TWI828165B - Organometallic compound, method for synthesizing the same, precursor for vapor deposition containing the same, and method for producing thin film - Google Patents

Abstract

The present invention relates to a method for synthesizing organic metal compounds (especially organic metal compounds containing rare earth metals) and a method for depositing the synthesized organic metal compounds to produce thin films with excellent characteristics.

Description

Organometallic compounds, synthesis methods thereof, vapor deposition precursors containing the same, and methods for producing thin films

The present invention relates to a method for synthesizing an organic metal compound and a method for producing a thin film using the obtained organic metal compound. The aforementioned organic metal compound can be used as a vapor deposition compound capable of achieving thin film deposition by vapor deposition. Specifically, it relates to A method of synthesizing an organic metal compound and a method of forming a thin film using the synthesized organic metal compound. The aforementioned organic metal compound can be applied to atomic layer deposition (Atomic Layer Deposition; ALD) or chemical vapor deposition (Chemical Vapor Deposition; CVD) ), excellent volatility and thermal stability, and excellent reactivity with reaction gases.

Recently, silicon oxide (SiO ₂ ) used as a dielectric material is being replaced by metal gate/high-k transistors due to dense packaging and miniaturized channel lengths of semiconductor components.

In particular, as component sizes are miniaturized, there is a need to develop high-dielectric-constant materials and processes that can apply them.

High-k materials, on the other hand, require high band gaps and band offsets, high k values, excellent stability to the silicon phase, minimal _SiO2 interfacial layer, and high-quality interface on the substrate . In addition, amorphous or high crystallization temperature films are preferred.

Typical high-dielectric materials that are actively researched and applied to replace silicon oxide can include hafnium oxide (HfO ₂ ), etc. Especially in processes below 10nm, a new generation of high-dielectric materials is constantly required. Potential candidates include rare earth-doped hafnium oxide.

In particular, materials containing rare earth elements are promising high-dielectric materials for advanced silicon CMOS, germanium CMOS and III-V transistor components. It is reported that a new generation of oxides based on them has better performance than traditional dielectric materials. Significant capacity advantage.

In addition, materials containing rare earth elements are expected to be used in the manufacture of perovskite materials with strong ferroelectricity, pyroelectricity, piezoelectricity, resistance conversion and other properties. That is, research is underway to manufacture ABO ₃ form perovskites by using a vapor deposition process using organometallic compound precursors, adjusting the types or components of A and B cations (rare earths or transition metals) to impart dielectric properties to the material. Various properties such as electron transport and oxygen ion transport rate are used in various industrial fields such as fuel cells, sensors, and secondary batteries.

In addition, for materials containing rare earth elements, research is also underway to utilize the excellent water permeability resistance of multi-layer oxide film structures for packaging materials or for realizing a new generation of non-volatile memory.

However, it is still difficult to deposit a rare earth-containing layer, so rare earth precursors with various ligands that facilitate deposition have been studied.

Representative examples of ligands constituting rare earth precursors include amide, amidinate, β-Diketonate, cyclopentadienyl (Cp) and other compound groups These precursors have shortcomings such as high melting point, low deposition temperature, high impurities in the film, and low reactivity that are difficult to apply in actual processes.

As a result, there is an urgent need to develop an improved rare earth precursor for the deposition of rare earth-containing thin films, an efficient synthesis method of the rare earth precursor, and a deposition process using the synthesized rare earth precursor.

[Prior technical literature] [Patent Document] Patent Document 1: US Granted Patent No. 8871304.

[Technical Issue]

Therefore, the present invention is used to solve the problems of organometallic compound precursors (especially rare earth precursors) in the prior art, and aims to provide an organometallic compound precursor that is excellent in thermal stability and volatility, and has excellent reactivity with reaction gases. compounds.

In addition, the present invention aims to provide a method for efficiently synthesizing the aforementioned organometallic compound precursor compound and a thin film production method using the synthesized organometallic compound precursor compound.

However, the problems to be solved by the present invention are not limited to the above-mentioned problems, and other problems not mentioned can be clearly understood by those with ordinary knowledge in the technical field from the following description. [Technical solution]

One aspect of the present invention provides a method for synthesizing an organometallic compound, including the step of reacting a compound of Chemical Formula 1 below with a compound of Chemical Formula 2 below to synthesize a compound of Chemical Formula 3 below.

[Chemical Formula 1] ML ₃ [Chemical Formula 2] [Chemical formula 3] In the aforementioned chemical formulas 1 to 3, M is a rare earth element, and L is selected from the group consisting of silyl amine groups, linear or branched alkyl groups with 1 to 4 carbon atoms, and Any one of the group of dialkylamine (dialkylamine) with 2 to 10 carbon atoms, alkoxide group with 1 to 4 carbon atoms, and a reactive group including one or more aromatic rings, R ₁ to R ₃ are each independently Hydrogen, linear or branched chain hydrocarbons with 1 to 4 carbon atoms, x is an integer from 1 to 3.

Another aspect of the present invention provides an organometallic compound represented by the following Chemical Formula 3.

[Chemical formula 3] In the aforementioned Chemical Formula 3, M is a rare earth element, and L is selected from the group consisting of a silyl amine group, a linear or branched alkyl group with 1 to 4 carbon atoms, and alkyl group with 2 to 4 carbon atoms. Any of the group of 10 dialkylamine groups, alkoxide groups having 1 to 4 carbon atoms, and reactive groups including one or more aromatic rings, R ₁ to R ₃ are each independently hydrogen , straight chain or branched chain hydrocarbons with 1 to 4 carbon atoms, x is 1 or 2.

Another aspect of the present invention provides a deposition precursor containing any one or more of the aforementioned organic metal compounds.

Still another aspect of the present invention provides a method for manufacturing a thin film, including the step of introducing the aforementioned vapor deposition precursor into a chamber. [Invention effect]

The method for synthesizing organometallic compounds of the present invention has the effect of enabling efficient synthesis of organometallic compounds.

In addition, using an organic metal compound synthesized by the method of synthesizing an organic metal compound of the present invention to produce a thin film has the effect of providing a thin film with excellent characteristics.

Films with excellent properties produced by the film production method of the present invention can be used in dielectric materials of various electronic devices (especially high-K/metal gates, DRAM capacitors), perovskite materials, display devices, and new generation memories. wait.

The functions and effects of the invention will be described in more detail below through specific embodiments of the invention. However, such embodiments are merely provided as examples of the invention, and the patentable scope of the present invention is not limited thereby.

Prior to this, the terms or words used in this specification and the scope of the patent application shall not be limited to ordinary or dictionary meanings, but shall be based on "the inventor can appropriately define it in order to describe his own invention in the best way." According to the principle of "terminology concept", only the meanings and concepts consistent with the technical ideas of the present invention will be interpreted.

Therefore, the configuration of the embodiments described in this specification is only one of the best embodiments of the present invention, and does not all represent the technical ideas of the present invention. Therefore, it should be understood that there will be various equivalents that can replace them at the time of the present invention. objects and modifications.

Singular expressions used in this specification include plural expressions unless the context clearly indicates otherwise. In this specification, it should be understood that terms such as "including", "having" or "having" specify the presence of implementation features, numbers, steps, components or their combinations, and do not preclude the existence or addition of one or more of them. Possibility of other features, numbers, steps, building blocks or combinations thereof.

A method of synthesizing an organometallic compound according to one aspect of the present invention may include the step of reacting a compound of Chemical Formula 1 with a compound of Chemical Formula 2 to synthesize a compound of Chemical Formula 3.

[Chemical Formula 1] ML ₃ [Chemical Formula 2] [Chemical formula 3] In the aforementioned Chemical Formulas 1 to 3, M is a rare earth element, and L is selected from the group consisting of silyl amine groups, linear or branched alkyl groups with 1 to 4 carbon atoms, and carbon atoms. Any of the group of dialkylamine groups with 2 to 10 carbon atoms, alkoxide groups with 1 to 4 carbon atoms, and reactive groups including one or more aromatic rings, R ₁ to R ₃ are each independent Ground is hydrogen, a linear or branched chain hydrocarbon with 1 to 4 carbon atoms, and x is an integer from 1 to 3.

As a solvent used for the reaction of Chemical Formula 1 and Chemical Formula 2, toluene can be used, and the reaction temperature can be 18°C to 75°C. In particular, the reaction temperature may be normal temperature or about 70°C.

In an implementation example, the aforementioned rare earth elements may be scandium (Sc), yttrium (Y), lanthanum (La), cerium (Ce), phosphorus (Pr), neodymium (Nd), samarium (Sm), europium (Eu) ), Gd, Tb, Dy, Ho, Er, Tm, Yb or Lu,

The aforementioned rare earth element may preferably be lanthanum (La).

In one implementation, L can be benzyl selected from the group consisting of bis(trimethylsilyl)amine; BTSA), unsubstituted or substituted with one or more alkyl groups having 1 to 3 carbon atoms. , and any one of the group consisting of o-toluidine that is unsubstituted or substituted with one or more alkyl groups having 1 to 3 carbon atoms.

In an implementation example, the compound of the aforementioned Chemical Formula 1 may be represented by the following Chemical Formula 1-1 or the following Chemical Formula 1-2.

[Chemical formula 1-1] [Chemical formula 1-2] In the aforementioned Chemical Formula 1-1 and the aforementioned Chemical Formula 1-2, M is scandium (Sc), yttrium (Y), lanthanum (La), cerium (Ce), cerium (Pr), neodymium (Nd), samarium (Sm) , europium (Eu), gallium (Gd), dynamium (Tb), dysprosium (Dy), 鈥 (Ho), erbium (Er), 銩(Tm), ytterbium (Yb) or 鑥 (Lu).

In addition, the compound of the aforementioned chemical formula 2 may be, but is not limited to, NHtBuCH ₂ CH ₂ NMe ₂ , NHtBuCH(Me)CH ₂ NMe ₂ or NHtBuCH ₂ CH ₂ NEt ₂ (tBu represents tert-butyl (tert-butyl), Me represents methane group, Et represents ethyl group).

The organometallic compound according to another aspect of the present invention can be represented by the following Chemical Formula 3.

[Chemical formula 3] In the aforementioned Chemical Formula 3, M is a rare earth element, and L is selected from the group consisting of a silyl amine group, a linear or branched alkyl group with 1 to 4 carbon atoms, and alkyl group with 2 to 4 carbon atoms. Any of the group of 10 dialkylamine groups, alkoxide groups having 1 to 4 carbon atoms, and reactive groups including one or more aromatic rings, R ₁ to R ₃ are each independently hydrogen , straight chain or branched chain hydrocarbons with 1 to 4 carbon atoms, x is 1 or 2.

In an implementation example, the aforementioned rare earth elements may be scandium (Sc), yttrium (Y), lanthanum (La), cerium (Ce), phosphorus (Pr), neodymium (Nd), samarium (Sm), europium (Eu) ), gallium (Gd), terium (Tb), dysprosium (Dy), 鈥 (Ho), erbium (Er), strontium (Tm), ytterbium (Yb) and 鑥 (Lu), L can be selected from Hexamethyldisilazane (bis(trimethylsilyl)amine), unsubstituted or benzyl substituted with one or more alkyl groups having 1 to 3 carbon atoms, and unsubstituted or substituted benzyl groups having 1 to 3 carbon atoms Any of the group consisting of more than one alkyl-substituted o-toluidine.

The aforementioned compound of Chemical Formula 3 can be synthesized according to the aforementioned method for synthesizing organometallic compounds.

Another aspect of the present invention provides a deposition precursor comprising the aforementioned compound, preferably a vapor deposition precursor.

A method for manufacturing a thin film according to yet another aspect of the present invention may include the step of introducing the aforementioned vapor deposition precursor into a chamber. The step of introducing the aforementioned vapor deposition precursor into the chamber may include steps of physical adsorption, chemical adsorption, or physical and chemical adsorption.

In an implementation example, the manufacturing method of the aforementioned thin film may include atomic layer deposition (Atomic Layer Deposition; ALD) or chemical vapor deposition (Chemical Vapor Deposition; CVD).

The manufacturing method of the aforementioned thin film may include, but is not limited to, Metal Organic Chemical Vapor Deposition (MOCVD), Low Pressure Chemical Vapor Deposition (LPCVD), Pulsed DC Chemical Vapor Deposition (PCVD). -CVD), plasma enhanced atomic layer deposition (PE-ALD) or their combination.

In an implementation example, the manufacturing method of the aforementioned thin film may further include: as a reaction gas, injecting compounds containing oxygen (O) atoms, compounds containing nitrogen (N) atoms, compounds containing carbon (C) atoms, and compounds containing silicon (Si) atoms. Any one or more steps in the compound.

In an implementation example, the aforementioned reaction gas may be selected from oxygen (O ₂ ), ozone (O ₃ ), water (H ₂ O), hydrogen peroxide (H ₂ O ₂ ), nitrogen (N ₂ ), and ammonia. (NH ₃ ) and hydrazine (N ₂ H ₄ ).

That is, when the desired rare earth-containing film contains oxygen, the reaction gas may be selected from, but is not limited to, oxygen (O ₂ ), ozone (O ₃ ), water (H ₂ O), and hydrogen peroxide (H ₂ O ₂ ) and any combination of them.

When the desired rare earth-containing film contains nitrogen, the reaction gas may be selected from, but not limited to, nitrogen (N ₂ ), ammonia (NH ₃ ), hydrazine (N ₂ H ₄ ), and any combination thereof.

In addition, the desired rare earth-containing thin film may also contain other metals.

The present invention will be described in more detail below using examples, but the present invention is not limited thereto.

[Example 1] Production of ligand

Manufacturing of NHtBuCH ₂ CH ₂ NMe ₂ ligand

Slowly dissolve 1 eq of 2-Chloro-N,N-dimethylethylamine hydrochloride in 100 mL of water, and slowly add 1 eq of NaOH at 0°C aqueous solution. Then, at the same temperature, 4 eq of t-butylamine was slowly added using a dropping funnel, and stirred at room temperature overnight. After the reaction was completed, 1 eq of NaOH was added and further stirred, and extracted with hexane solvent. After removing water from the organic layer using MgSO ₄ , the solvent was removed under normal pressure and purified. The synthesized NHtBuCH ₂ CH ₂ NMe ₂ is a colorless liquid, and the synthesis yield is 30%.

The obtained chemical structural formula and NMR measurement results of NHtBuCH ₂ CH ₂ NMe ₂ are as follows.

[Chemical structural formula of NHtBuCH ₂ CH ₂ NMe ₂ ]

1H-NMR (400MHz, benzene-D6): δ 1.06 (s, 9H), 2.06 (s, 6H), 2.33 (t, 2H), 2.56 (t, 2H)

Manufacturing of NHtBuCH(Me) _{CH2NMe2 Ligand}

In addition to using Dimethylaminoisopropyl chloride hydrochloride instead of 2-Chloro-N,N-dimethylethylamine hydrochloride, with The NHtBuCH ₂ CH ₂ NMe ₂ ligand was produced in the same manner as the reaction. The synthesized NHtBuCH(Me)CH ₂ NMe ₂ is a colorless liquid, and the synthesis yield is 72%.

The obtained chemical structural formula and NMR measurement results _of NHtBuCH(Me) _CH2NMe2 are as follows.

[Chemical structural formula _of NHtBuCH(Me) _CH2NMe2 ]

1H-NMR (400MHz, benzene-D6): δ 0.79 (d, 3H), 1.09 (s, 9H), 2.07 (s, 6H), 2.40 (dd, 1H), 2.51 (dd, 1H), 2.69 (m, 1H)

Manufacturing of NHtBuCH ₂ CH ₂ NEt ₂ ligand

In addition to using 2-chloro-N,N-diethylethylamine hydrochloride (2-Chloro-N,N-diethylethylamine hydrochloride) instead of 2-chloro-N,N-dimethylethylamine hydrochloride (2- In addition to Chloro-N,N-dimethylethylamine hydrochloride), to The NHtBuCH ₂ CH ₂ NMe ₂ ligand was produced in the same manner as the reaction. The synthesized NHtBuCH ₂ CH ₂ NEt ₂ is a colorless liquid, and the synthesis yield is 80%.

The obtained chemical structural formula and NMR measurement results of NHtBuCH ₂ CH ₂ NEt ₂ are as follows.

[Chemical structural formula of NHtBuCH ₂ CH ₂ NEt ₂ ]

1H-NMR (400MHz, benzene-D6): δ 0.96 (t, 6H), 1.09 (s, 9H), 2.40 (q, 4H), 2.50 (t, 2H), 2.59 (t, 2H)

[Example 2] Production of trialkyl lanthanum

[Example 2-1] Production of La (N,N-dimethylo-toluidine) ₃

Synthesis of K (N,N-dimethyl o-toluidine)

Under an ice bath, add solvent THF to a flask containing 1 eq of KOtBu, and then add 1 eq of N,N-dimethyl-o-toluidine. At -78°C, 1 eq of nBuLi was added using a dropping funnel. After stirring for 2 hours, a solid was obtained under reduced pressure. The obtained solid was redissolved in toluene and filtered, and the filtered product was decompressed. The obtained solid was dried, and K (N,N-dimethyl-o-toluidine) was synthesized. The synthesized K (N,N-dimethyl-o-toluidine) is a dark red solid, and the synthesis yield is 100%.

The NMR measurement results of the synthesized K (N,N-dimethyl-o-toluidine) are shown below.

1H-NMR (400MHz, THF-d8): δ 1.83 (s, 1H), 2.42 (s, 1H), 2.50 (s, 6H), 4.91 (t, 1H), 5.89 (d, 1H), 5.96 (t ,1H),6.08(d,1H)

La (N,N-dimethyl o-toluidine) ₃ synthesis

Under an ice bath, add the solvent THF to the flask containing 1 eq of LaBR ₃ THFx, and then slowly add 1 eq of the synthesized K (N,N-dimethylo-toluidine). After stirring for 1 hour, the solvent was removed under reduced pressure. After redissolving in toluene, the precipitate was removed using a filter. The filtrate was then decompressed to obtain La (N,N-dimethyl o-toluidine) ₃ .

The synthesized La (N,N-dimethyl o-toluidine) ₃ is a yellow solid, and the synthesis yield is 38%.

The chemical structural formula and NMR measurement results of the synthesized La(N,N-dimethylo-toluidine) ₃ are as follows.

[Chemical structural formula of La(N,N-dimethylo-toluidine) ₃ ]

1H-NMR (400MHz, C6D6): δ 2.05 (s, 8H), 6.51 (t, 1H), 6.9 (m 3H)

[Example 2-2] Production of La (benzyl) ₃

K (benzyl) synthesis

Under an ice bath, add the solvent THF to a flask containing 1 eq of KOtBu, and then add 1 eq of toluene. At -78°C, 1 eq of nBuLi was added using a dropping funnel. After stirring for 2 hours, a solid was obtained under reduced pressure. The solid obtained was washed with hexane several times and then dried to synthesize K (benzyl). The synthesized K (benzyl) is a red solid, and the synthesis yield is 95%.

The NMR measurement results of the synthesized K (benzyl) are as follows.

1H-NMR (400MHz, THF-d8): δ 2.18 (s, 2H), 4.65 (t, 1H), 5.50 (d, 2H), 5.98 (t, 2H)

La (benzyl) ₃ synthesis

Under an ice bath, add the solvent THF to the flask containing 1 eq of LaBR ₃ THF _x , and slowly add 1 eq of the synthesized K (benzyl). Stir for 1 hour and then filter to remove the precipitate. The filtrate was then decompressed to obtain La (benzyl) ₃ . The synthesized La (benzyl) ₃ was a dark red solid, and the synthesis yield was 47%.

The chemical structural formula and NMR measurement results of the synthesized La(benzyl) ₃ are as follows.

[Chemical structural formula of La (benzyl) ₃ ]

1H-NMR (400MHz, C6D6): δ 1.25 (s, 2H), 5.78 (s, 2H), 6.06 (t, 1H), 6.66 (t, 2H)

[Example 3] Production of La(NHtBuCH ₂ CH ₂ NMe ₂ ) ₃

At room temperature _, add _the solvent toluene ( Toluene), then add 3 eq of NHtBuCH ₂ CH ₂ NMe ₂ from Example 1 and stir at room temperature overnight. After the reaction was completed, it was concentrated under reduced pressure, sublimated and purified at 110°C and 56 m Torr to obtain La(NHtBuCH ₂ CH ₂ NMe ₂ ) ₃ . The synthesized La(NHtBuCH ₂ CH ₂ NMe ₂ ) ₃ is an ivory solid, and the synthesis yield is 15%.

The chemical structural formula and NMR measurement results of the synthesized La(NHtBuCH ₂ CH ₂ NMe ₂ ) ₃ are as follows.

[Chemical structural formula of La(NHtBuCH ₂ CH ₂ NMe ₂ ) ₃ ]

In the aforementioned chemical structural formula of La(NHtBuCH ₂ CH ₂ NMe ₂ ) ₃ , tBu is tert-butyl.

1H-NMR (400MHz, C6D6): δ 1.42 (s, 27H), 2.1 (s, 18H), 2.54 (t, 6H), 3.16 (t, 6H)

[Example 4] Production of La(btsa)2(NHtBuCH ₂ CH ₂ NMe ₂ )

After adding solvent toluene (Toluene) to the flask containing 1 eq of La(btsa) ₃ , add 1 eq of NHtBuCH ₂ CH ₂ NMe ₂ of Example 1. Heat at 70°C overnight. After the reaction was completed, it was concentrated under reduced pressure, and sublimated and purified at 110°C and 56 m Torr to obtain La(btsa)2(NHtBuCH ₂ CH ₂ NMe ₂ ).

The synthesized La(btsa) 2 (NHtBuCH ₂ CH ₂ NMe ₂ ) is an ivory solid, and the synthesis yield is 76%.

The chemical structural formula and NMR _{measurement results} of the synthesized La(btsa)2( _{NHtBuCH2CH2NMe2} ) are as follows.

[Chemical structural formula of La(btsa)2(NHtBuCH ₂ CH ₂ NMe ₂ )]

In the aforementioned chemical structural formula of La(btsa) 2 (NHtBuCH ₂ CH ₂ NMe ₂ ), BTSA is hexamethyldisilazane (bis(trimethylsilyl)amine), and tBu is tert-butyl.

1H-NMR (400MHz, THF-d8):

δ 0.15 (s, 36H), 1.23 (s, 9H), 2.48 (s, 6H), 3.03 (t, 2H), 3.09 (t, 2H)

[Experimental example]

The thermogravimetric analysis results of the compounds of Example 3 and Example 4 are shown in Figure 1.

According to the thermogravimetric analysis results, the temperature at which the weight is reduced by half [T1/2] was measured and showed that the compound of Example 3 was 243°C and the compound of Example 4 was 257°C.

In addition, the residue amount measurement at 400°C showed that the compound of Example 3 was 44% by weight and the compound of Example 4 was 29.4% by weight.

[Manufacturing Example 1]

The precursor and reactant O ₃ synthesized in Example 3 and Example 4 of the present invention are alternately used to deposit a rare earth thin film on the substrate. The substrate used in this experiment is a p-type Si wafer with a resistance of 0.02Ω·m. Before deposition, the p-type Si wafer was cleaned by ultrasonic treatment (Ultra sonic) in acetone-ethanol-deionized water (DI water) for 10 minutes each. The natural oxide film formed on the Si wafer is removed after soaking in a 10% HF (HF:H ₂ O = 1:9) solution for 10 seconds.

The substrate is kept at a temperature of 150-450°C for standby, and the precursors of the aforementioned Examples 3 and 4 are vaporized in a bubbler maintained at a temperature of 90-150°C.

As a purge gas, argon (Ar) was supplied to purge the precursor and reaction gas remaining in the deposition chamber, and the flow rate of argon was 1000 sccm. The reaction gas uses ozone (O ₃ ) with a concentration of 224 g/cm3. Each reaction gas is injected by adjusting the on/off of the pneumatic valve to form a film at the process temperature.

The ALD cycle sequentially included a 10/15 sec precursor pulse, a 10 sec argon purge, a 2/5/8/10 sec reactant pulse, and a 10 sec argon purge. The deposition chamber pressure is adjusted to 1-1.5 Torr, and the deposition temperature is adjusted to 150-450°C.

It was confirmed that a lanthanum oxide thin film was formed using the compounds of Example 3 and Example 4 as a precursor.

[Manufacturing Example 2]

Using the precursor synthesized in Example 3 and Example 4 of the present invention, a thin film containing rare earth elements was produced by chemical vapor deposition. A starting precursor solution containing the precursors synthesized in Examples 3 and 4 was prepared.

The starting precursor solution was delivered at a flow rate of 0.1 cc/min into a vaporizer maintained at a temperature of 90-150°C. Use 50 to 300 sccm of helium carrier gas to deliver the vaporized precursor to the deposition chamber. Hydrogen (H2) and oxygen (O ₂ ) are used as reaction gases, and are supplied to the deposition chamber at a flow rate of 0.5 L/min (0.5pm) respectively. The pressure of the deposition chamber was adjusted from 1 to 15 Torr, and the deposition temperature was adjusted from 150 to 450°C. The deposition process is carried out under these conditions for about 15 minutes.

It was confirmed that a lanthanum oxide thin film could be formed using the compounds of Examples 3 and 4 as precursors.

Through the above thin film production, it can be confirmed that the rare earth precursors synthesized in Examples 3 and 4 can form thin films with excellent performance through CVD and ALD.

That is, a film with uniform characteristics can be produced, and excellent film characteristics, thickness, and misaligned coating properties can be ensured.

Compared with the foregoing detailed description, the scope of the present invention is represented by the patent claims described below. The meaning and scope of the claims and all changes or deformations derived from the concept of equivalents should be construed as being included in the scope of the present invention.

without

Figure 1 is a graph of thermogravimetric (TG) analysis results of the compounds of Example 3 and Example 4 of the present invention.

Claims (11)

A method for synthesizing an organometallic compound, including the step of reacting a compound of the following Chemical Formula 1 with a compound of the following Chemical Formula 2 to synthesize a compound of the following Chemical Formula 3, [Chemical Formula 1] ML ₃

In the aforementioned Chemical Formulas 1 to 3, M is a rare earth element, and L is selected from the group consisting of silane amines, linear or branched alkyl groups with 1 to 4 carbon atoms, and dialkyl amines with 2 to 10 carbon atoms. , any one of the group of alkoxides with 1 to 4 carbon atoms and reactive groups including one or more aromatic rings, R ₁ to R ₃ are each independently hydrogen, linear or branched chain type with 1 to 4 carbon atoms Hydrocarbon. Any of 3 o-toluidines substituted by more than one alkyl group. The method for synthesizing an organic metal compound as described in claim 1, wherein the rare earth elements are scandium (Sc), yttrium (Y), lanthanum (La), cerium (Ce), cerium (Pr), and neodymium (Nd) , Samarium (Sm), Europium (Eu), Gd (Gd), Tb (Tb), Dysprosium (Dy), Ho (Ho), Erbium (Er), Tm (Tm), Ytterbium (Yb) and Lu (Lu) Any of them. The method for synthesizing an organic metal compound as described in claim 1, wherein L is hexamethyldisilazane. The method for synthesizing an organic metal compound as claimed in claim 1, wherein the compound of the aforementioned Chemical Formula 1 is represented by the following Chemical Formula 1-1 or the following Chemical Formula 1-2,

In the aforementioned Chemical Formula 1-1 and the aforementioned Chemical Formula 1-2, M is scandium (Sc), yttrium (Y), lanthanum (La), cerium (Ce), cerium (Pr), neodymium (Nd), samarium (Sm) , Europium (Eu), Gd (Gd), Tb (Tb), Dysprosium (Dy), Ho (Ho), Erbium (Er), Tm (Tm), Ytterbium (Yb) and Lu (Lu). An organic metal compound represented by the following chemical formula 3,

In the aforementioned chemical formula 3, M is a rare earth element, and L is selected from the group consisting of silane amines, linear or branched alkyl groups with 1 to 4 carbon atoms, dialkyl amines with 2 to 10 carbon atoms, and carbon atoms. Any of the group of alkoxides with numbers 1 to 4 and reactive groups including one or more aromatic rings, R ₁ to R ₃ are each independently hydrogen, a linear or branched chain hydrocarbon with 1 to 4 carbon atoms, x is 1 or 2. The organometallic compound of claim 5, wherein in the aforementioned chemical formula 3, the aforementioned rare earth elements are scandium (Sc), yttrium (Y), lanthanum (La), cerium (Ce), phosphorus (Pr), neodymium (Nd), samarium (Sm), europium (Eu), gallium (Gd), terium (Tb), dysprosium (Dy), 鈥 (Ho), erbium (Er), ternary (Tm), ytterbium (Yb) and 鑥Any of (Lu), L is a benzyl group selected from the group consisting of hexamethyldisilazane, unsubstituted or substituted with one or more alkyl groups having 1 to 3 carbon atoms, and unsubstituted or substituted with one or more alkyl groups having 1 to 3 carbon atoms. Any of the group consisting of more than one alkyl-substituted o-toluidine. A compound containing any one or more of the organometallic compounds described in claim 5 or 6 Vapor deposition precursors. A method for manufacturing a thin film, including the step of introducing the vapor deposition precursor as described in claim 7 into a chamber. The method of manufacturing a thin film according to claim 8, wherein the manufacturing method of the thin film includes an atomic layer deposition method or a chemical vapor deposition method. The method for manufacturing a thin film according to claim 8, further comprising: as a reaction gas, injecting a compound containing oxygen (O) atoms, a compound containing nitrogen (N) atoms, a compound containing carbon (C) atoms, and a compound containing silicon (Si) Any one or more steps in atomic compounds. The method for manufacturing a thin film according to claim 10, wherein the reaction gas is selected from the group consisting of oxygen (O ₂ ), ozone (O ₃ ), water (H ₂ O), hydrogen peroxide (H ₂ O ₂ ), and nitrogen. (N ₂ ), ammonia (NH ₃ ), and hydrazine (N ₂ H ₄ ).