CN104570607A - Negative type photosensitive resin composition of the insulating film and insulating film using the same - Google Patents
Negative type photosensitive resin composition of the insulating film and insulating film using the same Download PDFInfo
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- CN104570607A CN104570607A CN201410648857.4A CN201410648857A CN104570607A CN 104570607 A CN104570607 A CN 104570607A CN 201410648857 A CN201410648857 A CN 201410648857A CN 104570607 A CN104570607 A CN 104570607A
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
- G03F7/0382—Macromolecular compounds which are rendered insoluble or differentially wettable the macromolecular compound being present in a chemically amplified negative photoresist composition
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- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1339—Gaskets; Spacers; Sealing of cells
- G02F1/13394—Gaskets; Spacers; Sealing of cells spacers regularly patterned on the cell subtrate, e.g. walls, pillars
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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
- G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
- G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/022—Quinonediazides
- G03F7/023—Macromolecular quinonediazides; Macromolecular additives, e.g. binders
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/022—Quinonediazides
- G03F7/023—Macromolecular quinonediazides; Macromolecular additives, e.g. binders
- G03F7/0233—Macromolecular quinonediazides; Macromolecular additives, e.g. binders characterised by the polymeric binders or the macromolecular additives other than the macromolecular quinonediazides
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
-
- 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
- G03F7/027—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
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
- G03F7/033—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
- G03F7/0388—Macromolecular compounds which are rendered insoluble or differentially wettable with ethylenic or acetylenic bands in the side chains of the photopolymer
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- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Nonlinear Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Mathematical Physics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Optics & Photonics (AREA)
- Materials For Photolithography (AREA)
Abstract
A negative type photosensitive resin composition of the insulating film, and use it. This is disclosed in the photosensitive resin composition, said composition comprising: (A) an alkali-soluble resin, the alkali-soluble resin comprising (a1) derived from an ethylenically unsaturated carboxylic acid, ethylenically unsaturated carboxylic acid anhydride or mixtures thereof structural units, (a2) a structural unit derived from a monomer represented by "Formula 1", (a3) a structural unit derived from a monomer represented by the formula 2, and (a4) derived from an ethylenically unsaturated compound structural unit, wherein a structural unit different from the structural unit (a1) - Total (a3) any one of the structural unit (a2) which comprise the alkali-soluble resin and (a3) is 10-50mol%, based on the total moles of structural units; (B) a photopolymerizable monomer; and (C) a photopolymerization initiator.
Description
Invention field
The present invention relates to a kind of minus (negative-type) photosensitive resin composition and its insulation film of use, particularly relate to a kind of photosensitive resin composition for having high-resolution pattern development characteristic, good time stability, high resistance to sudden heating, good thermotolerance and chemical-resistant cured film, this cured film may be used for forming the insulation film as the display device of liquid crystal display (LCD) etc., and relates to the insulation film using this resin combination.
background of invention
Eurymeric and negative-type photosensitive resin composition are used for manufacturing the insulation film comprised in the various display devices of liquid crystal display, organic electroluminescenoe device etc.
In the process that exposure, baked after development and shortwave (such as UV) absorb, containing alkali soluble resins and 1, the conventional positive resin of 2-diazonium quinone (quinonediazide) compound has problems usually, the decolouring such as brought due to pyrolytic or cause LCD to occur undesirable afterimage owing to producing impurity.
Therefore, the negative-type photosensitive resin composition attempted by having good transmittance and susceptibility after being provided in heat curing process solves these problems.Equally; in the display apparatus of such as thin film transistor (TFT) (TFT) LCD etc., be proposed as organic insulation film at the alkali soluble resins photosensitive resin composition comprised derived from the structural unit of (methyl) glycidyl acrylate to protect TFT matrix and to provide the thermotolerance of improvement and photostability etc.
But, owing to having the trend along with time reduction stability derived from the traditional building blocks of (methyl) glycidyl acrylate, thus produced problem is conventional organic insulation film can not indicate enough thermotolerances, the amount therefore derived from the structural unit of (methyl) glycidyl acrylate is limited.
In this connection, Korean laid-open patent gazette No.2010-0109370 discloses a kind of photosensitive resin composition for insulation film, it to be included in outside the traditional building blocks derived from (methyl) glycidyl acrylate also containing derived from the alkali soluble resins of structural unit of unsaturated compound with aliphatic epoxy base, and its total amount is at least 71wt%.But, the insulation film prepared from such photosensitive resin composition has poor time stability and can not obtain fully pattern shape due to poor developing performance.
Summary of the invention
Therefore, an object of the present invention is to provide a kind of negative-type photosensitive resin composition, it can provide high-resolution pattern development characteristic, good time stability, high resistance to sudden heating, good thermotolerance and good chemical resistance, and uses the insulation film of this resin combination.
According to an aspect of the present invention, provide a kind of photosensitive resin composition, it comprises:
(A) alkali soluble resins, it comprises (a1) derived from the structural unit of ethylenically unsaturated carboxylic acids, ethylenically unsaturated carboxylic acids acid anhydride or its potpourri, (a2) derived from the structural unit of the monomer of formula 1 expression, (a3) derived from the structural unit of the monomer of formula 2 expression, (a4) derived from the structural unit of alefinically unsaturated compounds, it is different from any one in structural unit (a1)-(a3), wherein the total amount of the structural unit (a2) that comprises of alkali soluble resins and (a3) is 10-50mol%, mole total amount of structure based unit;
(B) monomer of photopolymerization; With
(C) Photoepolymerizationinitiater initiater
[formula 1]
[formula 2]
Wherein
R
1and R
3hydrogen or C independently of one another
1-4alkyl; With
R
2and R
4hydrogen or C independently of one another
1-4alkylidene.
Photosensitive resin composition of the present invention can provide has high-resolution pattern development characteristic, good time stability, good thermotolerance and chemical-resistant cured film.Therefore, it can be used as the dielectric film of LCD device effectively.
Embodiment
Hereafter, technical characteristic of the present invention will be described in detail.
(A) alkali soluble resins
Alkali soluble resins of the present invention comprises (a1) derived from ethylenically unsaturated carboxylic acids, the structural unit of ethylenically unsaturated carboxylic acids acid anhydride or its potpourri, (a2) derived from the structural unit with the unsaturated monomer of aliphatic epoxide groups that formula 1 represents, (a3) derived from the structural unit with the unsaturated monomer of non-fat race epoxide group that formula 2 represents, (a4) derived from the structural unit of alefinically unsaturated compounds, it is different from any one in structural unit (a1)-(a3), wherein the total amount of the structural unit (a2) that comprises of alkali soluble resins and (a3) is 10-50mol%, mole total amount of structure based unit.
(a1) derived from the structural unit of ethylenically unsaturated carboxylic acids, ethylenically unsaturated carboxylic acids acid anhydride or its potpourri
In the present invention, structural unit (a1) is derived from ethylenically unsaturated carboxylic acids, ethylenically unsaturated carboxylic acids acid anhydride or its potpourri.Ethylenically unsaturated carboxylic acids and ethylenically unsaturated carboxylic acids acid anhydride are the polymerizable unsaturated monomers in molecule with at least one carboxylic acid group.Its example comprises unsaturated monocarboxylic acid, such as (methyl) acrylic acid, crotonic acid, α-acrylate chloride, cinnamic acid etc.; Unsaturated dicarboxylic acid and its acid anhydrides, such as maleic acid, maleic anhydride, fumaric acid, itaconic acid, itaconic anhydride, citraconic acid, citraconic anhydride, mesaconic acid (mesaconic acid) etc.; Trivalent or more the unsaturated polybasic carboxylic acid of valency and acid anhydrides thereof; List [(methyl) acryloxyalkyl] ester of the polybasic carboxylic acid of divalence or more valency, such as single [2-(methyl) acryloyl-oxyethyl] succinate, list [2-(methyl) acryloyl-oxyethyl] phthalate ester etc.Unit derived from the compound of above-mentioned demonstration can comprise in the copolymer with the form of single compound or two or more combinations, but is not limited thereto.Consider developing property, preferably (methyl) acrylic acid.
Amount derived from the structural unit (a1) of ethylenically unsaturated carboxylic acids, ethylenically unsaturated carboxylic acids acid anhydride or its potpourri can be 5-50mol%, preferred 10-40mol%, based on the integral molar quantity of the structural unit of formation alkali soluble resins.In numerical range, resin combination demonstrate good developing property and the film prepared thus can have good pattern can developability.
In this manual, " (methyl) propenyl " ((meth) acryl) refers to " propenyl " and/or " methylpropenyl ", and " (methyl) acrylate " means " acrylate " and/or " methacrylate ".
(a2) derived from the structural unit with the unsaturated monomer of aliphatic epoxide groups that formula 1 represents
In the present invention, the unsaturated monomer with aliphatic epoxide groups that structural unit (a2) represents derived from formula 1:
[formula 1]
Wherein
R
1hydrogen or C
1-4alkyl; With
R
2c
1-4alkylidene.
Preferably, in formula 1, R
1be hydrogen or methyl, and the unsaturated monomer with aliphatic epoxy base is acrylic acid 3,4-epoxycyclohexyl-methyl ester or methacrylic acid 3,4-epoxycyclohexyl-methyl ester.
(a3) derived from the structural unit with the unsaturated monomer of non-fat race epoxide group that formula 2 represents
In the present invention, the unsaturated monomer with non-fat race epoxide group that structural unit (a3) represents derived from formula 2:
[formula 2]
Wherein
R
3hydrogen or C
1-4alkyl; With
R
4c
1-4alkylidene.
Preferably, in formula 2, R
3be hydrogen or methyl, and the unsaturated monomer with non-fat race epoxy radicals is glycidyl acrylate or methyl propenoic acid glycidyl base ester.
The total amount of structural unit (a2) and (a3) can be 10-50mol%, preferred 15-45mol%, based on the integral molar quantity of the structural unit of formation alkali soluble resins.In numerical range, the storage stability of composition can be kept and reserved rate (retention rate) can be improved.
In addition, the mol ratio of structural unit (a2) and structural unit (a3) can be 50-99: 50-1, preferred 50-80: 50-20.In numerical range, the pattern development of good time stability, good thermotolerance and chemical resistance and improvement can be obtained.
(a4) derived from the structural unit of alefinically unsaturated compounds, it is different from structural unit (a1)-(a3)
in any one
In the present invention, structural unit (a4) is derived from alefinically unsaturated compounds, and it is different from any one in structural unit (a1)-(a3).Its example can comprise the alefinically unsaturated compounds containing aromatic ring, such as (methyl) phenyl acrylate, (methyl) benzyl acrylate, (methyl) acrylic acid 2-phenoxyethyl acrylate, (methyl) acrylic acid phenoxy group binaryglycol ester, (methyl) acrylic acid is to Nonylphenoxy macrogol ester, (methyl) acrylic acid is to Nonylphenoxy polypropylene glycol ester, (methyl) acrylic acid tribromo phenylester, styrene, methyl styrene, dimethyl styrene, trimethyl styrene, ethyl styrene, diethyl, triethylbenzene ethene, propylstyrene, butylstyrene, hexyl benzene ethene, heptyl benzene ethene, octyl styrene, fluorinated styrenes, chloro styrene, brominated styrene, benzene iodide ethene, methoxy styrene, ethoxystyrene, propoxyl group styrene, p-hydroxy-alpha-methyl styrene, acetylbenzene ethene, vinyltoluene, divinylbenzene, vinylphenol, adjacent vinyl benzyl methyl ether, between vinyl benzyl methyl ether and to vinyl benzyl methyl ether, esters of unsaturated carboxylic acids, such as (methyl) methyl acrylate, (methyl) ethyl acrylate, (methyl) butyl acrylate, (methyl) acrylate, (methyl) i-butyl base ester, (methyl) acrylate tert-buthyl, (methyl) cyclohexyl acrylate, (methyl) ethylhexylacrylate, (methyl) acrylic acid tetrahydrofurfuryl ester, (methyl) hydroxyethyl acrylate, (methyl) acrylic acid 2-hydroxy-propyl ester, (methyl) acrylic acid 2-hydroxyl-3-chloropropyl ester, (methyl) acrylic acid 4-hydroxybutyl ester, (methyl) glycerol acrylate, Alpha-hydroxy methyl methacrylate, Alpha-hydroxy ethyl methacrylate, Alpha-hydroxy propyl methacrylate, Alpha-hydroxy butyl methacrylate, (methyl) acrylic acid 2-methoxy ethyl ester, (methyl) acrylic acid 3-methoxy butyl acrylate, (methyl) ethioxy binaryglycol ester, (methyl) methoxyethyl triglycol ester, (methyl) methoxyethyl tripropylene glycol ester, (methyl) acrylic acid PEG methyl ether-ether, (methyl) acrylic acid tetrafluoro propyl diester, (methyl) acrylic acid 1,1,1,3,3,3-hexafluoro isopropyl ester, (methyl) acrylic acid octafluoro amyl group ester, (methyl) acrylic acid 17 fluorine decyl ester, (methyl) isobornyl acrylate, (methyl) acrylic acid bicyclopentyl ester, (methyl) acrylic acid dicyclopentenyl ester and (methyl) acrylic acid two cyclopentyloxy ethyl ester, (methyl) acrylic acid dicyclopentenyl oxygen base ethyl ester, there is the tertiary amine of N-vinyl, such as NVP, N-vinylcarbazole and N-polyvinyl morpholinone, unsaturated ethers, such as vinyl methyl ether and EVE, with unsaturated acyl imines, such as N-phenylmaleimide, N-(4-chlorphenyl) maleimide, N-(4-hydroxy phenyl) maleimide and N-N-cyclohexylmaleimide.Structural unit derived from above-mentioned model compounds can be involved with the form of single compound or two or more combination.
The amount of structural unit (a4) can be 5-70mol%, preferred 10-65mol%, based on mole total amount of the structural unit of formation alkali soluble resins.In numerical range, the reactivity that easily can control alkali soluble resins regulates, and the resin dissolves in aqueous based solution also can improve, thus improves the coating performance of composition significantly.
Equally, the weight-average molecular weight of alkali soluble resins of the present invention can at 500-50, in the scope of 000, and preferably 3,000-30,000.In above-mentioned scope, be desirable to the cohesive of base material, physical property, chemical resistance and viscosity.Weight-average molecular weight is the weight-average molecular weight of polystyrene control, and it is measured by gel permeation chromatography (GPC, eluant, eluent: tetrahydrofuran).
Alkali soluble resins of the present invention can be prepared by conventional method known in the art.
The consumption of alkali soluble resins can be 1-80wt%, and preferred 5-60wt%, based on the total amount of the photosensitive resin composition beyond solvent.In above-mentioned scope, the pattern after developing with good form can be obtained, and the performance as retention rate, chemical resistance etc. can be improved.
(B) monomer of photopolymerization
The monomer of photopolymerization of the present invention can be any compound by Photoepolymerizationinitiater initiater polymerization, with can be that there is the acrylic acid of at least one ethylenical unsaturated double bonds or the simple function of methacrylic acid or polyfunctional ester compounds, and can be that there is the polyfunctional compound providing chemical-resistant at least two functionality wanted.
The monomer of photopolymerization can be selected from two (methyl) acrylic acid glycol ester, two (methyl) acrylic acid propylene glycol ester, two (methyl) acrylic acid binaryglycol ester, two (methyl) acrylic acid triglycol ester, two (methyl) acrylic acid 1,6-hexanediol ester, two (methyl) polyalkylene glycol acrylate ester, two (methyl) acrylic acid polypropylene glycol ester, three (methyl) acrylic acid glycerine ester, three (methyl) acrylic acid trihydroxymethylpropanyl ester, three (methyl) acrylate, pentaerythritol, the monoesters of three (methyl) acrylate, pentaerythritol and succinic acid, four (methyl) acrylate, pentaerythritol, five (methyl) acrylic acid dipentaerythritol ester, six (methyl) acrylic acid dipentaerythritol ester, the monoesters of five (methyl) acrylic acid dipentaerythritol ester and succinic acid, six (methyl) acrylic acid dipentaerythritol ester of caprolactone modification, pentaerythritol triacrylate hexamethylene diisocyanate (reaction product of pentaerythritol triacrylate and hexamethylene diisocyanate), seven (methyl) acrylic acid tripentaerythritol ester, eight (methyl) acrylic acid tripentaerythritol ester, bisphenol A epoxy acrylate, ethylene glycol monomethyl ether acrylate and composition thereof, but be not limited thereto.
Equally; in addition to these examples; the monomer of photopolymerization can be the multifunctional urethane acrylate obtained from the compound with straight-chain alkyl-sub-, aliphatic structure and at least two isocyanate group and the reaction of compound with at least one hydroxyl, 3,4 or 5 acryloxies and/or methacryl, but is not limited thereto.
The monomer of commercially available photopolymerization can with in the present invention.The example of (methyl) acrylate of simple function comprises Aronix M-101, M-111, M-114 (Toagosei Co., Ltd manufacture), Kayarad TC-110S, TC-120S (Nippon Kayaku Co., Ltd manufactures), V-158, V-2311 (Osaka Organic Chemical Ind., Ltd. manufacture) etc.; The example of two senses (methyl) acrylate comprises Aronix M-210, M-240, M-6200 (Toagosei Co., Ltd manufacture), Kayarad HDDA, HX-220, R-604 (Nippon Kayaku Co., Ltd manufactures), V260, V312, V335HP (OsakaOrganic Chemical Ind., Ltd. manufacture) etc.; The example of trifunctional (methyl) acrylate comprises Aronix M-309, M-400, M-403, M405, M-450, M-7100, M-8030, M-8060, TO-1382 (Toagosei Co., Ltd manufacture), Kayarad TMPTA, DPHA, DPHA-40H, DPCA-20, DPCA-30, DPCA-60, DPCA-120 (Nippon Kayaku Co., Ltd manufactures), V-295, V-300, V-360, V-GPT, V-3PA, V-400 (Osaka Yuki Kayaku Co., Ltd. manufactures) etc.
The monomer of photopolymerization can separately or two or more combinationally use, the amount of the monomer of photopolymerization can be 1-100 weight portion, preferred 10-80 weight portion, based on the total amount (as solid constituent) of the alkali soluble resins of 100 weight portions.In above-mentioned scope, the resin combination with hypersensitivity, good pattern development and film characteristics can be obtained.
(C) Photoepolymerizationinitiater initiater
Photoepolymerizationinitiater initiater of the present invention is being exposed under the radiation as visible ray, ultraviolet light, deep UV (ultraviolet light) etc., produces the compound of the active substance of trigger monomer polymerization.Photoepolymerizationinitiater initiater can be radical initiator; its kind is not special restriction, but can be selected from acetophenone compound, benzophenone compound, styrax compound, benzoyl compound, xanthone (xanthone) compound, triaizine compounds, halogenated methyl oxadiazole compound, lophine dipolymer and composition thereof.
The special case of Photoepolymerizationinitiater initiater includes, but are not limited to 2,2 '-azo two (2,4-methyl pentane nitrile), 2,2 '-azo two (4-methoxyl-2,4-methyl pentane nitrile), benzoyl peroxide, lauryl peroxide, peroxidating trimethylace tonitric tertiary butyl ester, 1,1-bis-(tert-butyl hydroperoxide) cyclohexane, p-dimethylamino benzoylformaldoxime, 2-benzyl-2-(dimethylamino)-1-[4-(4-morpholinyl) phenyl]-1-butanone, 2-hydroxy-2-methyl-1-phenyl-propyl-1-ketone, benzyl dimethyl ketal, Benzophenone, styrax propyl ether, diethyl thioxanthone, 2,4-bis-(trichloromethyl)-6-p-methoxyphenyl-s-triazine, 2-trichloromethyl-5-styryl-1,3,4-oxadiazoles, 9-phenylacridine, 3-methyl-5-amino-((s-triazine-2-base) is amino)-3-phenyl coumarin, 2-(Chloro-O-Phenyl)-4,5-diphenyl-imidazole dipolymer, 1-phenyl-1,2-propanedione-2-(adjacent ethoxy carbonyl) oxime, 1-[4-(phenyl) phenyl]-Xin-1,2-diketone-2-(o-benzoyl oxime), o-benzoyl-4 '-(benzene sulfydryl) benzoyl-hexyl-one oxime, 2,4,6-trimethylphenyl carbonyl-diphenylphosphine acyl-oxygen compound, even phosphorus trialkylphenyl sulfonium salt (hexafluorophosphoro-trialkylphenylsulfonium salt) of hexafluoro, 2-mercaptobenzimidazole, 2,2 '-benzothiazole based bisulfide and composition thereof.Equally, special example is included in oxime compound disclosed in KR2004-0007700, KR2005-0084149, KR2008-0083650, KR2008-0080208, KR2007-0044062, KR2007-0091110, KR2007-0044753, KR2009-0009991, KR2009-0093933, KR2010-0097658, KR2011-0059525, WO10/102502 and WO10/133077.
The consumption of Photoepolymerizationinitiater initiater is 1-20 weight portion, preferred 1-15 weight portion, based on the alkali soluble resins (as solid constituent) of 100 weight portions.In above-mentioned scope, the resin combination with high sensitive, good pattern development and film characteristics can be obtained.
(D) other composition
Photosensitive resin composition of the present invention can also comprise other adjuvant to improve the performance of composition.Such as, other composition as (1) surfactant, (2) silane coupling agent and/or (3) solvent can be comprised.
(1) surfactant
Photosensitive resin composition of the present invention also can comprise surfactant to improve its coating performance and to stop cracking initiation, if necessary.
Surfactant is not limited to specific kind, and preferred type is fluorine based surfactant, silica-based surfactant, non-ionics etc.Consider the dispersiveness of composition, preferably from the BYK 333 of BYK Co..
The example of surfactant comprises: fluoro-or silicon-based surfactants, such as BM-1000, BM-1100 (BM CHEMIE Co., Ltd. manufactures), Megapack F 142 D, Megapack F172, MegapackF173, Megapack F183, F-470, F-471, F-475, F-482, F-489 (Dai Nippon Ink ChemicalKogyo Co., Ltd. manufactures), Florad FC-135, Florad FC-170C, Florad FC-430, FloradFC-431 (Sumitomo 3M Ltd. manufactures), Sufron S-112, Sufron S-113, Sufron S-131, Sufron S-141, Sufron S-145, Sufron S-382, Sufron SC-101, Sufron SC-102, SufronSC-103, Sufron SC-104, Sufron SC-105, Sufron SC-106 (Asahi Glass Co., Ltd. manufactures), Eftop EF301, Eftop 303, Eftop 352 (Shinakida Kasei Co., Ltd. manufactures), SH-28 PA, SH-190, SH-193, SZ-6032, SF-8428, DC-57, DC-190 (Toray SiliconCo., Ltd. manufacture), DC3PA, DC7PA, SH11PA, SH21PA, SH8400, FZ-2100, FZ-2110, FZ-2122, FZ-2222, FZ-2233 (Dow Corning Toray Silicon Co., Ltd. manufactures), TSF-4440, TSF-4300, TSF-4445, TSF-4446, TSF-4460, TSF-4452 (GE ToshibaSilicon Co., Ltd. manufactures) and BYK-333 (BYK Co., Ltd. manufactures), non-ionic surfactant, such as polyethylene oxide alkyl ethers, comprise polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, polyoxyethylene oleyl ether etc., polyoxyethylene aryl ethers, comprise polyoxyethylene octylphenyl ether, polyoxyethylene nonylplenyl ether etc., with polyoxyethylene dialkyl, comprise polyoxyethylene dilaurate, polyoxyethylene distearate etc., with organic siloxane polymer KP341 (Shin-Etsu Chemical Co., Ltd. manufacture), (methyl) acrylic acid esterbased copolymer Polyflow No.57,95 (Kyoei Yuji ChemicalCo., Ltd. manufacture) etc.They can separately or two or more combinationally use.
The amount of the surfactant that photosensitive resin composition of the present invention can comprise is 0.001-5 weight portion, preferred 0.01-1 weight portion, based on the alkali soluble resins (as solid constituent) of 100 weight portions.In above-mentioned scope, can easily coating composition.
(2) silane coupling agent
Photosensitive resin composition of the present invention also can comprise and has the silane coupling agent for improving the fusible active substituent to base material that at least one is selected from carboxyl, (methyl) acryloyl group, isocyanates, amino, sulfydryl, vinyl and epoxy radicals, if wanted.
The kind of silane coupling agent is not particularly limited, but can be selected from trimethoxysilyl benzoic acid, γ-methacryloxypropyl trimethoxy silane, vinyltriacetoxy silane.Vinyltrimethoxy silane, γ-isocyanate group propyl-triethoxysilicane, γ-glycidoxypropyltrime,hoxysilane, γ-glycidoxypropyl group triethoxysilane, β-(3,4-epoxycyclohexyl) ethyl trimethoxy silane and composition thereof.Preferably, can use and there is good reserved rate and to the fusible γ-glycidoxypropyl group triethoxysilane of base material or γ-glycidoxypropyltrime,hoxysilane.Equally, can use there is γ-isocyanate group propyl-triethoxysilicane (such as, from the KBE-9007 of Shin-Etsu Co.) that good chemical-resistant has isocyanate group.
The consumption of silane coupling agent is 0.001-5 weight portion, preferred 0.01-1 weight portion, based on the alkali soluble resins (as solid constituent) of 100 weight portions.In above-mentioned scope, the cohesive of composition to base material can be improved.
In addition, other adjuvant that just can to comprise when the physical property of photosensitive resin composition can not worsen as antioxidant, stabilizing agent etc. is only had.
(3) solvent
Photosensitive resin composition of the present invention can make fluid composition by mixing mentioned component in a solvent.
Any solvent as known in the art can be used in photosensitive resin composition, and it can be compatible with the composition in above-mentioned photosensitive resin composition, but do not react with it.
The example of solvent includes, but are not limited to, ethylene glycol monoalkyl ether acetate, such as ethylene glycol monomethyl ether acetic acid ester and ethylene glycol monomethyl ether acetate; Propylene-glycol monoalky lether, such as propylene glycol monomethyl ether, propylene glycol monoethyl, propylene glycol monopropyl ether and glycol monobutyl ether; Propylene glycol dialkyl ether, such as propylene glycol dimethyl ether, propylene glycol Anaesthetie Ether, propylene glycol dipropyl ether and propylene glycol dibutyl ethers; Dipropylene glycol dialkyl ether, such as dipropylene glycol dimethyl ether; Propylene-glycol monoalky lether acetic acid esters, such as propylene glycol monomethyl ether, propylene glycol monoethyl acetic acid esters, propylene glycol monopropyl ether acetic acid esters and glycol monobutyl ether acetic acid esters; Cellosolve (cellosolve), such as ethyl cellulose solvent and butyl cellulose solvent; Carbitol, such as butyl carbitol; Lactate, such as methyl lactate, ethyl lactate, lactic acid n-pro-pyl ester and lactic acid isopropyl esters; Aliphatic carboxylic acid esters, such as ethyl acetate, acetic acid n-pro-pyl ester, isopropyl, ro-butyl acetate, Sucrose Acetate base ester, acetic acid n-pentyl ester, acetic acid isopentyl ester, propanoic acid isopropyl ester, propionic acid n-butyl and propionic acid isobutyl; Ester, such as 3-methoxypropionic acid methyl ester, 3-methoxypropionic acid ethyl ester, 3-ethoxy-propionic acid methyl ester, 3-ethyl-ethoxypropionate, pyruvic acid methyl ester and pyruvic acid ethyl ester; Aromatic hydrocarbon, such as toluene and dimethylbenzene; Ketone, such as 2-HEPTANONE, 3-heptanone, 4-heptanone and cyclohexanone; Acid amides, such as dinethylformamide, N-methylacetamide, DMA and 1-METHYLPYRROLIDONE; Lactone, such as gamma-butyrolacton; And composition thereof.Solvent can separately or two or more combinationally use.
In photosensitive resin composition, the amount of solvent is not special restriction.But consider that composition is to the stability of base material and coating performance, based on total composition, photosensitive resin composition can make range of solid content be 5-70wt%, and the amount of preferred 10-55wt% comprises solvent.
Solid content refers to the content removed and be included in the composition that solvent obtains in resin combination of the present invention.
By photosensitive resin composition is applied on base material, then can solidifies process and form dielectric film.The dielectric film prepared thus can be used as electronic component.
Equally, the dielectric film obtained by photosensitive resin composition can be used in LCD device.
Insulation film can be prepared by conventional method known in the art.Such as, photosensitive resin composition can be coated on silicon substrate, carries out prebake 60-130 second with except desolventizing at the such as temperature of 60-130 DEG C; The photomask with predetermined pattern is used to expose under light illumination; Develop with the developer of use as tetramethyl-ammonium hydroxide solution (TMAH), coated thin film forms pattern.Then, the figuratum coated film obtained carries out the dielectric film that post-drying is wanted with preparation for 10 minutes-5 hours at the temperature of 150-300 DEG C.
Exposure is at the wavelength coverage of 200-450nm and 10-100mJ/cm
2exposure under to carry out.
The insulation film obtained by photosensitive resin composition demonstrates good pattern development characteristic, good time stability, good thermotolerance and chemical resistance.Therefore, it can be used as the dielectric film of LCD device effectively.
After this, with reference to following embodiment, the present invention will be described in more detail.But it is of the present invention that these embodiments are used to explanation, but not limit the scope of the invention.
In the following embodiments, polystyrene standard sample is used to measure weight-average molecular weight by gel permeation chromatography (GPC).
Preparation embodiment 1: prepare alkali soluble resins (A-1)
3 weight portions are as 2 of polymerization initiator, 2 '-azo two (2,4-methyl pentane nitrile), the propylene glycol monomethyl ether of 100 weight portions and the monomer mixture comprising glycidyl methacrylate (10mol%), methacrylic acid 3,4-epoxycyclohexyl-methyl ester (20mol%), methacrylic acid (23mo%), methyl methacrylate (12mol%) and styrene (35mol%) of 100 weight portions add to and be equipped with condenser and be arranged in the three-necked bottle of the drying tube on the stirrer with automatic temperature-adjusting sensor.In a nitrogen environment, temperature is elevated to 70 DEG C, and potpourri stirs the solution carrying out for 5 hours being polymerized to obtain multipolymer (A-1), and it has 10, the weight-average molecular weight (Mw) of 200.
Preparation embodiment 2-13: prepare alkali soluble resins (A-2)-(A-13)
Preparing multipolymer (A-2)-(A-13) solution, repeating the step preparing embodiment 1, except preparing except respective solution with the composition listed in following table 1 and number (weight portion).
table 1
GMA: glycidyl methacrylate
METHB: methacrylic acid 3,4-epoxycyclohexyl-methyl ester
MAA: methacrylic acid
MMA: methyl methacrylate
CHMI: methacrylic acid cyclohexyl methyl ester
DCPMA: methacrylic acid dicyclopentenyl ester
Embodiment 1
Add the acquisition multipolymer that (A-1) solid content is the preparation embodiment 1 of 100 weight portions, as (B-1) 65 weight portion six acrylic acid dipentaerythritol ester of photopolymerizable monomer, as (C-1) 4 parts by weight O XE-01 (BASF Co.) and (C-2) 1 parts by weight O XE-02 (BASF Co.) of Photoepolymerizationinitiater initiater, (D-1) solid content as surfactant is FZ-2110 (the Dow Corning Toray SiliconCo. of 0.3 weight portion, Ltd.), (E-1) solid content is the γ-glycidoxypropyl group triethoxysilane of 0.5 weight portion and makes the solid content based on composition gross weight be 25wt% as the propylene glycol monomethyl ether of solvent, use Vib. to mix 2 hours and obtain liquid form photosensitive resin composition.
Embodiment 2-8 and comparing embodiment 1-5
Repeating the step of embodiment 1 and prepare photosensitive resin composition, preparing except each composition except using the composition listed in following table 2 and number (weight portion).
The photosensitive resin composition that embodiment 1-8 and comparing embodiment 1-5 obtains makes film, and the film that test is formed is to evaluate their pattern development characteristic, time stability, resistance to sudden heating, thermotolerance and chemical resistance.Outcome record is in following table 2.
The film of preparation solidification
Use spin coater photosensitive resin composition coating on the glass substrate, the base material of coating forms 100 DEG C of prebakes the coating film that thickness is 3 μm for 90 seconds.Under not using the condition of mask, using aligner (model: MA6) to make film be exposed to irradiance rate is 30mJ/cm
2be the illumination lower regular period of 365nm with wavelength, this aligner (aligner) sends the light that wavelength is 200-450nm.Then by spraying the trimethyl ammonium oxyhydroxide as the 2.38wt% of developer, at 23 DEG C, film is made to develop 70 seconds via fog nozzle.Subsequently, film post-drying in the convective oven of 230 DEG C obtains the film of solidification for 30 minutes.
1. pattern resolution (%)
In the preparation of above-mentioned cured film, be 1 μm to be interposed between configuration space on top that thickness is the coating film of 3 μm between 10 μm, to be made up of the pattern mask of pattern the square hole being of a size of 1-15 μm between mask and base material.Three-dimensional surface measurement device measuring is used to form the critical dimension (CD, unit: μm) of the perforation pattern of pattern by 10 μm of mask size.Use the value (%) of following formulae discovery pattern development.The value of pattern resolution is lower, and the resolution of cured film is better.
Pattern resolution (%)=[(CD of mask size-perforation pattern)/(mask size)] × 100
2. time stability (%)
The 10g photosensitive resin composition being 25wt% solid content puts into 20ml vial, and vial is stored 48 hours in the stove of 40 DEG C.Then the viscosity B coefficent of resin composition solution measured by the TV-22 rotary viscosimeter using Toki Sangyo Co., Ltd. to manufacture.The resin combination of sampling 1ml, puts into viscosity meter, until temperature stabilization is at 25 DEG C, then measures viscosity by applied pressure on the main shaft of viscosity meter.5% or less viscosity improve (%) and be considered to good, 3% or less be considered to outstanding.
Ratio (%)=[(storing the initial viscosity of the viscosity-sample of rear sample under the condition of 40 DEG C/48 hours)/(initial viscosity of sample)] × 100 of viscosity-modifying
3. resistance to sudden heating (%)
In the preparation of above-mentioned cured film, the wafer substrate of 6 inches is used to substitute glass baseplate.In addition, after the thickness measuring cured film, exposed film puts into convective oven, heats 60 minutes, again measure the thickness of film at 250 DEG C.Use film thickness measurement system (model: Nanospec.) to measure the thickness of film, the thickness using following formulae discovery to cause due to thermal shock changes.The thickness reduced rate caused due to thermal shock is less, and the resistance to sudden heating of cured layer is better.
Due to thickness reduced rate (%)=[(film thickness after the film thickness first after solidification-second time solidification)/(film thickness first after solidification)] × 100 that thermal shock causes
4. thermotolerance (TGA, %)
Scraping cured film obtains the sample of 5mg, uses thermogravimetric analyzer to measure thermotolerance.230 DEG C and 250 DEG C, keep measuring while 60 minutes the weight of sample are heated to from room temperature with the speed of 10 DEG C/min at sample.Use following formulae discovery thermotolerance (weight reduced rate).The value (%) of weight reduced rate is lower, and the thermotolerance of cured film is better.
Weight reduced rate (%)=[(the sample starting weight at 25 DEG C-at the example weight of 250 DEG C of maintenances after 60 minutes)/(the sample starting weights at 25 DEG C)] × 100
5. chemical resistance (%)
In the preparation of above-mentioned cured film, the wafer substrate of 6 inches is used to substitute glass baseplate.In addition, use, the surface profile (Alpha Step) of stylus point base measures thus obtained cured film thickness of sample.1-METHYLPYRROLIDONE (NMP) is added crusher, maintain 70 DEG C in self-operated thermostatic controller at.Sample to immerse in NMP 10 minutes, then uses above-mentioned identical step detect thickness.By the chemical resistance (%) of following formulae discovery sample.Chemical-resistant value (%) is lower, and the performance of film is better.
Chemical resistance (%)=[(immersing the thickness-initial thickness after NMP)/(initial thickness)] × 100
table 2
As appreciable in above-mentioned table 2 test result, with comparing embodiment 1-5 do not comprise specific structure unit or comprise compared with cured film prepared by resin combination that content do not fall into the alkali soluble resins of the specific structure unit of particular range, the cured film prepared by the resin combination with the embodiment 1-8 of the alkali soluble resins of specific structure unit comprising specified quantitative demonstrates the over-all properties of improvement, comprises outstanding pattern definition, time stability, high resistance to sudden heating, good thermotolerance and chemical resistance.Therefore, the cured film that resin combination of the present invention obtains can effectively for the preparation of the dielectric film of LCD.
Claims (4)
1. a photosensitive resin composition, described composition comprises:
(A) alkali soluble resins, described alkali soluble resins comprises (a1) derived from ethylenically unsaturated carboxylic acids, the structural unit of ethylenically unsaturated carboxylic acids acid anhydride or its potpourri, (a2) derived from the structural unit of the monomer of formula 1 expression, (a3) derived from the structural unit of the monomer of formula 2 expression, (a4) derived from the structural unit of alefinically unsaturated compounds, described structural unit is different from any one in structural unit (a1)-(a3), wherein the total amount of the structural unit (a2) that comprises of alkali soluble resins and (a3) is 10-50mol%, mole total amount of structure based unit,
(B) monomer of photopolymerization; With
(C) Photoepolymerizationinitiater initiater
Wherein
R
1and R
3hydrogen or C independently of one another
1-4alkyl; With
R
2and R
4c independently of one another
1-4alkylidene.
2. the photosensitive resin composition of claim 1, the monomer that its Chinese style 1 represents is acrylic acid 3,4-epoxycyclohexyl-methyl ester or methacrylic acid 3,4-epoxycyclohexyl-methyl ester.
3. the photosensitive resin composition of claim 1, the monomer that its Chinese style 2 represents is glycidyl acrylate or glycidyl methacrylate.
4. the photosensitive resin composition of claim 1, wherein the molar ratio range of structural unit (a2) and structural unit (a3) is 50-99: 50-1.
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| CN111465900A (en) * | 2018-11-16 | 2020-07-28 | 株式会社Lg化学 | Photosensitive resin composition, photosensitive material, display device, and method for low-temperature curing of photosensitive resin composition |
| TWI791224B (en) * | 2021-05-26 | 2023-02-01 | 達興材料股份有限公司 | Alkali-soluble resin, protective layer composition, protective layer, laminate, and method for forming photoresist pattern |
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| KR20200014059A (en) | 2018-07-31 | 2020-02-10 | 롬엔드하스전자재료코리아유한회사 | Photosensitive resin composition and insulating film prepared therefrom |
| KR20200052028A (en) | 2018-11-06 | 2020-05-14 | 롬엔드하스전자재료코리아유한회사 | Photosensitive resin composition and insulating film prepared therefrom |
| KR20210061011A (en) * | 2019-11-19 | 2021-05-27 | 롬엔드하스전자재료코리아유한회사 | Photosensitive resin composition and insulating layer prepared therefrom |
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| JP4934353B2 (en) * | 2005-06-10 | 2012-05-16 | ドンジン セミケム カンパニー リミテッド | Negative photosensitive resin composition |
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| CN1707358A (en) * | 2004-06-08 | 2005-12-14 | 住友化学株式会社 | Photosensitive resin composition |
| CN101535894A (en) * | 2006-11-17 | 2009-09-16 | 第一毛织株式会社 | Photosensitive resin composition for forming column spacer of liquid crystal display, method for forming column spacer using the composition, column spacer formed by the method, and display device com |
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| WO2011139111A1 (en) * | 2010-05-07 | 2011-11-10 | Rohm And Haas Electronic Materials Korea Ltd. | Resin composition, insulating film using the same, and electronic component |
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| CN111465900A (en) * | 2018-11-16 | 2020-07-28 | 株式会社Lg化学 | Photosensitive resin composition, photosensitive material, display device, and method for low-temperature curing of photosensitive resin composition |
| TWI791224B (en) * | 2021-05-26 | 2023-02-01 | 達興材料股份有限公司 | Alkali-soluble resin, protective layer composition, protective layer, laminate, and method for forming photoresist pattern |
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