WO2011089895A1 - Composition polymère sensible à la lumière, procédé de fabrication d'un motif et composant électronique - Google Patents

Composition polymère sensible à la lumière, procédé de fabrication d'un motif et composant électronique Download PDF

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WO2011089895A1
WO2011089895A1 PCT/JP2011/000251 JP2011000251W WO2011089895A1 WO 2011089895 A1 WO2011089895 A1 WO 2011089895A1 JP 2011000251 W JP2011000251 W JP 2011000251W WO 2011089895 A1 WO2011089895 A1 WO 2011089895A1
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component
polymer composition
photosensitive polymer
weight
group
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PCT/JP2011/000251
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English (en)
Japanese (ja)
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小野敬司
峯岸知典
大江匡之
小谷真志
紺野琢
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日立化成デュポンマイクロシステムズ株式会社
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Priority to KR1020127018651A priority Critical patent/KR101488070B1/ko
Priority to CN201180006656.9A priority patent/CN102725694B/zh
Priority to JP2011550852A priority patent/JP5365704B2/ja
Publication of WO2011089895A1 publication Critical patent/WO2011089895A1/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
    • C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
    • C08L77/06—Polyamides derived from polyamines and polycarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0091—Complexes with metal-heteroatom-bonds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/13—Phenols; Phenolates
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/21—Urea; Derivatives thereof, e.g. biuret
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/022—Quinonediazides
    • G03F7/023—Macromolecular quinonediazides; Macromolecular additives, e.g. binders
    • G03F7/0233—Macromolecular quinonediazides; Macromolecular additives, e.g. binders characterised by the polymeric binders or the macromolecular additives other than the macromolecular quinonediazides
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/085—Photosensitive compositions characterised by adhesion-promoting non-macromolecular additives
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/20—Exposure; Apparatus therefor
    • G03F7/2002—Exposure; Apparatus therefor with visible light or UV light, through an original having an opaque pattern on a transparent support, e.g. film printing, projection printing; by reflection of visible or UV light from an original such as a printed image
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/26—Processing photosensitive materials; Apparatus therefor
    • G03F7/40—Treatment after imagewise removal, e.g. baking
    • 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
    • H01L21/02118—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 carbon based polymeric organic or inorganic material, e.g. polyimides, poly cyclobutene or PVC
    • 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
    • H01L21/027—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34
    • H01L21/0271—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising organic layers

Definitions

  • the present invention relates to a photosensitive polymer composition, a pattern production method, and an electronic component. More specifically, a positive-type photosensitive polymer composition that can improve adhesion with a substrate while maintaining a pattern with excellent resolution and good shape without lowering sensitivity, and the polymer composition.
  • the present invention relates to a method for producing a patterned cured film and an electronic component.
  • a polyimide resin film having excellent heat resistance, electrical characteristics, mechanical characteristics, and the like has been used for a surface protective film and an interlayer insulating film of a semiconductor element.
  • This polyimide resin film is generally applied by spin coating or the like with a polyimide precursor (polyamic acid) solution (so-called varnish) obtained by reacting tetracarboxylic dianhydride and diamine in a polar solvent at normal temperature and pressure. Then, the film is formed into a thin film and formed by dehydration ring closure (curing) by heating (for example, see Non-Patent Document 1).
  • an organic solvent such as N-methylpyrrolidone has been used for developing the photosensitive polyimide, but recently, a positive photosensitive resin that can be developed with an alkaline aqueous solution has been proposed from the viewpoint of environment and cost. ing.
  • a method for obtaining such an alkali-developable positive photosensitive resin a method of introducing an o-nitrobenzyl group into a polyimide precursor via an ester bond (for example, see Non-Patent Document 2), soluble hydroxylimide or There is a method of mixing a naphthoquinone diazide compound with a polybenzoxazole precursor (for example, see Patent Documents 4 and 5).
  • a resin obtained by such a method can be expected to have a low dielectric constant, and photosensitive polybenzoxazole is attracting attention together with photosensitive polyimide from such a viewpoint.
  • photosensitive resins have been applied to various wiring layers in accordance with changes in the structure of devices. Here, for example, adhesion to aluminum wiring, electroless plating solution, etc. Resistance to plating solution is being demanded.
  • Patent Documents 6 to 9 describe that an aluminum complex is used together with an active silicon compound to promote cyclization of a polymer, and a compound having an oxetane group as a crosslinking agent is used to improve reflow resistance, solvent resistance, and the like. It has been shown to improve.
  • an object of the present invention is to provide a photosensitive polymer composition capable of forming a pattern excellent in plating solution resistance. Furthermore, according to the present invention, there is provided a photosensitive polymer composition which is excellent in the dissolution rate ratio (hereinafter referred to as contrast) between the unexposed area and the exposed area, and has good sensitivity, resolution, adhesion and storage stability. can do.
  • the present inventors have found that the adhesion of the substrate can be improved by using an alkali developable polymer together with an aluminum complex compound and a specific crosslinking agent as an adhesion aid.
  • a photosensitive polymer composition comprising the following components (a) to (d): (A) a polymer soluble in an alkaline aqueous solution (b) a compound capable of generating an acid by light (c) an aluminum complex (d) a group represented by —CH 2 OR (R is a hydrogen atom or a monovalent organic group) 1. a cross-linking agent having (D) The photosensitive polymer composition of 1 whose crosslinking agent is a compound represented by the following formula (1) or a compound represented by the following formula (2).
  • a plurality of R 7 are each independently a hydrogen atom or a monovalent organic group
  • a plurality of R 8 are each independently a hydrogen atom or a monovalent organic group, and are bonded to each other to have a substituent.
  • a ring structure may be formed.
  • X is a single bond or a monovalent to tetravalent organic group
  • R 11 is a hydrogen atom or a monovalent organic group
  • R 12 is a monovalent organic group
  • o is 1 to 4
  • A is an integer of 1 to 4
  • b is an integer of 0 to 3.
  • R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are each independently a hydrogen atom or a monovalent organic group.) 7).
  • a method for producing a pattern comprising a step of applying the photosensitive polymer composition according to any one of 10.1 to 9 on a support substrate and drying, a step of exposing, a step of developing, and a step of heat treatment. 11.
  • the method for producing a pattern according to 10 wherein the light source used in the exposing step is i-line.
  • An electronic component comprising the cured product according to 13.12 as a surface protective film or an interlayer insulating film.
  • a photosensitive polymer composition capable of forming a pattern having excellent plating solution resistance. Furthermore, according to the present invention, it is possible to provide a photosensitive polymer composition that is excellent in the dissolution rate ratio (contrast) between an unexposed part and an exposed part, and has good sensitivity, resolution, adhesion, and storage stability. it can.
  • the photosensitive polymer composition according to the present invention comprises (a) a polymer that is soluble in an alkaline aqueous solution, (b) a compound that generates an acid by light, (c) an aluminum complex, and (d) —CH 2 OR (R is hydrogen).
  • the photosensitive polymer composition of the present invention is excellent in sensitivity and resolution by increasing the dissolution rate ratio (dissolution contrast) of the pattern exposed area and the unexposed area to the developer.
  • the polymer soluble in the alkaline aqueous solution as component (a) is preferably a polyimide-based polymer or a polyoxazole-based polymer, and specifically preferred are: It is at least one polymer compound selected from polyimide, polyamideimide, polyoxazole, polyamide, and precursors thereof (for example, polyamic acid, polyamic acid ester, polyhydroxyamide, etc.).
  • the component (a) may be a copolymer having two or more main chain skeletons described above, or a mixture of two or more of the above polymers.
  • the polymer soluble in alkaline aqueous solution is preferably a polymer having a plurality of phenolic hydroxyl groups, a plurality of carboxy groups, or both groups.
  • the component (a) is more preferably an alkaline aqueous solution-soluble polyamide having a structural unit represented by the following formula (I) that functions as a precursor of polybenzoxazole and has good photosensitivity and film properties.
  • formula (I) that functions as a precursor of polybenzoxazole and has good photosensitivity and film properties.
  • U is a tetravalent organic group
  • V is a divalent organic group.
  • the polyamide containing a hydroxy group represented by the formula (I) is finally converted into an oxazole having excellent heat resistance, mechanical properties and electrical properties by dehydration and ring closure at the time of curing.
  • the alkaline aqueous solution is an alkaline solution such as a tetramethylammonium hydroxide aqueous solution, a metal hydroxide aqueous solution, or an organic amine aqueous solution.
  • the tetravalent organic group of U in formula (I) is generally a residue derived from dihydroxydiamine that reacts with a dicarboxylic acid to form a polyamide structure, preferably a tetravalent aromatic group, and its carbon atom.
  • the number is preferably 6 to 40, more preferably a tetravalent aromatic group having 6 to 40 carbon atoms.
  • Such diamines include 3,3′-diamino-4,4′-dihydroxybiphenyl, 4,4′-diamino-3,3′-dihydroxybiphenyl, bis (3-amino-4-hydroxyphenyl) propane.
  • Bis (4-amino-3-hydroxyphenyl) propane, bis (3-amino-4-hydroxyphenyl) sulfone, bis (4-amino-3-hydroxyphenyl) sulfone, 2,2-bis (3-amino- 4-hydroxyphenyl) -1,1,1,3,3,3-hexafluoropropane, 2,2-bis (4-amino-3-hydroxyphenyl) -1,1,1,3,3,3- Examples include hexafluoropropane.
  • the residue of diamine is not limited to these, You may combine the residue of these compounds individually or in combination of 2 or more types.
  • the divalent organic group of V in formula (I) is generally a residue derived from a dicarboxylic acid that reacts with a diamine to form a polyamide structure, preferably a divalent aromatic group, and has a carbon atom number.
  • the divalent aromatic group those in which two bonding sites are both present on the aromatic ring are preferred.
  • dicarboxylic acids include isophthalic acid, terephthalic acid, 2,2-bis (4-carboxyphenyl) -1,1,1,3,3,3-hexafluoropropane, 4,4′-dicarboxybiphenyl 4,4′-dicarboxydiphenyl ether, 4,4′-dicarboxytetraphenylsilane, bis (4-carboxyphenyl) sulfone, 2,2-bis (p-carboxyphenyl) propane, 5-tert-butylisophthalic acid
  • Aromatic dicarboxylic acids such as 5-bromoisophthalic acid, 5-fluoroisophthalic acid, 5-chloroisophthalic acid, 2,6-naphthalenedicarboxylic acid, 1,2-cyclobutanedicarboxylic acid, 1,4-cyclohexanedicarboxylic acid, Aliphatic dicarboxylic acids such as 1,3-cyclopentanedicarboxylic acid, oxa
  • the alkaline aqueous solution-soluble polyamide having the structural unit represented by the formula (I) may have a structure other than the structural unit represented by the formula (I).
  • an amide unit containing a hydroxy group is contained in a certain proportion or more.
  • the alkaline aqueous solution-soluble polyamide having the structural unit represented by the formula (I) is preferably a polyamide represented by the following formula.
  • the two structural units may be arranged at random or in a block shape.
  • U is a tetravalent organic group
  • V and W are divalent organic groups.
  • j and k represent mole fractions, and the sum of j and k is 100 mol%, j is 60 to 100 mol%, and k is 0 to 40 mol%.
  • the divalent organic group represented by W is generally a residue of a diamine that reacts with a dicarboxylic acid to form a polyamide structure, and is a residue other than the diamine that forms the U, preferably a divalent group.
  • a divalent aromatic group having 4 to 40 carbon atoms more preferably a divalent aromatic group having 4 to 40 carbon atoms.
  • Such diamines include 4,4′-diaminodiphenyl ether, 4,4′- Diaminodiphenylmethane, 4,4′-diaminodiphenylsulfone, 4,4′-diaminodiphenyl sulfide, benzidine, m-phenylenediamine, p-phenylenediamine, 1,5-naphthalenediamine, 2,6-naphthalenediamine, bis (4 -Aminophenoxyphenyl) sulfone, bis (3-aminophenoxyphenyl) sulfone, bis (4-aminophenoxy) biphenyl, bis [4- (4-aminophenoxy) phenyl] ether, 1,4-bis (4-aminophenoxy) ) Aromatic diamine compounds such as benzene; LP-7100, X-22-161AS, X-22-161A, X-22-161B, X-22-161C and X-22-161E which are
  • the terminal group of the aromatic polyamide represented by the formula (I) becomes an amine having a carboxylic acid or a phenol group depending on the charging ratio of U and V. If necessary, the polymer end alone or two kinds of end cap agents are reacted, and one end or both ends are saturated aliphatic group, unsaturated aliphatic group, carboxy group, phenol hydroxyl group, sulfonic acid group, or thiol, respectively. It may be a group. At that time, the end cap ratio is preferably 30 to 100%.
  • the molecular weight of the component (a) is preferably 3,000 to 200,000, more preferably 5,000 to 100,000 in terms of weight average molecular weight.
  • the molecular weight is a value obtained by measuring by a gel permeation chromatography method and converting from a standard polystyrene calibration curve.
  • the polyamide having the structural unit represented by the formula (I) can be generally synthesized from a dicarboxylic acid derivative and a hydroxy group-containing diamine. Specifically, it can be synthesized by converting a dicarboxylic acid derivative into a dihalide derivative and then reacting with the diamine. As the dihalide derivative, a dichloride derivative is preferable.
  • the dichloride derivative can be synthesized by reacting a dicarboxylic acid derivative with a halogenating agent.
  • a halogenating agent thionyl chloride, phosphoryl chloride, phosphorus oxychloride, phosphorus pentachloride, etc., which are used in the usual acid chloride reaction of carboxylic acid can be used.
  • the dichloride derivative As a method of synthesizing the dichloride derivative, it can be synthesized by reacting the dicarboxylic acid derivative and the halogenating agent in a solvent or by reacting in an excess halogenating agent and then distilling off the excess.
  • the reaction solvent N-methyl-2-pyrrolidone, N-methyl-2-pyridone, N, N-dimethylacetamide, N, N-dimethylformamide, toluene, benzene and the like can be used.
  • the amount of these halogenating agents to be used in a solvent is preferably 1.5 to 3.0 mol, more preferably 1.7 to 2.5 mol relative to the dicarboxylic acid derivative. In the case of reacting in an agent, 4.0 to 50 mol is preferable, and 5.0 to 20 mol is more preferable.
  • the reaction temperature is preferably ⁇ 10 to 70 ° C., more preferably 0 to 20 ° C.
  • the reaction between the dichloride derivative and the diamine is preferably performed in an organic solvent in the presence of a dehydrohalogenating agent.
  • a dehydrohalogenating agent organic bases such as pyridine and triethylamine are usually used.
  • organic solvent N-methyl-2-pyrrolidone, N-methyl-2-pyridone, N, N-dimethylacetamide, N, N-dimethylformamide and the like can be used.
  • the reaction temperature is preferably ⁇ 10 to 30 ° C., more preferably 0 to 20 ° C.
  • the compound (b) that generates an acid by light is a photosensitive agent, and is a compound that has a function of generating an acid by light and increasing the solubility of the light irradiated portion in an alkaline aqueous solution.
  • the component (b) include o-quinonediazide compounds, aryldiazonium salts, diaryliodonium salts, and triarylsulfonium salts.
  • the o-quinonediazide compounds are preferable because of their high sensitivity.
  • the o-quinonediazide compound can be obtained, for example, by subjecting o-quinonediazidesulfonyl chlorides to a hydroxy compound, an amino compound or the like in the presence of a dehydrochlorinating agent.
  • o-quinonediazide sulfonyl chlorides include benzoquinone-1,2-diazide-4-sulfonyl chloride, 1,2-naphthoquinone-2-diazide-5-sulfonyl chloride, and 1,2-naphthoquinone-2-diazide-4.
  • -Sulfonyl chloride and the like can be used.
  • hydroxy compound examples include hydroquinone, resorcinol, pyrogallol, bisphenol A, bis (4-hydroxyphenyl) methane, 2,2-bis (4-hydroxyphenyl) hexafluoropropane, and 2,3,4-trihydroxybenzophenone.
  • amino compounds include p-phenylenediamine, m-phenylenediamine, 4,4′-diaminodiphenyl ether, 4,4′-diaminodiphenylmethane, 4,4′-diaminodiphenylsulfone, and 4,4′-diaminodiphenyl sulfide.
  • the compounding ratio of o-quinonediazide sulfonyl chloride and hydroxy compound and / or amino compound is such that the total of hydroxy group and amino group is 0.5 to 1 equivalent per mole of o-quinonediazide sulfonyl chloride. It is preferable.
  • a preferred ratio of the dehydrochlorinating agent and o-quinonediazide sulfonyl chloride is in the range of 0.95 / 1 to 1 / 0.95.
  • a preferred reaction temperature is 0 to 40 ° C., and a preferred reaction time is 1 to 10 hours.
  • reaction solvent solvents such as dioxane, acetone, methyl ethyl ketone, tetrahydrofuran, diethyl ether, N-methylpyrrolidone and the like are used.
  • dehydrochlorination agent include sodium carbonate, sodium hydroxide, sodium hydrogen carbonate, potassium carbonate, potassium hydroxide, trimethylamine, triethylamine, pyridine and the like.
  • the content of the component (b) is 5 to 100 with respect to 100 parts by weight of the component (a) from the viewpoint of the difference in dissolution rate between the exposed part and the unexposed part and the sensitivity.
  • Parts by weight are preferred, 8 to 40 parts by weight are more preferred, and 8 to 20 parts by weight are even more preferred.
  • the aluminum complex as the component (c) is preferably an aluminum chelate complex from the viewpoint of adhesion to the substrate.
  • the adhesiveness of the composition can be improved by the interaction between the metal surface of the substrate and the aluminum chelate complex.
  • the aluminum complex adhesion assistant can greatly improve the adhesion of the composition compared to a silane coupling agent or the like due to the interaction between the polyamide and the aluminum chelate complex.
  • the aluminum complex has an inhibitory effect on dissolution in an alkaline aqueous solution, and is combined with a crosslinking agent having a group represented by (d) -CH 2 OR (R is a hydrogen atom or a monovalent organic group) described later. It is considered that the dissolution rate ratio (contrast) between the exposed part and the unexposed part is improved and the sensitivity is improved.
  • the aluminum complex as the component (c) is preferably an aluminum chelate complex, and more preferably an aluminum chelate complex represented by the following formula (II). (Wherein R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are each independently a hydrogen atom or a monovalent organic group.
  • the monovalent organic group includes an ether bond, an ester bond, etc. May be included)
  • Examples of the monovalent organic group for R 1 , R 2 , R 3 , R 4 , R 5 and R 6 include an alkyl group having 1 to 20 carbon atoms and an alkoxyl group having 1 to 20 carbon atoms. More preferred are an alkyl group having 1 to 6 carbon atoms and an alkoxyl group having 1 to 6 carbon atoms.
  • the three ligands may be the same or different.
  • Examples of the aluminum complex as component (c) include aluminum ethyl acetoacetate diisopropylate, aluminum tris (ethyl acetoacetate), aluminum tris (acetylacetonate), alkyl acetoacetate aluminum diisopropylate, aluminum bisethyl acetoacetate mono Examples include acetylacetonate, and aluminum tris (acetylacetonate) and aluminum bisethylacetoacetate monoacetylacetonate are preferable. These may be used alone or in combination of two or more.
  • the content of the component (c) is 0.1 to 100 parts by weight with respect to 100 parts by weight of the component (a) from the viewpoint of the difference in dissolution rate between the exposed part and the unexposed part and the sensitivity. 50 parts by weight is preferred, 0.1 to 20 parts by weight is more preferred, and 0.5 to 10 parts by weight is even more preferred.
  • the content of the component (c) is 0.1 parts by weight or more, the effect of improving the adhesion to the substrate is effective, and by setting it to 50 parts by weight or less, problems such as precipitation during frozen storage are reduced. can do.
  • the crosslinking agent having a group represented by —CH 2 OR (R is a hydrogen atom or a monovalent organic group) as component (d) is applied after the photosensitive polymer composition of the present invention is applied, exposed and developed. In the heat treatment step, it is a compound that reacts with the polymer as component (a) to crosslink, or polymerizes itself in the heat treatment step. In addition, the component (c) has an effect of promoting the crosslinking of the component (d). By including both the component (c) and the component (d), the electroless Ni / Au on the aluminum substrate as a synergistic effect. Resistance to chemicals used in the zincate process in plating can be improved.
  • the crosslinking agent which is (d) component has affinity with alkaline aqueous solution, and can improve the melt
  • the component (d) is a crosslinking agent having a group represented by —CH 2 OR (R is a hydrogen atom or a monovalent organic group) in the structure.
  • R is a hydrogen atom or a monovalent organic group
  • One or more groups may be present in the compound, but two or more groups are preferable.
  • (d) a crosslinking agent is selected from the compound represented by following formula (1) and the compound represented by following formula (2), and the following general formula ( The compound represented by 1) is more preferable because it is particularly excellent in the plating solution resistance and the high contrast effect of the present invention.
  • R 7 are each independently a hydrogen atom or a monovalent organic group
  • a plurality of R 8 are each independently a hydrogen atom or a monovalent organic group, which are bonded to each other to form a substituent.
  • a ring structure which may have (In the formula, X is a single bond or a monovalent to tetravalent organic group, R 11 is a hydrogen atom or a monovalent organic group, R 12 is a monovalent organic group, and o is 1 to 4)
  • A is an integer of 1 to 4
  • b is an integer of 0 to 3.
  • R 11 and R 12 are preferably a hydrocarbon group Preferably, it has 1 to 10 carbon atoms.
  • the hydrocarbon group is preferably an alkyl group or an alkenyl group.
  • the monovalent organic group represented by R 7 is preferably an alkyl group having 1 to 20 carbon atoms, and more preferably 1 to 6 carbon atoms.
  • the ring structure in which two R 8 are bonded to each other may contain an oxygen atom or a nitrogen atom.
  • (d) component can use these compounds individually or in combination of 2 or more types.
  • Z is an alkyl group having 1 to 10 carbon atoms.
  • R is an alkyl group having 1 to 20 carbon atoms, and more preferably an alkyl group having 1 to 6 carbon atoms.
  • the monovalent to tetravalent organic group represented by X is an alkyl group having 1 to 10 carbon atoms, an alkylidene group having 2 to 10 carbon atoms such as an ethylidene group, or a carbon atom having 6 to 6 carbon atoms such as a phenylene group.
  • arylene groups groups in which some or all of hydrogen atoms of these hydrocarbon groups are substituted with halogen atoms such as fluorine atoms, and these groups are further phenyl groups, sulfone groups, carbonyl groups, ether bonds, thioethers A bond, an amide bond, and the like may be included.
  • R 11 is preferably hydrogen, an alkyl group or an alkenyl group.
  • the alkyl group or alkenyl group preferably has 1 to 20 carbon atoms.
  • R 12 is preferably an alkyl group, an alkenyl group, an alkoxyalkyl group or a methylol group.
  • the carbon number is preferably 1-20. o is an integer of 1 to 4, a is an integer of 1 to 4, and b is an integer of 0 to 4. )
  • the compound represented by the formula (2) is preferably a compound represented by the following formula (V).
  • X is a single bond or a divalent organic group.
  • the divalent organic group include an alkylene group having 1 to 10 carbon atoms such as a methylene group, an ethylene group and a propylene group, an ethylidene group, -Cylalkylene groups having 2 to 10 carbon atoms such as propylidene groups, arylene groups having 6 to 30 carbon atoms such as phenylene groups, and groups in which some or all of the hydrogen atoms of these hydrocarbon groups are substituted with halogen atoms such as fluorine atoms
  • These groups may further contain a sulfone group, a carbonyl group, an ether bond, a thioether bond, an amide bond and the like.
  • Each R is independently a hydrogen atom, an alkyl group or an alkenyl group.
  • the carbon number is preferably 1-20.
  • R 14 and R 15 are each independently an alkyl group, an alkenyl group, a methylol group, or an alkoxyalkyl group, and these groups may partially have an ether bond, an ester bond, or the like.
  • the carbon number is preferably 1-20.
  • e and f are each independently an integer of 1 or 2
  • g and h are each independently an integer of 0 to 3.
  • X in the compounds represented by formula (2) and formula (V) is preferably a linking group represented by formula (VI).
  • each A is independently a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a group partially containing an oxygen atom or a fluorine atom.
  • At least one of A is preferably a group partially containing a fluorine atom or an aryl group having 6 to 20 carbon atoms.
  • the group containing an oxygen atom or a fluorine atom in part includes an alkyloxy group, and the group containing a fluorine atom includes a perfluoroalkyl group.
  • the number of carbon atoms is preferably 1-20.
  • Examples of the compound represented by (2) include 2,2′-methylenebis (4-methyl-6-methoxymethylphenol), 4,4′-methylenebis (2-methyl-6-hydroxymethylphenol), 4 , 4′-methylenebis [2,6-bis (methoxymethyl) phenol], 4,4 ′-(1,1,1,3,3,3-hexafluoroisopropylidene) bis [2,6-bis (methoxy) Methyl) phenol], bis (2-hydroxy-3-methoxymethyl-5-methylphenyl) methane, 4,4 ′-(1-phenylethylidene) bis [2,6-bis (methoxymethyl) phenol], bis ( 2-hydroxy-3-ethoxymethyl-5-methylphenyl) methane, bis (2-hydroxy-3-propoxymethyl-5-methylphenyl) methane, bis (2-hydride) Xy-3-butoxymethyl-5-methylphenyl) methane, bis [2-hydroxy-3- (1-propenyloxy) methyl-5-methylphenyl] methan
  • 4,4 ′-(1,1,1,3,3,3-hexafluoroisopropylidene) bis [2,6- Bis (hydroxymethyl) phenol] is most preferable from the viewpoint of the effect of improving sensitivity and the solubility of the film during development.
  • the content of the component (d) is preferably 1 to 30 parts by weight with respect to 100 parts by weight of the component (a) from the viewpoint of sensitivity, resolution and storage stability during exposure. More preferred is 5 to 25 parts by mass.
  • the photosensitive polymer composition of the present invention may further contain (e) an alkoxysilane adhesive.
  • the alkoxysilane compound of the alkoxysilane adhesive includes, for example, bis (2-hydroxyethyl) -3-aminopropyltriethoxysilane, ⁇ -glycidoxypropyltriethoxysilane, and ⁇ -methacryloxypropyltrimethoxysilane.
  • the content when the component (e) is contained, the content is preferably 0.1 to 20 parts by weight, more preferably 1 to 100 parts by weight of the component (a). ⁇ 10 parts by weight.
  • the content of the component (e) By setting the content of the component (e) to 0.1 parts by weight or more, good adhesion to the substrate can be imparted to the composition, and by setting it to 20 parts by weight or less, good storage stability is obtained.
  • the photosensitive polymer composition of the present invention preferably contains a compound selected from the group consisting of an onium salt, a diaryl compound and a tetraalkylammonium salt as the component (f).
  • component (f) inhibits dissolution of component (a) in an alkaline aqueous solution.
  • Examples of the onium salt include iodonium salts such as diaryl iodonium salts, sulfonium salts such as triarylsulfonium salts, diazonium salts such as phosphonium salts and aryldiazonium salts.
  • Examples of the diaryl compound include compounds in which two aryl groups such as diaryl urea, diaryl sulfone, diaryl ketone, diaryl ether, diaryl propane, and diaryl hexafluoropropane are bonded via a bonding group. Groups are preferred.
  • Examples of the tetraalkylammonium salt include tetraalkylammonium halides in which the alkyl group is a methyl group, an ethyl group, or the like.
  • Examples of the component (f) exhibiting a good dissolution inhibiting effect include diaryliodonium salts, diarylurea compounds, diarylsulfone compounds, tetramethylammonium halide compounds, and the like.
  • Examples of the diarylurea compound include diphenylurea and dimethyldiphenylurea, and examples of the tetramethylammonium halide compound include tetramethylammonium chloride, tetramethylammonium bromide, and tetramethylammonium iodide.
  • the component (f) is preferably a diaryliodonium salt represented by the following formula (VIII).
  • X ⁇ represents a counter anion.
  • R 8 and R 9 are each independently an alkyl group or an alkenyl group.
  • m and n are each independently an integer of 0 to 5.
  • X ⁇ in the formula (VIII) is nitrate ion, boron tetrafluoride ion, perchlorate ion, trifluoromethanesulfonate ion, p-toluenesulfonate ion, thiocyanate ion, chlorine ion, bromine ion, iodine ion, etc. Can be mentioned.
  • diaryliodonium salt represented by the formula (VIII) examples include diphenyliodonium nitrate, bis (p-tert-butylphenyl) iodonium nitrate, diphenyliodonium trifluoromethanesulfonate, and bis (p-tert-butylphenyl). Examples thereof include iodonium trifluoromethanesulfonate, diphenyliodonium bromide, diphenyliodonium chloride, and diphenyliodonium iodide.
  • diphenyliodonium nitrate diphenyliodonium trifluoromethanesulfonate
  • diphenyliodonium-8-anilinonanaphthalene-1-sulfonate are preferred because of their high effects.
  • the content is preferably 0.01 to 15 parts by weight, more preferably 0.01 to 10 parts by weight with respect to 100 parts by weight of the component (a) from the viewpoint of sensitivity and development time. 0.05 to 3 parts by weight is more preferable.
  • the composition of the present invention may contain the components (a) to (d) and the optional component (e), and the total of these is, for example, 90% by weight or more, 95% by weight or more, 99% by weight or more, or It may be 100% by weight.
  • the photosensitive polymer composition of the present invention can further contain the following solvents, additives and the like in addition to these above-described components as long as the effects of the present invention are not impaired.
  • the solvent examples include aprotic polar solvents such as N-methyl-2-pyrrolidone, N, N-dimethylformamide, N, N-dimethylacetamide, dimethyl sulfoxide, hexamethylphosphorylamide, tetramethylene sulfone, and ⁇ -butyrolactone. These solvents may be used alone or in combination of two or more.
  • the content of the solvent is preferably 20 to 90% by weight based on the total amount of the photosensitive polymer composition.
  • the photosensitive polymer composition of the present invention can contain an appropriate surfactant or leveling agent in order to improve the coatability, for example, to improve the developability by preventing film thickness unevenness (striation).
  • surfactants or leveling agents include polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, polyoxyethylene oleyl ether, polyoxyethylene octyl phenol ether, and specific commercial products include Megafax F171, F173, R-08 (trade name, manufactured by Dainippon Ink and Chemicals), Florard FC430, FC431 (trade name, Sumitomo 3M), organosiloxane polymers KP341, KBM303, KBM403, KBM803 (Shin-Etsu Chemical Co., Ltd.) Company name).
  • a pattern can be produced by applying the photosensitive polymer composition of the present invention.
  • a pattern having a good shape and excellent sensitivity, resolution, adhesiveness and heat resistance can be obtained.
  • the method for producing a pattern of the present invention includes a step of applying and drying the photosensitive polymer composition of the present invention on a support substrate, a step of exposing, a step of developing, and a step of heat treatment.
  • Examples of the support substrate to which the composition of the present invention is applied include a glass substrate, an aluminum substrate, a semiconductor, a metal oxide insulator (for example, TiO 2 , SiO 2, etc.), silicon nitride, and the like.
  • Examples of the coating method include a coating method such as a spinner, and a photosensitive polymer film can be formed by drying the composition of the present invention using a hot plate, an oven or the like after spin coating.
  • the photosensitive polymer composition formed as a film on the support substrate is irradiated with actinic rays such as ultraviolet rays, visible rays, and radiations through a mask.
  • actinic ray light source is preferably i-line.
  • the pattern film is obtained by removing the exposed portion with a developer.
  • a developer for example, an alkaline aqueous solution such as sodium hydroxide, potassium hydroxide, sodium silicate, ammonia, ethylamine, diethylamine, triethylamine, triethanolamine, tetramethylammonium hydroxide is preferable, and the base concentration of these aqueous solutions is 0.1 to 10% by weight is preferable.
  • the developer may further contain alcohols and / or surfactants, and these are preferably 0.01 to 10 parts by weight, and 0.1 to 5 parts by weight with respect to 100 parts by weight of the developer. It is more preferable that
  • the pattern coating is thermally cured, and a heat-resistant polyoxazole pattern cured film having an oxazole ring or other functional group is obtained.
  • the temperature of the heat treatment is preferably 150 to 450 ° C.
  • FIG. 1 to 5 are schematic cross-sectional views for explaining a manufacturing process of a semiconductor device having a multilayer wiring structure, and show a series of processes from a first process to a fifth process.
  • a semiconductor substrate 1 such as a Si substrate having a circuit element (not shown) is covered with a protective film 2 such as a silicon oxide film except for a predetermined portion of the circuit element, and is exposed on the exposed circuit element.
  • a first conductor layer 3 is formed.
  • a film made of polyimide resin or the like as the interlayer insulating film layer 4 is formed on the semiconductor substrate 1 by a spin coating method or the like (first step, FIG. 1).
  • a photosensitive resin layer 5 such as chlorinated rubber or phenol novolac is formed on the interlayer insulating film layer 4 as a mask by a spin coating method, and a predetermined portion of the interlayer insulating film layer 4 is formed by a known photolithography technique.
  • a window 6A is provided so as to be exposed (second step, FIG. 2).
  • the interlayer insulating film layer 4 exposed to the window 6A is selectively etched by a dry etching means using a gas such as oxygen or carbon tetrafluoride to open the window 6B.
  • the photosensitive resin layer 5 is completely removed using an etching solution that corrodes only the photosensitive resin layer 5 without corroding the first conductor layer 3 exposed from the window 6B (third step, FIG. 3).
  • the second conductor layer 7 is formed using a known photolithography technique, and the electrical connection with the first conductor layer 3 is completely performed (fourth step, FIG. 4).
  • each layer can be formed by repeating the above steps.
  • the surface protective film 8 is formed.
  • the photosensitive polymer composition of the present invention is applied and dried by a spin coating method, irradiated with light from a mask on which a pattern for forming a window 6C is formed at a predetermined portion, and then developed with an alkaline aqueous solution. Then, a pattern film is formed. Then, this pattern film is heated to form a pattern cured film as the surface protective film layer 8 (fifth step, FIG. 5).
  • the surface protective film layer 8 protects the conductor layer from external stress, ⁇ rays, etc., and the resulting semiconductor device is excellent in reliability. In addition, you may form the said interlayer insulation film using the photosensitive polymer composition of this invention.
  • the photosensitive polymer composition of the present invention can be used for electronic parts such as semiconductor devices and multilayer wiring boards, and specifically, surface protection films and interlayer insulating films of semiconductor devices, and interlayer insulation of multilayer wiring boards. It can be used for forming a film or the like.
  • the electronic component of the present invention is not particularly limited except that it has a surface protective film or an interlayer insulating film formed using the photosensitive polymer composition of the present invention, and can have various structures.
  • Synthesis example 1 [Synthesis of Polybenzoxazole Precursor (Component (a))] In a 0.5 liter flask equipped with a stirrer and a thermometer, 15.48 g of 4,4′-diphenyl ether dicarboxylic acid and 90 g of N-methylpyrrolidone were charged, and the flask was cooled to 5 ° C., and then 12.64 g of thionyl chloride. Was added dropwise and reacted for 30 minutes to obtain a solution of 4,4′-diphenyl ether dicarboxylic acid chloride.
  • N-methylpyrrolidone 87.5 g was charged into a 0.5 liter flask equipped with a stirrer and a thermometer, and 18.30 g of bis (3-amino-4-hydroxyphenyl) hexafluoropropane was added and stirred. After dissolution, 8.53 g of pyridine was added, and while maintaining the temperature at 0 to 5 ° C., a solution of 4,4′-diphenyl ether dicarboxylic acid chloride was added dropwise over 30 minutes, and then stirring was continued for 30 minutes.
  • polybenzoxazole precursor polybenzoxazole precursor
  • Synthesis example 2 [Synthesis of polyimide precursor (component (a)) In a 0.2 liter flask equipped with a stirrer and a thermometer, 10 g (32 mmol) of 3,3 ′, 4,4′-diphenyl ether tetracarboxylic dianhydride (ODPA) and 3.87 g (65 mmol) of isopropyl alcohol were added. Was dissolved in 45 g of N-methylpyrrolidone, and a catalytic amount of 1,8-diazabicycloundecene was added, followed by heating at 60 ° C. for 2 hours, followed by stirring at room temperature (25 ° C.) for 15 hours. Esterification was performed. Thereafter, 7.61 g (64 mmol) of thionyl chloride was added under ice cooling, and the mixture was returned to room temperature and reacted for 2 hours to obtain an acid chloride solution.
  • ODPA 4,4′-diphenyl ether tetrac
  • the weight average molecular weight of the polymer I determined by GPC standard polystyrene conversion was 14580, and the degree of dispersion was 1.6.
  • the polymer II had a weight average molecular weight of 19,400 and a dispersity of 2.2.
  • Example 1-18 and Comparative Example 1-7 (A) 100 parts by weight of the polymers I and II prepared in Synthesis Examples 1 and 2 as components and (b) component, (c) component, (d) component and (e) component as shown in Tables 1 and 2, respectively.
  • the compounds shown were dissolved in a solvent in which ⁇ -butyrolactone / propylene glycol monomethyl ether acetate was mixed at a weight ratio of 9: 1 in the blending amounts shown in Tables 1 and 2 to prepare photosensitive polymer compositions, respectively.
  • the numbers in the tables in the columns of (b), (c), (d) and (e) indicate the amount added (parts by weight) relative to 100 parts by weight of component (a). .
  • the usage-amount of the solvent was 1.5 times with respect to 100 weight part of (a) component in any case.
  • the prepared photosensitive polymer composition was evaluated by the following methods for storage stability, sensitivity, ratio of dissolution rate between unexposed and exposed areas (contrast), resolution, and plating solution resistance. The results are shown in Tables 1 and 2.
  • the prepared photosensitive polymer composition was spin coated on a silicon wafer and heated at 120 ° C. for 3 minutes to form a coating film having a dry film thickness of 7 to 12 ⁇ m.
  • i-line exposure 100 to 1000 mJ / cm 2 was performed on the coating film through an interference filter.
  • development was performed with a 2.38 wt% aqueous solution of tetramethylammonium hydroxide (TMAH) until the exposed silicon wafer was exposed, followed by rinsing with water, and the remaining film ratio (ratio of film thickness before and after development) was 80.
  • TMAH tetramethylammonium hydroxide
  • the unexposed area and the prepared photosensitive polymer composition were spin coated on a silicon wafer and dried at 120 ° C. for 3 minutes to form a coating film having a dry film thickness of 7 to 12 ⁇ m.
  • the coating film was developed with a 2.38 wt% aqueous solution of methylammonium hydroxide (TMAH) for 100 seconds, rinsed with water, and the dissolution rate of the unexposed area was determined from the difference in film thickness before and after development.
  • TMAH methylammonium hydroxide
  • the coating film prepared in the same manner was subjected to 200 mJ / cm 2 i-line exposure through an interference filter using an ultrahigh pressure mercury lamp.
  • TMAH tetramethylammonium hydroxide
  • the prepared photosensitive polymer composition was spin-coated on a silicon wafer on which aluminum was deposited, and then heated at 120 ° C. for 3 minutes to form a coating film having a thickness of 8 ⁇ m. This coating film was exposed and developed to form a pattern. The formed pattern was heated in an inert gas oven at 100 ° C. for 60 minutes in a nitrogen atmosphere, and then heated at 320 ° C. for 1 hour to obtain a cured film. The cured film patterned on the aluminum substrate was mixed at 23 ° C.
  • the presence or absence of the chemical solution permeating into the interface between the substrate and the resin layer from the opening pattern was evaluated by observation with a metal microscope from above.
  • the case where the penetration was confirmed to be 2 ⁇ m or more with a metal microscope was evaluated as “X”, the case where the penetration was 0.5 ⁇ m or more and less than 2 ⁇ m was evaluated as “ ⁇ ”, and the case where the penetration was not confirmed at all was evaluated as “ ⁇ ”.
  • the cured films made of the photosensitive polymer compositions of Examples 1 to 18 had good adhesion to the substrate and were at a practical level. That is, the photosensitive polymer composition of the present invention improves the adhesion to the substrate while maintaining a high-contrast and high-resolution and maintaining a good-shaped pattern without reducing storage stability and sensitivity. It can be seen that the positive photosensitive polymer composition has excellent plating solution resistance.
  • Comparative Examples 1 to 5 the adhesion was weak and the chemical solution permeated into the substrate / resin interface, and in Comparative Example 6, the storage stability of the varnish was poor. Further, in Comparative Example 7, the dissolution rate of the exposed area was very slow and no opening was obtained even after 5 minutes of development, so the contrast value could not be obtained.
  • the photosensitive polymer composition of the present invention can be suitably used as a material for a surface protective film or an interlayer insulating film, and can produce highly reliable electronic components with a high yield.

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Abstract

La présente invention se rapporte à une composition polymère sensible à la lumière comprenant : (a) un polymère qui est soluble dans une solution alcaline aqueuse ; (b) un composé qui génère un acide au moyen de la lumière ; (c) un agent d'aide à la liaison de complexe d'aluminium ; et (d) un agent de réticulation ayant un groupe représenté par -CH2OR (R étant un atome d'hydrogène ou un groupe organique monovalent).
PCT/JP2011/000251 2010-01-22 2011-01-19 Composition polymère sensible à la lumière, procédé de fabrication d'un motif et composant électronique WO2011089895A1 (fr)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TWI624730B (zh) * 2012-02-27 2018-05-21 Tokyo Ohka Kogyo Co Ltd 正型光阻組成物、光阻層合體、光阻圖型之製造方法、及連接用端子之製造方法

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2000039714A (ja) * 1998-05-14 2000-02-08 Toray Ind Inc 感光性耐熱性樹脂前駆体組成物
WO2007063721A1 (fr) * 2005-11-30 2007-06-07 Sumitomo Bakelite Co., Ltd. Composition de resine photosensible positive et dispositif semi-conducteur et ecran l’utilisant
JP2008145579A (ja) * 2006-12-07 2008-06-26 Sumitomo Bakelite Co Ltd ポジ型感光性樹脂組成物、硬化膜、保護膜、絶縁膜およびそれを用いた半導体装置、表示体装置。
JP2009175356A (ja) * 2008-01-23 2009-08-06 Hitachi Chemical Dupont Microsystems Ltd 低温硬化用のポジ型感光性樹脂組成物、パターン硬化膜の製造方法及び電子部品
JP2009265520A (ja) * 2008-04-28 2009-11-12 Hitachi Chemical Dupont Microsystems Ltd 感光性樹脂組成物、該樹脂組成物を用いたポリベンゾオキサゾール膜、パターン硬化膜の製造方法及び電子部品

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2000039714A (ja) * 1998-05-14 2000-02-08 Toray Ind Inc 感光性耐熱性樹脂前駆体組成物
WO2007063721A1 (fr) * 2005-11-30 2007-06-07 Sumitomo Bakelite Co., Ltd. Composition de resine photosensible positive et dispositif semi-conducteur et ecran l’utilisant
JP2008145579A (ja) * 2006-12-07 2008-06-26 Sumitomo Bakelite Co Ltd ポジ型感光性樹脂組成物、硬化膜、保護膜、絶縁膜およびそれを用いた半導体装置、表示体装置。
JP2009175356A (ja) * 2008-01-23 2009-08-06 Hitachi Chemical Dupont Microsystems Ltd 低温硬化用のポジ型感光性樹脂組成物、パターン硬化膜の製造方法及び電子部品
JP2009265520A (ja) * 2008-04-28 2009-11-12 Hitachi Chemical Dupont Microsystems Ltd 感光性樹脂組成物、該樹脂組成物を用いたポリベンゾオキサゾール膜、パターン硬化膜の製造方法及び電子部品

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TWI624730B (zh) * 2012-02-27 2018-05-21 Tokyo Ohka Kogyo Co Ltd 正型光阻組成物、光阻層合體、光阻圖型之製造方法、及連接用端子之製造方法

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