WO2007132890A1 - ポジ型感光性樹脂組成物及びそれから得られる多孔質膜 - Google Patents
ポジ型感光性樹脂組成物及びそれから得られる多孔質膜 Download PDFInfo
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- WO2007132890A1 WO2007132890A1 PCT/JP2007/060038 JP2007060038W WO2007132890A1 WO 2007132890 A1 WO2007132890 A1 WO 2007132890A1 JP 2007060038 W JP2007060038 W JP 2007060038W WO 2007132890 A1 WO2007132890 A1 WO 2007132890A1
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- photosensitive resin
- resin composition
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- positive photosensitive
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- 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
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- 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
-
- 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
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
- G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
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- 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
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
- G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
- G03F7/0397—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition the macromolecular compound having an alicyclic moiety in a side chain
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- 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
- G03F7/075—Silicon-containing compounds
- G03F7/0757—Macromolecular compounds containing Si-O, Si-C or Si-N bonds
Definitions
- the present invention relates to a positive photosensitive resin composition, a cured film obtained therefrom, and various materials using the cured film.
- This positive photosensitive resin composition is particularly suitable for use as a bank or interlayer insulating film in a liquid crystal display element or EL display element, as a light shielding material or a partition material corresponding to an ink jet system.
- TFT thin film transistor
- organic EL electrostatic electrowetting
- planarization films patterned electrode protective films and planarization films
- An insulating film or the like is provided.
- the photosensitive resin has the characteristics that the number of steps for obtaining a required pattern shape is small and the force is sufficiently flat.
- the composition has been widely used in the past.
- a full-color display substrate manufacturing technique using an inkjet has been actively studied in recent years.
- a section (hereinafter referred to as a bank) that prescribes a pixel pattern that has been preliminarily defined in comparison with the conventional printing method, electrodeposition method, dyeing method or pigment dispersion method. )
- Is formed with a photosensitive resin layer that blocks light, and a color filter that drops ink droplets into an opening surrounded by the bank and a manufacturing method thereof for example, Patent Document 1, Patent Document 2, and Patent Document) 3
- Patent Document 1 Patent Document 1
- Patent Document 2 Patent Document 3
- a method for manufacturing an organic EL display element in advance is also proposed (for example, see Patent Document 4) in which a bank is prepared in advance and an ink serving as a light emitting layer is dropped in the same manner. .
- the substrate is made hydrophilic by continuous plasma treatment,
- the power process which is supposed to give the bank water repellency is complicated.
- fluorosurfactants and fluoropolymers with photosensitive organic thin films There are many points to consider including not only photosensitivity but also coating properties, such as strength and compatibility. It was difficult to say.
- Patent Document 1 Japanese Patent Laid-Open No. 10-206627
- Patent Document 2 Japanese Patent Laid-Open No. 11-326625
- Patent Document 3 Japanese Patent Laid-Open No. 2000-187111
- Patent Document 4 Japanese Patent Laid-Open No. 11 54270
- the present invention has been made in view of the above circumstances, and the problem to be solved is that the pattern surface has high water repellency, and the water repellency is greatly impaired even after treatment with plasma or the like. It is another object of the present invention to provide a photosensitive resin composition capable of easily forming a film pattern having insulating properties with high accuracy and high throughput.
- the present invention is a cured film obtained using such a positive photosensitive resin composition, and in the production of a substrate using an inkjet, ink droplets are formed on adjacent pixels beyond the bank. It is an object of the present invention to provide a cured film capable of preventing an overflow situation, and various elements and materials made using such a cured film.
- the present invention provides, as a first aspect, a positive photosensitive resin composition containing the following component (A), component (B), component (C), component (D) and solvent (E):
- the positive photosensitive resin composition according to the first aspect wherein the number average molecular weight of the alkali-soluble resin of component (i) is 2,000 to 30,000 in terms of polystyrene,
- the positive-type photosensitive resin composition according to the first aspect or the second aspect wherein the crosslinkable compound of the component (D) is a compound containing a bifunctional or higher functional epoxy group,
- the positive photosensitive resin composition according to any one of the first to third aspects, wherein the crosslinkable compound of component (D) is a compound represented by formula (1): object,
- the solvent is propylene glycol monomethyl ether 1st viewpoint thru
- solvent is propylene glycol monomethyl ether 1st viewpoint thru
- a positive photosensitive resin composition based on 100 parts by mass of component (A), 0.1 to 30 parts by mass of component (B), 5 to 100 parts by mass of component (C) and 1 to 80 parts by mass of component (D)
- a positive photosensitive resin composition according to any one of the first aspect to the fifth aspect, comprising:
- the surfactant is further contained in an amount of 0.2% by mass or less in the positive photosensitive resin composition, according to any one of the first to sixth aspects.
- Positive photosensitive resin composition positive photosensitive resin composition
- the positive photosensitive property according to any one of the first aspect to the seventh aspect.
- a cured film obtained using the greave composition obtained using the greave composition
- a partition material for an organic EL display element having the cured film according to the eighth aspect As a ninth aspect, a partition material for an organic EL display element having the cured film according to the eighth aspect, as a tenth aspect, a liquid crystal display element having the cured film according to the eighth aspect,
- an array flattening film for a liquid crystal display comprising the cured film according to the eighth aspect
- a twelfth aspect is an interlayer insulating film made of the cured film described in the eighth aspect. The invention's effect
- the positive photosensitive resin composition of the present invention has a high storage stability and is a material or pixel for forming a patterned insulating film used for liquid crystal display elements, organic EL display elements, etc. It is suitable as an interval wall material, and it has high water repellency on the pattern surface, and easily forms an insulating porous coating pattern with high accuracy and high throughput that does not significantly reduce the water repellency after ozone treatment. be able to.
- the cured film obtained using the positive photosensitive resin composition of the present invention prevents ink droplets from overflowing to adjacent pixels beyond the bank in the production of a substrate using an ink jet.
- various element materials made using such a cured film can be provided.
- the positive photosensitive resin composition of the present invention comprises (A) an alkali-soluble resin, (B) a siloxane compound, (C) a 1,2-quinonediazide compound. , A crosslinkable compound of component (D), (E) a solvent, and, as desired, other alkali-soluble resin of component (F), surfactant of component (G), or (H) A composition containing an adhesion promoter as component.
- a crosslinkable compound of component (D), (E) a solvent, and, as desired, other alkali-soluble resin of component (F), surfactant of component (G), or (H) A composition containing an adhesion promoter as component.
- the component (A) used in the positive photosensitive resin composition of the present invention includes an unsaturated carboxylic acid, and further an acrylic ester compound, a methacrylic ester compound, a maleimide compound, allyl-tolyl, maleic anhydride, Alcohol-soluble resin that is a polymer (hereinafter referred to as a specific polymer) copolymerized with at least one compound selected from the group strength of styrene compound and beluie compound. [0014] That is, the component (A) used in the present invention has a property of being soluble in an alkaline solution among the specific polymers. As the component (A), one kind or a plurality of kinds of alkali-soluble resins selected from specific copolymer forces having the property of being soluble in such an alkaline solution can be used.
- the specific copolymer must have a polystyrene-equivalent number average molecular weight (hereinafter referred to as a number average molecular weight) force of ⁇ 2,000 to 30,000. It is preferably from 2,500 to 15,000, more preferably from 3,000 to 10,000.
- the shape of the resulting pattern may be poor, the pattern remaining film ratio may decrease, or the heat resistance of the pattern may decrease.
- the number average molecular weight exceeds 30,000, the coating property of the positive photosensitive resin composition becomes poor, the developability deteriorates and it becomes a peel development, and it can be obtained.
- the shape of the pattern may be poor, or the solubility in organic solvents may be reduced.
- the number average molecular weight exceeds 40,000, there may be residues between patterns of 50 m or less, and resolution may be reduced.
- the unsaturated carboxylic acid is not particularly limited, but specific examples include acrylic acid, methacrylic acid, itaconic acid, maleic acid, fumaric acid, crotonic acid. , Mono- (2- (atallyloyloxy) ethyl) phthalate, mono- (2 (methacryloyloxy) ethyl) phthalate, N- (carboxyphenyl) maleimide, N (carboxyphenyl) methacrylamide, N — (Carboxyphenol) acrylamide and the like.
- the monomer component to be copolymerized with such an unsaturated carboxylic acid includes acrylic acid ester compounds, methacrylic acid ester compounds, maleimide compounds, acrylonitrile, maleic acid anhydrides, styrene compounds, and vinyl chloride.
- Compound power is a group power. It is at least one compound selected. Accordingly, one type may be used alone, or a plurality of types may be used in combination.
- a methacrylic acid ester compound In the case where a plurality of types are used in combination, it is preferable to include at least a methacrylic acid ester compound and a maleimide compound, because a cured film can impart high heat resistance. Specific examples of these compounds are listed below.
- Examples of the acrylate compound include methyl acrylate and ethyl acrylate. , Isopropyl acrylate, 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate, glycidyl acrylate, benzyl acrylate, naphthyl acrylate, anthino oleagile, anne !; ⁇ , 2, 2, 2— ⁇ !; Fanoloethyl acrylate, tert butyl acrylate, cyclohexyl acrylate, isobornyl acrylate, 2-methoxyethyl acrylate, methoxytriethylene glycol acrylate , 2 Ethoxyethyl acrylate, tetrahydrofurfuryl acrylate, 3-methoxybutyl acrylate, 2-methyl 2-adamantyl acrylate, 2-propyl-1-adamantyl acrylate, 8-methyl 8- Tricyclodecyl acrylate, 2-methyl
- methacrylic acid ester compounds include methyl methacrylate, ethyl methacrylate, isopropylenomethacrylate, 2-hydroxyethinomethacrylate, 2-hydroxypropinomethacrylate, glycidylmethacrylate, Benzyl methacrylate, naphthyl methacrylate, anthryl methacrylate, anthryl methyl methacrylate, phenol methacrylate, 2, 2, 2-trifluoroethyl methacrylate, tert butyl methacrylate Cyclohexyl metatalylate, isobornyl metatalylate, 2-methoxyethyl methacrylate, 2-methoxyethyl ethylene glycolate, 2-ethoxychetinoremethacrylate, tetrahydrofuranol methacrylate, 3-methoxybutyl methacrylate Taille And 2-methyl-2-adamantyl methacrylate, 2-propyl-2-adamantyl meth
- bur compound examples include bur naphthalene, methyl butyl ether, benzenorevinino reetenole, 2-hydroxyethino levino reetenole, feneno levino reetenole, and propyl butyl ether. .
- styrene compound examples include styrene, methylstyrene, chlorostyrene, bromostyrene, and the like.
- maleimide compounds include maleimide, N-methylmaleimide, N-phenol maleimide, and N-cyclohexyl maleimide.
- the ratio of the unsaturated carboxylic acid is preferably 1 to 30% by mass, more preferably 3 to 25% by mass, and most preferably 5 to 20% by mass. If it is less than 1% by mass, the solubility in an alkali image solution will be insufficient, and if it exceeds 30% by mass, the solubility in an alkali developer will be too high, so that the unexposed area will also be dissolved, resulting in residual film. The rate may decrease
- the method for obtaining the specific copolymer used in the present invention is not particularly limited.
- the unsaturated carboxylic acid power is appropriately selected from at least one monomer, the acrylic acid ester compound, the methacrylic acid ester compound, Maleimide compound, acrylonitrile, maleic anhydride, styrene compound and beryl compound compound group strength At least one selected monomer, optionally other monomers, optionally polymerization initiator, etc. as solvent It is obtained by polymerizing at a temperature of 50 to 110 ° C.
- the solvent used is not particularly limited as long as it dissolves the monomer constituting the specific copolymer and the specific copolymer. Specific examples include the solvents described in (E) Solvent described later.
- the specific copolymer thus obtained is usually in a solution state in which the specific copolymer is dissolved in a solvent.
- the solution of the specific copolymer obtained as described above is re-precipitated by stirring with stirring such as jetyl ether or water, and the generated precipitate is filtered and washed,
- the powder of the specific copolymer can be obtained by drying at normal temperature or heat under pressure or reduced pressure. By such an operation, the polymerization initiator and unreacted monomer coexisting with the specific copolymer can be removed, and as a result, a purified powder of the specific copolymer can be obtained. If sufficient purification is not possible with a single operation, the obtained powder may be redissolved in a solvent and the above operation repeated.
- the powder of the specific copolymer may be used as it is, or the powder is re-dissolved in a solvent such as the solvent (E) described later and used as a solution state. Also good.
- Component (B) is a polysiloxane copolymer having a polystyrene-equivalent number average molecular weight of 100 to 2,000. It is a compound.
- siloxane compounds include linear polydimethylsiloxane resin, branched polydimethylsiloxane resin, cyclic polydimethylsiloxane resin, modified polydimethylsiloxane resin, polydimethylsiloxane copolymer, and the like. Can be mentioned.
- polydimethylsiloxane examples include polydimethylsiloxane, polymethylethylsiloxane, polymethylphenylsiloxane, polymethylhydrogensiloxane, polymethylpropylsiloxane, polydiphenylsiloxane, and polymethylbutylsiloxane.
- Cyclic linear siloxanes or copolymers thereof cyclic polydimethylsiloxane, cyclic polymethylphenylsiloxane, cyclic polymethylhydrogensiloxane, cyclic polymethylethylsiloxane, cyclic polymethylpropylsiloxane, cyclic polymethylbutylsiloxane, etc.
- Non-reactive group-modified polydimethylsiloxane such as siloxane, alkoxy modification, polyether modification, fluorine modification, methylstyryl modification, higher fatty acid ester modification, hydrophilic special modification, higher alkoxy modification, and amino modification Epoxy-modified, carboxy-modified, carbinol-modified, methacryl-modified, mercapto-modified, full Nord modified such reactive group modified polydimethyl white hexane, these copolymers and the like.
- siloxane compounds include, for example, L45 (manufactured by Nippon Car Co., Ltd.), SH200, 510, 550, 710, 705, 1107 (manufactured by Toray, Dowco-Ling Co., Ltd.) , X-22-162C, 3701E, 3710, 1821, 164S, 170DX, 176DX, 164A, 4952, KF96, 50, 54, 99, 351, 618, 910, 700, 6001, 6002, 8010, KR271, 282 (Shin-Etsu Linear siloxane resin such as VS ⁇ Gakku Kogyo Co., Ltd., and cyclic siloxane resins such as VS-7158 (manufactured by Nippon Car Co., Ltd.), B Y11-003 (manufactured by Dow Coung Co., Ltd.) Fat, L-77, 720, 7001, 7604, Y
- the compatibility with the component (A) (alkali-soluble resin), the solubility in the developer, and the upper surface portion of the remaining pattern which is a non-exposed region (light-shielding portion) From the viewpoint of water repellency, those having a polystyrene equivalent number average molecular weight (hereinafter referred to as Mn) of 2,000 or less are preferred. On the other hand, when Mn is small, the water repellency of the surface of the non-exposed area (light-shielding portion) may not be sufficiently obtained, so Mn is preferably 100 or more. Of these, those having a viscosity of 5 to lOOcst are more preferred.
- the siloxane compound as the component (B) is preferably 0.1 to 30 parts by weight, more preferably 1 to 20 parts by weight with respect to 100 parts by weight of the component (A) (alkali-soluble resin). It is particularly preferably used at 3 to 15 parts by mass.
- the amount of the component (B) compound used is less than the lower limit of the above range, the water repellency on the surface of the pattern tends to be insufficient, and the size of the pores formed may be too small. is there.
- the amount of the component (B) compound used exceeds the above range, whitening or film unevenness may occur during coating film formation.
- the size of the pores formed in the coating film can be controlled by appropriately selecting the type of component (B) and the proportion of use thereof.
- the component (C), 1,2-quinonediazide compound is a compound having either a hydroxy group or an amino group, both a hydroxy group and an amino group, and these hydroxyl groups or amino groups. (If having both hydroxy group and amino group, their total amount) amino group of, preferably 10 to 100 mole 0/0, particularly preferably 1 20 to 95 mole%, with 2-quinonediazide sulfonic acid Using esterified or amidated compounds it can.
- Examples of the compound having a hydroxy group include phenol, o-cresol, m-cresol, p-cresol, hydroquinone, resorcinol, catechol, methyl gallate, ethyl gallate, 1, 3, 3 tris (4 hydroxyphenol).
- Examples of the compound containing an amino group include a-line, o-toluidine, m-toluidine, p-toluidine, 4-aminodiphenylmethane, 4-aminodiphenyl, o-phenylenediamine, m-phenylenediamine. , P-phenylenediamine, 4,4'-diaminophenylene methane, 4,4'-diaminodiphenyl ether, and other amino acids, and aminocyclohexane.
- examples of the compound containing both a hydroxy group and an amino group include, for example, o aminophenol, m-aminophenol, ⁇ aminophenol, 4 aminoresorcinol, 2,3-diaminophenol, 2, 4 Diaminophenol, 4, 4'-diamino-4 ''-hydroxytriphenylmethane, 4-amino-1,4-, 4, monohydroxyhydroxymethane, bis (4-amino-3-carboxy-5-hydroxyphenyl) ) Ether, bis (4-amino-3-carboxyl-5-hydroxyphenol) methane, 2, 2 bis (4-amino-3-carboxy-1-hydride) Loxyphenol) propane, 2,2-bis (4 amino-3-carboxy-5-hydroxyphenol) hexafluoropropane and other aminophenols, 2-aminoethanol, 3-aminopropanol, 4-aminocyclo Mention may be made of aranolamines such as xanol.
- 1,2 quinonediazide compounds can be used alone or in combination of two or more.
- the content of the component (C) in the positive photosensitive resin composition of the present invention is preferably 5 to 100 parts by mass, more preferably 8 to 100 parts by mass with respect to 100 parts by mass of the component (A). 50 parts by mass, more preferably 10 to 40 parts by mass.
- the amount is less than 5 parts by mass, the difference in dissolution rate between the exposed portion and the unexposed portion of the positive photosensitive resin composition in the developer may be small, and patterning by development may be difficult. If the amount exceeds 100 parts by mass, the 1,2-quinonediazide compound will not be sufficiently decomposed by exposure in a short time, and the sensitivity will decrease. The transparency of the film may be reduced.
- Component (D) is a compound having crosslinkability with respect to component (A).
- a compound having crosslinkability include a melamine compound or a substituted urea compound having a crosslink forming substituent such as a methylol group or a methoxymethyl group, and a compound containing a crosslink forming substituent such as an epoxy group or an oxetane group. And compounds containing a blocked isocyanate.
- the crosslinkable compound of component (D) is a compound having at least two crosslinkable substituents, and is preferably a compound containing an epoxy group or an oxetane group from the viewpoint of heat resistance and storage stability.
- Such compounds include, for example, tris (2,3 epoxypropyl) isocyanurate, 1,4 butanedioloresigridinoleatenole, 1,2 epoxy4 (epoxyethyl) cyclohexane.
- Glycerol triglycidyl ether diethylene glycol dig dizidinore noetole, 2, 6 digizizino lev noleg !; shigino lee tenole, 1, 1, 3 ⁇ dis [p— (2, 3 epoxypropoxy) phenol] propane, 1 , 2 Cyclohexanedicarboxylic acid diglycidyl ester, 4, 4'-methylenebis (N, N diglycidyl dilin), 3, 4 epoxycyclohexeno retinoyl 3,4-epoxycyclohexane power And trimethylolethane triglycidyl ether and bisphenol mono-A-diglycidyl ether, and pentaerythritol polyglycidyl ether.
- a polymer having an epoxy group can be used as the compound having at least two epoxy groups.
- any polymer having an epoxy group can be used without particular limitation.
- Such a polymer can be produced by addition polymerization using an addition-polymerizable monomer having an epoxy group, and a polymer compound having a hydroxy group and an epoxy group such as epichlorohydrin or glycidyl tosylate. It can be produced by a reaction with a compound having it.
- the weight average molecular weight of such a polymer is, for example, 300 to 200,000.
- At least two epoxy groups and amino Epoxy resins containing a group include YH-434, YH434L (manufactured by Toto Kasei Co., Ltd.), and epoxy resins having a cyclohexene oxide structure are Epolide GT-401, GT-403, and GT.
- E pin Coat (currently jER) 152, 154 above, Japan Epoxy Resin Co., Ltd.
- EPPN201, 202 above, Nippon Kayaku Co., Ltd.
- Etc. as alicyclic epoxy resin, Denacol EX-2 52 (manufactured by Nagase ChemteX Corporation), CY175, CY177, CY179 (above, manufactured by CIBA—GEIG Y AG), Araldite CY—182 CY-192, CY-184 (above, CIBA-GE IGY AG), Epiclon 200, 400 (above, Dainippon Ink Industries, Ltd.), Epicourt (currently jER) 871, 872 ( Japan Epoxy Resin Co., Ltd.), ED-5661, ED-5562 (Celanese Coating Co., Ltd.), etc.
- Polyglycidyl ethers include Denacone EX-611, EX-612, EX-614, EX-622, EX-411, EX-512, EX-522, EX-421, EX-313. , EX-314, EX-321 (manufactured by Nagase ChemteX Corporation), and the like.
- crosslinkable compounds can be used alone or in combination of two or more.
- the compound of component (D) is used in an amount of 1 to 80 parts by weight, preferably 5 to 40 parts by weight, per 100 parts by weight of the alkali-soluble resin of component (A). If the amount of the component (D) compound used is too small below the lower limit of the above range, thermal curing will be insufficient and a satisfactory cured film will not be obtained, while the amount of the compound (D) component used will be If the amount exceeds the upper limit of the above range, the development is insufficient and a development residue is generated.
- the (E) solvent used in the present invention dissolves the (A) component to the (C) component and the (D) component, and dissolves the (F) component to the (H) component, which will be added later if desired.
- the type and structure thereof are not particularly limited.
- Such (E) solvents include, for example, ethylene glycol monomethyl ether, ethylenic glycolenomonotinoreethenore, methinoreserosonolebacetate, ethinorecerosonolevacetate, diethyleneglycolenomonomono Methinore ether, diethyleneglycolenomonoenochinole Ether, Propylene glycol, Propylene glycol monomono methinole ether, Propylene glycol eno monomethino ethenore acetate, Propylene glycol eno propylenoate acetate, Toluene, Xylene, Methyl ethyl ketone, Cyclopentanone, Cyclohexanone 2-heptanone, ⁇ -butyrolatatone, 2-hydroxyethyl propionate, 2-hydroxy 2-methylpropionate, ethoxy acetate, hydroxy acetate, 2-hydroxy-3-
- solvents propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, 2-heptanone, propylene glycol propyl ether, propylene glycol propyl ether acetate, ethyl acetate, butyl lactate, etc. Is preferable from the viewpoint of good and high safety.
- solvents are generally used as solvents for photoresist materials.
- Component (F) is an alkali-soluble rosin other than component (A).
- the alkali soluble resin other than the component (A) is further added to 100 parts by mass of the component (A). Based on this, 1 to 90 parts by mass can be contained.
- component (F) examples include acrylic resins other than component (A) and hydroxystyrene resins, phenol novolac resins, polyamide resins, polyimide precursors, polyimide resins, and the like. Is mentioned.
- Component (G) is a surfactant.
- the positive photosensitive resin composition of the present invention is further improved for the purpose of improving the coating properties as long as the effects of the present invention are not impaired.
- a surfactant may be contained in the surfactant.
- the surfactant of the component (G) is not particularly limited, and examples thereof include fluorine-based surfactants, silicone-based surfactants, and non-ionic surfactants.
- fluorine-based surfactants such as those manufactured by Sumitomo 3EM Co., Ltd., Dainippon Ink & Chemicals, Inc., or Asahi Glass Co., Ltd. can be used. These commercial products are convenient because they are readily available.
- F-top EF301, EF303, EF352 manufactured by Gemco
- MegaFuck F171, F173 manufactured by Dainippon Ink and Chemicals
- Florard FC430, FC431 Suditomo 3EM
- Asahi Guard A G710, Surflon S-382, SC101, SC102, SC103, SC104, SC105, SCIO 6 manufactured by Asahi Glass Co., Ltd.
- the surfactant of component (G) can be used alone or in combination of two or more.
- a surfactant When a surfactant is used, its content is usually 0.2% by mass or less, preferably 0.1% by mass or less, in 100% by mass of the positive photosensitive resin composition. is there. Even if the amount of the component (G) surfactant used is set to an amount exceeding 0.2% by mass, the effect of improving the coating property becomes dull and not economical.
- Component (H) is an adhesion promoter.
- the positive photosensitive resin composition of the present invention may contain an adhesion promoter for the purpose of improving the adhesion with the substrate after development.
- adhesion promoters include chlorosilanes such as trimethylchlorosilane, dimethylvinylchlorosilane, methyldiphenylchlorosilane, and chloromethyldimethylchlorosilane, trimethylenomethoxysilane, dimethylenolegetoxysilane, methinoresinmethoxysilane, Dimethinolevinole alkoxysilanes such as ethoxysilane, diphenyldimethoxysilane, phenyltriethoxysilane, hexamethyldisilazane, N, N, monobis (trimethylsilyl) urea, dimethyltrimethylsilylamine, trimethylsilylimidazole, etc.
- urea such as dimethylurea, 1,3-dimethylurea, or thiourea compounds
- adhesion promoter for example, commercially available compounds such as Shin-Etsu Chemical Co., Ltd., GE Toshiba Silicone Co., Ltd. and Toray Dow Coung Co., Ltd. can be used. Commercial items are readily available.
- component (H) one or more of the above adhesion promoters can be used.
- the amount of these adhesion promoters to be added is usually 20 parts by mass or less, preferably 0.01 to 10 parts by mass, more preferably 0.5 to 10 parts per 100 parts by mass of the component (A). Part by mass. If it is used in an amount of 20 parts by mass or more, the heat resistance of the coating film may be reduced, and if it is less than 0.1 part by mass, the sufficient effect of the adhesion promoter may not be obtained.
- the positive photosensitive resin composition of the present invention is not limited to the effects of the present invention, and may be a rheology modifier, pigment, dye, storage stabilizer, antifoaming agent, or many as necessary. It may contain a dissolution accelerator such as a valent phenol or a polyvalent carboxylic acid.
- the positive photosensitive resin composition of the present invention comprises (A) an alkali-soluble resin, (B) a siloxane compound, (C) a 1,2-quinonediazide compound, (D ) Component crosslinkable compound and (E) a solvent, and optionally, (F) other alkali-soluble resin, (G) surfactant, (H) component It is a composition that can further contain one or more of adhesion promoters and other additives.
- preferred examples of the positive photosensitive resin composition of the present invention are as follows.
- component (A) Based on 100 parts by mass of component (A), 0.1 to 30 parts by mass of component (B), 5 to 100 parts by mass of component (C) and 1 to 80 parts by mass of component (D) A positive photosensitive resin composition containing and dissolving these components in (E) a solvent.
- the component (F) is further based on 100 parts by mass of the component (A), A positive photosensitive resin composition containing 1 to 90 parts by mass.
- a positive photosensitive resin composition further comprising 0.2% by mass or less of component (G) based on 100 parts by mass of component (A) in the composition of [1] or [2] above object.
- the ratio of the solid content in the positive photosensitive resin composition of the present invention is not particularly limited as long as each component is uniformly dissolved in the solvent. For example, 1 to 80% by mass Also, for example, 5 to 60% by mass, or 10 to 50% by mass.
- the solid content is obtained by removing (E) the solvent from all the components of the positive photosensitive resin composition.
- the method for preparing the positive photosensitive resin composition of the present invention is not particularly limited.
- Examples of the method for preparing the positive photosensitive resin composition include (A) component (alkali-soluble resin) in (E) solvent. Dissolve and mix (B) component (siloxane compound), (C) component (1,2-quinonediazide compound), and (D) component (crosslinkable compound) at a prescribed ratio.
- component (F) other alkali-soluble resin
- G component (surfactant)
- H Component (adhesion promoter) and other additives are added and mixed.
- a solution of a specific copolymer obtained by a polymerization reaction in a solvent can be used as it is, and in this case, (A (B), (C), (D), etc. are added to the component solution in the same manner as above to make a uniform solution, and (E) additional solvent is added for the purpose of concentration adjustment. May be.
- the solvent (E) used in the process of forming the specific copolymer and the solvent (E) used for concentration adjustment when preparing the positive photosensitive resin composition may be the same. However, it may be different.
- the prepared positive photosensitive resin composition solution is preferably used after being filtered using a filter having a pore size of about 0.2 m.
- the positive photosensitive resin composition of the present invention is applied to a semiconductor substrate (for example, a silicon z-dioxide-silicon-coated substrate, a silicon nitride substrate, a metal such as aluminum, molybdenum, or chromium).
- a semiconductor substrate for example, a silicon z-dioxide-silicon-coated substrate, a silicon nitride substrate, a metal such as aluminum, molybdenum, or chromium.
- a substrate coated with a glass substrate, a glass substrate, a quartz substrate, an ITO substrate, etc. by spin coating, flow coating, roll coating, slit coating, spin coating following slit, inkjet coating, etc.
- a coating film can be formed by preliminary drying in a hot plate or oven. Thereafter, the coating film is heated to form a positive photosensitive resin film.
- a heating temperature and a heating time appropriately selected from the range of a temperature of 70 ° C to 160 ° C and a time of 0.3 to 60 minutes are employed.
- the heating temperature and heating time are preferably 80 ° C to 140 ° C and 0.5 to 10 minutes.
- the film thickness of the positive photosensitive resin film formed from the positive photosensitive resin composition is, for example, 0.1 to 30 m, and for example, 0.2 to 10 m. For example, te from 0.2 to 5 ⁇ m.
- a mask having a predetermined pattern is mounted, irradiated with light such as ultraviolet rays, and developed with an alkali developer, so that the exposed portion is washed out and the end face is sheared.
- a relief pattern can be obtained.
- alkaline developers examples include aqueous solutions of alkali metal hydroxides such as potassium hydroxide and sodium hydroxide, tetramethylammonium hydroxide, tetraethylammonium hydroxide, and the like.
- alkaline aqueous solutions such as aqueous solutions of quaternary ammonium hydroxides such as urea and choline, and aqueous amine solutions such as ethanolamine, propylamine, and ethylenediamine.
- a surfactant or the like can be added to these developers.
- an aqueous solution of tetraethylammonium hydroxide of 0.1 to 2.38% by mass is generally used as a photoresist developer, and is also used in the photosensitive resin composition of the present invention.
- a good image can be obtained without causing problems such as swelling.
- a V-deviation such as a liquid piling method, a dating method, or a swing dipping method, can also be used.
- the development time is usually 15 to 180 seconds.
- the positive photosensitive resin film is washed with running water, for example, for 20 to 90 seconds, and then air-dried using compressed air or compressed nitrogen or by spinning. The top moisture is removed and a patterned film is obtained.
- the pattern forming film is subjected to post-beta for thermosetting, specifically, by using a hot plate, an oven, or the like, heat resistance, A film having excellent relief pattern with excellent transparency, flatness, low water absorption and chemical resistance can be obtained.
- the post beta is generally 5 to 30 minutes on the hot plate and 3 in the oven at the selected heating temperature at a medium temperature ranging from 140 ° C to 250 ° C. If treated for 0 to 90 minutes, the dredging method is used.
- the positive photosensitive resin composition of the present invention has a sufficiently high sensitivity and a porous pattern having a fine pattern in which the film loss in the unexposed area is very small during image formation.
- a coating film can be formed.
- the cured film obtained from this coating film is porous, has excellent heat resistance and solvent resistance, has high water repellency on the film surface, and its water repellency is greatly impaired even after continuous plasma treatment. It has the feature that there is nothing. For this reason, it is suitable for various applications in liquid crystal displays and organic EL displays such as bank for pixel fractionation, interlayer insulating film, protective film, insulating film, etc. Can be used.
- GMA Glycidylmetatalylate
- DCM Dicyclopentyl methacrylate
- PGMEA Propylene glycol monomethyl ether acetate
- QD 1, 3, 3 A compound synthesized by the condensation reaction of 1 mol of tris (4 hydroxyphenyl) butane and 1 mol of 1,2 naphthoquinone-2-diazido 5-sulfururyl chloride.
- Eporide GT-401 Epoxy-butanetetracarboxylic acid tetrakis (3-cyclohexyl-methyl) modified ⁇
- PDMS1 Polydimethylsiloxane hydroxy terminal ⁇ : 550
- PDMS2 Polydimethylsiloxane—co-polydiphenylsiloxane hydroxy-terminated
- PDMS4 Polydimethylsiloxane diglycidyl ether terminated Mn980
- PDMS5 Polydimethylsiloxane Bishydroxyalkyl terminal Mn: 5,600
- PDMS6 Polydimethylsiloxane dibule terminal Mn: 250, 000
- PDMS7 Polydimethylsiloxane hydroxy-terminated Mn: 8,000
- the number average molecular weight and the weight average molecular weight of the specific copolymer and the specific cross-linked product obtained according to the following synthesis examples were measured using a GPC apparatus (Shodex (registered trademark) columns KF8 03L and KF804L) manufactured by JASCO Corporation. The measurement was performed under the condition that elution solvent tetrahydrofuran was allowed to flow through a column at a flow rate of 1 mlZ (column temperature 40 ° C) for elution.
- Mn number average molecular weight
- Mw weight average molecular weight
- MAA 10.9g, CHMI 35.3g, HEMA 25.5g, MMA 28.3g are used as monomer components constituting the specific copolymer, AIBN 5g is used as radical polymerization initiator, and these are used as solvent PGMEA 200g.
- MAA 23.0g, GMA 40.Og, DCM 37.Og are used as the monomer component constituting the specific copolymer, and AIBN 5g is used as the radical polymerization initiator, and these are heated at a temperature of 60 ° in 200g of solvent PGMEA.
- PGMEA solvent PGMEA
- a transparent and homogeneously dissolved product was prepared both after preparation of this composition and after storage for 1 month at room temperature.
- X was defined as white turbidity or insoluble precipitates or gelled after storage for 1 month or after storage.
- a positive photosensitive resin composition is applied onto a silicon wafer using a spin coater and then pre-baked on a hot plate at a temperature of 110 ° C for 120 seconds to obtain a film thickness of 2.5 ⁇
- the coating film was formed.
- the film thickness was measured using F20 manufactured by FILMETRICS.
- the coated film Canon KK ultraviolet irradiation apparatus PLA-600FA light intensity at 365nm with is irradiated with ultraviolet rays 5. 5mWZcm 2 fixed time.
- the film was developed by immersing it in an aqueous solution of 0.4% by mass of tetramethylammonium hydroxide (hereinafter referred to as TMAH) for 60 seconds, followed by washing with ultrapure water for 20 seconds.
- TMAH tetramethylammonium hydroxide
- pre-beta is applied on a hot plate for 120 seconds at a temperature of 110 ° C. 2.
- the coating film was formed. This membrane was immersed in a 0.4 mass% TMAH aqueous solution for 60 seconds, and then washed with running ultrapure water for 20 seconds. Next, by measuring the thickness of this film, the degree of film reduction in the unexposed area due to development was evaluated. The film thickness in this evaluation was measured using F20 manufactured by FILMETRICS.
- pre-beta is applied on a hot plate for 120 seconds at a temperature of 110 ° C. 2.
- the coating film was formed. This coating film was heated at 230 ° C. for 30 minutes to perform post-beta, and a cured film having a thickness of 1.9 m was formed. The contact angle of water and methylene iodide on the cured film was measured using Drop Master manufactured by Kyowa Interface Science Co., Ltd.
- pre-beta is applied on a hot plate for 120 seconds at a temperature of 110 ° C. 2.
- the coating film was formed. This coating film was heated at 230 ° C. for 30 minutes to perform post-beta, and a cured film having a thickness of 1.9 m was formed. This coating film was cleaned with ozone for 5 minutes using UV-312 manufactured by Technovision Co., Ltd. The contact angle of water on the ozone-cleaned membrane was measured using a Drop Master manufactured by Kyowa Interface Science Co., Ltd.
- a positive photosensitive resin composition was applied onto a silicon wafer using a spin coater. After that, pre-beta was performed on a hot plate at a temperature of 110 ° C for 120 seconds.
- the coating film was formed. This coating film was post-baked by heating at 230 ° C. for 30 minutes to form a cured film having a thickness of 1.9 m.
- the cross section of this coating was scanned using a scanning electron microscope (hereinafter referred to as SE
- pre-beta was applied on a hot plate at a temperature of 110 ° C for 120 seconds to form a coating film having a thickness of 2. m.
- This coating film was post-baked by heating at 230 ° C. for 30 minutes to form a cured film having a thickness of 1.5 m.
- a 0.28 cm 2 A1 pattern was vacuum deposited on this coating film. The dielectric constant at 100 kHz was measured using this substrate.
- the positive photosensitive resin compositions of Examples 1 to 4 are all highly sensitive, and the film loss in the unexposed area is very small. In any case, the surface has high water repellency, and further, voids are formed in the film, which is low. The dielectric constant is shown.
- Comparative Examples 2 to 4 the positive photosensitive resin composition had low solution stability and was unable to obtain a uniform solution.
- Comparative Example 6 a homogeneous solution was obtained, but gelled during storage at room temperature.
- the positive photosensitive resin composition of Comparative Example 1 has high sensitivity and small film loss in the unexposed area, but has low water repellency and plasma treatment resistance on the film surface, and also forms voids in the film. Was not.
- the positive photosensitive resin compositions of Comparative Examples 5 and 7 are highly sensitive, have a small film loss in the unexposed areas, and have a higher water repellency, but have a low UV plasma resistance and are in the film. No voids were formed, and no decrease in dielectric constant was observed.
- the positive photosensitive resin composition according to the present invention is used as a material for forming a hardened film such as a protective film, a planarizing film, and an insulating film in various displays such as thin film transistor (TFT) type liquid crystal display elements and organic EL elements.
- TFT thin film transistor
- an interlayer insulating film of a TFT type liquid crystal element, a protective film for a color filter, an array flat film, an uneven film under a reflective film of a reflective display, an insulating film of an organic EL element, etc. are formed. It is also suitable as a material, and also suitable as various electronic materials such as a microlens material.
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Abstract
Description
Claims
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KR (1) | KR20090010044A (ja) |
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WO2018194166A1 (ja) * | 2017-04-21 | 2018-10-25 | 日産化学株式会社 | 感光性樹脂組成物 |
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KR101998447B1 (ko) * | 2012-03-09 | 2019-07-09 | 에이지씨 가부시키가이샤 | 포지티브형 감광성 수지 조성물, 격벽 및 광학 소자 |
KR20140134662A (ko) * | 2012-03-09 | 2014-11-24 | 아사히 가라스 가부시키가이샤 | 포지티브형 감광성 수지 조성물, 격벽 및 광학 소자 |
JPWO2013133392A1 (ja) * | 2012-03-09 | 2015-07-30 | 旭硝子株式会社 | ポジ型感光性樹脂組成物、隔壁及び光学素子 |
CN103885294B (zh) * | 2012-12-20 | 2017-07-14 | 奇美实业股份有限公司 | 感光性聚硅氧烷组成物、保护膜及具有保护膜的元件 |
CN103885294A (zh) * | 2012-12-20 | 2014-06-25 | 奇美实业股份有限公司 | 感光性聚硅氧烷组成物、保护膜及具有保护膜的元件 |
WO2018194166A1 (ja) * | 2017-04-21 | 2018-10-25 | 日産化学株式会社 | 感光性樹脂組成物 |
WO2018194169A1 (ja) * | 2017-04-21 | 2018-10-25 | 日産化学株式会社 | 感光性樹脂組成物 |
CN110573963A (zh) * | 2017-04-21 | 2019-12-13 | 日产化学株式会社 | 感光性树脂组合物 |
JPWO2018194169A1 (ja) * | 2017-04-21 | 2020-02-27 | 日産化学株式会社 | 感光性樹脂組成物 |
JPWO2018194166A1 (ja) * | 2017-04-21 | 2020-02-27 | 日産化学株式会社 | 感光性樹脂組成物 |
JP7045001B2 (ja) | 2017-04-21 | 2022-03-31 | 日産化学株式会社 | 感光性樹脂組成物 |
JP7239895B2 (ja) | 2017-04-21 | 2023-03-15 | 日産化学株式会社 | 感光性樹脂組成物 |
CN110573963B (zh) * | 2017-04-21 | 2023-10-24 | 日产化学株式会社 | 感光性树脂组合物 |
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TW200813635A (en) | 2008-03-16 |
KR20090010044A (ko) | 2009-01-28 |
JPWO2007132890A1 (ja) | 2009-09-24 |
CN101443704A (zh) | 2009-05-27 |
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