WO2015068592A1 - 光導波路用感光性樹脂組成物および光導波路コア層形成用光硬化性フィルム、ならびにそれを用いた光導波路、光・電気伝送用混載フレキシブルプリント配線板 - Google Patents
光導波路用感光性樹脂組成物および光導波路コア層形成用光硬化性フィルム、ならびにそれを用いた光導波路、光・電気伝送用混載フレキシブルプリント配線板 Download PDFInfo
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- WO2015068592A1 WO2015068592A1 PCT/JP2014/078333 JP2014078333W WO2015068592A1 WO 2015068592 A1 WO2015068592 A1 WO 2015068592A1 JP 2014078333 W JP2014078333 W JP 2014078333W WO 2015068592 A1 WO2015068592 A1 WO 2015068592A1
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- optical waveguide
- resin composition
- core layer
- photosensitive resin
- optical
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
- G02B1/045—Light guides
- G02B1/046—Light guides characterised by the core material
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/24—Di-epoxy compounds carbocyclic
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/24—Di-epoxy compounds carbocyclic
- C08G59/245—Di-epoxy compounds carbocyclic aromatic
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/32—Epoxy compounds containing three or more epoxy groups
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/32—Epoxy compounds containing three or more epoxy groups
- C08G59/3218—Carbocyclic compounds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/32—Epoxy compounds containing three or more epoxy groups
- C08G59/38—Epoxy compounds containing three or more epoxy groups together with di-epoxy compounds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
- C08G59/70—Chelates
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
- G02B1/045—Light guides
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/04—Prisms
- G02B5/045—Prism arrays
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B6/00—Light guides; Structural details of arrangements comprising light guides and other optical elements, e.g. couplings
- G02B6/10—Light guides; Structural details of arrangements comprising light guides and other optical elements, e.g. couplings of the optical waveguide type
- G02B6/12—Light guides; Structural details of arrangements comprising light guides and other optical elements, e.g. couplings of the optical waveguide type of the integrated circuit kind
- G02B6/122—Basic optical elements, e.g. light-guiding paths
- G02B6/1221—Basic optical elements, e.g. light-guiding paths made from organic materials
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B6/00—Light guides; Structural details of arrangements comprising light guides and other optical elements, e.g. couplings
- G02B6/10—Light guides; Structural details of arrangements comprising light guides and other optical elements, e.g. couplings of the optical waveguide type
- G02B6/12—Light guides; Structural details of arrangements comprising light guides and other optical elements, e.g. couplings of the optical waveguide type of the integrated circuit kind
- G02B6/13—Integrated optical circuits characterised by the manufacturing method
- G02B6/138—Integrated optical circuits characterised by the manufacturing method by using polymerisation
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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
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
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- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K1/00—Printed circuits
- H05K1/02—Details
- H05K1/0274—Optical details, e.g. printed circuits comprising integral optical means
Definitions
- the present invention relates to a photosensitive resin for an optical waveguide used as a material for forming a core layer or the like constituting an optical waveguide in an optical / electrical transmission mixed flexible printed wiring board widely used in optical communication, optical information processing, and other general optics.
- the present invention relates to a composition, a photocurable film for forming an optical waveguide core layer, an optical waveguide using the same, and a mixed flexible printed wiring board for optical / electrical transmission.
- a mixture composed of a liquid photosensitive monomer has been used as an optical waveguide core layer forming material for a mixed flexible printed wiring board for optical / electrical transmission.
- a desired core pattern is produced by performing ultraviolet (UV) irradiation through a mask.
- UV ultraviolet
- roll-to-roll is a manufacturing process with a view to mass production from the viewpoint of surface tack after coating (tackiness).
- R-to-R -to-roll
- the optical waveguide core layer forming material needs to satisfy many required properties such as high refractive index, high transparency, high resolution patterning property, and high heat resistance as various physical properties of the cured product according to the intended use. Therefore, studies for satisfying various properties by selection of various raw materials, blending balance and the like are being conducted.
- the optical waveguide core layer forming material generally uses a technique of forming an uncured film made of the above forming material into a dry film.
- a dry film material such as low tack and flexibility of uncured material not only leads to narrowing the degree of freedom in material design, but also when producing dry film, laminating Since a base material is required on both sides, it becomes a problem from the viewpoint of resource saving and cost. Therefore, compatibility with a wet process is also regarded as important in material development (Patent Document 3).
- Patent Document 4 a photosensitive resin composition that satisfies the above characteristics by blending various resins with a special novolac type polyfunctional epoxy resin as a main ingredient.
- JP 2001-281475 A JP 2011-27903 A JP 2010-230944 A JP2011-237645A
- waveguide materials for mixed flexible printed wiring boards for optical / electrical transmission are required to have particularly high transparency among the above required characteristics and reflow resistance to withstand the solder reflow process in the manufacturing process.
- photosensitive curing that can be used as an optical waveguide core layer forming material that is highly transparent and also has reflow resistance while maintaining conventional R-to-R compatibility and high resolution patterning properties. Resin compositions are highly desired.
- the present invention has been made in view of such circumstances, and has high transparency, good R-to-R compatibility, and high resolution patterning properties as an optical waveguide forming material, particularly a core layer forming material.
- Providing a photosensitive resin composition for an optical waveguide and a photocurable film for forming an optical waveguide core layer, and an optical waveguide using the same and a flexible printed wiring board mixed for optical and electrical transmission Is the purpose.
- the present invention provides a photosensitive resin composition for an optical waveguide containing an aliphatic resin having a polymerizable substituent and a photopolymerization initiator, the fat having the polymerizable substituent.
- the first gist is a photosensitive resin composition for an optical waveguide, in which the group-based resin comprises the following (A) and (B).
- the group-based resin comprises the following (A) and (B).
- B) Bifunctional long chain aliphatic resin Bifunctional long chain aliphatic resin.
- the second gist of the present invention is a photocurable film for forming an optical waveguide core layer formed by forming the photosensitive resin composition for an optical waveguide, which is the first gist, in a film shape.
- the present invention is an optical waveguide in which a base material and a clad layer are formed on the base material, and further, a core layer that propagates an optical signal in a predetermined pattern is formed in the clad layer.
- An optical waveguide having a layer formed by curing the photosensitive resin composition for an optical waveguide according to the first aspect or the photocurable film for forming an optical waveguide core layer according to the second aspect is provided as a third optical waveguide.
- the gist is provided as a third optical waveguide.
- this invention makes the 4th summary the mixed flexible printed wiring board for optical / electrical transmission provided with the optical waveguide of the said 3rd summary.
- the present inventors have developed a photosensitive resin composition that is a core layer forming material for an optical waveguide having both high transparency, good R-to-R compatibility, high resolution patterning property, and excellent reflow resistance. We studied earnestly to get things. As a result, the inventors have found that the intended purpose can be achieved by using the photosensitive epoxy resin composition as the above-described blending component, and have reached the present invention.
- the side chain polyfunctional aliphatic resin (A) and the two-component resin are solid resin components.
- the tackiness is eliminated.
- R-to-R compatibility depends on the flexibility of the coating film after coating and drying at room temperature. (Layer) Flexibility is imparted to the amorphous film when it is not cured at the time of formation.
- the mixing weight ratio of the side chain polyfunctional aliphatic resin (A) and the bifunctional long chain aliphatic resin (B) is outside a certain range, for example, the side chain polyfunctional aliphatic resin (A ) Increases, the flexibility of the uncured amorphous film is remarkably deteriorated, and the R-to-R compatibility tends to be deteriorated.
- the side chain polyfunctional aliphatic resin (A ) Increases, the flexibility of the uncured amorphous film is remarkably deteriorated, and the R-to-R compatibility tends to be deteriorated.
- Improvement is achieved.
- the mixing weight ratio of the side chain polyfunctional aliphatic resin (A) and the bifunctional long chain aliphatic resin (B) is outside a certain range, for example, the bifunctional long chain aliphatic resin (B ) Increases, patterning property and heat resistance are remarkably deteriorated, and the loss of the waveguide tends to be deteriorated.
- the photosensitive resin composition for optical waveguides set to the above composition it has both tackiness, good R-to-R compatibility, and high resolution patterning property, and is further excellent. High transparency (low loss) and reflow resistance were obtained, and the present invention was achieved.
- the core layer forming material in the core layer forming material, is configured using an aliphatic resin that does not include an aromatic ring, thereby eliminating the influence of the fourth harmonic absorption (4v CH ) derived from the aromatic ring. It was designed.
- the above high transparency (low loss) can be more preferably dealt with by selecting, for example, a cationic skeleton in the photoacid generator. That is, the generation mechanism of the thermal degradation (coloring) of the cured product is derived from the generation of a ⁇ -conjugated system expansion factor generated by resin oxidation degradation.
- a guideline for selecting a photoacid generator is a cationic skeleton having a relatively wide ⁇ -conjugated system (for example, triphenyl) having sensitivity to an exposure wavelength of 365 nm from the viewpoint of patterning properties.
- Photoacid generators having a sulfonium salt system have been employed.
- this wide ⁇ -conjugated system skeleton is a factor that tends to be colored due to the expansion of the ⁇ -conjugated system in the oxidative degradation of the cation residue (carcass) after acid generation, it is preferably as narrow as the diphenyliodonium cation system.
- the use of a photoacid generator composed of a ⁇ -conjugated cation moiety is more suitable for high transparency (low loss).
- the specific photoacid generator is one of the narrowest ⁇ -conjugated systems among all photoacid generators. Therefore, there is no sensitivity to an exposure wavelength of 365 nm, and cross-line exposure (broad light) is required, but the obtained cured product is less colored than a triphenylsulfonium salt photoacid generator that has been conventionally used. Thus, it becomes possible to impart even better transparency (low loss).
- the resin in addition to selecting a material that exhibits an effect of suppressing yellowing due to heating as the core portion forming material, it is more preferable that the resin is yellowed after exposure as a photoacid generator. If an antimony photoacid generator that excels in lightness is used, a further effect is imparted.
- the present invention contains an aliphatic resin having a polymerizable substituent composed of a side-chain polyfunctional aliphatic resin (A) and a bifunctional long-chain aliphatic resin (B), and a photopolymerization initiator.
- This is a photosensitive resin composition for optical waveguides. Therefore, for example, when a core layer of an optical waveguide is formed using this photosensitive resin composition for an optical waveguide, the coating process and the R-to-R process are performed without changing the conventional manufacturing process. It is possible to form a core layer of an optical waveguide with low loss and excellent reflow resistance.
- Photosensitive resin composition for optical waveguide uses an aliphatic resin having a polymerizable substituent and a photopolymerization initiator. It is obtained.
- the aliphatic resin having a polymerizable substituent is composed of a side-chain polyfunctional aliphatic resin (A) and a bifunctional long-chain aliphatic resin (B).
- A side-chain polyfunctional aliphatic resin
- B bifunctional long-chain aliphatic resin
- “liquid” or “solid” means “liquid” or “solid” state at a temperature of 25 ° C.
- the aliphatic resin having a polymerizable substituent is composed of a side-chain polyfunctional aliphatic resin (A) and a bifunctional long-chain aliphatic resin (B). And it is preferable that the aliphatic resin which has the said polymeric substituent shows solid at normal temperature.
- the aliphatic resin having a polymerizable substituent is preferably one that exhibits a solid at room temperature as a whole, but an aliphatic resin that is liquid at room temperature is effective for the present invention. You may mix
- the side chain polyfunctional aliphatic resin (A) is an aliphatic resin having two or more functional groups in the side chain.
- 1,2-bis (hydroxymethyl) -1-butanol 1,2 -Polyfunctional aliphatic epoxy resins such as epoxy-4- (2-oxiranyl) cyclohexane adducts. These may be used alone or in combination of two or more. Specific examples include EHPE3150 (manufactured by Daicel).
- the side chain polyfunctional aliphatic resin (A) is preferably a solid, and in this case, the solid represents a solid state at a normal temperature (25 ° C.) as described above. means.
- a polymerizable substituent is present, and the polymerizable substituent is preferably a cationic polymerizable substituent.
- the cationic polymerizable substituent include an epoxy group, an epoxy group having an alicyclic skeleton, and a substituent having an oxetane skeleton.
- Examples of the bifunctional long chain aliphatic resin (B) include a long chain aliphatic epoxy resin having an epoxy group that is a polymerizable functional group at both ends.
- the long-chain aliphatic epoxy resin it becomes possible to reduce the crosslinking density in cationic polymerization, and the flexibility of the cured product can be imparted.
- Examples thereof include hydrogenated bisphenol A type epoxy resin and hydrogenated bisphenol F type epoxy resin that do not have an aromatic ring. These may be used alone or in combination of two or more. Specific examples include YX-8040 (manufactured by Mitsubishi Chemical Corporation), ST-4000D (manufactured by Nippon Steel Chemical Co., Ltd.), and the like.
- the aliphatic resin includes the alicyclic epoxy resin.
- the bifunctional long chain aliphatic resin (B) is preferably a solid, and in this case, the solid represents a solid state at a normal temperature (25 ° C.) as described above. means.
- an aliphatic resin having no epoxy group that is, an aliphatic resin that acts as a binder resin, can provide the same effects as described above. is there.
- the photopolymerization initiator is used for imparting, for example, ultraviolet curability to the photosensitive resin composition in order to impart curability by light irradiation.
- photopolymerization initiator examples include triphenylsulfonium hexafluoroantimonate, triphenylsulfonium hexafluorophosphate, p- (phenylthio) phenyldiphenylsulfonium hexafluoroantimonate, p- (phenylthio) phenyldiphenylsulfonium hexafluorophosphate, 4-chlorophenyldiphenylsulfonium hexafluorophosphate, 4-chlorophenyldiphenylsulfonium hexafluoroantimonate, bis [4- (diphenylsulfonio) phenyl] sulfide bishexafluorophosphate, bis [4- (diphenylsulfonio) phenyl ] Sulfide bishexafluoroantimonate, (2,4-cyclopentadien-1-
- R 1 and R 2 are preferably an alkyl group having 1 to 15 carbon atoms, and particularly preferably a mixture having an alkyl group having 10 to 13 carbon atoms.
- Specific examples include iodonium salt type photopolymerization initiators such as WPI-116 (manufactured by Wako Pure Chemical Industries, Ltd.).
- the content of the photopolymerization initiator may be set to 0.1 to 3 parts by weight with respect to 100 parts by weight of the resin component of the photosensitive resin composition (for example, an aliphatic resin having a polymerizable substituent).
- the amount is preferably 0.5 to 1 part by weight. That is, if the content of the photopolymerization initiator is too small, it is difficult to obtain satisfactory photocurability by light irradiation (ultraviolet irradiation), and if it is too much, the photosensitivity is increased and there is a tendency to cause a shape abnormality during patterning. There is a tendency that the required physical properties of the initial loss are deteriorated.
- the photosensitive resin composition of the present invention in addition to the aliphatic resin having the polymerizable substituent and the photopolymerization initiator, if necessary, for example, silane-based or titanium-based to improve adhesion Coupling agents, cycloolefin oligomers and polymers such as olefin oligomers and norbornene polymers, adhesion imparting agents such as synthetic rubbers and silicone compounds, various antioxidants such as hindered phenol antioxidants and phosphorus antioxidants , Leveling agents, antifoaming agents and the like. These additives are appropriately blended within a range that does not impair the effects of the present invention. These can be used alone or in combination of two or more.
- the amount of the antioxidant is preferably set to less than 3 parts by weight, particularly preferably 100 parts by weight of the resin component of the photosensitive resin composition (for example, an aliphatic resin having a polymerizable substituent). Is 1 part by weight or less. That is, when there is too much content of antioxidant, the tendency for the required physical property of initial loss to deteriorate will be seen.
- the photosensitive resin composition of the present invention is obtained by stirring and mixing the aliphatic resin having a polymerizable substituent and a photopolymerization initiator, and further, if necessary, other additives at a predetermined blending ratio. Can be prepared. Furthermore, in order to prepare the photosensitive resin composition of the present invention as a coating varnish, it may be dissolved by stirring in an organic solvent under heating (for example, about 60 to 90 ° C.). The amount of the organic solvent used is appropriately adjusted. For example, it is 20 to 80 with respect to 100 parts by weight of the resin component of the photosensitive resin composition (for example, an aliphatic resin having a polymerizable substituent). It is preferably set to parts by weight, particularly preferably 30 to 50 parts by weight.
- organic solvent used in preparing the coating varnish examples include, for example, ethyl lactate, methyl ethyl ketone, cyclohexanone, ethyl lactate, 2-butanone, N, N-dimethylacetamide, diglyme, diethylene glycol methyl ethyl ether, propylene glycol methyl Examples include acetate, propylene glycol monomethyl ether, tetramethylfuran, dimethoxyethane and the like. These organic solvents are used alone or in combination of two or more, and are used in a predetermined amount within the above range, for example, so as to have a viscosity suitable for coating.
- optical waveguide using the photosensitive resin composition of the present invention as a core layer forming material will be described.
- the optical waveguide obtained by the present invention includes, for example, a base material, a clad layer (under clad layer) formed in a predetermined pattern on the base material, and a predetermined pattern for propagating an optical signal on the clad layer. And a clad layer (over clad layer) formed on the core layer.
- the optical waveguide obtained by this invention is characterized by the said core layer being formed with the above-mentioned photosensitive resin composition.
- the resin composition for clad layer formation which consists of the same component composition may be used, and the resin composition of a different component composition may be used.
- the cladding layer needs to be formed so that the refractive index is smaller than that of the core layer.
- the optical waveguide can be manufactured through the following processes, for example. That is, a base material is prepared, and a photosensitive varnish made of a photosensitive resin composition that is a clad layer forming material is applied onto the base material. The photosensitive varnish is cured by irradiating the varnish-coated surface with light such as ultraviolet rays and further performing a heat treatment as necessary. In this manner, an under cladding layer (a lower portion of the cladding layer) is formed.
- an uncured layer for core formation is formed on the undercladding layer by coating a core layer forming material (photosensitive varnish) obtained by dissolving the photosensitive resin composition of the present invention in an organic solvent. .
- a core layer forming material photosensitive varnish
- the organic solvent is heated and dried to remove the organic solvent, thereby forming an uncured optical waveguide core layer forming photocurable film.
- the Rukoto A photomask for exposing a predetermined pattern (optical waveguide pattern) is disposed on the uncured layer surface for core formation, and light such as ultraviolet rays is irradiated through the photomask. Heat treatment is performed. Thereafter, the unexposed portion of the core forming uncured layer is dissolved and removed using a developer to form a core layer having a predetermined pattern.
- a photosensitive varnish made of the photosensitive resin composition which is the cladding layer forming material, is applied, followed by light irradiation such as ultraviolet irradiation, and further heat treatment as necessary.
- light irradiation such as ultraviolet irradiation
- an over clad layer (upper part of the clad layer) is formed.
- Examples of the base material include a silicon wafer, a metal substrate, a polymer film, and a glass substrate.
- the metal substrate include stainless steel plates such as SUS.
- Specific examples of the polymer film include a polyethylene terephthalate (PET) film, a polyethylene naphthalate film, and a polyimide film. The thickness is usually set in the range of 10 ⁇ m to 3 mm.
- ultraviolet irradiation is performed.
- the ultraviolet light source in the ultraviolet irradiation include a low pressure mercury lamp, a high pressure mercury lamp, and an ultrahigh pressure mercury lamp.
- the irradiation amount of ultraviolet rays is usually 10 to 20000 mJ / cm 2 , preferably 100 to 15000 mJ / cm 2 , more preferably about 500 to 10000 mJ / cm 2 .
- a heat treatment may be further performed in order to complete the curing by the photoreaction.
- the heat treatment conditions are usually 80 to 250 ° C., preferably 100 to 150 ° C., for 10 seconds to 2 hours, preferably 5 minutes to 1 hour.
- the cladding layer forming material examples include various liquid epoxy resins such as bisphenol A type epoxy resin, bisphenol F type epoxy resin, hydrogenated bisphenol A type epoxy resin, fluorinated epoxy resin, epoxy modified silicone resin, and solid epoxy. Resin, and further, a resin composition containing the above-mentioned various photoacid generators as appropriate, can be mentioned, and a blending design is appropriately made to have a low refractive index as compared with the core layer forming material. Furthermore, since the clad layer forming material is prepared and applied as needed, the optical waveguide using various conventionally known organic solvents and the core layer forming material so as to obtain a viscosity suitable for coating. Various additives (antioxidants, adhesion-imparting agents, leveling agents, UV absorbers) that do not deteriorate the function of the resin may be used in appropriate amounts.
- additives antioxidants, adhesion-imparting agents, leveling agents, UV absorbers
- organic solvent used for preparing the varnish are as described above, for example, ethyl lactate, methyl ethyl ketone, cyclohexanone, ethyl lactate, 2-butanone, N, N-dimethylacetamide, diglyme, diethylene glycol methyl ethyl ether, propylene glycol methyl acetate. Propylene glycol monomethyl ether, tetramethylfuran, dimethoxyethane and the like. These organic solvents are used alone or in combination of two or more in an appropriate amount so as to obtain a viscosity suitable for coating.
- a coating method using the forming material of each layer on the substrate for example, a spin coater, a coater, a circular coater, a bar coater, or a coating method, screen printing, a gap using a spacer, or the like.
- a method of injecting by capillary action a method of continuously applying R-to-R with a coating machine such as a multi-coater, and the like can be used.
- the optical waveguide can also be made into a film-like optical waveguide by peeling and removing the substrate.
- the optical waveguide thus obtained can be used as, for example, an optical waveguide for a mixed flexible printed wiring board for optical / electrical transmission.
- each photosensitive varnish which is a clad layer forming material and a core layer forming material was prepared prior to production of an optical waveguide as an example.
- the photosensitive varnish which is the cladding layer forming material, was applied onto a silicon wafer having a thickness of about 500 ⁇ m using a spin coater, and then exposed to 5000 mJ (wavelength 365 nm integration) with a cross line (broad light). Thereafter, post-heating was performed at 130 ° C. for 10 minutes to produce an under cladding layer (thickness 20 ⁇ m).
- a photosensitive varnish as a core layer forming material is applied onto the formed underclad layer using a spin coater, and then an organic solvent (ethyl lactate) is dried on a hot plate (130 ° C. ⁇ 5 minutes).
- an organic solvent ethyl lactate
- Example 2 In the preparation of the photosensitive varnish that is the core layer forming material, the blending ratio of the aliphatic resin component is 75 parts of solid polyfunctional aliphatic epoxy resin (EHPE3150, manufactured by Daicel), solid hydrogenated bisphenol A type epoxy resin. (YX-8040, manufactured by Mitsubishi Chemical Corporation) Changed to 25 parts. Other than that was carried out similarly to Example 1, and produced the optical waveguide.
- EHPE3150 solid polyfunctional aliphatic epoxy resin
- YX-8040 manufactured by Mitsubishi Chemical Corporation
- Example 3 In the preparation of the photosensitive varnish that is the core layer forming material, the blending ratio of the resin component of the aliphatic resin is 67 parts of solid polyfunctional aliphatic epoxy resin (EHPE3150, manufactured by Daicel), solid hydrogenated bisphenol A type epoxy resin. (YX-8040, manufactured by Mitsubishi Chemical Corporation) Changed to 33 parts. Other than that was carried out similarly to Example 1, and produced the optical waveguide.
- EHPE3150 solid polyfunctional aliphatic epoxy resin
- YX-8040 manufactured by Mitsubishi Chemical Corporation
- Example 4 In the preparation of the photosensitive varnish that is the core layer forming material, the blending ratio of the aliphatic resin component is 50 parts of solid polyfunctional aliphatic epoxy resin (EHPE3150, manufactured by Daicel), solid hydrogenated bisphenol A type epoxy resin. (YX-8040, manufactured by Mitsubishi Chemical Corporation) was changed to 50 parts. Other than that was carried out similarly to Example 1, and produced the optical waveguide.
- EHPE3150 solid polyfunctional aliphatic epoxy resin
- YX-8040 solid hydrogenated bisphenol A type epoxy resin
- Example 5 In the preparation of the photosensitive varnish as the core layer forming material, the amount of the photoacid generator (WPI-116, manufactured by Wako Pure Chemical Industries, Ltd.) was changed to 3 parts. Other than that was carried out similarly to Example 4, and produced the optical waveguide.
- WPI-116 manufactured by Wako Pure Chemical Industries, Ltd.
- Example 6 In the preparation of the photosensitive varnish that is the core layer forming material, the amount of the photoacid generator (WPI-116, manufactured by Wako Pure Chemical Industries, Ltd.) was changed to 0.5 part. Other than that was carried out similarly to Example 4, and produced the optical waveguide.
- WPI-116 manufactured by Wako Pure Chemical Industries, Ltd.
- a photosensitive resin composition (Example product) comprising a solid polyfunctional aliphatic epoxy resin and a solid hydrogenated bisphenol A type epoxy resin in combination, and a core formed using the photosensitive resin composition
- Optical waveguides with layers have good evaluation results in all of tack evaluation, R-to-R compatibility (crack) evaluation, patterning evaluation, optical waveguide loss evaluation (linear loss), and reflow resistance evaluation It was.
- a photosensitive resin composition (comparative product 1) using a bisphenol A type epoxy resin which is an aromatic resin together with a solid polyfunctional aliphatic epoxy resin, a cresol novolac type polyfunctional epoxy resin and bisphenol A photosensitive resin composition using A-type epoxy resin (Comparative Example 2 products) and an optical waveguide provided with a core layer formed using each of the photosensitive resin compositions described above are evaluated for tackiness, R-to- Good results were obtained with respect to R compatibility (crack) evaluation, patterning evaluation and reflow resistance evaluation, but inferior evaluation results with respect to optical waveguide loss evaluation (linear loss).
- the photosensitive resin composition for an optical waveguide of the present invention is useful as a material for forming a constituent part of an optical waveguide, particularly as a core layer forming material.
- the optical waveguide produced using the said photosensitive resin composition for optical waveguides is used for the mixed flexible printed wiring board for optical / electrical transmission, etc., for example.
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Abstract
Description
(A)側鎖多官能脂肪族樹脂。
(B)二官能長鎖脂肪族樹脂。
本発明の光導波路用感光性樹脂組成物(以下、単に「感光性樹脂組成物」という場合がある。)は、重合性置換基を有する脂肪族系樹脂、および、光重合開始剤を用いて得られるものである。そして、本発明においては、上記重合性置換基を有する脂肪族系樹脂が、側鎖多官能脂肪族樹脂(A)と、二官能長鎖脂肪族樹脂(B)からなることを特徴とする。なお、本発明において、「液状」、あるいは「固形」とは、25℃の温度下において「液状」または「固形」状態を呈することを意味する。
以下、各種成分について順に説明する。
上記重合性置換基を有する脂肪族系樹脂は、側鎖多官能脂肪族樹脂(A)と、二官能長鎖脂肪族樹脂(B)から構成されてなるものである。そして、上記重合性置換基を有する脂肪族系樹脂は、常温で固形を示すものであることが好ましい。なお、本発明においては、上記重合性置換基を有する脂肪族系樹脂としては、全体が常温で固形を示すものであることが好ましいが、常温で液状を示す脂肪族系樹脂を本発明の効果を阻害しない範囲内(例えば、感光性樹脂組成物全体の5重量%程度以下)にて配合してもよい。
上記光重合開始剤は、感光性樹脂組成物に対して光照射による硬化性を付与するため、例えば、紫外線硬化性を付与するために用いられるものである。
つぎに、本発明の感光性樹脂組成物をコア層の形成材料として用いてなる光導波路について説明する。
まず、実施例となる光導波路の作製に先立ち、クラッド層形成材料およびコア層形成材料である各感光性ワニスを調製した。
遮光条件下にて、液状二官能フッ化アルキルエポキシ樹脂(H022、東ソーエフテック社製)50部、液状二官能脂環式エポキシ樹脂(セロキサイド2021P、ダイセル社製)50部、光酸発生剤(アデカオプトマーSP-170、アデカ社製)4.0部、リン系酸化防止剤(HCA、三光社製)0.54部、シランカップリング剤(KBM-403、信越シリコーン社製)1部を混合し80℃加熱下にて撹拌完溶させ、その後室温(25℃)まで冷却した後、直径1.0μmのメンブランフィルタを用いて加熱加圧濾過を行なうことにより、クラッド層形成材料となる感光性ワニスを調製した。
遮光条件下にて、固形多官能脂肪族エポキシ樹脂(EHPE3150、ダイセル社製)80部、固形水添ビスフェノールA型エポキシ樹脂(YX―8040、三菱化学社製)20部、光酸発生剤(WPI-116、和光純薬工業社製)1.0部、ヒンダードフェノール系酸化防止剤(Songnox1010、共同薬品社製)0.5部、リン系酸化防止剤(HCA、三光社製)0.5部を、乳酸エチル40部に混合し、85℃加熱下にて撹拌完溶させ、その後室温(25℃)まで冷却した後、直径1.0μmのメンブランフィルタを用い加熱加圧濾過を行なうことにより、コア層形成材料となる感光性ワニスを調製した。
<アンダークラッド層の作製>
スピンコーターを用いて、上記クラッド層形成材料である感光性ワニスを厚み約500μmのシリコンウェハ上に塗工した後、混線(ブロード光)にて5000mJ(波長365nm積算)の露光を行なった。その後、130℃×10分間の後加熱を行なうことによりアンダークラッド層(厚み20μm)を作製した。
形成されたアンダークラッド層上に、スピンコーターを用いて、コア層形成材料である感光性ワニスを塗工した後、ホットプレート上にて有機溶剤(乳酸エチル)を乾燥させる(130℃×5分間)ことにより、未硬化フィルム状態の未硬化層を形成した。形成された未硬化層に対して、混線(ブロード光)にて9000mJ(波長365nm積算)のマスクパターン露光〔パターン幅/パターン間隔(L/S)=50μm/200μm〕を行ない、後加熱(140℃×5分間)を行なった。その後、N,N-ジメチルアセトアミド(DMAc)中にて現像(25℃×3分間)を行ない、水洗し、ホットプレート上にて水分を乾燥(120℃×5分間)させることにより、所定パターンのコア層(厚み55μm)を作製した。
コア層形成材料である感光性ワニスの調製において、脂肪族系樹脂の樹脂成分の配合割合を、固形多官能脂肪族エポキシ樹脂(EHPE3150、ダイセル社製)75部、固形水添ビスフェノールA型エポキシ樹脂(YX―8040、三菱化学社製)25部に変えた。それ以外は実施例1と同様にして光導波路を作製した。
コア層形成材料である感光性ワニスの調製において、脂肪族系樹脂の樹脂成分の配合割合を、固形多官能脂肪族エポキシ樹脂(EHPE3150、ダイセル社製)67部、固形水添ビスフェノールA型エポキシ樹脂(YX―8040、三菱化学社製)33部に変えた。それ以外は実施例1と同様にして光導波路を作製した。
コア層形成材料である感光性ワニスの調製において、脂肪族系樹脂の樹脂成分の配合割合を、固形多官能脂肪族エポキシ樹脂(EHPE3150、ダイセル社製)50部、固形水添ビスフェノールA型エポキシ樹脂(YX―8040、三菱化学社製)50部に変えた。それ以外は実施例1と同様にして光導波路を作製した。
コア層形成材料である感光性ワニスの調製において、光酸発生剤(WPI-116、和光純薬工業社製)の配合量を3部に変えた。それ以外は実施例4と同様にして光導波路を作製した。
コア層形成材料である感光性ワニスの調製において、光酸発生剤(WPI-116、和光純薬工業社製)の配合量を0.5部に変えた。それ以外は実施例4と同様にして光導波路を作製した。
コア層形成材料である感光性ワニスの調製において、樹脂成分の配合組成を、固形多官能脂肪族エポキシ樹脂(EHPE3150、ダイセル社製)67部、ビスフェノールA型エポキシ樹脂(YL-6810、三菱化学社製)33部に代えた。それ以外は実施例1と同様にして光導波路を作製した。
コア層形成材料である感光性ワニスの調製において、樹脂成分の配合割合を、クレゾールノボラック型多官能エポキシ樹脂(YDCN-700-10、新日鉄住金化学社製)67部、ビスフェノールA型エポキシ樹脂(YL-6810、三菱化学社製)33部に代えるとともに、光酸発生剤としてWPI-116(和光純薬工業社製)をSP-170(アデカ社製)に代えた。それ以外は実施例1と同様にして光導波路を作製した。
上記実施例および比較例において調製したコア層形成材料となる感光性ワニスを、厚み約500μmのシリコンウェハ上にスピンコーターを用いて塗工し、ホットプレート上にて乾燥(130℃×5分間)を行なうことにより未硬化フィルム層(厚み約50μm)を作製した。得られた未硬化フィルム層の表面を指触により確認し、その結果、下記の基準に基づき評価した。
○:タックが無く、かつ表面荒れが発生しなかった。
×:タックを有しており、かつ表面荒れが発生した。
上記実施例および比較例において調製したコア層形成材料となる感光性ワニスを、厚み50μmのSUS基材上にスピンコーターにて塗工し、乾燥(130℃×5分間)を行なうことにより厚み約50μmの未硬化フィルムを作製した。上記SUS基材上に形成された未硬化フィルム(アモルファスフィルム)を、直径8cmの巻き芯に沿って巻回し、フィルムに生じたクラックの有無を目視により確認した。その結果、下記の基準に基づき評価した。
○:クラックが発生しなかった。
×:クラックが発生した。
上記実施例および比較例において調製したコア層形成材料となる感光性ワニスを用いて、上記アンダークラッド層上に形成されたコア層パターンを光学顕微鏡にて確認した。その結果、下記の基準に基づき評価した。
○:コア層パターンの形状が、パターンうねりや裾引き等が無く矩形に形成された。
×:コア層パターンの形状が矩形になっておらず、パターンうねりあるいは裾引き等の形状異常を生起した。
上記実施例および比較例により得られた光導波路のコア層パターン上に、スピンコーターを用いて、クラッド層形成材料である感光性ワニスを塗工した後、ホットプレート上にてプリベーク(100℃×5分間)した。その後、混線(ブロード光)にて5000mJ(波長365nm積算)の露光を行ない、後加熱(120℃×5分間)を行なうことにより、オーバークラッド層を形成して光導波路(コア層パターン上のオーバークラッド層の厚み15μm、光導波路総厚み90μm)を作製した。
○:全直線損失が0.04dB/cm以下であった。
×:全直線損失が0.04dB/cmを超える結果となった。
上記光導波路をサンプルとして用い、リフローシミュレーター(SANYOSEIKO製、SMT Scope SK-5000)にて空気雰囲気下、ピーク温度250~255℃×45秒の加熟工程に暴露した後、上記と同様にして光導波路損失(直線損失)の評価を行なった。その結果、下記の基準に基づき評価した。
○:リフロー加熟後の損失増加が0.01dB/cm未満であった。
×:リフロー加熱後の損失増加が0.01dB/cmを超える結果となった。
Claims (9)
- 重合性置換基を有する脂肪族系樹脂および光重合開始剤を含有する光導波路用感光性樹脂組成物であって、上記重合性置換基を有する脂肪族系樹脂が下記(A)および(B)からなることを特徴とする光導波路用感光性樹脂組成物。
(A)側鎖多官能脂肪族樹脂。
(B)二官能長鎖脂肪族樹脂。 - 重合性置換基がカチオン重合性置換基である請求項1記載の光導波路用感光性樹脂組成物。
- 側鎖多官能脂肪族樹脂(A)および二官能長鎖脂肪族樹脂(B)の混合重量比[(A):(B)]が、(A):(B)=4:1~1:1である請求項1または2記載の光導波路用感光性樹脂組成物。
- 重合性置換基を有する脂肪族系樹脂が、常温で固形を示すものである請求項1~3のいずれか一項に記載の光導波路用感光性樹脂組成物。
- 基材とその基材上にクラッド層が形成され、さらに上記クラッド層中に所定パターンで、光信号を伝搬するコア層が形成されてなる光導波路におけるコア層形成材料である請求項1~5のいずれか一項に記載の光導波路用感光性樹脂組成物。
- 請求項1~6のいずれか一項に記載の光導波路用感光性樹脂組成物をフィルム状に形成してなる光導波路コア層形成用光硬化性フィルム。
- 基材とその基材上にクラッド層が形成され、さらに上記クラッド層中に所定パターンで、光信号を伝搬するコア層が形成されてなる光導波路であって、上記コア層が、請求項1~5のいずれか一項に記載の光導波路用感光性樹脂組成物、または請求項7記載の光導波路コア層形成用光硬化性フィルムを硬化させることにより形成されてなることを特徴とする光導波路。
- 請求項8記載の光導波路を備えることを特徴とする光・電気伝送用混載フレキシブルプリント配線板。
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US15/028,567 US9857504B2 (en) | 2013-11-08 | 2014-10-24 | Optical waveguide photosensitive resin composition, photocurable film for forming optical waveguide core layer, optical waveguide using same, and mixed flexible printed circuit board for optical/electrical transmission |
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JP6584050B2 (ja) * | 2013-11-08 | 2019-10-02 | 日東電工株式会社 | 光導波路用感光性樹脂組成物および光導波路コア層形成用光硬化性フィルム、ならびにそれを用いた光導波路、光・電気伝送用混載フレキシブルプリント配線板 |
KR101598826B1 (ko) * | 2015-08-28 | 2016-03-03 | 영창케미칼 주식회사 | 에칭 내성이 우수한 i-선용 네가티브형 포토레지스트 조성물 |
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CN105593262A (zh) | 2016-05-18 |
JP2015091910A (ja) | 2015-05-14 |
TW201529701A (zh) | 2015-08-01 |
US20160252655A1 (en) | 2016-09-01 |
TWI653286B (zh) | 2019-03-11 |
CN105593262B (zh) | 2018-05-25 |
KR20160083845A (ko) | 2016-07-12 |
US9857504B2 (en) | 2018-01-02 |
JP6332590B2 (ja) | 2018-05-30 |
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