CN115572307B - Silicone composition and use thereof - Google Patents
Silicone composition and use thereof Download PDFInfo
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- CN115572307B CN115572307B CN202211462774.7A CN202211462774A CN115572307B CN 115572307 B CN115572307 B CN 115572307B CN 202211462774 A CN202211462774 A CN 202211462774A CN 115572307 B CN115572307 B CN 115572307B
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- 239000000203 mixture Substances 0.000 title claims abstract description 113
- 229920001296 polysiloxane Polymers 0.000 title claims abstract description 43
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 86
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 61
- 239000000460 chlorine Substances 0.000 claims abstract description 61
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 61
- 239000006227 byproduct Substances 0.000 claims abstract description 37
- NBBQQQJUOYRZCA-UHFFFAOYSA-N diethoxymethylsilane Chemical compound CCOC([SiH3])OCC NBBQQQJUOYRZCA-UHFFFAOYSA-N 0.000 claims abstract description 26
- 230000029087 digestion Effects 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 74
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 24
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 23
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 23
- 239000011229 interlayer Substances 0.000 claims description 23
- 238000001514 detection method Methods 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 13
- PESLMYOAEOTLFJ-UHFFFAOYSA-N ethoxymethylsilane Chemical compound CCOC[SiH3] PESLMYOAEOTLFJ-UHFFFAOYSA-N 0.000 claims description 11
- NKLYMYLJOXIVFB-UHFFFAOYSA-N triethoxymethylsilane Chemical compound CCOC([SiH3])(OCC)OCC NKLYMYLJOXIVFB-UHFFFAOYSA-N 0.000 claims description 10
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 claims description 9
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 claims description 9
- QSTBLOFUMQAHQZ-UHFFFAOYSA-N chloro(ethoxymethyl)silane Chemical compound C(C)OC[SiH2]Cl QSTBLOFUMQAHQZ-UHFFFAOYSA-N 0.000 claims description 8
- RECJVUVMDRZCPY-UHFFFAOYSA-N diethoxymethoxysilane Chemical compound C(C)OC(O[SiH3])OCC RECJVUVMDRZCPY-UHFFFAOYSA-N 0.000 claims description 8
- YYLGKUPAFFKGRQ-UHFFFAOYSA-N dimethyldiethoxysilane Chemical compound CCO[Si](C)(C)OCC YYLGKUPAFFKGRQ-UHFFFAOYSA-N 0.000 claims description 8
- GKDXCOQOVKKXEM-UHFFFAOYSA-N ethoxy-methoxy-methylsilane Chemical compound CCO[SiH](C)OC GKDXCOQOVKKXEM-UHFFFAOYSA-N 0.000 claims description 8
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical compound Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 claims description 5
- 239000005046 Chlorosilane Substances 0.000 claims description 4
- 238000005229 chemical vapour deposition Methods 0.000 claims description 3
- 150000004045 organic chlorine compounds Chemical class 0.000 claims description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 abstract description 27
- 229910052710 silicon Inorganic materials 0.000 abstract description 27
- 239000010703 silicon Substances 0.000 abstract description 27
- 239000000047 product Substances 0.000 abstract description 25
- 239000004065 semiconductor Substances 0.000 abstract description 10
- 239000012535 impurity Substances 0.000 abstract description 4
- 238000002360 preparation method Methods 0.000 abstract description 4
- 238000003908 quality control method Methods 0.000 abstract description 2
- 239000007789 gas Substances 0.000 description 48
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 40
- 239000010408 film Substances 0.000 description 40
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 26
- -1 alkoxy silane Chemical compound 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 14
- 229910001504 inorganic chloride Inorganic materials 0.000 description 14
- 238000009835 boiling Methods 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- 238000010992 reflux Methods 0.000 description 12
- 239000010410 layer Substances 0.000 description 10
- 238000001228 spectrum Methods 0.000 description 10
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
- 238000000746 purification Methods 0.000 description 8
- 239000012043 crude product Substances 0.000 description 7
- 239000000758 substrate Substances 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 4
- 229910052786 argon Inorganic materials 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 230000007547 defect Effects 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 229910000077 silane Inorganic materials 0.000 description 4
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 4
- 238000005273 aeration Methods 0.000 description 3
- 238000005234 chemical deposition Methods 0.000 description 3
- 150000001805 chlorine compounds Chemical class 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 238000007599 discharging Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 229910001961 silver nitrate Inorganic materials 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- HMDDXIMCDZRSNE-UHFFFAOYSA-N [C].[Si] Chemical compound [C].[Si] HMDDXIMCDZRSNE-UHFFFAOYSA-N 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 229910021417 amorphous silicon Inorganic materials 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- SLLGVCUQYRMELA-UHFFFAOYSA-N chlorosilicon Chemical compound Cl[Si] SLLGVCUQYRMELA-UHFFFAOYSA-N 0.000 description 1
- KTQYJQFGNYHXMB-UHFFFAOYSA-N dichloro(methyl)silicon Chemical compound C[Si](Cl)Cl KTQYJQFGNYHXMB-UHFFFAOYSA-N 0.000 description 1
- UWGIJJRGSGDBFJ-UHFFFAOYSA-N dichloromethylsilane Chemical compound [SiH3]C(Cl)Cl UWGIJJRGSGDBFJ-UHFFFAOYSA-N 0.000 description 1
- 239000003989 dielectric material Substances 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 238000006459 hydrosilylation reaction Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000005048 methyldichlorosilane Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000011112 process operation Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000012686 silicon precursor Substances 0.000 description 1
- FDNAPBUWERUEDA-UHFFFAOYSA-N silicon tetrachloride Chemical compound Cl[Si](Cl)(Cl)Cl FDNAPBUWERUEDA-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Classifications
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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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/20—Purification, separation
-
- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/18—Manufacture of films or sheets
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2383/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen, or carbon only; Derivatives of such polymers
- C08J2383/04—Polysiloxanes
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
Abstract
The invention discloses a silicone composition comprising: diethoxymethylsilane; a first concentration of dissolved residual inorganic and organic chlorine; ethanol of a second concentration; and a third concentration of byproducts (impurities); wherein the first concentration is defined as the sum of the concentrations of all chlorine elements present obtained by the organosilicon composition under total digestion. The organic silicon composition introduces the concept of byproducts (impurities), plays a key role in quality control of products, has low residues of inorganic chlorine, organic chlorine and ethanol, and particularly has little residues of inorganic chlorine, so that the quality of diethoxymethylsilane is stable, and when the organic silicon composition is applied to semiconductor devices, such as the preparation of various low-dielectric-constant films, the dielectric constant of the low-dielectric-constant films is less than or equal to 3.5, and the performance is stable and controllable, and is superior to the existing organic silicon composition.
Description
Technical Field
The invention relates to the field of organic silicon compositions, in particular to an organic silicon composition and application thereof.
Background
The alkoxy silane is mainly used for synthesizing organosilicon intermediates and high molecular compounds, and can also be used as a hydrosilylation reagent. Meanwhile, it is applicable to semiconductor devices. In order to reduce Resistance Capacitance (RC) delay and interconnection delay, improve the performance of a semiconductor device, increase the circuit speed, require low-K or even ultra-low K dielectric materials, currently, a general ultra-low K dielectric layer adopts a low-K porous structure (SiCOH, k=2.2-2.5), silicon carbon nitride (k=4.8) and amorphous silicon carbide (k=2-3.6) are used as dielectric barrier layers, and PCVD/ALD thin films are used to form cavities between metal wires to realize metal interconnection between low-K dielectric layers. Taking an ultralow K dielectric mask layer as an example, an ultralow K dielectric mask layer is formed on a substrate by adopting alkoxy silane, wherein the alkoxy silane reacts with oxygen to generate a silicon dioxide glass body to form a thin oxygen layer, the surface of the ultralow K dielectric layer is flat, the original bulge defect is overcome, and the performance of the ultralow K dielectric layer is improved.
Diethoxymethylsilane (DEMS) is typically produced by reacting dichloromethylsilane with ethanol, for example, by the following chemical reaction:
CH 3 SiHCl 2 +2C 2 H 5 OH=CH 3 SiH(OC 2 H 5 ) 2 +2HCl。
in the above reaction, organic chlorine and inorganic chlorine byproducts, such as chlorosilane, organic chloride and hydrogen chloride, mainly appear in the form of hydrogen chloride or residual silicon chloride, and finally all form hydrogen chloride.
The prior organosilicon composition of alkoxy silane, such as CN101092689A, discloses an organosilicon product, and because alkaline chloride scavengers such as ammonia and amine compounds are additionally added in the purification process, excessive alkaline chloride scavengers such as metal salts and organic amines are remained in the purified organosilicon composition besides residual chlorides, so that excessive impurities in the organosilicon composition are excessive, the corresponding purity is lower, and the performance of the organosilicon composition is affected when semiconductor devices are manufactured. Therefore, there is a need to propose a silicone composition with low chloride residues.
Disclosure of Invention
The first invention aims to provide a low-residue inorganic chlorine, organic chlorine and low-residue ethanol organic silicon composition, which aims to solve the problems that the conventional organic silicon composition for semiconductor devices contains excessive basic chloride scavengers such as metal salts, organic amines and the like besides residual chlorides, so that impurities in the organic silicon composition are excessive, the purity is correspondingly low, and the performance of the semiconductor devices is influenced when the semiconductor devices are manufactured.
In order to achieve the above purpose, the invention is realized by the following technical scheme:
a silicone composition comprising:
diethoxymethylsilane;
a first concentration of dissolved residual inorganic and organic chlorine;
ethanol of a second concentration;
a third concentration of byproducts;
wherein the first concentration is defined as the sum of the concentrations of all chlorine elements present obtained by the organosilicon composition under total digestion.
Further, the inorganic chlorine comprises hydrogen chloride, and the organic chlorine comprises chlorosilane compounds and/or organic chlorine compounds.
Further, the first concentration of the dissolved residual inorganic chlorine and organic chlorine is between the instrument detection limit and 100ppm, the second concentration of the ethanol is between the instrument detection limit and 20ppm, and the third concentration of the byproducts is between the instrument detection limit and 5000ppm.
Further, the concentration of the dissolved residual inorganic chlorine is between the detection limit of the instrument and 10 ppm.
Still further, the concentration of the dissolved residual inorganic chlorine is preferably between the instrument detection limit and 1 ppm.
Further, the by-products include any one or more of a compound having a relative molecular weight of 164Da, a compound having a relative molecular weight of 208Da, a compound having a relative molecular weight of 148Da, a compound having a relative molecular weight of 194Da, a compound having a relative molecular weight of 178Da, a compound having a relative molecular weight of 150Da, a compound having a relative molecular weight of 120Da, a compound having a relative molecular weight of 124Da or 126Da, and a compound having a relative molecular weight of 90 Da.
Still further, the compound having a relative molecular weight of 164Da comprises triethoxysilane, the compound having a relative molecular weight of 208Da may comprise tetraethoxysilane, the compound having a relative molecular weight of 148Da comprises diethoxydimethylsilane, the compound having a relative molecular weight of 194Da comprises triethoxymethoxysilane, the compound having a relative molecular weight of 178Da comprises triethoxymethylsilane, the compound having a relative molecular weight of 150Da comprises diethoxymethoxysilane, the compound having a relative molecular weight of 120Da comprises ethoxymethoxymethylsilane, the compound having a relative molecular weight of 124Da or 126Da comprises ethoxymethylchlorosilane, and the compound having a relative molecular weight of 90Da comprises ethoxymethylsilane.
A second object of the present invention is to provide the use of the above-mentioned silicone composition, specifically, the use of the silicone composition in a low dielectric constant film.
Further, the low dielectric constant film comprises a low dielectric constant interlayer dielectric film, a porous low dielectric constant film or an air gap low dielectric constant film.
In a further scheme, the low-dielectric-constant film is a low-dielectric-constant interlayer dielectric film and is formed by the organic silicon composition through a chemical vapor deposition mode.
Further, the dielectric constant of the low-dielectric-constant interlayer dielectric film is less than or equal to 3.5.
Further, the low-dielectric-constant interlayer dielectric film is formed by Si a O b C c H d F e Expressed in terms of atomic percentages, a is more than or equal to 10% and less than or equal to 35%, b is more than or equal to 1% and less than or equal to 66%, c is more than or equal to 1% and less than or equal to 35%, d is more than or equal to 0 and less than or equal to 60%, e is more than or equal to 0 and less than or equal to 25%, and a+b+c+d+e=100%.
The beneficial effect of above-mentioned scheme is: the organosilicon precursor of the organosilicon composition of the invention is reacted with one or more other reactive species, such as oxygen, gaseous or liquid organic species, under chemical deposition vapor conditions sufficient to deposit a film on a substrate to deposit an interlayer dielectric film on the substrate. Through testing, the dielectric constant of the obtained interlayer dielectric film is less than or equal to 3.5, and the surface is flat and free from defects.
Compared with the prior art, the invention has the beneficial effects that: the organic silicon composition has low inorganic chlorine, organic chlorine and ethanol residues, particularly little inorganic chlorine residues, so that the organic silicon composition has stable quality, and when the organic silicon composition is applied to semiconductor devices, for example, when various low dielectric constant films are prepared, the dielectric constant of the low dielectric constant film is less than or equal to 3.5, and the performance is stable and controllable, and is better than the existing organic silicon composition.
Drawings
In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings that are required to be used in the embodiments or the description of the prior art will be briefly described below, and it is obvious that the drawings in the following description are only some embodiments described in the present invention, and other drawings may be obtained according to the drawings without inventive effort to those skilled in the art.
FIGS. 1-2 are GC and MS spectra of a silicone composition byproduct triethoxysilane in example 1 of the present invention;
FIGS. 3-4 are GC and MS spectra of the byproduct tetraethoxysilane of the silicone composition of example 1 of the present invention;
FIGS. 5-6 are GC and MS spectra of a byproduct diethoxydimethylsilane of a silicone composition in an embodiment of the invention;
FIGS. 7-8 are GC and MS spectra of a silicone composition byproduct triethoxymethoxysilane in an embodiment of the present invention;
FIGS. 9-10 are GC and MS spectra of a byproduct diethoxymethoxysilane from a silicone composition in an embodiment of the present invention;
FIGS. 11-12 are GC and MS spectra of the silicone composition byproduct ethoxymethoxymethyl silane in an embodiment of the invention;
FIGS. 13-14 are GC and MS spectra of a silicone composition byproduct ethoxymethylchlorosilanes in an embodiment of the invention;
figures 15-16 are GC and MS spectra of the silicone composition byproduct ethoxymethylsilane in an example of the present invention.
Detailed Description
In order to make the technical solution of the present invention better understood by those skilled in the art, the technical solution of the present invention will be clearly and completely described below with reference to the accompanying drawings in the embodiments of the present invention, and it is apparent that the described embodiments are only some embodiments of the present invention, not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the present invention without making any inventive effort, shall fall within the scope of the present invention.
One aspect of the present invention provides a silicone composition comprising diethoxymethylsilane, a first concentration of dissolved residual total chloride, a second concentration of ethanol, and a third concentration of byproducts.
Wherein the total chloride comprises inorganic and organic chlorine, the first concentration being defined as the sum of the concentrations of all chlorine elements present obtained in the organosilicon composition under total digestion.
The second concentration represents the highest concentration of alcohol that cannot be removed during purification.
The third concentration represents the highest concentration of byproducts generated during the purification process.
Preferably, the inorganic chlorine comprises hydrogen chloride and the organic chlorine comprises chlorosilanes and/or organic chloride. The chlorosilane compound is chlorsilane.
Preferably, the first concentration of the dissolved residual inorganic chlorine and organic chlorine is between the instrument detection limit and 100ppm, the second concentration of the ethanol is between the instrument detection limit and 20ppm, and the third concentration of the byproduct is between the instrument detection limit and 5000ppm.
Further, the first concentration of the dissolved residual inorganic chlorine and organic chlorine is between the instrument detection limit and 40ppm, the second concentration of the ethanol is between the instrument detection limit and 10ppm, and the third concentration of the byproduct is between the instrument detection limit and 5000ppm.
Still further, the concentration of the dissolved residual inorganic chlorine is between instrument detection limit and 10 ppm.
Still further, the concentration of the dissolved residual inorganic chlorine is preferably between the instrument detection limit and 1ppm, and still further may reach less than 0.5ppm.
Preferably, the by-products include any one or more of a compound having a relative molecular weight of 164Da, a compound having a relative molecular weight of 208Da, a compound having a relative molecular weight of 148Da, a compound having a relative molecular weight of 194Da, a compound having a relative molecular weight of 178Da, a compound having a relative molecular weight of 150Da, a compound having a relative molecular weight of 120Da, a compound having a relative molecular weight of 124Da or 126Da, and a compound having a relative molecular weight of 90 Da.
Wherein the compound having a relative molecular weight of 164Da may comprise triethoxysilane or other compounds, the compound having a relative molecular weight of 208Da may comprise tetraethoxysilane or other compounds, the compound having a relative molecular weight of 148Da may comprise diethoxymethylsilane or other compounds, the compound having a relative molecular weight of 194Da may comprise triethoxymethylsilane or other compounds, the compound having a relative molecular weight of 178Da may comprise triethoxymethylsilane or other compounds, the compound having a relative molecular weight of 150Da may comprise diethoxymethoxysilane or other compounds, the compound having a relative molecular weight of 120Da may comprise ethoxymethoxymethylsilane or other compounds, the compound having a relative molecular weight of 124Da or 126Da may comprise ethoxymethylchlorosilane or other compounds, and the compound having a relative molecular weight of 90Da may comprise ethoxymethylsilane or other compounds.
The existence of the byproducts does not affect the film forming property of the film, and the film quality control can play a key role because the structure is relatively clear and the concentration control is proper.
In another aspect, the invention provides the use of a silicone composition in a low dielectric constant film.
Preferably, the low dielectric constant film comprises a low dielectric constant interlayer dielectric film, a porous low dielectric constant film, or an air gap low dielectric constant film.
Preferably, the low-dielectric-constant film is a low-dielectric-constant interlayer dielectric film, and is formed by chemical vapor deposition from the organic silicon composition.
Preferably, the low-k interlayer dielectric film has a dielectric constant of 3.5 or less.
A method for producing a low-dielectric-constant interlayer dielectric film, for example, comprises reacting a silicone precursor comprising at least the silicone composition of the present invention with one or more other reactive species under chemical deposition vapor phase conditions sufficient to deposit a film on a substrate to form an interlayer dielectric film having a dielectric constant of 3.5 or less.
Wherein the interlayer dielectric film is made of Si a O b C c H d F e Expressed in terms of atomic percentages, a is more than or equal to 10% and less than or equal to 35%, b is more than or equal to 1% and less than or equal to 66%, c is more than or equal to 1% and less than or equal to 35%, d is more than or equal to 0 and less than or equal to 60%, e is more than or equal to 0 and less than or equal to 25%, and a+b+c+d+e=100%.
The silicone composition of the present invention can be obtained by the following purification method, or can be obtained by other purification methods, and specific purification steps include:
1) Mixing the organosilicon composition to be purified with ethanol to obtain a mixture;
2) Reacting the mixture to convert chloride ions in the organochlorine to hydrogen chloride; the mixture is contacted with a gas, hydrogen chloride is removed by gas exchange, and the reaction is caused to move in the forward direction, thereby obtaining a purified silicone composition.
The equation for the reaction of organochlorine with ethanol is as follows:
preferably, in step 1), the molar concentration ratio of chloride ions to ethanol in the organic chloride is 1:1 to 1:10 6 And the maximum amount of ethanol is 10% of the total amount of materials to ensure complete reaction.
Preferably, step 2) comprises: allowing the mixture to reflux under normal pressure or reduced pressure and in a boiling state, thereby reacting ethanol with organic chlorine, and converting chloride ions in the organic chlorine into hydrogen chloride; and (3) in a boiling state, introducing gas, contacting the mixture with the gas, removing the hydrogen chloride through gas exchange, and simultaneously promoting the reaction of the organic chlorine and the ethanol and the reaction of the organic chlorine and the ethanol to move forward, so as to obtain the purified organosilicon composition.
More preferably, the reflux time is 1 to 30 hours, preferably 1 to 24 hours.
More preferably, the mixture is contacted with the gas for a period of time ranging from 2 to 48 hours.
Preferably, the gas includes inert gases such as argon, helium, and additionally, the gas may include nitrogen, hydrogen, carbon monoxide, and the like. The gas may be one kind or two or more kinds in combination.
Preferably, the flow rate of the gas is less than or equal to 10L/min. The total amount of gas was 10% of the total chloride concentration in the silicone composition 3 -10 6 Multiple times. The total time of gas introduction is 2-48 hours, wherein the total chloride comprises inorganic chloride and organic chloride. By controlling parameters such as gas flow rate, gas inlet time, total gas amount and the like, the gas exchange can be ensured to be complete, and the reaction is further pushed to move forward, so that the removal of chloride ions is completed.
Preferably, the method further comprises detecting inorganic chlorine and/or organic chlorine remained in the organic silicon composition by using a gas detection gas and/or silver nitrate solution. For example, by means of a gas detector for the exhaust gas or by titration with silver nitrate without discoloration.
The organic chlorine and ethanol are removed by reaction and rectification reflux, the hydrogen chloride is removed by gas exchange, the reaction is promoted to move forward, meanwhile, the residual inorganic chlorine and/or organic chlorine in the organic silicon composition are detected, and when the purity requirement is met, namely the content of the dissolved residual inorganic chlorine in the organic silicon composition is less than 10ppm, preferably less than 1ppm, the purified organic silicon composition product is obtained.
The purification method is convenient, does not introduce extra metal salt, organic amine and other products, and simultaneously promotes the reaction of the organic chlorine and the ethanol to move forward when the gas is used for exchanging the hydrogen chloride, thereby further completing the removal of chloride ions, namely synchronously removing the inorganic chlorine and the organic chlorine. The purified novel organosilicon composition has little residue of chloride, especially inorganic chlorine, and contains proper ethanol and byproducts, so that the organosilicon composition has stable quality.
The following describes the technical scheme of the present invention in detail with reference to several preferred embodiments.
Example 1
In the prior art, the preparation method of the DEMS comprises the following steps: 150 g of absolute ethanol are introduced into a 1L round-bottomed flask, cooled to 0℃and 115 g of methyldichlorosilane (MeSiHCl) 2 ) And kept for 12 hours, and after gradually warming to room temperature, the mixture is boiled and refluxed for 4 hours, and 121 g of diethoxymethylsilane is obtained by distillation, with a yield of 90%. The nuclear magnetic spectrum is 1 H-NMR(C 6 D 6 ) 0.0 (d, 3H), 0.97 (t, 6H), 3.5 (dd, 4H), 4.7 (s, 1H). I.e. crude T1.
The crude product T1 prepared contains a large amount of inorganic chloride, organic chloride and ethanol besides diethoxymethylsilane. The total concentration of inorganic chloride and organic chloride is 1500ppm, wherein the concentration of inorganic chloride is 550ppm, the content of ethanol is 2500 ppm, the content of inorganic chloride and ethanol in the crude product is too high to be directly applied to the preparation of the low dielectric constant film, and therefore the novel diethoxymethylsilane organosilicon composition is obtained by purifying the low dielectric constant film. When the crude product T1 is purified, the steps are as follows:
1) Taking 100 g of crude product T1, and adding 10g of ethanol into the crude product T1;
2) Refluxing the mixture under normal pressure and boiling state for 1 hour, so that ethanol reacts with organic chloride, and chloride ions in the organic chloride are converted into hydrogen chloride; the reaction formula is as follows:
and (3) under the boiling state, introducing nitrogen into the mixture, enabling the mixture to be in contact with gas, safely discharging tail gas under the protection of the nitrogen and removing hydrogen chloride carried in the reflux liquid through gas exchange. Wherein the maximum gas flow rate is controlled at 10L/min, the aeration time is 24 hours, and the total amount of nitrogen gas is 12000L.
And detecting tail gas by using a gas detector, further detecting residual inorganic chlorine in the organic silicon composition, and when the content of the dissolved residual inorganic chlorine in the organic silicon composition is less than 10ppm, removing 10g of front cut fraction by distillation, collecting 60g of middle cut fraction and keeping the kettle residue still, thus obtaining the final DEMS composition product, namely a product T2.
The silicone composition obtained in this example contained diethoxymethylsilane and total chloride at a first concentration of 40ppm, wherein the inorganic chloride was 0.9 ppm, and ethanol at a second concentration of 22 ppm. The resulting silicone composition also contains a third concentration of byproducts, such as triethoxysilane having a relative molecular weight of 164Da, tetraethoxysilane having a relative molecular weight of 208Da, diethoxydimethylsilane having a relative molecular weight of 148Da, triethoxymethoxysilane having a relative molecular weight of 194Da, triethoxymethylsilane having a relative molecular weight of 178Da, diethoxymethoxysilane having a relative molecular weight of 150Da, ethoxymethoxymethylsilane having a relative molecular weight of 120Da, ethoxymethylchlorosilane having a relative molecular weight of 124Da or 126Da, and ethoxymethylsilane having a relative molecular weight of 90 Da.
The total concentration of byproducts was 5000ppm. The GC and MS spectra of part of the byproducts are shown in figures 1-16.
Example 2
100 g of crude DEMS product T1 from example 1 was taken and 1g of ethanol was added thereto. The mixture was refluxed at normal pressure and boiling for 30 hours to react the ethanol with the organic chloride in the crude DEMS product to convert the organic chloride to hydrogen chloride.
After the reflux time is over, nitrogen and argon are introduced into the mixture in a boiling state, wherein the ratio of the nitrogen to the argon is 8: and 2, fully contacting the mixture with gas, and simultaneously discharging tail gas safely under the protection of nitrogen and argon, thereby removing hydrogen chloride through gas exchange. The maximum gas flow rate was controlled at 5L/min, the aeration time was 48 hours, and the total amount of gas was 12000L.
And detecting the residual inorganic chlorine in the alkoxysilane composition by using a gas detector for tail gas, when the content of the dissolved residual inorganic chlorine in the organosilicon composition is less than 10ppm, obtaining a purified organosilicon composition, distilling to remove 10g of front cut fraction, collecting 60g of middle cut fraction, and keeping the kettle residue still, thus obtaining a purified DEMS composition product, namely a product T3. The total concentration of inorganic chloride and organic chloride in the product T3 was 18ppm, wherein the inorganic chloride concentration was 0.3 ppm, the ethanol concentration was 5.7 ppm, and the resulting silicone composition further contained a third concentration of by-products, which were triethoxysilane having a relative molecular weight of 164Da, tetraethoxysilane having a relative molecular weight of 208Da, diethoxydimethylsilane having a relative molecular weight of 148Da, triethoxymethoxysilane having a relative molecular weight of 194Da, triethoxymethylsilane having a relative molecular weight of 178Da, diethoxymethoxysilane having a relative molecular weight of 150Da, ethoxymethoxymethylsilane having a relative molecular weight of 120Da, ethoxymethylchlorosilane having a relative molecular weight of 124Da or 126Da, and ethoxymethylsilane having a relative molecular weight of 90 Da. The total concentration of by-products was 4800ppm.
Example 3
100 g of crude DEMS product T1 from example 1 was taken and 1g of ethanol was added thereto. The mixture is refluxed under normal pressure and boiling state for 24 hours, so that the ethanol reacts with the organic chloride in the crude DEMS product, and the organic chloride is converted into hydrogen chloride.
After the reflux time is over, nitrogen is introduced into the mixture in a boiling state, so that the mixture is fully contacted with the gas, and the tail gas is safely discharged under the reflux and nitrogen protection, thereby removing the hydrogen chloride through gas exchange. The maximum flow rate of nitrogen was controlled at 10L/min, the aeration time was 2 hours, and the total amount of nitrogen gas was 1200L.
And detecting the residual inorganic chlorine in the organic silicon composition by adopting a gas detector for tail gas, when the content of the dissolved residual inorganic chlorine in the organic silicon composition is less than 10ppm, removing 10g of front cut fraction by distillation, collecting 60g of middle cut fraction, and obtaining a purified DEMS composition product, namely a product T4. The total concentration of inorganic chloride and organic chloride in the product T4 was 25ppm, wherein the inorganic chloride concentration was 1.1 ppm, the ethanol concentration was 10.7 ppm, and the resulting silicone composition further contained a third concentration of by-products, which were triethoxysilane having a relative molecular weight of 164Da, tetraethoxysilane having a relative molecular weight of 208Da, diethoxydimethylsilane having a relative molecular weight of 148Da, triethoxymethoxysilane having a relative molecular weight of 194Da, triethoxymethylsilane having a relative molecular weight of 178Da, diethoxymethoxysilane having a relative molecular weight of 150Da, ethoxymethoxymethylsilane having a relative molecular weight of 120Da, ethoxymethylchlorosilane having a relative molecular weight of 124Da or 126Da, and ethoxymethylsilane having a relative molecular weight of 90 Da. The total concentration of by-products was 4500ppm.
Example 4
100 g of crude DEMS product T1 from example 1 was taken and 5g of ethanol was added thereto. The mixture is refluxed under normal pressure and boiling state for 12 hours, and the ethanol reacts with the organic chloride in the crude DEMS product to convert the organic chloride into hydrogen chloride.
After the reflux time is over, nitrogen is introduced into the mixture in a boiling state, so that the mixture is fully contacted with the gas, and the tail gas is safely discharged under the reflux and nitrogen protection, thereby removing the hydrogen chloride through gas exchange. The maximum flow rate of nitrogen is controlled at 10L/min, the ventilation time is 12h, and the total amount of gas is 7200L.
And detecting the residual inorganic chlorine in the organic silicon composition by using a gas detector for tail gas, when the content of the dissolved residual inorganic chlorine in the organic silicon composition is less than 10ppm, removing 10g of front cut fraction by distillation, collecting 60g of middle cut fraction, and keeping the residue still to obtain a purified DEMS composition product, namely a product T5, wherein the total concentration of inorganic chloride and organic chloride in the product T5 is 10ppm, the concentration of inorganic chlorine is 0.5ppm, the concentration of ethanol is 5.3 ppm, and the obtained organic silicon composition also contains a byproduct with a third concentration, wherein the byproduct is triethoxysilane with a relative molecular weight of 164Da, tetraethoxysilane with a relative molecular weight of 208Da, diethoxydimethylsilane with a relative molecular weight of 148Da, triethoxymethoxysilane with a relative molecular weight of 194Da, triethoxymethylsilane with a relative molecular weight of 178Da, diethoxymethylsilane with a relative molecular weight of 150Da, ethoxymethylsilane with a relative molecular weight of 120Da, ethoxymethylsilane with a relative molecular weight of 124Da or ethoxymethylsilane with a relative molecular weight of 126Da and the total concentration of 4000ppm.
Example 5
The embodiment provides a low-dielectric-constant interlayer dielectric film, which is prepared by the following steps:
an interlayer dielectric film is deposited on a substrate by reacting a silicone precursor comprising at least the product of silicone composition T2 with oxygen, gaseous and liquid organic species, and the like, under chemical deposition vapor conditions sufficient to deposit the film on the substrate. Through testing, the dielectric constant of the obtained interlayer dielectric film is less than or equal to 3.5, and the surface is flat and free from defects.
Wherein the interlayer dielectric film is made of Si a O b C c H d F e Expressed in terms of atomic percentages, a is more than or equal to 10% and less than or equal to 35%, b is more than or equal to 1% and less than or equal to 66%, c is more than or equal to 1% and less than or equal to 35%, d is more than or equal to 0 and less than or equal to 60%, e is more than or equal to 0 and less than or equal to 25%, and a+b+c+d+e=100%.
In other embodiments, the resulting silicone composition may have a difference in the byproducts contained therein, such as any one or a combination of two or more of triethoxysilane or other compounds having a relative molecular weight of 164Da, tetraethoxysilane or other compounds having a relative molecular weight of 208Da, diethoxydimethylsilane or other compounds having a relative molecular weight of 148Da, triethoxymethoxysilane or other compounds having a relative molecular weight of 194Da, triethoxymethylsilane or other compounds having a relative molecular weight of 178Da, diethoxymethoxysilane or other compounds having a relative molecular weight of 150Da, ethoxymethoxymethylsilane or other compounds having a relative molecular weight of 120Da, ethoxymethylchlorosilane or other compounds having a relative molecular weight of 124Da or 126Da, and ethoxymethylsilane or other compounds having a relative molecular weight of 90 Da.
Comparative example 1
1) Taking 100 g of DEMS crude product T1, and adding 10g of ethanol into the DEMS crude product T1;
2) Refluxing the mixture under normal pressure and boiling state for 1 hour, so that ethanol reacts with organic chloride, and chloride ions in the organic chloride are converted into hydrogen chloride; the reaction formula is as follows:
in the boiling state, no gas is introduced into the mixture, and the generated hydrogen chloride is not carried out, so that the organic chlorine and the inorganic chlorine in the system still exist in a large amount. After the completion of the reflux, the silicone composition was obtained by distillation. In the product, the total concentration of the inorganic chloride and the organic chloride is 520pm, wherein the concentration of the inorganic chloride is 107ppm, the concentration of the ethanol is 52ppm, and the total concentration of byproducts is more than 1 percent. The product has more chloride and ethanol residues, excessive concentration of byproducts and unstable quality, and is difficult to be applied to semiconductor devices.
Comparative example 2
The same procedure as in example 5 was followed except that the organic silicon composition prepared by the purification method of comparative example 1 was used as the organic silicon precursor, and the organic silicon composition was reacted with oxygen, gaseous and liquid organic substances, etc., to deposit an interlayer dielectric film on a substrate. Through testing, the dielectric constant of the obtained interlayer dielectric film is more than 3.5, and the surface of the interlayer dielectric film has convex defects.
From examples 1 to 5 and comparative examples 1 to 2, it was found that the purified silicone composition obtained by the above-described embodiments of the present invention had little residue of chlorides, particularly inorganic chlorine, and contained suitable ethanol and by-products, and thus the silicone composition was stable in quality. When applied to a semiconductor device such as a low-k dielectric mask layer, the method has the effect of improving the performance of the mask layer. By adopting the technical scheme, the preparation process is convenient, no additional products such as metal salt and organic amine are introduced, and meanwhile, when the gas is used for exchanging hydrogen chloride, the reaction of the organic chloride and ethanol can be promoted to move forward, so that the removal of chloride ions is further completed, namely, the inorganic chloride and the organic chloride are synchronously removed.
Furthermore, the inventors have also made experiments with other materials, process operations, and process conditions described herein with reference to the foregoing examples, to obtain desirable results, whether a silicone composition is obtained or other low dielectric constant films are prepared from the obtained silicone composition.
The various aspects, embodiments, features and examples of the invention are to be considered in all respects as illustrative and not intended to limit the invention, the scope of which is defined solely by the claims. Other embodiments, modifications, and uses will be apparent to those skilled in the art without departing from the spirit and scope of the claimed invention.
The use of headings and chapters in this disclosure is not meant to limit the disclosure; each section may apply to any aspect, embodiment, or feature of the present invention.
Throughout this disclosure, where a composition is described as having, comprising, or including a particular component, or where a process is described as having, comprising, or including a particular process step, it is contemplated that the composition of the teachings of the present invention also consist essentially of, or consist of, the recited component, and that the process of the teachings of the present invention also consist essentially of, or consist of, the recited process step.
It should be understood that the order of steps or order in which a particular action is performed is not critical, as long as the present teachings remain operable. Furthermore, two or more steps or actions may be performed simultaneously.
While the invention has been described with reference to an illustrative embodiment, it will be understood by those skilled in the art that various other changes, omissions and/or additions may be made and substantial equivalents may be substituted for elements thereof without departing from the spirit and scope of the invention. In addition, many modifications may be made to adapt a particular situation or material to the teachings of the invention without departing from the scope thereof. Therefore, it is intended that the invention not be limited to the particular embodiment disclosed for carrying out this invention, but that the invention will include all embodiments falling within the scope of the appended claims. Moreover, unless specifically stated any use of the terms first, second, etc. do not denote any order or importance, but rather the terms first, second, etc. are used to distinguish one element from another.
Claims (10)
1. A silicone composition characterized in that it comprises:
diethoxymethylsilane;
a first concentration of dissolved residual inorganic and organic chlorine;
ethanol with a second concentration, wherein the second concentration of the ethanol is between 20ppm and the detection limit of an instrument;
and a third concentration of byproducts, the third concentration of byproducts being between instrument detection limit and 5000 ppm;
wherein the first concentration is defined as the sum of all concentrations of elemental chlorine present obtained by the silicone composition under total digestion and is between instrument detection limit and 100 ppm;
the concentration of the dissolved residual inorganic chlorine is between the instrument detection limit and 10 ppm.
2. The silicone composition according to claim 1, wherein the inorganic chlorine comprises hydrogen chloride and the organic chlorine comprises a chlorosilane-based compound and/or an organic chlorine compound.
3. The silicone composition according to claim 1, characterized in that the concentration of dissolved residual inorganic chlorine is preferably between instrument detection limits to 1 ppm.
4. The silicone composition according to claim 1, wherein the by-products comprise any one or more of a compound having a relative molecular weight of 164Da, a compound having a relative molecular weight of 208Da, a compound having a relative molecular weight of 148Da, a compound having a relative molecular weight of 194Da, a compound having a relative molecular weight of 178Da, a compound having a relative molecular weight of 150Da, a compound having a relative molecular weight of 120Da, a compound having a relative molecular weight of 124Da or 126Da, and a compound having a relative molecular weight of 90 Da.
5. The silicone composition of claim 4, wherein the compound having a relative molecular weight of 1 6D 4D a comprises triethoxysilane, the compound having a relative molecular weight of 208Da comprises tetraethoxysilane, the compound having a relative molecular weight of 148Da comprises diethoxydimethylsilane, the compound having a relative molecular weight of 194Da comprises triethoxymethylsilane, the compound having a relative molecular weight of 178Da comprises triethoxymethylsilane, the compound having a relative molecular weight of 150Da comprises diethoxymethoxysilane, the compound having a relative molecular weight of 120Da comprises ethoxymethoxymethylsilane, the compound having a relative molecular weight of 124Da or 126Da comprises ethoxymethylchlorosilane, and the compound having a relative molecular weight of 90Da comprises ethoxymethylsilane.
6. Use of the silicone composition of any one of claims 1-5 in a low dielectric constant film.
7. The use of the silicone composition according to claim 6, wherein the low dielectric constant film comprises a low dielectric constant interlayer dielectric film, a porous low dielectric constant film, or an air gap low dielectric constant film.
8. The method of claim 7, wherein the low-k dielectric film is a low-k interlayer dielectric film formed by chemical vapor deposition of the composition.
9. The use of the silicone composition according to claim 8, wherein the low-k interlayer dielectric film has a dielectric constant of 3.5 or less.
10. The use of the composition according to claim 8, wherein the low-k interlayer dielectric film is made of the formula Si a O b C c H d F e Expressed in terms of atomic percentages, a is more than or equal to 10% and less than or equal to 35%, b is more than or equal to 1% and less than or equal to 66%, c is more than or equal to 1% and less than or equal to 35%, d is more than or equal to 0 and less than or equal to 60%, e is more than or equal to 0 and less than or equal to 25%, and a+b+c+d+e=100%.
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|---|---|---|---|---|
| US4228092A (en) * | 1978-01-02 | 1980-10-14 | Dynamit Nobel Aktiengesellschaft | Process for the preparation of organoalkoxysilanes |
| US6177584B1 (en) * | 1998-10-26 | 2001-01-23 | Degussa-Huels Aktiengesellschaft | Process for neutralizing and reducing residual halogen contents in alkoxysilanes or alkoxysilane-based compositions |
| US6323356B1 (en) * | 1999-11-13 | 2001-11-27 | Degussa-Huels Aktiengesellschaft | Process for the preparation of alkoxysilanes |
| CN101250690A (en) * | 2007-02-05 | 2008-08-27 | 气体产品与化学公司 | Method of purifying organosilicon compositions used as precursors in chemical vapor deposition |
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4228092A (en) * | 1978-01-02 | 1980-10-14 | Dynamit Nobel Aktiengesellschaft | Process for the preparation of organoalkoxysilanes |
| US6177584B1 (en) * | 1998-10-26 | 2001-01-23 | Degussa-Huels Aktiengesellschaft | Process for neutralizing and reducing residual halogen contents in alkoxysilanes or alkoxysilane-based compositions |
| US6323356B1 (en) * | 1999-11-13 | 2001-11-27 | Degussa-Huels Aktiengesellschaft | Process for the preparation of alkoxysilanes |
| CN101250690A (en) * | 2007-02-05 | 2008-08-27 | 气体产品与化学公司 | Method of purifying organosilicon compositions used as precursors in chemical vapor deposition |
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