WO2000058788A1 - Article multicouche photopolymerisable haute definition et dispositif semiconducteur fabrique avec cet article - Google Patents

Article multicouche photopolymerisable haute definition et dispositif semiconducteur fabrique avec cet article Download PDF

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Publication number
WO2000058788A1
WO2000058788A1 PCT/JP2000/001814 JP0001814W WO0058788A1 WO 2000058788 A1 WO2000058788 A1 WO 2000058788A1 JP 0001814 W JP0001814 W JP 0001814W WO 0058788 A1 WO0058788 A1 WO 0058788A1
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photopolymerizable
weight
film
resin
molecular weight
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PCT/JP2000/001814
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English (en)
Japanese (ja)
Inventor
Koichi Fujishiro
Shinji Inaba
Shinsuke Okita
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Nippon Steel Chemical Co., Ltd.
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Publication of WO2000058788A1 publication Critical patent/WO2000058788A1/fr

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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
    • 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

Definitions

  • the present invention is suitable for a solder resist, a plating resist, an etching resist for forming a circuit board, an insulating film for multilayering a wiring board on which a semiconductor element is mounted, and a photosensitive adhesive. It relates to a photopolymerizable laminate that can be re-developed. Further, the present invention relates to a semiconductor device using the same, and a display component such as a power filter and a spacer which contribute to an increase in the size of a liquid crystal display or a plasma display.
  • DFR dry phenolic resist
  • a support layer and a photopolymerizable layer has been used as a resist for circuit creation.
  • DFR is generally prepared by laminating a photopolymerizable composition on a supporting film, and in many cases, further laminating a protective film on the composition.
  • an aluminum development type using a weak aqueous solution as a developer is generally used as a material for such a photopolymerizable layer.
  • a printed circuit board using DFR first peel off the protective film, then use a laminator or the like to laminate DFR on a permanent circuit board such as a copper-clad laminate, Exposure is performed through a pattern mask or the like. Next, the non-exposed portion of the photopolymerizable composition is dissolved or dispersed and removed with a developing solution, and is hardened on a substrate. To form a resist image. Thereafter, the metal surface of the substrate is subjected to etching or plating treatment using the formed resist image as a mask, and then the resist image is peeled off using an aqueous solution of an alkaline solution stronger than the developing solution. A printed wiring board is formed. Therefore, the cured film is required to have strong film strength and flexibility. On the other hand, since DFR is stored in a three-layer roll state, a phenomenon such as a so-called cold flow that the photopolymerizable layer protrudes from the end face during storage may occur. Not preferred.
  • the adhesiveness is poor when the photopolymerizable layer is laminated on a substrate, and the photopolymerizable layer cannot fill the unevenness on a substrate having unevenness.
  • a space may be created between the photopolymerizable layer and the substrate. When such a space is formed, the etching liquid or the plating liquid penetrates into the substrate, thereby causing defects such as disconnection or short circuit.
  • the photopolymerizable layer of DFR widely used at present has (1) a thermoplastic organic polymer binder, (2) at least one ethylenic group, and a polymer can be formed by a photopolymerization initiator. It is composed of a composition comprising an unsaturated compound, (3) a photopolymerization initiator, and (4) other additives. All of the thermoplastic organic polymer binders are vinyl copolymerized with several monomers having one ethylenic group in the molecule (at least one of which contains a carboxyl group). It is a system copolymer resin.
  • the polymer chain in the resin is composed of carbon-carbon bonds, and a carboxyl group, an ester thereof, or an aromatic compound is bonded as a side chain thereof.
  • Specific examples include copolymers of methacrylic acid and its esters and styrene derivatives.
  • unsaturated compound aliphatic polyhydric alcohols, acrylic acid and methacrylate, are the most common, and trimethylolpropane triacrylate is most commonly used. It is known to have at least two unsaturated groups, such as acrylate, dipentaerythrene hexaacrylate, pentaerythrate monoacrylate, polyethylene diol glycol diacrylate, and the like. .
  • thermoplastic organic polymer binder The role of the thermoplastic organic polymer binder is responsible for the film forming properties at room temperature, the flexibility as a film, and the solubility in an alkaline developer.
  • the structure of the binder relating to these properties is widely defined as a weight average molecular weight of 20,000 to 600,000 and an acid value of 100 to 600. In general, when the molecular weight is less than 20,000, the cold flow and cut-chip properties are degraded, and when the molecular weight is as large as over 600,000, poor development and a decrease in substrate followability during heat lamination are observed. Therefore, a molecular weight range that optimizes the properties as DFR has been tried for each resin composition.
  • JP-A-89-918 and the like two types of binders having a high molecular weight and a lower molecular weight are mixed to achieve both film characteristics and developing characteristics.
  • the unsaturated compound plays a role of forming a crosslinked structure upon exposure and insolubilizing the film in an alkaline developer to form a pattern.
  • compounds having a carboxyl group and an acryloyl group in one molecule are used in combination. Together with the above role, it promotes reduction of development and photocurability.
  • This is a compound with a molecular weight of less than 2000, which is obtained by simply adding monoanhydride to an epoxy resin and an acrylic acid reactant.To increase the molecular weight, only Novolac type epoxy resin is used. Carbon-carbon bond, and ether bond by self-condensation of epoxy resin.
  • Ethylene dalycol chains and Z or propylene glycol chains in various molecules Reports using a combination of polyfunctional acrylates and urethane acrylates, for example, Japanese Patent Application Laid-Open Nos. Hei 7-1991-153, Japanese Patent Application Laid-Open No. 9-190628, Japanese Patent Application Laid-Open No. 2-2 DFR can be used in Japanese Patent Application Laid-Open No. 697172, Japanese Patent Application Laid-Open No. 2-33253, Japanese Patent Application Laid-Open No. 11271744, Japanese Patent Application Laid-Open No. Flexibility, followability during lamination, adhesion to the substrate, and tending strength.
  • Japanese Patent Application Laid-Open No. 1-219734 discloses a polyfunctional acrylate having an acryloyl group in a dipentaerythr skeleton via a force prolacton chain (for example, Pharmaceutical DPCA-60, DPCA-120 etc.) can reduce the DFR tackiness without reducing the cross-linking property during exposure.
  • these unsaturated compounds are low-molecular-weight compounds having a molecular weight of 2000 or less, and play a role of a plasticizer of a thermoplastic organic polymer binder as a main component, thereby improving the flexibility of DFR. Is what it is.
  • thermoplastic organic polymer binder various physical properties are also adjusted by the mixing ratio of the thermoplastic organic polymer binder and the unsaturated compound.
  • the mixing ratio of the binder may be reduced. However, this causes a delay in development time due to cold flow, a decrease in the acid value of the coating film, and poor development.
  • the photopolymerizable layer described above is peeled off after use as a resist.However, unlike these, the photopolymerizable layer is used as a permanent protective film by utilizing the physical properties of the cured film.
  • a photopolymerizable layer is provided with heat resistance after curing and used as a solder resist.
  • HEI 3-11211-54 and H08-2888645 an acid anhydride adduct of a novolac-type epoxy compound and an acrylic acid reactant is used to form an acid anhydride.
  • an imageable resin and make it a DFR There is a proposal to use it as an imageable resin and make it a DFR.
  • this resin also has a low molecular weight and is connected by a cresol novolak type methylene group, it is doubtful whether DFR is possible. In the former, there is no description about DFR in the examples.
  • multilayering has been promoted as a further high-density mounting substrate, and the correlated insulating film or the passivation film constituting the wiring substrate on which this is mounted has heat resistance. Low dielectric constant, low water absorption, low coefficient of thermal expansion, high adhesion, and good chemical resistance are required.
  • the material itself has been developed so that the via hole can be formed by a process similar to the photo resist. It is preferred to have photosensitivity.
  • polyimide resin for example, JP-A-5-165217
  • organic silicon resin for example, JP-A-3-43435
  • benzocyclobutene resin for example, Japanese Patent Publication No. 7-19773
  • heat-resistant epoxyacrylate resin for example, No. 1 214141
  • Both polyimide resin and organosilicon resin have difficulty in forming high-precision and fine via-holes, so there is a limit to high density, and the curing temperature is more than 300 ° C. And high temperature, subject to the restrictions of the substrate.
  • examples in which these are converted to DFR can only be found in polyimide resins, which are also in the state of polyamic acid, which is a polyimide precursor, and the polymer main chain is composed of amide bonds. Have been.
  • PCTZ JP 93/050536, JP-A-5-146132 and JP-A-8-1463111 disclose epoxyacrylate and acid diacid.
  • An adduct with an anhydride is exemplified, but there is no description of DFR conversion and no description of its DFR properties.
  • the present invention uses a vinyl copolymer as a conventional DFR to prevent cold flow by increasing its molecular weight, to improve film flexibility and strength, and to reduce lamination by reducing the molecular weight. It is an object of the present invention to provide a photopolymerizable laminate that solves the problem of achieving contradictory characteristics such as the ability to follow the substrate at the time and the good developability. Further, the present invention provides a register, an image forming material, and the like having a higher resolution than those of the related art. Furthermore, an object of the present invention is to provide a high-density, high-performance semiconductor device or display device because the cured product is excellent in heat resistance and the like.
  • the present inventors have conducted intensive studies to achieve the above object, and as a result, have found that a polyester-based copolymer having a completely different bonding system from the main chain formed by carbon-carbon bonds found in conventional vinyl-based copolymers. This problem has been solved by using a photopolymerizable layer in which is used as a binder.
  • the present invention provides a photopolymerizable laminate having a photopolymerizable layer and a support layer, wherein the photopolymerizable layer is
  • the present invention is a semiconductor device or a liquid crystal device, wherein the photopolymerizable laminate is laminated, and a cured film thereof is formed as a permanent film.
  • the diol compound to be reacted with an acid dianhydride to obtain a carboxyl group-containing copolymer has two hydroxyl groups in the molecule and two diols in the acid dianhydride from the viewpoint of increasing the molecular weight during the polymerization reaction.
  • Those having the same reactivity with two acid anhydride groups, for example, those having a symmetric molecular structure are preferred.
  • this diol compound examples include ethylene diol, diethylene glycol, polyethylene glycol, propylene glycol, hydrogenated bisphenol A, and bis (4-hydroxyphenyl) ketone. Tonone, bis (4-hydroxyphenynole) sunorehon, 2,2-bis (4-hydroxyphenynole) prono ,.
  • the acrylic acid adduct has a polymerizable unsaturated group and an alkali-soluble carboxyl group in the same molecule after the reaction with the acid dianhydride, and is therefore preferable for improving the exposure sensitivity and increasing the resolution.
  • preferred diol compounds include: There is a compound represented by the formula (1)
  • R i R s independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
  • Examples of the acid dianhydride used for the reaction with the diol compound ′ in the present invention include pyromellitic anhydride, benzophenonetetracarboxylic acid, and the like. Dianhydride, biphenylenolete tricarboxylic dianhydride, biphenylenoleatenoletetracarboxylic dianhydride, diphenylsulfone tetracarboxylic dianhydride, ethylene glycol monolevis trimethylate And methynolecyclohexene dicarboxylic anhydride.
  • the acid dianhydride in the present invention includes carboxylic acid derivatives having the same effect, that is, carboxylic acid esters and acid halides.
  • the acid dianhydride is 100 moles based on the diol compound. /. It is synthesized with a reaction charge ratio of less than.
  • the charge ratio of the acid dianhydride is 100 mol% or more, it is not easy to control the molecular weight of the obtained copolymer, and the photopolymerizable layer composition prepared from the obtained copolymer is difficult to control. Lack of storage stability.
  • the charge ratio of the acid dianhydride is preferably 5 ° mol to the diol compound in order to satisfy the desired DFR characteristics.
  • the unreacted diol compound and the compound in which one hydroxy group has reacted coexist with the carboxyl group-containing copolymer, but these are usually separated without separation in the photopolymerizable layer. used.
  • the content of the unreacted diol compound is less than 30% by area in the GPC analysis described later.
  • the weight average molecular weight of the above-mentioned carboxyl group-containing copolymer is not less than 3,000 and less than 40,000.
  • the molecular weight is determined as polystyrene by gel permeation chromatography (GPC) using tetrahydrofuran as a developing solvent. If the weight-average molecular weight exceeds 40,000, developability and resolution decrease, and if it is less than 3,000, the viscosity of the photopolymerizable layer decreases, so that cold flow is likely to occur and the cut-chip property deteriorates. I do. This best The molecular weight range is lower than that of the conventional vinyl copolymer, and it is considered that the resin of the present invention is based on a polyester / polyester resin.
  • the carboxyl group-containing copolymer has an acid value of 50 to 200 mgKOH / g, preferably 70 to 170 mgKOH / g.
  • the acid value is expressed by the number of milligrams of the hydration power required to neutralize 1 g of resin.
  • the individual acid value of the carboxyl group-containing copolymer differs depending on the polymer end, but the difference decreases with an increase in the degree of polymerization. Further, since the copolymer is obtained as a mixture containing the unreacted diol as described above, the measured acid value of the mixture may be approximated to the acid value of the carboxyl group-containing copolymer.
  • the acid value is less than 50 mgKOH / g, the development time is prolonged, and when it exceeds 200 mgKOH / g, the fine pattern is easily peeled off during development.
  • the carboxyl group-containing copolymer used in the present invention has good resolution and high-speed developability even when used alone, but has a weight average molecular weight of 3,000 to 7,000 and 7,000. , 000 to 400, 000, a more rapid development process is possible.
  • the carboxyl group-containing copolymer used in the present invention has a good alcoholic developability and a good copolymer despite its low molecular weight and acid value as compared with the conventional biel copolymer-based alkaline developable binder. It is possible to obtain a flexible film with no flow. The reason for this is that since the main chain of this copolymer is composed of ester bonds, it is a flexible film that has a lower degree of polymerization but has no cold flow as compared with the Bull copolymer.
  • the DFR has unprecedented characteristics, in that it has a relatively low molecular weight, enabling rapid development.
  • the component (B) of the present invention comprises a photopolymerizable ethylenic group, preferably a terminal ethylene group.
  • unsaturated compounds known compounds that have been used in DFR can be used. Specific examples include those obtained by combining a polyhydric alcohol and a monounsaturated carboxylic acid, such as diethylene glycol (meth) acrylate (diata acrylate or dimethacrylate). Triglycerol glycol (meta) acrylate, tetraethylene glycol (meta) atalylate, trimethylolpropane (meta) acrylate Rate, trimethylol prono ,. Nji
  • Metal acrylate, trimethylolpropane tri (meta) acrylate, 1,3-pronondiol (meta) acrylate, 1,3-butanediol
  • the unsaturated compound (B) is used in an amount of 25 to 180 parts by weight, preferably 30 to 150 parts by weight, based on 100 parts by weight of the carboxyl group-containing copolymer resin as a binder. . If the amount is less than 25 parts by weight, fine patterns are likely to flow during alkaline development, and the plating liquid resistance is poor. If the amount exceeds 180 parts by weight, cold flow during storage of DFR tends to occur, and the adhesion between the cured film and the substrate is poor.
  • Examples of the photopolymerization initiator (C) that can be used in the present invention include known initiators that are activated by various actinic rays, for example, ultraviolet rays, and start polymerization.
  • Examples of such photopolymerization initiators include acetophenone, 2,2'-diethoxysetphenone, p-dimethylacetophenone, and p-tert-butylacetophenone.
  • Benzoin ethers such as 2-methyl-1- [4- (methylthio) phenyl] -12-monforinopropanone-1,1,2-benzyl-2-dimethylamino-1- (4 —Mono ⁇ -Aminoalkylphenones such as folinophenyl) -butanone-1, bis (2,4,6-trimethylbenzoinole) phenylphosphine-oxide and glycines such as ⁇ -phenyldaricin , 2,4-Trichloromethyl-1- (pipyronyl) -16-triazine, 2,4-Trichloromethinole-1 (4,1-methoxytolyl) -16-Triazine And triazines such
  • the amount of the photopolymerization initiator (C) contained in the photopolymerizable layer of the present invention depends on the amount of the component ( ⁇ ) And 0.1 to 15% by weight based on the total amount of component (B).
  • the amount of the photopolymerization initiator is less than 0.1% by weight, the sensitivity of the exposed portion is not sufficient, and the weight is 15% by weight. /. If used in excess of this, there is no effect on improving sensitivity, absorption of actinic light increases, curing at the bottom of the photopolymerizable layer becomes insufficient, and the pattern shape after development becomes an undesired tape.
  • the diol compound which is a raw material component of the carboxyl group-containing copolymer in the present invention has two or more polymerizable unsaturated groups in one molecule
  • a highly sensitive photopolymerizable layer can be obtained.
  • the carboxyl group containing carboxyl group and the unsaturated group forming a crosslinked structure by light irradiation coexist in the carboxyl group-containing copolymer, and a large amount of unsaturated groups in one molecule by copolymerization. Since the group is introduced, it is possible to form a highly sensitive photopolymerizable layer that is insolubilized even with a small amount of light irradiation.
  • the photopolymerizable layer containing the above (A) to (C) as essential components is capable of forming tape-shaped patterns with excellent resolution that is not available in conventional DFR, and is a high-density, high-definition device. I will provide a.
  • the carboxyl group-containing copolymer of the present invention can be prepared, for example, by reacting the diol compound and the acid dianhydride in a solvent having a boiling point of 100 ° C. or higher in the presence of a known catalyst at 60 to 130 ° C. It is obtained as a resin solution by heating at C for 2 to 20 hours. It is suitable that the reaction solvent has no hydroxyl group and has a boiling point higher than the reaction temperature, for example, ethynorecello-solozoleviacetate, propylene glycol cornolemonomethionolate.
  • J / 114 Ether, ester, and ketone solvents such as ether acetate, diglyme, ethyl carbitol acetate, silk hexanone, and diisobutyl ketone are preferably used.
  • the reaction may also be used in ⁇ . 0 0 range from 1 to 1 weight 0/0 catalyst purposes against the diol of compound that promotes.
  • a known catalyst such as tetraethylammonium bromide can be used.
  • a polymerization inhibitor such as di-t-butylhydroxytoluene may be added in a range of 0.1% by weight or less based on the diol compound. ,.
  • Carboxyl group-containing copolymer were charged acid dianhydride in the synthesis is carried out in 1 0 less than 0 mole 0/0 of the charge Jio Le compounds. If the charge is 100 mol% or more, it is not easy to control the molecular weight of the obtained copolymer, and the photopolymerizable layer composition prepared from the obtained copolymer lacks storage stability. Further, the diol compound and the acid dianhydride used in the copolymerization are not limited to one kind, and a copolymer may be used by using two or more kinds. Furthermore, an acid monoanhydride or a monofunctional hydroxy compound may be used in combination for capping the terminal of the copolymer.
  • the polymer having a relatively low weight-average molecular weight of 3,000 to 7,0,0 is preferred. It is suitable for obtaining 100 copolymers.
  • acid monoanhydride is used for terminal blocking, the amount charged is 5 mol% or less of acid dianhydride, and the sum of 2 times mol of acid monoanhydride and the number of moles of acid dianhydride Should not exceed the number of moles of the diol compound.
  • monofunctional human Doroki shea compound endcapping is 5 0 mole 0 / the charged amount of the diol compound. It is as follows.
  • Suitable examples of such an acid monoanhydride are used, and examples thereof include phthalic anhydride, tetrahydrophthalic anhydride, and methylcyclohexyldicarboxylic anhydride.
  • monofunctional hydroxy compounds As the P / JPO / 01814 compound, a known compound such as a monofunctional epoxy acrylate can be used.
  • the molecular weight of the repeating unit is preferably larger, more than 600, more preferably more than 700.
  • a diol containing an aromatic skeleton and / or an acid dianhydride is preferable as a composition which does not easily cause cold flow, and has a lower molecular weight than an aliphatic system. Rows can be prevented.
  • the preferred acid dianhydride is aromatic tetracarboxylic dianhydride.
  • Preferred diols include aromatic bisphenols and their epoxides, adducts of propylene oxide, and more preferably (meta) aders of aromatic bisphenols to diglycidyl ethers. It is a acrylate adduct, that is, bishydroxypropyl (meta) acrylate. Specific examples are as described above.
  • the photopolymerizable layer of the present invention is formed by uniformly applying the photopolymerizable resin composition containing the above components (A) to (C) on a transparent support film and drying the solvent. Is done.
  • This photopolymerizable resin composition contains an essential component and an organic solvent necessary for dissolving or uniformly dispersing an additive added as needed.
  • the solid content in the composition is 10 to 70%. It is added so as to be% by weight. The concentration is arbitrarily selected depending on the coating method and the desired film thickness.
  • the organic solvent used for this include propylene glycol monomethyl ether acetate, diglyme, ethyl acetate, butyl acetate, methyl ethyl ketone, etc., esters, ethers and ketones. It is preferably used and can easily dissolve or disperse solids, and must be sufficiently removed during the coating drying process. / 0 1
  • the photopolymerizable composition constituting the photopolymerizable layer includes a polymerization inhibitor for improving thermal stability and storage stability, coloring substances such as dyes and pigments, and Known substances such as a surfactant and a thermal crosslinking agent such as an epoxy resin or a melamine resin may be added according to the purpose and application.
  • an epoxy compound is effective as a means for improving the heat resistance, alkali resistance, and plating resistance of a cured product for interlayer insulating films, and an average particle size for coloring for one color filter.
  • the photopolymerizable resin composition containing the components (A) to (C) of the present invention may contain a solvent and the above-mentioned additives.
  • the ingredients are at least 50% by weight, preferably 80% by weight, of the solid content (excluding pigments). / 0 or more power, yo ,.
  • the essential components (A) to (C) and the additives are dissolved or uniformly dispersed in an organic solvent to prepare a photopolymerizable composition solution.
  • This photopolymerizable composition solution is uniformly applied to a support film by a coater, dried by hot-air drying or the like, and then, if necessary, covered with a protective film and wound.
  • the drying temperature is preferably 80 to 120 ° C in consideration of the thermal stability and productivity of the unsaturated compound. It is also desirable to raise the temperature in multiple stages to prevent skinning and foaming of the coating surface during drying.
  • An organic solvent often remains in the dried photopolymerizable layer, but its content must be 15% by weight or less, preferably 1 °% by weight or less.
  • the content here is 100% by weight of DFR after drying.
  • the reduced weight as the absolute dry weight after drying again at 200 ° C for 30 minutes as / 0 . / 0 . If this exceeds 15% by weight, cold flow tends to occur.
  • the thickness of the photopolymerizable layer after drying varies depending on the application, but is 1 to 10 ⁇ m for liquid crystal displays and 5 to 100 // m for circuit boards.
  • the resolution is improved as the thickness of the photopolymerizable layer is smaller, the present photopolymerizable laminate can form a via and a fine line equivalent to the thickness of the photopolymerizable layer. For example, when the thickness is 30 / ⁇ 1, a via of 30 ⁇ and a line and space of 2 ⁇ Aim can be formed. In 5 // ⁇ , an isolated line and an isolated dot of 20 / i in can be formed.
  • a transparent film that transmits active light is desirable.
  • a support layer that transmits the active light include a well-known potile terephthalate frame, a polyacrylelem, a polypropylene film for optics, and a cellulose derivative film.
  • the thickness of these films is generally 10 to 30 ⁇ m because the thinner the film, the more advantageous it is in terms of image forming properties and economy, and it is necessary to maintain strength.
  • a protective film is laminated as necessary on the surface of the photopolymerizable layer which is not in contact with the support film, but the characteristics required for this protective film are different from those of the support film.
  • the protective film has a sufficiently small adhesion to the photopolymerizable layer and can be easily peeled off.
  • An example of such a film is a polyethylene film.
  • a protective film first peel off the protective film, then heat-press and laminate the photopolymerizable layer on the substrate surface using a hot roll laminator, etc., at a heating temperature of 70 to 120 ° C.
  • the temperature is preferably 80 to 110 ° C.
  • the temperature is lower than 70 ° C, the adhesion to the substrate is poor.
  • the temperature exceeds 120 ° C, the photopolymerizable layer protrudes from the side edge, and the film thickness accuracy is impaired. This laminating property depends on the melt viscosity-temperature characteristics of the photopolymerizable layer.
  • the melt viscosity referred to here is determined by peeling only the photopolymerizable layer from the obtained DFR, filling it in a lmm ci) cavity, and using a cavity rheometer (Flow Tester CFT500 manufactured by Shimadzu Corporation). It was measured with a load of 1 kg.
  • the support layer is peeled off, and image exposure is performed with active light through a mask. If there is a support film on the photopolymerizable layer, it is removed if necessary, and then the unexposed portions of the photopolymerizable layer are developed and removed using an aqueous alkali solution.
  • an aqueous alkali solution an aqueous solution of sodium carbonate, potassium carbonate, sodium hydroxide, diethanolamine, tetramethylammonium hydroxide or the like is used.
  • These alcohol developers are selected according to the characteristics of the photopolymerizable layer, but are generally used at a concentration of 0.05 to 3%, and can be used in combination with a surfactant.
  • a metal image pattern is formed on the metal surface exposed by the development by using either a known etching method or a plating method. After that, depending on the application and the required performance, the photopolymerizable layer pattern is peeled off by a strong alkali solution, and is laminated in the same manner after heat curing while leaving a film, and used as a permanent protective film.
  • the photopolymerizable laminate of the present invention can be used when laminated on a substrate by laminating. Nevertheless, it has excellent high-resolution patterns and fine line adhesion, and can be suitably used for forming images and semiconductor circuits. Further, since the cured film retains high heat resistance and high adhesion to a substrate, it can be suitably used as a correlated insulating film, a color filter, a colored layer, a protective film, and a spacer material.
  • Solid content concentration 100 X (W 2 -W 0 ) / (Wj-Wo)
  • the molecular weight was determined by gel permeation chromatography (GPC) equipped with an RI (refractive index) detector using tetrahydrofuran as a developing solvent.
  • the molecular weight shown is the weight average molecular weight (Mw) in terms of polystyrene of the carboxyl group-containing copolymer portion excluding unreacted raw materials.
  • FHPA Equivalent reaction product of fluorene-type ethoxy resin and acrylic acid (Nippon Steel Chemical: ASF-400)
  • BFHE S (2-hydroxyethoxyphenyl) fluorene (Nippon Steel Chemical Co., Ltd.)
  • PHPA 2,2-Hydroxyphenyl (2-hydroxyphenyl) equivalent reaction product of acrylic resin and acrylic acid
  • SHPA phenyl sulphone type epho. Equivalent reaction product of xy resin and acrylic acid
  • Table 1 shows the acid value (in terms of resin solid content) of the obtained resin solution and the result of GPC analysis (area% of carboxyl group-containing copolymer in the resin solution, weight average molecular weight).
  • the unsaturated compounds, photopolymerization initiators, epoxy resins, and other additives shown in Table 3 were dissolved or dispersed in an organic solvent.
  • a solution of the photopolymerizable resin composition was prepared. The solution was applied to a polyester film having a thickness of 25 ⁇ and a width of 600 mm using a die coater, and the resulting solution was subjected to 80 — 90 — 100 — It was dried with hot air in a continuous four-stage drying oven set at 120 ° C., respectively, to obtain a 30 ⁇ m-thick photopolymerizable layer having a residual solvent ratio shown in Table 3.
  • a 60 / m-thick polyethylene protective film was laminated on the dried coating film, and the DF shown in Example 119 and Comparative Example 14 was used. R was manufactured (however, in Comparative Examples 3 and 4, the final stage of the drying furnace was set at 100 ° C.). The film properties of the obtained DFR were tested as follows. Table 3 shows the conditions and results.
  • Examples 1 to 19 showed good DFR characteristics, whereas Comparative Example 1 obtained good DFR characteristics because only the acid monoanhydride was used in the synthesis of component (A) and the molecular weight was low. I could't.
  • Comparative Example 2 since the resin (A) component is based on a phenol novolac epoxy acrylate that is brittle, the molecular weight is not increased by the acid dianhydride as in the present invention. There was a problem with the cut tip properties. Further, in Comparative Example 4, the residual solvent amount was high, and the cold flow characteristics were not good.
  • Residual solvent ratio (%) 10 Ox (D 2 -G) / (Di_ G)
  • the photopolymerizable layer is peeled off the DFR protective film on the copper surface of a copper-clad laminate (Esbanex manufactured by Nippon Steel Chemical Co., Ltd.) on which 18 m rolled copper foil is laminated.
  • the lamination was performed at a roll temperature of 100 ° C and a transfer pressure of 3 kg fZ cm 2 G at a transfer speed of 25 cm / min.
  • the resulting film was observed with a polarizing microscope to confirm that air bubbles remained.
  • YX-4000H a; Tetramethylphenyl phenyl-type ethoxy.
  • Xy resin Yukaka Shell Co., Ltd .: trade name YX4000H ⁇ ethoxy. Xy equivalent 170
  • EAB-F 4,4'-Succilamiha'nso, 'Fuenone (Hodogaya Chemical Industry Co., Ltd .: trade name EAB-FF)
  • FC430 manufactured by Sumitomo SL: Company name: FLORA-FC FC-430
  • a-4 styrene 55 weight 0 /. , ⁇ click acrylic acid 3 5 weight 0/0, a - methylstyrene 1 0% by weight of terpolymer (weight average molecular weight 1 5 0 0 0)
  • terpolymer weight average molecular weight 1 5 0 0 0
  • DFR was laminated on the copper-clad laminate (S-Vanex) in the same manner as in the above example, and exposed and developed in the same manner to form a 50 ⁇ via hole. After degreasing, washing with water, soft etching, neutralization, and washing with water, gold plating was performed on the via holes. Thereafter, the photopolymerizable layer was peeled off, and no opacity was observed.
  • the photopolymerizable laminate of the present invention exhibited good adhesion despite being transferred by a hot-laminator.
  • the resin compositions shown in Table 4 were prepared using the carboxyl group-containing copolymer resin solutions obtained in Synthesis Examples 2 and 5.
  • the resulting composition was applied to a polyester finolem having a thickness of 16 ⁇ and a width of 600 mm using a blade coater, and the temperature was set at 80 ° -90 ° -95 ° -100 ° C, respectively. It was dried with hot air in a continuous four-stage drying oven to obtain a photopolymerizable layer having a residual solvent ratio and a film thickness shown in Table 5.
  • a 60 m-thick polyethylene protective film was laminated on the dried coating film to produce the following DFR for display material.
  • Example 2 1 Transparent film with a thickness of 5 ⁇ for LCD spacer applications
  • Example 2 2 LCD protective film ⁇ Viewing angle improving structural material Use 2 ⁇ m thick transparent film
  • Example 2 3 Color filter-1.3 m thick blue colored film
  • each photopolymerizability was thermocompression-bonded on a glass substrate at 100 ° C. using a hot roll laminator. After peeling off the poly ester support film, 3 0 O mJZ cm 2 exposed through a quartz mask (bra click is 5 0 0 m J cm 2), thereby forming a pattern in Table described developing conditions. Further, postbaking was performed in a hot blast stove at 220 ° C for 30 minutes. Table 5 shows the evaluation results. The evaluation method is as described above, except for the following items.
  • the resolution was defined as the minimum line width (xm) at which the obtained image could be separated after exposure and development through a mask with a line and space width of 1: 1.
  • Pattern shape The following pattern shapes suitable for various DFR applications are indicated as “ ⁇ ” when the taper is forward tapered, and “X” when the shape is reverse tapered. The measurement was performed using a scanning electron microscope.
  • NMP N-methyl-1-pyrrolidone
  • the light blocking ratio of the black coating film was measured using an optical densitometer (DM560, manufactured by Dainippon Screen Co., Ltd.).
  • Example 21 it was found that a dot of 2 ° / Xm required for the liquid crystal spacer was formed in a regular taper and the top was flat. The adhesion was also good.
  • Example 22 the transparency and adhesion required for the protective film agent were good, and the 1 O / m line required for the structural material for improving the viewing angle could be formed.
  • Example 23 and 24 the transferability was good, and the cured film was found to have satisfactory optical properties and chemical resistance as a color filter, and also had excellent resolution.
  • TAZ 1 10 2, 4-Triclomethyl- (4-methoxystyryl) 16-Triacy
  • Pigment menthol 15 6 fine dispersion in PGMEA solvent, 15: 6, Mikuni Dyestuffs Co., Ltd. Flak pigment dispersion; Dispersion of force-Honfurac in PGMEA solvent, Made by Okuni Pigment [Table 5]
  • the film since the main component of the photopolymerizable layer is a carboxyl group-containing polymer formed by an ester bond, the film has low molecular weight and low flexibility compared to conventional bullet copolymers. It has anti-flow performance and good developability.
  • a novel photopolymerizable laminate capable of forming an unprecedented high-resolution buttery-battery-battery pattern is provided. Furthermore, not only a high-resolution resist but also a permanent protective film utilizing its hardened film characteristics is effective as a material contributing to higher performance of semiconductor devices and display devices.
  • the photopolymerizable laminate of the present invention includes a solder resist, a plating resist, an etching resist for forming a circuit board, an insulating film for multilayering a wiring board on which a semiconductor element is mounted, a photosensitive adhesive, and the like. It can be used for It can also be used as a material for semiconductor devices and liquid crystal devices.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Materials For Photolithography (AREA)
  • Macromonomer-Based Addition Polymer (AREA)

Abstract

L'invention concerne un article multicouche photopolymérisable pouvant s'utiliser comme résist sec (DFR) ; et un dispositif semiconducteur et un appareil à cristaux liquides fabriqués tous deux avec l'article multicouche. L'article multicouche comprend une couche photopolymérisable et une couche de support, la couche photopolymérisable comprenant : (A) 100 parties en poids d'une résine qui est un copolymère carboxylé obtenu par mise en réaction d'un composé diol avec un dianhydride acide et qui possède un poids moléculaire à indice de pondération compris entre 3 000 et 40 000 et une valeur acide comprise entre 50 et 200 mgKOH/g ; (B) 25 à 180 parties en poids d'un composé insaturé comprenant deux ou plusieurs groupes éthyléniques terminaux photopolymérisables par molécule ; et (C) un amorceur de photopolymérisation. L'article multicouche présente non seulement une meilleure résistance au fluage à froid, une meilleure flexibilité et une meilleure résistance de film, ainsi que de meilleures propriétés de conformité au substrat lors de la stratification et une meilleure aptitude au développement, mais il possède également d'excellentes propriétés de définition et d'adhérence. Il permet donc de former un dispositif semiconducteur, un écran, etc. haute performance.
PCT/JP2000/001814 1999-03-26 2000-03-24 Article multicouche photopolymerisable haute definition et dispositif semiconducteur fabrique avec cet article WO2000058788A1 (fr)

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JP11/84075 1999-03-26

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Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6780502B2 (en) 2001-10-02 2004-08-24 Nippon Steel Chemical Co., Ltd. Insulating resin composition and laminate obtained therefrom
WO2006075633A1 (fr) * 2005-01-17 2006-07-20 Fujifilm Corporation Materiau pour formation de motif, appareil de formation de motif et procede de formation de motif indelebile
WO2006118094A1 (fr) * 2005-04-27 2006-11-09 Mitsubishi Chemical Corporation Composition traitable thermiquement, produit traité thermiquement, et dispositif d’affichage à cristaux liquides les utilisant
WO2007072641A1 (fr) * 2005-12-22 2007-06-28 Fujifilm Corporation Matériau pour traçage de motif, dispositif de traçage de motif et procédé de traçage de motif
JP2013167687A (ja) * 2012-02-14 2013-08-29 Mitsubishi Chemicals Corp 感光性着色樹脂組成物、及びカラーフィルタ、及び液晶表示装置
JP2015069164A (ja) * 2013-09-30 2015-04-13 Jsr株式会社 感放射線性樹脂組成物、表示素子の絶縁膜、その形成方法及び表示素子
US20150197592A1 (en) * 2012-09-26 2015-07-16 Fujifilm Corporation Semi-cured product, cured product and method for producing these, optical component, curable resin composition, and compound
JP2016139043A (ja) * 2015-01-28 2016-08-04 互応化学工業株式会社 感光性樹脂組成物、プリント配線板、支持体付きドライフィルム、及び多層プリント配線板
JP2017088842A (ja) * 2015-11-02 2017-05-25 互応化学工業株式会社 カルボキシル基含有樹脂、感光性樹脂組成物、ドライフィルム、プリント配線板、及びカルボキシル基含有樹脂の製造方法
JP2017129736A (ja) * 2016-01-20 2017-07-27 互応化学工業株式会社 感光性樹脂組成物、ドライフィルム、プリント配線板、及び感光性樹脂組成物の製造方法
CN107209457A (zh) * 2015-01-28 2017-09-26 互应化学工业株式会社 感光性树脂组合物、干膜和印刷布线板
CN107250198A (zh) * 2015-01-28 2017-10-13 互应化学工业株式会社 含羧基树脂、感光性树脂组合物、干膜、印刷布线板以及含羧基树脂的制造方法
CN108475015A (zh) * 2016-01-19 2018-08-31 互应化学工业株式会社 感光性树脂组合物、干膜和印刷布线板
JP2019056867A (ja) * 2017-09-22 2019-04-11 株式会社タムラ製作所 感光性樹脂組成物
JP2020144374A (ja) * 2020-04-07 2020-09-10 互応化学工業株式会社 感光性樹脂組成物、ドライフィルム、プリント配線板、及び感光性樹脂組成物の製造方法

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JPH0570528A (ja) * 1991-09-11 1993-03-23 Nippon Steel Corp アルカリ可溶型感光性樹脂及びそれを用いたアルカリ現像型感光性樹脂組成物
JPH05339356A (ja) * 1992-02-04 1993-12-21 Nippon Steel Corp 光重合性不飽和化合物及びアルカリ現像型感光性樹脂組成物
JPH07199457A (ja) * 1993-12-29 1995-08-04 Tokyo Ohka Kogyo Co Ltd 耐熱性感光性樹脂組成物およびこれを用いた感光性ドライフィルム
JPH08123016A (ja) * 1994-10-27 1996-05-17 Hitachi Chem Co Ltd 感光性ソルダーレジスト組成物、これを用いたプリント回路板の製造法、プリント回路板及びこのプリント回路板を用いた機器
JPH08278630A (ja) * 1995-04-07 1996-10-22 Nippon Steel Chem Co Ltd 保存安定性に優れたカラーフィルター用インク及びこれを用いて形成したカラーフィルター
JPH09325494A (ja) * 1996-06-07 1997-12-16 Nippon Steel Chem Co Ltd アルカリ現像性不飽和樹脂組成物及びこれを用いた高感度ネガ型パターン形成材料
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JPH11231523A (ja) * 1998-02-10 1999-08-27 Tokyo Ohka Kogyo Co Ltd 光重合性樹脂組成物及び該光重合性樹脂組成物を用いたカラーフィルターの製造方法

Cited By (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6780502B2 (en) 2001-10-02 2004-08-24 Nippon Steel Chemical Co., Ltd. Insulating resin composition and laminate obtained therefrom
WO2006075633A1 (fr) * 2005-01-17 2006-07-20 Fujifilm Corporation Materiau pour formation de motif, appareil de formation de motif et procede de formation de motif indelebile
WO2006118094A1 (fr) * 2005-04-27 2006-11-09 Mitsubishi Chemical Corporation Composition traitable thermiquement, produit traité thermiquement, et dispositif d’affichage à cristaux liquides les utilisant
WO2007072641A1 (fr) * 2005-12-22 2007-06-28 Fujifilm Corporation Matériau pour traçage de motif, dispositif de traçage de motif et procédé de traçage de motif
JP2007171643A (ja) * 2005-12-22 2007-07-05 Fujifilm Corp パターン形成材料、並びにパターン形成装置及びパターン形成方法
JP4546393B2 (ja) * 2005-12-22 2010-09-15 富士フイルム株式会社 パターン形成材料、並びにパターン形成装置及びパターン形成方法
JP2013167687A (ja) * 2012-02-14 2013-08-29 Mitsubishi Chemicals Corp 感光性着色樹脂組成物、及びカラーフィルタ、及び液晶表示装置
US20150197592A1 (en) * 2012-09-26 2015-07-16 Fujifilm Corporation Semi-cured product, cured product and method for producing these, optical component, curable resin composition, and compound
US9334352B2 (en) * 2012-09-26 2016-05-10 Fujifilm Corporation Semi-cured product, cured product and method for producing these, optical component, curable resin composition, and compound
JP2015069164A (ja) * 2013-09-30 2015-04-13 Jsr株式会社 感放射線性樹脂組成物、表示素子の絶縁膜、その形成方法及び表示素子
JP2016139043A (ja) * 2015-01-28 2016-08-04 互応化学工業株式会社 感光性樹脂組成物、プリント配線板、支持体付きドライフィルム、及び多層プリント配線板
CN107209457A (zh) * 2015-01-28 2017-09-26 互应化学工业株式会社 感光性树脂组合物、干膜和印刷布线板
CN107250198A (zh) * 2015-01-28 2017-10-13 互应化学工业株式会社 含羧基树脂、感光性树脂组合物、干膜、印刷布线板以及含羧基树脂的制造方法
TWI656403B (zh) * 2015-01-28 2019-04-11 日商互應化學工業股份有限公司 感光性樹脂組成物、乾膜及印刷線路板（一）
CN107250198B (zh) * 2015-01-28 2020-02-21 互应化学工业株式会社 含羧基树脂、感光性树脂组合物、干膜、印刷布线板以及含羧基树脂的制造方法
JP2017088842A (ja) * 2015-11-02 2017-05-25 互応化学工業株式会社 カルボキシル基含有樹脂、感光性樹脂組成物、ドライフィルム、プリント配線板、及びカルボキシル基含有樹脂の製造方法
JP7150230B2 (ja) 2015-11-02 2022-10-11 互応化学工業株式会社 カルボキシル基含有樹脂、感光性樹脂組成物、ドライフィルム、プリント配線板、及びカルボキシル基含有樹脂の製造方法
CN108475015A (zh) * 2016-01-19 2018-08-31 互应化学工业株式会社 感光性树脂组合物、干膜和印刷布线板
CN108475015B (zh) * 2016-01-19 2022-03-18 互应化学工业株式会社 感光性树脂组合物、干膜和印刷布线板
JP2017129736A (ja) * 2016-01-20 2017-07-27 互応化学工業株式会社 感光性樹脂組成物、ドライフィルム、プリント配線板、及び感光性樹脂組成物の製造方法
JP2019056867A (ja) * 2017-09-22 2019-04-11 株式会社タムラ製作所 感光性樹脂組成物
JP2020144374A (ja) * 2020-04-07 2020-09-10 互応化学工業株式会社 感光性樹脂組成物、ドライフィルム、プリント配線板、及び感光性樹脂組成物の製造方法

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