ti (hfac) ₂ It can be prepared, the reaction scheme is as follows.

Preparation of (Et ₂ N) ₂ Ti (hfac) ₂ , (Et ₂ N) Ti (acac) ₃

When 5 mol of hfacH was slowly added to 0 mol of TDEAT nucleic acid solution prepared by Scheme 1 and 2 at 0 ° C., an orange precipitate was formed with exothermic reaction and the solution was yellow-orange. When the yellow-orange mixture is stirred again at room temperature for 4 hours, the supernatant is separated into a supernatant and a precipitate. When the volatile material is removed in a vacuum at room temperature, the supernatant is an orange gel, and the precipitate is a red solid. Will remain. At this time, when the red solid is sublimed between 60 ~ 70 ℃ to obtain an orange solid (Et ₂ N) Ti (acac) ₂ , the gel supernatant distilled between 25 ~ 35 ℃ yellow distillate (Et ₂ N) ₂ Ti (hfac) ₂ is obtained. Hydrogen nuclear magnetic resonance ( ¹ H-NMR) analysis data and physical properties of the prepared are shown in Table 1.

In addition, in the reaction scheme 4, TDMAT and 5hfacH were added to examine the reaction. The reaction was the same as the reaction of (Et ₂ N) ₂ Ti (acac) ₂ , but the product of the reaction was a solid compound which sublimates to precipitate white crystals. . In this case, some of the solid products are not used as the MOCVD organometallic compound because some of the solid products are deteriorated during the sublimation process, but the reaction shows that the sublimed white crystals are combined with the titanium compound as a result of analysis by nuclear magnetic resonance analyzer. Gas HN (CH ₃ ) ₂ was detected. This HNMe ₂ gas is shown to be bonded to the titanium compound as a complex. Hydrogen nuclear magnetic resonance ( ¹ H-NMR) analysis data and physical properties of the (Me ₂ N) ₂ Ti (hfac) ₂ prepared by the above reaction scheme are shown in Table 1.

Preparation of (Me ₂ N) ₂ Ta (acac) ₃

500 ml solution of 1 mole of yellow nucleic acid (Pentakis (dimethylamino) titanium) prepared through Schemes 1 and 2 was slowly added to 6 moles of 2,4-pentanedione (acacH) at 0 ° C. under nitrogen stream. The solution immediately turns orange and a white solid is formed by stirring at room temperature for 4 hours. The resulting solid compound is dried in vacuo for purification and distilled at 25˜35 ° C./10 ⁻² torr to give (Me ₂ N) ₂ Ta (acac) ₃ , wherein the reaction is shown in Scheme 5 below. Hydrogen nuclear magnetic ( ¹ H-NMR) analysis data and physical properties of this compound are shown in Table 2 below.

Preparation of (Me ₂ N) ₂ Ta (hfac) ₃

In the same manner as the above (Me ₂ N) ₂ Ta (acac) _{3 When} hfacH corresponding to 6 times the number of moles of the mole solution of PDMAT 1 mole is slowly added at 0 ° C., an orange precipitate and yellow-orange color with exothermic reaction Solution is produced. After stirring the yellow-orange mixture at room temperature for 4 hours, volatiles are removed under vacuum at room temperature, leaving an orange solid. Sublimation of this solid again between 50 ~ 70 ℃ to give a yellow solid (Me ₂ N) ₂ Ta (hfac) ₃ , the physical properties of this material are shown in Table 2.

According to the present invention, organometallic compounds having the same molecular formula as described above may be deposited on a substrate using a reaction gas as in Scheme 4 below.

Particularly, (Et ₂ N) ₂ Ti (hfac) ₂ and (Et ₂ N) ₂ Ti (acac) ₂ compounds exist in the liquid phase at room temperature and have a high vapor pressure. It is easy to control the compound delivery rate for reproducibility in the thin film manufacturing process using the deposition method, and it is an effective process because it is possible to use a direct liquid injector (DLI) or liquid delivery system (LDS). Development is possible.

In addition, since (Et ₂ N) ₂ Ti (hfac) ₂ and (Me ₂ N) ₂ Ta (acac) ₂ compounds exist as solids at room temperature but have a very high vapor pressure at low temperatures, chemical vapor deposition using a bubbler is used. It is possible to use DLI or LDS in addition to the following solvents. For example, solvents used for organometallic compound solutions include saturated hydrocarbons, organic ethers, aromatic hydrocarbons, and amines (including heterocyclic amines). Preferably, among the heterocyclic amines, 1-alkylpyrrolidine, 1-alkylallyreridine, 4-alkylmorpholine, 1,4-dialkylpiperazine and the like are excellent solvents of the organometallic compound solution.

      As mentioned above, although this invention was demonstrated by the limited Example, this invention is not limited by this and it is various in the range of equality of a common technical idea in the technical field to which this invention belongs, and a claim described below. Of course, modifications and variations are possible.

According to the multipurpose organometallic compound for chemical vapor deposition or atomic layer deposition of a thin film containing a metal of the present invention and a method for preparing the same, the compounds (Et ₂ N) ₂ Ti (hfac) ₂ , (Et ₂ N) ₂ Ti ( acac) ₂ , (Et ₂ N) ₂ Ti (hfac) ₃ , (Me ₂ N) ₂ Ta (hfac) ₃ uses a single organometallic compound as in Scheme 4 to change the process conditions such as reaction gas and deposition temperature. It can be used as a versatile compound that can continuously deposit diffusion barrier films (TiN, TaN), adhesive films (Ti, Ta), dielectric films (TiO ₂ , Ta ₂ O ₃ ), etc. It is a liquid or solid compound that shows high vapor pressure even at temperature, and thus has a great effect on reproducible deposition because it facilitates flow rate control during deposition. In addition, since the deposition rate is also proportional to the vapor pressure, it is advantageous in terms of economics, while other common compounds are easily decomposed upon contact with air, while these compounds are stable for a considerable time, so there is an advantage of easy handling. In addition, since the organometallic compound is thermally stable, it is possible to increase the reliability and efficiency of the process.

Claims (19)

An organometallic compound having a structure represented by the following formula (1) in an organometallic compound used for chemical vapor deposition or atomic vapor deposition in which various thin films of metal nitride, metal oxide, metal oxynitride, metal silicide, metal, and the like are deposited on a silicon substrate. <Formula 1>

<Formula 1a>

<Formula 1b>

<Formula 1c>

<Formula 1d>

In Formula 1, M is a central metal, and is represented by Group 3A (Al, Ga, In), Group 4A (Si, Ge, Sn), Group 4B (Ti, Zr, Hf), Group 5B (V, Nb, Ta) on the periodic table. And an amide ligand, a beta-dikentonate ligand or beta-chitoester of Formula 1a, a dialkoxide of Formula 1b, or a compound of Formula 1c. N-alkylaminoalkoxide, which is combined with any one of the alkoxyalkoxides of Formula 1d, wherein n has an integer of 3 (Group 3A), 4 (Group 4A, 4B), 5 (Group 5B), m Is a positive integer less than n, depending on the group containing the central element, m 'takes an integer of 1 to 6. In addition, the amide ligands R ¹ and R ² are each independently selected from an alkyl group having 1 to 4 carbon atoms or a perfluoroalkyl group, alkylsilicone, aminoalkyl, alkoxyalkyl, R ³ , R ⁴ , R ⁵ R ⁶ , R ⁷ , R ⁸ and R ⁹ are each independently hydrogen (H), fluorine (F), or an alkyl or perfluoroalkyl group having 1 to 8 carbon atoms, alkylsilicone, aminoalkyl, alkoxyalkyl, alkoxy And any one of amide groups is taken. The method of claim 1, The beta-diquitonate ligand of Formula 1a is an organometallic compound, characterized in that having the structure of formula (2). <Formula 2>

The method of claim 1, The amide ligands R ¹ and R ² bonded to Formula 1a may be any one of C ₂ H ₅ (Et) and CH ₃ (Me). The method according to claim 1 or 2, R ³ of the beta-dikitonate ligand bound to Formula 1a is hydrogen (H), R ⁴ and R ⁵ is any one of CH ₃ (acac), CF ₃ (hfac), C (CH ₃ ) ₄ (tmhd) An organometallic compound comprising one. In Chemical Formula 1 of claim 1, M is any one of silicon (Si), germanium (Ge), tin (Sn), or titanium (Ti), zirconium (Zr), and hafnium (Hf) belonging to group 4A in the periodic table as shown in Formula 3 below. R ¹ and R ² are composed of any one of CH ₃ (Me) and C ₂ H ₅ (Et), and m is an organometallic compound, characterized in that it takes an integer from 3 to 1. <Formula 3>

In Chemical Formula 3 of claim 5, M is titanium (Ti), R ³ is H, R ⁴ and R ⁵ are any one of CH ₃ (acacH), CF ₃ (hfacH), R ¹ and R ² are CH ₃ (Me), C ₂ An organometallic compound comprising any one of H ₅ (Et), m taking an integer of 2 or 3. In Chemical Formula 1 of claim 1, The central metal M is any one of vanadium (V), niobium (Nb) and tantalum (Ta) belonging to group 5B on the periodic table, and R ¹ and R ² are any of CH ₃ (Me) and C ₂ H ₅ (Et). Organometallic compound having a structure of Formula 4, characterized in that one consisting of, m is any one of 4 to 1. <Formula 4>

In Chemical Formula 4 of claim 7, The central metal M is tantalum (Ta), R ³ is H, R ⁴ and R ⁵ is any one of CH ₃ (acacH), CF ₃ (hfacH), m is an organic, characterized in that 2 or 3 Metal compounds. In Chemical Formula 1 of claim 1, The central metal M is any one of aluminum (Al), gallium (Ga) and indium (In) belonging to group 3A on the periodic table, and R ¹ and R ² are any of CH ₃ (Me) and C ₂ H ₅ (Et). An organometallic compound having a structure represented by Formula 5, wherein m is an integer of 2 or 1. <Formula 5>

In Chemical Formula 5 of claim 9, The central metal M is aluminum (Al), R ³ is H, R ⁴ and R ⁵ is CH ₃ (acacH), CF ₃ (hfacH) is an organometallic compound characterized in that. The method of claim 1, The organometallic compound is an organometallic compound, characterized in that combined with a dialkoxide ligand. The method of claim 1, The organometallic compound is an organometallic compound, characterized in that coupled with the N-alkylaminoalkoxide ligand. The method of claim 12, The N-alkylaminoalkoxide ligand is an organometallic compound characterized in that N-dimethylaminoethoxide. The method of claim 1, The organometallic compound is an organometallic compound, characterized in that combined with an alkoxyalkoxide ligand. The method of claim 14, The alkoxy alkoxide ligand is an organometallic compound, characterized in that ethoxy or methoxy ethoxide. The method of claim 1, Formula 1 is an organometallic compound, characterized in that coupled to the beta-chitoester ligand comprising t-butyl acetoacetate or ethyl acetoacetate. A solution obtained by dissolving or diluting the compound of claim 1 in a solvent of saturated or unsaturated hydrocarbons, ethers, esters, alcohols, amines, sulfides, phosphines, beta-diketones and beta-chitoesters. A method of depositing a thin film by chemical vapor deposition or atomic layer deposition. Providing a metal amide compound solution; Reacting the solution with any one of beta-dichitonate, beta-chitoester, dialkoxide, N-alkylaminoalkoxide and alkoxyalkoxide; and And removing the unreacted ligand and the organic solvent by heating. Method for producing an organometallic compound, characterized in that it is prepared to have a structure of Formula 1. The method of claim 18, Comprising the metal amide compound solution is the step of adding an amine to the normal- butyllithium nucleic acid solution; And Preparing a metal dialkylamide by adding metal chloride to the solution.