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WO2001079325A1 - Composition de resine photosensible - Google Patents

Composition de resine photosensible Download PDF

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Publication number
WO2001079325A1
WO2001079325A1 PCT/JP2001/003296 JP0103296W WO0179325A1 WO 2001079325 A1 WO2001079325 A1 WO 2001079325A1 JP 0103296 W JP0103296 W JP 0103296W WO 0179325 A1 WO0179325 A1 WO 0179325A1
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Prior art keywords
group
alicyclic olefin
olefin polymer
acid
polymerizable unsaturated
Prior art date
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PCT/JP2001/003296
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English (en)
Japanese (ja)
Inventor
Junji Kodemura
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Zeon Corporation
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Priority to JP2001576916A priority Critical patent/JP3928702B2/ja
Publication of WO2001079325A1 publication Critical patent/WO2001079325A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L51/00—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
    • C08L51/003—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers grafted on to macromolecular compounds obtained by reactions only involving unsaturated carbon-to-carbon bonds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F255/00—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F277/00—Macromolecular compounds obtained by polymerising monomers on to polymers of carbocyclic or heterocyclic monomers as defined respectively in group C08F32/00 or in group C08F34/00
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F285/00—Macromolecular compounds obtained by polymerising monomers on to preformed graft polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • 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
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
    • 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
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
    • C08G61/04—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms
    • C08G61/06—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms prepared by ring-opening of carbocyclic compounds
    • C08G61/08—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms prepared by ring-opening of carbocyclic compounds of carbocyclic compounds containing one or more carbon-to-carbon double bonds in the ring

Definitions

  • the present invention relates to a photosensitive composition. More specifically, a material for forming a protective film or the like used for an electronic component or an interlayer insulating film, particularly, a material for forming an interlayer insulating film or the like of a liquid crystal display device, an integrated circuit device, a solid-state imaging device, or the like.
  • the present invention relates to a photosensitive resin composition having a low dielectric constant, which is suitable as a photosensitive resin composition.
  • thermosetting materials for forming an insulating film require many steps to obtain an interlayer insulating film having a desired pattern shape, and the obtained interlayer insulating film has sufficient flatness. There were things I could't do. Therefore, development of a new photosensitive insulating film forming material capable of fine patterning has been required. In recent years, as the density of wirings and devices has increased, low dielectric constants have been required for these materials.
  • An object of the present invention is to provide a photosensitive resin composition which is excellent in various properties such as flatness, heat resistance, transparency, and chemical resistance, and can easily form a fine patterned thin film having excellent low dielectric properties. Offer things Is to do.
  • the present inventors have studied to achieve the above object, and as a result, use a photosensitive resin composition containing an alicyclic olefin polymer having a polymerizable unsaturated group and an acidic group and a photopolymerization initiator. As a result, they have found that the object of the present invention can be achieved, and have completed the present invention based on this finding.
  • a photosensitive resin composition containing an alicyclic olefin polymer having a polymerizable unsaturated group and an acidic group or an acid derivative type residue and a photopolymerization initiator, and curing the same An insulator is provided.
  • an alicyclic olefin polymer containing an acidic group or an acid derivative type residue is reacted with a compound containing an acidic group or an acid derivative type residue. And then reacting the alicyclic olefin polymer containing an acidic group or an acid derivative type residue with a compound containing a polymerizable unsaturated group, the polymerizable unsaturated group and the acid group or A process for producing an alicyclic olefin polymer having an acid derivative type residue and an alicyclic olefin polymer having a polymerizable unsaturated group and an acidic group or an acid derivative type residue are provided.
  • the photosensitive composition of the present invention includes an alicyclic olefin polymer having a polymerizable unsaturated group and an acidic group or an acid derivative type residue (hereinafter, simply referred to as “polymerizable alicyclic olefin polymer J”). , And a photopolymerization initiator.
  • the polymerizable alicyclic olefin polymer of the present invention is an alicyclic olefin polymer having a polymerizable unsaturated group and an acidic group or an acid derivative type residue. Those containing a large amount of an acid group or an acid derivative type residue are dissolved by an alkaline solution.
  • the alicyclic olefin polymer is a polymer of an olefin having an alicyclic structure.
  • the alicyclic structure include a cycloalkane structure and a cycloargen structure. From the viewpoints of mechanical strength, heat resistance, and the like, a cycloalkane structure, particularly a norpolnane structure, is preferable.
  • examples of the alicyclic structure include a monocyclic ring and a polycyclic ring (such as a condensed polycyclic ring, a bridged ring, and a polycyclic ring obtained by combining these).
  • the number of carbon atoms constituting the alicyclic structure is not particularly limited, but is usually 4 to 30, preferably 5 to 20, and more preferably 5 to 15, Various properties such as mechanical strength, heat resistance and moldability are highly balanced and suitable.
  • the alicyclic compound used in the present invention Refine polymers are usually thermoplastic.
  • the alicyclic olefin polymer usually contains a repeating unit derived from an olefin having an alicyclic structure (hereinafter sometimes referred to as an alicyclic olefin).
  • the proportion of the repeating unit derived from the alicyclic olefin in the alicyclic olefin polymer is appropriately selected according to the purpose of use, but is usually 30 to 100% by weight, preferably 50 to 100% by weight, It is preferably from 70 to "! 00% by weight. When the proportion of the repeating unit derived from alicyclic olefin is too small, heat resistance is inferior.
  • the alicyclic olefin polymer is usually obtained by addition polymerization or ring-opening polymerization of the alicyclic olefin and, if necessary, hydrogenation of the unsaturated bond portion, or addition polymerization of an aromatic olefin. It is obtained by hydrogenating the aromatic ring portion of the polymer.
  • Examples of the alicyclic olefin used to obtain the alicyclic olefin polymer include a bicyclic mouth [2.2.1] 1-hept-2-ene (common name: norpolpenene), 5-methyl-1-bicyclo [2. 2.1] 1 hept-2-ene, 5,5-dimethylbicyclo [2.2.1] 1 hept-2-ene, 5-ethyl-1-bicyclo [2.2.1] 1 hept-2-ene , 5-heptyl-bicyclo [2.2.1] 1-hepto-2-ene, 5-hexylubicyclo [2.2.1] 1-hepto-2-ene, 5-octyl-bicyclo [2.2.
  • aromatic olefin examples include styrene, monomethylstyrene, divinylbenzene, vinyl naphthalene, and vinyl toluene.
  • the alicyclic olefin and / or the aromatic olefin can be used alone or in combination of two or more.
  • the alicyclic olefin polymer may be obtained by copolymerizing the alicyclic olefin and / or the aromatic olefin and a monomer copolymerizable therewith.
  • Monomers copolymerizable with alicyclic olefins or aromatic olefins include ethylene, propylene, 1-butene, 11-pentene, 11-hexene, 3-methyl-1-butene and 3-methyl-1-olefin.
  • These monomers can be used alone or in combination of two or more. When these copolymerizable monomers are used for ring-opening polymerization, they may function as a molecular weight regulator.
  • the method for polymerizing alicyclic or aromatic ore-fins and the method for hydrogenation as required are not particularly limited, and can be carried out according to known methods.
  • alicyclic olefin polymer examples include a ring-opened polymer of a norbornene-based monomer and a hydrogenated product thereof, an addition polymer of a norbornene-based monomer, and an addition weight of a norpolene-based monomer and a vinyl compound.
  • Coalesce, monocyclic cycloargen polymer, alicyclic conjugated diene polymer, vinyl alicyclic carbonization Examples include a hydrogen polymer and a hydrogenated product thereof, and an aromatic ring hydrogenated product of an aromatic olefin polymer.
  • a ring-opening polymer of a norponene-based monomer and a hydrogenated product thereof an addition polymer of a norpol- ene-based monomer, an addition polymer of a norpol- ene-based monomer and a vinyl compound, an aromatic olefin polymer
  • the hydrogenated product of a ring-opening polymer of a norpoleneene-based monomer having a repeating unit represented by the formula (1) is particularly preferred.
  • n is a positive integer
  • m is an integer of 0 to 2.
  • the alicyclic olefin polymers described above can be used alone or in combination of two or more.
  • Examples of the acidic group or acid derivative type residue contained in the polymerizable alicyclic olefin polymer include a carboxyl group, an ester group, an amide group, and those obtained by dehydration-condensation of a lipoxyl group within a molecule or between molecules (hereinafter, referred to as An acid anhydride group) can be exemplified.
  • An acid anhydride group those having a carboxyl group or an amide group, particularly those having both a carboxyl group and an amide group, are preferred.
  • the carboxyl group or amide group is present in the polymer as a repeating unit represented by the formula (2), for example.
  • n is a positive integer
  • m is an integer of 0 to 2.
  • C and D are each independently O H, is an NR 2 or one NHR.
  • R is a monovalent saturated hydrocarbon group.
  • a monomer having the functional group is (co) polymerized as a (co) polymerization component;
  • the method include graft modification of an alicyclic olefin polymer with a compound containing an acidic group or a compound containing an acid derivative type residue by a modification reaction. In the present invention, those obtained by the latter denaturation reaction are preferred.
  • the compound having an acidic group or an acid derivative type residue used in the denaturation reaction include acrylic acid, methacrylic acid, ⁇ -ethylacrylic acid, maleic acid, fumaric acid, itaconic acid, and endcis-bicyclo [2]
  • Unsaturated carboxylic acid compounds such as heptose 5-ene-1,2,3-dicarboxylic acid and methyl-endcis-bicyclo [2.2.1] heptose 5-ene-2,3-dicarboxylic acid and esters thereof Or amides; unsaturated rubonic anhydrides such as maleic anhydride, maleic anhydride, butenyl succinic anhydride, tetrahydrophthalic anhydride, and citraconic anhydride; Of these, maleic anhydride is preferred.
  • the modification reaction between the alicyclic olefin polymer and the compound having an acidic group or an acid derivative type residue can be carried out by a known method.
  • the modification reaction is usually performed by coexisting an alicyclic olefin polymer and a compound having an acidic group or an acid derivative type residue in the presence of a radical initiator.
  • an azo compound may be used as a radical initiator.
  • the azo compound include azobisisobutyronitrile and dimethylazoisobutyrate.
  • organic pero Oxides and organic peresters are preferably used.
  • radical initiators can be used alone or in combination of two or more.
  • the ratio of the radical initiator to be used is usually 0.001 to 50 parts by weight, preferably 0.01 to 40 parts by weight, more preferably 0 to 100 parts by weight, based on 100 parts by weight of the alicyclic olefin polymer. It is in the range of 1 to 30 parts by weight.
  • the conditions for the denaturation reaction are not particularly limited.
  • the reaction temperature is generally 0 to 400 ° C., preferably 60 to 300 ° C., more preferably 80 to 200 ° C.
  • the reaction time ranges usually from 1 minute to 24 hours, preferably from 30 minutes to 10 hours.
  • the modification rate is such that the polymer exhibits alkali solubility.
  • the modification ratio is usually from 10 to 200 mol%, preferably from 30 to 150 mol%, more preferably from 50 to 100 mol%, based on the total number of monomer units in the polymer. It is preferably in the range of 100 mol 0 / o, particularly preferably in the range of 60 to 80 mol%. When the modification ratio is in this range, characteristics such as low dielectric properties, transparency, heat resistance, solvent resistance, developability and surface hardness characteristics are highly balanced and suitable.
  • the denaturation rate is represented by the following equation.
  • X the total number of moles of the modifying group in the polymer by the compound having an acidic group or an acid derivative type residue
  • X is the total number of modified residues in the polymerizable alicyclic olefin polymer, and can be measured by 1 H-NMR.
  • Y is the value obtained by dividing the weight average molecular weight (M w) of the polymer by the molecular weight of the monomer (in the case of a copolymer, the molecular weight of the monomer is the same as the average molecular weight of the monomer mixture) Do).
  • the total amount of the acidic group and the acid derivative type residue is calculated by multiplying the above modification rate by the valency of the compound having the acidic group and the acid derivative type residue.
  • the value obtained by doubling the modification rate is the total amount of the acid group and the acid derivative type residue.
  • the polymerizable alicyclic olefin polymer used in the present invention is a compound obtained by modifying a compound having an acid anhydride group or a compound having an ester group into an alicyclic olefin polymer, the modification reaction It is preferable to hydrolyze or amidate the acid anhydride group or ester group introduced in the above.
  • Compounds used to promote hydrolysis or amidation include potassium hydroxide, sodium hydroxide; trimethylamine, triethylamine, triptylamine, and the like. Of these, metal hydroxides are preferred.
  • Examples of the compound include water; methylamine, ethylamine, butylamine, pentylamine, arylamine, diarylamine, vinylamine; and amines such as dimethylamine and dipropylamine.
  • primary amines particularly primary amines having an unsaturated carbon-carbon bond, are preferred.
  • polymerizable unsaturated group contained in the polymerizable alicyclic olefin polymer of the present invention include a functional group having a carbon-carbon unsaturated double bond.
  • Specific examples include a vinyl group, an aryl group, an acryloyl group, and a methacryloyl group.
  • a (co) polymerization of a monomer having a polymerizable unsaturated group as a (co) polymer component is carried out.
  • a polymerizable unsaturated group-containing compound to an alicyclic olefin polymer obtained by polymerizing the above monomer by a modification reaction.
  • a polymerizable unsaturated group-containing compound to an alicyclic olefin polymer obtained by polymerizing the above monomer by a modification reaction.
  • those obtained by the latter denaturation reaction are preferred.
  • an alicyclic olefin polymer having an acidic group or an acid derivative type residue In order to include a polymerizable unsaturated group in the modification reaction, it is preferable to use an alicyclic olefin polymer having an acidic group or an acid derivative type residue.
  • the presence of an acidic group or an acid derivative type residue makes a compound having a polymerizable unsaturated group more easily undergo a denaturation reaction.
  • Examples of the polymerizable unsaturated group-containing compound used for the modification reaction include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, and 2-hydroxy-3-acrylate.
  • the modification reaction with a compound having a polymerizable unsaturated group can be performed by a known method.
  • the denaturation reaction is usually performed in a dry solvent at a reaction temperature of 0 to 100 ° C, preferably 25 to 80 ° C.
  • an amine-based or phosphorus-based catalyst can be used to promote the reaction.
  • a polymerization inhibitor such as a hydroquinone
  • Examples of the polymerizable alicyclic olefin polymer obtained by a modification reaction with a compound having a polymerizable unsaturated group include those represented by the formula (3).
  • n is a positive integer
  • m is an integer of 0 to 2
  • R is a monovalent hydrocarbon group
  • R 2 is a divalent organic group.
  • Polymerizable alicyclic Orefuin polymer the amount of the polymerizable unsaturated group the total number of monomer units in the polymer as a reference, usually 3-300 mol%, preferably 1 5 to 200 mole 0/0, It is more preferably from 45 to 150 mol 0 / o, particularly preferably from 65 to 100 mol 0 / o.
  • the molecular weight of the polymerizable alicyclic olefin polymer used in the present invention is appropriately selected according to the purpose of use.
  • the weight average molecular weight (Mw) in terms of polystyrene measured by gel permeation chromatography using either toluene, tetrahydrofuran, or chloroform as a solvent is usually 1,000 to 500,000, It is preferably in the range of 2,000 to 100,000, more preferably in the range of 3,000 to 50,000. When the weight-average molecular weight is in this range, it is particularly excellent in developability, flatness, solvent resistance, heat resistance and strength properties, and is suitable.
  • the glass transition temperature of the polymerizable alicyclic olefin polymer used in the present invention is not particularly limited, but is usually 50 ° C or higher, preferably 80 ° C or higher, more preferably 100 ° C or higher. In some cases, it has good heat resistance and is suitable.
  • the photopolymerization initiator used in the present invention is a compound that generates a radical or a cation by light irradiation and initiates a reaction due to a polymerizable unsaturated group.
  • photopolymerization initiators that generate radicals include ⁇ -diketone compounds such as benzyl and diacetyl; acyloin compounds such as benzoin and pivaloin; acyloin compounds such as benzoin methyl ether, benzoin ethyl ether and benzoin isopropyl ether.
  • Ter compounds thioxanthone, 2,4-diethylthioxanthone, thioxanthone-41-sulfonic acid, benzophenone, ⁇ , ⁇ '-tetramethyldiaminobenzophenone, 4,4'-bis (dimethylamino) benzophenone, 4, 4 ' Benzophenone compounds such as 1-bis (getylamino) benzophenone; acetophenone, ⁇ -dimethylaminoacetophenone, a, a 'dimethylethoxyacetoxybenzophenone, 2, 2'-dimethoxy-2-phenylphenyl cetofphenone, p-Methoxyacetophenone, 2-methyl [4- (methylthio) phenyl] -12-molyphorinol 1-propanone, 2-benzyl-2-dimethylamino-1- (4-morifolinophenyl) -butane Acetophenone compounds, such as on; quinone
  • photopolymerization initiators that generate cations include phenyldiazoniumtetrafluoroporate, phenyldiazoniumhexafluorophosphonate, and phenyldiazoniumhexafluoroarcete.
  • Phenyldiazonium trifluoromethanesulfonate fenic Luzazonium trifluoroacetate
  • phenyldiazonium-p-toluenesulfonate 4-methoxyphenyldiazoniumtetrafluoroborate
  • 4-methoxyphenyldiazonium hexaoxafluophosphonate etc.
  • the amount of the photopolymerization initiator is usually 0.1 to 20 parts by weight, preferably 1 to 10 parts by weight, based on 100 parts by weight of the polymerizable alicyclic olefin polymer.
  • composition of the present invention preferably contains a crosslinking agent or a curing agent.
  • the crosslinking agent used in the present invention is a crosslinking compound having a polymerizable unsaturated group.
  • a typical example of the crosslinking agent is a compound having two or more polymerizable unsaturated groups.
  • a crosslinking agent having an alkali-soluble functional group such as a hydroxyl group or a hydroxyl group is preferable because it can enhance the alkali developability of the photosensitive composition.
  • those having an alicyclic structure are also preferable.
  • the amount of the crosslinking agent is usually 1 to 100 parts by weight, preferably 5 to 50 parts by weight, more preferably 10 to 30 parts by weight, based on 100 parts by weight of the polymerizable alicyclic olefin polymer. .
  • the resolution can be improved. It is presumed that these crosslinking agents mainly react with the polymerizable unsaturated groups in the polymerizable alicyclic olefin polymer to form a bridged structure.
  • the curing agent used in the present invention is a compound capable of reacting with a hydroxyl group, an acidic group or an acid derivative type residue.
  • the curing agent Sumidur N-75, Sumidyl N3200, Sumidur HT, Sumidur N3500, Desmodur N3400, Desmodur BL3175, Desmodur E3265 manufactured by Sumitomo discussion Urethane Co., Ltd.
  • Hydrogenated diphenylmethane diisocyanate based polyisocyanate such as diphenyl methane diisocyanate polyisocyanate; Desmodur E27; Desmodur TP LS 21 17; Claren TP LS 2007; Claren TP LS 2122 Isocyanate; epoxy compound, epoxy resin, preferably epoxy compound or resin having an alicyclic structure; N, N, ⁇ ', ⁇ ', ⁇ ", ⁇ "-( Hexaalkoxymethyl) Alkoxymethylated melamines such as melamine; ⁇ , ⁇ ', ⁇ ", ⁇ "'-(tetraalkoxymethyl) glycoxypropyl alkyloxymethylated glycerol; 1,
  • hexamethylene diisocyanate-based polyisocyanates such as Sumidur BL 3175, Desmodur TP LS 2759, Desmodur TP LS 2957, Desmodur TP LS 2062, and Bihydrol 116
  • desmodur Tolylene diisocyanate-based polyisocyanates such as AP Stable, Desmodur CT Stable, Desmodur BL110, Desmodur BL1265, diphenyls such as Desmosam 2170, Desmosam 2265 Methane diisocyanate polyisocyanate, Desmodur TP LS 217, Claren TP LS 2007, Claren TP L
  • Isophorone diisocyanate-based polyisomers such as hydrogenated diphenylmethane diisocyanate-based polyisocyanate such as S2122, Desmodur TPLS 2135, Desmodur TP LS 2078, Claren UI, Claren TP LS2147
  • the amount of the curing agent is usually 1 to 100 parts by weight, preferably 5 to 50 parts by weight, more preferably 10 to 30 parts by weight, based on 100 parts by weight of the polymerizable alicyclic olefin polymer. .
  • the post-curing treatment post-bake treatment
  • the heat resistance and flatness of the cured product of the photosensitive composition can be improved.
  • the photosensitive composition of the present invention may contain a surfactant for the purpose of preventing striation (after coating streaks) and improving developability.
  • surfactant examples include polyoxyethylene alkyl ethers such as polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, and polyoxyethylene oleyl ether; polyoxyethylene octyl phenyl ether, polyoxyethylene Polyoxyethylene aryl ethers such as nonyl phenyl ether; Nonionic surfactants such as polyoxyethylene dialkyl esters such as polyoxyethylene dilaurate and polyoxyethylene distearate; EF301, 303, 352 (manufactured by Shin-Akita Chemical Co., Ltd.), Megafac F171, F172, F172, F173 (manufactured by Dainippon Ink and Chemicals, Inc.), Florard FC—430, FC-431 (manufactured by Sumitomo Sleam Co., Ltd.), Asahi Guard AG710, SAFLON S-382, Fluorosurfactants such as SC-101, SC-102, SC-103, SC-
  • the surfactant is used as needed in an amount of 2 parts by weight or less, preferably 1 part by weight or less, based on 100 parts by weight of the solid content of the photosensitive composition.
  • the photosensitive composition of the present invention may contain an adhesion aid for the purpose of improving the adhesion to the substrate.
  • an adhesion aid include a functional silane coupling agent.
  • the functional silane coupling agent include trimethoxysilyl benzoic acid, Tacryloxypropyltrimethoxysilane, vinyltriacetoxysilane, vinyltrimethoxysilane, r-isocyanatepropyltriethoxysilane, glycidoxypropyltrimethoxysilane, ⁇ - (3,4-epoxycyclohexyl) ethyltrimethoxysilane, etc. No.
  • the amount of the adhesion aid is usually 20 parts by weight or less, preferably 0.05 to 10 parts by weight, particularly preferably 100 parts by weight, based on 100 parts by weight of the alicyclic soluble alicyclic olefin polymer. It is 1 to 10 parts by weight.
  • the photosensitive composition of the present invention may contain a sensitizer, an antistatic agent, a storage stabilizer, an antifoaming agent, a pigment, a dye, a flame retardant, and the like, if necessary.
  • sensitizer examples include carbonyl compounds such as benzanthrone and chloranil; nitro compounds such as nitrobenzene, ⁇ -dinitrobenzene and 2-nitrofluorene; aromatic hydrocarbons such as anthracene and chrysene; and diphenyls such as diphenyl disulfide.
  • carbonyl compounds such as benzanthrone and chloranil
  • nitro compounds such as nitrobenzene, ⁇ -dinitrobenzene and 2-nitrofluorene
  • aromatic hydrocarbons such as anthracene and chrysene
  • diphenyls such as diphenyl disulfide.
  • nitrogen compounds such as nitroaniline, 2-chloro-1,4-troaniline, 5-nitro-2-aminotoluene and tetracyanoethylene.
  • the storage stabilizer examples include hydroxyaromatic compounds such as hydroquinone, methoxyphenol, ⁇ -t-butyl catechol, 2,6-di-t-butyl-p-cresol; quinone compounds such as benzoquinone and P-toluquinone; Phenyl 0; -Aminic compounds such as naphthylamine; 4,4'-Tiobis (6-t-butyl-3-methylphenol), 2,2'-Tiobis (4-methyl-6-t-butylphenol) Sulfur compounds;
  • the photosensitive composition of the present invention can be easily prepared by uniformly mixing the above components, and is usually used in the form of a solution after being dissolved in an appropriate solvent.
  • the solvent examples include alcohols such as methanol, ethanol, propanol, and butanol; cyclic ethers such as tetrahydrofuran and dioxane; cellosolve esters such as methylacetate sorbacetate and ethylethyl sorbacetate; Glycol ethers such as methyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol dimethyl ether, propylene glycol monomethyl ether; propylene glycol methyl ether acetate, propylene glycol propyl Propylene glycol alkyl ether acetates such as ether acetate; benzene, toluene, xy Aromatic hydrocarbons such as emissions; methyl E chill ketone, cyclohexanone, 2-heptanone, 4 Hido Ketones such as xyl 4-methyl-2-pentanone;
  • Non-polar polar solvents such as dimethylformamide and N-methyl-2-pyrrolidone.
  • ketones, glycol ethers or amides are preferably used from the viewpoint of solubility and ease of forming a coating film.
  • the photosensitive composition of the present invention is not particularly limited by the solid concentration, but is usually 5 to 40% by weight. Further, the photosensitive composition solution prepared as described above is preferably used after being filtered using a filter or the like.
  • the photosensitive composition of the present invention can be applied as a solution to the surface of a substrate, and a solvent can be removed by heating to form a coating film.
  • a method of applying the photosensitive composition solution to the substrate surface for example, various methods such as a spray method, a roll coating method, and a spin coating method can be adopted.
  • the coating is then pre-baked.
  • the solvent is volatilized, and a coating film having no fluidity is obtained.
  • the heating conditions vary depending on the type of each component, the mixing ratio, and the like, but are usually about 60 to 120 ° C. for about 10 to 600 seconds.
  • the heated coating film is irradiated with light through a mask having a predetermined pattern, and then heated (Post Exposure Bake: sometimes referred to as PEB treatment) as necessary, and developed with a developer to remove unnecessary portions. Is removed. Performing the PEB treatment may improve the pattern reproducibility.
  • PEB treatment Post Exposure Bake: sometimes referred to as PEB treatment
  • Examples of the developer include sodium hydroxide, potassium hydroxide, sodium carbonate, Inorganic alkalis such as thorium, sodium metasilicate, and ammonia water; primary amines such as ethylamine and n-propylamine; secondary amines such as getylamine and di-n-propylamine; triethylamine, methylethylethylamine, N —Tertiary amines such as methylpyrrolidone; alcohol amines such as dimethylethanolamine and triethanolamine; trimethylammonium hydroxide, tetraethylammonium hydroxide, and tetrabutylammonium hydroxide And quaternary ammonium salts such as choline; pyrrole, piperidine, 1,8-diazabicyclo [5.4.0] -17-indene, 1,5-diazabicyclo [4.3.0] -1-5-nonane And the like.
  • An aqueous solution of cyclic amines such as the above can be used. Further, an aqueous solution obtained by adding an appropriate amount of a water-soluble organic solvent such as methanol or ethanol, a surfactant, or the like to the above-mentioned alkaline aqueous solution can also be used as a developer.
  • a water-soluble organic solvent such as methanol or ethanol, a surfactant, or the like
  • the development time is usually 30 to 180 seconds.
  • the developing method may be any of a paddle method, a liquid filling method, a dive method and the like.
  • the substrate is washed with running water and dried with compressed air or compressed nitrogen to remove moisture on the substrate and form a patterned film.
  • the entire surface of the patterned film is irradiated with a light beam from a high-pressure mercury lamp or the like.
  • a heating device such as a hot plate or an oven is used at a predetermined temperature, for example, 150 to 250 ° C, for a predetermined time, for example, 5 to 30 minutes on a hot plate, and 30 to 9 in an oven.
  • the heat treatment is preferably performed in a low oxygen atmosphere, specifically, an atmosphere having an oxygen concentration of 10 ppm or less.
  • This heat treatment in a low oxygen atmosphere is applicable not only to the photosensitive resin composition of the present invention, but also to other photosensitive resin compositions containing a soluble alicyclic olefin polymer. .
  • the composition obtained by curing the photosensitive composition of the present invention can be used as an insulating material, for example, an electronic element such as a semiconductor element, a light emitting diode, and various kinds of memories; a hybrid IC, an MCM, a printed wiring board, or an electronic component.
  • the hydrogenation rate and the graft modification rate were measured by 1 H-NMR.
  • Acid anhydride groups are hydrolyzed A divalent group is obtained by the above-mentioned method, and the value obtained by doubling the modification rate is the total amount of the acidic group and the acid derivative type residue.
  • the weight average molecular weight (Mw) was measured in terms of polystyrene by gel permeation-chromatography using tetrahydrofuran as a solvent.
  • the content of the acryloyl group and the aryl group in the grafted product of the polymer containing a ring structure with an acryl compound and an aryl compound (primary amine) was measured by 1 H-NMR.
  • the thickness of the patterned thin film before and after heating was measured, and the thickness after heating was 95% of the thickness before heating. % Was exceeded, ⁇ was in the range of 90-95%, and X was less than 90%.
  • a glass substrate with a coating film was obtained in the same manner as described above, except that the glass substrate “Corning 7059” (manufactured by Corning) was used.
  • the transmittance of the obtained glass substrate was measured for the minimum light transmittance (t) at a wavelength of 400 to 800 nm using an ultraviolet-visible / near-infrared spectrophotometer (V-570) manufactured by JASCO Corporation. ⁇ : 97% ⁇ t, ⁇ : 95% ⁇ t ⁇ 97%, X: 95%> t
  • the glass substrate on which the patterned thin film was formed was immersed in dimethyl sulfoxide at 70 ° C for 15 minutes, and the film thickness change rate (S) was measured.
  • S film thickness change rate
  • ⁇ 10%> S
  • mm 10% ⁇ S
  • X Swelling was large and peeled off from the substrate.
  • the water absorption is measured according to JISC 6481, and the water absorption (w) is measured.
  • the minimum pattern dimension (W) is formed with a line-and-space of 1: 1 line width.
  • Tungsten hexachloride 1 to using hexene as Polymerization catalyst and molecular weight modifier consisting of triisobutylaluminum and isobutyl alcohol, by methods known 8 Echirutetorashiku port [4.4.1 0.1 2 '5.1 7.2 10 ] Ring opening polymerization of 1-3-dodecene.
  • the obtained ring-opened polymer is hydrogenated using a hydrogenation catalyst comprising nickel acetylacetonate and triisobutylaluminum to obtain a hydrogenated ring-opened polymer having a hydrogenation rate of 99% or more.
  • a hydrogenation catalyst comprising nickel acetylacetonate and triisobutylaluminum
  • a maleic anhydride-modified polymer was obtained in the same manner as in Example 1, except that the amount of maleic anhydride was changed to 150 parts and the amount of dicumyl baroxide was changed to 15 parts. Next, 30 parts of 2-hydroxyethyl acrylate, 3.5 parts of triethylamine and 0.5 part of 2,6-di-tert-butyl 4-methylphenol are added to 100 parts of the maleic anhydride-modified polymer. Then, the mixture was reacted in dried dimethylacetamide at 25 ° C. for 5 hours. Then, polymer A was obtained in the same manner as in Example 1 except that 20 parts of arylamine was added and the reaction was further performed for 1 hour. Spectroscopic analysis by FT-IR confirmed that this polymer A was rich in amide groups. Table 1 shows the physical properties.
  • pentaerythritol triacrylate PE-3A manufactured by Kyoeisha Chemical Co., Ltd.
  • paranitrobenzoyl chloride paranitrobenzoyl chloride
  • trisacryloyl pentaerythritol p-aminobenzoate TAPE
  • Polymer B was obtained in the same manner as in Example 2 except that 2-hydroxyethyl acrylate was changed to the above TAPE and the reaction temperature was changed to 80 ° C. Spectroscopic analysis by FT-IR confirmed that this polymer B was rich in amide groups. Table 1 shows the physical properties.
  • Polymer C was obtained in the same manner as in Example 2, except that 30 parts of 2-hydroxyethyl acrylate was changed to 40 parts of PE-3. Spectroscopic analysis by FT-IR confirmed that this polymer C was rich in amide groups. Table 1 shows the physical properties.
  • Example 5 shows the molecular weight of the maleic anhydride-modified polymer, and Comparative Example 1 shows the molecular weight after hydrolysis.
  • a photopolymerization initiator (Circa Specialty Co., Ltd., irgacure 907) based on 100 parts of polymer A, surfactant (MegaFac F172, manufactured by Dainippon Ink and Chemicals, Inc.) 0 0.5 part was dissolved in dimethylformamide so that the mixture amount became 20% by weight to obtain a photosensitive resin composition solution.
  • the solution was filtered through a 0.45 jtm millipore filter, spin-coated on a silicon substrate, a glass substrate, and a silicon oxide film substrate having a 1 / m step, and then heated at 90 ° C. For 2 minutes on a pot plate to form a coating film having a thickness of 3.0 ⁇ Wm.
  • a mask having a predetermined pattern is placed on the obtained silicon substrate with a coating film, and ultraviolet light having a wavelength of 365 nm and a light intensity of 5 mWZ cm 2 has an energy amount of 500 mJZ cm 2 in the air.
  • Irradiation as follows. Subsequently, development was performed at 25 ° C. for 60 seconds using an aqueous solution of tetramethylammonium having a weight of 0.3 / 0 / o. After that, a rinsing treatment with ultrapure water was performed for 1 minute. Thus, a thin film having a negative pattern was formed.
  • the silicon substrate on which this pattern was formed and the glass substrate with a coating film that had not been subjected to development processing were heated on a hot plate at 200 ° C for 30 minutes to return and coat the substrate.
  • a silicon substrate having a patterned thin film formed thereon, a coated glass substrate, and a coated silicon oxide film substrate having a step of 1 Um were obtained.
  • a substrate was obtained in the same manner as in Example 5, except that Polymer A was changed to Polymer B (Example 6), Polymer C (Example 7) or Polymer D (Example 8). Table 2 shows the evaluation results.
  • a substrate was obtained in the same manner as in Example 8, except that 20 parts of dipentaerythritol hexacrylate (DPE-6A manufactured by Kyoeisha Chemical Co., Ltd.) was added to the photosensitive resin composition.
  • DPE-6A dipentaerythritol hexacrylate manufactured by Kyoeisha Chemical Co., Ltd.
  • an acrylic resin is reacted with an epoxy resin having an alicyclic structure (XD-1000-2 L manufactured by Nippon Kayaku), An acrylic acid-modified epoxy resin was obtained.
  • the resin had an epoxy equivalent of 12232 gZeq and was confirmed by 1 H-NMR to contain an acryloyl group.
  • the epoxy resin was reacted with succinic anhydride using triphenylphosphine as a catalyst to obtain an acid-pendant acrylic acid-modified epoxy resin having an acid value of 96.8 mg KOHZg (referred to as DCP-NA).
  • a substrate was obtained in the same manner as in Example 8, except that 20 parts of an acid pendant acrylic acid-modified epoxy resin was added to the photosensitive resin composition.
  • Table 2 shows the evaluation results.
  • the photosensitive resin composition contains 20 parts of an acid pendant acrylic acid-modified epoxy resin and a crosslinking agent (N, N, N ', N', N ", N"-(hexamethoxymethyl) melamine (C manufactured by Mitsui Cytec Co., Ltd.)
  • a crosslinking agent N, N, N ', N', N ", N"-(hexamethoxymethyl) melamine (C manufactured by Mitsui Cytec Co., Ltd.)
  • a substrate was obtained in the same manner as in Example 8, except that 20 parts of YME L300) were added.
  • Examples 5 to 11 have low dielectric properties, low water absorption, heat-resistant dimensional stability, flatness, heat discoloration resistance, transparency, solvent resistance, and resolution. It turns out that it is also excellent.
  • a polymer having a radical polymerizable group and a lipoxyl group a polymer having a modification rate by an acid anhydride of 70 mol% or more and an acryloyl group content of 4 OmoI% or more is used. (Comparison between Example 5 and Example 8) It can be seen that the resolution is excellent.
  • the photosensitive composition of the present invention is coated on a silicon substrate or the like, dried, exposed to a pattern, and then imaged to provide various properties such as flatness, heat resistance, transparency, and chemical resistance, and to provide low performance.
  • a fine patterned thin film having excellent dielectric properties can be easily formed.
  • the thin film obtained by using the photosensitive composition of the present invention can be used as an insulating material, for example, for an electronic element such as a semiconductor element, a light emitting diode, and various memories; It is preferably used for an interlayer insulating film of a multilayer circuit board; an insulating layer of a liquid crystal display.

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  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
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Abstract

L'invention concerne une composition de résine photosensible qui ne possède pas seulement d'excellentes performances, telles que l'uniformité, la résistance à la chaleur, la transparence et la résistance chimique, mais qui est aussi capable de former un film mince à motif fin doté d'excellentes caractéristiques à faible pouvoir diélectrique. La composition de résine photosensible comprend un polymère obtenu par la réaction d'un polymère oléfine alicyclique avec un composé doté d'un groupe acide ou d'un groupe dérivé acide afin d'obtenir un polymère oléfine alicyclique contenant des groupes acides ou des groupes dérivés acides, puis par la réaction du polymère obtenu avec un composé ayant un groupe non saturé polymérisable afin d'obtenir un polymère oléfine alicyclique contenant des groupes non saturés polymérisables et des groupes acides ou des groupes dérivés acides. La composition comprend en outre un initiateur de photopolymérisation et éventuellement un réactif d'agent de durcissement associé à un groupe hydroxyle ou au groupe acide, au groupe dérivé acide ou à un agent de réticulation ayant un groupe non saturé polymérisable.
PCT/JP2001/003296 2000-04-18 2001-04-18 Composition de resine photosensible WO2001079325A1 (fr)

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JP2002363263A (ja) * 2001-06-08 2002-12-18 Nippon Zeon Co Ltd 開環共重合体、開環共重合体水素化物、それらの製造方法および組成物
WO2004067601A1 (fr) * 2003-01-31 2004-08-12 Zeon Corporation Composition polymerisable, composition de resine thermoplastique, resine reticulee, et materiaux composites a base de resine reticulee
US6815467B2 (en) 2001-07-18 2004-11-09 Asahi Glass Company, Limited Methods for producing a polyol and a polymer dispersed polyol
WO2005096100A1 (fr) * 2004-03-31 2005-10-13 Zeon Corporation Composition sensible à un rayonnement, stratifié, processus de fabrication de celui-ci et composant électronique
JP2005352472A (ja) * 2004-05-14 2005-12-22 Mitsubishi Chemicals Corp 液晶パネル用樹脂組成物、硬化物、液晶パネル、及び液晶表示装置
JPWO2004029153A1 (ja) * 2002-09-27 2006-01-26 日本ゼオン株式会社 熱硬化性磁性スラリー及びその利用
JP2009167433A (ja) * 2009-05-07 2009-07-30 Nippon Zeon Co Ltd 開環共重合体、開環共重合体水素化物、それらの製造方法および組成物
JP2009538455A (ja) * 2006-05-26 2009-11-05 ドンウー ファイン−ケム カンパニー リミテッド 着色ネガティブフォトレジスト組成物、それを含む着色パターンおよびその製造方法
JP2009287041A (ja) * 1999-12-07 2009-12-10 Nippon Zeon Co Ltd 開環共重合体水素化物
JP2012057122A (ja) * 2010-09-13 2012-03-22 Nippon Zeon Co Ltd ノルボルネン系開環共重合体水素化物からなるフィルム
JP2014520935A (ja) * 2011-07-14 2014-08-25 住友ベークライト株式会社 自己現像層形成ポリマーおよびその組成物
JP2015025892A (ja) * 2013-07-25 2015-02-05 日本ゼオン株式会社 ネガ型感光性樹脂組成物および電子部品
WO2018179259A1 (fr) * 2017-03-30 2018-10-04 日立化成株式会社 Composition de résine photosensible, film sec utilisant celle-ci, carte de circuit imprimé et procédé de fabrication de carte de circuit imprimé
WO2018179260A1 (fr) * 2017-03-30 2018-10-04 日立化成株式会社 Composition de résine photosensible, film durci à motif ainsi que procédé de fabrication de celui-ci, élément photosensible, et carte de circuit imprimé ainsi que procédé de fabrication de celle-ci

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JPH1030018A (ja) * 1996-03-20 1998-02-03 Ivoclar Ag 重合性機能化ポリマー

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JPH1030018A (ja) * 1996-03-20 1998-02-03 Ivoclar Ag 重合性機能化ポリマー

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JP4556373B2 (ja) * 1999-12-07 2010-10-06 日本ゼオン株式会社 開環共重合体水素化物の製造方法
JP2012111968A (ja) * 1999-12-07 2012-06-14 Nippon Zeon Co Ltd 開環共重合体水素化物
JP2009287041A (ja) * 1999-12-07 2009-12-10 Nippon Zeon Co Ltd 開環共重合体水素化物
JP2002363263A (ja) * 2001-06-08 2002-12-18 Nippon Zeon Co Ltd 開環共重合体、開環共重合体水素化物、それらの製造方法および組成物
US6815467B2 (en) 2001-07-18 2004-11-09 Asahi Glass Company, Limited Methods for producing a polyol and a polymer dispersed polyol
JPWO2004029153A1 (ja) * 2002-09-27 2006-01-26 日本ゼオン株式会社 熱硬化性磁性スラリー及びその利用
WO2004067601A1 (fr) * 2003-01-31 2004-08-12 Zeon Corporation Composition polymerisable, composition de resine thermoplastique, resine reticulee, et materiaux composites a base de resine reticulee
EP1589054A1 (fr) * 2003-01-31 2005-10-26 Zeon Corporation Composition polymerisable, composition de resine thermoplastique, resine reticulee, et materiaux composites a base de resine reticulee
CN100365039C (zh) * 2003-01-31 2008-01-30 日本瑞翁株式会社 可聚合组合物、热塑性树脂组合物、交联树脂以及交联树脂复合材料
EP1589054A4 (fr) * 2003-01-31 2009-04-29 Zeon Corp Composition polymerisable, composition de resine thermoplastique, resine reticulee, et materiaux composites a base de resine reticulee
WO2005096100A1 (fr) * 2004-03-31 2005-10-13 Zeon Corporation Composition sensible à un rayonnement, stratifié, processus de fabrication de celui-ci et composant électronique
JP2005352472A (ja) * 2004-05-14 2005-12-22 Mitsubishi Chemicals Corp 液晶パネル用樹脂組成物、硬化物、液晶パネル、及び液晶表示装置
JP2009538455A (ja) * 2006-05-26 2009-11-05 ドンウー ファイン−ケム カンパニー リミテッド 着色ネガティブフォトレジスト組成物、それを含む着色パターンおよびその製造方法
JP2009167433A (ja) * 2009-05-07 2009-07-30 Nippon Zeon Co Ltd 開環共重合体、開環共重合体水素化物、それらの製造方法および組成物
JP2012057122A (ja) * 2010-09-13 2012-03-22 Nippon Zeon Co Ltd ノルボルネン系開環共重合体水素化物からなるフィルム
JP2014520935A (ja) * 2011-07-14 2014-08-25 住友ベークライト株式会社 自己現像層形成ポリマーおよびその組成物
JP2015025892A (ja) * 2013-07-25 2015-02-05 日本ゼオン株式会社 ネガ型感光性樹脂組成物および電子部品
WO2018179259A1 (fr) * 2017-03-30 2018-10-04 日立化成株式会社 Composition de résine photosensible, film sec utilisant celle-ci, carte de circuit imprimé et procédé de fabrication de carte de circuit imprimé
WO2018179260A1 (fr) * 2017-03-30 2018-10-04 日立化成株式会社 Composition de résine photosensible, film durci à motif ainsi que procédé de fabrication de celui-ci, élément photosensible, et carte de circuit imprimé ainsi que procédé de fabrication de celle-ci
CN110521290A (zh) * 2017-03-30 2019-11-29 日立化成株式会社 感光性树脂组合物、使用了其的干式膜、印刷布线板及印刷布线板的制造方法
US11921424B2 (en) 2017-03-30 2024-03-05 Hitachi Chemical Company, Ltd. (FIPAS) Photosensitive resin composition, dry film using same, printed wiring board, and printed wiring board manufacturing method
US12189290B2 (en) 2017-03-30 2025-01-07 Resonac Corporation Photosensitive resin composition, dry film using same, printed wiring board, and printed wiring board manufacturing method

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