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WO2025105092A1 - Composition de résine pour guide d'ondes optiques, et film sec, guide d'ondes optique et substrat de boîtier de semi-conducteur l'utilisant - Google Patents

Composition de résine pour guide d'ondes optiques, et film sec, guide d'ondes optique et substrat de boîtier de semi-conducteur l'utilisant Download PDF

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Publication number
WO2025105092A1
WO2025105092A1 PCT/JP2024/036576 JP2024036576W WO2025105092A1 WO 2025105092 A1 WO2025105092 A1 WO 2025105092A1 JP 2024036576 W JP2024036576 W JP 2024036576W WO 2025105092 A1 WO2025105092 A1 WO 2025105092A1
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Prior art keywords
resin composition
mass
optical waveguide
curing catalyst
epoxy
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English (en)
Japanese (ja)
Inventor
麻稀 黒田
祐輔 浦岡
津 金
潤子 栗副
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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    • 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
    • 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

Definitions

  • the present invention relates to a resin composition for optical waveguides, as well as a dry film, optical waveguide, and semiconductor package substrate that use the same.
  • Optical fiber has traditionally been the mainstream transmission medium in the fields of long-distance and medium-distance communications in the FTTH (Fiber to the Home) and in-vehicle fields.
  • FTTH Fiber to the Home
  • high-speed transmission using light has become necessary even over short distances of less than 1m.
  • optical waveguide-type optical wiring boards are suitable because they allow high-density wiring (narrow pitch, branching, crossing, multi-layering, etc.), surface mounting, integration with electrical boards, and small-diameter bending, which are not possible with optical fiber.
  • optical waveguides are formed by forming a cladding layer, a core layer, etc., using a highly transparent resin material, exposing the layer to ultraviolet (UV) radiation, developing the layer, and then curing the resin. It has also been reported that a resin composition containing an epoxy compound, which has excellent light resistance, and a curing agent is used as the resin material for such optical waveguides (Patent Document 1).
  • the resin composition described in Patent Document 2 has excellent photocurability and light resistance, but is not a composition for optical waveguides.
  • the epoxy group-containing polyorganosiloxane compound contained in the resin composition does not have UV curability by itself, and the hydrogenated epoxy resin contained in the resin composition contains a large amount of aliphatic units, so when used for optical waveguides, there is a problem that the optical loss at a wavelength of 1310 nm becomes large.
  • the main objective of the present invention is to improve the above problems and provide a resin composition for optical waveguides that has low optical loss and is excellent in light resistance, developability, film handling properties, patterning properties, and curing properties, as well as a dry film and optical waveguide using the same.
  • the resin composition for optical waveguide contains an epoxy compound (A) and a cationic curing catalyst (B), the epoxy compound (A) contains an epoxy group-containing polyorganosiloxane compound (a1), the content of the polyorganosiloxane compound (a1) is 40 mass% or more relative to 100 mass% of the epoxy compound (A), and the cationic curing catalyst (B) is characterized by containing a curing catalyst (b1) having an anion species whose conjugated acid strength is equal to or greater than that of HSbF6 , and a curing catalyst (b2) having an anion species whose conjugated acid strength is lower than that of HSbF6 .
  • FIG. 1 is a schematic cross-sectional view illustrating one embodiment of a method for forming an optical waveguide using the resin composition of the present embodiment.
  • the resin composition for optical waveguide of this embodiment contains an epoxy compound (A) and a cationic curing catalyst (B).
  • the epoxy compound (A) contains an epoxy group-containing polyorganosiloxane compound (a1).
  • the content of the polyorganosiloxane compound (a1) is 40 mass% or more with respect to 100 mass% of the epoxy compound (A).
  • the cationic curing catalyst (B) contains a curing catalyst (b1) having an anion species whose conjugated acid strength is equal to or greater than that of HSbF6 , and a curing catalyst (b2) having an anion species whose conjugated acid strength is lower than that of HSbF6 .
  • the resin composition of this embodiment can suppress light loss (particularly light loss at a wavelength of 1310 nm) in the cured product. In addition, it is also excellent in light resistance, patterning properties, developability, film handling properties, and curing properties, making it extremely useful for industrial use.
  • a semiconductor package substrate that includes the optical waveguide.
  • the resin composition of this embodiment is for optical waveguides and can be used for both clad layers and core layers. However, because optical loss at a wavelength of 1310 nm occurs in the core, using the resin composition of this embodiment for the core layer can be more effective.
  • Epoxy compound (A) The epoxy compound (A) of this embodiment contains an epoxy group-containing polyorganosiloxane compound (a1). Furthermore, the epoxy compound (A) may contain an epoxy compound (a2) other than the polyorganosiloxane compound (a1). Each epoxy compound will be described below.
  • Epoxy group-containing polyorganosiloxane compound (a1) The epoxy group-containing polyorganosiloxane compound (a1) of the present embodiment is a compound having a siloxane bond as the main chain and containing an epoxy group.By using such an epoxy group-containing compound having a siloxane bond, it is possible to obtain a resin composition having excellent light resistance, patterning properties, developability, film handling properties, etc.
  • the epoxy group-containing polyorganosiloxane compound (a1) of the present embodiment may be, for example, a compound represented by the following formula (1).
  • R 1 to R 5 each independently represent a hydrogen atom, a monovalent organic group having 1 to 20 carbon atoms which may have a substituent, a group represented by the following formula (2), or a group represented by the following formula (3).
  • R 1 to R 5 may be the same group or different groups, but at least one of R 1 to R 5 is a group represented by the following formula (2) or (3).
  • R7 is a divalent organic group having 1 to 20 carbon atoms which may have a substituent.
  • R 8 is a divalent organic group having 1 to 20 carbon atoms which may have a substituent.
  • examples of the "monovalent organic group having 1 to 20 carbon atoms, which may have a substituent" include linear alkyl groups having 1 to 20 carbon atoms, branched alkyl groups having 1 to 20 carbon atoms, alkyl groups containing a cyclic structure having 1 to 20 carbon atoms, aromatic hydrocarbon groups having 1 to 20 carbon atoms, and heterocyclic groups having 1 to 20 carbon atoms.
  • alkyl groups such as methyl groups, ethyl groups, propyl groups, isopropyl groups, butyl groups, sec-butyl groups, tert-butyl groups, octyl groups, and cyclohexyl groups
  • aromatic functional groups such as phenyl groups, naphthyl groups, carbazole groups, and phenethyl groups
  • ether groups such as furanyl groups, and polyethylene glycol groups.
  • R 1 to R 5 are a hydrogen atom, a methyl group, a phenyl group, or the like.
  • examples of the "monovalent organic group having 1 to 7 carbon atoms" include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a cyclohexyl group, and a phenyl group.
  • R 6 in the formula (1) is preferably a methyl group or a phenyl group.
  • the "divalent organic group having 1 to 20 carbon atoms" includes a methylene group, an ethylene group, a propylene group, an isopropylene group, and a butylene group.
  • R 7 in the formula (2) is preferably a methylene group.
  • R 8 in the formula (3) is preferably a methylene group.
  • the epoxy equivalent of the epoxy group-containing polyorganosiloxane compound (a1) is not particularly limited, but is preferably 100 g/equivalent or more and 5000 g/equivalent or less. By having the epoxy equivalent within the above range, it is possible to create a uniform cured film and improve the crosslinking density.
  • a more preferable lower limit of the epoxy equivalent is 150 g/equivalent or more, more preferably 200 g/equivalent or more.
  • a more preferable upper limit is 2000 g/equivalent or less, and more preferably 1000 g/equivalent or less.
  • the "epoxy equivalent” is defined as "the mass of an epoxy resin (in this invention, an epoxy group-containing polyorganosiloxane) containing one equivalent of epoxy groups" and can be measured in accordance with JIS K7236.
  • the weight average molecular weight (Mw) of the epoxy group-containing polyorganosiloxane (a1) of this embodiment is not particularly limited, but is preferably 300 or more and 10,000 or less. Having a weight average molecular weight (Mw) within the above range has the advantage of excellent handleability.
  • a more preferred lower limit of the weight average molecular weight is 500 or more, and more preferably 700 or more. Also, a more preferred upper limit is 7,500 or less, and more preferably 5,000 or less.
  • the number average molecular weight (Mn) of the epoxy group-containing polyorganosiloxane (a1) of the present invention is not particularly limited, but is preferably 150 or more and 9000 or less. Having a number average molecular weight (Mn) within the above range has the advantage of excellent handleability.
  • a more preferred lower limit of the number average molecular weight is 250 or more, and even more preferred is 600 or more.
  • a more preferred upper limit is 6500 or less, and especially preferred is 4000 or less.
  • the weight average molecular weight (Mw) of the epoxy group-containing polyorganosiloxane can be measured by gel permeation chromatography (GPC).
  • epoxy group-containing polyorganosiloxanes (a1) may be used alone or in combination of two or more.
  • the epoxy group-containing polyorganosiloxane (a1) used in this embodiment is preferably solid at room temperature.
  • a polyorganosiloxane (a1) with a melting point of 50°C or higher This is thought to result in better film performance when made into a film.
  • the epoxy group-containing polyorganosiloxane (a1) of the present invention is not particularly limited as long as it is a polyorganosiloxane containing an epoxy group, but it is preferable that it has a cyclic siloxane structure in the polyorganosiloxane skeleton. It is believed that the epoxy group-containing polyorganosiloxane (a1) having a cyclic siloxane structure has the advantage of improving the impact resistance of the cured product.
  • the content of the epoxy group-containing polyorganosiloxane (a1) in the resin composition of this embodiment is 40% by mass or more relative to 100% by mass of the epoxy compound (A). If the content is less than 40% by mass, there is a risk that the suppression of light loss will be insufficient or that the heat resistance will decrease. A more preferred range of the content is 80% by mass or more.
  • the upper limit of the content of the epoxy group-containing polyorganosiloxane (a1) there is no particular limit to the upper limit of the content of the epoxy group-containing polyorganosiloxane (a1), and it may be 100% by mass, but from the viewpoints of the curability of the resin composition and the film performance (tackiness) when made into a film, it is preferably 100% by mass or less, and more preferably 95% by mass or less.
  • Epoxy compound (a2) other than polyorganosiloxane compound (a1) may contain an epoxy compound (a2) other than the epoxy group-containing polyorganosiloxane (a1) as the epoxy compound (A).
  • an epoxy compound (a2) include bisphenol A type epoxy compounds, hydrogenated bisphenol A type epoxy compounds, bisphenol AF type epoxy compounds, polyfunctional epoxy compounds, alicyclic epoxy compounds, novolac type epoxy compounds, and aliphatic type epoxy compounds.
  • the use of an epoxy compound that is solid at room temperature i.e., an epoxy compound with a melting point of about 50°C or higher
  • the use of an alicyclic epoxy compound or a polyfunctional epoxy compound has the advantage that the curing property is good.
  • the epoxy compound (a2) is preferably an epoxy compound having a weight average molecular weight of 1000 or more. This has the advantage of improving the film performance when made into a film. There is no particular upper limit to the weight average molecular weight, but from the viewpoint of compatibility with the polyorganosiloxane compound, it is preferably 4000 or less.
  • the bisphenol A type epoxy compound used in this embodiment may be a solid bisphenol A type epoxy compound or a liquid bisphenol A type epoxy compound.
  • the bisphenol A type epoxy compound may be prepared by a known method, but commercially available products can also be used.
  • solid products include Mitsubishi Chemical Corporation's: 1001, 1002, 1003, 1055, 1004, 1004AF, 1003F, 1004F, 1005F, 1004FS, 1006FS, and 1007FS.
  • Liquid products include DIC Corporation's "Epicron 850S” and Mitsubishi Chemical Corporation's "JER (registered trademark) 825.”
  • the hydrogenated bisphenol A epoxy compound used in this embodiment may be prepared by a known method, but commercially available products can also be used. Examples of commercially available products that can be used include "JER (registered trademark) YX8040” manufactured by Mitsubishi Chemical Corporation and "JER (registered trademark) YX8034” manufactured by Mitsubishi Chemical Corporation.
  • the bisphenol AF type epoxy compound used in this embodiment is a fluorine-containing epoxy subclass, and may be prepared by a known method, but a commercially available product may also be used.
  • a commercially available product may also be used.
  • "YX7760” manufactured by Mitsubishi Chemical Corporation may be used as a commercially available product.
  • the polyfunctional epoxy compound used in this embodiment is not particularly limited, but examples include aromatic epoxy compounds having two or more epoxy groups.
  • the polyfunctional epoxy compound may be prepared by a known method, but a commercially available product can also be used.
  • "VG3101" manufactured by Printec Co., Ltd. can be used as a commercially available product.
  • the alicyclic epoxy compound used in this embodiment is not particularly limited, but commercially available products can be used.
  • "EHPE-3150" manufactured by Daicel Chemical Industries, Ltd. can be used as a commercially available product.
  • the above-mentioned epoxy compounds (a2) may be used alone or in combination of two or more.
  • the content of the epoxy compound (a2) in the resin composition of this embodiment is preferably 5% by mass or more and 60% by mass or less, based on 100% by mass of the epoxy compound (A).
  • a more preferred range for the content is 5% by mass or more and 20% by mass or less.
  • the resin composition of the present embodiment contains a cationic curing catalyst (B).
  • the cationic curing catalyst (B) contains a curing catalyst (b1) having an anion species whose conjugate acid strength is equal to or greater than that of HSbF6 , and a curing catalyst (b2) having an anion species whose conjugate acid strength is lower than that of HSbF6 .
  • the resin composition of the present embodiment has sufficient curability (uniform UV curing is possible) and patterning properties.
  • the curing catalyst (b1) preferably contains an ionic photoacid generator having an anion species whose conjugate acid strength is equal to or greater than that of HSbF6 .
  • the curing catalyst (b2) preferably contains an ionic photoacid generator having an anion species whose conjugate acid strength is lower than that of HSbF6 , and more preferably contains an ionic photoacid generator having an anion species whose conjugate acid strength is equal to or less than that of HPF6 .
  • the curing catalyst (b1) contains at least one ionic photoacid generator selected from the group consisting of, for example, an ionic photoacid generator having (Rf) n PF 6-n - , an ionic photoacid generator having (Rx) n BX 4-n - , and an ionic photoacid generator having (Rx) n GaX 4 -n - .
  • the curing catalyst (b2) contains at least one ionic photoacid generator selected from the group consisting of, for example, an ionic photoacid generator having PF 6 - , an ionic photoacid generator having BF 4 - , an ionic photoacid generator having (Rf)SO 3 - , and an ionic photoacid generator having a sulfite ion.
  • Rf in (Rf) n PF 6-n - and (Rf)SO 3 - is a perfluoroalkyl group, and n in (Rf) n PF 6-n - is any number from 1 to 5.
  • the number of carbon atoms in Rf in (Rf) n PF 6-n - is, for example, 1 to 3, and when there are multiple Rfs, they may be the same or different.
  • the number of carbon atoms in Rf in (Rf)SO 3 - is, for example, 1 to 8.
  • Rx is a phenyl group in which some of the hydrogen atoms are substituted with halogen atoms or electron-withdrawing substituents.
  • the halogen atoms are fluorine atoms, chlorine atoms, bromine atoms, etc.
  • the electron-withdrawing substituents are, for example, trifluoromethyl groups, nitro groups, cyano groups, etc.
  • X is a halogen atom, and preferably a fluorine atom.
  • n is any number from 1 to 4.
  • the Rx may be the same or different from each other.
  • Rx is , for example , C6F5 , ( CF3 ) 2C6H3 , CF3C6H4 , or C6H3F2 , etc.
  • (Rx) nBX4 -n- is , for example, ( C6F5 ) 4B- , ( ( CF3 ) 2C6H3 ) 4B- , ( CF3C6H4 ) 4B- , ( C6F5 ) 2BF2- , C6F5BF3- or ( C6H3F2 ) 4B- , etc.
  • the cationic species in the ionic photoacid generator contained in the curing catalyst (b1) and the cationic species in the ionic photoacid generator contained in the curing catalyst (b2) include at least one selected from the group consisting of various aromatic oniums, more specifically, various aromatic diazoniums, aromatic haloniums, and aromatic sulfoniums.
  • the content of the curing catalyst (B) is preferably 1% by mass or more and 4% by mass or less relative to 100% by mass of the epoxy compound (A). It is believed that such a content makes it possible to more reliably obtain the effects described above (curability, patterning properties). A more preferred range for the content is 1% by mass or more and 2% by mass or less.
  • the content ratio of the curing catalyst (b1) to the curing catalyst (b2) is preferably 0.25 parts by mass or more and 2 parts by mass or less of the curing catalyst (b2) per part by mass of the curing catalyst (b1). This is believed to make it possible to more reliably obtain the effects (curability, patterning ability) described above.
  • 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 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, phenol-based antioxidants are preferable.
  • Specific phenol-based antioxidants are not particularly limited, and commercially available products can be used. Examples include AO-20, AO-30, AO-40, AO-50, AO-60, and AO-80 manufactured by Adeka Corporation, and SUMILIZER GA-80 manufactured by Sumitomo Chemical Co., Ltd.
  • the content of the antioxidant is preferably 5% by mass or less based on the total amount of the epoxy compound.
  • the antioxidant since the antioxidant does not have to be contained, it is preferably 0% by mass or more.
  • 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 compound.
  • the resin composition according to this embodiment has excellent light resistance, patterning properties, developability and curing properties, and also has excellent film performance (film handling properties) when made into a film.
  • the optical loss in the cured product is small, making it extremely useful as a material for optical waveguides.
  • the resin composition for an optical waveguide can be used as a material for a dry film used in producing an optical waveguide.
  • the dry film for 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 optical waveguide includes a layer made of a semi-cured or cured product of the resin composition (hereinafter also simply referred to as a resin composition layer).
  • the dry film of this embodiment may also include a substrate 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 substrate and protective film, and the film substrate and protective film are not essential.
  • the film substrate is not particularly limited, but examples 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, but examples include polypropylene film.
  • the method for producing the dry film for optical waveguides of this embodiment is not particularly limited, but examples thereof include the following methods. First, a solvent or the like is added to the resin composition for optical waveguides described above to form a varnish, and the varnish is applied to the film substrate. This application can be performed using a comma coater or the like. Then, the varnish is dried to form a resin composition layer on the film substrate. Furthermore, a protective film is laminated on the resin composition layer. Examples of the lamination method include a thermal lamination method.
  • the resin composition layer in this dry film for optical waveguides is used as a material for the optical waveguide.
  • the dry film for optical waveguides may be used when manufacturing the core of an optical waveguide or when manufacturing the clad, but is preferably used for the core because it can further suppress optical loss at a wavelength of 1310 nm.
  • the dry film of this embodiment has excellent light resistance, curing properties, and developability, and is also easy to handle.
  • the resin composition for optical waveguides according to this embodiment does not necessarily have to be used as a dry film, and may be used in the form of a varnish, for example.
  • This composition for optical waveguides may be used when manufacturing the core of an optical waveguide, as with a dry film for optical waveguides, or may be used when manufacturing a clad. In this way, when an optical waveguide is manufactured using the resin composition for optical waveguides and the dry film for optical waveguides, it is possible to obtain an optical waveguide that is unlikely to cause end face deformation even when subjected to heat treatment and has high connection reliability.
  • the present invention also includes an optical waveguide formed from the above-mentioned resin composition for optical waveguides and the dry film for optical waveguides. That is, the optical waveguide of this embodiment is an optical waveguide having a core layer and a clad layer having a lower refractive index than the core layer, and is characterized in that the clad layer and/or the core layer are formed from the above-mentioned resin composition for optical waveguides or dry film. In a preferred embodiment, the core layer is formed from the above-mentioned resin composition for optical waveguides or dry film.
  • the optical waveguide of this embodiment is highly useful for industrial use because it is less likely to cause end face deformation even at high temperatures and has high connection reliability.
  • a clad dry film and a core dry film are used to form the core and clad, respectively. Note that in the embodiment described below, the optical waveguide dry film described above is used as the core dry film.
  • a clad dry film 1 is laminated onto the surface of a substrate 10 on which an electric circuit 11 is formed, and then the clad dry film 1 is cured by irradiating it with light such as ultraviolet light or by heating.
  • the above-mentioned optical waveguide dry film may be used as the clad dry film 1, but it is preferable to use a dry film with a lower refractive index than the core dry film 2.
  • the core dry film 2 is laminated onto the surface of the undercladding 3a, and then a mask with slits of the core pattern is placed over it, and light capable of photocuring, such as ultraviolet light, is irradiated through the slits to expose the core dry film 2 to the core pattern.
  • the exposure method may be a selective exposure method using a mask, or a direct writing method in which a laser beam is scanned and irradiated along the pattern shape.
  • the core dry film 2 is developed using a developer such as an aqueous flux cleaner to remove the resin from the unexposed and uncured parts of the core dry film 2.
  • a core 4 with a predetermined core pattern is formed on the surface of the underclad 3a, as shown in Figure 1(d).
  • the clad dry film 1 is laminated so as to cover the underclad 3a and the core 4. Then, the clad dry film 1 is cured by irradiation with light or heating to form the overclad 3b as shown in FIG. 1(f). 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 clad 3 consisting of the underclad 3a and the overclad 3b.
  • the optical waveguide A thus obtained has the above-mentioned configuration, and thus has excellent light resistance and suppresses optical loss (particularly optical loss at a wavelength of 1310 nm). 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 applications such as CPO (Co-Packed-Optics) and optical transceivers.
  • CPO Co-Packed-Optics
  • the present invention also includes a semiconductor package substrate having the optical waveguide described above.
  • the resin composition for optical waveguide according to the second aspect of the present invention is the resin composition for optical waveguide according to the first aspect, in which the polyorganosiloxane compound (a1) has a structure represented by the following formula (1).
  • R7 is a divalent organic group having 1 to 20 carbon atoms which may have a substituent.
  • R 8 is a divalent organic group having 1 to 20 carbon atoms which may have a substituent.
  • the resin composition for optical waveguides according to the third aspect of the present invention is the resin composition for optical waveguides according to the first or second aspect, in which the content of the curing catalyst (B) is 1% by mass or more and 4% by mass or less relative to 100% by mass of the epoxy compound (A).
  • the resin composition for optical waveguide according to the fourth aspect of the present invention is a resin composition for optical waveguide according to any one of the first to third aspects, in which the content ratio of the hard curing catalyst (b1) to the curing catalyst (b2) is 0.25 parts by mass or more and 2 parts by mass or less of the curing catalyst (b2) per 1 part by mass of the curing catalyst (b1).
  • the fifth aspect of the present invention relates to a resin composition for an optical waveguide, which is any one of the first to fourth aspects of the resin composition for an optical waveguide, in which the epoxy compound (A) further contains an epoxy compound (a2) different from the polyorganosiloxane compound (a1).
  • the dry film according to the sixth aspect of the present invention is formed using the resin composition for optical waveguide according to any one of the first to fifth aspects.
  • the optical waveguide according to the seventh aspect of the present invention is formed using the resin composition for optical waveguide according to any one of the first to fifth aspects.
  • the semiconductor package substrate according to the eighth aspect of the present invention includes the optical waveguide according to the seventh aspect.
  • epoxy group-containing polyorganosiloxanes 1 to 3 were synthesized, and their epoxy equivalent, molecular weight, and 29Si -NMR were measured.
  • the respective measurement methods are as follows.
  • epoxy equivalent (epoxy equivalent) The epoxy equivalent was measured based on JIS K 7236.
  • This epoxy group-containing polyorganosiloxane 1 is a polyorganosiloxane having an alicyclic epoxy group represented by the formula (3) (wherein R 8 is a methyl group) as a cyclic siloxane structure, and containing a branched structure in the polysiloxane skeleton.
  • Epoxy Group-Containing Polyorganosiloxane 2 (Evaluation Results of Epoxy Group-Containing Polyorganosiloxane 2)
  • the epoxy group-containing polyorganosiloxane 2 thus obtained had a number average molecular weight of 1,300, a weight average molecular weight of 2,500, and an epoxy equivalent of 325 g/equivalent.
  • This epoxy group-containing polyorganosiloxane 2 is a polyorganosiloxane that has a glycidyl epoxy group represented by the following formula (4) as a cyclic siloxane structure and contains a branched structure in the polysiloxane skeleton.
  • Epoxy Group-Containing Polyorganosiloxane 3 (Evaluation Results of Epoxy Group-Containing Polyorganosiloxane 3)
  • the epoxy group-containing polyorganosiloxane 3 thus obtained had a number average molecular weight of 1,300, a weight average molecular weight of 2,500, and an epoxy equivalent of 325 g/equivalent.
  • This epoxy group-containing polyorganosiloxane 3 is a polyorganosiloxane that has, as a cyclic siloxane structure, a glycidyl epoxy group represented by the formula (4) and an alicyclic epoxy group represented by the formula (3) (wherein R8 is a methyl group), and that contains a branched structure in the polysiloxane skeleton.
  • ⁇ Curing catalyst (B)> (Curing catalyst (b1)) "CPI-310B”: San-Apro Co., Ltd., triarylsulfonium salt type photoacid generator, anion species B(C 6 F 5 ) 4 - "CPI-210S”: a triarylsulfonium salt type photoacid generator manufactured by San-Apro Co., Ltd., anion species (Rf) n PF 6-n - (Curing catalyst (b2)) "CPI-110P”: San-Apro Co., Ltd., triarylsulfonium salt type photoacid generator, anion species PF 6 - "IRGACURE250”: photoacid generator of diaryliodonium salt type, manufactured by BASF, anion species PF 6 -
  • Examples 1 to 13 and Comparative Examples 1 to 9 ⁇ Preparation of Resin Composition for Optical Waveguide>
  • the components were blended according to the blending compositions (parts by mass) shown in Tables 1 and 2 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 mixed while heating to 50 to 80° C. Next, the mixture was filtered through a membrane filter having a pore size of 0.5 ⁇ m and then degassed to prepare resin varnishes of the resin compositions for optical waveguides of Examples 1 to 13 and Comparative Examples 1 to 9.
  • a curable resin composition was prepared by mixing 2 parts by mass (solid content) of the curing catalyst (B) in total with 100 parts by mass of the epoxy resin component of each of the examples and comparative examples, and thoroughly mixing them.
  • the curable resin composition of each of the examples and comparative examples was applied to a thickness of 50 ⁇ m on a glass plate having a thickness of 2 mm using a film applicator, and a coating film was produced by irradiating UV of 2000 mJ/ cm2 at an illuminance of 700 mW/ cm2 using an electrodeless H bulb manufactured by Heraeus Co., Ltd., and a light resistance test was performed on this coating film under the following conditions.
  • the YI value (ASTM E313) after the light resistance test was measured. Since the smaller the YI value, the better the light resistance, the evaluation was performed according to the following criteria. 1 or less: Excellent More than 1, 2 or less: Good More than 2: Fail
  • the step tablets used were Stouffer Transmission Step Wedge PART #T2115.
  • an optical waveguide was formed using the dry films of each Example and Comparative Example.
  • the dry films of Examples 1 to 13 and Comparative Examples 1 to 9 were used as core dry films, and dry films having a smaller refractive index than the optical waveguides of Examples 1 to 13 and Comparative Examples 1 to 9 were prepared and used for the cladding layers.
  • the dry film for cladding was laminated onto a substrate that had been subjected to oxygen plasma treatment at 65°C and 0.3 MPa using a vacuum laminator "V-130.”
  • the curable film for cladding was then irradiated with ultraviolet light at 2 J/ cm2 using an ultra-high pressure mercury lamp, and after the release film was peeled off, the film was heat-treated at 140°C for 30 minutes to form an undercladding in which the dry film for cladding was cured.
  • a core dry film was used, and 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, the film was heat-treated at 100°C for 15 minutes, and exposed to a light amount of 2 J/ cm2 from an ultra-high pressure mercury lamp with a 7 ⁇ m wide mask placed on it, and then heat-treated at 140°C for 13 minutes.
  • the unexposed portion of the dry film was dissolved and removed by developing using a water-based flux cleaner ("Pine Alpha ST-100SX” manufactured by Arakawa Chemical Industries Co., Ltd.) adjusted to 55°C as a developer, and then finished washing with water and air blowing, followed by drying at 120°C for 15 minutes to form a core, and an optical waveguide for evaluation test was obtained.
  • a water-based flux cleaner (Pine Alpha ST-100SX" manufactured by Arakawa Chemical Industries Co., Ltd.) adjusted to 55°C as a developer, and then finished washing with water and air blowing, followed by drying at 120°C for 15 minutes to form a core, and an optical waveguide for evaluation test was obtained.
  • a dry film for cladding was laminated thereon using a vacuum laminator "V-130" at 80°C and 0.3 MPa. After the release film was peeled off and heat treatment was performed at 140°C for 20 minutes, the curable film for cladding was irradiated with ultraviolet light at 2 J/ cm2 from an ultra-high pressure mercury lamp and heat treatment was performed at 140°C for 30 minutes, forming an overcladding in which the dry film for cladding was cured, and an optical waveguide for evaluation testing was obtained.
  • V-130 vacuum laminator
  • the optical waveguide sample was cut to a size of 50 mm x 50 mm using a DAC552 manufactured by Disco Corporation at 0.3 mm/sec so that the core was exposed.
  • the optical loss at a wavelength of 1310 nm was measured using the optical waveguide sample manufactured above in the following manner.
  • Light from a 1310 nm LED light source was passed through an optical fiber with a core diameter of 9 ⁇ m and NA of 0.12, and silicone oil was injected into the end of the manufactured optical waveguide sample via matching oil (refractive index 1.505).
  • an optical fiber with a core diameter of 50 ⁇ m and NA of 0.21 was passed through the same matching oil, and the other side of the optical waveguide sample was connected to a power meter to measure the power (P1) when an optical circuit was inserted.
  • the power (P0) was measured by butting two similar optical fibers together in a state without an optical circuit.
  • the optical loss (1310 nm) was calculated from the measured value using the formula -10 log (P1/Po).
  • the comparative examples using resin compositions that do not satisfy the provisions of the present invention showed results inferior to those of the examples in at least some of the evaluation tests. Specifically, the patterning properties were inferior in comparative example 1, in which the curing catalyst (b2) was not used, and the light resistance, curing properties, developability, and film performance were not sufficient in comparative example 2, in which the curing catalyst (b1) was not used. Furthermore, comparative examples 3 to 8, in which the content of polyorganosiloxane compound (a1) was low, and comparative example 9, in which the polyorganosiloxane compound (a1) was not used, showed inferior light resistance and film performance, and also had large light loss.
  • the present invention has wide industrial applicability in technical fields related to optical waveguides, various optical devices, and the like.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Engineering & Computer Science (AREA)
  • Microelectronics & Electronic Packaging (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Epoxy Resins (AREA)

Abstract

Un aspect de la présente invention concerne une composition de résine pour un guide d'ondes optiques, la composition de résine comprenant des composés époxy (A) et des catalyseurs de durcissement cationiques (B). Les composés époxy (A) comprennent un composé polyorganosiloxane (a1) contenant un groupe époxy. La teneur en pourcentage du composé polyorganosiloxane (a1) est de 40% en masse ou plus par rapport à 100% en masse des composés époxy (A). Les catalyseurs de durcissement cationiques (B) comprennent un catalyseur de durcissement (b1) comprenant une espèce anionique à partir de laquelle un acide conjugué ayant une résistance qui est égale ou supérieure à la résistance de HSbF6 est obtenu, et un catalyseur de durcissement (b2) comprenant une espèce anionique à partir de laquelle un acide conjugué ayant une résistance qui est inférieure à la résistance de HSbF6 est obtenu.
PCT/JP2024/036576 2023-11-17 2024-10-11 Composition de résine pour guide d'ondes optiques, et film sec, guide d'ondes optique et substrat de boîtier de semi-conducteur l'utilisant Pending WO2025105092A1 (fr)

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Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20020165339A1 (en) * 2001-04-27 2002-11-07 Congji Zha Materials for optical applications
JP2005336421A (ja) * 2004-05-31 2005-12-08 Dow Corning Toray Co Ltd 活性エネルギー線硬化型オルガノポリシロキサン樹脂組成物、光伝送部材およびその製造方法
WO2013172406A1 (fr) * 2012-05-18 2013-11-21 シーメット株式会社 Composition de résine pour stéréolithographie optique
WO2018110297A1 (fr) * 2016-12-12 2018-06-21 株式会社Adeka Composition
JP2019085533A (ja) * 2017-11-10 2019-06-06 サンアプロ株式会社 硬化性組成物及びそれを用いた光学素子
JP2021059615A (ja) * 2019-10-02 2021-04-15 東京応化工業株式会社 硬化性組成物、硬化物、及び硬化物の形成方法
JP2022089280A (ja) * 2020-12-04 2022-06-16 サンアプロ株式会社 酸発生剤、硬化性組成物及びレジスト組成物
JP2022100721A (ja) * 2020-12-24 2022-07-06 三菱ケミカル株式会社 硬化性樹脂組成物及び硬化物

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20020165339A1 (en) * 2001-04-27 2002-11-07 Congji Zha Materials for optical applications
JP2005336421A (ja) * 2004-05-31 2005-12-08 Dow Corning Toray Co Ltd 活性エネルギー線硬化型オルガノポリシロキサン樹脂組成物、光伝送部材およびその製造方法
WO2013172406A1 (fr) * 2012-05-18 2013-11-21 シーメット株式会社 Composition de résine pour stéréolithographie optique
WO2018110297A1 (fr) * 2016-12-12 2018-06-21 株式会社Adeka Composition
JP2019085533A (ja) * 2017-11-10 2019-06-06 サンアプロ株式会社 硬化性組成物及びそれを用いた光学素子
JP2021059615A (ja) * 2019-10-02 2021-04-15 東京応化工業株式会社 硬化性組成物、硬化物、及び硬化物の形成方法
JP2022089280A (ja) * 2020-12-04 2022-06-16 サンアプロ株式会社 酸発生剤、硬化性組成物及びレジスト組成物
JP2022100721A (ja) * 2020-12-24 2022-07-06 三菱ケミカル株式会社 硬化性樹脂組成物及び硬化物

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