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WO2023210629A1 - Composition de résine pour guide d'ondes optique, et film sec et guide d'ondes optique l'utilisant - Google Patents

Composition de résine pour guide d'ondes optique, et film sec et guide d'ondes optique l'utilisant Download PDF

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Publication number
WO2023210629A1
WO2023210629A1 PCT/JP2023/016252 JP2023016252W WO2023210629A1 WO 2023210629 A1 WO2023210629 A1 WO 2023210629A1 JP 2023016252 W JP2023016252 W JP 2023016252W WO 2023210629 A1 WO2023210629 A1 WO 2023210629A1
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Prior art keywords
epoxy resin
optical waveguide
resin composition
resin
mass
Prior art date
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PCT/JP2023/016252
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English (en)
Japanese (ja)
Inventor
彩 吉田
潤子 栗副
直幸 近藤
麻稀 田中
敦史 山口
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Panasonic Intellectual Property Management Co Ltd
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Panasonic Intellectual Property Management Co Ltd
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Priority to JP2024517334A priority Critical patent/JPWO2023210629A1/ja
Publication of WO2023210629A1 publication Critical patent/WO2023210629A1/fr
Anticipated expiration legal-status Critical
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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
    • 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
    • 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
    • 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
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable

Definitions

  • the present invention relates to a resin composition for an optical waveguide, and a dry film and optical waveguide using the same.
  • optical fiber has been the mainstream as a transmission medium in the fields of FTTH (Fiber to the Home) and long-distance and medium-distance communications in the automotive field.
  • FTTH Fiber to the Home
  • high-speed transmission using light has become necessary even over short distances of 1 m or less.
  • optical waveguide-type optical wiring boards are used, which are capable of high-density wiring (narrow pitch, branching, crossing, multilayering, etc.), surface mounting, integration with electrical boards, and bendability in small diameters, which are not possible with optical fibers. is suitable.
  • optical waveguide As a material used to form an optical waveguide, for example, acrylic resin, which is widely used in the manufacture of optical fibers, is known.
  • acrylic resin which is widely used in the manufacture of optical fibers
  • optical waveguides made of acrylic resin do not have heat resistance that can withstand heating conditions used to form electrical circuits, such as high-temperature reflow conditions for lead-free solder.
  • Patent Documents 1 and 2 a resin composition containing an epoxy resin and a curing agent is used to form bonding members for optical waveguides and electric circuit boards in order to suppress the deterioration of connection reliability due to high temperatures.
  • Patent Documents 1 and 2 by setting the thermal expansion coefficient of the bonding member to 80 ppm or less, it is possible to suppress a decrease in the mechanical strength of the bonding member at a high temperature, and a decrease in electrical connection reliability can be suppressed. It is said that it can be done.
  • Patent Document 3 discloses an optical waveguide forming material containing an epoxy resin as a main component and a boron-based photoacid generator.
  • the board When components are mounted on a board on which optical waveguides are laminated by reflow or the like (connected to an optical element), the board may be subjected to heat treatment at 150° C. or higher.
  • the resin compositions used in the inventions described in Patent Documents 1 and 2 have a low coefficient of thermal expansion in their cured products, but also have a low glass transition temperature (Tg) of 0 to 150°C. If the material has a Tg of 150° C. or lower, the storage modulus at 150° C. will be small, and there is a risk that the end face of the waveguide will be deformed when subjected to the heat treatment described above. When the waveguide end face is deformed, a problem arises in that connection reliability decreases. Further, the optical waveguide forming material described in Patent Document 3 is also not an invention that solves the problem of deformation of the waveguide end face described above.
  • the present invention provides a resin composition for optical waveguides that can improve the above problems, reduce end face deformation due to component mounting under high temperatures, and suppress deterioration in connection reliability, as well as dry films and optical waveguides using the same.
  • the purpose is to provide.
  • the resin composition for an optical waveguide contains an epoxy resin (A) and a photoacid generator (B), and the epoxy resin (A) has three or more epoxy groups. It also contains a polyfunctional epoxy resin (a-1) having an epoxy equivalent of 250 g/eq or less and a bisphenol A epoxy resin (a-2), and the photoacid generator (B) is an antimony-based photoacid generator. It is characterized by containing.
  • FIG. 1 is a schematic cross-sectional view for explaining one embodiment of a method for forming an optical waveguide using the resin composition of this embodiment.
  • the resin composition for an optical waveguide (hereinafter sometimes simply referred to as a resin composition) of the present embodiment contains an epoxy resin (A) and a photoacid generator (B).
  • the epoxy resin (A) contains a polyfunctional epoxy resin (a-1) having three or more epoxy groups and an epoxy equivalent of 250 g/eq or less, and a bisphenol A epoxy resin (a-2).
  • the photoacid generator (B) contains an antimony-based photoacid generator.
  • the present invention it is possible to provide a resin composition for an optical waveguide that can reduce end face deformation due to component mounting under high temperature and suppress deterioration in connection reliability, as well as a dry film and an optical waveguide using the same. .
  • the resin composition of this embodiment has a high storage modulus at 150° C. in its cured product. If the storage elastic modulus at 150° C. is high, it is possible to suppress end face deformation, which is a problem especially when used in a cladding layer, and further, it is possible to suppress a decrease in connection reliability. Further, the resin composition of the present embodiment preferably has a storage modulus of 100 MPa or more at 150° C. after curing. It is thought that this makes it possible to more reliably obtain the effects described above. A more preferable storage modulus (150° C.) is 110 MPa or more. Although the upper limit of the storage modulus is not particularly limited, it is preferably 600 MPa or less from the viewpoint that if the elastic modulus is large, the warpage of the underlying base material on which the waveguide is formed will increase.
  • the resin composition of this embodiment is for optical waveguides, and can be used for both cladding layers and core layers. Since the above-mentioned deformation of the waveguide end face mainly occurs in the cladding layer, the resin composition of this embodiment can be used more effectively for the cladding layer.
  • Epoxy resin (A) The epoxy resin (A) of this embodiment includes a polyfunctional epoxy resin (a-1) having three or more epoxy groups and an epoxy equivalent of 250 g/eq or less, and a bisphenol A epoxy resin (a-2). Contains. Additionally, a hydrogenated bisphenol A type epoxy resin (a-3) may be contained. Further, the epoxy resin (A) may contain a hydroxyl group-containing epoxy (a-1). Each epoxy resin will be explained below.
  • ⁇ Multifunctional epoxy resin (a-1) As the polyfunctional epoxy resin (a-1) of the present embodiment, any polyfunctional epoxy resin having three or more epoxy groups and an epoxy equivalent of 250 g/eq or less can be used without particular limitation. More specifically, for example, 2-[4-(2,3-epoxypropoxy)phenyl]-2-[4-[1,1-bis[4-([2,3-epoxypropoxy]phenyl)] Examples include ethyl]phenyl]propane and cresol novolac type epoxy resins.
  • polyfunctional epoxy resins (a-1) can also be used, such as "VG3101” manufactured by Printec Co., Ltd., "EHPE-3150” manufactured by Daicel Chemical Industries, Ltd., and “EHPE-3150” manufactured by Nippon Kayaku Co., Ltd. Examples include “EPPN-502".
  • the polyfunctional epoxy resin (a-1) may be used alone or in combination of two or more.
  • the epoxy resin (A) contains the polyfunctional epoxy resin (a-1), the handleability when the resin composition is made into a film is improved.
  • the lower limit of the epoxy equivalent of the polyfunctional epoxy resin (a-1) is not particularly limited, but from the viewpoint of film handling properties, it is preferably 150 g/eq or more.
  • the content of the polyfunctional epoxy resin (a-1) in the resin composition of the present embodiment is preferably 10% by mass or more and 20% by mass or less based on the total amount of the epoxy resin (A). With such a content, there is an advantage that good handling property when made into a film is more reliably obtained, and also good releasability of a release film during production of an optical waveguide is obtained.
  • a more preferable content is 10% by mass or more and 15% by mass or less.
  • the bisphenol A epoxy resin (a-2) used in this embodiment may be a solid bisphenol A epoxy resin or a liquid bisphenol A epoxy resin.
  • the epoxy equivalent of the bisphenol A epoxy resin (a-2) is preferably about 170 to 1200 g/eq.
  • the bisphenol A type epoxy resin (a-2) may be prepared by a known method, but a commercially available one can also be used. Examples include 1002, 1003, 1055, 1004, 1004AF, 1003F, 1004F, 1005F, 1004FS, 1006FS, and 1007FS. In addition, if it is liquid, examples include “Epicron (registered trademark) 850S” manufactured by DIC Corporation and "JER (registered trademark) 825" manufactured by Mitsubishi Chemical Corporation.
  • the bisphenol A type epoxy resin (a-2) may be used alone or in combination of two or more.
  • at least one solid bisphenol A epoxy resin and at least one liquid bisphenol A epoxy resin are used in combination. is desirable.
  • the resin composition of the present embodiment has the advantage that it becomes a highly transparent resin composition and is easily cured by ultraviolet light.
  • the content of the bisphenol A epoxy resin (a-2) in the resin composition of the present embodiment is not particularly limited, but may be 50% by mass or more and 95% by mass or less based on the total amount of the epoxy resin (A). preferable.
  • Such a content has the advantage that the film is easy to handle, has high transparency, and is easy to cure with ultraviolet light.
  • the content is more preferably 80% by mass or more and 90% by mass or less, and even more preferably 85% by mass or more and 90% by mass or less.
  • the resin composition of the present embodiment may further contain, as the epoxy resin (A), a hydrogenated bisphenol A type epoxy resin (a-3) in addition to the epoxy resin described above.
  • the refractive index can be made relatively small when used as an optical waveguide, and when used as a cladding layer, there is a difference in refractive index from the core layer. It has the advantage of being easier to attach.
  • the hydrogenated bisphenol A type epoxy resin (a-3) may be prepared by a known method, but a commercially available one can also be used.
  • "JER (registered trademark) YX8040” manufactured by Mitsubishi Chemical Corporation” "JER (registered trademark) YX8034” manufactured by Mitsubishi Chemical Corporation, etc. can be used.
  • the resin composition of the present embodiment contains hydrogenated bisphenol A type epoxy resin (a-3), its content is not particularly limited, but is 4% by mass or more and 10% by mass based on the total amount of epoxy resin (A). It is preferable that it is below. Such a content has the advantage that the above-mentioned refractive index can be more reliably reduced and it can be used as a cladding layer. A more preferable content is 5% by mass or more and 9% by mass or less.
  • the resin composition of the present embodiment may contain a hydroxyl group-containing epoxy resin (a-4) as the epoxy resin (A).
  • a-4 hydroxyl group-containing epoxy resin
  • the film is particularly easy to handle, and the film obtained from the resin composition of this embodiment has the advantage of having excellent adhesion to the base and substrate. be.
  • the hydroxyl group-containing epoxy resin (a-4) of the present embodiment is not particularly limited as long as it has a hydroxyl group.
  • the above-mentioned polyfunctional epoxy resin (a-1), bisphenol A type epoxy resin (a -2) and/or the hydrogenated bisphenol A type epoxy resin (a-3) are epoxy resins having a hydroxyl group, they correspond to the hydroxyl group-containing epoxy resin (a-4) in this embodiment.
  • the bisphenol A type epoxy resin (a-2) contains a hydroxyl group-containing epoxy resin (a-4), such as Mitsubishi Chemical Corporation's: 1001 and 1006FS, and DIC Corporation's: 1055, 4050, YD-011, YD-014 of Nippon Steel Chemical & Materials Co., Ltd., etc. can be used as the hydroxyl group-containing epoxy resin (a-4).
  • the hydroxyl group-containing epoxy resin (a-4) may be used alone or in combination of two or more.
  • the amount of hydroxyl groups derived from the hydroxyl group-containing epoxy resin (a-4) contained in the epoxy resin (A) of this embodiment is preferably 0.00050 mol/g or more. It is thought that this makes it possible to more reliably obtain the above-mentioned effects.
  • a more preferable amount of hydroxyl groups is 0.0010 mol/g or more.
  • the upper limit of the amount of hydroxyl groups is not particularly limited, but from the viewpoint that if the amount of hydroxyl groups is excessive, the water absorption rate increases and there is a risk of adversely affecting the subsequent long-term reliability, it is 0.0025 mol/g or less. It is preferable.
  • the amount of hydroxyl groups means the numerical value measured by the method described in the Example mentioned later.
  • the content of the hydroxyl group-containing epoxy resin (a-4) contained in the epoxy resin (A) of this embodiment is preferably 40% by mass or more and 90% by mass or less based on the total amount of the epoxy resin (A). . It is thought that this makes it possible to more reliably obtain the above-mentioned effects.
  • a more preferable content is 40% by mass or more and 80% by mass or less.
  • the content of the bisphenol A type epoxy resin (a-2) and the hydroxyl group content may overlap.
  • the resin composition of this embodiment may contain epoxy resins other than the above-mentioned epoxy resins.
  • epoxy resins other than the above-mentioned epoxy resins.
  • bifunctional epoxy resins eg, EG-200, CG-500, manufactured by Osaka Gas Chemical Co., Ltd.
  • EG-200, CG-500 manufactured by Osaka Gas Chemical Co., Ltd.
  • the content of epoxy resins other than the above-mentioned epoxy resins (a-1) to ((a-4) is 5% by mass or more based on the total amount of the epoxy resin (A). , preferably about 40% by mass or less.
  • the resin composition of this embodiment contains a photoacid generator (B) (curing agent).
  • the photoacid generator (B) is not particularly limited as long as it contains an antimony-based photoacid generator and can promote photocuring of the resin composition containing the epoxy resin (A).
  • Examples of the photoacid generator include antimony-based photoacid generators, boron-based photoacid generators, and the like.
  • the resin composition of the present embodiment can have a high storage modulus at 150°C when cured. By having such a high storage modulus after curing, deformation of the end face when used as an optical waveguide can be suppressed.
  • the photoacid generator is a polymerization initiator for ring-opening polymerization of the epoxy groups of each of the epoxy resins, and is a compound that can initiate the reaction with light.
  • the antimony-based photoacid generator that can be used in this embodiment, for example, "CPI-101A” manufactured by San-Apro Co., Ltd., "SP-170” manufactured by ADEKA Co., Ltd., etc. can be used.
  • the antimony-based photoacid generator the above-mentioned exemplified compounds may be used alone, or two or more types may be used in combination.
  • the photoacid generator (B) of the present embodiment may contain a photoacid generator other than the antimony-based photoacid generator, as long as the effects of the present invention are not impaired.
  • the content of the photoacid generator (B) in the resin composition of this embodiment is not particularly limited, but should be 0.2% by mass or more and 0.4% by mass or less based on the total amount of the epoxy resin (A). is preferred. Such a content has the advantage of having a high storage modulus at 150°C. A more preferable content is 0.25% by mass or more and 0.3% by mass or less.
  • the resin composition of the present embodiment may also contain additives such as an antioxidant, a leveling agent, a coupling agent (silane coupling agent), a flame retardant, and an inorganic filler.
  • additives such as an antioxidant, a leveling agent, a coupling agent (silane coupling agent), a flame retardant, and an inorganic filler.
  • the resin composition of this embodiment preferably contains an antioxidant.
  • the antioxidant is not particularly limited, and phenol-based antioxidants, phosphite-based antioxidants, sulfur-based antioxidants, and the like can be used. Among these, phenolic antioxidants are preferred.
  • Specific phenolic antioxidants include, for example, AO-20, AO-30, AO-40, AO-50, AO-60, AO-80 manufactured by Adeka Co., Ltd., and AO-80 manufactured by Sumitomo Chemical Co., Ltd. Examples include SUMILIZER GA-80.
  • the content of the antioxidant is preferably 5% by mass or less based on the total amount of the epoxy resin. Further, since the antioxidant does not need to be contained, it is preferably 0% by mass or more. That is, the content of the antioxidant is preferably 0% by mass or more and 5% by mass or less based on the total amount of the epoxy resin.
  • the resin composition according to the present embodiment as described above can reduce end face deformation due to component mounting under high temperature in an optical waveguide using the resin composition, and can suppress a decrease in connection reliability.
  • the resin composition of this embodiment preferably has excellent heat resistance in its cured product, and from the viewpoint of more reliably providing a high storage modulus, curing of the resin composition of this embodiment
  • the glass transition temperature (Tg) of the product is preferably in the range of 120°C or higher and 180°C or lower. It is considered that by doing so, it is possible to more reliably obtain an optical waveguide that has sufficient storage modulus and heat resistance and is less likely to deform. It is further preferable that the Tg is 130°C or more and 160°C or less.
  • the resin composition for an optical waveguide can be used as a material for a dry film used when manufacturing an optical waveguide.
  • the dry film for an optical waveguide according to another embodiment of the present invention is not particularly limited as long as it includes a layer made of the resin composition.
  • the dry film for an optical waveguide includes a layer made of a semi-cured product or a cured product of the resin composition (hereinafter also simply referred to as a resin composition layer).
  • the dry film of this embodiment may include a base film laminated on at least one surface of the resin composition layer.
  • a protective film may be laminated on the other surface of the resin composition layer.
  • the dry film for optical waveguides of this embodiment only needs to include the resin composition layer, and may include other layers in addition to the film base material and the protective film, or may include the film base material and the protective film. Not required.
  • the film base material is not particularly limited, and examples thereof include polyethylene terephthalate (PET) film, biaxially oriented polypropylene film, polyethylene naphthalate film, and polyimide film. Among these, PET film is preferably used.
  • the protective film is not particularly limited, and examples thereof include polypropylene films and the like.
  • the method for producing the dry film for optical waveguides of this embodiment is not particularly limited, and examples thereof include the following methods. First, a solvent or the like is added to the above-described resin composition for an optical waveguide to form a varnish, and the varnish is applied onto a film base material. Examples of this coating include coating using a comma coater or the like. Then, by drying this varnish, a resin composition layer is formed on the film base material. Furthermore, a protective film is laminated on this resin composition layer. Examples of the lamination method include a thermal lamination method.
  • the resin composition layer in this dry film for an optical waveguide is used as a material for the optical waveguide.
  • the dry film for optical waveguides may be used when manufacturing the core of the optical waveguide or when manufacturing the cladding, but it is preferable to use it for the cladding for the reasons already mentioned.
  • the dry film of this embodiment also has excellent handling properties.
  • the resin composition for an optical waveguide according to the present embodiment does not necessarily need to be used as a dry film, and may be used, for example, in the form of a varnish. Similar to the dry film for optical waveguides, this composition for optical waveguides may be used when manufacturing the core of the optical waveguide or when manufacturing the cladding. In this way, when an optical waveguide is manufactured using the resin composition for an optical waveguide and the dry film for an optical waveguide, an optical waveguide that is less prone to deformation of the end face even when subjected to heat treatment and has high connection reliability can be obtained.
  • the present invention also includes an optical waveguide formed from the above-described resin composition for an optical waveguide and the dry film for an optical waveguide.
  • the optical waveguide of this embodiment is an optical waveguide including a core layer and a cladding layer having a lower refractive index than the core layer, and the cladding layer and/or the core layer are made of the above-mentioned resin composition for optical waveguide. It is also characterized by being formed of a dry film.
  • the cladding layer is formed of the above-mentioned resin composition for optical waveguide or dry film.
  • the optical waveguide of this embodiment is difficult to cause end face deformation even under high temperatures and has high connection reliability, so it is very useful for industrial use.
  • symbol in FIG. 1 shows the following: 1 Dry film for cladding, 2 Dry film for core, 3 cladding, 3a undercladding, 3b overcladding, 4 core.
  • a cladding dry film and a core dry film are used to form the core and cladding, respectively.
  • the above-mentioned dry film for optical waveguide is used as the dry film for cladding.
  • a dry film 1 for cladding is laminated on the surface of a substrate 10 on which an electric circuit 11 is formed, and then the dry film 1 for cladding is laminated by irradiation with light such as ultraviolet rays and heating. harden.
  • the substrate 10 for example, a flexible printed wiring board in which an electric circuit is formed on one side of a transparent base material such as a polyimide film, a printed wiring board such as glass epoxy, etc. are used.
  • an underclad 3a is formed in a layered manner on the surface of the substrate 10 as shown in FIG. 1(b).
  • a mask in which a core pattern slit is formed is overlaid, and a mask that can be cured by light such as ultraviolet light is passed through the slit.
  • the exposure method may be a selective exposure method using a mask, or a direct writing method in which laser light is scanned and irradiated along the pattern shape.
  • the core dry film 2 the above-mentioned optical waveguide dry film may be used, but it is preferable to use a dry film having a higher refractive index than the cladding dry film 1.
  • the core dry film 2 is developed using a developer such as an aqueous flux cleaning agent to remove the resin in the uncured portions of the core dry film 2 that are not exposed to light.
  • a developer such as an aqueous flux cleaning agent to remove the resin in the uncured portions of the core dry film 2 that are not exposed to light.
  • the cladding dry film 1 is laminated to cover the undercladding 3a and the core 4. Then, by curing the clad dry film 1 by irradiating light or heating, an over clad 3b as shown in FIG. 1(f) is formed. In this way, an optical waveguide A is formed on the surface of the substrate 10, in which the core 4 is embedded in the cladding 3 consisting of the undercladding 3a and the overcladding 3b.
  • the optical waveguide A obtained in this manner can suppress deformation of the end face of the cladding layer due to high temperatures, reduce optical loss, and achieve excellent connection reliability even at high temperatures. Therefore, the substrate 10 on which such an optical waveguide A is formed is preferably used as a printed wiring board for optical transmission, and is preferably used for, for example, a mobile phone or a personal digital assistant.
  • the resin composition for an optical waveguide according to the first aspect of the present invention contains an epoxy resin (A) and a photoacid generator (B), and the epoxy resin (A) has three or more epoxy groups. It also contains a polyfunctional epoxy resin (a-1) having an epoxy equivalent of 250 g/eq or less and a bisphenol A epoxy resin (a-2), and the photoacid generator (B) is an antimony-based photoacid generator. It is characterized by containing.
  • the resin composition for optical waveguides according to the second aspect of the present invention is the resin composition for optical waveguides according to the first aspect, in which the epoxy resin (A) further contains hydrogenated bisphenol A type epoxy resin (a-3). Contains.
  • the content of the polyfunctional epoxy resin (a-1) is 10% by mass or more and 20% by mass or less based on the total amount of the epoxy resin (A).
  • a resin composition for an optical waveguide according to the first or second aspect is 10% by mass or more and 20% by mass or less based on the total amount of the epoxy resin (A).
  • the content of the hydrogenated bisphenol A epoxy resin (a-3) is 4% by mass or more and 10% by mass based on the total amount of the epoxy resin (A).
  • the following is a resin composition for an optical waveguide according to a second or third aspect.
  • the resin composition for optical waveguides according to the fifth aspect of the present invention is the resin composition for optical waveguides according to any one of the first to fourth aspects, which has a storage modulus of 100 MPa or more at 150° C. after curing. .
  • the resin composition for optical waveguides according to the sixth aspect of the present invention is the resin composition for optical waveguides according to any one of the first to fifth aspects, wherein the epoxy resin (A) contains a hydroxyl group-containing epoxy resin (a-4). It is a composition.
  • the amount of hydroxyl groups derived from the hydroxyl group-containing epoxy resin (a-4) contained in the epoxy resin (A) is 0.00050 mol/g or more.
  • the resin composition for optical waveguides according to the eighth aspect of the present invention is the resin composition for optical waveguides according to the sixth or seventh aspect, wherein the bisphenol A epoxy resin (a-2) contains a hydroxyl group-containing epoxy resin (a-4). It is a resin composition.
  • the content of the hydroxyl group-containing epoxy resin (a-4) is 40% by mass or more and 90% by mass or less based on the total amount of the epoxy resin (A).
  • the dry film according to the tenth aspect of the present invention includes a layer made of an uncured or semi-cured product of the resin composition for optical waveguide according to any one of the first to ninth aspects.
  • An optical waveguide according to an eleventh aspect of the present invention is an optical waveguide comprising a core layer and a cladding layer having a lower refractive index than the core layer, wherein the cladding layer is the optical waveguide according to any one of the first to ninth aspects. It is formed using a resin composition for wave paths.
  • ⁇ Test Example 1> ⁇ Preparation of resin composition for optical waveguide> The components were blended according to the composition (parts by mass) shown in Table 1 below, and the mixed solvent of MEK and toluene was adjusted to 55 parts by mass per 100 parts by mass of the resin, and heated to 50 to 80 °C. Mixed while heating. Next, resin varnishes of the resin compositions for optical waveguides of Examples 1 to 16 and Comparative Examples 1 to 4 were prepared by filtering with a membrane filter having a pore size of 0.5 ⁇ m and defoaming.
  • the resin composition varnish for optical waveguides of each example and comparative example was applied to a PET film manufactured by Toyobo Co., Ltd. (product number A4100) using a K control coater manufactured by Matsuo Sangyo Co., Ltd., and dried at 130°C for 10 minutes to a predetermined thickness.
  • a dry film with a resin layer thickness of 20 ⁇ m was obtained by thermally laminating a release film OPP-MA420 manufactured by Oji Special Paper.
  • Glass transition temperature (Tg) and storage modulus at 150°C The dry film of each Example and each Comparative Example was cut into a size of 10 mm x 40 mm and attached to a dynamic viscoelasticity measuring device (DMS6100 manufactured by Seiko Instruments Inc.). The test was conducted with a strain amplitude of 10 ⁇ m, a frequency of 10 Hz (sine wave), and a temperature increase rate of 5° C./min, and the calculated peak temperature of tan ⁇ was adopted as the glass transition temperature. Furthermore, the storage modulus (MPa) at 150° C. was also measured in the same manner using the measuring device.
  • DMS6100 dynamic viscoelasticity measuring device
  • an optical waveguide was formed using the dry films of each Example and each Comparative Example.
  • the dry films of Examples 1 to 10 and Comparative Examples 1 to 4 were used as the dry film for the cladding, and the dry film of Example 11 was used as the dry film for the core layer. Used as a film.
  • the dry film of Example 11 was used as the dry film for the cladding, and the dry film of the resin composition of Example 10 containing 0% by mass of YX8040 was prepared and used for the core layer.
  • the dry film for cladding Using the dry film for cladding, it was laminated onto a substrate that had been subjected to oxygen plasma treatment using a vacuum laminator "V-130" at 65° C. and 0.3 MPa. Then, the curable film for cladding was irradiated with ultraviolet light at 2 J/cm 2 using an ultra-high pressure mercury lamp, and after the release film was peeled off, it was heat-treated at 140°C for 30 minutes to form the under cladding with the dry film for cladding cured. Formed.
  • this core dry film was laminated on the surface of the underclad using a vacuum laminator "V-130" under the same conditions as above. After peeling off the release film, heat treatment was performed at 100°C for 15 minutes, a mask was placed on the film, and exposure was performed using an ultra-high pressure mercury lamp at a light intensity of 2 J/cm 2 , followed by heat treatment at 140°C for 13 minutes. Next, the unexposed portions of the dry film are dissolved and removed by developing using a water-based flux cleaning agent ("Pine Alpha ST-100SX" manufactured by Arakawa Chemical Co., Ltd.) adjusted to 55 ° C. as a developer. Furthermore, after finishing washing with water and air blowing, a core was formed by drying at 120° C. for 15 minutes.
  • a water-based flux cleaning agent (“Pine Alpha ST-100SX” manufactured by Arakawa Chemical Co., Ltd.) adjusted to 55 ° C. as a developer.
  • a dry film for cladding was laminated thereon using a vacuum laminator "V-130" at 80° C. and 0.3 MPa. After peeling off the release film, the curable film for cladding was heat-treated at 140°C for 20 minutes, and then the curable film for cladding was irradiated with ultraviolet light at 2 J/cm 2 using an ultra-high pressure mercury lamp, and heat-treated at 140°C for 30 minutes. The dry film was cured to form an overcladding, and an optical waveguide for evaluation testing was obtained.
  • V-130 vacuum laminator
  • the optical waveguide sample was cut into a size of 50 mm x 50 mm using a DAC552 manufactured by DISCO Co., Ltd. at a rate of 0.3 mm/sec so that the core was exposed.
  • the substrate sample on which the optical waveguide was laminated obtained above was heat-treated at 150°C for 1 hour, and a white confocal microscope manufactured by Lasertec Co., Ltd. was used to check the roughness of the surface of the optical waveguide substrate end surface where the core was exposed.
  • the amount of end face deformation ( ⁇ m) of the cladding layer was measured by observing the deformation of the cladding layer.
  • the cured product of the resin composition of the present invention has a high Tg and a storage modulus at 150°C, and even after heat treatment at a high temperature (150°C), it is possible to form an optical waveguide. It was confirmed that the amount of deformation of the end face of the (cladding) could be suppressed. Further, by comparing Example 11 with the dry films of other Examples, the resin composition of the present invention has a relatively low refractive index by containing hydrogenated bisphenol A type epoxy resin (a-3). It was also confirmed that it could be used suitably for cladding. Furthermore, from the results of Examples 9 and 10, it was found that the effect can be more reliably obtained by keeping the content of the hydrogenated bisphenol A epoxy resin (a-3) within a suitable range.
  • Blend amount (mass) of hydroxyl group-containing epoxy resin (a-4) ("jER (registered trademark) 1001" (hereinafter simply “1001"), "Epicote (registered trademark) 1006FS” (hereinafter simply "1006"))
  • the number of molecules (mol) of each epoxy resin contained in the resin composition was calculated by dividing the number of epoxy resins contained in the resin composition. Furthermore, since 1001 contains 2.1 hydroxyl groups in its skeleton and 1006 contains 5.5 hydroxyl groups in its skeleton, multiply these values by the number of molecules of each epoxy resin calculated earlier.
  • the amount of hydroxyl groups contained in the resin composition was calculated by adding up each of the obtained values and dividing the resulting value by the total amount of epoxy resin.
  • Example 14 it was found that by including the hydroxyl group-containing epoxy resin (a-4), the resin composition of the present invention further improves the handling properties of the film when used as a dry film and the substrate when used as an optical waveguide. It was found that the adhesion was excellent. Furthermore, according to the results of Examples 1 to 13 and Examples 15 to 16, when the amount of hydroxyl groups derived from the hydroxyl group-containing epoxy resin (a-4) was within an appropriate range, the film handling properties and adhesion properties were further improved. It was also confirmed that good results could be obtained.
  • the present invention has wide industrial applicability in technical fields related to optical waveguides and opto-electrical composite wiring boards.

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  • Optical Integrated Circuits (AREA)
  • Epoxy Resins (AREA)

Abstract

Un aspect de la présente invention concerne une composition de résine pour un guide d'ondes optique, la composition de résine contenant une résine époxy (A) et un générateur de photoacide (B). La résine époxy (A) contient : une résine époxy polyfonctionnelle (a-1) qui a au moins trois groupes époxy et un poids équivalent époxy inférieur ou égal à 250 g/éq ; et une résine époxy de type bisphénol A (a-2). Le générateur de photoacide (B) contient un générateur de photoacide à base d'antimoine.
PCT/JP2023/016252 2022-04-27 2023-04-25 Composition de résine pour guide d'ondes optique, et film sec et guide d'ondes optique l'utilisant Ceased WO2023210629A1 (fr)

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2019026774A (ja) * 2017-08-01 2019-02-21 株式会社Adeka 硬化性組成物、硬化物の製造方法、およびその硬化物
JP2020184091A (ja) * 2015-09-01 2020-11-12 パナソニックＩｐマネジメント株式会社 光導波路用組成物、光導波路用ドライフィルム、及び光導波路
JP2021031658A (ja) * 2019-08-29 2021-03-01 三菱ケミカル株式会社 光カチオン重合性組成物、光造形用組成物及び硬化物
JP2021161126A (ja) * 2020-03-30 2021-10-11 三菱ケミカル株式会社 活性エネルギー線重合性組成物、３次元造形用組成物及び硬化物

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2020184091A (ja) * 2015-09-01 2020-11-12 パナソニックＩｐマネジメント株式会社 光導波路用組成物、光導波路用ドライフィルム、及び光導波路
JP2019026774A (ja) * 2017-08-01 2019-02-21 株式会社Adeka 硬化性組成物、硬化物の製造方法、およびその硬化物
JP2021031658A (ja) * 2019-08-29 2021-03-01 三菱ケミカル株式会社 光カチオン重合性組成物、光造形用組成物及び硬化物
JP2021161126A (ja) * 2020-03-30 2021-10-11 三菱ケミカル株式会社 活性エネルギー線重合性組成物、３次元造形用組成物及び硬化物

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