CN104040432A - Negative photosensitive resin composition - Google Patents
Negative photosensitive resin composition Download PDFInfo
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- CN104040432A CN104040432A CN201380004941.6A CN201380004941A CN104040432A CN 104040432 A CN104040432 A CN 104040432A CN 201380004941 A CN201380004941 A CN 201380004941A CN 104040432 A CN104040432 A CN 104040432A
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- sensitive resin
- monomer
- resin combination
- negative light
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/52—Amides or imides
- C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
- C08F220/58—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide containing oxygen in addition to the carbonamido oxygen, e.g. N-methylolacrylamide, N-(meth)acryloylmorpholine
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/36—Amides or imides
- C08F222/40—Imides, e.g. cyclic imides
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
-
- 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
-
- 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
- H05B33/02—Details
- H05B33/04—Sealing arrangements, e.g. against humidity
-
- 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
- H05B33/22—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of auxiliary dielectric or reflective layers
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/36—Amides or imides
- C08F222/38—Amides
Abstract
To provide a negative photosensitive resin composition that can be made into a thick film, the composition being devoid of tackiness even before exposure, enabling a pattern to be formed at high resolution by alkali development, and yielding a high-transparency film that exhibits minimal shrinkage after post-baking. A negative photosensitive resin composition containing components (A), (B), and (C). Component (A) is a copolymer obtained by copolymerizing a monomer mixture containing at least (i) N-alkoxymethyl(meth)acrylamide and (ii) a monomer having an alkali soluble group, component (B) is a photoacid generator, and component (C) is a solvent.
Description
Technical field
The present invention relates to negative light-sensitive resin combination and the cured film by its acquisition.More specifically, the present invention relates to photosensitive polymer combination suitable in display material purposes and cured film thereof and use the various materials of this cured film.
Background technology
The known epoxy-cationic polymerization that contains epoxy compound and photoacid generator is UV cured resin, and the transparency is high and can thick-film (for example, patent documentation 1).But, because film after coating and before exposure has viscosity, so operability is poor.In addition, owing to can not utilizing the development of aqueous alkali, so must utilize the development of organic solvent.With regard to alkali develops, although think and can in polymkeric substance, introduce carboxyl, in the case of the monomer with epoxy radicals with have the copolymerization of monomer of carboxyl, in polymerization, epoxy radicals and carboxyl easily react, and are difficult to control synthesizing of polymkeric substance.In addition, allow to control reaction synthetic polymer, storage stability is also low.
For example, as the material can alkali developing, the known minus material that contains the radical polymerization syzygy with the polymkeric substance of acryloyl group, multifunctional acrylic monomer and optical free radical initiating agent (, patent documentation 2).In this invention, although can develop by alkali by introduce carboxyl in polymkeric substance, in order to carry out the necessary high viscosity of thick-film, so operability is poor.In addition, owing to being polymerized to free radical system, suppress so be easily subject to surperficial oxygen in the time of photocuring, exist surperficial film to reduce the problem that becomes large.
On the other hand, although positive shaped material resolution is high, be difficult to also low (for example, patent documentation 3) of thick-film and the transparency.
From the viewpoint of these, expect that the transparency is high and can alkali develop, also high material of operability in the time of thick-film.
Prior art document
Patent documentation
Patent documentation 1: international application published WO2008/007764 communique
Patent documentation 2: TOHKEMY 2004-302389 communique
Patent documentation 3: Japanese kokai publication hei 8-339082 communique
Summary of the invention
The problem that invention will solve
In view of the foregoing, the invention provides a kind of negative light-sensitive resin combination, it can thick-film, does not also have viscosity before exposure, can be developed and be formed pattern with high resolving power by alkali, and the film transparency forming is high, also little in rear baking post shrinkage.
The means of dealing with problems
Present inventor, in order to address the above problem the result of having carried out concentrated research, has finally made the present invention.
That is, relate to following aspect,
As the 1st aspect, a kind of negative light-sensitive resin combination, it contains following (A) composition, (B) composition and (C) solvent,
(A) composition: the multipolymer being formed by monomer mixture copolymerization, described monomer mixture at least contains (i) N-alkoxy methyl (methyl) acrylamide and (ii) has the monomer of alkali solubility group,
(B) composition: photoacid generator,
(C) composition: solvent;
As the 2nd aspect, according to the negative light-sensitive resin combination described in the 1st aspect, the monomer for (ii) of (A) composition with alkali solubility group is maleimide;
As the 3rd aspect, according to the negative light-sensitive resin combination described in the 1st aspect or the 2nd aspect, based on 100 mass parts photosensitive polymer combinations, its sensitizer that also contains 0.1～10 mass parts is as (D) composition;
As the 4th aspect, according to the negative light-sensitive resin combination described in the 1st aspect or the 2nd aspect, it also contains the polymkeric substance with hydroxyl as (E) composition;
As the 5th aspect, according to the negative light-sensitive resin combination described in 3 aspects, the 1st aspect to the, (A) composition is the multipolymer being formed by monomer mixture copolymerization, and described monomer mixture also contains the monomer with hydroxyl;
As the 6th aspect, according to the negative light-sensitive resin combination described in 5 aspects, the 1st aspect to the, it also contains crosslinking chemical as (F) composition;
As the 7th aspect, a kind of cured film, it uses the negative light-sensitive resin combination described in any one in 6 aspects, the 1st aspect to the to obtain;
As the 8th aspect, a kind of liquid crystal display interlayer dielectric, it comprises the cured film described in the 7th aspect;
As the 9th aspect, a kind of optical filter, it comprises the cured film described in the 7th aspect.
The effect of invention
Photosensitive polymer combination of the present invention, owing to not having viscosity before exposure, can alkali develops, even the in the situation that of thick film, also can form the transparency, painting film figure that resolution is high, so the most applicable formation is as the tectosome of optics.
Embodiment
Negative light-sensitive resin combination of the present invention is for containing following (A) composition, (B) composition and (C) photosensitive polymer combination of solvent.
(A) composition: the multipolymer being formed by monomer mixture copolymerization, described monomer mixture at least contains (i) N-alkoxy methyl (methyl) acrylamide and (ii) has the monomer of alkali solubility group,
(B) composition: photoacid generator,
(C) solvent.
< (A) composition >
(A) composition is the multipolymer being formed by monomer mixture copolymerization, and described monomer mixture at least contains (i) N-alkoxy methyl (methyl) acrylamide and (ii) has the monomer of alkali solubility group.
In the present invention, multipolymer refers to, the monomer that uses acrylate, methacrylate, acrylamide, Methacrylamide, styrene etc. to have unsaturated double-bond carries out copolymerization and the polymkeric substance that obtains.
(A) multipolymer of composition, as long as having the multipolymer of such structure, the skeleton of high molecular main chain and the kind of side chain etc. that form multipolymer are not particularly limited.
But (A) multipolymer of composition, if number-average molecular weight exceedes 100000 and excessive, the developability of unexposed portion reduces, on the other hand, if number-average molecular weight is too small lower than 2000, exposure portion is curing insufficient, thereby while development, has the situation of composition stripping.Therefore, number-average molecular weight is in 2000～100000 scope.
Be used for the representation of (i) N-alkoxy methyl (methyl) formula for acrylamide (1) of (A) composition:
[changing 1]
(R in formula
1represent the alkyl of hydrogen atom, halogen atom or carbon number 1～6.R in formula
2represent the alkyl of hydrogen atom or carbon number 1～10.)
As the concrete example of these monomers, can enumerate N-(methoxy) acrylamide, N-(methoxy) Methacrylamide, N-(n-butoxy methyl) acrylamide, N-(n-butoxy methyl) Methacrylamide, N-(isobutoxy methyl) acrylamide, N-(isobutoxy methyl) Methacrylamide etc.
As the monomer for (ii) of (A) composition with alkali solubility group, can enumerate, there is the monomer of carboxyl, phenol hydroxyl, anhydride group, dimaleoyl imino.
As the monomer with carboxyl, can enumerate, for example, acrylic acid, methacrylic acid, crotonic acid, list-(2-(acryloxy) ethyl) phthalic ester, list-(2-(methacryloxy) ethyl) phthalic ester, N-(carboxyl phenyl) maleimide, N-(carboxyl phenyl) Methacrylamide, N-(carboxyl phenyl) acrylamide, 4 vinyl benzoic acids etc.
As the monomer with phenol hydroxyl, can enumerate, for example, hydroxy styrenes, N-(hydroxy phenyl) acrylamide, N-(hydroxy phenyl) Methacrylamide, N-(hydroxy phenyl) maleimide etc.
As the monomer with anhydride group, can enumerate, for example, maleic anhydride, itaconic anhydride etc.
As the monomer with dimaleoyl imino, can enumerate, for example, maleimide.
In addition, in the present invention, in the time that acquisition has particular functional group's multipolymer, can be used together and there is particular functional group's monomer and monomer that can copolymerization.
As the concrete example of this monomer, can enumerate acrylate compounds, methacrylate compound, N-substituted maleimide amines, vinyl cyanide, acrylamide compound, methacryl amines, distyryl compound and vinyl compound etc.
Although enumerated the concrete example of above-mentioned monomer, be not limited to these monomers below.
As aforementioned acrylate compounds, can enumerate, for example, methyl acrylate, ethyl acrylate, isopropyl acrylate, acrylic acid benzene methyl, acrylic acid naphthalene ester, acrylic acid anthracene ester, acrylic acid anthryl methyl esters, phenyl acrylate, acrylic acid 2,2,2-trifluoro ethyl ester, tert-butyl acrylate, cyclohexyl acrylate, isobornyl acrylate, acrylic acid 2-methoxyl ethyl ester, methoxyl triethylene glycol acrylate, acrylic acid 2-ethoxy ethyl ester, tetrahydrofurfuryl acrylate, acrylic acid 3-methoxyl butyl ester, 2-methyl-2-adamantyl acrylate, 2-propyl group-2-adamantyl acrylate, 8-methyl-8-tri-encircles decyl acrylate, acrylic acid 2-hydroxy methacrylate, acrylic acid 2-hydroxy propyl ester, acrylic acid 4-hydroxyl butyl ester, acrylic acid 2,3-dihydroxy propyl ester, diethylene glycol monoacrylate, caprolactone 2-(acryloxy) ethyl ester, PEG ethylether acrylate, 5-acryloxy-6-hydroxyl norborene-2-carboxyl-6-lactone, acryloyl group ethyl isocyanate and 8-ethyl-8-tri-encircle decyl acrylate, glycidyl acrylate etc.
As aforementioned methacrylate compound, can enumerate, for example, methyl methacrylate, β-dimethyl-aminoethylmethacrylate, isopropyl methacrylate, methacrylic acid benzene methyl, methacrylic acid naphthalene ester, methacrylic acid anthracene ester, methacrylic acid anthryl methyl esters, phenyl methacrylate, methacrylic acid 2,2,2-trifluoro ethyl ester, Tert-butyl Methacrylate, cyclohexyl methacrylate, isobornyl methacrylate, methacrylic acid 2-methoxyl ethyl ester, methoxyl triethylene glycol methacrylate, methacrylic acid 2-ethoxy ethyl ester, tetrahydrofurfuryl methacrylate, methacrylic acid 3-methoxyl butyl ester, 2-methyl-2-adamantyl methacrylate, gamma-butyrolacton methacrylate, 2-propyl group-2-adamantyl methacrylate, 8-methyl-8-tri-encircles decyl methacrylate, 2-hydroxyethyl methacrylate, methacrylic acid 2-hydroxy propyl ester, methacrylic acid 4-hydroxyl butyl ester, methacrylic acid 2,3-dihydroxy propyl ester, diethylene glycol monomethacrylates, caprolactone 2-(methacryloxy) ethyl ester, PEG ethylether methacrylate, 5-methacryloxy-6-hydroxyl norborene-2-carboxyl-6-lactone, methacryl ethyl isocyanate and 8-ethyl-8-tri-encircle decyl methacrylate, glycidyl methacrylate etc.
As aforementioned N-substituted maleimide amines, can enumerate, for example, N-methyl maleimide, N-phenylmaleimide and N-N-cyclohexylmaleimide etc.
As aforementioned distyryl compound, can enumerate, for example, styrene, methyl styrene, chlorostyrene, bromstyrol etc.
As aforementioned vinyl compound, can enumerate, for example, methyl vinyl ether, benzyl vinyl ether, vinyl naphthalene, vinyl anthracene, vinyl biphenyl, vinylcarbazole, 2-hydroxyethyl vinyl ether, Vinyl phenyl ether and propyl vinyl ether etc.
The method that obtains the multipolymer that is used for the particular functional group of having of the present invention is not particularly limited, for example, can by make to have particular functional group's monomer, described in have beyond particular functional group's monomer can copolymerization the monomer with non-reacted functional group and the solvent that coexists according to the polymerization initiator of expecting etc. in, at the temperature of 50～110 DEG C, carry out polyreaction and obtain.Now, the solvent using, as long as dissolving the monomer that forms the acrylic acid series copolymer with particular functional group and the solvent with particular functional group's acrylic acid series copolymer, is just not particularly limited.As concrete example, can enumerate the solvent of recording in (C) described later solvent.
The acrylic acid series copolymer with particular functional group obtaining by this way, is generally the solution state being dissolved in solvent.
In addition, the solution of the multipolymer obtaining in the above described manner is under agitation put in ether, water etc. it is precipitated again, by the sediment filtration washing generating, then under normal pressure or decompression, carry out normal temperature or heat drying, thereby can form the powder of multipolymer.By such operation, can remove the polymerization initiator, the unreacted monomer that coexist with multipolymer, result, can obtain the multipolymer powder of having refined.In the situation that single job can not be fully refining, the powder of acquisition is dissolved in to solvent again, repeat aforesaid operations.
In the present invention, also can directly use the polymeric solution of aforesaid propylene acid based copolymer, or also this powder can be dissolved in to for example (C) described later solvent formation solution state again and use.
In addition, in the present invention, (A) multipolymer of composition can be also the potpourri of multiple specific copolymer.
As the copolymerization ratio of monomer, be preferably N-alkoxy methyl (methyl) acrylamide/alkali solubility monomer/other=10～60/10～40/0～80 weight portions.In the situation that alkali solubility monomer is very few, unexposed portion is insoluble to developer solution and easily becomes the reason of residual film, residue.Too much in the situation that, the curability deficiency of exposure portion, existence can not form the possibility of pattern.In the situation that N-alkoxy methyl (methyl) acrylamide is very few, photo-curable deficiency, the possibility that exists exposure portion to dissolve in the time developing.Too much in the situation that, the dissolubility that has a unexposed portion is not enough and become the possibility of the reason of residual film, residue.
< (B) composition >
(B) composition is photoacid generator.The sour kind that can be used for compositions of thermosetting resin of the present invention does not have particular determination.As the concrete example of such photoacid generator, can enumerate following material.
[changing 2]
[changing 3]
[changing 4]
[changing 5]
[changing 6]
[changing 7]
[changing 8]
[changing 9]
[changing 10]
In addition, as the photoacid generator of (B) composition, can enumerate chlorinated diphenyl base iodine
, diphenyl iodine
fluoroform sulphonate, diphenyl iodine
mesylate, diphenyl iodine
toluene sulfonate, brominated diphenyl base iodine
, diphenyl iodine
tetrafluoroborate, diphenyl iodine
hexafluoro antimonate, diphenyl iodine
hexafluoro arsenate, two (to tert-butyl-phenyl) iodine
hexafluorophosphate, two (to tert-butyl-phenyl) iodine
mesylate, two (to tert-butyl-phenyl) iodine
toluene sulfonate, two (to tert-butyl-phenyl) iodine
fluoroform sulphonate, two (to tert-butyl-phenyl) iodine
tetrafluoroborate, chlorination two (to tert-butyl-phenyl) iodine
, chlorination two (rubigan) iodine
, two (rubigan) iodine
tetrafluoroborate, chlorinated triphenyl base sulfonium, bromination triphenylsulfonium, triphenylsulfonium fluoroform sulphonate, three (p-methoxyphenyl) sulfonium tetrafluoroborate, three (p-methoxyphenyl) sulfonium hexafluoro phosphonate, three (to ethoxyl phenenyl) sulfonium tetrafluoroborate, chlorinated triphenyl base sulfonium, bromination triphenylsulfonium, three (p-methoxyphenyl) sulfonium tetrafluoroborate, three (p-methoxyphenyl) sulfonium hexafluoro phosphonate, three (to ethoxyl phenenyl) sulfonium tetrafluoroborate etc.
The content of (B) composition in negative light-sensitive resin combination of the present invention, with respect to 100 mass parts (A) composition, is preferably 0.5～20 mass parts, more preferably 1～15 mass parts, more preferably 2～10 mass parts.In this ratio lower than 0.5 mass parts in the situation that, exist photoreactivity to fall and situation that susceptibility reduces.In addition, if exceed 20 mass parts, the situation that the transmissivity of the film that existence forms reduces, the storage stability of solution reduces.
< (C) solvent >
It is for dissolving for (A) of the present invention composition and (B) composition, and dissolve according to the solvent of aftermentioned (D) composition of expecting to add, (E) composition, (F) composition etc., as long as having the solvent of this dissolving power, its kind and structure etc. are not particularly limited.
As such (C) solvent, can enumerate, for example, glycol monoethyl ether, ethylene glycol monoethyl ether, methylcellosolve acetate, ethyl cellosolve acetate, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, propylene glycol, propylene glycol monomethyl ether, propylene glycol methyl ether acetate, propylene glycol propyl ether acetic acid esters, toluene, dimethylbenzene, MEK, cyclopentanone, cyclohexanone, 2-butanone, 3-methyl-2 pentanone, 2 pentanone, 2-HEPTANONE, gamma-butyrolacton, 2 hydroxy propanoic acid ethyl ester, 2-hydroxy-2-methyl ethyl propionate, ethoxy ethyl acetate, hydroxacetic acid ethyl ester, 2-hydroxy-3-methyl methyl butyrate, 3-methoxy methyl propionate, 3-methoxy propyl acetoacetic ester, 3-ethoxyl ethyl propionate, 3-ethoxy-propionic acid methyl esters, methyl pyruvate, ethyl pyruvate, ethyl acetate, butyl acetate, ethyl lactate, butyl lactate, N, dinethylformamide, N, N-dimethyl acetamide and 1-METHYLPYRROLIDONE etc.
These solvents can use separately one, or can be used in combination two or more.
In these (C) solvents, good from film, safe angle is considered, preferably propylene glycol monomethyl ether, diethylene glycol monomethyl ether, propylene glycol methyl ether acetate, ethyl lactate, butyl lactate etc.The solvent that these solvents are used usually used as photo anti-corrosion agent material uses.
< (D) composition >
(D) composition is sensitizer.In the case of the photoacid generator of (B) composition to the film that makes to be formed by negative light-sensitive resin combination of the present invention expose to the sun the reaction rate of light wavelength little, can improve reaction rate by adding sensitizer.As the concrete example of such sensitizer, can enumerate, 9,10-dibutoxy anthracene, 9-hydroxymethyl anthracene, thioxanthones, ITX, ITX, CTX, 2,4-diethyl thioxanthone, anthraquinone, 1,2-dihydroxy anthraquinone, 2-EAQ, Isosorbide-5-Nitrae-diethoxy naphthalene etc.
As (D) composition, can use a kind in aforementioned sensitizer, or can be used in combination two or more.
The addition of these sensitizers, with respect to 100 mass parts (A) composition, is preferably 0.1～10 mass parts, more preferably 0.1～8 mass parts conventionally.If the amount of sensitizer is excessive compared with aforementioned range, the situation that exists the transparency of film to reduce.
< (E) composition >
(E) composition is the polymkeric substance with hydroxyl.As the polymkeric substance with hydroxyl, can enumerate, for example, the polymkeric substance being formed by the monomer polymerization with hydroxyl; Cellulose, hydroxypropyl cellulose; Bis-epoxy and dicarboxylic acid copolymerization and the polymkeric substance that obtains; Bis-epoxy and diphenol copolymerization and the polymkeric substance that obtains; Polyester polyol, polyether glycol, polycaprolactone polyol etc., but be preferably the polymkeric substance or the hydroxypropyl cellulose that are formed by the monomer polymerization with hydroxyl.
As the above-mentioned polymkeric substance being formed by the monomer polymerization with hydroxyl, can enumerate, in above-mentioned (A) composition, enumerate can the monomer of copolymerization in the polymkeric substance that there is the monomer homopolymerization of hydroxyl or form with monomer copolymerization that can copolymerization.
As in (A) composition, enumerate can the monomer of copolymerization in there is the monomer of hydroxyl, can enumerate, acrylic acid 2-hydroxy methacrylate, acrylic acid 2-hydroxy propyl ester, acrylic acid 4-hydroxyl butyl ester, acrylic acid 2,3-dihydroxy propyl ester and 5-acryloxy-6-hydroxyl norborene-2-carboxyl-6-lactone; 2-hydroxyethyl methacrylate, methacrylic acid 2-hydroxy propyl ester, methacrylic acid 4-hydroxyl butyl ester, methacrylic acid 2,3-dihydroxy propyl ester and 5-methacryloxy-6-hydroxyl norborene-2-carboxyl-6-lactone etc.
As monomer that can copolymerization, can enumerate, for example, in (A) composition, enumerate can copolymerization monomer.
These polymkeric substance with hydroxyl can use separately, or can be used in combination two or more.
The content of the polymkeric substance with hydroxyl of (E) composition in negative light-sensitive resin combination of the present invention, based on the multipolymer of 100 mass parts (A) composition, is preferably 5～150 mass parts, more preferably 10～120 mass parts.In the situation that this ratio is too small compared with aforementioned range, the situation that exists the susceptibility of negative light-sensitive resin combination to reduce, on the other hand, excessive compared with aforementioned range in the situation that, the developability that has a unexposed portion reduces and becomes the situation of the reason of residual film, residue.
< (F) composition >
As the crosslinking chemical of (F) of the present invention composition, as long as the crosslinking chemical that can react with (A) composition by the acid being produced by (B) composition.As such crosslinking chemical, can enumerate the compound such as epoxy compound, methylol compound, but be preferably methylol compound.
As the concrete example of above-mentioned methylol compound, can enumerate the compounds such as alkoxy methyl glycoluril, alkoxy methyl benzoguanamine and alkoxy methyl melamine.
As the concrete example of alkoxy methyl glycoluril, can enumerate, for example, 1,3,4,6-tetra-(methoxy) glycoluril, 1,3,4,6-tetra-(butoxymethyl) glycoluril, 1,3,4,6-tetra-(hydroxymethyl) glycoluril, 1,3-bis-(hydroxymethyl) urea, 1,1,3,3-tetra-(butoxymethyl) urea, 1,1,3,3-tetra-(methoxy) urea, 1,3-bis-(hydroxymethyl)-4,5-dihydroxy-2-imidazolone and 1,3-bis-(methoxy)-4,5-dimethoxy-2-imidazolone etc.As commercially available product, can enumerate, glycoluril compounds (the trade name: サ イ メ Le (registered trademark) 1170 that Mitsui サ イ テ ッ Network (strain) is produced, パ ウ ダ ー リ Application Network (registered trademark) 1174) etc. compound, carbamide resin (trade name: UFR (registered trademark) 65) methylates, butylation carbamide resin (trade name: UFR (registered trademark) 300, U-VAN10S60, U-VAN10R, U-VAN11HV), urea/diaion (high condensed type that large Japanese イ Application キ chemical industry (strain) is produced, trade name: ベ ッ カ ミ Application (registered trademark) J-300S, ベ ッ カ ミ Application P-955, ベ ッ カ ミ Application N) etc.
As the concrete example of alkoxy methyl benzoguanamine, can enumerate tetramethoxy methylbenzene guanamines etc.As commercially available product, can enumerate (trade name: ニ カ ラ ッ Network (registered trademark) BX-4000, ニ カ ラ ッ Network BX-37, ニ カ ラ ッ Network BL-60, ニ カ ラ ッ Network BX-55H) that (trade name: サ イ メ Le (registered trademark) 1123), (strain) three and the ケ ミ カ Le that Mitsui サ イ テ ッ Network (strain) is produced produced etc.
As the concrete example of alkoxy methyl melamine, can enumerate, for example, hexamethoxy methyl cyanuramide etc.As commercially available product, can enumerate methoxy methyl fundamental mode melamine compound (trade name: サ イ メ Le (registered trademark) 300, サ イ メ Le 301, サ イ メ Le 303, サ イ メ Le 350), butoxymethyl type melamine compound (trade name: マ イ コ ー ト (registered trademark) 506, マ イ コ ー ト 508) that Mitsui サ イ テ ッ Network (strain) is produced, three and ケ ミ カ Le produce methoxy methyl fundamental mode melamine compound (trade name: ニ カ ラ ッ Network (registered trademark) MW-30, ニ カ ラ ッ Network MW-22, ニ カ ラ ッ Network MW-11, ニ カ ラ ッ Network MS-001, ニ カ ラ ッ Network MX-002, ニ カ ラ ッ Network MX-730, ニ カ ラ ッ Network MX-750, ニ カ ラ ッ Network MX-035), butoxymethyl type melamine compound (trade name: ニ カ ラ ッ Network (registered trademark) MX-45, ニ カ ラ ッ Network MX-410, ニ カ ラ ッ Network MX-302) etc.
In addition, melamine compound, carbamide compound, glycoluril compounds and the benzoguanamine compound condensation that can be the hydrogen atom that can make this amino have been replaced by methylol or alkoxy methyl and the compound that obtains.For example, can enumerate the compound of the high molecular of being manufactured by melamine compound and benzoguanamine compound that United States Patent (USP) is recorded for No. 6323310.As the commercially available product of aforementioned melamine compound, can enumerate, trade name: サ イ メ Le (registered trademark) 303 (Mitsui サ イ テ ッ Network (strain) production) etc., as the commercially available product of aforementioned benzoguanamine compound, can enumerate trade name: サ イ メ Le (registered trademark) 1123 (Mitsui サ イ テ ッ Network (strain) production) etc.
These crosslinking chemicals can use separately, or can be used in combination two or more.
The content of the crosslinking chemical of (F) composition in negative light-sensitive resin combination of the present invention, based on the multipolymer of 100 mass parts (A) composition, is preferably 5～100 mass parts, more preferably 10～80 mass parts.In the situation that this ratio is too small compared with aforementioned range, the situation that exists the photo-curable of negative light-sensitive resin combination to reduce, on the other hand, excessive compared with aforementioned range in the situation that, the developability that has a unexposed portion reduces and becomes the situation of the reason of residual film, residue.
Other adjuvant of < >
In addition, negative light-sensitive resin combination of the present invention, do not damaging under the prerequisite of effect of the present invention, can contain as required the dissolution accelerators such as quencher, surfactant, rheology control agent, pigment, dyestuff, preserving stabilizer, defoamer or polyhydric phenol, polybasic carboxylic acid etc.
< negative light-sensitive resin combination >
Negative light-sensitive resin combination of the present invention is for dissolved the polymkeric substance of (A) composition and (B) composition of the photoacid generator of composition in (C) solvent, and respectively according to expecting also to contain more than one in crosslinking chemical and other adjuvant of the polymkeric substance with hydroxyl, (F) composition of sensitizer, (E) composition of (D) composition.
Wherein, the preferred example of negative light-sensitive resin combination of the present invention is as described below.
[1]: a kind of negative light-sensitive resin combination, (B) composition that it contains 0.5～20 mass parts based on 100 mass parts (A) composition, and these compositions are dissolved in (C) solvent.
[2]: a kind of negative light-sensitive resin combination, it based on 100 mass parts (A) composition, also contains 0.1～10 mass parts (D) composition in the composition of above-mentioned [1].
[3]: a kind of negative light-sensitive resin combination, it based on 100 mass parts (A) composition, also contains 5～150 mass parts (E) composition in the composition of above-mentioned [1] or [2].
[4]: a kind of negative light-sensitive resin combination, it based on 100 mass parts (A) composition, also contains 5～100 mass parts (F) composition in the composition of above-mentioned [1]～[3].
The ratio of solid constituent in negative light-sensitive resin combination of the present invention, as long as each composition is dissolved in solvent and is just not particularly limited equably, for example, is 1～80 quality %, or is for example 5～60 quality %, or be 10～50 quality %.Here, solid constituent refers to, removes the composition after (C) solvent from whole compositions of negative light-sensitive resin combination.
The modulator approach of negative light-sensitive resin combination of the present invention, be not particularly limited, as its modulation method, can enumerate, for example, (A) composition (multipolymer) is dissolved in to (C) solvent, in this solution, mix (B) composition (photoacid generator) with regulation ratio, form the method for uniform solution, or, in the suitable stage of this modulator approach, as required, further add (D) composition (sensitizer), (E) composition (thering is the polymkeric substance of hydroxyl), (F) composition (crosslinking chemical) and other adjuvant and the method for mixing.
In the time of modulation negative light-sensitive resin combination of the present invention, can directly use the solution of the specific copolymer obtaining by polyreaction in (C) solvent, in this case, form uniform solution in the solution (B) composition etc. is joined with aforementioned same mode to this (A) composition time, for the object of concentration adjustment, also further additional input (C) solvent.Now, (C) solvent using in the forming process of specific copolymer and modulation when negative light-sensitive resin combination (C) solvent for concentration adjustment both can be the same or different.
And preferably using aperture is that the filtrator etc. of 0.2 about μ m will re-use after the solution filter of modulated negative light-sensitive resin combination.
< film and cured film >
By rotary coating, flow coat, print roll coating, slit coating, slit continues, and (for example, silicon/silicon dioxide is substrate coated at semiconductor substrate for rotary coating, ink-jet application etc.; Silicon nitride board; Be coated with the such as substrate of aluminium, molybdenum, chromium etc. of metal; Glass substrate; Quartz base plate; Ito substrate etc.) upper coating negative light-sensitive resin combination of the present invention, then, predrying by using heating plate or baking oven etc. to carry out, can form film.Then,, by this film is carried out to heat treated, can form negative photosensitive resin film.
As the condition of this heat treated, for example, can adopt heating-up temperature and heat time in the scope that is selected from aptly temperature 70 C～160 DEG C, 0.3～60 minute time.Heating-up temperature and heat time are preferably 80 DEG C～140 DEG C, 0.5～10 minute.
In addition, the thickness of the negative photosensitive resin film being formed by negative light-sensitive resin combination is for example 0.1～30 μ m, or is for example 0.5～20 μ m, is further for example 1～15 μ m.
The negative photosensitive resin film being formed by negative light-sensitive resin combination of the present invention, if use the mask with predetermined pattern by ultraviolet ray, ArF, KrF, F
2the light exposures such as laser, the sour effect producing by the photoacid generator (PAG) by (B) composition contained in negative photosensitive resin film, the exposure portion in this film becomes the part that is insoluble to alkaline-based developer.
Then, negative photosensitive resin film is exposed after heating (PEB).As heating condition in this case, can adopt heating-up temperature and heat time in the scope that is selected from aptly temperature 70 C～150 DEG C, 0.3～60 minute time.
Then, use alkaline-based developer to develop.Accordingly, the part not being exposed in negative photosensitive resin film is removed, form the relief of pattern-like.
As the alkaline-based developer that can use, can enumerate, for example, the aqueous solution of the alkali metal hydroxides such as potassium hydroxide, NaOH; The aqueous solution of the quaternary ammonium hydroxides such as Tetramethylammonium hydroxide, tetraethyl ammonium hydroxide, choline; The alkaline aqueous solution of the amine aqueous solutions such as monoethanolamine, propylamine, ethylenediamine etc.In addition, also can in these developer solutions, add surfactant etc.
In above-mentioned developer solution, conventionally use the tetraethyl ammonium hydroxide aqueous solution of 0.1～2.38 quality % as the developer solution of photoresist, even in photosensitive polymer combination of the present invention, use this alkaline-based developer also can not cause the problems such as swelling, can develop well.
In addition, as developing method, liquid pool method, infusion process, shake infusion process etc. can be used.Development time is now generally 15～180 seconds.
After development, by flowing water, negative photosensitive resin film is carried out to for example washing of 20～90 seconds, then by using pressurized air or compressed nitrogen or removing by the moisture on rotary wind capable person substrate, form figuratum film thereby obtain.
Then, by being formed to film, this pattern carries out the rear baking for heat curing, particularly, by using heating plate, baking oven etc. to heat, can obtain the excellences such as thermotolerance, the transparency, smooth voltinism, low water absorbable, chemical-resistant and there is the film of good embossed pattern.
As rear baking, conventionally adopt with the following method, being selected under 140 DEG C～250 DEG C heating-up temperatures in temperature range, the in the situation that of on heating plate, process 5～30 minutes, the in the situation that of in baking oven, process 30～90 minutes.
Then,, by this rear baking, can obtain the cured film of the good pattern form of having of target.
As mentioned above, utilize negative light-sensitive resin combination of the present invention can form the film with fine pattern, described film does not have viscosity before exposure, can develop by alkali, even if the thickness that is 10 μ m left and right also has sufficient high sensitive, and the film of exposure portion reduces very little in the time developing.In addition this cured film transparency, thermotolerance and solvent resistance excellence.Therefore, can be suitably for the various films of liquid crystal display, OLED display, touch panel element etc., such as interlayer dielectric, diaphragm, dielectric film, blooming etc.
Embodiment
To enumerate the mode of embodiment, the present invention will be described in more detail below, but the present invention is not subject to the restriction of these embodiment.
[dummy suffix notation using in embodiment]
The meaning of the dummy suffix notation using in following examples is as described below.
MAA: methacrylic acid
MI: maleimide
MMA: methyl methacrylate
BMAA:N-(n-butoxy methyl) acrylamide
HEMA: 2-hydroxyethyl methacrylate
GMA: glycidyl methacrylate
ST: styrene
AIBN: azoisobutyronitrile
PAG1:TPS-TF (Japan's synthetic (strain) produces) (compound name: triphenylsulfonium fluoroform sulphonate)
PAG2:GSID-26-1 (BASF production) (the represented compound of aforementioned formula (79))
PAG3:IRGACURE369 (BASF production) (Photoepolymerizationinitiater initiater)
CYM: サ イ メ Le 303 (ProductNames) (compound name: hexamethoxy methyl cyanuramide) that サ イ テ ッ Network ジ ャ パ Application is produced
HMA:9-hydroxymethyl anthracene
HPC: hydroxy propyl cellulose
DPHA: dipentaerythritol five/six acrylate
BTEAC: benzyl triethyl ammonium chloride
PGME: propylene glycol monomethyl ether
PGMEA: propylene glycol methyl ether acetate
JE: the JER157S70 that ジ ャ パ Application エ Port キ シ レ ジ Application (strain) is produced
[mensuration of number-average molecular weight and weight-average molecular weight]
The GPC device (Shodex (registered trademark) post KF803L and KF804L) that uses Japanese light splitting (strain) to produce, measures the specific copolymer obtaining according to following synthesis example and number-average molecular weight and the weight-average molecular weight of specific crosslinked under the condition of wash-out eluting solvent tetrahydrofuran is flowed with the flow (40 DEG C of column temperature) in post of 1ml/ minute.In addition, following number-average molecular weight is (hereinafter referred to as Mn.) and weight-average molecular weight (hereinafter referred to as Mw.) all with polystyrene conversion value representation.
< synthesis example 1 >
Use MI (26.0g), BMAA (45.0g), ST (29.0g) as the monomer component that forms multipolymer, use AIBN (2g) as radical polymerization initiator, by making them carry out polyreaction in solvent PGME (238g), obtain the copolymer solution (copolymer concentration: 30 quality %) of Mn4300, Mw9800 (P1).In addition, polymerization temperature is adjusted to the temperature of 60 DEG C～90 DEG C.
< synthesis example 2 >
Use MAA (20.0g), BMAA (50.0g), ST (30.0g) as the monomer component that forms multipolymer, use AIBN (2g) as radical polymerization initiator, by making them carry out polyreaction in solvent PGME (238g), obtain the copolymer solution (copolymer concentration: 30 quality %) of Mn4000, Mw9200 (P2).In addition, polymerization temperature is adjusted to the temperature of 60 DEG C～90 DEG C.
< synthesis example 3 >
Use MAA (20.0g), BMAA (50.0g), HEMA (30.0g) as the monomer component that forms multipolymer, use AIBN (2g) as radical polymerization initiator, by making them carry out polyreaction in solvent PGME (238g), obtain the copolymer solution (copolymer concentration: 30 quality %) of Mn4800, Mw10500 (P3).In addition, polymerization temperature is adjusted to the temperature of 60 DEG C～90 DEG C.
< synthesis example 4 >
Use MAA (20.0g), HEMA (40.0g) MMA (40.0g) as the monomer component that forms multipolymer, use AIBN (2g) as radical polymerization initiator, by making them carry out polyreaction in solvent PGME (238g), obtain the copolymer solution (copolymer concentration: 30 quality %) of Mn3900, Mw8500 (P4).In addition, polymerization temperature is adjusted to the temperature of 60 DEG C～90 DEG C.
< is synthesis example 1 > relatively
Use MAA (50.0g), MMA (50.0g) as the monomer component that forms multipolymer, use AIBN (2g) as radical polymerization initiator, by making them carry out polyreaction in solvent PGMEA (120g), obtain copolymer solution (copolymer concentration: 40 quality %).In addition, polymerization temperature is adjusted to the temperature of 60 DEG C～90 DEG C.By adding GMA (33.0g), BTEAC (1.1g), PGMEA (49.5g) to react, obtained the solution (specific copolymer concentration: 40.5 quality %) of (A) composition (specific copolymer) of Mn8700, Mw22000 (P5) in this multipolymer of 200g.In addition, temperature of reaction is adjusted to 90～120 DEG C.
< is synthesis example 2 > relatively
Use MAA (30.0g), GMA (50.0g), ST (20.0g) as the monomer component that forms multipolymer, use AIBN (2g) as radical polymerization initiator, although make them in solvent PGME (238g), at the temperature of 60 DEG C～90 DEG C, carry out polyreaction, in polyreaction, there is gelation and can not be used for after evaluation.
< embodiment 1～7 and comparative example 1～2 >
According to the composition shown in following table 1, in the solution of (A) composition, mix (B) composition, (C) solvent and (D) composition and (E) composition and (F) composition with the ratio of regulation, at room temperature stir 3 hours, form uniform solution, thereby modulated the negative light-sensitive resin combination of each embodiment and each comparative example.
Table 1
For each negative light-sensitive resin combination of obtained embodiment 1～7 and comparative example 1 and 2, measure respectively thickness after prebake conditions, have inviscid, transmissivity, resolution, susceptibility.
[evaluation of thickness after prebake conditions]
Use spin coater that negative light-sensitive resin combination is coated on silicon chip, then at the temperature of 110 DEG C, on heating plate, carry out 120 seconds prebake conditions, thereby form film.The F20 that uses FILMETRICS to produce measures the thickness of this film.
[evaluation of transmissivity]
Use spin coater that negative light-sensitive resin combination is coated on quartz base plate, then at the temperature of 110 DEG C, on heating plate, carry out 120 seconds prebake conditions, thereby form film.The ultraviolet lamp PLA-600FA producing by キ ャ ノ Application is taking the light intensity at 365nm place as 5.5mW/cm
2ultraviolet ray this film is irradiated 36 seconds.This film is carried out on heating plate heating after exposure in 120 seconds at the temperature of 95 DEG C, then at the temperature of 150 DEG C, in baking oven, carry out baking after 15 minutes, thereby form cured film.Use ultraviolet visible spectrophotometer (the SIMADSU UV-2550 model that (strain) Shimadzu Seisakusho Ltd. produces) this cured film to be measured to the transmissivity of 400nm wavelength.
[evaluation of resolution]
Use spin coater that negative light-sensitive resin combination is coated on alkali-free glass, then at the temperature of 110 DEG C, on heating plate, carry out 120 seconds prebake conditions, thereby form film.Utilize ultraviolet lamp PLA-600FA that キ ヤ ノ Application (strain) produces taking the light intensity at 365nm place as 5.5mW/cm
2ultraviolet ray by the mask of line & intermittent pattern, this film is carried out to 190mJ/cm
2irradiate.Then, at the temperature of 110 DEG C, on heating plate, carry out heating after exposure in 120 seconds.Then by flooding and develop for 60 seconds in Tetramethylammonium hydroxide (hereinafter referred to as the TMAH) aqueous solution of 2.38 quality %, then use ultrapure water to carry out 20 second flow water washings, thereby form pattern.The pattern of making is calcined 15 minutes in the baking oven of 150 DEG C, the pattern after calcining is carried out to SEM observation, the minimum pattern size that the live width of pattern is consistent with the live width of mask is made as resolution.
[evaluation of susceptibility]
Use spin coater that negative light-sensitive resin combination is coated on alkali-free glass, then at the temperature of 110 DEG C, on heating plate, carry out 120 seconds prebake conditions, thereby form film.Use ultraviolet lamp PLA-600FA that キ ヤ ノ Application (strain) produces taking the light intensity at 365nm place as 5.5mW/cm
2the mask of the line & intermittent pattern of ultraviolet ray by 20 μ m every 50mJ/cm
2this film is irradiated.Then, at the temperature of 110 DEG C, on heating plate, carry out heating after exposure in 120 seconds.Then by flooding and develop for 60 seconds in the TMAH aqueous solution of 2.38 quality %, then use ultrapure water to carry out 20 second flow water washings, thereby form pattern.The lowest exposure amount that can form the pattern of 20 μ m is made as susceptibility.
[result of evaluation]
The result of carrying out above evaluation is as shown in table 2 below.
Table 2
As judged in the result shown in by table 2, the negative light-sensitive resin combination of embodiment 1～7 all can, with thick film coatings more than 10 μ m, even for thick film also has high-transmission rate and can develop by alkali, and keep high resolving power, susceptibility.
For comparative example 1, can not thick-film, the residual film ratio after rear baking is also below 90%, for low.For comparative example 2, after prebake conditions, there is viscosity, can not use alkaline developer to develop.
Utilizability in industry
According to negative light-sensitive resin combination of the present invention; be suitable as the material of the cured film such as diaphragm in various displays such as forming thin film transistor (TFT) (TFT) type liquid crystal display cells, organic EL, touch panel element, planarization film, dielectric film, be especially suitable as the dielectric film of interlayer dielectric, the organic EL of diaphragm, array planarization film, the capacitive touch panels of the interlayer dielectric, the color filter that form TFT type liquid crystal cell, material as the tectosome plate of display surface anti-reflecting layer etc.
Claims (9)
1. a negative light-sensitive resin combination, it contains following (A) composition, (B) composition and (C) solvent,
(A) composition: the multipolymer being formed by monomer mixture copolymerization, described monomer mixture at least contains (i) N-alkoxy methyl (methyl) acrylamide and (ii) has the monomer of alkali solubility group,
(B) composition: photoacid generator,
(C) solvent.
2. negative light-sensitive resin combination according to claim 1, the monomer for (ii) of (A) composition with alkali solubility group is maleimide.
3. negative light-sensitive resin combination according to claim 1 and 2, based on the photosensitive polymer combination of 100 mass parts, its sensitizer that also contains 0.1～10 mass parts is as (D) composition.
4. according to the negative light-sensitive resin combination described in any one in claim 1～3, it also contains the polymkeric substance with hydroxyl as (E) composition.
5. according to the negative light-sensitive resin combination described in any one in claim 1～3, (A) composition is the multipolymer being formed by monomer mixture copolymerization, and described monomer mixture also contains the monomer with hydroxyl.
6. according to the negative light-sensitive resin combination described in any one in claim 1～5, it also contains crosslinking chemical as (F) composition.
7. a cured film, its right to use requires the negative light-sensitive resin combination described in any one in 1～6 to obtain.
8. a liquid crystal display interlayer dielectric, it comprises cured film claimed in claim 7.
9. an optical filter, it comprises cured film claimed in claim 7.
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| Application Number | Priority Date | Filing Date | Title |
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| JP2012-008689 | 2012-01-19 | ||
| JP2012008689 | 2012-01-19 | ||
| PCT/JP2013/050428 WO2013108716A1 (en) | 2012-01-19 | 2013-01-11 | Negative photosensitive resin composition |
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| CN104040432A true CN104040432A (en) | 2014-09-10 |
| CN104040432B CN104040432B (en) | 2018-09-14 |
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| JP (1) | JP6150072B2 (en) |
| KR (1) | KR102027756B1 (en) |
| CN (1) | CN104040432B (en) |
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| CN105765458A (en) * | 2013-10-21 | 2016-07-13 | 日产化学工业株式会社 | Negative photosensitive resin composition |
| CN110392864A (en) * | 2017-03-29 | 2019-10-29 | 东丽株式会社 | Negative light-sensitive resin combination, cured film, the element for having cured film and organic el display and its manufacturing method |
| CN110412829A (en) * | 2018-04-26 | 2019-11-05 | 东友精细化工有限公司 | Negative light-sensitive resin combination, photocuring pattern and image display device |
| CN115160495A (en) * | 2022-08-15 | 2022-10-11 | 四川华造宏材科技有限公司 | Photoresist film-forming resin containing maleimide structure and preparation method thereof |
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| EP3098653B1 (en) | 2014-01-24 | 2020-07-29 | Toray Industries, Inc. | 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 |
| WO2015187413A1 (en) * | 2014-06-03 | 2015-12-10 | The Chemours Company Fc, Llc | Passivation layer comprising a photocrosslinked fluoropolymer |
| TW201840759A (en) * | 2017-02-22 | 2018-11-16 | 日商日產化學工業股份有限公司 | Cured film formation composition, orientation material and retardation material |
| KR102170935B1 (en) * | 2019-08-28 | 2020-10-29 | 주식회사 삼양사 | A curable resin composition and an electronic device comprising a cured layer formed therefrom |
| JP7393229B2 (en) | 2020-01-31 | 2023-12-06 | Ntn株式会社 | Power supply and demand adjustment system and power supply and demand adjustment method |
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| KR20140117512A (en) | 2014-10-07 |
| TWI569100B (en) | 2017-02-01 |
| KR102027756B1 (en) | 2019-10-02 |
| JP6150072B2 (en) | 2017-06-21 |
| WO2013108716A1 (en) | 2013-07-25 |
| CN104040432B (en) | 2018-09-14 |
| TW201348876A (en) | 2013-12-01 |
| JPWO2013108716A1 (en) | 2015-05-11 |
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