WO2015111607A1 - ネガ型感光性樹脂組成物、それを硬化させてなる硬化膜およびその製造方法ならびにそれを具備する光学デバイスおよび裏面照射型cmosイメージセンサ - Google Patents
ネガ型感光性樹脂組成物、それを硬化させてなる硬化膜およびその製造方法ならびにそれを具備する光学デバイスおよび裏面照射型cmosイメージセンサ Download PDFInfo
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- WO2015111607A1 WO2015111607A1 PCT/JP2015/051490 JP2015051490W WO2015111607A1 WO 2015111607 A1 WO2015111607 A1 WO 2015111607A1 JP 2015051490 W JP2015051490 W JP 2015051490W WO 2015111607 A1 WO2015111607 A1 WO 2015111607A1
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- resin composition
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- 125000003118 aryl group Chemical group 0.000 claims description 18
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- 125000004122 cyclic group Chemical group 0.000 claims description 14
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- 125000002252 acyl group Chemical group 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
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- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 claims description 3
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
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- XQUPVDVFXZDTLT-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C(C=C1)=CC=C1CC1=CC=C(N2C(C=CC2=O)=O)C=C1 XQUPVDVFXZDTLT-UHFFFAOYSA-N 0.000 description 4
- QLTZBYGZXPKHLF-UHFFFAOYSA-N 2-Propylsuccinic acid Chemical compound CCCC(C(O)=O)CC(O)=O QLTZBYGZXPKHLF-UHFFFAOYSA-N 0.000 description 4
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 4
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 4
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- 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
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
- G03F7/031—Organic compounds not covered by group G03F7/029
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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
- G03F7/16—Coating processes; Apparatus therefor
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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
- G03F7/16—Coating processes; Apparatus therefor
- G03F7/168—Finishing the coated layer, e.g. drying, baking, soaking
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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
- G03F7/20—Exposure; Apparatus therefor
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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
- G03F7/20—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
- G03F7/2012—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 using liquid photohardening compositions, e.g. for the production of reliefs such as flexographic plates or stamps
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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
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L27/00—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate
- H01L27/14—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate including semiconductor components sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation
- H01L27/144—Devices controlled by radiation
- H01L27/146—Imager structures
- H01L27/14601—Structural or functional details thereof
- H01L27/14609—Pixel-elements with integrated switching, control, storage or amplification elements
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L27/00—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate
- H01L27/14—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate including semiconductor components sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation
- H01L27/144—Devices controlled by radiation
- H01L27/146—Imager structures
- H01L27/14601—Structural or functional details thereof
- H01L27/1462—Coatings
- H01L27/14621—Colour filter arrangements
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L27/00—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate
- H01L27/14—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate including semiconductor components sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation
- H01L27/144—Devices controlled by radiation
- H01L27/146—Imager structures
- H01L27/14601—Structural or functional details thereof
- H01L27/1464—Back illuminated imager structures
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L27/00—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate
- H01L27/14—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate including semiconductor components sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation
- H01L27/144—Devices controlled by radiation
- H01L27/146—Imager structures
- H01L27/14643—Photodiode arrays; MOS imagers
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L27/00—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate
- H01L27/14—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate including semiconductor components sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation
- H01L27/144—Devices controlled by radiation
- H01L27/146—Imager structures
- H01L27/14683—Processes or apparatus peculiar to the manufacture or treatment of these devices or parts thereof
- H01L27/14685—Process for coatings or optical elements
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- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F21—LIGHTING
- F21Y—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES F21K, F21L, F21S and F21V, RELATING TO THE FORM OR THE KIND OF THE LIGHT SOURCES OR OF THE COLOUR OF THE LIGHT EMITTED
- F21Y2115/00—Light-generating elements of semiconductor light sources
- F21Y2115/10—Light-emitting diodes [LED]
Definitions
- the present invention is exposed to ultraviolet-visible light, which is suitable for a pixel material formed between a condensing microlens formed on a solid-state imaging device or the like that requires high transparency and a high refractive index, and an optical sensor unit.
- the present invention relates to a negative photosensitive resin composition in which a part is dissolved in an alkaline aqueous solution.
- the pixel and the partition wall there are a method of processing an inorganic film formed by a CVD method or the like by dry etching, and a method of applying and processing a resin.
- the former method is currently attracting attention because it is difficult to obtain a refractive index of 1.65 to 2.00 which is optimal for lenses or optical waveguides.
- a photosensitive siloxane composition containing a polysiloxane compound, a quinonediazide compound, a solvent and a thermally crosslinkable compound see, for example, Patent Document 1
- a carboxyl group and / or a phenolic hydroxyl group, and an ethylenically unsaturated group A negative photosensitive resin composition containing a polymer having a double bond group, a radical photopolymerization initiator, and a compound having 3 or more groups containing an unsaturated carboxylic acid ester structure having a hydroxyl group in one molecule (for example, And Patent Document 2) and high refractive index materials containing a siloxane compound having an aromatic hydrocarbon group (for example, see Patent Document 3) have been proposed).
- a positive photosensitive resin composition for example, Patent Document 4
- Patent Document 5 a positive photosensitive resin composition containing a polyamic acid, a compound having a phenolic hydroxyl group, a quinonediazide compound and inorganic particles, a silsesquioxane having a phenol unit and a condensed polycyclic hydrocarbon
- Patent Document 5 A silicone copolymer having a group (see, for example, Patent Document 5) has been proposed.
- it is colored with polyamic acid or phenolic hydroxyl group at the time of curing there is a problem that transparency is lowered.
- Examples of the material having a high refractive index and transparency include coating compositions containing organosilane, siloxane oligomer and metal oxide fine particles and / or sol (see, for example, Patent Document 6), metal oxide particles and alkoxysilane.
- a siloxane-based resin composition (for example, see Patent Document 7) is disclosed. Since these materials are mainly non-photosensitive, patterns are usually processed by a wet etching method using a chemical solution or a dry etching method using plasma.
- a siloxane-based resin composition having a high refractive index and transparency due to positive photosensitivity has been proposed.
- low temperature curing at 200 to 220 ° C. has no solvent resistance for the cured film, and a high curing temperature is essential.
- materials having high refractive index and transparency due to negative photosensitivity include silica-coated titanium oxide particles and compounds having two or more acryloyl groups, photopolymerization initiator compositions (for example, see Patent Document 9) and inorganic oxidation.
- the object of the present invention is to have a high refractive index, high transparency without adding a post-exposure process, high sensitivity in exposure, and excellent resolution and solvent resistance after pattern formation. It is to develop a negative photosensitive resin composition that can obtain a rectangular cross-sectional pattern suitable for pixel formation and barrier rib formation.
- a negative photosensitive resin composition containing the following (a) to (d): (A) metal compound particles (b) polysiloxane compound (c) a compound having one or more groups containing an ⁇ , ⁇ -unsaturated carboxylic acid ester structure (d) a photopolymerization initiator further (e) a compound having a maleimide group It is a negative photosensitive composition characterized by containing.
- the photosensitive composition of the present invention has a high refractive index, high transparency without adding a post-exposure process, has high sensitivity in exposure even after long-term storage at room temperature, and forms a pattern. It is possible to provide a negative photosensitive resin composition that is excellent in later resolution and solvent resistance and that can obtain a rectangular cross-sectional pattern suitable for pixel formation and partition wall formation. Further, according to the present invention, since pattern formation by an etching method is not required, the work process can be simplified, and deterioration of the wiring portion due to chemicals or plasma during etching can be avoided. *
- the negative photosensitive resin composition of the present invention is a negative photosensitive resin composition containing the following (a) to (d), (A) metal compound particles, (B) a polysiloxane compound, (C) a compound having one or more groups containing an ⁇ , ⁇ -unsaturated carboxylic acid ester structure, (D) Photopolymerization initiator Further, (e) A negative photosensitive composition characterized by containing a compound having a maleimide group.
- the (a) metal compound particles used in the negative photosensitive resin composition of the present invention are not particularly limited, but one or more metal compound particles selected from aluminum compound particles, tin compound particles, titanium compound particles and zirconium compound particles or Use of composite particles of at least one metal compound selected from an aluminum compound, a tin compound, a titanium compound, and a zirconium compound and a silicon compound is preferable in that the refractive index is improved and the light condensing rate can be further increased.
- the number average particle diameter of the metal compound particles is preferably 1 nm to 400 nm.
- the number average particle diameter of the metal compound particles is 1 nm or more, the occurrence of cracks during the formation of a thick film can be further suppressed, and from this viewpoint, it is more preferably 5 nm or more.
- the transparency of the cured film with respect to visible light can be further improved by the number average particle diameter of the metal compound particles being 400 nm or less, and from this viewpoint, it is more preferably 70 nm or less.
- the number average particle diameter of the metal compound particles is determined by, for example, a gas adsorption method, a dynamic light scattering method, an X-ray small angle scattering method, a method in which the particle diameter is directly measured by a transmission electron microscope or a scanning electron microscope. In the present invention, it refers to a value measured by a dynamic light scattering method.
- the instrument used for the measurement is not particularly limited, and examples thereof include a dynamic light scattering altimeter DLS-8000 (manufactured by Otsuka Electronics Co., Ltd.).
- metal compound particles examples include “Op-Trake TR-502” and “Op-Trake TR-504” of tin oxide-titanium oxide composite particles, and “Op-trake TR-503” of silicon oxide-titanium oxide composite particles.
- the polysiloxane compound (b) used in the present invention is not particularly limited as long as the main skeleton is a siloxane, that is, a polymer having a Si—O bond, but the alkali solubility is improved and the developer solubility of the non-patterned portion is improved. From the point of making it easier to form a pattern (hereinafter, forming a pattern by dissolving a non-pattern part in a developing solution may be referred to as patterning) by improving, and maintaining a higher sensitivity in exposure,
- the main skeleton preferably contains a structural unit represented by the general formula (1) and / or (2).
- R 1 is an organic group having a carboxyl group and / or dicarboxylic anhydride structure
- R 2 is hydrogen, an alkyl group having 1 to 6 carbon atoms, an acyl group having 2 to 6 carbon atoms, or an allyl group having 6 to 16 carbon atoms.
- R 1 includes 3-succinic anhydride propyl group, 3-succinic anhydride propyl group, propionic acid group, 3-maleic acid propyl group, 3-phthalic acid propyl group, 3-naphthalic acid propyl group, 3 -(P-benzoic acid) propyl group, 3- (m-benzoic acid) propyl group, 3- (o-benzoic acid) propyl group, and the like.
- R 2 represents hydrogen, an alkyl group having 1 to 6 carbon atoms, an acyl group having 2 to 6 carbon atoms or an aryl group having 6 to 16 carbon atoms, and examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, n -Butyl group and the like, acyl group includes acetyl group, propionyl group, acryloyl group and the like, and aryl group includes phenyl group, naphthyl group and the like.
- R 1 of the compound of the general formula (1) and / or (2) is preferably an organic group having a dicarboxylic acid anhydride represented by any of the following general formulas (11) to (13).
- R 15 , R 16 and R 17 are a single bond, a chain aliphatic hydrocarbon group having 1 to 10 carbon atoms, or a cyclic aliphatic group having 3 to 16 carbon atoms. Represents a hydrocarbon group, an alkylcarbonyloxy group having 2 to 6 carbon atoms, a carbonyl group, an ether group, an ester group, an amide group, an aromatic group having 6 to 16 carbon atoms, or a divalent group having any of these.
- the hydrogen atoms of these groups are alkyl groups having 1 to 10 carbon atoms, alkenyl groups having 2 to 10 carbon atoms, aryl groups having 6 to 16 carbon atoms, alkylcarbonyloxy groups having 2 to 6 carbon atoms, hydroxy groups, amino groups And may be substituted with a group, a carboxyl group or a thiol group, r, s, t and u represent an integer of 0 to 3.)
- a single bond means that R 15 , R 16 or R 17 does not exist as a bonding group, and a Si atom is directly bonded to a position where R 15 , R 16 or R 17 can be bonded. Indicates.
- the ratio of the number of moles of Si atoms in the structural unit represented by the general formula (1) and / or (2) is 5 mol% or more, patterning can be more reliably performed with an alkaline developer during development, and 30 mol%. From the point that the heat and humidity resistance is further improved when it is a cured film, the general formula (1) and / or (2) constituting the polysiloxane compound with respect to the number of moles of Si atoms of the polysiloxane compound is as follows.
- the ratio of the number of moles of Si atoms in the structural unit shown is preferably 5 mol% or more and 30 mol% or less.
- R 3 is an organic group
- R 4 is hydrogen, an alkyl group having 1 to 6 carbon atoms, an acyl group having 2 to 6 carbon atoms, an alkenyl group having 2 to 10 carbon atoms having an alkenyl group having 2 to 10 carbon atoms Represents an organic group or an aryl group having 6 to 16 carbon atoms.
- R 4 a group selected from the groups described as R 2 in the above general formula (1) can be used.
- R 2 in the general formula (1) and R 4 in the general formula (3) may be the same group or different groups.
- R 3 is a vinyl group, an allyl group, a styryl group, a ⁇ -acryloylpropyl group, a methacryloyl group, an acryloyl group (a methacryloyl group and an acryloyl group may be collectively referred to as “(meth) acryloyl group”). And acryloylpropylmethyl, glycidoxy group, and the like. Two or more of these may be used in combination. Among these, an allyl group, a vinyl group, a (meth) acryloyl group, or a styryl group is preferable in terms of high reactivity, higher sensitivity, and increased crosslinking density.
- silane monomers represented by the following general formula (14) and / or (15) are used.
- Examples include structural units obtained by polycondensation.
- R 18 represents any one of an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, and an aryl group having 6 to 15 carbon atoms. R 18 may be the same or different from each other.
- “plural R 18 ” indicates a case where n is 2 or 3.
- These alkyl groups and aryl groups may be either unsubstituted or substituted, and can be selected according to the characteristics of the composition.
- alkyl group and its substituent include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, t-butyl group, n-hexyl group, n-decyl group, trifluoromethyl group 3,3,3-trifluoropropyl group, 3-glycidoxypropyl group, 2- (3,4-epoxycyclohexyl) ethyl group, [(3-ethyl-3-oxetanyl) methoxy] propyl group, 3- Aminopropyl group, 3-mercaptopropyl group, 3-isocyanatopropyl group, 1- (p-hydroxyphenyl) ethyl group, 2- (p-hydroxyphenyl) ethyl group, 4-hydroxy-5- (p-hydroxyphenylcarbonyl) And oxy) pentyl group.
- aryl group and substituted products thereof include phenyl group
- R 19 in the general formula (14) represents any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, an acyl group having 2 to 6 carbon atoms, and an aryl group having 6 to 15 carbon atoms, and a plurality of R 19 are the same But it can be different.
- “plural R 19 ” indicates a case where 4-n is 2 to 4.
- These alkyl groups, acyl groups and aryl groups may be either unsubstituted or substituted, and can be selected according to the characteristics of the composition.
- Specific examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, and an n-butyl group.
- Specific examples of the acyl group include an acetyl group.
- Specific examples of the aryl group include a phenyl group.
- N in the general formula (14) represents an integer of 0 to 3.
- organosilane represented by the general formula (14) include tetrafunctional silanes such as tetramethoxysilane, tetraethoxysilane, tetraacetoxysilane, and tetraphenoxysilane, methyltrimethoxysilane, methyltriethoxysilane, and methyl.
- R 20 to R 23 are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, an acyl group having 2 to 6 carbon atoms, or 6 to 15 carbon atoms.
- Specific examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, and an n-butyl group.
- Specific examples of the acyl group include an acetyl group.
- Specific examples of the aryl group include a phenyl group.
- v is an integer of 2 to 8, and v may have a distribution.
- organosilane represented by the general formula (15) By using the organosilane represented by the general formula (15), a positive photosensitive composition excellent in sensitivity and resolution can be obtained while maintaining high heat resistance and transparency.
- Specific examples of the organosilane represented by the general formula (15) include methyl silicate 51 (manufactured by Fuso Chemical Industry Co., Ltd.), M silicate 51, silicate 40, silicate 45 (manufactured by Tama Chemical Industry Co., Ltd.), and methyl silicate 51. , Methyl silicate 53A, ethyl silicate 40, ethyl silicate 48 (manufactured by Colcoat Co., Ltd.), and the like.
- the metal compound particles are 10 parts by weight or more with respect to 100 parts by weight of the (b) polysiloxane compound, the refractive index becomes higher when the cured film is formed, and the light condensing efficiency is further improved. Since the formation of an air layer when forming a cured film can be further suppressed when the amount is less than or equal to parts, and a decrease in refractive index can be further suppressed, (a) metal compound particles are added to (b) 100 parts by weight of a polysiloxane compound. On the other hand, it is preferably 10 parts by weight or more and 500 parts by weight or less.
- the negative photosensitive composition of the present invention contains (c) a compound having at least one group containing an ⁇ , ⁇ -unsaturated carboxylic acid ester structure.
- Compounds having one group containing an ⁇ , ⁇ -unsaturated carboxylic acid ester structure include ethoxylated o-phenylphenol acrylate, methoxypolyethylene glycol # 400 acrylate, methoxypolyethylene glycol # 550 acrylate, phenoxypolyethylene glycol acrylate, 2 -Acryloyloxyethyl succinate, isostearyl acrylate, 2-methacryloyloxyethyl phthalate, methoxypolyethylene glycol # 400 methacrylate, methoxypolyethylene glycol # 1000 methacrylate, phenoxyethylene glycol methacrylate, stearyl methacrylate, 2-methacryloyloxyethyl succinate , Isoamyl acrylate, lauryl acrylate, stearyl acrylate , Ethoxy-diethylene glycol acrylate, methoxy-triethylene glycol acrylate, 2-ethylhexyl-
- phenol ethylene oxide modified acrylate hereinafter “ethylene oxide modified” may be abbreviated as “EO modified”), o-phenylphenol EO modified acrylate, paracumylphenol EO modified acrylate, nonylphenol propylene oxide modified acrylate (hereinafter “propylene”).
- EO modified ethylene oxide modified
- propylene nonylphenol propylene oxide modified acrylate
- PO-modified nonylphenol EO-modified acrylate
- 2-ethylhexyl EO-modified acrylate 2-ethylhexyl EO-modified acrylate
- Compounds having two alkenyl groups include ethylene glycol dimethyl ether dimethacrylate, diethylene glycol dimethacrylate, triethylene glycol dimethacrylate, polyethylene glycol dimethacrylate, ethoxylated bisphenol A dimethacrylate, 1,10-decanediol dimethacrylate, 1,6- Hexanediol dimethacrylate, 1,9-nonanediol dimethacrylate, neopentyl glycol dimethacrylate, glycerin dimethacrylate, 2-hydroxy-3-acryloyloxypropyl methacrylate, polyethylene glycol diacrylate, propoxylated ethoxylated bisphenol A diacrylate, ethoxy Bisphenol A diacrylate, propoxylated bisphenol A diacrylate, 1,10-decanediol diacrylate, 1,6-hexanediol diacrylate, 1,9-nonanediol diacrylate,
- the compound (c) having at least one group containing an ⁇ , ⁇ -unsaturated carboxylic acid ester structure is not particularly limited, but has a rigid organic group in the skeleton and is superior in resolution from the following general formula. It is preferably 1 or more selected from (5) to (10).
- R 5 represents a single bond, a chain aliphatic group having 1 to 10 carbon atoms and 1 to 3 oxygen atoms, or a cyclic aliphatic hydrocarbon group having 3 to 16 carbon atoms.
- the single bond, R 5 is not present as a bonding group, R 5 is, at a position capable of binding, (The same applies to the subsequent) indicating that the O atom is directly bonded.
- Examples of the compound represented by the general formula (5) include dimethylol tricyclodecane acrylate, dimethylol tricyclodecane diacrylate, and tricyclodecane dimethanol dimethacrylate.
- R 7 represents a single bond, a chain aliphatic group having 1 to 10 carbon atoms and 1 to 3 oxygen atoms, or a cyclic aliphatic hydrocarbon group having 3 to 16 carbon atoms.
- good .R 8 be the same or different and each is 7 represents hydrogen or a methyl group, the plurality of R 8 may .k be in the same or different and each represents an integer of 1-2.
- Examples of the compound represented by the general formula (6) include 1-naphthyl acrylate, 1-naphthyl methacrylate, 2-naphthyl acrylate, 2-naphthyl methacrylate, 1,4-naphthyl diacrylate, 9,9-bis [4- (2 -Acryloyloxyethoxy) phenyl] fluorene, 1,4-ethylene oxide dimethacrylate naphthalene.
- R 9 represents a single bond, a chain aliphatic group having 1 to 10 carbon atoms and 1 to 3 oxygen atoms, or a cyclic aliphatic hydrocarbon group having 3 to 16 carbon atoms.
- 9 may be the same or different
- R 10 represents hydrogen or a methyl group
- a plurality of R 10 may be the same or different
- R 11 is hydrogen or 1 to 10 carbon atoms and 1 to 3 oxygen atoms
- Examples of the compound represented by the compound (7) include 9,9-bis [4- (2-acryloyloxyethoxy) phenyl] fluorene, 9,9-bis [4- (2-methacryloyloxyethoxy) phenyl] fluor
- R 12 represents a single bond, a chain aliphatic group having 1 to 10 carbon atoms and 1 to 3 oxygen atoms, or a cyclic aliphatic hydrocarbon group having 3 to 16 carbon atoms. 12 may be the same or different, and o represents an integer of 1 to 2.
- Examples of the compound represented by the general formula (8) include norbornene monoacrylate, norbornene diacrylate, norbornene ethylene oxide acrylate, and norbornene oxide diacrylate.
- R 13 represents a single bond, a chain aliphatic group having 1 to 10 carbon atoms and 1 to 3 oxygen atoms, or a cyclic aliphatic hydrocarbon group having 3 to 16 carbon atoms. 13 may be the same or different, and p represents an integer of 1 to 2.
- Examples of the compound represented by the general formula (9) include adamantane monoacrylate, adamantane diacrylate, adamantane ethylene oxide acrylate, and adamantane ethylene oxide diacrylate.
- q represents an integer of 0 to 3
- R 14 represents a chain aliphatic having 1 to 10 carbon atoms and 1 to 3 oxygen atoms
- Examples of the compound represented by the general formula (10) include N-acryloyloxyethyl hexahydrophthalimide.
- the negative photosensitive siloxane composition of the present invention contains (d) a photopolymerization initiator.
- the photopolymerization initiator refers to a compound that decomposes and / or reacts with light (including ultraviolet rays and electron beams) to generate radicals.
- photopolymerization initiator examples include 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropan-1-one, 2-dimethylamino-2- (4-methylbenzyl) -1- ( 4-morpholin-4-yl-phenyl) -butan-1-one, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butanone-1,2,4,6-trimethylbenzoylphenylphosphine oxide Bis (2,4,6-trimethylbenzoyl) -phenylphosphine oxide, bis (2,6-dimethoxybenzoyl)-(2,4,4-trimethylpentyl) -phosphine oxide, 1-phenyl-1,2-propane Dione-2- (o-ethoxycarbonyl) oxime, 1,2-octanedione, 1- [4- (phenylthio) -2- (o Benzoyloxime)], 1-phenyl-1
- ⁇ -aminoalkylphenone compounds In order to further increase the hardness of the cured film, ⁇ -aminoalkylphenone compounds, acylphosphine oxide compounds, oxime ester compounds, benzophenone compounds having amino groups, or benzoic acid ester compounds having amino groups are preferred.
- Examples of the ⁇ -aminoalkylphenone compound include 2-methyl- [4- (methylthio) phenyl] -2-morpholinopropan-1-one, 2-dimethylamino-2- (4-methylbenzyl) -1- ( 4-morpholin-4-yl-phenyl) -butan-1-one or 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butanone-1.
- acylphosphine oxide compound examples include 2,4,6-trimethylbenzoylphenylphosphine oxide, bis (2,4,6-trimethylbenzoyl) -phenylphosphine oxide, or bis (2,6-dimethoxybenzoyl)-(2, 4,4-Trimethylpentyl) -phosphine oxide.
- Examples of the oxime ester compound include 1-phenyl-1,2-propanedione-2- (o-ethoxycarbonyl) oxime, 1,2-octanedione, 1- [4- (phenylthio) -2- (o -Benzoyloxime)], 1-phenyl-1,2-butadion-2- (o-methoxycarbonyl) oxime, 1,3-diphenylpropanetrione-2- (o-ethoxycarbonyl) oxime or ethanone, 1- [9 -Ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl]-, 1- (0-acetyloxime).
- benzophenone compound having an amino group examples include 4,4-bis (dimethylamino) benzophenone and 4,4-bis (diethylamino) benzophenone.
- benzoic acid ester compound having an amino group examples include ethyl p-dimethylaminobenzoate, 2-ethylhexyl-p-dimethylaminobenzoate, and ethyl p-diethylaminobenzoate.
- the negative photosensitive resin composition of the present invention contains (e) a compound having a maleimide group.
- a maleimide compound is a compound having a maleimide group and is known to cause not only radical reaction but also photodimerization reaction that does not suffer from oxygen damage at the time of exposure prior to patterning. Since the reaction proceeds, the surface that has been difficult to react only by the conventional radical reaction easily undergoes a photoreaction. Furthermore, since the surface becomes more difficult to dissolve in the alkaline aqueous solution due to its high hydrophobicity, the cross-sectional shape of the pattern tends to be more rectangular.
- maleimide compounds N-phenylmaleimide (Nippon Shokubai "Imirex-P" (registered trademark)), N- (4-aminophenyl) maleimide, N- [4- (2-benzimidazolyl) phenyl] maleimide 1,4-bis (maleimido) butane, 1,2-bis (maleimido) ethane, 4,4′-bismaleimide diphenylmethane, 1,2-bis (maleimido) ethane, 1,6-bis (maleimido) hexane, Nt-butylmaleimide, N-dichloromaleimide, N-ethylmaleimide, fluorescein-5-maleimide, 4-maleimidobutanoic acid, 6-maleimidohexanoic acid, 3-maleimidopropionic acid, N-methoxycarbonylmaleimide, phenylmethane Maleimide, m-phenylene bismaleimide
- a compound having two or more maleimide groups is more preferable.
- the content includes (a) metal compound particles, (b) a polysiloxane compound, and (c) an ⁇ , ⁇ -unsaturated carboxylic acid ester structure from the viewpoint that chemical resistance is further improved by the photocuring reaction.
- the molecular weight of the maleimide compound is preferably 2000 or less, more preferably 800 or less, from the viewpoint that (b) the compatibility with the polysiloxane compound is good and the photoreaction occurs during photocuring.
- the negative photosensitive resin composition of the present invention preferably contains (f) a solvent.
- the solvent is not particularly limited, but it is preferable to use a compound having an alcoholic hydroxyl group as the solvent (hereinafter, the solvent when a compound having an alcoholic hydroxyl group is used as the solvent is abbreviated as “solvent having an alcoholic hydroxyl group”. To do).
- solvent having an alcoholic hydroxyl group the solvent when a compound having an alcoholic hydroxyl group is used as the solvent is abbreviated as “solvent having an alcoholic hydroxyl group”. To do).
- solvent having an alcoholic hydroxyl group the stability of the polysiloxane compound (b) can be improved, and the transparency of the coating film obtained from the negative photosensitive resin composition can be further improved.
- the solvent having an alcoholic hydroxyl group is not particularly limited, but a compound having a boiling point of 110 to 250 ° C. under atmospheric pressure is preferable (hereinafter, “boiling point under atmospheric pressure” is abbreviated as “boiling point”).
- boiling point a compound having a boiling point of 110 to 250 ° C. under atmospheric pressure
- drying during the formation of the coating film proceeds moderately, and a coating film with a good surface appearance can be easily obtained.
- the boiling point is 250 ° C. or lower, the solvent can be easily removed.
- solvent having an alcoholic hydroxyl group examples include acetol (boiling point: 147 ° C.), 3-hydroxy-3-methyl-2-butanone (boiling point: 140 ° C.), 4-hydroxy-3-methyl-2-butanone ( Boiling point: 73 ° C), 5-hydroxy-2-pentanone (boiling point: 144 ° C), 4-hydroxy-4-methyl-2-pentanone (diacetone alcohol) (boiling point: 166 ° C), ethyl lactate (boiling point: 151 ° C) ), Butyl lactate (boiling point: 186 ° C.), propylene glycol monomethyl ether (boiling point: 118 ° C.), propylene glycol monoethyl ether (boiling point: 132 ° C.), propylene glycol mono n-propyl ether (boiling point: about 150 ° C.), propylene Glycol mono
- solvents may be contained together with the solvent having an alcoholic hydroxyl group or in place of the solvent.
- Other solvents include ethyl acetate, n-propyl acetate, isopropyl acetate, n-butyl acetate, isobutyl acetate, propylene glycol monomethyl ether acetate, 3-methoxy-1-butyl acetate, 3-methyl-3-methoxy-1- Esters such as butyl acetate and ethyl acetoacetate, ketones such as methyl isobutyl ketone, diisopropyl ketone, diisobutyl ketone and acetylacetone, ethers such as diethyl ether, diisopropyl ether, di-n-butyl ether, diphenyl ether, diethylene glycol ethyl methyl ether and diethylene glycol dimethyl ether ⁇ -butyrolactone, ⁇ -valerolactone,
- the negative photosensitive resin composition of the present invention contains (f) a solvent
- the content of (f) the solvent is not particularly limited, but the total of (a) metal compound particles and (b) polysiloxane compound.
- the amount is preferably in the range of 100 to 2,000 parts by weight with respect to the amount.
- the negative photosensitive resin composition of the present invention may contain various surfactants such as various fluorine-based surfactants and silicone-based surfactants in order to improve the flowability during coating.
- various surfactants such as various fluorine-based surfactants and silicone-based surfactants in order to improve the flowability during coating.
- type of surfactant for example, “Megafac (registered trademark)” F142D, F172, F173, F183, F445, F470, F475, F477 (above, Dainippon Ink Chemicals, Inc.) Kogyo Co., Ltd.), NBX-15, FTX-218, DFX-18 (manufactured by Neos Co., Ltd.) and other fluorosurfactants, BYK-333, BYK-301, BYK-331, BYK-345, BYK Silicone surfactants such as ⁇ 307 (manufactured by BYK Japan), polyalkylene oxide surfactants, poly (meth)
- the negative photosensitive resin composition of the present invention includes a silane coupling agent, a crosslinking agent, a crosslinking accelerator, a sensitizer, a thermal radical generator, a dissolution accelerator, a dissolution inhibitor, and a stabilizer as necessary. Further, additives such as an antifoaming agent can be contained.
- the cured film of the present invention is obtained by curing the negative photosensitive resin composition of the present invention. Moreover, the cured film of this invention can be obtained with the manufacturing method which apply
- the negative photosensitive resin composition of the present invention is coated on a substrate by a known method such as spin coating or slit coating, and heated (prebaked) using a heating device such as a hot plate or oven, and the solvent in the composition Evaporate.
- the prebaking is preferably performed at a temperature range of 50 to 150 ° C. for 30 seconds to 30 minutes.
- the film thickness after pre-baking is preferably 0.1 to 15 ⁇ m.
- UV-visible exposure machine such as a stepper, mirror projection mask aligner (MPA), parallel light mask aligner (PLA), etc.
- MPA mirror projection mask aligner
- PLA parallel light mask aligner
- the exposed area is crosslinked to reduce the solubility in the developer or to make it insoluble.
- the unexposed part is dissolved and removed by development to obtain a negative pattern.
- the resolution of the pattern is preferably 8 ⁇ m or less.
- a developing method it is preferable to immerse in a developing solution for 5 seconds to 10 minutes by a method such as shower, dipping or paddle.
- a known alkali developer can be used.
- an alkali alkali such as an alkali metal hydroxide, carbonate, phosphate, silicate, borate, 2-diethylaminoethanol, mono Examples include amines such as ethanolamine and diethanolamine, and aqueous solutions of quaternary ammonium salts such as tetramethylammonium hydroxide (TMAH) and choline. Two or more of these may be used.
- TMAH tetramethylammonium hydroxide
- two or more of these may be used.
- dehydration drying baking may be performed in a temperature range of 50 to 150 ° C. with a heating device such as a hot plate or
- the film developed in this manner is heated (soft bake) for 30 seconds to 30 minutes in a temperature range of 50 to 250 ° C. with a heating device such as a hot plate or oven as necessary, and then the hot plate or oven or the like.
- a cured film is obtained by heating (curing) in a temperature range of 150 to 450 ° C. for about 30 seconds to 2 hours.
- Negative photosensitive resin composition of the present invention from the viewpoint of productivity in the pattern formation, it is preferable that the sensitivity at the time of exposure is 1500 J / m 2 or less, more preferably 1000 J / m 2 or less.
- Such high sensitivity can be more easily obtained by using a negative photosensitive resin composition containing a polysiloxane compound using an organosilane having a carboxyl group and / or a dicarboxylic anhydride structure.
- the sensitivity at the time of exposure is obtained by the following method.
- a negative photosensitive resin composition is spin-coated on a silicon wafer at an arbitrary rotation number using a spin coater, and prebaked at 120 ° C. for 3 minutes using a hot plate to prepare a prebaked film having a thickness of 1 ⁇ m.
- PLA PLA-501F manufactured by Canon Inc.
- the pre-baked film is exposed through a gray scale mask having a line and space pattern of 1 to 10 ⁇ m for sensitivity measurement with an ultra-high pressure mercury lamp, and then automatically developed.
- a square pattern having a design dimension of 100 ⁇ m is not peeled off after development, and an exposure amount formed on the substrate (hereinafter referred to as an optimum exposure amount) is defined as a photosensitive sensitivity.
- thermosetting process a cured film is prepared by curing at 220 ° C. for 5 minutes using a hot plate, and the minimum pattern dimension in the photosensitive sensitivity is obtained as the post-curing resolution.
- the cured film obtained by curing the negative photosensitive resin composition of the present invention preferably has a light transmittance of 90% or more per film thickness of 1 ⁇ m at a wavelength of 400 nm, more preferably 92% or more.
- “transmittance” is used as an index of transparency.
- Such a high transmittance can be easily obtained by, for example, a negative photosensitive resin composition using a highly transparent polysiloxane compound as a resin component.
- “light transmittance per 1 ⁇ m of film thickness” means that when the measured value of the film thickness at the time of measurement is 1 ⁇ m, the light transmittance at that film thickness is the actual measured value of the film thickness at the time of measurement. When the value is not 1 ⁇ m, it means the light transmittance converted when the film thickness is 1 ⁇ m.
- the transmittance per 1 ⁇ m of film thickness at a wavelength of 400 nm of the cured film is determined by the following method.
- the negative photosensitive resin composition is spin-coated on a Tempax glass plate at an arbitrary rotation number using a spin coater, and prebaked at 100 ° C. for 3 minutes using a hot plate.
- a cured film having a thickness of 1 ⁇ m is prepared by heat curing at 220 ° C. for 5 minutes in the air using a hot plate.
- the ultraviolet-visible absorption spectrum of the obtained cured film is measured using MultiSpec-1500 manufactured by Shimadzu Corporation, and the transmittance at a wavelength of 400 nm is determined.
- the extinction coefficient k and the film thickness t of each target cured film by each wavelength ⁇ are measured with a spectroscopic ellipsometer FE5000 manufactured by Otsuka Electronics Co., Ltd., and can be obtained by the following formula.
- Transmittance exp ( ⁇ 4 ⁇ kt / ⁇ )
- the film thickness of the produced cured film deviates from 1 ⁇ m, it can be calculated by the following formula.
- k represents an extinction coefficient
- t represents a film thickness
- ⁇ represents a measurement wavelength.
- the negative photosensitive resin composition and the cured film of the present invention are preferably used for optical devices such as an image sensor (solid-state imaging device), an optical filter, a display, and LED illumination.
- LED illumination is particularly preferable.
- the LED illumination is illumination using a light emitting diode (Light Emitting Diode).
- a light-emitting diode is a type of EL (Electro Luminescence) element that converts electrical energy into light energy using the characteristics of a compound semiconductor, and a device using a Group 3-5 compound semiconductor has been put into practical use.
- the Group 3-5 compound semiconductor is a direct transition type semiconductor, and can operate stably at a higher temperature than an element using another semiconductor.
- Group 3-5 compound semiconductors are widely used in various lighting devices, illuminations, electronic devices and the like because of their high energy conversion efficiency and long lifetime.
- LED lighting with less power consumption can be achieved. realizable.
- optical device comprising the cured film of the present invention
- an image sensor More specifically, a condensing microlens or an optical waveguide formed on a solid-state imaging device such as an image sensor, an antireflection film installed as an optical filter, and the like can be given.
- a condensing microlens or an optical waveguide formed on a solid-state imaging device such as an image sensor, an antireflection film installed as an optical filter, and the like
- it is particularly suitably used as a condensing microlens formed on a solid-state image sensor, or an optical waveguide connecting the condensing microlens and the optical sensor unit.
- the image sensor having the cured film of the present invention is a back-illuminated CMOS image sensor having at least a photoelectric conversion layer, a color filter, and a planarization layer in order, and the color filter is a negative photosensitive film of the present invention.
- the colored pixel is divided by the pattern obtained from the conductive resin composition, and the refractive index of the planarizing layer is preferably smaller than the refractive index of the pattern. Since the negative composition of the present invention can form a shape with a high taper angle, it can be used as a transparent partition material for colored pixels of an image sensor, and the colored pixels are divided and further flat at a lower refractive index on the upper side. This is because the formation efficiency can improve the light collection efficiency due to the difference in refractive index and the high transparent partition.
- the optical device including the cured film of the present invention include a flattening material for a TFT substrate for display, a color filter such as a liquid crystal display, a protective film thereof, a phase shifter, and the like. Further, it can be used as a buffer coat, an interlayer insulating film, and various protective films of a semiconductor device. Since the negative photosensitive resin composition of the present invention does not require pattern formation by an etching method, the operation can be simplified, and deterioration of the wiring portion due to an etching chemical or plasma can be avoided.
- the flask was immersed in a 40 ° C. oil bath and stirred for 60 minutes, and then the oil bath was heated to 115 ° C. over 30 minutes. One hour after the start of temperature increase, the internal temperature of the solution reached 100 ° C., and then heated and stirred for 2 hours (the internal temperature was 100 to 110 ° C.).
- a solution of a polysiloxane compound was obtained. The resulting solution was diluted with DAA so that the solid content concentration was 35% by weight.
- PS-01 metal compound particles and (b) polysiloxane compounds contained in the solution obtained in Preparation Example 1 are collectively referred to as “PS-01”. That is, the parts by weight of PS-01 are the total number of (a) metal compound particles and (b) polysiloxane compound contained in the solution, and do not include solvents or other components (hereinafter referred to as PS-02 to PS-02). The same applies to PS-09).
- Phosphoric acid aqueous solution prepared by dissolving phosphoric acid 0.157g was added over 10 minutes .4G. Thereafter, the mixture was heated and stirred in the same manner as in Preparation Example 1 to obtain a solution of (b) polysiloxane compound in which titanium oxide particles were dispersed as (a) metal compound particles. The resulting solution was diluted with DAA so that the solid content concentration was 35% by weight.
- (a) metal compound particles and (b) polysiloxane compounds contained in the solution obtained in Preparation Example 2 are collectively referred to as “PS-02”.
- Phosphoric acid aqueous solution prepared by dissolving the g was added over 10 minutes. Thereafter, the mixture was heated and stirred in the same manner as in Preparation Example 1 to obtain a solution of (a) a polysiloxane compound in which titanium oxide-silicon oxide composite particles were dispersed as metal compound particles. The resulting solution was diluted with DAA so that the solid content concentration was 35% by weight.
- (a) metal compound particles and (b) polysiloxane compounds contained in the solution obtained in Preparation Example 3 are collectively referred to as “PS-03”.
- the number average particle size is 20 nm. 149.86 g (with a particle content of 150 parts by weight with respect to 100 parts by weight of the organosilane fully condensed (20.6 g)), 75.89 g of DAA were charged, and water 5.
- the resulting solution was diluted with DAA so that the solid content concentration was 35% by weight.
- PS-06 polysiloxane compounds contained in the solution obtained in Preparation Example 6 are collectively referred to as “PS-06”.
- Preparation Example 8 (a) Preparation of (b) polysiloxane compound solution in which metal compound particles are dispersed 5.45 g (0.04 mol) of methyltrimethoxysilane, 3-trimethoxysilylpropyl in a 500 ml three-necked flask “OPTRAIQUE” which is a methanol dispersion of 5.25 g (0.02 mol) of succinic acid, 9.93 g (0.04 mol) of 1-naphthyltrimethoxysilane and 20.6 wt% titanium oxide-silicon oxide composite particles.
- OPTRAIQUE is a methanol dispersion of 5.25 g (0.02 mol) of succinic acid, 9.93 g (0.04 mol) of 1-naphthyltrimethoxysilane and 20.6 wt% titanium oxide-silicon oxide composite particles.
- Phosphoric acid aqueous solution prepared by dissolving phosphoric acid 0.157g was added over 10 minutes. Thereafter, the mixture was heated and stirred in the same manner as in Preparation Example 1 to obtain a solution of (b) polysiloxane compound in which titanium oxide particles were dispersed as (a) metal compound particles. The resulting solution was diluted with DAA so that the solid content concentration was 35% by weight.
- (a) metal compound particles and (b) polysiloxane compounds contained in the solution obtained in Preparation Example 10 are collectively referred to as “PS-09”.
- Residual film ratio (%) film thickness of exposed film after development / film thickness of pre-baked film ⁇ 100 (3) Calculation of Photosensitivity Using the obtained pre-baked film with PLA (PLA-501F manufactured by Canon Inc.), a gray scale mask for sensitivity measurement using an ultra-high pressure mercury lamp (Multi-Density Resolution Mask manufactured by Opto-Line) The pattern was exposed through. A square pattern having a design dimension of 100 ⁇ m was not peeled off after development, and the minimum exposure amount that was formed was defined as the photosensitive sensitivity.
- Example 1 After preparing the composition 1 ratio shown in Table 1 and adding 30 ppm of DFX-18 (manufactured by Neos Co., Ltd.) as a fluorosurfactant, mixing and stirring under a yellow light to obtain a uniform solution
- the composition 1 was prepared by filtration through a 0.20 ⁇ m filter.
- composition 1 spin coating was performed on an 8-inch silicon wafer using a spin coater (1H-360S manufactured by Mikasa Co., Ltd.), and then using a hot plate (SCW-636 manufactured by Dainippon Screen Mfg. Co., Ltd.). A pre-baked film having a thickness of 1.0 ⁇ m was produced by heating at 100 ° C. for 3 minutes. Using the obtained pre-baked film, (1) film thickness measurement and (3) photosensitivity calculation were performed.
- the obtained pre-baked film was exposed at intervals of 50 msec from 100 msec to 1000 msec using an i-line stepper (i9C manufactured by Nikon Corporation). After the exposure, the film was developed by showering with a 2.38 wt% TMAH aqueous solution for 90 seconds using an automatic developing apparatus (AD-2000 manufactured by Takizawa Sangyo Co., Ltd.) and then rinsing with water for 30 seconds. Got. Then, the cured film 1 was produced by curing at 220 ° C. for 5 minutes using a hot plate. The obtained post-development film 1 and cured film 1 were used to evaluate (4) resolution and (8) taper angle.
- the obtained pre-baked film was exposed to 1500 J / m 2 with an ultra-high pressure mercury lamp using PLA (PLA-501F manufactured by Canon Inc.). After the exposure, using an automatic developing apparatus (AD-2000 manufactured by Takizawa Sangyo Co., Ltd.), the shower development is performed with a 2.38 wt% TMAH aqueous solution for 90 seconds, followed by rinsing with water for 30 seconds. Got. Then, the cured film 2 was produced by curing at 220 ° C. for 5 minutes using a hot plate.
- AD-2000 automatic developing apparatus manufactured by Takizawa Sangyo Co., Ltd.
- Examples 2 to 14 Comparative Examples 1 to 21
- Compositions 2 to 35 were prepared in the same manner as in Example 1 except that the components of the composition were changed as shown in Tables 1 to 6.
- a prebaked film, a post-development film, and a cured film were prepared and evaluated in the same manner as in Example 1. The evaluation results are shown in Tables 7-9.
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Abstract
Description
以下の(a)~(d)を含有するネガ型感光性樹脂組成物であって、
(a)金属化合物粒子
(b)ポリシロキサン化合物
(c)α,β-不飽和カルボン酸エステル構造を含む基を1つ以上有する化合物
(d)光重合開始剤
さらに(e)マレイミド基を有する化合物を含有することを特徴とするネガ型感光性組成物である。
(a)金属化合物粒子、
(b)ポリシロキサン化合物、
(c)α,β-不飽和カルボン酸エステル構造を含む基を1つ以上有する化合物、
(d)光重合開始剤
さらに(e)マレイミド基を有する化合物を含有することを特徴とするネガ型感光性組成物である。
R1としては、3-コハク酸無水物プロピル基、3-コハク酸無水物プロピル基、プロピオン酸基、3-マレイン酸プロピル基、3-フタル酸プロピル基、3-無水ナフタル酸プロピル基、3-(p-安息香酸)プロピル基、3-(m-安息香酸)プロピル基、3-(o-安息香酸)プロピル基、などが挙げられる。
なお、単結合とは、R15、R16またはR17が、結合基としては存在せず、R15、R16またはR17が、結合しうる位置に、Si原子が直接結合していることを示す。
R4としては、前述の一般式(1)におけるR2とに記載した基から選ばれる基を用いることができる。このとき、一般式(1)におけるR2と一般式(3)におけるR4とは、同じ基であってもよいし、異なる基であってもよい。
なお、単結合とは、R5が、結合基としては存在せず、R5が、結合しうる位置に、O原子が直接結合していることを示す(以降についても同様である)。また、「複数のR5」および「複数のR6」とあるのは、上記においてi+j=2である場合について示したものである(以降についても同様である)。
一般式(6)で表される化合物としては1-ナフチルアクリレート、1-ナフチルメタクリレート、2-ナフチルアクリレート、2-ナフチルメタクリレート、1,4-ナフチルジアクリレート、9,9-ビス [4-(2-アクリロイルオキシエトキシ)フェニル]フルオレン、1,4-エチレンオキシドジメタクリレートナフタレンが挙げられる。
化合物(7)で表される化合物としては、9,9-ビス[4-(2-アクリロイルオキシエトキシ)フェニル]フルオレン、9,9-ビス[4-(2-メタクリロイルオキシエトキシ)フェニル]フルオレン、9,9-ビス[4-(2-メタクリロイルオキシエトキシ)-3-メチルフェニル]フルオレン、9,9-ビス[4-(2-アクリロイルオキシエトキシ)-3、5-ジメチルフェニル]フルオレン、9,9-ビス[4-(2-メタクリロイルオキシエトキシ)-3、5-ジメチルフェニル]フルオレンが挙げられる。なお、一般式(7)では、2つあるフェニレン基にそれぞれ1つのR11が、記されているが、1つのフェニレン基に複数のR11が、結合していてもよい。
一般式(8)で表される化合物としてはノルボルネンモノアクリレート、ノルボルネンジアクリレート、ノルボルネンエチレンオキシドアクリレート、ノルボルネンオキシドジアクリレートが挙げられる。
一般式(9)で表される化合物としてはアダマンタンモノアクリレート、アダマンタンジアクリレート、アダマンタンエチレンオキシドアクリレート、アダマンタンエチレンオキシドジアクリレートが挙げられる。
一般式(10)で表される化合物としては、N-アクリロイルオキシエチルヘキサヒドロフタルイミドが挙げられる。
透過率=exp(-4πkt/λ)
なお、作製した硬化膜の膜厚が1μmからはずれた際には、以下の式にて計算できる。
膜厚が1μmあたりの透過率={(透過率/100)^ (1/t)}*100にて計算できる。
ただし、kは消衰係数、tは膜厚、λは測定波長、を表す。
PGMEA:プロピレングリコールモノメチルエーテルアセテート
DAA:ジアセトンアルコール
ポリシロキサン化合物の溶液の固形分濃度は、以下の方法により求めた。アルミカップにポリシロキサン化合物の溶液を1.5g秤取し、ホットプレートを用いて250℃で30分間加熱して液分を蒸発させた。加熱後のアルミカップに残った固形分を秤量して、ポリシロキサン化合物の溶液の固形分濃度を求めた。
300mlのナスフラスコにp-アミノ安息香酸を23.23g、PGMEAを209.05g仕込み、室温にて30分間撹拌してp-アミノ安息香酸を溶解させた。得られた溶液に、イソシアネートプロピルトリエトキシシランを46.53g、ジラウリン酸ジブチルスズを1.19g仕込み、70℃のオイルバスで1時間撹拌した。その後室温まで放冷し、析出した固体をガラスフィルターにて濾取、乾燥させ、カルボキシル基含有シラン化合物(A)を得た。収量は46.7gだった。
300mlのナスフラスコにp-ヒドロキシ安息香酸を23.39g、PGMEAを210.5g仕込み、室温にて30分間撹拌してp-ヒドロキシ安息香酸を溶解させた。得られた溶液に、イソシアネートプロピルトリエトキシシランを46.53g、ジラウリン酸ジブチルスズを1.19g仕込み、40℃のオイルバスで3時間撹拌した。その後室温まで放冷し、析出した固体をガラスフィルターにて濾取、乾燥させ、カルボキシル基含有シラン化合物(B)を得た。収量は42.4gだった。
500mlの三口フラスコに3-アクリロキシプロピルトリメトキシシランを7.03g(0.03mol)、カルボキシル基含有シラン化合物(A)を15.37g(0.04mol)、1-ナフチルトリメトキシシラン7.45g(0.03mol)、酸化チタン-酸化ケイ素複合粒子のメタノール分散液(20.6重量%)である“オプトレイク” (登録商標)TR-527(商品名、日揮触媒化成(株)製、数平均粒子径は15nm)を156g(オルガノシランが完全縮合した場合の重量(22.3g)100重量部に対して、粒子含有量150重量部)、DAAを83.84g仕込み、室温で撹拌しながら水5.4gにリン酸0.217gを溶かしたリン酸水溶液を10分間かけて添加した。なお前記数平均粒子径はダイナミック光散乱高度計DLS-8000(大塚電子(株)製)を用いて、動的光散乱法により測定した。
500mlの三口フラスコに3-アクリロキシプロピルトリメトキシシランを5.86g(0.025mol)、カルボキシル基含有シラン化合物(B)を19.26g(0.05mol)、1-ナフチルトリメトキシシラン6.21g(0.025mol)、酸化チタン粒子のプロピレングリコールモノメチルエーテルアセテート分散液(20.2重量%)(登録商標)NOD-7771GTB(商品名、ナガセケムテックス(株)製、数平均粒子径は25nm)を181.4g(オルガノシランが完全縮合した場合の重量(24.4g)100重量部に対して、粒子含有量150重量部)、DAAを89.12g仕込み、室温で撹拌しながら水5.4gにリン酸0.157gを溶かしたリン酸水溶液を10分間かけて添加した。その後、調製例1と同様に加熱撹拌して(a)金属化合物粒子として酸化チタン粒子が分散した(b)ポリシロキサン化合物の溶液を得た。得られた溶液の固形分濃度を35重量%になるようにDAAにて希釈した。なお、実施例での組成において、本調製例2にて得た溶液に含まれる(a)金属化合物粒子と(b)ポリシロキサン化合物とを総称して「PS-02」と記す。
500mlの三口フラスコにp-スチリルトリメトキシシラン5.61g(0.025mol)、カルボキシル基含有シラン化合物(B)を19.21g(0.05mol)、1-アントラセニルトリメトキシシラン7.45g(0.025mol)、酸化チタン-酸化ケイ素複合粒子のメタノール分散液(20.6重量%)である(登録商標)“オプトレイク”TR-550(商品名、日揮触媒化成(株)製、数平均粒子径は20nm)を175.7g(オルガノシランが完全縮合した場合の重量(24.1g)100重量部に対して、粒子含有量150重量部)、DAAを88.03g仕込み、室温で撹拌しながら水5.4gにリン酸0.155gを溶かしたリン酸水溶液を10分間かけて添加した。その後、調製例1と同様に加熱撹拌して(a)金属化合物粒子として酸化チタン-酸化ケイ素複合粒子が分散した(b)ポリシロキサン化合物の溶液を得た。得られた溶液の固形分濃度を35重量%になるようにDAAにて希釈した。なお、実施例での組成において、本調製例3にて得た溶液に含まれる(a)金属化合物粒子と(b)ポリシロキサン化合物とを総称して「PS-03」と記す。
500mlの三口フラスコにp-スチリルトリメトキシシラン11.22g(0.05mol)、3-トリメトキシシリルプロピルコハク酸を6.56g(0.025mol)、1-ナフチルシランを6.21g(0.025mol)、23.4%の酸化チタン分散液である“ナノユース”(登録商標)OZ-30M(酸化チタン粒子、日産化学工業(株)製、数平均粒子径は7nm)112.38g(オルガノシランが完全縮合した場合の重量(17.5g)100重量部に対して、粒子含有量150重量部)、DAAを64.63g仕込み、室温で撹拌しながら水5.85gにリン酸0.120gを溶かしたリン酸水溶液を10分間かけて添加した。その後、調製例1と同様に加熱撹拌して(a)金属化合物粒子として酸化チタン粒子が分散した(b)ポリシロキサン化合物の溶液を得た。得られた溶液の固形分濃度を35重量%になるようにDAAにて希釈した。なお、実施例での組成において、本調製例4にて得た溶液に含まれる(a)金属化合物粒子と(b)ポリシロキサン化合物とを総称して「PS-04」と記す。
500mlの三口フラスコにp-スチリルトリメトキシシラン11.22g(0.05mol)、3-トリメトキシシリルプロピルコハク酸を6.56g(0.025mol)、1-ナフチルシランを6.21g(0.025mol)、23.4%の酸化チタン分散液である“ナノユース”(登録商標)OZ-30M(酸化チタン粒子、日産化学工業(株)製、数平均粒子径は7nm)112.38g(オルガノシランが完全縮合した場合の重量(18.9g)100重量部に対して、粒子含有量150重量部)、DAAを64.63g仕込み、室温で撹拌しながら水5.85gにリン酸0.120gを溶かしたリン酸水溶液を10分間かけて添加した。その後、調製例1と同様に加熱撹拌して(a)金属化合物粒子として酸化チタン粒子が分散した(b)ポリシロキサン化合物の溶液を得た。得られた溶液の固形分濃度を35重量%になるようにDAAにて希釈した。なお、実施例での組成において、本調製例5にて得た溶液に含まれる(a)金属化合物粒子と(b)ポリシロキサン化合物とを総称して「PS-05」と記す。
3-メタクリロキシプロピリトリメトキシシラン13.02g(0.05モル)、3-トリメトキシシリルプロピルコハク酸を6.56g(0.025mol)、1-アントラセニルトリメトキシシランを7.45g(0.025mol)、20.6重量%の酸化チタン-酸化ケイ素複合粒子メタノール分散液である“オプトレイク” (登録商標)TR-550(商品名、日揮触媒化成(株)製、数平均粒子径は20nm)を149.86g(オルガノシランが完全縮合した場合の重量(20.6g)100重量部に対して、粒子含有量150重量部)、DAAを75.89g仕込み、室温で撹拌しながら水5.85gにリン酸0.135gを溶かしたリン酸水溶液を10分間かけて添加した。その後、調製例1と同様に加熱撹拌して(a)金属化合物粒子として酸化チタン-酸化ケイ素複合粒子が分散した(b)ポリシロキサン化合物の溶液を得た。得られた溶液の固形分濃度を35重量%になるようにDAAにて希釈した。なお、実施例での組成において、本調製例6にて得た溶液に含まれる(a)金属化合物粒子と(b)ポリシロキサン化合物とを総称して「PS-06」と記す。
500mlの三口フラスコにメチルトリメトキシシランを5.45g(0.04mol)、フェニルトリメトキシシランを9.9g(0.05mol)、3-トリメトキシシリルプロピルコハク酸を2.6g(0.01mol)、22.0重量%の酸化チタン-酸化ケイ素複合粒子メタノール分散液である“オプトレイク” (登録商標)TR-527(商品名、日揮触媒化成(株)製、数平均粒子径は20nm)を76.9g(オルガノシランが完全縮合した場合の重量(20.5g)100重量部に対して、粒子含有量150重量部)、DAAを40.7g仕込み、室温で撹拌しながら水5.6gにリン酸0.09gを溶かしたリン酸水溶液を10分間かけて添加した。その後、調製例1と同様に加熱撹拌して(a)金属化合物粒子として酸化チタン-酸化ケイ素複合粒子が分散した(b)ポリシロキサン化合物の溶液を得た。得られた溶液の固形分濃度を35重量%になるようにDAAにて希釈した。なお、実施例での組成において、本調製例7にて得た溶液に含まれる(a)金属化合物粒子と(b)ポリシロキサン化合物とを総称して「PS-07」と記す。
500mlの三口フラスコにメチルトリメトキシシランを5.45g(0.04mol)、3-トリメトキシシリルプロピルコハク酸を5.25g(0.02mol)、1-ナフチルトリメトキシシランを9.93g(0.04mol)、20.6重量%の酸化チタン-酸化ケイ素複合粒子メタノール分散液である“オプトレイク” (登録商標)TR-550(商品名、日揮触媒化成(株)製、数平均粒子径は20nm)を102.6g(オルガノシランが完全縮合した場合の重量(14.1g)100重量部に対して、粒子含有量150重量部)、DAAを52.3g仕込み、室温で撹拌しながら水5.76gにリン酸0.103g(仕込みモノマーに対して0.50重量%)を溶かしたリン酸水溶液を10分間かけて添加した。その後、調製例1と同様に加熱撹拌して(a)金属化合物粒子として酸化チタン-酸化ケイ素複合粒子が分散した(b)ポリシロキサン化合物の溶液を得た。得られた溶液の固形分濃度を35重量%になるようにDAAにて希釈した。なお、実施例での組成において、本調製例8にて得た溶液に含まれる(a)金属化合物粒子と(b)ポリシロキサン化合物とを総称して「PS-08」と記す。
500mlの三口フラスコに3-アクリロキシプロピルトリメトキシシランを5.86g(0.025mol)、カルボキシル基含有シラン化合物(B)を19.26g(0.05mol)、フェニルトリメトキシシラン4.96g(0.025g)、酸化チタン粒子のプロピレングリコールモノメチルエーテルアセテート分散液(20.2重量%)(登録商標)NOD-7771GTB(商品名、ナガセケムテックス(株)製、数平均粒子径は25nm)を172.1g(オルガノシランが完全縮合した場合の重量(23.2g)100重量部に対して、粒子含有量150重量部)、DAAを89.12g仕込み、室温で撹拌しながら水5.4gにリン酸0.157gを溶かしたリン酸水溶液を10分間かけて添加した。その後、調製例1と同様に加熱撹拌して(a)金属化合物粒子として酸化チタン粒子が分散した(b)ポリシロキサン化合物の溶液を得た。得られた溶液の固形分濃度を35重量%になるようにDAAにて希釈した。なお、実施例での組成において、本調製例10にて得た溶液に含まれる(a)金属化合物粒子と(b)ポリシロキサン化合物とを総称して「PS-09」と記す。
ラムダエースSTM-602(商品名、大日本スクリーン製)を用いて、屈折率1.70でプリベーク膜の膜厚、現像後膜の露光部膜厚および硬化膜の膜厚を測定した。
残膜率は以下の式に従って算出した。
残膜率(%)=現像後膜の露光部膜厚÷プリベーク膜の膜厚×100
(3)感光感度の算出
得られたプリベーク膜をPLA(キヤノン(株)製PLA-501F)を用いて、超高圧水銀灯により、感度測定用のグレースケールマスク(Opto-Line製 Multi density Resolution Mask)を介してパターン露光した。設計寸法100μmの正方形パターンが現像後に剥がれず、残って形成される最小露光量を感光感度とした。
得られた現像後膜について、全ての露光量での正方形パターンを観察し、最小パターン寸法を現像後解像度とした。同様に得られた硬化膜について、全ての正方形パターンを観察し、最小パターン寸法をキュア後解像度として観察を行った。
得られた硬化膜について、大塚電子(株)製分光エリプソメータFE5000を用いて、22℃での550nmにおける屈折率を測定した。
得られた硬化膜の400nm波長による消衰係数を大塚電子(株)製分光エリプソメータFE5000により測定し、下記式により400nm波長における膜厚1μm換算での光透過率(%)を求めた。
光透過率=exp(-4πkt/λ)
ただし、kは消衰係数、tは膜厚(μm)、λは測定波長(nm)を表す。なお、作製した硬化膜の膜厚が1μmからはずれた際には、以下の式にて計算した。
膜厚が1μmあたりの透過率={(透過率/100)^ (1/t)}*100。
得られた硬化膜について、PGMEA溶剤に25℃2分間浸漬し、その前後での残膜率が99%以上のときにきわめて良好(A)、95%以上であるとき良好(B)、95%未満であるとき不良(D)であると判定した。なお残膜率は以下の式に従って算出した。
残膜率(%)=PGMEA溶剤浸漬後膜厚÷PGMEA溶剤浸漬前膜厚×100
膜厚については、上記(1)膜厚測定に記載の方法で測定した。
1.5μm角の市松模様のマスクを用いて露光後、パタ。ーニングして得られた硬化膜についてそれぞれの露光量での断面SEM写真からパターンの断面のテーパー角度を求めた。すべての露光量にて1.5μmのパターンが解像していない場合はD、すべての露光量のうちで一番高いテーパー角度が45°~60°の場合をC、60°~75°をB、75°~90°をAと表記した。
表1の組成物1の比率となるよう調合し、フッ素系界面活性剤として、DFX-18((株)ネオス製)を30ppm添加し、黄色灯下で混合、撹拌して均一溶液とした後、0.20μmのフィルターで濾過して組成物1を調製した。
組成物の成分を表1~6に示すとおりに変更したほかは実施例1と同様にして組成物2~35を調製した。得られた各組成物を用いて、実施例1と同様にしてプリベーク膜、現像後膜、硬化膜を作製し、評価を行った。評価結果を表7~9に示す。
Claims (16)
- 以下の(a)~(d)を含有するネガ型感光性樹脂組成物であって、
(a)金属化合物粒子
(b)ポリシロキサン化合物
(c)α,β-不飽和カルボン酸エステル構造を含む基を1つ以上有する化合物
(d)光重合開始剤
さらに(e)マレイミド基を有する化合物を含有することを特徴とするネガ型感光性組成物。 - R3が、アリル基、ビニル基、(メタ)アクリロイル基またはスチリル基である請求項3記載のネガ型感光性樹脂組成物。
- 前記(c)α,β-不飽和カルボン酸エステル構造を含む基を1つ以上有する化合物が、下記一般式(5)~(10)から選ばれる化合物である請求項1~4のいずれか記載のネガ型感光性樹脂組成物。
- 前記(b)ポリシロキサン化合物のR1が下記一般式(11)~(13)のいずれかで表されるジカルボン酸無水物を有する有機基である請求項1~5のいずれか記載のネガ型感光性樹脂組成物。
- (b)ポリシロキサン化合物のSi原子モル数に対する、当該ポリシロキサン化合物を構成する一般式(1)および/または(2)で示される構造単位中のSi原子モルの比が、5モル%以上30モル%以下である請求項1~6のいずれかに記載のネガ型感光性樹脂組成物。
- 前記(a)金属化合物粒子がアルミニウム化合物粒子、スズ化合物粒子、チタン化合物粒子およびジルコニウム化合物粒子から選ばれる1以上の金属化合物粒子またはアルミニウム化合物、スズ化合物、チタン化合物およびジルコニウム化合物から選ばれる1以上の金属化合物とケイ素化合物との複合粒子である請求項1~7のいずれかに記載のネガ型感光性樹脂組成物。
- 前記(a)金属化合物粒子と前記(b)ポリシロキサン化合物が部分結合している請求項1~8のいずれかに記載のネガ型感光性樹脂組成物。
- 前記(a)金属化合物粒子の数平均粒子径が、1nm~400nmである請求項1~9のいずれかに記載のネガ型感光性樹脂組成物。
- 前記(a)金属化合物粒子が、(b)ポリシロキサン化合物100重量部に対して、10重量部以上500重量部以下である請求項1~10のいずれかに記載のネガ型感光性樹脂組成物。
- 請求項1~11のいずれかに記載のネガ型感光性樹脂組成物を硬化させてなる硬化膜。
- 請求項1~11のいずれかに記載のネガ型感光性樹脂組成物を基板上に塗布し、露光した後に現像し、次いで熱硬化させる硬化膜の製造方法。
- 請求項12に記載の硬化膜を具備するLED照明。
- 請求項12に記載の硬化膜を具備するイメージセンサ。
- 少なくとも、光電変換層、カラーフィルターおよび平坦化層を順に有する裏面照射型CMOSイメージセンサであって、前記カラーフィルターは、請求項1~11のいずれかに記載のネガ型感光性樹脂組成物から得られるパターンによって着色画素が区分されており、前記平坦化層の屈折率が前記パターンの屈折率よりも小さい、CMOSイメージセンサ。
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
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SG11201606071WA SG11201606071WA (en) | 2014-01-24 | 2015-01-21 | Negative photosensitive resin composition, cured film obtained by curing same, method for producing cured film, optical device provided with cured film, and backside-illuminated cmos image sensor |
JP2015504792A JP6572769B2 (ja) | 2014-01-24 | 2015-01-21 | ネガ型感光性樹脂組成物、それを硬化させてなる硬化膜およびその製造方法ならびにそれを具備する光学デバイスおよび裏面照射型cmosイメージセンサ |
EP15740612.5A EP3098653B1 (en) | 2014-01-24 | 2015-01-21 | Negative photosensitive resin composition, cured film obtained by curing same, method for producing cured film, optical device provided with cured film, and backside-illuminated cmos image sensor |
KR1020167021968A KR102300782B1 (ko) | 2014-01-24 | 2015-01-21 | 네거티브형 감광성 수지 조성물, 그것을 경화시켜서 이루어지는 경화막과 그 제조 방법 및 그것을 구비하는 광학 디바이스, 그리고 이면 조사형 cmos 이미지 센서 |
US15/113,119 US9977329B2 (en) | 2014-01-24 | 2015-01-21 | Negative photosensitive resin composition, cured film obtained by curing same, method for producing cured film, optical device provided with cured film, and backside-illuminated CMOS image sensor |
CN201580005547.3A CN106415393B (zh) | 2014-01-24 | 2015-01-21 | 负型感光性树脂组合物、使其固化而成的固化膜及其制造方法、以及具有其的光学设备及背面照射型cmos图像传感器 |
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KR20160113155A (ko) | 2016-09-28 |
EP3098653A1 (en) | 2016-11-30 |
EP3098653A4 (en) | 2017-10-04 |
SG11201606071WA (en) | 2016-09-29 |
KR102300782B1 (ko) | 2021-09-13 |
CN106415393A (zh) | 2017-02-15 |
JP6572769B2 (ja) | 2019-09-11 |
US9977329B2 (en) | 2018-05-22 |
CN106415393B (zh) | 2020-04-07 |
EP3098653B1 (en) | 2020-07-29 |
US20170010532A1 (en) | 2017-01-12 |
TWI666511B (zh) | 2019-07-21 |
TW201533529A (zh) | 2015-09-01 |
JPWO2015111607A1 (ja) | 2017-03-23 |
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