US20070027287A1 - Polymer and process for producing the same, composition for forming insulating film, and insulating film and method of forming the same - Google Patents

Polymer and process for producing the same, composition for forming insulating film, and insulating film and method of forming the same Download PDF

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US20070027287A1
US20070027287A1 US11/489,468 US48946806A US2007027287A1 US 20070027287 A1 US20070027287 A1 US 20070027287A1 US 48946806 A US48946806 A US 48946806A US 2007027287 A1 US2007027287 A1 US 2007027287A1
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group
film
component
bis
individually represent
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Masahiro Akiyama
Takahiko Kurosawa
Hisashi Nakagawa
Atsushi Shiota
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JSR Corp
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JSR Corp
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Publication of US20070027287A1 publication Critical patent/US20070027287A1/en
Priority to US12/717,225 priority Critical patent/US8404786B2/en
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/42—Block-or graft-polymers containing polysiloxane sequences
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/48—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D183/00—Coating compositions based on 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; Coating compositions based on derivatives of such polymers
    • C09D183/14—Coating compositions based on 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; Coating compositions based on derivatives of such polymers in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
    • H01B3/00—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties
    • H01B3/18—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances
    • H01B3/30—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • 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
    • H01L21/02109—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
    • H01L21/02112—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 characterised by the material of the layer
    • H01L21/02123—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 characterised by the material of the layer the material containing silicon
    • H01L21/02126—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 characterised by the material of the layer the material containing silicon the material containing Si, O, and at least one of H, N, C, F, or other non-metal elements, e.g. SiOC, SiOC:H or SiONC
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • 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
    • H01L21/02109—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
    • H01L21/02112—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 characterised by the material of the layer
    • H01L21/02123—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 characterised by the material of the layer the material containing silicon
    • H01L21/02164—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 characterised by the material of the layer the material containing silicon the material being a silicon oxide, e.g. SiO2
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • 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
    • H01L21/02109—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
    • H01L21/02208—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 the precursor containing a compound comprising Si
    • H01L21/02214—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 the precursor containing a compound comprising Si the compound comprising silicon and oxygen
    • H01L21/02216—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 the precursor containing a compound comprising Si the compound comprising silicon and oxygen the compound being a molecule comprising at least one silicon-oxygen bond and the compound having hydrogen or an organic group attached to the silicon or oxygen, e.g. a siloxane
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • 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
    • H01L21/02282—Forming insulating materials on a substrate characterised by the process for the formation of the insulating layer formation by a deposition process liquid deposition, e.g. spin-coating, sol-gel techniques, spray coating
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • 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
    • H01L21/02296—Forming insulating materials on a substrate characterised by the treatment performed before or after the formation of the layer
    • H01L21/02318—Forming insulating materials on a substrate characterised by the treatment performed before or after the formation of the layer post-treatment
    • H01L21/02337—Forming insulating materials on a substrate characterised by the treatment performed before or after the formation of the layer post-treatment treatment by exposure to a gas or vapour
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • 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
    • H01L21/02296—Forming insulating materials on a substrate characterised by the treatment performed before or after the formation of the layer
    • H01L21/02318—Forming insulating materials on a substrate characterised by the treatment performed before or after the formation of the layer post-treatment
    • H01L21/02345—Forming insulating materials on a substrate characterised by the treatment performed before or after the formation of the layer post-treatment treatment by exposure to radiation, e.g. visible light
    • H01L21/02348—Forming insulating materials on a substrate characterised by the treatment performed before or after the formation of the layer post-treatment treatment by exposure to radiation, e.g. visible light treatment by exposure to UV light
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • 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
    • H01L21/02296—Forming insulating materials on a substrate characterised by the treatment performed before or after the formation of the layer
    • H01L21/02318—Forming insulating materials on a substrate characterised by the treatment performed before or after the formation of the layer post-treatment
    • H01L21/02345—Forming insulating materials on a substrate characterised by the treatment performed before or after the formation of the layer post-treatment treatment by exposure to radiation, e.g. visible light
    • H01L21/02351—Forming insulating materials on a substrate characterised by the treatment performed before or after the formation of the layer post-treatment treatment by exposure to radiation, e.g. visible light treatment by exposure to corpuscular radiation, e.g. exposure to electrons, alpha-particles, protons or ions
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • 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
    • H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
    • H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic Table or AIIIBV compounds with or without impurities, e.g. doping materials
    • H01L21/30—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26
    • H01L21/31—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26 to form insulating layers thereon, e.g. for masking or by using photolithographic techniques; After treatment of these layers; Selection of materials for these layers
    • H01L21/312—Organic layers, e.g. photoresist
    • H01L21/3121—Layers comprising organo-silicon compounds
    • H01L21/3122—Layers comprising organo-silicon compounds layers comprising polysiloxane compounds
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • 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
    • H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
    • H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic Table or AIIIBV compounds with or without impurities, e.g. doping materials
    • H01L21/30—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26
    • H01L21/31—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26 to form insulating layers thereon, e.g. for masking or by using photolithographic techniques; After treatment of these layers; Selection of materials for these layers
    • H01L21/314—Inorganic layers
    • H01L21/316—Inorganic layers composed of oxides or glassy oxides or oxide based glass
    • H01L21/31604—Deposition from a gas or vapour
    • H01L21/31633—Deposition of carbon doped silicon oxide, e.g. SiOC

Definitions

  • the present invention relates to a process for producing a polymer. More particularly, the invention relates to a polymer suitably used for an interlayer dielectric for semiconductor devices and the like, a process for producing the same, an insulating-film-forming composition, an insulating film, and a method of forming the same.
  • a silica (SiO 2 ) film formed by a vacuum process such as chemical vapor deposition (CVD) has been widely used as an interlayer dielectric for semiconductor devices and the like.
  • a coating-type insulating film called a spin-on-glass (SOG) film which contains a tetraalkoxysilane hydrolyzate as the major component, has also been used in order to form an interlayer dielectric with a more uniform thickness.
  • SOG film a low-relative-dielectric-constant interlayer dielectric, which contains a polyorganosiloxane as the major component, has been developed.
  • JP-A-2001-127152 proposes a method which includes preparing a coating liquid by mixing a polycarbosilane solution and a polysiloxane solution and forming a low-dielectric-constant insulating film using the resulting coating liquid.
  • this method has a problem in which the carbosilane domains and the siloxane domains are nonuniformly dispersed in the resulting coating.
  • a semiconductor device manufacturing process involves a chemical mechanical planarization (CMP) step for planarizing an insulating layer and various cleaning (washing) steps. Therefore, a material used for an interlayer dielectric or a protective film for semiconductor devices is required to exhibit mechanical strength and chemical resistance against chemical corrosion in addition to the dielectric constant characteristics.
  • CMP chemical mechanical planarization
  • An object of the invention is to provide a polymer which may be suitably used for semiconductor devices and the like for which an increase in the degree of integration and the number of layers has been demanded and may form an insulating film exhibiting a low relative dielectric constant and excellent chemical resistance, and a process for producing the same.
  • Another object of the invention is to provide an insulating-film-forming composition using the polymer according to the invention, a method of forming an insulating film, and an insulating film.
  • a process for producing a polymer according to one aspect of the invention comprises mixing (A) a polysiloxane compound and (B) a polycarbosilane compound in the presence of a catalyst, water, and an organic solvent, and heating the mixture.
  • the polycarbosilane compound (B) may be a polycarbosilane compound having a structure of the following general formula (1),
  • R 8 represents a group selected from the group consisting of a hydrogen atom, a halogen atom, a hydroxyl group, an alkoxy group, an acyloxyl group, a sulfone group, a methanesulfone group, a trifluoromethanesulfone group, an alkyl group, an alkenyl group, and an aryl group
  • R 9 represents a group selected from the group consisting of a halogen atom, a hydroxyl group, an alkoxy group, an acyloxyl group, a sulfone group, a methanesulfone group, a trifluoromethanesulfone group, an alkyl group, an alkenyl group, and an aryl group
  • R 10 and R 11 individually represent groups selected from the group consisting of a halogen atom, a hydroxyl group, an alkoxy group, an acyloxyl group, a sulfone group,
  • the component (A) may be obtained by hydrolyzing and condensing a hydrolyzable-group-containing silane compound, and the component (B) may be used in an amount of 1 to 1,000 parts by weight for 100 parts by weight of the component (A) as a complete hydrolysis-condensation product.
  • the component (B) may have a polystyrene-reduced weight average molecular weight of 400 to 50,000.
  • the catalyst may be an acid catalyst, a base catalyst, or a metal catalyst.
  • the catalyst may be used in an amount of 0.001 to 100 parts by weight for 100 parts by weight of the component (A) and the component (B) in total.
  • the water may be used in an amount of 0.1 to 100 parts by weight for 100 parts by weight of the component (A) and the component (B) in total.
  • a polymer in which the polysiloxane and the polycarbosilane are reacted can be obtained by mixing the polysiloxane compound (A) and the polycarbosilane compound (B) in the presence of the catalyst, water, and organic solvent and heating the mixture.
  • the resulting polymer does not undergo phase separation, which may occur when blending a polysiloxane solution and a polycarbosilane solution.
  • a polymer film which exhibits a low relative dielectric constant and excellent chemical resistance can be obtained by using an insulating-film-forming composition including such a specific polymer.
  • a polymer according to one aspect of the invention is obtained by the above-described process for producing a polymer.
  • a polymer-film-forming composition according to one aspect of the invention includes the above-described polymer and an organic solvent.
  • a method of forming a polymer film according to one aspect of the invention may include applying the insulating-film-forming composition to a substrate, and heating the applied composition at 30 to 500° C.
  • An insulating film according to one aspect of the invention is obtained by the method of forming an insulating film.
  • the above-described insulating film exhibits a low relative dielectric constant and excellent chemical resistance, as described above. Therefore, the insulating film may be suitably used as an interlayer dielectric for semiconductor devices.
  • the process for producing a polymer according to one embodiment of the invention includes mixing the polysiloxane compound (A) (hereinafter may be called “component (A)”) and the polycarbosilane compound (B) (hereinafter may be called “component (B)”) in the presence of a catalyst, water, and an organic solvent, and heating the mixture.
  • component (A) polysiloxane compound
  • component (B) polycarbosilane compound
  • the Si—OH group in the polycarbosilane compound (B) and the Si—OH group in the polysiloxane compound (A) are condensed by mixing the polysiloxane compound (A) and the polycarbosilane compound (B) in the presence of a catalyst, water, and an organic solvent and heating the mixture, whereby formation of a polysiloxane-polycarbosilane composite structure progresses. This produces a polymer which does not undergo phase separation.
  • an Si—OH group can be introduced into the polycarbosilane compound (B) by mixing the polysiloxane compound (A) and the polycarbosilane compound (B) in the presence of a catalyst, water, and an organic solvent and heating the mixture.
  • the polysiloxane compound (A) may be a compound obtained by hydrolyzing and condensing a hydrolyzable-group-containing silane compound.
  • hydrolyzable group used herein refers to a group which may be hydrolyzed. Specific examples of the hydrolyzable group include a hydrogen atom bonded to a silicon atom, a halogen atom, a hydroxyl group, alkoxy group, acyloxy group, sulfone group, methanesulfone group, and trifluoromethanesulfone group. Note that the hydrolyzable group is not limited to these groups.
  • a polysiloxane compound may be used which is obtained by hydrolyzing and condensing at least one silane compound selected from the group consisting of a compound of the following general formula (2) (hereinafter called “compound 2”), a compound of the following general formula (3) (hereinafter called “compound 3”), and a compound of the following general formula (4) (hereinafter called “compound 4”), R a Si(OR 1 ) 4-a (2)
  • R represents a hydrogen atom, a fluorine atom, or a monovalent organic group
  • R 1 represents a monovalent organic group
  • a represents an integer from 1 to 3, Si(OR 2 ) 4 (3)
  • R 2 represents a monovalent organic group
  • R 6 c represents a monovalent organic group
  • R 3 to R 6 individually represent monovalent organic groups, b and c individually represent integers from 0 to 2, R 7 represents an oxygen atom, a phenylene group, or a group —(CH 2 ) m — (wherein m represents an integer from 1 to 6), and d represents 0 or 1.
  • the monovalent organic group represented by R and R 1 in the general formula (2) an alkyl group, alkenyl group, aryl group, and the like can be given. It is preferable that the monovalent organic group represented by R 1 in the general formula (2) be an alkyl group, alkenyl group, or phenyl group. As examples of the alkyl group, a methyl group, ethyl group, propyl group, butyl group, and the like can be given.
  • the alkyl group preferably has 1 to 5 carbon atoms. These alkyl groups may be either linear or branched, in which a hydrogen atom may be replaced with a fluorine atom or the like.
  • alkenyl group in the general formula (2) a vinyl group, allyl group, and the like can be given.
  • aryl group in the general formula (2) a phenyl group, naphthyl group, methylphenyl group, ethylphenyl group, chlorophenyl group, bromophenyl group, fluorophenyl group, and the like can be given.
  • methyltrimethoxysilane, methyltriethoxysilane, methyltri-n-propoxysilane, methyltri-iso-propoxysilane, ethyltrimethoxysilane, ethyltriethoxysilane, vinyltrimethoxysilane, vinyltriethoxysilane, phenyltrimethoxysilane, phenyltriethoxysilane, dimethyldimethoxysilane, dimethyldiethoxysilane, diethyldimethoxysilane, diethyldiethoxysilane, diphenyldimethoxysilane, diphenyldiethoxysilane, and the like are preferable as the compound 2.
  • the monovalent organic groups illustrated for the general formula (2) can be given.
  • tetramethoxysilane, tetraethoxysilane, tetra-n-propoxysilane, tetra-iso-propoxysilane, tetra-n-butoxysilane, tetra-sec-butoxysilane, tetra-tert-butoxysilane, tetraphenoxysilane, and the like can be given.
  • tetramethoxysilane and tetraethoxysilane are preferable. These compounds may be used either individually or in combination of two or more.
  • the compounds 2 to 4 may be used either individually or in combination of two or more.
  • the polystyrene-reduced weight average molecular weight of the polysiloxane compound is preferably 100 to 100,000, and still more preferably 1,000 to 100,000.
  • the term “complete hydrolysis-condensation product” used herein refers to a product in which the groups represented by R 1 O—, R 2 O—, R 4 O—, and R 5 O— in the siloxane compounds are completely hydrolyzed to form OH groups and are completely condensed.
  • a catalyst may be used when producing the polysiloxane compound, if necessary.
  • the catalyst an organic acid, inorganic acid, organic base, inorganic base, metal chelate, and the like can be given.
  • organic acid examples include acetic acid, propionic acid, butanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, oxalic acid, maleic acid, methylmalonic acid, adipic acid, sebacic acid, gallic acid, butyric acid, mellitic acid, arachidonic acid, shikimic acid, 2-ethylhexanoic acid, oleic acid, stearic acid, linolic acid, linoleic acid, salicylic acid, benzoic acid, p-aminobenzoic acid, p-toluenesulfonic acid, benzenesulfonic acid, monochloroacetic acid, dichloroacetic acid, trichloroacetic acid, trifluoroacetic acid, formic acid, malonic acid, phthalic acid, fumaric acid,
  • inorganic acid hydrochloric acid, nitric acid, sulfuric acid, hydrofluoric acid, phosphoric acid, and the like can be given.
  • inorganic base ammonia, sodium hydroxide, potassium hydroxide, barium hydroxide, calcium hydroxide, and the like can be given.
  • methanolamine, ethanolamine, propanolamine, butanolamine N-methylmethanolamine, N-ethylmethanolamine, N-propylmethanolamine, N-butylmethanolamine, N-methylethanolamine, N-ethylethanolamine, N-propylethanolamine, N-butylethanolamine, N-methylpropanolamine, N-ethylpropanolamine, N-propylpropanolamine, N-butylpropanolamine, N-methylbutanolamine, N-ethylbutanolamine, N-propylbutanolamine, N-butylbutanolamine, N,N-dimethylmethanolamine, N,N-diethylmethanolamine, N,N-dipropylmethanolamine, N,N-dibutylmetanolamine, N,N-dimethylethanolamine, N,N-diethylethanolamine, N,N-dipropylm
  • titanium chelate compounds such as
  • the catalyst is used in an amount of usually 0.0001 to 1 mol, and preferably 0.001 to 0.1 mol for one mol of the compounds 2 to 4 in total.
  • a polycarbosilane compound having a structure of the following general formula (1) (hereinafter called “compound 1”) may be used as the polycarbosilane compound (B),
  • R 8 represents a group selected from the group consisting of a hydrogen atom, a halogen atom, a hydroxyl group, an alkoxy group, an acyloxyl group, a sulfone group, a methanesulfone group, a trifluoromethanesulfone group, an alkyl group, an alkenyl group, and an aryl group
  • R 9 represents a group selected from the group consisting of a halogen atom, a hydroxyl group, an alkoxy group, an acyloxyl group, a sulfone group, a methanesulfone group, a trifluoromethanesulfone group, an alkyl group, an alkenyl group, and an aryl group
  • R 10 and R 11 individually represent groups selected from the group consisting of a halogen atom, a hydroxyl group, an alkoxy group, an acyloxyl group, a sulfone group,
  • R 12 to R 14 individually represent a substituted or unsubstituted methylene group, a substituted or unsubstituted alkylene group, a substituted or unsubstituted alkenylene group, or a substituted or unsubstituted arylene group.
  • the alkylene group a methylene group, ethylene group, propylene group, butylene group, hexylene group, decylene group, and the like can be given.
  • the alkylene group preferably has 1 to 6 carbon atoms.
  • the alkylene group may be either linear, branched, or cyclic.
  • a hydrogen atom in the alkylene group may be replaced with a fluorine atom or the like.
  • alkenylene group an ethenylene group, propenylene group, 1-butenylene group, 2-butenylene group, and the like can be given.
  • the alkenylene group may be a dienylene group.
  • the alkenylene group preferably has 1 to 4 carbon atoms.
  • a hydrogen atom in the alkenylene group may be replaced with a fluorine atom or the like.
  • arylene group a phenylene group, naphthylene group, and the like can be given.
  • a hydrogen atom in the arylene group may be replaced with a fluorine atom or the like.
  • x, y, and z individually represent integers from 0 to 10,000 which satisfy “5 ⁇ x+y+z ⁇ 10,000”. If “x+y+z” is less than 5, the resulting insulating-film-forming composition may exhibit inferior storage stability. if “x+y+z” is greater than 10,000, the component (B) may be separated from the component (A), whereby a uniform film may not be formed.
  • x, y, and z be respectively “0 ⁇ x ⁇ 800”, “0 ⁇ y ⁇ 500”, and “0 ⁇ z ⁇ 1,000”, more preferably “0 ⁇ x ⁇ 500”, “0 ⁇ y ⁇ 300”, and “0 ⁇ z ⁇ 500”, and still more preferably “0 ⁇ x ⁇ 100”, “0 ⁇ y ⁇ 50”, and “0 ⁇ z ⁇ 100”.
  • x, y, and z satisfy “5 ⁇ x+y+z ⁇ 1,000”, more preferably “5 ⁇ x+y+z ⁇ 500”, still more preferably “5 ⁇ x+y+z ⁇ 250”, and most preferably “5 ⁇ x+y+z ⁇ 100”.
  • R 9 , R 10 , and R 11 is a hydrogen atom, a hydroxyl group, an alkoxy group, an acyloxyl group, a sulfone group, a methanesulfone group, or a trifluoromethanesulfone group.
  • component (B) to include an Si—OH group or a functional group which produces an Si—OH group by hydrolysis, and allows the Si—OH group or the functional group to be condensed with the Si—OH group in the component (A), whereby formation of a composite structure progresses.
  • the component (B) may have a polystyrene-reduced weight average molecular weight of 400 to 50,000.
  • the component (A) when the component (A) is a compound obtained by hydrolyzing and condensing a hydrolyzable-group-containing silane compound, the component (B) may be used in an amount of 1 to 1,000 parts by weight for 100 parts by weight of the component (A) as a complete hydrolysis-condensation product.
  • the polycarbosilane compound (B) may further include the following structural units (5) to (7),
  • R 15 represents a group selected from the group consisting of a hydrogen atom, a halogen atom, a hydroxyl group, an alkoxy group, an acyloxyl group, a sulfone group, a methanesulfone group, and a trifluoromethanesulfone group,
  • R 16 to R 18 individually represent groups similar to R 15 .
  • the molecules of the component (B) preferably include the structural unit (5) in an amount of 5 to 20 mol % (still more preferably 10 to 15 mol %), the structural unit (6) in an amount of 1 to 15 mol % (still more preferably 5 to 10 mol %), and the structural unit (7) in an amount of 30 to 50 mol % (still more preferably 35 to 45 mol %).
  • the number of silicon atoms in the component (B) is preferably 5 to 200, more preferably 5 to 50, and still more preferably 5 to 15.
  • the ratio of the structural units and the number of silicon atoms in the component (B) may be estimated from 29 Si—NMR spectrum analysis results and the polystyrene-reduced weight average molecular weight, for example.
  • the polysiloxane compound (A) described in “1.1. Polysiloxane compound” and the polycarbosilane compound (B) described in “1.2. Polycarbosilane compound” are used in a state in which these compounds are dissolved or dispersed in an organic solvent.
  • the total concentration of the component (A) and the component (B) in the organic solvent is preferably 1 to 30 wt %.
  • organic solvent which may be used in the process for producing a polymer
  • at least one solvent selected from the group consisting of an alcohol solvent, ketone solvent, amide solvent, ether solvent, ester solvent, aliphatic hydrocarbon solvent, aromatic solvent, and halogen-containing solvent may be used.
  • monohydric alcohols such as methanol, ethanol, n-propanol, iso-propanol, n-butanol, iso-butanol, sec-butanol, t-butanol, n-pentanol, iso-pentanol, 2-methylbutanol, sec-pentanol, t-pentanol, 3-methoxybutanol, n-hexanol, 2-methylpentanol, sec-hexanol, 2-ethylbutanol, sec-heptanol, 3-heptanol, n-octanol, 2-ethylhexanol, sec-octanol, n-nonyl alcohol, 2,6-dimethyl-4-heptanol, n-decanol, sec-undecyl alcohol, trimethylnonyl alcohol, sec-tetradecyl alcohol, trimethylnon
  • These alcohol solvents may be used either individually or in combination of two or more.
  • ketone solvent acetone, methyl ethyl ketone, methyl n-propyl ketone, methyl n-butyl ketone, diethyl ketone, methyl i-butyl ketone, methyl n-pentyl ketone, ethyl n-butyl ketone, methyl n-hexyl ketone, di-i-butyl ketone, trimethylenonane, cyclopentanone, cyclohexanone, cycloheptanone, cyclooctanone, 2-hexanone, methylcyclohexanone, 2,4-pentanedione, acetonylacetone, diacetone alcohol, acetophenone, fenchone, and the like can be given.
  • ketone solvents may be used either individually or in combination of two or more.
  • nitrogen-containing solvents such as N,N-dimethylimidazolidinone, N-methylformamide, N,N-dimethylformamide, N,N-dimethylformamide, acetamide, N-methylacetamide, N,N-dimethylacetamide, N-methylpropioneamide, N-methylpyrrolidone, and the like can be given.
  • amide solvents may be used either individually or in combination of two or more.
  • ether solvent ethyl ether, i-propyl ether, n-butyl ether, n-hexyl ether, 2-ethylhexyl ether, ethylene oxide, 1,2-propylene oxide, dioxolane, 4-methyl dioxolane, dioxane, dimethyl dioxane, ethylene glycol monomethyl ether, ethylene glycol dimethyl ether, ethylene glycol monoethyl ether, ethylene glycol diethyl ether, ethylene glycol mono-n-butyl ether, ethylene glycol mono-n-hexyl ether, ethylene glycol monophenyl ether, ethylene glycol mono-2-ethyl butyl ether, ethylene glycol dibutyl ether, diethylene glycol monomethyl ether, diethylene glycol dimethyl ether, diethylene glycol monoethyl ether, diethylene glycol diethyl ether, diethylene glycol mono-n-butyl ether,
  • ether solvents may be used either individually or in combination of two or more.
  • ester solvent diethyl carbonate, propylene carbonate, methyl acetate, ethyl acetate, gamma-butyrolactone, gamma-valerolactone, n-propyl acetate, i-propyl acetate, n-butyl acetate, i-butyl acetate, sec-butyl acetate, n-pentyl acetate, sec-pentyl acetate, 3-methoxybutyl acetate, methylpentyl acetate, 2-ethylbutyl acetate, 2-ethylhexyl acetate, benzyl acetate, cyclohexyl acetate, methylcyclohexyl acetate, n-nonyl acetate, methyl acetoacetate, ethyl acetoacetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl acetate
  • ester solvents may be used either individually or in combination of two or more.
  • n-pentane, i-pentane, n-hexane, i-hexane, n-heptane, i-heptane, 2,2,4-trimethylpentane, n-octane, i-octane, cyclohexane, methylcyclohexane, and the like can be given.
  • aliphatic hydrocarbon solvents may be used either individually or in combination of two or more.
  • aromatic hydrocarbon solvent examples include benzene, toluene, xylene, ethylbenzene, trimethylbenzene, methylethylbenzene, n-propylebenzene, i-propylebenzene, diethylbenzene, i-butylbenzene, triethylbenzene, di-i-propylbenzene, n-amylnaphthalene, trimethylbenzene, and the like can be given.
  • aromatic hydrocarbon solvents may be used either individually or in combination of two or more.
  • halogen-containing solvent examples include dichloromethane, chloroform, fluorocarbon, chlorobenzene, dichlorobenzene, and the like.
  • an organic solvent having a boiling point of less than 250° C is preferable to use.
  • the organic solvent is preferably the ketone solvent, ester solvent, or aromatic hydrocarbon solvent. It is preferable to use one or more of these solvents.
  • a catalyst may be used.
  • the catalysts described in “1.1.4. Catalyst”, which may be used when producing the polysiloxane compound (A), can be given.
  • the catalyst is used in an amount of preferably 0.001 to 100 parts by weight, more preferably 0.005 to 50 parts by weight, and still more preferably 0.01 to 10 parts by weight for 100 parts by weight of the component (A) and the component (B) in total. If the amount of the catalyst is less than 0.001 parts by weight, the component (A) and the component (B) may not sufficiently form a composite structure, whereby the resulting coating may undergo phase separation. If the amount of the catalyst exceeds 100 parts by weight, the component (A) and the component (B) may rapidly undergo a composite structure formation reaction, whereby gelation may occur.
  • water is used in an amount of preferably 0.1 to 100 parts by weight, more preferably 0.1 to 50 parts by weight, and still more preferably 1 to 20 parts by weight for 100 parts by weight of the component (A) and the component (B) in total.
  • water is used in an amount of 0.1 to 100 parts by weight, a film exhibiting improved chemical resistance while maintaining a low relative dielectric constant can be obtained.
  • the component (B) is used in an amount of preferably 1 to 1,000 parts by weight, and still more preferably 5 to 50 parts by weight for 100 parts by weight of the component (A) as a complete hydrolysis-condensation product.
  • a film exhibiting improved chemical resistance while maintaining a low relative dielectric constant can be obtained by using the component (B) in an amount in the above range with respect to the component (A).
  • an organic polymer, a surfactant, and the like may be added to the liquid material obtained by the process described in “1. Process for producing polymer”, in which the polymer is dissolved or dispersed in the organic solvent.
  • organic solvent may be further added to the above liquid material.
  • organic solvent the organic solvents described in “1.3. Organic solvent” can be given.
  • the organic solvent to be added may be the same as the organic solvent used in the above-described process for producing a polymer.
  • the organic solvent used to produce the polymer may be replaced with a desired organic solvent, or a desired organic solvent may be added to the organic solvent used to produce the polymer after producing the polymer.
  • organic polymer a polymer having a sugar chain structure, vinyl amide polymer, (meth)acrylic polymer, aromatic vinyl compound polymer, dendrimer, polyimide, polyamic acid, polyarylene, polyamide, polyquinoxaline, polyoxadizole, fluorine-containing polymer, polymer having a polyalkylene oxide structure, and the like can be given.
  • polyalkylene oxide structure a polymethylene oxide structure, polyethylene oxide structure, polypropylene oxide structure, polytetramethylene oxide structure, polybutylene oxide structure, and the like can be given.
  • ether compounds such as polyoxymethylene alkyl ether, polyoxyethylene alkyl ether, polyoxyethylene alkylphenyl ether, polyoxyethylene sterol ether, polyoxyethylene lanolin derivatives, ethylene oxide derivatives of alkylphenol formalin condensate, polyoxyethylene polyoxypropylene block copolymers, and polyoxyethylene polyoxypropylene alkyl ethers; ether-ester compounds such as polyoxyethylene glyceride, polyoxyethylene sorbitan fatty acid ester, polyoxyethylene sorbitol fatty acid ester, and polyoxyethylene fatty acid alkanolamide sulfate; and ester compounds such as polyethylene glycol fatty acid ester, ethylene glycol fatty acid ester, fatty acid monoglyceride, polyglycerol fatty acid ester, sorbitan fatty acid ester, propylene glycol fatty acid ester, and sucrose fatty acid ester,
  • the ether compounds such as a polyoxyethylene alkyl ether, polyoxyethylene-polyoxypropylene block copolymer, polyoxyethylene polyoxypropylene alkyl ether, polyoxyethylene glyceride, polyoxyethylene sorbitan fatty acid ester, and polyoxyethylene sorbitol fatty acid ester are preferable.
  • organic polymers may be used either individually or in combination of two or more.
  • a nonionic surfactant an anionic surfactant, a cationic surfactant, an amphoteric surfactant, and the like can be given.
  • Specific examples include a fluorine-containing surfactant, a silicone surfactant, a polyalkylene oxide surfactant, a poly(meth)acrylate surfactant, and the like. Of these, the fluorine-containing surfactant and the silicone surfactant are preferable.
  • fluorine-containing surfactant compounds in which at least the terminal, main chain, or side chain includes a fluoroalkyl or fluoroalkylene group, such as 1,1,2,2-tetrafluorooctyl (1,1,2,2-tetrafluoropropyl) ether,
  • Fluorad FC-430, FC-431 manufactured by Sumitomo 3M, Ltd.
  • Asahi Guard AG710 Surflon S-382, SC-101, SC-102, SC-103, SC-104, SC-105, SC-106 (manufactured by Asahi Glass Co., Ltd.)
  • BM-1000, BM-1100 manufactured by BM Chemie
  • NBX-15 manufactured by NEOS Co., Ltd.
  • Megafac F172, BM-1000, BM-1100, and NBX-15 are preferable.
  • SH7PA, SH21PA, SH28PA, SH30PA, ST94PA manufactured by Toray-Dow Corning Silicone Co., Ltd.
  • SH28PA and SH30PA are preferable.
  • the surfactant is used in an amount of usually 0.00001 to 1 part by weight for 100 parts by weight of the polymer formed of the component (A) and the component (B).
  • surfactants may be used either individually or in combination of two or more.
  • the insulating film according to one embodiment of the invention may be obtained by applying the insulating-film-forming composition described in “2. Insulating-film-forming composition” to a substrate to form a coating, and heating the coating and/or applying high energy rays to the coating.
  • the insulating-film-forming composition When applying the insulating-film-forming composition to a substrate such as a silicon wafer, SiO 2 wafer, or SiN wafer, the insulating-film-forming composition is applied by spin coating, dip coating, roll coating, spraying, or the like.
  • a coating with a dry thickness of about 0.05 to 2.5 micrometers may be obtained by single application, and a coating with a dry thickness of about 0.1 to 5.0 micrometers may be obtained by double application.
  • the coating is then dried at an ordinary temperature or dried by heating at usually 80 to 600° C., preferably 30 to 500° C., and still more preferably 60 to 430° C. for about 5 to 240 minutes to form a glass-like or high-molecular-weight polymer coating.
  • the heating means a hot plate, oven, furnace, or the like may be used.
  • the coating may be heated in air, nitrogen, or argon, under vacuum, or under reduced pressure in which the oxygen concentration is controlled, for example.
  • the coating may be heated stepwise, or the atmosphere may be selected from nitrogen, air, oxygen, reduced pressure, and the like, if necessary.
  • the film-forming composition may be applied to a substrate and heated at 25 to 500° C. and preferably 30 to 450° C., and still more preferably 60 to 430° C. while applying high energy rays.
  • the high energy rays may be at least one type of high energy rays selected from electron beams, ultraviolet rays, and X-rays.
  • the irradiation conditions when using electron beams are given below.
  • the period of time required to cure the coating can be reduced in comparison with the case of curing the coating by applying heat. Therefore, when applying this method to formation of an interlayer dielectric for semiconductor devices, the processing time can be reduced even if single-wafer processing is performed.
  • the following description provides the irradiation conditions when using electron beams as the high energy rays.
  • the energy of electron beams is 0.1 to 50 keV, and preferably 1 to 30 keV, and the dose of electron beams is 1 to 1,000 microcurie/cm 2 , and preferably 10 to 500 microcurie/cm 2 .
  • the energy of electron beams is 0.1 to 50 keV, electron beams can sufficiently enter the coating without passing through the coating to damage the semiconductor element located under the coating.
  • the dose of electron beams is 1 to 1,000 microcurie/cm 2 , a reaction occurs in the entire coating and damage to the coating can be reduced.
  • the substrate temperature during electron beam irradiation is preferably 300 to 500° C., and still more preferably 350 to 420° C. If the substrate temperature is less than 300° C., the coating may not be sufficiently cured. If the substrate temperature is greater than 500° C., the coating may be partially decomposed.
  • the coating may be thermally cured by heating the substrate at 250 to 500° C. before applying electron beams, and electron beams may be applied to the thermally cured coating. This method can reduce nonuniformity of the thickness caused by nonuniform electron beam application (nonuniform dose).
  • electron beams may be applied in an inert gas atmosphere.
  • the inert gas N 2 , He, Ar, Kr, and Xe (preferably He and Ar) can be given.
  • the coating is rarely oxidized by applying electron beams in an inert gas atmosphere, whereby the dielectric constant of the resulting coating can be maintained at a low level.
  • Electron beams may be applied under reduced pressure.
  • the pressure is preferably 1 to 1,000 mTorr, and still more preferably 1 to 200 mTorr.
  • ultraviolet rays may be used instead of electron beams.
  • the irradiation conditions when using ultraviolet rays are as follows.
  • ultraviolet rays having a wavelength of preferably 100 to 260 nm, and still more preferably 150 to 260 nm are applied.
  • the insulating film according to this embodiment of the invention includes a number of silicon-carbon bonds in the film structure. Since the polymer according to this embodiment of the invention has a polysiloxane-polycarbosilane composite structure obtained by condensing the polysiloxane compound (A) and the polycarbosilane compound (B), the polymer does not undergo phase separation, which may occur when blending a polysiloxane solution and a polycarbosilane solution, whereby a uniform film can be obtained.
  • An insulating film which exhibits a low relative dielectric constant, excellent mechanical strength, CMP resistance, and chemical resistance can be obtained by using a film-forming composition including the polymer according to this embodiment of the invention.
  • the insulating film exhibits a low relative dielectric constant and excellent mechanical strength, CMP resistance, and chemical resistance
  • the insulating film is useful for applications such as an interlayer dielectric for semiconductor devices such as an LSI, system LSI, DRAM, SDRAM, RDRAM, and D-RDRAM, an etching stopper film, a protective film (e.g. surface coating film) for semiconductor devices, an intermediate layer used in the semiconductor manufacturing process using a multilayer resist, an interlayer dielectric for multilayer wiring boards, and a protective film or an insulating film for liquid crystal display devices.
  • An aluminum electrode pattern was formed on the resulting polymer film by deposition to prepare a relative dielectric constant measurement sample.
  • the relative dielectric constant of the polymer film was measured at room temperature by a CV method at a frequency of 100 kHz using an electrode “HP16451B” and a precision LCR meter “HP4284A” manufactured by Yokogawa-Hewlett-Packard, Ltd.
  • a polymer film having a residual film rate (defined below) of 99% or more was determined to exhibit excellent chemical resistance (“A” in Table 1), and a polymer film having a residual film rate of less than 99% was determined to exhibit poor chemical resistance (“B” in Table 1).
  • Residual film rate (%) (thickness after immersion)/(thickness before immersion) ⁇ 100
  • composition (A-2) obtained in Example 1 was applied to an 8-inch silicon wafer by spin coating.
  • the applied composition (solution) was heated at 80° C. for five minutes in air, at 200° C. for five minutes in nitrogen, at 340° C., 360° C., and 380° C. for 30 minutes, respectively, under vacuum, and at 425° C. for one hour under vacuum to form a transparent colorless coating.
  • the relative dielectric constant and the chemical resistance of the coating were measured according to the evaluation methods described in “4.1. Evaluation method”. The results are shown in Table 1.
  • composition (A-2) obtained in Example 1 was applied to an 8-inch silicon wafer by spin coating to obtain a coating with a thickness of 0.5 micrometers.
  • the coating was heated at 80° C. for five minutes in air and at 200° C. for five minutes in nitrogen.
  • electron beams were applied to the coating in a helium (He) atmosphere at an acceleration voltage of 5 keV, a hot plate temperature of 400° C., and a pressure of 1.33 Pa to form an insulating film.
  • the relative dielectric constant and the chemical resistance of the insulating film were measured according to the evaluation methods described in “4.1. Evaluation method”. The results are shown in Table 1.

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