CN113387980A - Preparation method and application of niobium-containing metal organic compound - Google Patents

Preparation method and application of niobium-containing metal organic compound Download PDF

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CN113387980A
CN113387980A CN202110750674.3A CN202110750674A CN113387980A CN 113387980 A CN113387980 A CN 113387980A CN 202110750674 A CN202110750674 A CN 202110750674A CN 113387980 A CN113387980 A CN 113387980A
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niobium
organic compound
containing metal
temperature
stirring
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胡昌锞
张学奇
唐超
朱思坤
李建恒
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Hefei Ande Keming Semiconductor Technology Co ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
    • C07F9/005—Compounds of elements of Group 5 of the Periodic System without metal-carbon linkages
    • C—CHEMISTRY; METALLURGY
    • C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
    • C23C16/00—Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes
    • C23C16/22—Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes characterised by the deposition of inorganic material, other than metallic material
    • C23C16/30—Deposition of compounds, mixtures or solid solutions, e.g. borides, carbides, nitrides
    • C23C16/40—Oxides
    • C23C16/405—Oxides of refractory metals or yttrium
    • C—CHEMISTRY; METALLURGY
    • C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
    • C23C16/00—Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes
    • C23C16/44—Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes characterised by the method of coating
    • C23C16/455—Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes characterised by the method of coating characterised by the method used for introducing gases into reaction chamber or for modifying gas flows in reaction chamber
    • C23C16/45523—Pulsed gas flow or change of composition over time
    • C23C16/45525—Atomic layer deposition [ALD]
    • C23C16/45553—Atomic layer deposition [ALD] characterized by the use of precursors specially adapted for ALD

Abstract

The invention discloses a preparation method of a niobium-containing metal organic compound, which specifically comprises the following steps: s1, mixing NbCl5Dispersing in toluene, adding a small amount of ether, and obtaining a system I after the solid is completely dissolved; s2, cooling the system I, and slowly dropwise adding HNR into the system I2R3After the dropwise addition, the temperature is recovered to room temperature and the stirring is continued to form a body system II; s3, controlling the temperature of the system II, and slowly dripping R into the system II1NH2Stirring to form a system III; s4, lowering the temperature of the system III, and slowly adding R into the system III4Li, stirring to form a system IV; s5, filtering and concentrating the system IV to obtain a system V; s6, washing the system V with a non-polar solvent, extracting, filtering, concentrating, and distilling under reduced pressure to obtain a crude product R1N＝Nb(NR2R3)3And rectifying and purifying to obtain the niobium-containing metal organic compound. The preparation method has the advantages of high yield, short reaction time and simple steps, and avoids using pyridine raw materials with high toxicity.

Description

Preparation method and application of niobium-containing metal organic compound
Technical Field
The invention relates to the field of semiconductor materials, in particular to a preparation method and application of a niobium-containing metal organic compound.
Background
Nb2O5The high-refractive-index optical fiber has a wide bandwidth (3.6 eV), a high refractive index (2.4) and a high dielectric constant (29-200). Thus, Nb2O5Can be widely applied to capacitor dielectric layers, antireflection films, catalyst support oxides and the like. Especially in DRAM applications, Nb2O5There is a growing interest in replacing the widely recognized SrTiO with higher dielectric constant3Or TiO doped with Al2A film. This is because rutile-structure TiO having a higher dielectric constant2Ruthenium and ruthenium oxide need to be matched as electrodes, which leads to increased cost; and SrTiO3Strict control of the stoichiometric ratio is required to achieve higher dielectric constants. In a new generation of DRAM applications, Nb2O5Also as doping material, ZrO is doped2The dielectric layer is used as a main body for adjusting and optimizing the electrical performance.
A series of Nb-containing organometallic compound precursors have been developed to achieve high quality Nb2O5Atomic Layer Deposition (ALD). Such precursor products include:tBuN＝Nb(NEt2)3【TBTDEN】，tBuN＝Nb(NEtMe)3【TBTEMN】，tamylN＝Nb(OtBu)3and the like. Wherein the content of the first and second substances,tBuN＝Nb(NEt2)3，tBuN＝Nb(NEtMe)3has been demonstrated as a liquid precursor material with a better vapor pressure, with a wider ALD window; the decomposition temperature can reach more than 325 ℃. It has also been reported that TBTDEN and TBTEMN are used to deposit low resistivity NbN thin films (2010 semiconductor. Sci. Technol. 25075009; Journal of vacuum Science)&Technology a35,01B143(2017)), a similar precursor molecule formula can be written as: r1N＝Nb(NR2R3)3Wherein R is1Examples thereof include ethyl (Et), n-propyl (nPr), isopropyl (iPr), n-butyl (nBu), sec-butyl (sec-Bu), and tert-butyl (t-Bu), R2/R3Methyl (Me), ethyl (Et), etc. may be mentioned.
The preparation of niobium-containing organometallic compounds has been reported as follows (Dalton trans.,2008, 3715-:
Figure BDA0003146133370000021
Figure BDA0003146133370000022
this process involves the use of large amounts of pyridine (which is highly toxic); step-by-step reaction is needed, the separation of switching solvents (toluene and n-hexane) and intermediate products is involved, the steps are complex, and the reaction time is long; the yield was low (28% or less). Does not meet the requirement of mass production. Therefore, it is necessary to find a new preparation method to improve the yield, shorten the reaction time, simplify the steps, and avoid using the highly toxic raw materials.
Disclosure of Invention
In order to solve the above-mentioned drawbacks of the background art, the present invention provides a method for preparing a niobium-containing organometallic compound, which has high yield, short reaction time, simple steps, and avoids using pyridine raw material with high toxicity, and an application thereof.
The purpose of the invention can be realized by the following technical scheme:
a preparation method of niobium-containing metal organic compound comprises the following chemical reaction general formula:
Figure BDA0003146133370000023
the method specifically comprises the following steps:
s1, mixing NbCl5Dispersing in toluene, adding a small amount of ether, and obtaining a system I after the solid is completely dissolved;
s2, cooling the system I, and slowly dropwise adding HNR into the system I2R3After the dropwise addition, the temperature is recovered to room temperature and the stirring is continued to form a body system II;
s3, controlling the temperature of the system II, and slowly dripping R into the system II1NH2After the dropwise addition, the stirring is recovered to room temperature, and a formation system III is formed;
s4, cooling the system III, and slowly adding R into the system III4Li, after the dripping is finished, naturally recovering the room temperature and stirring to form a body system IV;
s5, filtering and concentrating the system IV to obtain a system V;
s6, washing the system V with a non-polar solvent, extracting, filtering, concentrating, and distilling under reduced pressure to obtain a crude product R1N＝Nb(NR2R3)3And rectifying and purifying to obtain the niobium-containing metal organic compound.
In a further preferred embodiment of the present invention, the ether in step S1 is selected from tetrahydrofuran, diethyl ether, 1, 4-dioxane, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, etc., and the volume ratio of the ether to toluene is 1: 1-100.
As a further preferable aspect of the present invention, HNR in step S22R3Dimethylamine, diethylamine, methylethylamine or other secondary amines.
As a further preferable mode of the present invention, R in step S31NH2Is n-propylamine, isopropylamine, n-butylamine, isobutylamine, sec-butylamine, tert-butylamine or other primary amines.
As a further preferable mode of the present invention, R in step S44Li is methyl lithium, n-butyl lithium, t-butyl lithium or other alkyl lithium.
In a further preferred embodiment of the present invention, the nonpolar solvent in step S6 is one of n-pentane, n-hexane, cyclohexane, n-heptane, n-octane, and cyclooctane.
As a further preferred embodiment of the present invention, system I is cooled to 20 ℃ in step S2Then HNR was added dropwise2R3And in the step S3, the temperature of the system II is controlled to be less than 20 ℃, and R is dropwise added1NH2In the step S4, the system III is cooled to below-10 ℃ and then R is added4Li。
Niobium-containing metal organic compound in Nb2O5The application in atomic layer deposition, the metal organic compound containing niobium is prepared by the method.
The invention has the beneficial effects that:
the preparation method of the niobium-containing metal organic compound adopts a one-pot method, does not need to switch solvents, does not need to separate intermediate products, has simple steps and greatly shortens the total reaction time; the method has high yield, the yield is improved to more than 60 percent from the traditional method of less than 30 percent, and the method is convenient for large-scale production. Meanwhile, the method avoids using pyridine raw materials with high toxicity, and greatly reduces the harm to human bodies and the environment.
Drawings
The invention will be further described with reference to the accompanying drawings.
FIG. 1 is a H-NMR spectrum of a niobium-containing metal organic compound prepared in example 1 of the present invention.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the drawings in the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
In the description of the present invention, it is to be understood that the terms "opening," "upper," "lower," "thickness," "top," "middle," "length," "inner," "peripheral," and the like are used in an orientation or positional relationship that is merely for convenience in describing and simplifying the description, and do not indicate or imply that the referenced component or element must have a particular orientation, be constructed and operated in a particular orientation, and thus should not be considered as limiting the present invention.
Example 1
A preparation method of niobium-containing metal organic compound comprises the following chemical reaction formula:
Figure BDA0003146133370000051
the method specifically comprises the following steps:
(1) in a glove box, 56.3g of niobium pentachloride (NbCl) was weighed5) Adding the mixture into a 2L three-neck flask;
(2) adding 600ml of dried toluene to obtain a dark brown mixed solution, adding 150ml of dried tetrahydrofuran (the volume ratio of toluene to tetrahydrofuran is 4:1) into the mixed solution, immediately turning the system red to obtain a red clear solution (system I), stirring, and cooling the system I to 0 ℃;
(3) slowly dripping 61g of diethylamine into the system I, controlling the temperature of the reaction liquid to be always lower than 0 ℃, gradually increasing the color of the reaction liquid after the reaction liquid turns yellow, and recovering the room temperature after the dripping is finished and continuously stirring for 2 hours to obtain a mixed system II with a blackish color;
(4) weighing 15.24g of tert-butylamine, slowly adding into the system II in a dropwise manner, controlling the temperature to be not higher than 20 ℃, stirring at room temperature for 2 hours after the dropwise addition is finished to obtain a system III, wherein the system III has less solid and is black compared with the system II;
(5) cooling the system III to below-50 ℃, slowly adding 500ml n-butyl lithium n-hexane solution (2.5mol/L) into the system III, gradually deepening the system color, naturally recovering the room temperature after the dropwise addition, and stirring for about 12 hours to obtain brown suspension (system IV);
(6) after the reaction is finished, filtering to obtain a white filter cake, washing with 100mL of n-hexane, and collecting filtrate;
(7) under the protection of nitrogen, heating the system to 80 ℃, and distilling under reduced pressure to remove solvents such as toluene, normal hexane, tetrahydrofuran and the like to obtain a concentrated system V;
(8) transferring the concentrated system V to a glove box, dissolving with 200mL of n-hexane, performing suction filtration again to obtain a white filter cake, and collecting filtrate;
(9) heating to 60 ℃ under the protection of nitrogen, distilling under reduced pressure to remove the solvent, heating to 140 ℃, and distilling under reduced pressure to obtain 57.1g of yellow crude product, wherein the product yield is 72% by calculation;
(10) and carrying out reduced pressure rectification on the crude product to obtain an electronic grade product with the metal purity of more than 99.9999%.
The H-NMR spectrum of the product is shown in FIG. 1. In the spectrum, the chemical shift at 1.15 is terminal methyl H on an ethyl, and the number of H is 18; the chemical shift of the compound at 3.45 is methylene H on an ethyl, and the number of the H is 12; chemical shift at 1.40 is terminal methyl group H on t-butyl, number of H is 9. This demonstrated that the product was tris (diethylamino) (tert-butylimino) niobium (TBTDEN), which took about 30 hours overall.
Example 2
A preparation method of niobium-containing metal organic compound comprises the following chemical reaction formula:
Figure BDA0003146133370000061
the method specifically comprises the following steps:
(1) weighing niobium pentachloride (NbCl) in a glove box5)99.92g, adding into a 2L three-neck flask;
(2) adding 1.2L of refined toluene, making the mixture dark brown red, adding 300ml of refined tetrahydrofuran (the volume ratio of toluene to tetrahydrofuran is 4:1), immediately turning red and obviously releasing heat, and cooling the system to-5 ℃ to obtain a system I;
(3) weighing 87.5g of methyl ethylamine, slowly adding into the reaction system I, maintaining the temperature of the system to be lower than 10 ℃, slowly recovering to room temperature (about 20 ℃) after finishing dripping, and reacting for 2 hours, wherein the color is dark brown black (system II);
(4) weighing 27.05g of tert-butylamine, slowly adding the tert-butylamine into the system II in a dropwise manner, controlling the temperature to be not higher than 15 ℃, reacting for 2 hours after the dropwise addition is finished, and changing the color of reaction liquid from dark black to brownish red and then to brownish yellow (system III);
(5) cooling the system III to-60 ℃, taking 887ml of n-butyllithium solution (2.5mol/L of n-hexane solution), slowly adding the n-butyllithium solution into the system III, gradually turning the reaction liquid into black, then gradually turning the reaction liquid into brown, and recovering the room temperature to react for about 12 hours (system IV) after the dropwise addition is finished;
(6) after the reaction is finished, filtering to obtain a white filter cake, washing with 200mL of n-hexane, and collecting filtrate;
(7) under the protection of nitrogen, heating the system to be not more than 100 ℃, and removing solvents such as toluene, normal hexane, tetrahydrofuran and the like by reduced pressure distillation to obtain a concentrated system V;
(8) transferring the concentrated system V to a glove box, dissolving with 250mL of n-hexane, performing suction filtration again to obtain a white filter cake, and collecting filtrate;
(9) heating to 60 deg.C under nitrogen protection, distilling under reduced pressure to remove solvent, and collecting the distillate (heating temperature 135 deg.C, 0.58mbar) to obtain 82.9g brown yellow liquid with yield of 66%.
Comparative example 1
The reported method was used to prepare niobium-containing organometallic compounds (Dalton trans.,2008, 3715-:
(1) 42g (0.152mol) of niobium pentachloride (NbCl) are weighed in a glove box5) Adding the mixture into a 2L three-neck flask;
(2) adding 2.40L of dried toluene to obtain a dark brown mixed solution, adding 600ml of dried tetrahydrofuran to the mixed solution to immediately turn red to obtain a red clear solution, stirring, and cooling to 0 ℃;
(3) to the mixture was added 28ml (0.54mol) of trimethylchlorosilane (Me)3SiCl) and 38ml of tert-butylamine (0.44mol), to which 44ml of pyridine (0.54mol) and 1.60L of toluene were added with continued stirring and stirred overnight (12 h);
(4) filtering, distilling the filtrate at 80 deg.C under reduced pressure, concentrating, and recrystallizing the concentrated system at-15 deg.C in inert environment to obtain 42g of crystal (a)tBuN)NbCl3py2According to NbCl5The calculated yield is 65 percent in the step;
(5) preparing diethylamine lithium: dissolving 37.1g (0.5mol) of diethylamine in 1L of n-hexane, cooling to below 0 ℃, slowly adding 195ml of 2.5mol/L n-butyllithium-n-hexane solution, continuously stirring and naturally returning to room temperature;
(6) dissolving 42g of the crystal obtained in the step 4 in 1.2L of n-hexane, cooling to 0 ℃, slowly adding a mixed solution of diethylaminolithium-n-hexane into the crystal, gradually changing the system into brown, naturally heating to room temperature, and stirring overnight (12 h);
(7) the system was filtered, the solvent (n-hexane) was removed at 60 ℃ and distilled under reduced pressure to give 10.7g of a yellow viscous liquid, the conversion of this step was 28%, the yield of step 4 was combined, the overall conversion was 18.2%, and it took about 2 days (48 h).
Comparative example 1 and comparative example 1 according to the reported procedure, 1.49kg of NbCl was required to produce 1mol of crude product5142L of toluene, 21.3L of tetrahydrofuran, 2.09kg of trimethylchlorosilane, 1.35L of tert-butylamine, 142.2ml of pyridine, 1.32kg of diethylamine, 6.93L of butyllithium in n-hexane, 78.2L of n-hexane.
Preparation of 1mol of crude TBTDEN according to the procedure of example 1 requires 375g of NbCl54L of toluene, 1L of tetrahydrofuran, 406g of diethylamine, 101g of tert-butylamine, 3.33L of butyllithium in n-hexane, 2L of n-hexane.
Therefore, the preparation method of the niobium-containing metal organic compound has high yield (more than 60 percent), greatly shortens the reaction time, has simple steps and avoids using pyridine raw materials with higher toxicity.
In the description herein, references to the description of "one embodiment," "an example," "a specific example" or the like are intended to mean that a particular feature, structure, material, or characteristic described in connection with the embodiment or example is included in at least one embodiment or example of the invention. In this specification, the schematic representations of the terms used above do not necessarily refer to the same embodiment or example. Furthermore, the particular features, structures, materials, or characteristics described may be combined in any suitable manner in any one or more embodiments or examples.
The foregoing shows and describes the general principles, essential features, and advantages of the invention. It will be understood by those skilled in the art that the present invention is not limited to the embodiments described above, which are described in the specification and illustrated only to illustrate the principle of the present invention, but that various changes and modifications may be made therein without departing from the spirit and scope of the present invention, which fall within the scope of the invention as claimed.

Claims (8)

1. A preparation method of niobium-containing metal organic compound is characterized in that the chemical reaction formula is as follows:
Figure FDA0003146133360000011
the method specifically comprises the following steps:
s1, mixing NbCl5Dispersing in toluene, adding a small amount of ether, and obtaining a system I after the solid is completely dissolved;
s2, cooling the system I, and slowly dropwise adding HNR into the system I2R3After the dropwise addition, the temperature is recovered to room temperature and the stirring is continued to form a body system II;
s3, controlling the temperature of the system II, and slowly dripping R into the system II1NH2After the dropwise addition, the stirring is recovered to room temperature, and a formation system III is formed;
s4, cooling the system III, and slowly adding R into the system III4Li, after the dripping is finished, naturally recovering the room temperature and stirring to form a body system IV;
s5, filtering and concentrating the system IV to obtain a system V;
s6, washing the system V with a non-polar solvent, extracting, filtering, concentrating, and distilling under reduced pressure to obtain a crude product R1N＝Nb(NR2R3)3And rectifying and purifying to obtain the niobium-containing metal organic compound.
2. The method of claim 1, wherein the ether in step S1 is selected from tetrahydrofuran, diethyl ether, 1, 4-dioxane, ethylene glycol dimethyl ether, and diethylene glycol dimethyl ether, and the volume ratio of the ether to toluene is 1: 1-100.
3. The method of claim 1, wherein the HNR in step S2 is selected from the group consisting of2R3Dimethylamine, diethylamine, methylethylamine or other secondary amines.
4. The method for producing a niobium-containing metal-organic compound according to claim 1, wherein R in the step S31NH2Is n-propylamine, isopropylamine, n-butylamine, isobutylamine, sec-butylamine, tert-butylamine or other primary amines.
5. The method for producing a niobium-containing metal-organic compound according to claim 1, wherein R in the step S44Li is methyl lithium, n-butyl lithium, t-butyl lithium or other alkyl lithium.
6. The method of claim 1, wherein the non-polar solvent in step S6 is one of n-pentane, n-hexane, cyclohexane, n-heptane, n-octane, and cyclooctane.
7. The method of claim 1, wherein in step S2, HNR is added dropwise after cooling system I to below 20 ℃2R3And in the step S3, the temperature of the system II is controlled to be less than 20 ℃, and R is dropwise added1NH2In the step S4, the system III is cooled to below-10 ℃ and then R is added4Li。
8. Niobium-containing metal organic compound in Nb2O5Use in atomic layer deposition, wherein the niobium containing metalorganic compound is prepared by a method according to any of claims 1-7.
CN202110750674.3A 2021-07-02 2021-07-02 Preparation method and application of niobium-containing metal organic compound Pending CN113387980A (en)

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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1733967A (en) * 2004-03-12 2006-02-15 罗门哈斯公司 Precursor compounds for deposition of ceramic and metal films and preparation methods thereof
CN111440210A (en) * 2020-05-19 2020-07-24 合肥安德科铭半导体科技有限公司 Preparation method, product and application of niobium or tantalum-containing organic compound

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1733967A (en) * 2004-03-12 2006-02-15 罗门哈斯公司 Precursor compounds for deposition of ceramic and metal films and preparation methods thereof
CN111440210A (en) * 2020-05-19 2020-07-24 合肥安德科铭半导体科技有限公司 Preparation method, product and application of niobium or tantalum-containing organic compound

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
ARNE BAUNEMANN ET AL: "Mixed amido/imido/guanidinato complexes of niobium: potential precursors for MOCVD of niobium nitride thin films", DALTON TRANS., pages 3715 - 3722 *

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