KR20240033510A - Novel Organo-Molybdenum Compounds, Preparation method thereof, and Method for deposition of thin film using the same - Google Patents

Abstract

The present invention relates to a molybdenum organometallic compound, a method for producing the same, and a method for producing a thin film using the same. More specifically, when producing a thin film through chemical vapor deposition or a solution process, thermal stability and volatility are The present invention relates to an improved molybdenum organometallic compound capable of easily producing high-quality molybdenum-containing thin films at low temperatures, a method for producing the same, and a method for producing thin films using the same.

Description

Novel Organo-Molybdenum Compounds, Preparation method thereof, and Method for deposition of thin film using the same}

The present invention relates to a novel molybdenum organometallic compound, a method for producing the same, and a method for forming a thin film using the same. More specifically, in manufacturing a thin film through chemical vapor deposition or solution process, thermal stability and The present invention relates to a novel molybdenum organometallic compound that has improved volatility and can easily produce high-quality molybdenum-containing thin films at low temperatures, a method for producing the same, and a method for producing thin films using the same.

Thin films containing molybdenum can be used in organic light-emitting diodes, liquid crystal displays, plasma display panels, field emission displays, thin-film solar cells, low-ohmic resistance, other electronic devices and semiconductor devices, and are mainly used as barrier films, etc. It is used as a member of electronic components.

The molybdenum thin film, molybdenum oxide, molybdenum nitride thin film, etc. are widely used in various fields due to their low resistance, large work function, and thermal and chemical stability. For example, molybdenum thin film is 15 It has a low resistivity of less than μΩcm and can be applied as wiring for display devices. Molybdenum dioxide (MoO ₂ ) has metal-like conductivity and is used as a hydrocarbon oxidation catalyst, solid oxide fuel cell (SOFC) anode, and high It can be applied to capacity reversible lithium ion battery (LIB) anodes, molybdenum trioxide (MoO ₃ ) exhibits electrochromic and catalytic properties, nanostructured gas sensors and solid-state lithium ion batteries. can be applied to

Recently, molybdenum disulfide (MoS ₂ ) has been studied as a next-generation material because it has various application possibilities in photocatalysts, energy storage devices, sensors, and solar cells. This molybdenum disulfide (MoS ₂ ) has a layered structure and exhibits a two-dimensional structure structurally similar to graphene. However, graphene has conductive properties, so its practicality is limited, while layered molybdenum disulfide has semiconductor properties, so it has excellent practicality. For example, molybdenum disulfide can control its physical properties by adjusting the bandgap. It is capable of absorbing and emitting light efficiently, and also has high electron mobility and high transparency and flexibility, so it can be used in thin film production or ultra-small electronic devices, so it has the potential to be used in various industries. , Specifically, it is a new material with ductility to implement flexible displays and is also being studied as a material that can be applied as a replacement for Oxide TFT and Graphene TFT.

Meanwhile, as a thin film deposition method for semiconductor devices, methods using chemical vapor deposition (CVD) and atomic layer deposition (ALD) are being studied, and design rules have recently changed due to miniaturization of semiconductor devices. As this decreases, low-temperature processing, precise thickness control, uniformity and spreadability of thin films can be satisfied by using the atomic layer deposition (ALD) method, which follows a self-limiting surface reaction mechanism as a deposition method. Thin film formation is widely used.

When manufacturing a molybdenum thin film by this chemical vapor deposition (CVD) or atomic layer deposition (ALD) process, the degree of deposition and deposition control characteristics are determined depending on the characteristics of the metal precursor, so a metal precursor with excellent properties is required. Development is needed. Until now, as raw materials for the chemical vapor growth method for producing thin films containing molybdenum oxide, molybdenum carbonyl [Mo(CO) ₆ ], molybdenum acetylacetonate, molybdenum chloride (MoCl ₃ or MoCl ₅ ), Molybdenum fluoride (MoF ₆ ), MoO ₂ (2,2,6,6-tetramethylheptane-3,5-dione) 2, biscyclopentadienyl molybdenum dihydride, bismethylcyclopentadiene Organic molyb such as nyl molybdenum dihydride, bisethylcyclopentadienyl molybdenum dihydride, bisisopropyl cyclopentadienyl molybdenum dihydride, and biscyclopentadienyl imide molybdenum. Denum compounds and molybdenum oxychloride (MoO ₂ Cl ₂ or MoOCl ₄ ) have been reported, and molybdenum amidimide compounds have been reported as precursor materials for forming molybdenum-containing thin films by atomic layer deposition (ALD). It has been reported. As a conventional technology related to the precursor for forming such a thin film, Korean Patent Publication No. 10-2007-0073636 presents a method for manufacturing a tungsten or molybdenum precursor containing a diamine ligand, and Korean Patent Publication No. No. 10-2015-0084757 discloses a molybdenum precursor composed of a cyclopentadienyl group and an imido group as a ligand, but these still need room for improvement in terms of thermal stability, chemical reactivity, volatility, etc.

Therefore, a novel molybdenum organometallic compound that has improved thermal stability and volatility and can be easily used as a precursor for metal components in the production of molybdenum-containing thin films at low temperatures, and thin films with improved physical properties using the same. The need for development of manufacturing processes continues to be required.

Korean Patent Publication No. 10-2007-0073636 (publication date: July 10, 2007) Korean Patent Publication No. 10-2015-0084757 (publication date: July 22, 2015)

The first technical task to be achieved by the present invention is to provide a novel molybdenum organometallic compound as a precursor that has improved thermal stability and volatility and allows for the easy production of molybdenum-containing thin films at low temperatures.

In addition, the second technical problem to be achieved by the present invention is to provide a novel method for producing the molybdenum organometallic compound.

In addition, the third technical problem to be achieved by the present invention is to provide a method of producing a molybdenum-containing thin film using the molybdenum organometallic compound as a precursor.

In order to achieve the above technical problems, the present invention provides an organometallic compound represented by the following [Chemical Formula A].

[Formula A]

In Formula A,

The M is molybdenum (Mo),

R ₁ to R ₄ are each the same or different and independently of each other hydrogen, deuterium, C ₁ -C ₁₀ linear, branched or cyclic alkyl group; and a C ₁ -C ₁₀ linear, branched or cyclic halogenated alkyl group,

R ₅ and R ₆ are each the same or different and independently from each other a linear, branched or cyclic alkyl group of C ₁ -C ₁₀ ; and a C ₁ -C ₁₀ linear, branched or cyclic halogenated alkyl group; Any one selected from,

Here, the imido group containing R ₅ and the imido group containing R ₆ may each face each other with respect to the central atom M or be arranged perpendicularly to each other with respect to the central atom M.

Additionally, the present invention provides a method for producing a molybdenum-containing thin film using the organometallic compound represented by [Formula A] as a metal precursor.

In addition, the present invention provides a molybdenum compound represented by Compound C below; and a compound represented by Compound D1 and a compound represented by Compound D2, respectively, as reactants.

[Compound C] [Compound D1] [Compound D2]

[Formula A]

In compound C,

R ₇ and R ₈ are the same or different and independently of each other, a C ₁ -C ₁₀ linear, branched or cyclic alkyl group; and a C ₁ -C ₁₀ linear, branched or cyclic halogenated alkyl group,

X ₁ and X ₂ are each the same or different and independently of each other, any halogen element selected from F, Cl and Br,

In Compound C, Compound D1, Compound D2 and Formula A, M, R ₁ to R ₆ are each as defined above,

In the compound A, the imido group containing R ₅ and the imido group containing R ₆ may each face each other with respect to the central atom M or be arranged perpendicularly to each other with respect to the central atom M.

Since the organometallic compound represented by [Formula A] of the present invention exhibits improved thermal stability and volatility, it contains molybdenum such as molybdenum thin film, molybdenum oxide thin film, and molybdenum chalcogenide thin film. It can be used as a precursor to form a thin film, and when used, it can form a large-area or uniform thin film. In particular, it contains both molybdenum component and sulfur (S) component in one molecule. , when manufacturing a molybdenum chalcogenide thin film (MoS ₂ ), etc., there is an advantage in that the molybdenum chalcogenide thin film can be easily formed even without adding an additional chalcogenide source.

Figure 1 is an X-ray crystal structure of Mo(N ^t Bu) ₂ (mdpaS) ₂ compound prepared according to Preparation Example 1 of the present invention.
2 is the TGA measurement result for the compounds prepared according to Preparation Examples 1 and 2 of the present invention.

Hereinafter, the present invention will be described in more detail. Unless otherwise defined, all technical and scientific terms used in this specification have the same meaning as commonly understood by a person skilled in the art to which the present invention pertains. In general, the nomenclature used herein is well known and commonly used in the art.

Throughout the specification of the present application, when a part "includes" a certain component, this means that it may further include other components rather than excluding other components unless specifically stated to the contrary.

The present inventors have achieved the above technical problems and developed a molybdenum thin film with excellent properties; or molybdenum oxide thin film; As a result of efforts to develop a precursor for producing a molybdenum chalcogenide thin film, two alkoxy groups, corresponding to ligands with a structure in which hydrogen atoms are removed from the same or different compounds represented by Compound D1 and Compound D2, were obtained. The thiocarboxamide ligand is coordinated to the central metal atom, molybdenum (Mo), and two identical or different imido ligands are each coordinated to the central metal atom, molybdenum (Mo). It was possible to prepare an organometallic complex with this structure.

[Compound D1] [Compound D2]

That is, the organometallic compound represented by the formula A is a useful precursor for forming a molybdenum thin film, a molybdenum oxide thin film, or a molybdenum chalcogenide thin film, and contains two alkoxy thio carboxyls that are the same or different from each other in the molecule. Contains an amide ligand; In addition, it has a structure in which two identical or different imido ligands coordinate with molybdenum, and through this structure of Chemical Formula A, it has high volatility, excellent chemical and thermal stability, and a fast deposition rate of thin films even at relatively low temperatures. The present invention was completed by confirming that the properties could be expressed.

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

The present invention provides an organometallic compound containing molybdenum (Mo), represented by the following [Chemical Formula A].

[Formula A]

In Formula A,

The M is molybdenum (Mo),

R ₁ to R ₄ are each the same or different and independently of each other hydrogen, deuterium, C ₁ -C ₁₀ linear, branched or cyclic alkyl group; and a C ₁ -C ₁₀ linear, branched or cyclic halogenated alkyl group,

R ₅ and R ₆ are each the same or different and independently from each other a linear, branched or cyclic alkyl group of C ₁ -C ₁₀ ; and a C ₁ -C ₁₀ linear, branched or cyclic halogenated alkyl group; Any one selected from,

Here, the imido group containing R ₅ and the imido group containing R ₆ may each face each other with respect to the central atom M or be arranged perpendicularly to each other with respect to the central atom M.

The organometallic compound represented by [Formula A] according to the present invention is a ligand that coordinates with molybdenum (Mo), a central metal, and is an alkoxy thiocarboxamide ligand containing R ₁ and R ₂ , R ₃ and It is characterized by a structure in which each alkoxy thio carboxamide ligand containing R ₄ is coordinated, and an imido ligand containing R ₅ and an imido ligand containing R ₆ are coordinated. .

The organometallic compound represented by [Formula A], which has a structure according to Formula A and is coordinated with two imido ligands and two alkoxy thio carboxamide ligands, can exhibit thermal stability and good volatility. , can be applied as a precursor for molybdenum metal thin films, molybdenum oxide thin films, or molybdenum chalcogenide thin films.

In the organometallic compound represented by [Formula A] according to the present invention, the substituents R ₁ to R ₄ in the alkoxy thio carboxamide ligand are preferably each the same or different and independently from each other, C ₁ -C It may be a linear, branched or cyclic alkyl group of ₆ ; more preferably, the substituents R ₁ to R ₄ are each the same or different and independently of each other, CH ₃ , C ₂ H ₅ , CH(CH ₃ ) ₂ , It may be any one selected from nC ₃ H ₈ and C(CH ₃ ) ₃ , and in this case, the organometallic compound represented by [Formula A] has improved volatility and excellent thermal stability due to its low molecular weight. You can have

In addition, the substituents R ₁ and R ₃ in the alkoxy thio carboxamide ligand in Formula A are more preferably the same or different and independently of each other, C ₂ H ₅ , CH(CH ₃ ) ₂ and C ( CH ₃ ) ₃ , and more preferably, the substituents R ₂ and R ₄ may be the same or different and independently from each other, and may be any one selected from CH ₃ and C ₂ H ₅ .

Meanwhile, in the organometallic compound represented by [Formula A] according to the present invention, the substituents R ₅ and R ₆ in the imido ligand are preferably each the same or different and independently of each other, C ₁ -C ₆ linear, branched or cyclic alkyl group; more preferably, each of the same or different and independently from each other, C ₁ -C ₆ linear, branched or cyclic alkyl group; More preferably, the substituents R ₅ and R ₆ may be the same or different and independently of each other, a C ₃ -C ₆ branched or C ₃ -C ₆ cyclic alkyl group; The substituents R ₅ and R ₆ may be the same or different and independently of each other, and may be any one selected from CH(CH ₃ ) ₂ and C(CH ₃ ) ₃ , thereby forming a metal thin film and a metal oxide thin film. It can exhibit further improved volatility and excellent chemical-thermal stability, and a fast deposition rate of thin films even at relatively low temperatures.

In addition, as a preferred embodiment of the present invention, in the organometallic compound represented by [Formula A] according to the present invention, the substituents R ₅ and R ₆ in the imido ligand may be the same as each other.

In addition, in the organometallic compound represented by [Formula A] according to the present invention, an alkoxy thio carboxamide ligand containing the substituents R ₁ and R ₂ and an alkoxy thio carboxamide ligand containing the substituents R ₃ and R ₄ myde The ligands may have the same structure as each other.

In addition, in the organometallic compound represented by [Formula A] according to the present invention, more preferably, the substituents R ₅ and R ₆ in the imido ligand in Formula A are the same, and in this case, the substituents An alkoxy thio carboxamide ligand comprising R ₁ and R ₂ and an alkoxy thio carboxamide comprising substituents R ₃ and R ₄ The ligands may have the same structure as each other.

In addition, the present invention uses the organometallic compound represented by Formula A as a metal precursor to produce a molybdenum-containing thin film, such as a molybdenum metal thin film, a molybdenum oxide thin film, or a molybdenum chalcogenide thin film. A method can be provided, and the present invention can also provide a thin film obtained by the above manufacturing method.

More specifically, the present invention manufactures a molybdenum thin film using the organometallic compound represented by Formula A as a metal precursor; or producing a molybdenum oxide thin film; Alternatively, a method of producing a molybdenum chalcogenide thin film may be provided, and these may be a solution capable of forming a thin film by dissolving and coating a precursor in a chemical vapor deposition (CVD) method or atomic layer deposition (ALD) method or a solvent. It can be performed by a process method.

Here, the chemical vapor deposition (CVD) method, atomic layer deposition (ALD), or solution process appropriately adjusts the growth rate and thin film formation temperature conditions according to each process condition to achieve optimal thickness and density. Branches can produce thin films.

More specifically, when using the chemical vapor deposition (CVD) method, the reactant containing the organometallic compound precursor of the present invention is supplied in a gaseous state to a reactor containing a substrate of various types or shapes, thereby forming a molar layer on the substrate. Lybdenum metal thin films, molybdenum oxide thin films, or molybdenum chalcogenide thin films can be produced, and in this case, the organometallic compound represented by the formula A of the present invention is thermally stable and has good volatility. Therefore, it is possible to manufacture high-quality thin films with the desired shape under various conditions.

In addition, in the present invention, when using atomic layer deposition (ALD), a reactant containing the organometallic compound represented by formula A in the present invention as a precursor is supplied to the deposition chamber in pulse form to form a surface of the wafer. A precise single-layer film can be formed by causing a chemical reaction.

In addition, in the present invention, when forming a thin film of the organic tin compound represented by Formula A by a solution process, the organic tin compound (precursor) is dissolved in a solvent and coated on the substrate, followed by heating or applying energy from the outside. By receiving, a molybdenum metal thin film, a molybdenum oxide thin film, or a molybdenum chalcogenide thin film can be formed.

Meanwhile, the present invention provides a molybdenum compound represented by Compound C below; and a compound represented by Compound D1 and a compound represented by Compound D2, respectively, as reactants to produce an organometallic compound represented by Formula A. A method for producing an organometallic compound represented by the following Formula A: provides.

[Compound C] [Compound D1] [Compound D2]

[Formula A]

In compound C,

R ₇ and R ₈ are the same or different and independently of each other, a C ₁ -C ₁₀ linear, branched or cyclic alkyl group; and a C ₁ -C ₁₀ linear, branched or cyclic halogenated alkyl group,

X ₁ and X ₂ are each the same or different and independently of each other, any halogen element selected from F, Cl and Br,

In Compound C, Compound D1, Compound D2 and Formula A, M, R ₁ to R ₆ are each as defined above,

In the compound A, the imido group containing R ₅ and the imido group containing R ₆ may each face each other with respect to the central atom M or be arranged perpendicularly to each other with respect to the central atom M.

That is, the organometallic compound represented by Formula A of the present invention includes an organometallic compound represented by Compound C, an alkoxy thio carboxamide compound represented by Compound D1, and an alkoxy thio carboxamide represented by Compound D2. Compound; is used as a reactant _, and the two identical _or different halogen elements ( Carboxamide The organometallic compound represented by [Formula A] can be prepared by coordinating the ligand and the alkoxy thio carboxamide ligand containing the substituents R ₃ and R ₄ to a metal (molybdenum) atom.

Here, in the compound C according to the present invention, R ₅ and R ₆ are each preferably the same or different and independently of each other, a C ₁ -C ₆ linear, branched or cyclic alkyl group; It is preferable, more preferably, the same or different and independently of each other, C ₃ -C ₆ branched or cyclic alkyl group; more preferably, the same or different and independently of each other, CH It may be any one selected from (CH ₃ ) ₂ and C(CH ₃ ) ₃ .

In addition, the alkoxy thio carboxamide compound represented by compound D1 and the alkoxy thio carboxamide represented by compound D2 according to the present invention. In the compound, the substituents R ₁ to R ₄ are preferably each the same or different and independently of each other, a C ₁ -C ₆ linear, branched or cyclic alkyl group; more preferably, the substituent R ₁ to R ₄ are each the same or different and independently of each other, CH ₃ , C ₂ H ₅ , CH(CH ₃ ) ₂ , It may be any one selected from nC ₃ H ₈ and C(CH ₃ ) ₃ .

In addition, in a more preferred embodiment of the present invention, the substituents R ₅ and R ₆ in the compound C may each be the same as each other, and an alkoxy thio group comprising the substituents R ₁ and R ₂ represented by the compound D1. Carboxamide compound and alkoxy thio carboxamide containing the above substituents R ₃ to R ₄ Compounds that are the same as each other can be used.

In addition, in a more preferred embodiment of the present invention, an alkoxy thio carboxamide represented by compound D1 according to the present invention Compounds, and an alkoxy thio carboxamide designated as Compound D2 The substituents R ₁ to R ₄ in the compound are preferably each the same or different and independently of each other, a C ₁ -C ₆ linear, branched or cyclic alkyl group; more preferably each is the same or different. And independently of each other, CH ₃ , C ₂ H ₅ , CH(CH ₃ ) ₂ , It may be any one selected from nC ₃ H ₈ and C(CH ₃ ) ₃ .

In addition, in the present invention, in the compound C, R ₅ and R ₆ may be the same or different and independently of each other, a branched or cyclic alkyl group of C ₃ -C ₆ , and the two groups in the compound C may be The halogen elements (X1 and X2) may each preferably be chlorine atoms (Cl).

Meanwhile, when an organic solvent is used in producing the organometallic compound represented by the formula A, suitable types of organic solvents include toluene, tetrahydrofuran, hexane, cyclohexane, diethyl ether, acetonitrile, and dimethyl. formamide Examples include, but are not limited to, tetrahydrofuran.

The reaction may preferably be carried out in the organic solvent at a temperature range of 10 to 40° C. for 12 to 24 hours, and preferably at room temperature (25 ° C. ) for 18 hours. The compound represented by Formula A can be prepared through.

Here, in order to separate the product from the by-products or unreacted products generated during the reaction, sublimation, distillation, extraction, or column chromatography is used to obtain a novel organometallic compound of high purity. You can.

The high-purity organometallic compound represented by Chemical Formula A thus obtained may be solid or liquid at room temperature, and is thermally stable and has good volatility.

Hereinafter, the present invention will be described in more detail with reference to preferred embodiments. However, these examples are for illustrating the present invention in more detail, and it will be apparent to those skilled in the art that the scope of the present invention is not limited thereto.

Preparation Example 1. Mo(NtBu) ₂ (mdpaS) ₂ synthesis of

[Mo(NtBu) ₂ (mdpaS) ₂ ]

mdpaSH (0.294 g, 2 mmol, 1 eq) was dissolved in THF in a round bottom flask and stirred with NaH (0.048 g, 2 mmol, 1 eq) at room temperature for 2 hours. Then, the reaction product was filtered and the by-products were removed under reduced pressure. After removal, a white solid compound was obtained. After adding hexane to this compound, Mo(N ^t Bu) ₂ Cl ₂ (DME) (0.399 g, 1 mmol, 0.5 eq) was added and stirred at room temperature for 18 hours. After the reaction, by-products were removed from the solution obtained under reduced pressure to obtain a brown solid compound. By sublimation under reduced pressure at 65°C, pure [Mo(NtBu) ₂ (mdpaS) ₂ ] compound was obtained as a yellow solid. (0.48 g, yield 90%)

¹ H NMR (400 MHz, C ₆ D ₆ ) δ (ppm): 1.32 (s, 18H, CC(CH ₃ ) ₃ ), 1.43 (s, 18H, NC(CH ₃ ) ₃ ), 4.26 (s, 6H, OCH ₃ ).

¹³ C NMR (100 MHz, C ₆ D ₆ ) δ (ppm): 29.67 (CC(CH ₃ ) ₃ ), 30.00 (NC(CH ₃ ) ₃ ), 39.26 (CC(CH ₃ ) ₃ ), 64.00 (OCH ₃ ), 70.14 (NC(CH ₃ ) ₃ ), 169.67 (CC( CH ₃ ) ₃ ).

Elemental analysis: Anal. Calcd for C ₂₀ H ₄₂ MoN ₄ O ₂ S ₂ : C, 45.27; H, 7.98; N, 10.56; S, 12.08. Found: C, 44.94; H, 7.95; N, 10.42; S, 12.02.

MP: 81.5℃

The Mo(N ^t Bu) ₂ (mdpaS) ₂ compound prepared according to Preparation Example 1 was a solid and had excellent crystallinity, and its X-ray crystal structure was analyzed and shown in FIG. 1.

Preparation Example 2. Mo(N ^t Bu) ₂ (edpaS) ₂ synthesis of

[Mo(N ^t Bu) ₂ (edpaS) ₂ ]

In a round bottom flask, edpaSH (0.322 g, 2 mmol, 1 eq) was dissolved in THF and stirred with NaH (0.048 g, 2 mmol, 1 eq) at room temperature for 2 hours. Then, the reaction product was filtered and the by-product was dissolved under reduced pressure. was removed to obtain a white solid compound. After adding hexane to this compound, Mo(N ^t Bu) ₂ Cl ₂ (DME) (0.399 g, 1 mmol, 0.5 eq) was added and stirred at room temperature for 18 hours. After the reaction, by-products were removed from the solution obtained under reduced pressure to obtain a brown solid compound. By sublimation under reduced pressure at 65°C, pure [Mo(N ^t Bu) ₂ (edpaS) ₂ compound was obtained as a yellow solid. (0.52 g, 94% yield).

¹ H NMR (400 MHz, C ₆ D ₆ ) δ (ppm): 1.33 (s, 18H, CC(CH ₃ ) ₃ ), 1.41 (t, 6H, OCH ₂ CH ₃ ), 1.43 (s, 18H, NC(CH ₃ ) ₃ ), 4.68 (m, 4H, OCH ₂ CH ₃ )

¹³ C NMR (100 MHz, C ₆ D ₆ ) δ (ppm): 14.86 (OCH ₂ CH ₃ ), 29.71 (CC(CH ₃ ) ₃ ), 29.93 (NC(CH ₃ ) ₃ ), 39.37 (CC(CH ₃ ) ₃ ), 70.19 (NC(CH ₃ ) ₃ ), 72.22 (OCH ₂ CH ₃ ), 168.88 (CC(CH ₃ ) ₃ ).

Elemental analysis: Anal. Calcd for C ₂₂ H ₄₆ MoN ₄ O ₂ S ₂ : C, 47.30; H, 8.30; N, 10.03; S, 11.48. Found: C, 45.93; H, 8.21; N, 9.90; S, 11.99.

MP: 70.0℃

Example 1. Analysis of thermal properties of compounds

To measure the thermal stability, volatility, and decomposition temperature of the organometallic compounds (precursors) synthesized in Preparation Examples 1 and 2, thermogravimetric analysis (TGA) was used. The TGA method is to heat the product from 25 ℃ to 600 ℃ at a rate of 10 ℃/min, inject nitrogen gas at a flow rate of 50 ml/min, measure the weight change, and measure the weight change, A TGA graph showing the experimental results of ribdenum precursor compounds is shown in FIG. 2.

Looking at the thermal property analysis according to FIG. 2 in more detail, the molybdenum precursor compound according to Preparation Example 1 experienced a mass reduction of 59% from 150 ° C to 200 ° C, and then lost 18% of the mass from 200 ° C to 370 ° C. A decrease was observed. From the first mass reduction section, decomposition of the compound occurred at low temperature, and a final residual amount of 23% was observed.

In addition, the molybdenum precursor compound according to Preparation Example 2 experienced a 53% mass reduction from 150°C to 180°C, and then a 16% mass reduction was observed from 180°C to 350°C. From the first mass reduction section, decomposition of the compound occurred at low temperature, and a final residual amount of 30% was observed.

According to the TGA analysis results of the compounds prepared according to the present invention, the organometallic compound represented by [Formula A] of the present invention forms molybdenum metal thin films, molybdenum metal oxide thin films, molybdenum sulfide thin films, etc. It can be seen that it has good characteristics for this purpose.

Although the preferred embodiments of the present invention have been described in detail above, the scope of the present invention is not limited thereto, and various modifications and improvements can be made by those skilled in the art using the basic concept of the present invention as defined in the following claims. It falls within the scope of invention rights.

Claims (9)

An organometallic compound represented by the following [Chemical Formula A].
[Formula A]

In Formula A,
The M is molybdenum (Mo),
R ₁ to R ₄ are each the same or different and independently of each other hydrogen, deuterium, C ₁ -C ₁₀ linear, branched or cyclic alkyl group; and a C ₁ -C ₁₀ linear, branched or cyclic halogenated alkyl group,
R ₅ and R ₆ are each the same or different and independently from each other a linear, branched or cyclic alkyl group of C ₁ -C ₁₀ ; and a C ₁ -C ₁₀ linear, branched or cyclic halogenated alkyl group; Any one selected from,
Here, the imido group containing R ₅ and the imido group containing R ₆ may each face each other with respect to the central atom M or be arranged perpendicularly to each other with respect to the central atom M.
According to paragraph 1,
R ₁ to R ₄ are each the same or different and independently of each other a C ₁ -C ₆ linear, branched or cyclic alkyl group; An organometallic compound characterized in that
According to paragraph 2,
Wherein R ₁ to R ₄ are each the same or different and independently of each other, CH ₃ , C ₂ H ₅ , CH(CH ₃ ) ₂ , An organometallic compound characterized in that it is any one selected from nC ₃ H ₈ and C(CH ₃ ) ₃ .
According to paragraph 1,
R ₅ and R ₆ are the same or different and independently of each other, a C ₁ -C ₆ linear, branched or cyclic alkyl group; An organometallic compound characterized in that
According to paragraph 4,
R ₅ and R ₆ are each the same or different and independently of each other a C ₃ -C ₆ branched or cyclic alkyl group; An organometallic compound characterized in that
According to paragraph 1,
The substituents R ₅ and R ₆ in the imido ligand in Formula A are the same as each other; Alkoxy thio carboxamide ligand containing the substituents R ₁ and R ₂ and alkoxy thio carboxamide containing the substituents R ₃ and R ₄ An organometallic compound characterized in that the ligands have the same structure.
A method of producing a molybdenum-containing thin film using the organometallic compound according to any one of claims 1 to 6 as a metal precursor.
In clause 7,
The method of producing the molybdenum-containing thin film is characterized in that it is performed by chemical vapor deposition (CVD) or atomic layer deposition (ALD) or a solution process. .
A molybdenum compound represented by compound C below; and,
A method for producing an organometallic compound represented by the formula A of claim 1, characterized in that the organometallic compound represented by the formula A is prepared by using a compound represented by compound D1 and a compound represented by compound D2 as reactants, respectively. .
[Compound C] [Compound D1] [Compound D2]

[Formula A]

In compound C,
R ₇ and R ₈ are the same or different and independently of each other, a C ₁ -C ₁₀ linear, branched or cyclic alkyl group; and a C ₁ -C ₁₀ linear, branched or cyclic halogenated alkyl group,
X ₁ and X ₂ are each the same or different and independently of each other, any halogen element selected from F, Cl and Br,
Compound C, Compound D1, Compound D2 and M in Formula A, R ₁ to R ₆ are each as defined in paragraph 1,
In the compound A, the imido group containing R ₅ and the imido group containing R ₆ may each face each other with respect to the central atom M or be arranged perpendicularly to each other with respect to the central atom M.