KR101799158B1 - Stannum precursors, preparation method thereof and process for the formation of thin film using the same - Google Patents
Stannum precursors, preparation method thereof and process for the formation of thin film using the same Download PDFInfo
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- KR101799158B1 KR101799158B1 KR1020150158237A KR20150158237A KR101799158B1 KR 101799158 B1 KR101799158 B1 KR 101799158B1 KR 1020150158237 A KR1020150158237 A KR 1020150158237A KR 20150158237 A KR20150158237 A KR 20150158237A KR 101799158 B1 KR101799158 B1 KR 101799158B1
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- C07F7/22—Tin compounds
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- 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
- C23C16/06—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 metallic material
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- 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]
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- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/02104—Forming layers
- H01L21/02107—Forming insulating materials on a substrate
- H01L21/02109—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates
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- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
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- H01L21/02107—Forming insulating materials on a substrate
- H01L21/02109—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates
- H01L21/02205—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates the layer being characterised by the precursor material for deposition
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- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/02104—Forming layers
- H01L21/02107—Forming insulating materials on a substrate
- H01L21/02225—Forming insulating materials on a substrate characterised by the process for the formation of the insulating layer
- H01L21/0226—Forming insulating materials on a substrate characterised by the process for the formation of the insulating layer formation by a deposition process
- H01L21/02263—Forming insulating materials on a substrate characterised by the process for the formation of the insulating layer formation by a deposition process deposition from the gas or vapour phase
- H01L21/02271—Forming insulating materials on a substrate characterised by the process for the formation of the insulating layer formation by a deposition process deposition from the gas or vapour phase deposition by decomposition or reaction of gaseous or vapour phase compounds, i.e. chemical vapour deposition
- H01L21/0228—Forming insulating materials on a substrate characterised by the process for the formation of the insulating layer formation by a deposition process deposition from the gas or vapour phase deposition by decomposition or reaction of gaseous or vapour phase compounds, i.e. chemical vapour deposition deposition by cyclic CVD, e.g. ALD, ALE, pulsed CVD
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- H—ELECTRICITY
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- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having at least one potential-jump barrier or surface barrier, e.g. PN junction, depletion layer or carrier concentration layer
- H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having at least one potential-jump barrier or surface barrier, e.g. PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic System or AIIIBV compounds with or without impurities, e.g. doping materials
- H01L21/20—Deposition of semiconductor materials on a substrate, e.g. epitaxial growth solid phase epitaxy
- H01L21/205—Deposition of semiconductor materials on a substrate, e.g. epitaxial growth solid phase epitaxy using reduction or decomposition of a gaseous compound yielding a solid condensate, i.e. chemical deposition
Abstract
The present invention relates to a novel tin precursor having improved thermal stability and volatility, and a method of easily producing a high quality tin oxide thin film at an excellent growth rate at a low temperature using the tin precursor and a thin film produced thereby can do.
Description
More particularly, the present invention relates to a tin precursor which is improved in thermal stability and volatility and can be easily produced at a low temperature with high quality tin oxide thin films, a method for producing the tin precursor, a method for producing the tin precursor, ≪ / RTI >
Silicon is advantageous in terms of physical properties, lifetime, and performance stability, but vacuum deposition and annealing are required to form a thin film. Costly display equipment is costly. In this regard, efforts are recently being made to use a metal oxide material as a semiconductor channel layer, which metal oxide has the potential of being a transparent element.
Oxide semiconductors have higher electron mobility than amorphous silicon, are easier to process at low temperature than polycrystalline silicon, and are transparent in the visible light region and are studied as semiconductor layers of electronic devices such as thin film transistors.
As the oxide semiconductor, materials in which various kinds of metal atoms are added using indium (In), zinc (Zn), or the like as a matrix have been used. Thin films of oxide semiconductors are mainly fabricated by processes such as PLD (Pulsed Laser Deposition), sputtering, ALD (Atomic Layer Deposition). However, when indium (In) is included, the manufacturing cost of oxide semiconductors is increased, and the process mainly used also has the disadvantage of increasing the manufacturing cost.
Tin (Sn) oxide semiconductors are attracting attention because they can replace oxide semiconductors including indium. Chemical vapor deposition (CVD), atomic layer deposition (ALD), or the like has been used as a process for forming an oxide thin film having tin as a matrix. However, when a tin oxide thin film is produced by the CVD or ALD process as described above, the degree of deposition, the deposition control property, the crystallinity and the purity of the oxide thin film to be formed differ depending on the characteristics of the metal precursor, Precursor development is required.
Further, studies on the synthesis of tin precursors that can be used for such a semiconductor channel layer are insufficient, and development of a precursor having improved thermal stability, chemical reactivity, volatility and tin metal deposition rate is urgently required.
SUMMARY OF THE INVENTION The present invention has been made to solve the above problems,
It is an object of the present invention to provide a novel tin precursor which is improved in thermal stability and volatility and which is capable of easily producing a high quality tin oxide thin film at a low temperature.
It is another object of the present invention to provide a novel method for producing the tin precursor, a tin oxide thin film using the tin oxide thin film, and a tin oxide thin film produced from the tin oxide thin film.
In order to achieve the above object,
There is provided a tin precursor represented by the following general formula (1).
[Chemical Formula 1]
Wherein R 1 and R 2 are each independently a C1 to C10 linear or branched alkyl group.
In addition,
, Tin represented by the formula (1), comprising a step of reacting - (bistrimethylsilylamide die) [Tin (di- (bis trimethyl silylamide)), Sn (btsa) 2] A compound represented by the formula (2) with tin A method for producing a precursor is provided.
(2)
Wherein R 1 and R 2 are each independently a C1 to C10 linear or branched alkyl group.
In addition,
A tin oxide thin film is grown using the tin precursor represented by Formula 1 and a tin oxide thin film produced from the tin oxide thin film.
The tin precursor represented by the formula (1) of the present invention has an improved thermal stability and volatility, so that a tin oxide thin film of high quality can be easily produced using the tin precursor.
Figure 1 is a 1 H NMR spectrum for MDPA.
Figure 2 is the FT-IR spectrum for MDPA.
Figure 3 is a 1 H NMR spectrum for EDPA.
Figure 4 is the FT-IR spectrum for EDPA.
5 is a 1 H NMR spectrum for Sn (MDPA) 2 .
Figure 6 is a 13 C NMR spectrum for Sn (MDPA) 2 .
Figure 7 is the FT-IR spectrum for Sn (MDPA) 2 .
Figure 8 is TG / DTA data for Sn (MDPA) 2 .
Figure 9 is a 1 H NMR spectrum for Sn (EDPA) 2 .
10 is a 13 C NMR spectrum for Sn (EDPA) 2 .
11 is an FT-IR spectrum for Sn (EDPA) 2 .
Figure 12 is TG / DTA data for Sn (EDPA) 2 .
The present invention relates to a tin precursor represented by the following formula (1).
[Chemical Formula 1]
In the formula (1), R 1 and R 2 are each independently a C1 to C10 linear or branched alkyl group, more preferably methyl, ethyl, propyl, iso-propyl, Butyl, iso-butyl or tert-butyl.
The compound represented by Formula 1 is a novel compound having excellent thermal stability and improved volatility. In addition, when a thin film is manufactured using the same, the growth rate of the thin film is excellent and a thin film can be manufactured at a relatively low temperature.
The tin precursor represented by Formula 1 may be prepared by reacting a compound represented by Formula 2 as a starting material with Sn (btsa) 2 (btsa = bistrimethylsilylamine) in an organic solvent to induce a substitution reaction.
(2)
In Formula 2, R 1 and R 2 are each independently a C1 to C10 linear or branched alkyl group, more preferably methyl, ethyl, propyl, iso-propyl, Butyl, iso-butyl or tert-butyl.
Examples of the organic solvent used in the reaction include, but are not limited to, hexane, diethylether, toluene, tetrahydrofuran (THF), and dichloromethane (MC) Preferably, tetrahydrofuran (THF) or dichloromethane (MC) can be used.
The process for preparing the tin precursor of the present invention can be illustrated by the following reaction formula (1).
[Reaction Scheme 1]
[Formula 2] < EMI ID =
In the
According to
Reactants in this reaction can be used in stoichiometric equivalents.
The novel tin precursor represented by Formula 1 may be a white solid or a transparent liquid at room temperature, and is thermally stable and has good volatility.
When the tin oxide thin film is grown using the tin precursor, the thin film can be easily manufactured at a low temperature and the growth rate is good.
The novel tin precursor of the present invention is preferably used as a precursor for the production of a tin oxide thin film, particularly in processes using chemical vapor deposition (CVD) or atomic layer deposition (ALD).
For example, when a chemical vapor deposition (CVD) method is used, a tin oxide thin film can be formed on various substrates by supplying reactants and organic materials including the tin precursor of the present invention to a reactor. And has good volatility. Therefore, it is possible to produce a thin film under various conditions, and also to produce a thin film of good quality.
In addition, when using atomic layer deposition (ALD), for example, a tin oxide thin film can be produced by an ALD process using the tin precursor of the present invention. In the ALD process, a reactant containing the tin precursor of the present invention, and the pulses are chemically reacted with the wafer surface to achieve precise monolayer growth. Since the tin precursor of the present invention is thermally stable and has good volatility, a high quality tin oxide thin film can be easily produced by the ALD process.
The present invention may be better understood by the following examples, which are for the purpose of illustrating the invention and are not intended to limit the scope of protection defined by the appended claims.
< Synthetic example >
Synthetic example 1. N- 메틸oxy -2,2- dimethyl 프로탄 나드 ( MDPA ) synthesis
O- methylhydroxylamine hydrochloride (1.5 g, 1.1 eq) and 50 mL of tetrahydrofuran (THF) were placed in a round-bottom flask and stirred at 70 ° C for 12 hours. At 0 째 C, triethylamine (7 mL, 3 eq) was added thereto, and the mixture was stirred at room temperature for 30 minutes. Then, pivaloyl chloride (2 g, 1 eq) was slowly added dropwise and reacted at 70 ° C for 24 hours. After 24 hours, the solution was filtered using ethyl acetate (EA), concentrated under reduced pressure, and washed with EA. The thus-obtained mixture was purified by column chromatography (EA: Hex = 1: 1 to EA conversion) to obtain N- methoxy-2,2-dimethyl propanamide as a transparent crystal (1.2 g, 56%).
Synthetic example 2. N- ethoxy -2,2- dimethyl 프로탄 나드 ( EDPA ) synthesis
O- ethylhydroxylamine hydrochloride (10.1 g, 1.1 eq) and 130 mL of tetrahydrofuran (THF) were placed in a round-bottom flask and stirred at 70 ° C for 12 hours. At 0 째 C, triethyl amine (42 mL, 3 eq) was added thereto, the temperature was raised to room temperature, and the mixture was stirred for 30 minutes. Pivaloyl Chloride (12 g, 1 eq) was then slowly added dropwise and reacted at 70 ° C for 24 hours. After 24 hours, the mixture was filtered using ethyl acetate (EA), concentrated under reduced pressure, and distilled under reduced pressure to obtain a viscous, transparent liquid, N- ethoxy-2,2-dimethyl propanamide (10 g, 69% .
< Example > Synthesis of tin precursor materials
Example One. Sn (MDPA) 2 of Produce
Sn (btsa) 2 (0.84 g, 0.5 eq) and 5 mL of hexane were stirred. MDPA (0.5 g, 1 eq) prepared in Synthesis Example 1 and 5 mL of hexane were mixed and then added dropwise to the mixture of Sn (btsa) 2 and hexane at 0 ° C. When the solution became slowly transparent, it was reacted at room temperature for 12 hours. When the solid was visually confirmed, it was concentrated under reduced pressure and sublimated at 60 ° C / 10 -1 torr to obtain a target compound Sn (MDPA) 2 (0.2 g, 29%) as a white solid.
The results of 1 H-NMR (C 6 D 6 ), 13 C-NMR (C 6 D 6 ), FT-IR and TGA / DTA analyzes of the obtained compound are shown in FIG. 5 to FIG.
EA: calcd. (Found) SnC 12 H 24 O 4 N 2 : C 36.28 (38.04); H 6.61 (6.38); N 7.37 (7.39);
EI-MS (m / z): 380 (M < + & gt ; ).
Example 2. Sn (EDPA) 2 of Produce
Sn (btsa) 2 (0.8 g, 0.5 eq) and diethyl ether (10 mL) were stirred. EDPA (0.5 g, 1 eq) prepared in Synthesis Example 2 and 10 mL of diethyl ether were mixed and then added dropwise to a mixture of Sn (btsa) 2 and diethyl ether. When the solution became gradually transparent, it was reacted at room temperature for 24 hours. Then, the mixture was concentrated under reduced pressure and distillation was performed at 90 ° C / 10 -1 torr to obtain a target compound Sn (EDPA) 2 (0.24 g / 34%) as a transparent liquid.
The results of 1 H-NMR (C 6 D 6 ), 13 C-NMR (C 6 D 6 ), FT-IR and TGA / DTA analyzes of the obtained compound are shown in FIG. 9 to FIG.
EA: calcd. (Found) SnC 14 H 28 O 4 N 2 : C 41.73 (41.31); H 7.08 (6.90); N 6.73 (6.88);
EI-MS (m / z): 408 (M < + & gt ; ).
< Experimental Example >
Experimental Example 1. Analysis of tin precursor materials
In order to measure the first embodiment of the Sn (MDPA) 2 and Example 2 of the Sn (EDPA) 2 thermal stability and volatility and decomposition temperature, was used for thermogravimetric analysis (thermogravimetric analysis, TGA) method. In the TGA method, argon gas was introduced at a pressure of 1.5 bar / min while heating the product to 800 ° C at a rate of 10 ° C / minute. A TGA graph of the tin precursor compound synthesized in Example 1 is shown in Fig. 8, and a TGA graph of the tin precursor compound synthesized in Example 2 is shown in Fig. As can be seen from FIG. 8, the tin precursor compound of Example 1 had a mass reduction from 100 ° C and a final amount of 18% was observed at 436 ° C. Further, as can be seen from FIG. 12, the tin precursor compound of Example 2 had a mass reduction from 114 ° C and a final residual amount of 6.4% at 269 ° C.
In addition, the TGA data show that the degree of volatility of the compound of the present invention is very good.
Claims (6)
[Chemical Formula 1]
Wherein R 1 and R 2 are each independently a C1 to C10 linear or branched alkyl group.
(2)
Wherein R 1 and R 2 are each independently a C1 to C10 linear or branched alkyl group.
Wherein R 1 and R 2 are each independently selected from the group consisting of methyl, ethyl, propyl, iso-propyl, butyl, iso-butyl or tert T-butyl < / RTI >
Characterized in that the thin film growth process is carried out by chemical vapor deposition (CVD) or atomic layer deposition (ALD).
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| Application Number | Priority Date | Filing Date | Title |
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| KR1020150158237A KR101799158B1 (en) | 2015-11-11 | 2015-11-11 | Stannum precursors, preparation method thereof and process for the formation of thin film using the same |
| US15/775,347 US10858379B2 (en) | 2015-11-11 | 2016-10-11 | Metal precursor for making metal oxide |
| PCT/KR2016/011359 WO2017082541A1 (en) | 2015-11-11 | 2016-10-11 | Metal precursor, manufacturing method therefor, and method for forming thin film by using same |
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| KR1020150158237A KR101799158B1 (en) | 2015-11-11 | 2015-11-11 | Stannum precursors, preparation method thereof and process for the formation of thin film using the same |
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| KR102182245B1 (en) * | 2019-04-24 | 2020-11-24 | 한국화학연구원 | Copper alkoxyalkylamide complexes, preparation method thereof and process for thin film formation using the same |
| KR102625156B1 (en) * | 2021-06-17 | 2024-01-15 | 주식회사 이지티엠 | Organo tin compound for thin film deposition and method of forming tin containing thin film using the same |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US8030507B2 (en) | 2008-03-20 | 2011-10-04 | Korea Research Institute Of Chemical Technology | Tin amino-alkoxide complexes and process for preparing thereof |
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| US8030507B2 (en) | 2008-03-20 | 2011-10-04 | Korea Research Institute Of Chemical Technology | Tin amino-alkoxide complexes and process for preparing thereof |
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