WO2009113490A1 - 感放射線性樹脂組成物 - Google Patents
感放射線性樹脂組成物 Download PDFInfo
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- WO2009113490A1 WO2009113490A1 PCT/JP2009/054421 JP2009054421W WO2009113490A1 WO 2009113490 A1 WO2009113490 A1 WO 2009113490A1 JP 2009054421 W JP2009054421 W JP 2009054421W WO 2009113490 A1 WO2009113490 A1 WO 2009113490A1
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- radiation
- resin 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
- G03F7/022—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
- G03F7/0236—Condensation products of carbonyl compounds and phenolic compounds, e.g. novolak resins
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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
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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
- G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
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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
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
- G03F7/0382—Macromolecular compounds which are rendered insoluble or differentially wettable the macromolecular compound being present in a chemically amplified negative 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
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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
- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/40—Treatment after imagewise removal, e.g. baking
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- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
Definitions
- the radiation sensitive resin composition is used not only as a resist mask but also as a component of an electronic device.
- the organic electroluminescent element is highly visible due to self-emission, and because it is a complete solid element, it has features such as excellent impact resistance. It includes structures such as insulating films.
- the radiation-sensitive resin film has (1) a cross-sectional shape that is a forward taper shape, and (2) heat baking at 230 ° C. or lower temperature, (3) It is required that there is little outgas from the resin film after heating and baking.
- JP-A-5-94013 JP 2001-75272 A Japanese Patent Laid-Open No. 1-60630 Japanese Patent Laid-Open No. 3-209478 JP 2005-196130 A Japanese Laid-Open Patent Publication No. 2002-169277 JP 2006-201653 A
- an organic electroluminescence device having a radiation lithography structure using the radiation sensitive resin composition.
- the radiation sensitive resin composition of the present invention contains a novolak resin (A) having a repeating unit represented by the general formula (1).
- R1 to R3 each independently represent a hydrogen atom, a hydroxyl group, an alkoxyl group having 1 to 2 carbon atoms (methoxy, ethoxy, etc.) or an alkyl group having 1 to 10 carbon atoms, preferably A hydroxyl group and an alkyl group having 1 to 4 carbon atoms (methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, etc.), more preferably a hydroxyl group or a methyl group.
- the novolak resin (A) used in the present invention can be obtained by reacting phenols with aldehydes or ketones in the presence of an acidic catalyst (for example, oxalic acid or p-toluenesulfonic acid).
- an acidic catalyst for example, oxalic acid or p-toluenesulfonic acid.
- phenols pyrogallol or m-cresol and other phenols such as p-cresol, 2,4-xylenol, 2,5-xylenol and 3,5-xylenol from the viewpoint of the performance of the obtained insulating film. It is preferable to use in combination with at least one selected from 5-xylenol.
- the weight ratio of m-cresol to the other phenols is preferably 25:75 to 85:15, more preferably 30:70 to 70:30.
- aldehydes examples include formaldehyde, formalin, paraformaldehyde, acetaldehyde, propionaldehyde, benzaldehyde, phenylacetaldehyde, ⁇ -phenylpropionaldehyde, ⁇ -phenylpropionaldehyde, o-hydroxybenzaldehyde, m-hydroxybenzaldehyde, p-hydroxy.
- Examples include benzaldehyde, o-chlorobenzaldehyde, m-chlorobenzaldehyde, p-chlorobenzaldehyde, o-methylbenzaldehyde, m-methylbenzaldehyde, p-methylbenzaldehyde, p-ethylbenzaldehyde, pn-butylbenzaldehyde, terephthalaldehyde, and the like.
- ketones include acetone, methyl ethyl ketone, diethyl ketone, and diphenyl ketone. These can be used alone or in combination of two or more.
- R4 and R5 are only hydrogen atoms after the reaction (for example, formaldehyde) are used alone, at least a part of R4 and R5 in the entire repeating unit represented by the general formula (1) is: Since the conditions that are a methyl group, a phenyl group, or a hydroxyphenyl group are not satisfied, at least a part of R4 and R5 can be a methyl group, a phenyl group, or a hydroxyphenyl group (for example, a corresponding aldehyde among the above) It is necessary to use at least one kind.
- the radiation-sensitive resin composition of the present invention contains a heat-reactive compound (B) in order to cure the coating film by heat baking.
- the heat-reactive compound (B) used in the composition of the present invention is at least one compound selected from the group consisting of benzoxazine compounds, carbodiimide compounds, triazine thiol compounds, and bismaleimide compounds.
- a triazine thiol compound and a bismaleimide compound are preferable.
- the benzoxazine compound is not particularly limited, and a compound having a benzoxazine ring (monomer, oligomer or polymer) can be used, and examples thereof include compounds disclosed in JP-A-2006-335671. Moreover, a commercial item can also be used.
- the carbodiimide compound is not particularly limited, and a compound having a carbodiimide group can be used, and a commercially available product can also be used.
- a carbodilite (trade name, manufactured by Nisshinbo Co., Ltd.) series or the like can be used.
- triazine thiol compound examples include 2,4,6-trithiol-1,3,5-triazine, 2-dimethylamino-4,6-dithiol-1,3,5-triazine, 2-dibutylamino-4,6- Examples include dithiol-1,3,5-triazine, 2-phenylamino-4,6-dithiol-1,3,5-triazine and the like.
- the blending amount of the thermally reactive compound (B) is preferably 0.1 to 15 parts by weight per 100 parts by weight of the novolak resin (A) from the viewpoint of alkali solubility, preferably 0.5 to 10 parts by weight is more preferable.
- the radiation-sensitive resin composition of the present invention may be a positive radiation lithography composition or a negative radiation lithography composition.
- naphthoquinone diazide sulfonate As the naphthoquinone diazide sulfonic acid ester, a compound in which all or part of the hydroxyl groups of the polyphenol is esterified with 1,2-quinone diazide sulfonic acid can be used. Specifically, a compound in which 20 to 100% of the hydroxyl group of the polyhydric phenol is esterified with 1,2-quinonediazidesulfonic acid can be used.
- Esterified product of trihydroxybenzophenone and 1,2-quinonediazidesulfonic acid Specific examples include 2,3,4-trihydroxybenzophenone-1,2-naphthoquinonediazide-4-sulfonic acid ester, , 3,4-Trihydroxybenzophenone-1,2-naphthoquinonediazide-5-sulfonic acid ester, 2,4,6-trihydroxybenzophenone-1,2-naphthoquinonediazide-4-sulfonic acid ester, 2,4,6 -Trihydroxybenzophenone-1,2-naphthoquinonediazide-5-sulfonic acid ester and the like.
- Esterified product of bis (2,4′-dihydroxyphenyl) methane and 1,2-naphthoquinonediazidesulfonic acid specific examples include bis (2,4′-dihydroxyphenyl) methane-1,2 -Naphthoquinonediazide-4-sulfonic acid ester, bis (2,4'-dihydroxyphenyl) methane-1,2-naphthoquinonediazide-5-sulfonic acid ester, and the like.
- (c.7) Esterified product of tri (p-hydroxyphenyl) methane and 1,2-naphthoquinonediazidesulfonic acid:
- Esterified product of 1,1,1-tri (p-hydroxyphenyl) ethane and 1,2-naphthoquinonediazidesulfonic acid specific examples include 1,1,1-tri (p-hydroxyphenyl) And ethane-1,2-naphthoquinonediazide-4-sulfonic acid ester, 1,1,1-tri (p-hydroxyphenyl) ethane-1,2-naphthoquinonediazide-5-sulfonic acid ester, and the like.
- Esterified product of bis (2,3,4-trihydroxyphenyl) methane and 1,2-naphthoquinonediazidesulfonic acid specific examples include bis (2,3,4-trihydroxyphenyl) methane -1,2-naphthoquinonediazide-4-sulfonic acid ester, bis (2,3,4-trihydroxyphenyl) methane-1,2-naphthoquinonediazide-5-sulfonic acid ester, and the like.
- quinonediazide group-containing compounds such as orthobenzoquinonediazide, orthonaphthoquinonediazide, orthoanthraquinonediazide or orthonaphthoquinonediazidesulfonic acid esters and their nucleus-substituted derivatives; orthonaphthoquinonesulfonylsulfonyl and a compound having a hydroxyl group or an amino group
- orthobenzoquinonediazide orthonaphthoquinonediazide, orthoanthraquinonediazide or orthonaphthoquinonediazidesulfonic acid esters and their nucleus-substituted derivatives
- orthonaphthoquinonesulfonylsulfonyl and a compound having a hydroxyl group or an amino group
- the reaction product of can also be used.
- Examples of the compound having a hydroxyl group or an amino group include phenol, p-methoxyphenol, dimethylphenol, hydroquinone, bisphenol A, naphthol, carbinol, pyrocatechol, pyrogallol, pyrogallol monomethyl ether, pyrogallol-1,3-dimethyl ether, and gallic acid.
- examples thereof include gallic acid, aniline, p-aminodiphenylamine and the like which are esterified or etherified while leaving a part of the acid or hydroxyl group.
- 1,2-quinonediazide sulfonic acid esters as described above, for example, esterify a halide of 1,2-quinonediazide sulfonic acid with a corresponding polyphenol (polyhydric hydroxy compound) in the presence of a base catalyst. Can be obtained.
- 2,3,4,4′-tetrahydroxybenzophenone-1,2-naphthoquinonediazide-5-sulfonic acid ester as described above is 2,3,4,4′-tetrahydroxybenzophenone.
- 1,2-quinonediazide-5-sulfonic acid chloride is 1,2-quinonediazide-5-sulfonic acid chloride.
- the blending amount of the radiation sensitive compound (C) varies depending on the compound used.
- the compound used for example, in the case of naphthoquinone diazide sulfonate, 1 to 100 parts by weight of the novolak resin (A) 30 parts by weight is preferable, and 10 to 25 parts by weight is more preferable.
- the radiation sensitive compound (C) for example, a photoacid generator that generates an acid by radiation, such as an onium salt, a halogen-containing compound, a diazomethane compound, a sulfone compound, or a sulfonic acid compound is used.
- an onium salt include iodonium salts, sulfonium salts, diazonium salts, ammonium salts, pyridinium salts and the like with triflate or hexaflate.
- Halogen-containing compounds include haloalkyl group-containing hydrocarbon compounds or haloalkyl group-containing heterocycles.
- Formula compounds such as (trichloromethyl) -s-triazine derivatives such as phenyl-bis (trichloromethyl) -s-triazine, methoxyphenyl-bis (trichloromethyl) -s-triazine, tribromoneopentyl alcohol, hexabromo
- examples thereof include bromine compounds such as hexane and iodine compounds such as hexaiodohexane.
- Examples of the diazomethane compound include bis (trifluoromethylsulfonium) diazomethane and bis (cyclohexylsulfonium) diazomethane.
- Examples of the sulfone compound include ⁇ -ketosulfone and ⁇ -sulfonylsulfone.
- Examples of the sulfonic acid compound include alkyl (C 1-12 ) sulfonic acid ester, haloalkyl (C 1-12 ) sulfonic acid ester, and arylsulfonic acid. Examples thereof include esters and iminosulfonates. These photoacid generators can be used alone or in admixture of two or more.
- the blending amount of the radiation sensitive compound (C) varies depending on the compound used, but the blending amount is 0.1 to 10 parts by weight per 100 parts by weight of the novolak resin (A). It is preferably 0.5 to 5.0 parts by weight.
- the radiation sensitive resin composition of the present invention is dissolved in a solvent (D) and used in a solution state.
- the novolak resin (A) is dissolved in the solvent (D), and the heat-reactive compound (B) and the radiation-sensitive compound (C), and, if necessary, the surfactant (E) or the dye,
- a radiation-sensitive resin composition in a solution state can be prepared by mixing a dye (F) such as a pigment at a predetermined ratio immediately before use.
- Examples of the solvent (D) include alcohols such as methanol and ethanol; ethers such as tetrahydrofuran; glycol ethers such as ethylene glycol monomethyl ether, ethylene glycol dimethyl ether, ethylene glycol methyl ethyl ether, and ethylene glycol monoethyl ether; Ethylene glycol alkyl ether acetates such as methyl cellosolve acetate and ethyl cellosolve acetate; diethylene glycols such as diethylene glycol monomethyl ether, diethylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol ethyl methyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether; Propylene glycol alkyl ether acetates such as pyrene glycol methyl ether acetate and propylene glycol ethyl ether acetate; aromatic hydrocarbons such as toluen
- glycol ethers alkylene glycol alkyl ether acetates, diethylene glycol dialkyl ethers and diethylene glycols are preferred. More preferred are ethyl 3-ethoxypropionate, ethyl lactate, propylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, methyl amyl ketone, and diethylene glycol ethyl methyl ether.
- These solvents may be used alone or in combination of two or more.
- the radiation-sensitive resin composition of the present invention is an optional component in addition to the above essential components, for example, to prevent striation (after application streaking) and improve applicability, or to improve the developability of the coating film.
- a surfactant (E) can be contained.
- surfactant (E) examples include polyoxyethylene alkyl ethers such as polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, polyoxyethylene oleyl ether; polyoxyethylene octylphenyl ether, polyoxyethylene
- Nonoxy surfactants such as polyoxyethylene aryl ethers such as nonylphenyl ether; polyoxyethylene dialkyl esters such as polyoxyethylene dilaurate and polyoxyethylene distearate; F-top EF301, 303 and 352 (and above) , Trade name, manufactured by Shin-Akita Kasei Co., Ltd.), MegaFuck F171, F172, F173, R-08, R-30 (above, trade name, manufactured by Dainippon Ink & Chemicals, Inc.), Florer FC-430, FC-431 (above, trade name, manufactured by Sumitomo 3M Limited), Asahi Guard AG710, Surflon S-382, SC-101, SC-102, SC-103
- Such a surfactant is blended in an amount of 2 parts by weight or less, preferably 1 part by weight or less based on 100 parts by weight of the radiation-sensitive resin composition.
- the radiation-sensitive resin composition of the present invention can contain a dye (F) such as a dye or pigment as an optional component.
- a dye (F) such as a dye or pigment as an optional component.
- the dye (F) such as a dye or pigment may be an inorganic pigment or an organic pigment.
- the composition of the present invention is prepared using the solvent (D), and an appropriate solid content concentration can be adopted depending on the intended use.
- the solid content concentration is 10 to 50% by weight. it can.
- the composition liquid prepared as mentioned above is usually filtered before use.
- the filtering means include a Millipore filter having a pore diameter of 0.05 to 1.0 ⁇ m.
- the radiation-sensitive resin composition solution of the present invention prepared in this way is excellent in long-term storage stability.
- the composition of the present invention is used for radiation lithography, first, the radiation-sensitive resin composition of the present invention is applied to the substrate surface, and the solvent is removed by means such as heating to form a coating film.
- the coating method of the radiation sensitive resin composition to the substrate surface is not particularly limited, and various methods such as a spray method, a roll coating method, a slit method, and a spin coating method can be employed.
- this coating film is usually heated (prebaked).
- the heating conditions vary depending on the type of each component and the blending ratio, etc.
- the film is usually formed by heat treatment at 70 to 120 ° C. for a predetermined time, for example, 1 to 10 minutes on a hot plate, or 10 to 30 minutes in an oven. Obtainable.
- the pre-baked coating film is irradiated with radiation (for example, ultraviolet rays, far ultraviolet rays, X-rays, electron beams, gamma rays, synchrotron radiation, etc.) through a mask having a predetermined pattern, and then developed with a developer. These portions are removed to form a predetermined pattern film.
- radiation for example, ultraviolet rays, far ultraviolet rays, X-rays, electron beams, gamma rays, synchrotron radiation, etc.
- Examples of the developer include inorganic alkalis such as sodium hydroxide, potassium hydroxide, sodium carbonate, sodium silicate, sodium metasilicate, and aqueous ammonia; primary amines such as ethylamine and n-propylamine; Secondary amines such as n-propylamine; tertiary amines such as triethylamine and methyldiethylamine; alcohol amines such as dimethylethanolamine and triethanolamine; tetramethylammonium hydroxide, tetraethylammonium hydroxide, choline and the like Quaternary ammonium salts of the following: cyclic amines such as pyrrole, piperidine, 1,8-diazabicyclo [5,4,0] -7-undecene, 1,5-diazabicyclo [4,3,0] -5-nonane, etc. Alkaline water It can be used.
- cyclic amines such as pyrrole,
- this pattern is cured by heating with a heating device such as a hot plate or oven at a predetermined temperature, for example, 150 to 250 ° C., for a predetermined time, for example, 2 to 30 minutes on the hot plate, or 30 to 90 minutes in the oven.
- a heating device such as a hot plate or oven at a predetermined temperature, for example, 150 to 250 ° C., for a predetermined time, for example, 2 to 30 minutes on the hot plate, or 30 to 90 minutes in the oven.
- a coating can be obtained.
- composition of the present invention can be suitably used, for example, as a positive-type radiation-sensitive resin for forming an insulating film of an organic electroluminescence device.
- a negative-type radiation-sensitive resin composition can be used as an electron. It can be used for part lithography.
- a radiation-sensitive resin composition was prepared with the formulation (parts) shown in Table 2.
- the meanings of the abbreviations in the table are as follows.
- Resins 1 to 6 Novolac resins prepared in (1) above (Resin 1 to Resin 6)
- Benzoxazine compound bisphenol A type benzoxazine carbodiimide compound: bis (2,6-diisopropylphenyl) carbodiimide
- Triazine thiol compound 2,4,6-trithiol-1,3,5-triazine bismaleimide compound: 4,4'-diphenylmethane bismaleimide methylated melamine compound: Methylated melamine epoxy compound manufactured by Sanwa Chemical Co., Ltd .: Nippon Kayaku Bisphenol type epoxy resin quinonediazide compound: 2,3,4,4′-tetrahydroxybenzophenone-1,2-naphthoquinonediazide-5-sulfonic acid ester photoacid
- the obtained patterns were observed with a microscope, and exposure was not confirmed in the space portion in the 50 ⁇ m line and space patterns. The amount was taken as sensitivity.
- the negative radiation-sensitive resin compositions (Examples 21 to 24) could not be evaluated as described above, so only the presence or absence of a pattern was confirmed by microscopic observation.
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Abstract
Description
本発明の放射線リソグラフィー構造物は、加熱焼成後に膜から発生するアウトガスによる発光素子への汚染なしに加工することができる。
本発明の有機電界発光素子は、加熱焼成後の絶縁樹脂膜からのアウトガスが少なく、ダークスポットや画素収縮などの発光不良を生じることがない。
(1)ノボラック樹脂1~6
表1に示した配合でノボラック樹脂(樹脂1~樹脂6)を調製した。
樹脂1:R1~R3=H,H,メチル、R4、R5=H
樹脂2:R1~R3=H,H,メチル、R4、R5=H、フェニル
樹脂3:R1~R3=H,H,メチル、R4、R5=フェニル
樹脂4:R1~R3=H,H,メチル、R4、R5=ヒドロキシフェニル
樹脂5:R1~R3=H,H,メチル、R4、R5=フェニル、ヒドロキシフェニル
樹脂6:R1~R3=OH、R4、R5=メチル
を表す。
表2に示す配合(部)で感放射線性樹脂組成物を調製した。表中の略号の意味は下記のとおり。
樹脂1~6:上記(1)で調製したノボラック樹脂(樹脂1~樹脂6)
ベンゾオキサジン化合物:ビスフェノールA型ベンゾオキサジン
カルボジイミド化合物:ビス(2,6-ジイソプロピルフェニル)カルボジイミド
トリアジンチオール化合物:2,4,6-トリチオール-1,3,5-トリアジン
ビスマレイミド化合物:4,4´-ジフェニルメタンビスマレイミド
メチル化メラミン化合物:三和ケミカル社製メチル化メラミン
エポキシ化合物:日本化薬社製ビスフェノール型エポキシ樹脂
キノンジアジド化合物:2,3,4,4’-テトラヒドロキシベンゾフェノン-1,2-ナフトキノンジアジド-5-スルホン酸エステル
光酸発生剤:2-(p-メトキシスチリル)-4,6-ビス(トリクロロメチル)-s-トリアジン
5インチシリコン基板に、各実施例、比較例で得られた感放射線性樹脂組成物の溶液を、スピンナーを用いて塗布した後、100℃で90秒、ホットプレート上でプリベークして膜厚1.8μmの塗膜を形成した。得られた塗膜を、ニコン製NSR1505g4C縮小投影露光機(NA=0.42、λ=436nm)で露光を行った後、テトラメチルアンモニウムヒドロキシド(TMAH)水溶液にて23℃で60秒間、液盛り法により現像した。その後、流水洗浄し、乾燥してウェハー上にパターンを形成した。さらに、ポジ型感放射線組成物(実施例1~20、比較例1~16)については、得られたパターンを顕微鏡観察し、50μmのラインおよびスペースパターンにおいて、スペース部に残膜が確認されない露光量を感度とした。一方、ネガ型感放射線性樹脂組成物(実施例21~24)については、上記の評価を実施できないため、顕微鏡観察により、パターンの有無のみを確認した。
5インチシリコン基板に、各実施例、比較例で得られた感放射線性樹脂組成物の溶液を、スピンナーを用いて塗布した後、100℃で90秒、ホットプレート上でプリベークして膜厚1.8μmの塗膜を形成した。得られた塗膜を、露光処理を施さずに2.38重量%のテトラメチルアンモニウムヒドロキシド(TMAH)水溶液に、23℃で60秒間、液盛り法により現像した。その後、流水洗浄し、乾燥させた後、230℃で60分間、オーブンで焼成することにより評価サンプルを作成した。
アウトガスの測定にはTDS-MS(昇温脱離質量測定)「WA1000S/W(電子科学製)」を用いて真空度1.0×10-7Paの条件下で、50℃から300℃まで昇温した後、300℃におけるの水(質量数18)および二酸化炭素(質量数44)のアウトガスのピーク強度を測定した。結果を図1~3及び表3に示した。
Claims (11)
- (A)下記一般式(I)で示される繰り返し単位を有するノボラック樹脂、(B)ベンゾオキサジン化合物、カルボジイミド化合物、トリアジンチオール化合物、及び、ビスマレイミド化合物からなる群から選択される少なくとも1種の熱反応性化合物、(C)感放射線化合物、並びに(D)溶剤を含有する感放射線性樹脂組成物。
- ノボラック樹脂(A)は、R4及び/又はR5がメチル基、フェニル基、又は、ヒドロキシフェニル基である繰り返し単位の割合が20~100%である請求項1記載の感放射線性樹脂組成物。
- ノボラック樹脂(A)は、繰り返し単位全体において、R4及びR5のうち少なくとも一部がフェニル基である請求項1又は2記載の感放射線性樹脂組成物。
- 熱反応性化合物(B)は、トリアジンチオール化合物又はビスマレイミド化合物である請求項1~3のいずれか記載の感放射線性樹脂組成物。
- ポジ型放射線リソグラフィー用の請求項1~4のいずれか記載の感放射線性樹脂組成物。
- 感放射線化合物(C)は、ナフトキノンジアジドスルホン酸エステルである請求項1~5のいずれか記載の感放射線性樹脂組成物。
- 有機電界発光素子絶縁膜形成用の請求項5又は6記載の感放射線性樹脂組成物。
- ネガ型放射線リソグラフィー用の請求項1~4のいずれか記載の感放射線性樹脂組成物。
- さらに、(E)界面活性剤及び/又は(F)色素を含有する請求項1~8のいずれか記載の感放射線性樹脂組成物。
- 請求項1~9のいずれか記載の感放射線性樹脂組成物を使用した放射線リソグラフィー構造物。
- 請求項1~9のいずれか記載の感放射線性樹脂組成物を使用した放射線リソグラフィー構造物を有する有機電界発光素子。
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Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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Citations (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS6460630A (en) | 1987-07-21 | 1989-03-07 | Hoechst Celanese Corp | Hydroxypolyimide and high temperature positive type photoresist |
JPH03209478A (ja) | 1989-10-27 | 1991-09-12 | Nissan Chem Ind Ltd | ポジ型感光性ポリイミド樹脂組成物 |
JPH0594013A (ja) | 1991-10-02 | 1993-04-16 | Tokyo Ohka Kogyo Co Ltd | ポジ型ホトレジスト組成物 |
JPH10293398A (ja) * | 1997-03-24 | 1998-11-04 | Agfa Gevaert Ag | 放射線感応性混合物およびそこから製造したオフセット印刷板用の記録材料 |
JP2001075272A (ja) | 1999-09-08 | 2001-03-23 | Tokyo Ohka Kogyo Co Ltd | 液晶素子製造用ポジ型ホトレジスト組成物 |
JP2002169277A (ja) | 2000-12-05 | 2002-06-14 | Jsr Corp | 有機el表示素子の絶縁膜形成用感放射線性樹脂組成物、それから形成された絶縁膜、および有機el表示素子 |
JP2004361638A (ja) * | 2003-06-04 | 2004-12-24 | Tokyo Ohka Kogyo Co Ltd | システムlcd製造用ポジ型ホトレジスト組成物及びレジストパターン形成方法 |
JP2005181976A (ja) * | 2003-11-25 | 2005-07-07 | Tokyo Ohka Kogyo Co Ltd | 化学増幅型ポジ型感光性熱硬化性樹脂組成物、硬化物の形成方法、及び機能素子の製造方法 |
JP2005196130A (ja) | 2003-12-12 | 2005-07-21 | Hitachi Cable Ltd | 感光性ポリイミド樹脂組成物、それを用いた絶縁膜、絶縁膜の製造方法および絶縁膜を使用した電子部品 |
JP2006201653A (ja) | 2005-01-24 | 2006-08-03 | Nippon Zeon Co Ltd | 絶縁膜形成用感放射線性樹脂組成物 |
JP2006323089A (ja) * | 2005-05-18 | 2006-11-30 | Hitachi Chem Co Ltd | 感光性樹脂組成物及びこれを用いた感光性フィルム |
JP2006335671A (ja) | 2005-06-01 | 2006-12-14 | Shikoku Chem Corp | ベンゾオキサジン化合物の製造方法 |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0227487B1 (en) * | 1985-12-27 | 1992-07-15 | Japan Synthetic Rubber Co., Ltd. | Positive type radiation-sensitive resin composition |
JP2792298B2 (ja) * | 1991-12-06 | 1998-09-03 | 東洋インキ製造株式会社 | フォトソルダーレジスト組成物 |
JP4374840B2 (ja) * | 2002-08-30 | 2009-12-02 | 東レ株式会社 | ポジ型感光性樹脂組成物、半導体素子の製造方法および、半導体装置 |
JP2005134743A (ja) * | 2003-10-31 | 2005-05-26 | Nitto Denko Corp | 硬化型フォトレジストとこれを用いる画像形成方法 |
EP1739485B1 (en) * | 2004-04-15 | 2016-08-31 | Mitsubishi Gas Chemical Company, Inc. | Resist composition |
JP4994036B2 (ja) * | 2004-07-15 | 2012-08-08 | 太陽ホールディングス株式会社 | 光硬化性及び熱硬化性樹脂組成物及びその硬化物 |
WO2006059392A1 (ja) * | 2004-12-03 | 2006-06-08 | Tokyo Ohka Kogyo Co., Ltd. | 化学増幅型ホトレジスト組成物、ホトレジスト層積層体、ホトレジスト組成物製造方法、ホトレジストパターンの製造方法及び接続端子の製造方法 |
-
2008
- 2008-03-14 JP JP2008066567A patent/JP4849362B2/ja active Active
-
2009
- 2009-03-05 TW TW098107079A patent/TWI457702B/zh active
- 2009-03-09 US US12/922,241 patent/US20110081613A1/en not_active Abandoned
- 2009-03-09 CN CN2009801087067A patent/CN101971096B/zh active Active
- 2009-03-09 KR KR1020107022710A patent/KR20100133425A/ko not_active Application Discontinuation
- 2009-03-09 WO PCT/JP2009/054421 patent/WO2009113490A1/ja active Application Filing
- 2009-03-09 EP EP09719344.5A patent/EP2270595B1/en not_active Not-in-force
Patent Citations (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS6460630A (en) | 1987-07-21 | 1989-03-07 | Hoechst Celanese Corp | Hydroxypolyimide and high temperature positive type photoresist |
JPH03209478A (ja) | 1989-10-27 | 1991-09-12 | Nissan Chem Ind Ltd | ポジ型感光性ポリイミド樹脂組成物 |
JPH0594013A (ja) | 1991-10-02 | 1993-04-16 | Tokyo Ohka Kogyo Co Ltd | ポジ型ホトレジスト組成物 |
JPH10293398A (ja) * | 1997-03-24 | 1998-11-04 | Agfa Gevaert Ag | 放射線感応性混合物およびそこから製造したオフセット印刷板用の記録材料 |
JP2001075272A (ja) | 1999-09-08 | 2001-03-23 | Tokyo Ohka Kogyo Co Ltd | 液晶素子製造用ポジ型ホトレジスト組成物 |
JP2002169277A (ja) | 2000-12-05 | 2002-06-14 | Jsr Corp | 有機el表示素子の絶縁膜形成用感放射線性樹脂組成物、それから形成された絶縁膜、および有機el表示素子 |
JP2004361638A (ja) * | 2003-06-04 | 2004-12-24 | Tokyo Ohka Kogyo Co Ltd | システムlcd製造用ポジ型ホトレジスト組成物及びレジストパターン形成方法 |
JP2005181976A (ja) * | 2003-11-25 | 2005-07-07 | Tokyo Ohka Kogyo Co Ltd | 化学増幅型ポジ型感光性熱硬化性樹脂組成物、硬化物の形成方法、及び機能素子の製造方法 |
JP2005196130A (ja) | 2003-12-12 | 2005-07-21 | Hitachi Cable Ltd | 感光性ポリイミド樹脂組成物、それを用いた絶縁膜、絶縁膜の製造方法および絶縁膜を使用した電子部品 |
JP2006201653A (ja) | 2005-01-24 | 2006-08-03 | Nippon Zeon Co Ltd | 絶縁膜形成用感放射線性樹脂組成物 |
JP2006323089A (ja) * | 2005-05-18 | 2006-11-30 | Hitachi Chem Co Ltd | 感光性樹脂組成物及びこれを用いた感光性フィルム |
JP2006335671A (ja) | 2005-06-01 | 2006-12-14 | Shikoku Chem Corp | ベンゾオキサジン化合物の製造方法 |
Non-Patent Citations (1)
Title |
---|
See also references of EP2270595A4 |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2011075609A (ja) * | 2009-09-29 | 2011-04-14 | Nippon Zeon Co Ltd | 感放射線性樹脂組成物、及び積層体 |
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EP2270595A4 (en) | 2011-11-02 |
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CN101971096A (zh) | 2011-02-09 |
TWI457702B (zh) | 2014-10-21 |
CN101971096B (zh) | 2012-11-21 |
US20110081613A1 (en) | 2011-04-07 |
KR20100133425A (ko) | 2010-12-21 |
TW200947123A (en) | 2009-11-16 |
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JP2009222923A (ja) | 2009-10-01 |
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