CN117130224A - Positive photoresist composition for organic insulating film of liquid crystal display element - Google Patents

Positive photoresist composition for organic insulating film of liquid crystal display element Download PDF

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Publication number
CN117130224A
CN117130224A CN202311099761.2A CN202311099761A CN117130224A CN 117130224 A CN117130224 A CN 117130224A CN 202311099761 A CN202311099761 A CN 202311099761A CN 117130224 A CN117130224 A CN 117130224A
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China
Prior art keywords
parts
carbon atoms
insulating film
liquid crystal
crystal display
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CN202311099761.2A
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Chinese (zh)
Inventor
崔淑英
毕研刚
洪海哲
滕福爱
豆帆
颜俊雄
朱洪维
刘天用
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Yantai Shield Materials Technology Co ltd
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Yantai Shield Materials Technology Co ltd
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Priority to CN202311099761.2A priority Critical patent/CN117130224A/en
Publication of CN117130224A publication Critical patent/CN117130224A/en
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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
    • G02F1/1337—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers
    • G02F1/133711—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers by organic films, e.g. polymeric films
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
    • G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
    • G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
    • G03F7/0397—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition the macromolecular compound having an alicyclic moiety in a side chain
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/075—Silicon-containing compounds
    • G03F7/0755—Non-macromolecular compounds containing Si-O, Si-C or Si-N bonds
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/075—Silicon-containing compounds
    • G03F7/0757—Macromolecular compounds containing Si-O, Si-C or Si-N bonds

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  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • General Physics & Mathematics (AREA)
  • Nonlinear Science (AREA)
  • Mathematical Physics (AREA)
  • Chemical & Material Sciences (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Optics & Photonics (AREA)
  • Materials For Photolithography (AREA)

Abstract

The invention belongs to the technical field of photoresist, and in particular relates to a positive photoresist composition for an organic insulating film of a liquid crystal display element, which comprises 100 parts of binder resin with a structure shown in a general formula I or a general formula II, 2-100 parts of azo compound, 1-4 parts of photosensitizer, 0.01-3 parts of silicon-based additive, 0.1-10 parts of thermal acid generator or thermal base generator, 0.001-5 parts of surfactant, 0.001-5 parts of adhesion promoter and 200-4000 parts of solvent. The positive photoresist composition of the present invention has excellent storage stability and excellent adhesion to a resist film by adding a binder resin having a structure represented by general formula I and/or general formula II to the composition, and can be developed with an alkali developer, thereby shortening the process, and being excellent in adhesion to metals, UV transmittance, residual film rate, and pattern stability.

Description

Positive photoresist composition for organic insulating film of liquid crystal display element
Technical Field
The invention relates to a positive photoresist composition for an organic insulating film of a liquid crystal display element, belonging to the technical field of photoresists.
Background
In general, a liquid crystal display device (Liquid Crystal Display, abbreviated as LCD) is used for devices such as televisions and graphic displays, and particularly, each pixel is provided with a switching element such as a thin film transistor (Thin Film Transistor, abbreviated as TFT). An active matrix LCD has high-speed response characteristics and is suitable for a high number of pixels, and thus contributes to a display screen or the like that achieves high image quality, large size, and color, which are comparable to those of a Cathode Ray Tube (CRT).
In order to obtain a high-quality display screen in a TFT-LCD, the aperture ratio is first increased. Here, the aperture ratio refers to the actual light transmittance of the pixel electrode area. In TFT-LCDs, as the demands for their size and resolution increase, the capacity increases, but the efficiency of the battery does not keep pace, so in order to solve the decrease in battery efficiency, a method of improving the transmittance of the liquid crystal is often employed. The mode of improving the transmittance of the liquid crystal can be achieved by greatly improving the aperture ratio of the liquid crystal panel, developing a highly transparent polarizing plate or using a highly transparent color filter. In this method, a transparent Indium Tin Oxide (ITO) electrode is disposed on a TFT as a pixel electrode to increase a pixel electrode (pixel electrode) area. The mode is an epoch-making technology for improving the aperture ratio of the traditional TFT-LCD from 50-60% to about 80-85%, and can greatly reduce the reduction of the battery efficiency.
Hereinafter, in order to help understanding the high aperture ratio TFT-LCD, a detailed description will be made with reference to the accompanying drawings. Fig. 1 is a plan view of a conventional unit cell of a TFT-LCD having a high aperture ratio. As shown in fig. 1, the gate lines 2 are arranged laterally, and the storage electrode lines 4 are arranged at positions spaced apart from each other by a predetermined interval, and the data lines 8 are arranged to vertically pass through the gate lines 2 and the storage electrode lines 4. On the gate line 2 adjacent to the intersection of the gate line 2 and the data line 8, the semiconductor layer 6 is formed in a pattern, and the drain electrode 9a drawn from the data line 8 and the source electrode 9b formed together when the above-described data line 8 is formed are arranged on the semiconductor layer 6 to face each other and overlap each other. In the pixel region defined by the gate line 2 and the data line 8, a pixel electrode 12 made of ITO is arranged, and at this time the pixel electrode 12 is arranged in the entire pixel region so as to be in contact with not only the source electrode 9b but also a part of the data line 8 and the gate line 2.
FIG. 2 is a cross-sectional view taken along line II-II' of FIG. 1. As shown in fig. 2, a gate electrode 2a is formed on a lower substrate 20 and a storage electrode 4a is formed at a position spaced apart therefrom, and a gate insulating film 3 is formed in front of the lower substrate 20. Further, a semiconductor layer 6 is formed in a pattern by a known process on the gate insulating film 5 located on the upper portion of the gate electrode 2a, and a drain electrode 9a and a source electrode 9b formed together at the time of formation of the data line 8 are formed separately on the semiconductor layer 6.
An organic insulating film 10 having a low dielectric constant is coated on the front surface of the lower substrate 20 where the above-described structure is formed, and a contact hole for exposing the source electrode is provided in the organic insulating film 10, and the pixel electrode 12 is formed overlapping a portion of the gate electrode 2a and the data line 8 while a portion corresponding to the pixel region is in contact with the source electrode 9b through the contact hole.
The organic insulating film 10 serves as an insulation between the pixel electrode 12 and the data line 8, and also serves as a planarization layer between the pixel electrode and the underlying layer. Such an insulating film layer has previously used benzocyclobutene (Benzo Cyclo Butyne, BCB) to improve the aperture ratio. But benzocyclobutene is expensive and the method of manufacturing the contact hole has a problem in that a reactive ion etching (reactive ion etching, RIE) process using photoresist is necessary.
Disclosure of Invention
The present invention addresses the above-described drawbacks of the prior art by providing a positive photoresist composition for an organic insulating film of a liquid crystal display element, which has excellent storage stability and excellent adhesion to a resist film.
The technical scheme for solving the technical problems is as follows:
a positive photoresist composition for an organic insulating film of a liquid crystal display element comprises 100 parts of binder resin, 2 to 100 parts of azo compound, 1 to 4 parts of photosensitizer, 0.01 to 3 parts of silicon-based additive, 0.1 to 10 parts of thermal acid generator or thermal base generator, 0.001 to 5 parts of surfactant, 0.001 to 5 parts of adhesion promoter and 200 to 4000 parts of solvent;
the binder resin has a structure represented by the following general formula I:
wherein,
a, b, c, d are the molar ratio of each monomer, 0.ltoreq.a <1, 0.ltoreq.b <1, 0.ltoreq.c <1, 0.ltoreq.d <1, a+b+c+d=1;
x is a hydrogen atom or a methyl group;
Y 1 is an alkyl group or a hydroxyalkyl group having 1 to 15 carbon atoms;
Y 2 is an alkyl group having 1 to 15 carbon atoms and containing an epoxy group;
Y 3 is any one of the structures shown in structural formulas (I) to (VII):
in the structural formulae (I) to (VII), R 1 Is hydrogen or methyl; r is R 2 Is an olefin having 1 to 10 carbon atoms; r is R 3 Is a hydrocarbon compound having 1 to 10 carbon atoms; r is R 4 Is hydrogen or methyl;
alternatively, the binder resin has a structure represented by the following formula II:
wherein n is more than or equal to 0 and less than or equal to 3;
R 1 any one selected from hydrogen atoms, alkyl groups with 1 to 10 carbon atoms, olefins with 2 to 10 carbon atoms, and aryl-containing alkyl groups with 6 to 15 carbon atoms;
R 2 selected from any one of hydrogen atom, alkyl group having 1 to 6 carbon atoms, and aryl-containing alkyl group having 6 to 15 carbon atoms.
Based on the technical scheme, the invention can also make the following improvements:
further, the binder resin represented by the general formula I has an average molecular weight of 2000 to 50000, a dispersity of 1.0 to 5.0, and an acid value of 10 to 150KOHmg/g.
Y of the general formula I 1 As alkyl or hydroxyalkyl having 1 to 15 carbon atoms, which contributes to improved adhesion, Y 2 Unlike the acrylic copolymer resin, unlike the conventional adhesive resin, it not only increases the residual film rate including the macrocyclic structure, but also has excellent heat resistance because of a higher glass transition temperature. The binder resin represented by the general formula I preferably has a molecular weight of 2000 to 50,000, a dispersity of 1.0 to 5.0, an acid value of 10 to 150KOHmg/g, more preferably an average molecular weight of 5,000 to 20,000, a dispersity of 1.6 to 2.5, and an acidity of 50 to 130KOHmg/g, using GPC (gel dialysis chromatography) in the mobile phase and tetrahydrofuran.
Further, the binder resin represented by the general formula II has an average molecular weight of 500 to 10000.
From the viewpoint of improving the surface hardness of the cured film, the binder resin represented by the general formula ii preferably uses trifunctional silane and tetrafunctional silane to obtain an interlayer insulating film that maintains high surface hardness. The average molecular weight of the binder resin represented by the general formula II (the number of polystyrene conversions can be measured as the average molecular weight) using GPC (gel dialysis chromatography) in the mobile phase is preferably a value in the range of 500 to 10,000, more preferably a value in the range of 1,000 to 5,000. By making the average molecular weight value of the binder resin represented by the general formula II exceed 500, the film forming property of the positive-type resist composition can be improved; on the other hand, by reducing the value of the average molecular weight of the binder resin represented by the general formula II to 10,000 or less, light blocking and alkali degradation of the positive composition can be prevented.
Further, the method comprises the steps of, the azo compound is 2,2 '-azobis (2, 4-dimethyl valeronitrile), 2' -azobis (2, 4-dimethyl butyronitrile), 2 '-azobis (4-methoxy-2, 4-dimethyl valeronitrile), 2' -azobis [ N- (2-propenyl) -2-methylpropionamide ], 2 '-azobis (2-methyl butyronitrile) any one of 2,2' -azobis [2- (2-imidazolin-2-yl) propane ], 1-tris (p-hydroxyphenyl) ethane (1.0 mol) and 1, 2-naphthoquinone diazide-5-sulfonyl chloride (3.0 mol) condensate, 1-tris (p-hydroxyphenyl) ethane (1.0 mol) and 1, 2-naphthoquinone diazide-5-sulfonyl chloride (2.5 mol) condensate, the molecular weight of the azo compound is 300-1500.
The azo compound is a compound which generates carbonic acid by irradiation, and a positive photoresist composition containing the azo compound has positive optical radiation characteristics, and an exposed portion during irradiation of radiation is removed from the developing process. Further, "radiation" as referred to herein is a concept including visible light, ultraviolet light, atomic external light, X-rays, charged particle rays, and the like. As the azo compound, preferably, an anthraquinone derivative compound having a phenol compound and having a phenol ester structure obtained by halogenation of an anthraquinone dinitrate sulfonic acid can be used. On the other hand, by making the molecular weight of the azo compound 300 or more, high transparency of the interlayer insulating film can be maintained; on the other hand, by making the molecular weight of the azo compound lower than 1500, a decrease in the pattern forming ability of the positive photoresist composition can be suppressed.
Further, the photosensitizer may use a commonly used photosensitizer, and one or more of the following substances represented by formulas 3 to 11 may be selected to improve transparency:
in the above-mentioned formulae 3 to 11,
r' is a hydrogen atom or any one of the structures shown in the following structural formulas:
R 1 to R 5 Each independently selected from a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, or a cycloalkyl group having 4 to 6 carbon atoms;
R 6 、R 8 、R 10 and R is 12 Each independently selected from hydrogen atoms or alkyl groups having 1 to 6 carbon atoms;
R 7 、R 9 、R 11 and R is 13 Each independently selected from a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 4 to 6 carbon atoms, or a structure represented by the following formulas a to c:
further, the silicon-based additive is one or a mixture of more than two of (3-ethylenedioxypropyl) trimethoxysilane, (3-ethylenedioxypropyl) triethoxysilane, (3-ethylenedioxypropyl) methyldimethoxysilane, (3-ethylenedioxypropyl) dimethoxysilane, (3-ethylenedioxypropyl), 3, 4-epoxytrimethoxysilane, 3, 4-epoxybutyltriethoxysilane, 2- (3, 4-epoxychlorohexane) ethyltrimethoxysilane, 2- (3, 4-epoxysilicon) ethoxytriethoxysilane or aminopropyl trimethoxysilane.
The silicon-based additive has epoxy resin or amine group, is contained in the composition of the invention, improves the adhesion with the ITO electrode and the composition, and improves the heat resistance after curing.
Further, the thermal acid generator is an ionic compound or a nonionic compound; the ionic compound is any one or more of triphenylsulfanilamide, 1-dimethyl sulfur benzene xylene, 1-dimethyl sulfur-4-hydroxy phthalic acid ester, 1-dimethyl sulfur benzoic acid ester, 4-hydroxy benzoic acid ester, benzyl-4-hydroxy phenyl methyl sulfanilamide, 2-methylphenyl-4-hydroxy phenyl methyl sulfanilamide, 2-methyl benzyl-4-benzyl methane sulfonate, trifluoro methane sulfonate, succinic sulfonate, p-toluene sulfonate, hexafluorophosphate, benzoic acid ester and acetyl carbamate; the nonionic compound is any one or more of halogen-containing compounds, diazomethane compounds, sulfonamide compounds, sulfonate compounds, carbonate compounds and phosphate compounds.
As the halogen-containing compound, a halogen-containing hydrocarbon compound, a halogen-containing heterocyclic ring compound, or the like can be included. The halogen-containing compound is preferably 1, 1-bis (4-chlorophenyl) -2, 2-trichloroethane, 2-phenyl-4, 6-bis (trichloromethyl) -s-triene, 2-furyl-4, 6-bis (trichloromethyl) -s-triene or the like.
The dinitrogen methane compound preferably includes xylene (trifluoromethylsulfonyl) dinitrogen methane, dimethyl (cyclohexane) dinitrogen methane, xylyl dinitrogen methane, xylene (p-methanol) dinitrogen methane, dimethyl (2, 4-phospholipid) dinitrogen methane, xylene (p-chlorobenzenesulfonamide) dinitrogen methane, methylsulfonyl-p-toluene sulfonamide, cyclohexane (1, 1-dimethylethyl sulfonamide) dinitrogen methane, N-dimethylethyl sulfonamide, xylene (1, 1-dimethylethyl sulfonyl) dinitrogen methane, phenylmethane (benzoyl) dinitromethane, and the like.
The sulfonamide compound is preferably beta-ketosulfonamide compound, beta-sulfonamide compound, diphenyl sulfonamide compound and the like. Such as 4-triphenylsulfonamide, sulfathiazole, bisphenol (phenylphenyl) methane, 4-chlorophenyl-4-methylbenzene disulfonamide compounds, and the like.
The sulfonate compound is preferably an alkyl sulfonate, a haloalkylsulfonate, an aryl sulfonate or the like. Such as, for example, benzenesulfonate, methylsulfonic acid, nitrophenyl-9, 10-dioxytetraene-2-sulfonic acid, 2, 6-phenylbenzenesulfonate, and the like.
Other examples of the thermal acid generator include tetrahydrothiophene salts such as 1- (4-n-butoxynaphthalen-1-yl) tetrahydrothiophene triflate, 1- (4, 7-dibutoxy-1-naphthalenyl) tetrahydrothiophenyl triflate, and the like.
Further, the thermal alkali generating agent is one or more of metal, a compound thereof and an organic amine compound.
The metal and its complex are preferably bromide cobalt ammine perchlorate, bromobenzyl amine cobalt perchlorate, bromfentanyl propyl amine cobalt perchlorate, hexamethyl amine cobalt perchlorate, hexapropyl amine cobalt and chlorate, etc.
Thermal acid generators or thermal base generators, which can release an acid active material or a base active material as a catalyst by heating, can promote an axial reaction of components during heating by using these compounds when the components undergo polymerization and curing reactions, and can form an interlayer insulating film having good surface hardness and heat resistance. The thermal acid generator or thermal base generator does not release an acid active material or an alkali active material at a relatively low temperature (e.g., 70 to 120 ℃) during film formation of the positive photoresist composition, and releases an acid active material or an alkali active material after development at a relatively high temperature (e.g., 120 to 250 ℃) during heating.
From the viewpoint of the catalysis of the condensation and curing reaction of the binder resin represented by the general formula II, the thermal acid generator or thermal base generator is selected from benzyl-4-hydroxyphenylmethyl sulfonium hexafluorophosphate, 2-nitrobenzyl cyclohexyl carbamate, 1- (4, 7-dibutoxy-1-naphthyl) tetrahydrothiophene triflate, N- (trifluoromethylsulfonyloxy) naphthalene dicarboximide, and the like, which are particularly preferable.
Further, the surfactant is any one of a fluorine-based surfactant, an organosilicon-based surfactant, and a nonionic surfactant, and may be used alone or in combination with two or more thereof to improve the coating property and prevent the occurrence of defects.
Further, the adhesion promoter is any one or a mixture of two or more of trimethoxy silicon-based benzoic acid, gamma-methacrylic acid oxypropyl trimethoxy silane, vinyl triacetoxy silane, vinyl trimethoxy silane, gamma-isocyanate propyl triethoxy silane, gamma-glycidoxypropyl trimethoxy silane, gamma-glycidoxypropyl triethoxy silane, N-phenylaminopropyl trimethoxy silane, beta- (3, 4-epoxycyclohexyl) ethyl trimethoxy silane, so as to improve the adhesive force with a substrate.
Further, the solvent of the present invention includes a high boiling point solvent having a boiling point of 180 ℃ or more and a low boiling point solvent lower than 180 ℃ at atmospheric pressure.
The high boiling point solvent may have a boiling point of at least 180 ℃, preferably 180 ℃ to 250 ℃, more preferably 190 ℃ to 210 ℃ at atmospheric pressure. The content of the high boiling point solvent in the solvent of the present invention may be preferably 5% to 60%, more preferably 10% to 50%, and still more preferably 15% to 40% (based on the total weight of the solvent). Within the above range, a highly flat film can be produced in the process of forming a coating film. The high boiling point solvent is selected from the group consisting of gamma-butyrolactone, diethylene glycol monomethyl ether, diethylene glycol monobutyl ether, propylene glycol diacetate, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate, ethylene glycol monobutyl ether acetate, diethylene glycol diethyl ether, dipropylene glycol methyl ether acetate, N-dimethylformamide, N-methylformamide, N-methylacetamide, N-dimethylacetamide, N-methylpyrrolidone, dimethylsulfoxide, benzyl diethyl ether, dihexyl ether, ethylacetone, isopiponone, octanoic acid, 1-octanol, 1-nonanol, benzyl acetate, ethyl benzoate, diethyl oxalate, diethyl maleate, ethyl carbonate, propylene carbonate and benzyl acetate. Preferably, in terms of developing performance, it may be one or more of γ -butyrolactone, diethylene glycol monomethyl ether, diethylene glycol monobutyl ether, propylene glycol diacetate, diethylene glycol monoethyl ether acetate and diethylene glycol monobutyl ether acetate.
The low boiling point solvent is compatible with but does not react with the above-mentioned photosensitive resin composition components and has a boiling point of less than 180 ℃, preferably a boiling point of 100 ℃, and examples of the low boiling point solvent include one or more of propylene glycol monomethyl ether acetate, cyclohexanone, dipropylene glycol dimethyl ether, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol N-propyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol mono-N-propyl ether, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol dimethyl ether, tetrahydrofuran, methylethyl ether, 2-heptanone, 3-heptanone, ethyl acetate, N-propyl acetate, isopropyl acetate, N-butyl acetate, isobutyl acetate, N-pentyl formate, isopentyl acetate, N-butyl propionate, ethyl butyrate, N-propyl butyrate, isopropyl butyrate, N-butyl butyrate, N-dimethylformamide, N-dimethylacetamide, 3-methoxybutyl alcohol, and cyclopentanone.
The positive photoresist composition for an organic insulating film of a liquid crystal display element of the present invention is formed by irradiating ultraviolet rays using a mask after spin-coating on a substrate, preferably adding a solvent to have a viscosity in the range of 2 to 20cps, and forming an organic insulating film by applying the solvent. More preferably, adjusting the viscosity to 2-10cps is more advantageous for controlling the thickness of the film without pinholes after coating.
The invention has the beneficial effects that: the positive photoresist composition of the present invention has excellent storage stability and excellent adhesion to a resist film by adding a binder resin having a structure represented by general formula I and/or general formula II to the composition, and can be developed with an alkali developer, thereby shortening the process, and being excellent in adhesion to metals, UV transmittance, residual film rate, and pattern stability.
Drawings
Fig. 1 is a plan view of a unit cell of a TFT-LCD having a high aperture ratio;
FIG. 2 is a cross-sectional view of section II-II' of FIG. 1.
Detailed Description
The principles and features of the present invention are described below in connection with examples, which are set forth only to illustrate the present invention and not to limit the scope of the invention.
Synthesis of binder resin represented by general formula I
Synthesis example 1
In a three-necked flask equipped with a stirring, reflux condenser and a reactor capable of heating and cooling, 20.5 parts by mass of methacrylic acid, 9 parts by mass of glycidyl methacrylate, 43 parts by mass of styrene and 27.5 parts by mass of methyl methacrylate were added, followed by addition of 2.0 parts by mass of octyl methyl mercaptan, 3.0 parts by mass of 2,2' -azobis (2, 4-dimethylvaleronitrile) and propylene glycol monomethyl ether acetate were added to 100 parts by mass, and nitrogen gas was introduced. Thereafter, while stirring slowly, the temperature of the solution was raised to 60 ℃, and the temperature was maintained for 5 hours and polymerized to obtain a solution (copolymer) of a copolymer having an average molecular weight of 6400 and a molecular weight distribution of 2.0.
Synthesis example 2
Polymerization was performed in the same manner as in Synthesis example 1 except that a monomer mixture composed of 21 parts by mass of methacrylic acid, 15 parts by mass of glycidyl methacrylate, 43 parts by mass of styrene and 21 parts by mass of methyl methacrylate was used, to obtain a solution (copolymer) of a copolymer having a weight average molecular weight of 7800 and a molecular weight distribution of 2.0.
Synthesis example 3
Polymerization was performed in the same manner as in synthesis example 1 except that a monomer mixture composed of 21 parts by mass of methacrylic acid, 15 parts by mass of glycidyl methacrylate, 43 parts by mass of styrene and 21 parts by mass of dicyclopentanyl methacrylate was used, to obtain a solution (copolymer) of a copolymer having a weight average molecular weight of 9200 and a molecular weight distribution of 2.0.
Synthesis of binder resin represented by formula II
Synthesis example 4
In a vessel equipped with a stirrer, 161.4g of propylene glycol monomethyl ether, 128.9g of phenyltrimethoxysilane, 72.9g of tetraethoxysilane and 0.8g of aluminum isopropoxide were added, and then heated to a solution temperature of 60 ℃. After the temperature of the solution reached 60 ℃, 54g of ion-exchanged water was added, and the mixture was heated to 75 ℃ and kept for 3 hours for reaction. Subsequently, 159g of methyl orthoester was added as a dehydrating agent and stirred for 1 hour. The solution temperature was set to 40℃and the ion-exchanged water and methanol produced by hydrolytic condensation were removed by deaeration while maintaining the temperature to obtain a hydrolytic condensate (B-1), the mass fraction of solids was 40.3%, and the number average molecular weight (Mn) of the obtained hydrolytic condensate was 1500 and the molecular weight distribution (Mw/Mn) was 2.
Synthesis example 5
Into a vessel equipped with a stirrer, 139.4g of diacetone alcohol was added, 128.9g of phenyltrimethoxysilane and 47.7g of methyltrimethoxysilane were added, and then stirred at room temperature. Subsequently, an aqueous oxalic acid solution in which 0.18g of oxalic acid was dissolved was added to 54g of ion-exchanged water, and then heated to a solution temperature of 75 ℃. After the solution temperature reached 75 ℃, the reaction was carried out for 3 hours. Subsequently, 159g of methyl orthoester was added as a dehydrating agent and stirred for 1 hour. In addition, methanol produced during the hydrolysis of ionized water and methanol produced by condensation at a solution temperature of 40℃were subjected to vacuum distillation to obtain a hydrolysis condensate (B-2). The mass fraction of the solid was 40.5%, and the number average molecular weight (Mn) of the resulting hydrolyzed condensate was 1600, and the molecular weight distribution (Mw/Mn) was 2.
Synthesis example 6
In a vessel equipped with a stirrer, 139.4g of diacetone alcohol, 128.9g of phenyltrimethoxysilane and 47.7g of methyltrimethoxysilane were added and stirred at room temperature. Subsequently, an aqueous phosphoric acid solution in which 0.18g of phosphoric acid was dissolved was dropped into 54g of ion-exchanged water, and then heated to a solution temperature of 75 ℃. After the solution temperature reached 75 ℃, it was maintained for 3 hours. Subsequently, 159g of methyl orthoester was added as a dehydrating agent and stirred for 1 hour. Further, the solution temperature was set to 40℃and by deaeration while maintaining the temperature, ion-exchanged water and methanol produced by hydrolytic condensation were removed to obtain a hydrolytic condensate (B-3). The mass fraction of the solid was 40.5%, and the number average molecular weight (Mn) of the resulting hydrolyzed condensate was 1700, and the molecular weight distribution (Mw/Mn) was 2.
Component examples of Positive Photoresist composition
The ingredients and comparisons used to prepare the example compositions are as follows.
< A > binder resin represented by formula I
A-1: synthesis example 1
A-2: synthesis example 2
A-3: synthesis example 3
< B > binder resin represented by formula II
B-1: synthesis example 4
B-2: synthesis example 5
B-3: synthesis example 6
< C > azo Compounds
C-1: condensate with 1, 1-tris (p-hydroxyphenyl) ethane (1.0 mol) and 1, 2-naphthoquinone diazide-5-sulfonyl chloride (3.0 mol)
C-2: condensate with 1, 1-tris (p-hydroxyphenyl) ethane (1.0 mol) and 1, 2-naphthoquinone diaza-5-sulfonyl chloride (2.5 mol).
< D > thermal acid generator or thermal base generator
D-1: benzyl-4-hydroxyphenylmethyl sulfonium hexafluorophosphate
D-2: 2-nitrobenzyl cyclohexyl carbamate
D-3:1- (4, 7-dibutoxy-1-naphthyl) tetrahydrothiophene triflate
D-4: n- (trifluoromethylsulfonyloxy) naphthalene dicarboximide (manufactured by NAI-105,Midori Chemical Co., ltd.)
< E > surfactant
FZ-2122, dow-Corning Toray Co
FTX-218, NEOS Co
< F > silicon-based additives
Gamma-isocyanate propyltriethoxysilane, a product of Shin-Etsu Co
< G > solvent
< G-1>: propylene glycol monomethyl acetate, product of TCI company (boiling point about 146 ℃ C.)
< G-2>: diethylene glycol monoethyl ether, product of TCI company (boiling point about 202 ℃ C.)
< G-3>: diethylene glycol monoethyl ether acetate, product of TCI company (boiling point about 214 ℃ C.)
Example 1
70 parts of a binder resin A-1, 30 parts of a binder resin B-1, 15 parts of an azo compound [1, 1-tris (p-hydroxyphenyl) ethane (1.0 mol) and a condensate of 1, 2-naphthoquinone diazide-5-sulfonyl chloride (3.0 mol) ], 5 parts of a thermal acid generator (benzyl-4-hydroxyphenylmethyl sulfonium hexafluorophosphate), 5 parts of a fluorine-based surfactant (NEOS Co., FTX-218), and 2.0 parts of gamma-isocyanate propyltriethoxysilane were added, and the mixture was stirred at room temperature for 2 hours to give a solid concentration of 20% (mass fraction) by adding propylene glycol monomethyl ether, to prepare a positive resist composition.
Preparation of examples 2 to 11 and comparative examples 1 to 2
Other procedures were performed according to the formulations in tables 1-2 to prepare positive photoresist compositions in the same manner as in example 1.
In the comparative example, a positive resist composition for an organic insulating film of a high aperture ratio liquid crystal display element was produced in the same manner except that the binder resin (average molecular weight 10000) represented by the following formula 12 was used instead of the binder resin of example 1, and the components and content of the composition were changed according to the composition described in table 2 below.
In the above formula 12, p is 0.3, q is 0.2, and r is 0.5.
Performance testing
The positive photoresist compositions of examples 1 to 11 and comparative examples 1 to 2 were subjected to performance test, and various characteristics of the compositions, interlayer insulating films and liquid crystal cells were evaluated as follows.
1. Evaluation of radiation sensitivity of positive-working photoresist composition
After each composition was applied on a silicon substrate from examples 1 to 11 and comparative examples 1 to 2, respectively, using a rotary hopper, it was prebaked on a hot plate at 100℃for 2 minutes to form a film having a thickness of 1.5. Mu.m. For the obtained film, a Canon PLA.+ -. 501F exposure device (ultra-high pressure mercury lamp) was used to put a silicon waferThe patterning ability of the positive photoresist was adjusted by changing the exposure time under a mask having a 3.0 μm line width pattern, and the exposed portion was removed by washing in a 2.38 mass% tetramethylammonium hydroxide (TMAH) solution at 25 ℃ for 80 seconds. Then, the substrate was washed under ultrapure water for 1 minute, dried, and patterned on the silicon substrate. At this time, the spatial line width (low portion) was 0.30 μm to measure the minimum exposure amount required, and the radiation sensitivity was as shown in Table 1. When the minimum exposure is less than 200 (J/m) 2 ) When the radiation sensitivity is good, it can be said.
2. Refractive index evaluation of interlayer insulating film
A cured film was formed on a silicon substrate, the refractive index of the cured film was obtained, and the cured film was measured at 633nm using Auto EL IV NIR iii. When the refractive index is higher than 1.50, the material is considered to be useful as an interlayer insulating film.
3. Evaluation of Heat resistance of interlayer insulating film
A cured film was formed on a silicon substrate, and the film thickness (T2) of the obtained cured film was measured. Then, the silicon substrate forming the cured film was further baked at 240℃in a clean oven, and then the film thickness of the cured film was measured (T2), and by further baking, the film thickness change rate { (T2-T2)/T2 } ×100% was calculated. The results are shown in tables 1 and 2. When this value is 3% or less, heat resistance is good.
4. Evaluation of transmittance of interlayer insulating film
A thin film was formed on a glass substrate in the same manner as the above-described "evaluation of radiation sensitivity". On the obtained film, canon PLA.+ -. 501F exposure devices (ultra-high pressure mercury lamps) were used respectively to give a cumulative exposure of 3000J/m 2 After exposure, the cured film was obtained by heating at 220℃for 1 hour in a clean oven. The transmittance of the glass substrate having such a cured film was measured in a wavelength range of 400 to 800nm using a spectrophotometer "TU-1810" (manufactured by Beijing General Analytical Instrument Co.). The results are shown in tables 1 and 2. When the minimum light transmittance exceeds 95%, the light transmittance is good.
5. Evaluation of resist stripping solution resistance of interlayer insulating film resin
The following evaluation of resist stripping liquid properties of an interlayer insulating film was performed according to the following procedure
(1) Formation of cured film
First, a cured film is formed on a silicon substrate.
(2) ITO film formation on cured film
Using Japanese high-speed sputtering apparatus [ SH-550-C12 ]]ITO target (ITO charge rate 95% or more, in 2 O 3 /SnO 2 =90/10 mass ratio), ITO sputtering was performed at 60 ℃. The atmosphere at this time was such that the degree of pressure reduction was 1.0X10 -5 Pa, ar gas flow rate is 3.12X10 -3 m 3 /Hr，O 2 The gas flow rate was 1.2X10 -5 m 3 The sputtered substrate was heated at 240℃for 60 minutes in a clean oven and cured.
(3) Forming resist patterns on ITO film
The substrates were placed on a rotating jacket, and the positive photoresists of the examples and comparative examples were dropped on the substrates and coated at 3500rpm for 30 seconds. The substrate was heated on a hot plate at 90 ℃ for 2 minutes to remove the solvent. Then, using Canon PLA501F exposure apparatus (manufactured by Canon Co., ltd.) at 23mW/m 2 Exposure of 25mJ/m 2 The exposure amount of (a) was converted into i-line, and g, h, i-line (intensity ratio of wavelengths 436nm, 405nm, 365 nm=2.7:2.5:4.8) was irradiated through a pattern mask. Then, the mixture was immersed in 2.38% TMAH aqueous solution at 25 ℃ for 60 seconds, rinsed in ultrapure water for 60 seconds, and then air-dried. A resist pattern having a line width of 10 μm/10 μm was formed.
(4) Etching of ITO film
As the etching solution, a mixture of nitric acid and hydrochloric acid was used in a weight ratio of 1/3. And (3) immersing and etching the substrate in the step (3) for 60 seconds, and etching the ITO film without the resist.
6. Evaluation of Dry etching resistance of interlayer insulating film
A cured film was formed on a silicon substrate in the same manner as the positive photoresist composition, and a dry etching apparatus CDE-80N (manufactured by Shibaura Mechatronics co., ltd.) was used to etch the gas CF 4 50 mL/min of the total volume of the solution,O 2 the dry etching was performed at 10 mL/min with an output of 400mW and an etching time of 90 seconds, and the film heads before and after the treatment were measured. The results are shown in tables 1 and 2. When the film thickness is reduced by less than 1.0 μm, the dry etching property is good.
Table 1 examples and physical property test tables thereof
Table 2 comparative examples and physical properties test table thereof
From the results shown in Table 1, the cured film formed from the positive photoresist composition of the present invention uses the binder resin, thermal acid generator or thermal base generator and other auxiliary agents having the structures shown in the general formula I and/or the general formula II, and has the characteristics of good heat resistance, high transmittance and good dry etching property as compared with the positive photoresist composition formed from the binder resin having the structure shown in the general formula 12 in Table 2. The positive photoresist composition of the present invention has excellent heat resistance when forming an insulating film, and also has excellent adhesion to metals and inorganic substances, ultraviolet ray permeability, film residue, flatness and pattern stability. Thus, by changing the structure and composition ratio of the binder resin, an organic insulating film composition for a liquid crystal marking element with an adjustable high aperture ratio can be obtained using the positive photoresist composition of the present invention.
The foregoing description of the preferred embodiments of the invention is not intended to limit the invention to the precise form disclosed, and any such modifications, equivalents, and alternatives falling within the spirit and scope of the invention are intended to be included within the scope of the invention.

Claims (10)

1. A positive photoresist composition for an organic insulating film of a liquid crystal display element is characterized by comprising, by mass, 100 parts of a binder resin, 2-100 parts of an azo compound, 1-4 parts of a sensitizer, 0.01-3 parts of a silicon-based additive, 0.1-10 parts of a thermal acid generator or thermal base generator, 0.001-5 parts of a surfactant, 0.001-5 parts of an adhesion promoter and 200-4000 parts of a solvent;
the binder resin has a structure represented by the following general formula I:
wherein,
a, b, c, d are the molar ratio of each monomer, 0.ltoreq.a <1, 0.ltoreq.b <1, 0.ltoreq.c <1, 0.ltoreq.d <1, a+b+c+d=1;
x is a hydrogen atom or a methyl group;
Y 1 is an alkyl group or a hydroxyalkyl group having 1 to 15 carbon atoms;
Y 2 is an alkyl group having 1 to 15 carbon atoms and containing an epoxy group;
Y 3 is any one of the structures shown in structural formulas (I) to (VII):
in the structural formulae (I) to (VII), R 1 Is hydrogen or methyl; r is R 2 Is an olefin having 1 to 10 carbon atoms; r is R 3 Is a hydrocarbon compound having 1 to 10 carbon atoms; r is R 4 Is hydrogen or methyl;
and/or the binder resin has a structure represented by the following general formula II:
wherein n is more than or equal to 0 and less than or equal to 3;
R 1 any one selected from hydrogen atoms, alkyl groups with 1 to 10 carbon atoms, olefins with 2 to 10 carbon atoms, and aryl-containing alkyl groups with 6 to 15 carbon atoms;
R 2 selected from any one of hydrogen atom, alkyl group having 1 to 6 carbon atoms, and aryl-containing alkyl group having 6 to 15 carbon atoms.
2. The positive resist composition for an organic insulating film for a liquid crystal display element according to claim 1, wherein the binder resin represented by the general formula I has an average molecular weight of 2000 to 50000, a dispersity of 1.0 to 5.0, and an acid value of 10 to 150KOHmg/g.
3. The positive resist composition for an organic insulating film of a liquid crystal display element according to claim 1, wherein the binder resin represented by the general formula II has an average molecular weight of 500 to 10000.
4. The positive photoresist composition for an organic insulating film of a liquid crystal display element according to claim 1, wherein, the azo compound is 2,2 '-azobis (2, 4-dimethyl valeronitrile), 2' -azobis (2, 4-dimethyl butyronitrile), 2 '-azobis (4-methoxy-2, 4-dimethyl valeronitrile), 2' -azobis [ N- (2-propenyl) -2-methylpropionamide ], any one of 2,2 '-azobis (2-methylbutyronitrile), 2' -azobis [2- (2-imidazolin-2-yl) propane ], 1-tri (p-hydroxyphenyl) ethane and 1, 2-naphthoquinone diazide-5-sulfonyl chloride condensate, the molecular weight of the azo compound is 300-1500.
5. The positive resist composition for an organic insulating film of a liquid crystal display element according to claim 1, wherein the photosensitive agent is selected from one or more of the following substances represented by formulas 3 to 11:
in the above-mentioned formulae 3 to 11,
r' is a hydrogen atom or any one of the structures shown in the following structural formulas:
R 1 to R 5 Each independently selected from a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, or a cycloalkyl group having 4 to 6 carbon atoms;
R 6 、R 8 、R 10 and R is 12 Each independently selected from hydrogen atoms or alkyl groups having 1 to 6 carbon atoms;
R 7 、R 9 、R 11 and R is 13 Each independently selected from a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 4 to 6 carbon atoms, or a structure represented by the following formula a, formula b, or formula c:
6. the positive resist composition for an organic insulating film of a liquid crystal display element according to claim 1, wherein the silicon-based additive is one or a mixture of two or more of (3-ethylenedioxypropyl) trimethoxysilane, (3-ethylenedioxypropyl) triethoxysilane, (3-ethylenedioxypropyl) methyldimethoxysilane, (3-ethylenedioxypropyl) dimethoxysilane, (3-ethylenedioxypropyl) 3, 4-epoxytrimethoxysilane, 3, 4-epoxybutyltriethoxysilane, 2- (3, 4-epoxychlorohexane) ethyltrimethoxysilane, 2- (3, 4-epoxysilicon) ethoxytriethoxysilane, or aminopropyl trimethoxysilane.
7. The positive resist composition for an organic insulating film of a liquid crystal display element according to claim 1, wherein the thermal acid generator is an ionic compound or a nonionic compound; the ionic compound is any one or more of triphenylsulfanilamide, 1-dimethyl sulfur benzene xylene, 1-dimethyl sulfur-4-hydroxy phthalic acid ester, 1-dimethyl sulfur benzoic acid ester, 4-hydroxy benzoic acid ester, benzyl-4-hydroxy phenyl methyl sulfanilamide, 2-methylphenyl-4-hydroxy phenyl methyl sulfanilamide, 2-methyl benzyl-4-benzyl methane sulfonate, trifluoro methane sulfonate, succinic sulfonate, p-toluene sulfonate, hexafluorophosphate, benzoic acid ester and acetyl carbamate; the nonionic compound is any one or more of halogen-containing compounds, diazomethane compounds, sulfonamide compounds, sulfonate compounds, carbonate compounds and phosphate compounds.
8. The positive resist composition for an organic insulating film of a liquid crystal display element according to claim 1, wherein the thermal alkali generator is one or more of a metal, a complex thereof, and an organic amine compound.
9. The positive photoresist composition for an organic insulating film of a liquid crystal display element according to claim 1, wherein the surfactant is any one of a fluorine-based surfactant, a silicone-based surfactant, and a nonionic surfactant.
10. The positive resist composition for an organic insulating film of a liquid crystal display element according to claim 1, wherein the adhesion promoter is any one or a mixture of two or more of trimethoxysilylbenzoic acid, gamma-oxypropyltrimethoxysilane, vinyltriacetoxysilane, vinyltrimethoxysilane, gamma-isocyanatopropyltriethoxysilane, gamma-glycidoxypropyl trimethoxysilane, gamma-glycidoxypropyl triethoxysilane, N-phenylaminopropyl trimethoxysilane, beta- (3, 4-epoxycyclohexyl) ethyltrimethoxysilane.
CN202311099761.2A 2023-08-29 2023-08-29 Positive photoresist composition for organic insulating film of liquid crystal display element Pending CN117130224A (en)

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