WO2024204317A1 - 樹脂組成物、フィルム、フィルムセット、光導波路、光電気複合基板、および電子部品 - Google Patents

樹脂組成物、フィルム、フィルムセット、光導波路、光電気複合基板、および電子部品 Download PDF

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Publication number
WO2024204317A1
WO2024204317A1 PCT/JP2024/012202 JP2024012202W WO2024204317A1 WO 2024204317 A1 WO2024204317 A1 WO 2024204317A1 JP 2024012202 W JP2024012202 W JP 2024012202W WO 2024204317 A1 WO2024204317 A1 WO 2024204317A1
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Prior art keywords
resin
resin composition
film
resin layer
less
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PCT/JP2024/012202
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English (en)
French (fr)
Japanese (ja)
Inventor
裕馬 田中
健太 佐藤
由奈 松原
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Sumitomo Bakelite Co Ltd
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Sumitomo Bakelite Co Ltd
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Priority to JP2025511008A priority Critical patent/JPWO2024204317A1/ja
Priority to CN202480020325.8A priority patent/CN120936678A/zh
Publication of WO2024204317A1 publication Critical patent/WO2024204317A1/ja
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F32/00—Homopolymers and copolymers of cyclic compounds having no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system
    • C08F32/02—Homopolymers and copolymers of cyclic compounds having no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system having no condensed rings
    • C08F32/04—Homopolymers and copolymers of cyclic compounds having no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system having no condensed rings having one carbon-to-carbon double bond
    • 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
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/18—Manufacture of films or sheets
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/15—Heterocyclic compounds having oxygen in the ring
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L45/00—Compositions of homopolymers or copolymers of compounds having no unsaturated aliphatic radicals in side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic or in a heterocyclic ring system; Compositions of derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
    • C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
    • C08L79/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L87/00—Compositions of unspecified macromolecular compounds, obtained otherwise than by polymerisation reactions only involving unsaturated carbon-to-carbon bonds
    • 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
    • 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
    • H05K1/03—Use of materials for the substrate
    • 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
    • H05K3/00—Apparatus or processes for manufacturing printed circuits
    • H05K3/38—Improvement of the adhesion between the insulating substrate and the metal

Definitions

  • the present invention relates to a resin composition, a film, a film set, an optical waveguide, an optical/electrical composite substrate, and an electronic component.
  • optical/electrical composite substrate is one in which an optical waveguide is provided on a substrate.
  • optical waveguide technologies include those described in Patent Documents 1 to 3.
  • Patent Document 1 describes an optical waveguide formed by laminating a core layer made of a polymer and a clad layer made of a polymer on a substrate, characterized in that the core layer is sandwiched in a direction perpendicular to the surface of the substrate between clad layers having a smaller refractive index than the clad layers that sandwich the core layer in a direction parallel to the surface of the substrate.
  • the optical waveguide described in Patent Document 1 even if polyimide having large birefringence is used, an optical waveguide having small PDL, easy to fabricate, and low loss is provided, and further, it is described that the use of this waveguide can provide an optical integrated circuit and an optical module having excellent characteristics.
  • Patent Document 2 describes an opto-electrical hybrid board comprising a flexible circuit board in which electrical wiring having mounting pads is formed on the surface of an insulating layer, an element mounted on the mounting pad, and an optical waveguide laminated on the back surface side of the insulating layer, wherein the flexible circuit board is a flexible double-sided circuit board in which electrical wiring is also formed on the back surface of the insulating layer, and a metallic reinforcing layer is plated on at least the portion of the electrical wiring on the back surface side that corresponds to the mounting pad, and the optical waveguide is in contact with the metallic reinforcing layer.
  • an optical-electrical hybrid board According to the optical-electrical hybrid board described in Patent Document 2, a metallic reinforcing layer is adhered to an insulating layer of a flexible circuit board without an adhesive layer, and it is described that an optical-electrical hybrid board can be provided in which elements are properly mounted while suppressing deformation due to a pressure load when the elements are mounted by the metallic reinforcing layer.
  • Patent Document 2 describes a method of preparing a substrate having copper foil 21 formed on both sides of an insulating layer 1 made of a resin such as polyimide, and forming through holes 1a and via holes 1b for an optical path in the substrate (see paragraph 0023 of Patent Document 2).
  • Patent Document 2 also describes a flexible double-sided circuit board E on which a metallic reinforcing layer M is formed (see paragraph 0028 of Patent Document 2).
  • the flexible double-sided circuit board E includes the substrate.
  • Patent Document 2 describes that an undercladding layer 6 is formed on the back side of a flexible double-sided circuit board E in contact with a metal reinforcing layer M that covers the electrical wiring 2B on the back side, and describes that examples of a molding material for the undercladding layer 6 include a photosensitive resin and a thermosetting resin (see paragraph 0029 of Patent Document 2). According to Figures 4 to 6 of Patent Document 2, it can be seen that the molding material for the undercladding layer 6 is filled into a recess formed in the flexible double-sided circuit board E on which the metal reinforcing layer M is formed.
  • Patent Document 3 describes an optoelectronic wiring board that is formed by integrating a rigid section in which conductor circuits and insulating layers are laminated on both sides of a substrate with one or more bendable flex sections, wherein the rigid section is formed with external connection terminals for mounting optical elements and/or package substrates on which optical elements are mounted, and at least one of the flex sections is formed with optical wiring. According to the optoelectronic wiring board of Patent Document 3, it is described that large-volume information processing and high-speed information processing can be suitably performed without increasing the size of the wiring board.
  • Patent Document 3 describes that the rigid section has an optical signal transmitting region formed therein, and that the optical signal transmitting region is filled with a resin composition (see claims 4 and 5 of Patent Document 3). Furthermore, it describes that the optical signal transmitting region is formed so as to penetrate all of the substrates and insulating layers that make up the rigid section (see claim 6 of Patent Document 3).
  • Patent Document 3 describes a substrate 221 consisting of an optical waveguide film 250 and a surrounding resin layer (insulating layer) 221a, and describes that the resin layer 221a constitutes part of the optical signal transmitting regions 242a, 242b (see paragraph 0033 of Patent Document 3).
  • the manufacturing process for an optoelectronic composite substrate includes, for example, a process of integrating a substrate on which vias are formed with a film for optical waveguide cladding.
  • the vias formed in the substrate must be embedded with the optical waveguide cladding.
  • resin compositions and films that can be used for optical waveguide cladding are required to have properties that enable the optical waveguide cladding to be sufficiently embedded in the vias (hereinafter, "embedding ability" refers to the property of the degree to which the optical waveguide cladding can be embedded in the vias).
  • the present invention has been made in consideration of the above circumstances, and provides a resin composition and film that can produce an optical waveguide clad with improved embeddability.
  • the present invention provides the following resin compositions, films, film sets, optical waveguides, optical/electrical composite substrates, and electronic components.
  • a resin composition that can be used for an optical waveguide clad A resin composition, wherein a resin layer made of the resin composition has a flow rate of 6% or more and 200% or less, calculated by the following method 1.
  • Method 1 A sample is formed so that the thickness of the resin layer made of the resin composition is 100 ⁇ m, and the sample is cut into a circle with a diameter of 1 cm to obtain a sample for measuring the flow rate. The sample for measuring the flow rate is sandwiched between slide glasses and laminated in a laminator under the conditions of temperature: 100° C., pressure: 5.0 MPa, and time: 180 seconds. The area of the resin layer before and after lamination is measured, and the flow rate [%] is calculated by the following formula (I).
  • Flow rate [%] [(area of resin layer after lamination - area of resin layer before lamination) / area of resin layer before lamination] x 100 (I)
  • [2] The resin composition according to [1] above, wherein a cured product of the resin composition has a storage modulus E' at 100°C of 0.5 GPa or more and 5.0 GPa or less.
  • [3] The resin composition according to [1] or [2], wherein a cured product of the resin composition has a storage modulus E' at 200°C of 0.1 GPa or more and 3.0 GPa or less.
  • Method 2 A sample is formed so that the thickness of the resin layer is 100 ⁇ m, and the sample is cut into a circle with a diameter of 1 cm to obtain a sample for measuring the flow rate.
  • the sample for measuring the flow rate is sandwiched between slide glasses and laminated in a laminator under the conditions of temperature: 100° C., pressure: 5.0 MPa, and time: 180 seconds.
  • the area of the resin layer before and after lamination is measured, and the flow rate [%] is calculated by the following formula (I).
  • Flow rate [%] [(area of resin layer after lamination - area of resin layer before lamination) / area of resin layer before lamination] x 100 (I)
  • Flow rate [%] [(area of resin layer after lamination - area of resin layer before lamination) / area of resin layer before lamination] x 100 (I)
  • Flow rate [%] [(area of resin layer after lamination - area of resin layer before lamination) / area of resin layer before lamination] x 100 (I)
  • Flow rate [%] [(area of resin layer after lamination - area of resin layer before lamination) / area of resin layer before lamination] x 100 (I)
  • Flow rate [%] [(area of resin layer after lamination - area of resin layer before lamination) / area of resin layer before lamination] x 100 (I)
  • Flow rate [%] [
  • the device includes a base film, The film according to any one of [8] to [11] above, wherein the resin layer is provided on the base film.
  • the resin constituting the base film contains at least one or more selected from the group consisting of polyimide and polyethylene terephthalate.
  • a film set that can be used for an optical waveguide clad comprising: A first film and a second film, At least one of the first film and the second film is the film according to any one of [8] to [14].
  • An electronic component comprising the optical/electrical composite substrate according to [17] above.
  • the present invention provides a resin composition and film that can produce an optical waveguide clad with improved embeddability.
  • FIG. 1 is a cross-sectional view showing a schematic example of a structure of an optical/electrical composite substrate according to an embodiment of the present invention.
  • the optical/electrical composite substrate 200 has an optical waveguide 100 provided on a substrate 110.
  • the optical waveguide 100 has a first clad layer 20, a core layer 30, and a second clad layer 40 laminated in this order.
  • a mirror 50 on the light-emitting element side and a mirror 60 on the light-receiving element side are formed in the optical waveguide 100.
  • Vias 140 (140a, 140b) are formed in the substrate 110 (note that the vias 140 shown in Fig. 1 are buried in the first clad layer 20).
  • a light-emitting element 120 and a light-receiving element 130 are provided on the opposite side of the substrate 110 to the optical waveguide 100 side.
  • the substrate 110 on which the vias 140 are formed and a film for forming the first cladding layer 20 are laminated and integrated by heating and pressurizing.
  • the vias 140 need to be embedded in the first cladding layer 20.
  • the optical waveguide clad cannot be sufficiently embedded in a via formed in a substrate, and a recess may be generated on the surface of the optical waveguide clad opposite to the substrate side (i.e., the core layer side of the optical waveguide clad) or a void may be generated in the via. It was also found that, when the above-mentioned recess or void is generated in the optoelectronic composite substrate, an optical loss occurs at the interface of the recess or void.
  • the present invention has been made in consideration of the above circumstances, and provides a resin composition and a film that can provide an optical waveguide clad with improved embeddability.
  • the light propagation path in the photoelectric composite substrate 200 will be specifically described using Figure 1.
  • the light emitted from the light-emitting portion of the light-emitting element 120 passes through via 140a formed in the substrate 110, and is incident on the mirror 50 on the light-emitting element side, whereby it is transmitted through the core layer 30, and then is incident on the mirror 60 on the light-receiving element side, passes through via 140b formed in the substrate 110, and is incident on the light-receiving element 130.
  • the arrows in Figure 1 are a schematic representation of the propagation of light.
  • the process may include a step of exposing the optoelectronic composite board to high temperatures (e.g., 230°C to 270°C), such as a reflow soldering process.
  • high temperatures e.g., 230°C to 270°C
  • the optical waveguide may be thermally shrunk when the optoelectronic composite board is exposed to high temperatures. It has also been found that such thermal shrinkage of the optical waveguide may cause a positional shift of the mirror. It has also been found that when the mirror is misaligned, light cannot propagate along the expected optical path, and normal light propagation is not possible.
  • the resin composition of the present embodiment is a resin composition that can be used for an optical waveguide clad, and the flow rate of a resin layer made of the resin composition, calculated by method 1, is 6% or more and 200% or less.
  • Method 1 A sample is formed so that the thickness of the resin layer made of the resin composition is 100 ⁇ m, and the sample is cut into a circle with a diameter of 1 cm to obtain a sample for measuring the flow rate. The sample for measuring the flow rate is sandwiched between slide glasses and laminated in a laminator under the conditions of temperature: 100 ° C., pressure: 5.0 MPa, and time: 180 seconds.
  • Flow rate [%] [(area of resin layer after lamination - area of resin layer before lamination) / area of resin layer before lamination] x 100 (I)
  • the method for forming a sample in Method 1 so that the resin layer made of the resin composition has a thickness of 100 ⁇ m is not particularly limited, but examples thereof include the following method.
  • a method of laminating the film-like resin composition using a laminating machine so that the thickness of the resin layer is 100 ⁇ m to obtain a sample can be mentioned.
  • the film-like resin composition can also be cut to obtain a sample having a thickness of 100 ⁇ m.
  • the varnish-like resin composition may be applied to a substrate film and dried to obtain a film-like resin composition, and then a sample may be obtained by the method described above.
  • the method described in the examples is preferable as a method for forming a sample in Method 1 so that the resin layer made of the resin composition has a thickness of 100 ⁇ m.
  • the flow rate of the resin composition of this embodiment calculated by method 1 is preferably 10% or more, more preferably 13% or more, even more preferably 15% or more, and even more preferably 18% or more, from the viewpoint of further improving embeddability, and is preferably 190% or less, more preferably 180% or less, even more preferably 150% or less, even more preferably 100% or less, even more preferably 90% or less, even more preferably 80% or less, and even more preferably 70% or less, from the viewpoint of preventing contamination during the manufacture of the optical waveguide and adjusting the cladding layer of the optical waveguide to an appropriate thickness.
  • the flow rate of the resin composition can be adjusted to a desired range by, for example, adjusting the type of resin that constitutes the resin composition, the weight average molecular weight (Mw) and glass transition temperature, the content ratio of the components of the resin composition, etc.
  • the storage modulus E' at 100°C of the cured product made of the resin composition of this embodiment is preferably 0.5 GPa or more, more preferably 0.8 GPa or more, even more preferably 1.0 GPa or more, even more preferably 1.2 GPa or more, even more preferably 1.5 GPa or more, even more preferably 1.7 GPa or more, and from the viewpoint of further improving embeddability, it is preferably 5.0 GPa or less, more preferably 4.5 GPa or less, even more preferably 4.0 GPa or less, even more preferably 3.5 GPa or less, even more preferably 3.2 GPa or less.
  • the storage modulus E' at 200°C of the cured product made of the resin composition of this embodiment is preferably 0.1 GPa or more, more preferably 0.2 GPa or more, and even more preferably 0.3 GPa or more, from the viewpoint of further suppressing the thermal shrinkage of the optical waveguide, and the upper limit is not particularly limited, but may be, for example, 3.0 GPa or less, or 2.0 GPa or less.
  • the storage modulus E' at 100°C and 200°C of the cured product made of the resin composition of this embodiment can be adjusted to a desired numerical range by, for example, adjusting the type of resin constituting the resin composition, the weight average molecular weight (Mw) and glass transition temperature, the content ratio of the components of the resin composition, etc.
  • the glass transition temperature (Tg) of the cured product made of the resin composition of the present embodiment is, from the viewpoint of further suppressing thermal shrinkage of the optical waveguide, preferably 150° C. or higher, more preferably 160° C. or higher, and even more preferably 180° C. or higher, and the upper limit is not particularly limited, but is, for example, 400° C. or lower.
  • the glass transition temperature (Tg) means a glass transition temperature calculated from the top peak of tan ⁇ using a dynamic mechanical analyzer (DMA).
  • the storage modulus E' at 100° C., the storage modulus E' at 200° C., and the glass transition temperature (Tg) of the cured product made of the above-mentioned resin composition can be calculated by the method described in the Examples. Specifically, the cured product of the resin composition is heated from 30°C to 400°C under conditions of a nitrogen atmosphere, a frequency of 1 Hz, a tensile mode, a sample distance of 1 cm, a sample width of 1 cm, and a heating rate of 5°C/min using a dynamic viscoelasticity measuring device, and the storage modulus E' and tan ⁇ versus temperature are measured.
  • the storage modulus E' of the cured product of the resin composition at 100°C and 200°C is calculated.
  • the glass transition temperature (Tg) of the cured product of the resin composition is calculated from the top peak of the obtained tan ⁇ .
  • the cured product of the resin composition means a cured product in a state where the resin composition is completely cured (C stage).
  • a method for determining whether a resin composition is in a completely cured state for example, there is a method of confirming whether the increase or decrease in peak intensity derived from a functional group involved in the curing reaction (e.g., a CO group in a cyclic ether structure) is constant by Fourier transform infrared spectroscopy (FT-IR method).
  • the method for curing the resin composition is not particularly limited, and examples thereof include a method of heating the resin composition, a method of irradiating the resin composition with light, and a method of irradiating the resin composition with light while heating, but a preferred method is a method of heating the resin composition in air at 180° C. for 2 hours.
  • a preferred method for irradiating the resin composition with light is a method of exposing the resin composition to light using a high-pressure mercury lamp at an integrated light quantity of 1000 mJ/cm 2 .
  • the shape of the resin composition of this embodiment is not particularly limited, and examples include a film, membrane, varnish, sheet, etc.
  • the resin composition of this embodiment is preferably a semi-cured or uncured product, and more preferably a semi-cured product.
  • the components of the resin composition of the present embodiment are not particularly limited, but preferably contain a polyimide resin (A) and a compound having a cyclic ether structure (B), and more preferably contain a polyimide resin (A), a compound having a cyclic ether structure (B), and a curing agent (C).
  • the resin composition of the present embodiment preferably contains a resin (F) having a norbornene skeleton, and a compound (B) having a cyclic ether structure, and more preferably contains a resin (F) having a norbornene skeleton, a compound (B) having a cyclic ether structure, and a curing agent (C).
  • the content of polyimide resin (A) in the resin composition of this embodiment when the total content of the resin components in the resin composition is 100 parts by mass, is, from the viewpoint of further improving embeddability, preferably 20 parts by mass or more, more preferably 23 parts by mass or more, even more preferably 25 parts by mass or more, and even more preferably 28 parts by mass or more, and from the viewpoint of further improving embeddability, is preferably 80 parts by mass or less, more preferably 75 parts by mass or less, even more preferably 70 parts by mass or less, and even more preferably 65 parts by mass or less.
  • the polyimide resin (A) of this embodiment preferably contains an imide ring structure in the molecule from the viewpoint of suppressing voids due to volatile components.
  • the inventors believe that by containing an imide ring structure in the molecule, it is possible to suppress the generation of volatile components (e.g., moisture) when the resin composition is cured, and therefore it is possible to suppress voids due to volatile components in the vias.
  • the imidization rate of the polyimide resin (A) of the present embodiment is preferably 90% or more, more preferably 93% or more, even more preferably 95% or more, even more preferably 97% or more, even more preferably 98% or more, and even more preferably 99% or more.
  • the imidization rate of polyimide resin (A) means an imidization rate expressed by ⁇ IM/(IM+AM) ⁇ 100(%), where IM is the number of moles of imide groups contained in polyimide resin (A) and AM is the number of moles of amide groups contained in polyimide resin (A).
  • the imidization ratio can be determined, for example, from the area of a peak corresponding to an amide group and the area of a peak corresponding to an imide group in an NMR spectrum, etc. As another example, the imidization ratio can be determined from the area of a peak corresponding to an amide group and the area of a peak corresponding to an imide group in an infrared absorption spectrum, etc.
  • the polyimide resin (A) of the present embodiment preferably contains a fluorinated polyimide.
  • the fluorinated polyimide means a polyimide containing a fluorine atom.
  • the solubility in organic solvents is further improved, making it easier to obtain a varnish-like resin composition.
  • the amount (mass ratio) of fluorine atoms in the fluorinated polyimide is preferably 1 mass % or more, more preferably 3 mass % or more, even more preferably 5 mass % or more, and is preferably 30 mass % or less, more preferably 28 mass % or less, even more preferably 25 mass % or less.
  • the fluorinated polyimide of this embodiment preferably contains a structural unit represented by the following general formula (a):
  • X is a divalent organic group
  • Y is a tetravalent organic group
  • at least one of X and Y has a fluorine atom.
  • the divalent organic group of X and/or the tetravalent organic group of Y preferably contain an aromatic ring structure, and more preferably contain a benzene ring structure, from the viewpoint of further suppressing the thermal shrinkage of the optical waveguide.
  • both the divalent organic group X and the tetravalent organic group Y are fluorine atom-containing groups.
  • the divalent organic group of X and/or the tetravalent organic group of Y preferably have a structure in which 2 to 6 benzene rings are bonded via a single bond or a divalent linking group.
  • divalent linking group examples include an alkylene group, a fluorinated alkylene group, and an ether group.
  • the alkylene group and the fluorinated alkylene group may be linear or branched.
  • the divalent organic group for X has, for example, 6 to 30 carbon atoms.
  • the tetravalent organic group for Y has, for example, 6 to 20 carbon atoms.
  • each of the two imide rings is preferably a five-membered ring.
  • the fluorinated polyimide of this embodiment more preferably contains a structural unit represented by the following general formula (aa):
  • Y' represents a single bond or an alkylene group
  • X has the same meaning as X in general formula (a)
  • at least one of X and Y' has a fluorine atom.
  • the alkylene group of Y' may be linear or branched. It is preferable that some or all of the hydrogen atoms of the alkylene group of Y' are substituted with fluorine atoms.
  • the number of carbon atoms of the alkylene group of Y' is preferably 1 to 6, more preferably 1 to 4, and even more preferably 1 to 3.
  • the refractive index of the polyimide resin (A) of the present embodiment is preferably 1.58 or less, more preferably 1.56 or less, even more preferably 1.55 or less, and still more preferably 1.54 or less.
  • the lower limit is not particularly limited, but is, for example, 1.50 or more.
  • the refractive index of the polyimide resin (A) means a refractive index measured under conditions of 23° C. and 589 nm using an Abbe refractometer.
  • the weight average molecular weight (Mw) of the polyimide resin (A) of the present embodiment is, from the viewpoint of further suppressing the thermal shrinkage of the optical waveguide, preferably 5,000 or more, more preferably 7,000 or more, even more preferably 10,000 or more, even more preferably 30,000 or more, and even more preferably 40,000 or more, and from the viewpoint of further improving the solubility in organic solvents, is preferably 200,000 or less, more preferably 150,000 or less, even more preferably 130,000 or less, and even more preferably 110,000 or less.
  • the weight average molecular weight can be determined by gel permeation chromatography (GPC) using polystyrene as a standard substance.
  • the polyimide resin (A) of this embodiment can be obtained, for example, by (i) first synthesizing a polyamide by reacting (condensation polymerization) a diamine with an acid dianhydride, and then (ii) imidizing the polyamide (ring-closing reaction).
  • Specific reaction conditions can be, for example, known conditions.
  • Examples of diamines used as raw materials in synthesizing the polyimide resin (A) of the present embodiment include 2,2'-bis(trifluoromethyl)-4,4'-diaminobiphenyl, 2,2-bis[4-(4-aminophenoxy)phenyl]-1,1,1,3,3,3-hexafluoropropane, 3,4'-diaminodiphenyl ether (3,4'-ODA), 4,4'-diamino-2,2'-bis(trifluoromethyl)biphenyl (TFMB), 3,3',5,5'-tetramethylbenzidine, and 2,3,5,6-tetramethyl-1,4-phenylenediamine.
  • 2,2'-bis(trifluoromethyl)-4,4'-diaminobiphenyl 2,2-bis[4-(4-aminophenoxy)phenyl]-1,1,1,3,3,3-hexafluoropropane
  • Examples of acid dihydrates used as raw materials for synthesizing the polyimide resin (A) of the present embodiment include 4,4'-(hexafluoroisopropylidene)diphthalic dianhydride, 4,4'-oxydiphthalic dianhydride, pyromellitic dianhydride (PMDA), diphenylether-3,3',4,4'-tetracarboxylic dianhydride (ODPA), benzophenone-3,3',4,4'-tetracarboxylic dianhydride (BTDA),
  • Examples of such anhydrides include biphenyl-3,3',4,4'-tetracarboxylic dianhydride (BPDA), diphenylsulfone-3,3',4,4'-tetracarboxylic dianhydride (DSDA), diphenylmethane-3,3',4,4'-tetracarboxylic dianhydride, 2,2-bis(3,4-phthalic anhydride)propane,
  • the polyimide resin (A) of this embodiment may be a single type of polyimide resin, or may contain two or more types of polyimide resins.
  • the compound (B) having a cyclic ether structure of the present embodiment preferably contains at least one or more types selected from the group consisting of epoxy resins and oxetane compounds, and more preferably contains one or more types of epoxy resins.
  • the compound having a cyclic ether structure in the present embodiment can be a monomer, an oligomer, or a polymer in general, and its molecular weight and molecular structure are not particularly limited.
  • the resin component in the resin composition also includes the compound (B) having a cyclic ether structure.
  • the content of the compound (B) having a cyclic ether structure contained in the resin composition of this embodiment when the total content of the resin components in the resin composition is taken as 100 parts by mass, is preferably 20 parts by mass or more, more preferably 25 parts by mass or more, even more preferably 30 parts by mass or more, and even more preferably 35 parts by mass or more, from the viewpoint of further improving embeddability, and is preferably 80 parts by mass or less, more preferably 75 parts by mass or less, from the viewpoint of further improving embeddability.
  • the compound (B) having a cyclic ether structure of this embodiment preferably contains an alicyclic structure in the molecule.
  • the compound (B) having a cyclic ether structure contains an alicyclic structure in the molecule means that it contains an alicyclic structure in addition to the cyclic ether structure.
  • the alicyclic structure of this embodiment includes a condensed ring structure in which a cyclic ether and an aliphatic ring are condensed, and a spiro ring structure in which a cyclic ether and an aliphatic ring are bonded by a spiro bond atom.
  • the number of ring members in the alicyclic structure is not particularly limited, but is preferably a 4- to 10-membered ring, more preferably a 4- to 8-membered ring, even more preferably a 5- or 6-membered ring, and still more preferably a 6-membered ring.
  • the compound (B) having a cyclic ether structure in this embodiment preferably contains two or more cyclic ether structures in the molecule, and more preferably contains two or three cyclic ether structures in the molecule.
  • the compound (B) having a cyclic ether structure in this embodiment is preferably liquid at 23°C from the viewpoint of ease of handling when producing the resin composition.
  • the refractive index of the compound (B) having a cyclic ether structure of this embodiment is preferably 1.55 or less, more preferably 1.53 or less, and even more preferably 1.52 or less.
  • the lower limit is not particularly limited, but is, for example, 1.45 or more.
  • the refractive index of the compound (B) having a cyclic ether structure means a refractive index measured using an Abbe refractometer under conditions of 23° C. and 589 nm.
  • the compound (B) having a cyclic ether structure in this embodiment may be a compound having one type of cyclic ether structure, or may contain compounds having two or more types of cyclic ether structures.
  • the curing agent (C) of the present embodiment may be, for example, a thermal polymerization initiator, a photopolymerization initiator, an amine compound, or the like.
  • the content of the curing agent (C) contained in the resin composition of this embodiment is, when the total content of the resin components in the resin composition is 100 parts by mass, preferably 0.1 parts by mass or more, more preferably 0.3 parts by mass or more, even more preferably 0.5 parts by mass or more, even more preferably 0.7 parts by mass or more, even more preferably 1.0 parts by mass or more, and is preferably 10.0 parts by mass or less, more preferably 8.0 parts by mass or less, even more preferably 6.0 parts by mass or less, even more preferably 5.5 parts by mass or less.
  • the curing agent (C) of the present embodiment preferably contains a cationic polymerization initiator.
  • the cationic polymerization initiator include a thermal cationic polymerization initiator and a photo cationic polymerization initiator, and among these, a thermal cationic polymerization initiator is preferred.
  • the thermal cationic polymerization initiator includes, for example, a sulfonium salt type polymerization initiator, an iodonium salt type polymerization initiator, and the like, and preferably includes a sulfonium salt type polymerization initiator.
  • the photocationic polymerization initiator includes, for example, a sulfonium salt type polymerization initiator, an iodonium salt type polymerization initiator, and the like, and preferably includes a sulfonium salt type polymerization initiator.
  • the curing agent (C) of this embodiment may be a combination of a thermal cationic polymerization initiator and a photo cationic polymerization initiator.
  • the curing agent (C) of this embodiment preferably contains an imidazole-based compound.
  • An imidazole-based compound refers to a compound that contains an imidazole ring structure, such as a compound in which the hydrogen of imidazole is replaced by a hydrocarbon group or the like.
  • the curing agent (C) in this embodiment may be a single curing agent or may contain two or more curing agents.
  • the resin composition of the present embodiment further contains a surfactant (D).
  • the surfactant (D) includes, for example, a silicone-based surfactant, a fluorine-based surfactant, and the like, and preferably includes a silicone-based surfactant.
  • the surfactant (D) of the present embodiment may be a single surfactant, or may contain two or more surfactants.
  • the content of the surfactant (D) contained in the resin composition of this embodiment is preferably 0.01 parts by mass or more, more preferably 0.05 parts by mass or more, even more preferably 0.07 parts by mass or more, and is preferably 3.0 parts by mass or less, more preferably 1.0 parts by mass or less, even more preferably 0.7 parts by mass or less, even more preferably 0.5 parts by mass or less, even more preferably 0.3 parts by mass or less, when the total content of the resin components in the resin composition is 100 parts by mass.
  • the resin composition of the present embodiment may contain an organic solvent (E).
  • the resin composition of the present embodiment contains the organic solvent (E)
  • it can be made into a varnish-like resin composition.
  • Examples of the organic solvent (E) in this embodiment include acetone, methyl ethyl ketone, toluene, propylene glycol monomethyl ether, propylene glycol methyl ethyl ether, propylene glycol dimethyl ether, propylene glycol 1-monomethyl ether 2-acetate, diethylene glycol ethyl methyl ether, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate, benzyl alcohol, propylene carbonate, ethylene glycol diacetate, propylene glycol diacetate, propylene glycol monomethyl ether acetate, dipropylene glycol methyl-n-propyl ether, butyl acetate, ⁇ -butyrolactone, methyl lactate, ethyl lactate, and butyl lactate.
  • the organic solvent (E) in the present embodiment may be a single organic solvent, or may contain two or more organic solvents.
  • the concentration of the total solids (non-volatile components) in the resin composition is preferably 10% by mass or more, more preferably 20% by mass or more, even more preferably 30% by mass or more, and even more preferably 35% by mass or more, from the viewpoint of appropriately controlling the viscosity of the resin composition, and is preferably 60% by mass or less, more preferably 55% by mass or less, and even more preferably 50% by mass or less, from the viewpoint of sufficiently dissolving each component in the resin composition.
  • the content of the resin (F) having a norbornene skeleton contained in the resin composition of this embodiment is preferably 20 parts by mass or more and 95 parts by mass or less, more preferably 30 parts by mass or more and 90 parts by mass or less, and even more preferably 35 parts by mass or more and 85 parts by mass or less, from the viewpoint of further improving embeddability, when the total content of the resin components in the resin composition is 100 parts by mass.
  • the resin (F) having a norbornene skeleton preferably contains a structural unit represented by formula (1).
  • R represents a hydrogen atom, a hydroxyl group, or an organic group having 1 to 30 carbon atoms.
  • the organic group constituting R is, for example, any one selected from the group consisting of an alkyl group, an alkenyl group, an alkynyl group, an alkylidene group, an aryl group, an aralkyl group, an alkaryl group, a cycloalkyl group, and an organic group having a carboxyl group.
  • the organic group constituting R preferably excludes a group having a cyclic ether structure.
  • alkyl group examples include at least one selected from the group consisting of a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a neopentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, and a decyl group.
  • the alkenyl group may be, for example, at least one selected from the group consisting of an allyl group, a pentenyl group, a vinyl group, and the like.
  • the alkynyl group includes, for example, an ethynyl group.
  • the alkylidene group may be, for example, at least one selected from the group consisting of a methylidene group, an ethylidene group, and the like.
  • the aryl group may be, for example, at least one selected from the group consisting of a phenyl group, a naphthyl group, an anthracenyl group, and the like.
  • the aralkyl group may be, for example, at least one selected from the group consisting of a benzyl group, a phenethyl group, and the like.
  • the alkaryl group may be, for example, at least one selected from the group consisting of a tolyl group, a xylyl group, and the like.
  • the cycloalkyl group may, for example, be at least one selected from the group consisting of an adamantyl group, a cyclopentyl group, a cyclohexyl group, a cyclooctyl group, and the like.
  • the organic group having an alkyl group, an alkenyl group, an alkynyl group, an alkylidene group, an aryl group, an aralkyl group, an alkaryl group, a cycloalkyl group, and a carboxyl group may have one or more hydrogen atoms replaced with a halogen atom.
  • the halogen atom include fluorine, chlorine, bromine, and iodine.
  • R is preferably any one selected from the group consisting of a hydrogen atom and an alkyl group, more preferably any one selected from the group consisting of a hydrogen atom and an alkyl group having 1 to 10 carbon atoms, and even more preferably an alkyl group having 3 to 7 carbon atoms.
  • R when R is an alkyl group, the coatability of the resin composition can be further improved.
  • the resin (F) having a norbornene skeleton preferably contains a structural unit represented by formula (2).
  • X is a divalent organic group having 1 to 30 carbon atoms
  • Y is a group having a cyclic ether structure.
  • the divalent organic group having 1 to 30 carbon atoms is preferably a group containing an oxygen atom.
  • the divalent organic group having 1 to 30 carbon atoms preferably has 1 to 20 carbon atoms, more preferably has 1 to 10 carbon atoms, and even more preferably has 1 to 5 carbon atoms.
  • the group having a cyclic ether structure preferably includes at least one selected from the group consisting of a group containing an epoxy group and a group containing an oxetanyl group.
  • the structural unit represented by formula (2) preferably includes a structural unit represented by formula (2-1).
  • a represents an integer of 0 or more and 3 or less, and b represents an integer of 1 or more and 3 or less.
  • a is preferably 1 or 2, and more preferably 1.
  • b is preferably 1 or 2, and more preferably 1.
  • the resin (F) having a norbornene skeleton may contain structural units other than the structural units derived from a norbornene-based compound.
  • the other structural unit includes, for example, at least one selected from the group consisting of a structural unit derived from a maleimide-based compound and a structural unit derived from a compound having an ethylenic double bond, and preferably includes a structural unit derived from a maleimide-based compound.
  • the maleimide-based compound includes, for example, at least one selected from the group consisting of maleimide, N-cyclohexylmaleimide, and the like, and preferably includes N-cyclohexylmaleimide.
  • Resin (F) having a norbornene skeleton preferably contains a structural unit represented by formula (1) and a structural unit represented by formula (2), and more preferably contains a structural unit represented by formula (1) and a structural unit represented by formula (2-1).
  • the content of the structural units derived from a norbornene-based compound in the resin (F) having a norbornene skeleton is preferably 60 mol % or more, more preferably 70 mol % or more, even more preferably 80 mol % or more, even more preferably 90 mol % or more, even more preferably 95 mol % or more, even more preferably 98 mol % or more, and even more preferably 100 mol %, when the total of all structural units in the resin (F) having a norbornene skeleton is 100 mol %.
  • the resin (F) having a norbornene skeleton preferably contains a structural unit represented by formula (1), a structural unit represented by formula (2), and a structural unit derived from a maleimide compound, and more preferably contains a structural unit represented by formula (1), a structural unit represented by formula (2-1), and a structural unit derived from a maleimide compound.
  • the total content of the structural units derived from a norbornene compound and the structural units derived from a maleimide compound in the resin (F) having a norbornene skeleton, when the total of all structural units in the resin (F) having a norbornene skeleton is taken as 100 mol %, is preferably 60 mol % or more, more preferably 70 mol % or more, even more preferably 80 mol % or more, even more preferably 90 mol % or more, even more preferably 95 mol % or more, even more preferably 98 mol % or more, and even more preferably 100 mol %.
  • the refractive index of the resin (F) having a norbornene skeleton is preferably 1.55 or less, more preferably 1.54 or less, and even more preferably 1.53 or less, and the lower limit is not particularly limited, but may be, for example, 1.45 or more, or 1.48 or more.
  • the refractive index of the resin (F) having a norbornene skeleton is preferably 1.45 or more and 1.55 or less, more preferably 1.45 or more and 1.54 or less, and even more preferably 1.48 or more and 1.53 or less.
  • the refractive index of the resin (F) having a norbornene skeleton means a refractive index measured using an Abbe refractometer under conditions of 23° C. and 589 nm.
  • the weight average molecular weight (Mw) of the resin (F) having a norbornene skeleton is preferably 5,000 or more, more preferably 6,000 or more, and even more preferably 7,000 or more, from the viewpoint of further suppressing the thermal shrinkage of the optical waveguide, and is preferably 200,000 or less, more preferably 100,000 or less, and even more preferably 70,000 or less, from the viewpoint of further improving the solubility in organic solvents. From the viewpoint of further suppressing the thermal shrinkage of the optical waveguide and further improving the solubility in organic solvents, it is preferably 5,000 or more and 200,000 or less, more preferably 6,000 or more and 100,000 or less, and even more preferably 7,000 or more and 70,000 or less.
  • the weight average molecular weight (Mw) of the resin (F) having a norbornene skeleton can be determined by gel permeation chromatography (GPC) using polystyrene as a standard substance.
  • the resin (F) having a norbornene skeleton can be produced, for example, by a known method, and more specifically, can be produced by polymerizing monomers capable of forming each structural unit by any method.
  • the resin composition of the present embodiment may further contain, for example, a curing assistant, a leveling agent, a colorant, a storage stabilizer, a plasticizer, a filler, inorganic particles, a deterioration inhibitor, a wettability improver, an antistatic agent, etc.
  • the content of the other components is an appropriate amount.
  • the resin composition of this embodiment may not contain a photosensitizer such as a photocationic polymerization initiator.
  • the content of the photosensitizer in the resin composition of this embodiment is not particularly limited, but when the total content of the resin components in the resin composition is taken as 100 parts by mass, it may be, for example, less than 1.0 part by mass, less than 0.5 part by mass, less than 0.3 part by mass, less than 0.1 part by mass, or 0.0 part by mass.
  • the content of the (meth)acrylic resin in the resin composition of the present embodiment is preferably less than 50 mass%, more preferably less than 30 mass%, even more preferably less than 10 mass%, even more preferably less than 5 mass%, even more preferably less than 1 mass%, even more preferably less than 0.1 mass%, and even more preferably 0 mass%, when the total content of non-volatile components in the resin composition is taken as 100 mass%
  • the (meth)acrylic resin is a concept including both methacrylic resin and acrylic resin.
  • the total content of the polyimide resin (A) and the compound (B) having a cyclic ether structure in the resin composition of the present embodiment is, from the viewpoint of further improving embeddability, preferably 80% by mass or more, more preferably 85% by mass or more, even more preferably 90% by mass or more, even more preferably 95% by mass or more, even more preferably 98% by mass or more, and even more preferably 100% by mass, when the total content of the resin components in the resin composition is 100% by mass.
  • the total content of the polyimide resin (A) and the compound (B) having a cyclic ether structure in the resin composition of the present embodiment when the total content of all components in the resin composition is 100 mass%, is preferably 10 mass% or more, more preferably 20 mass% or more, even more preferably 30 mass% or more, even more preferably 35 mass% or more, even more preferably 50 mass% or more, even more preferably 70 mass% or more, even more preferably 80 mass% or more, even more preferably 85 mass% or more, even more preferably 90 mass% or more, even more preferably 95 mass% or more, and the upper limit is not particularly limited, but is, for example, 99 mass% or less.
  • the total content of the polyimide resin (A), the compound having a cyclic ether structure (B), the curing agent (C), the surfactant (D), and the organic solvent (E) in the resin composition of this embodiment is preferably 50% by mass or more, more preferably 60% by mass or more, even more preferably 70% by mass or more, even more preferably 80% by mass or more, even more preferably 90% by mass or more, even more preferably 95% by mass or more, and even more preferably 100% by mass, when the total content of all components in the resin composition is 100% by mass.
  • the total content of the resin (F) having a norbornene skeleton and the compound (B) having a cyclic ether structure in the resin composition of this embodiment is, when the total content of the resin components in the resin composition is taken as 100 mass%, from the viewpoint of further improving embeddability, preferably 80 mass% or more, more preferably 85 mass% or more, even more preferably 90 mass% or more, even more preferably 95 mass% or more, even more preferably 98 mass% or more, and even more preferably 100 mass%.
  • the total content of the resin (F) having a norbornene skeleton and the compound (B) having a cyclic ether structure in the resin composition of this embodiment when the total content of all components in the resin composition is 100 mass%, is preferably 10 mass% or more, more preferably 20 mass% or more, even more preferably 30 mass% or more, even more preferably 35 mass% or more, even more preferably 50 mass% or more, even more preferably 70 mass% or more, even more preferably 80 mass% or more, even more preferably 85 mass% or more, even more preferably 90 mass% or more, even more preferably 95 mass% or more, and the upper limit is not particularly limited, but is, for example, 99 mass% or less.
  • the total content of the resin having a norbornene skeleton (F), the compound having a cyclic ether structure (B), the curing agent (C), the surfactant (D), and the organic solvent (E) in the resin composition of this embodiment is preferably 50% by mass or more, more preferably 60% by mass or more, even more preferably 70% by mass or more, even more preferably 80% by mass or more, even more preferably 90% by mass or more, even more preferably 95% by mass or more, and even more preferably 100% by mass, when the total content of all components in the resin composition is 100% by mass.
  • the resin composition of the present embodiment can be obtained, for example, by mixing the respective components.
  • the film-like resin composition of the present embodiment can be obtained, for example, by applying a varnish-like resin composition onto a substrate film and drying it.
  • the film of the present embodiment is a film that can be used for an optical waveguide clad, and includes a resin layer, the flow rate of which, calculated by Method 2, is 6% or more and 200% or less.
  • Method 2 A sample is formed so that the resin layer is 100 ⁇ m thick, and the sample is cut into a circle with a diameter of 1 cm to obtain a sample for measuring the flow rate.
  • the sample for measuring the flow rate is sandwiched between slide glasses and laminated in a laminator under the conditions of temperature: 100° C., pressure: 5.0 MPa, and time: 180 seconds.
  • the area of the resin layer before and after lamination is measured, and the flow rate [%] is calculated according to the following formula (I).
  • Flow rate [%] [(area of resin layer after lamination - area of resin layer before lamination) / area of resin layer before lamination] x 100 (I)
  • the method for forming the sample so that the resin layer has a thickness of 100 ⁇ m in Method 2 is not particularly limited, but for example, a method of obtaining a sample by laminating films using a laminator so that the resin layer has a thickness of 100 ⁇ m can be mentioned.
  • the sample can also be obtained by cutting the resin layer so that the thickness of the resin layer is 100 ⁇ m.
  • the method described in the examples is preferable as a method for forming a sample in Method 2 so that the thickness of the resin layer is 100 ⁇ m.
  • the flow rate of the resin layer calculated by method 2 is preferably 10% or more, more preferably 13% or more, even more preferably 15% or more, and even more preferably 18% or more, from the viewpoint of further improving embeddability, and is preferably 190% or less, more preferably 180% or less, even more preferably 150% or less, even more preferably 100% or less, even more preferably 90% or less, even more preferably 80% or less, and even more preferably 70% or less, from the viewpoint of preventing contamination during the manufacture of the optical waveguide and adjusting the cladding layer of the optical waveguide to an appropriate thickness.
  • the flow rate of the resin layer can be adjusted to a desired numerical range by adjusting the type of resin constituting the resin layer, the weight average molecular weight (Mw) and glass transition temperature, the content ratio of the components constituting the resin layer, etc.
  • the storage modulus E' at 100°C of the cured product obtained by curing the resin layer is preferably 0.5 GPa or more, more preferably 0.8 GPa or more, even more preferably 1.0 GPa or more, even more preferably 1.2 GPa or more, even more preferably 1.5 GPa or more, even more preferably 1.7 GPa or more, and from the viewpoint of further improving embeddability, it is preferably 5.0 GPa or less, more preferably 4.5 GPa or less, even more preferably 4.0 GPa or less, even more preferably 3.5 GPa or less, even more preferably 3.2 GPa or less.
  • the storage modulus E' at 200°C of the cured product obtained by curing the resin layer is preferably 0.1 GPa or more, more preferably 0.2 GPa or more, and even more preferably 0.3 GPa or more, from the viewpoint of further suppressing thermal shrinkage of the optical waveguide, and the upper limit is not particularly limited, but may be, for example, 3.0 GPa or less, or 2.0 GPa or less.
  • the storage modulus E' at 100°C and 200°C of the cured product obtained by curing the resin layer can be adjusted to a desired numerical range by, for example, adjusting the type of resin constituting the resin layer, the weight average molecular weight (Mw) and glass transition temperature, the content ratio of the components constituting the resin layer, etc.
  • the glass transition temperature (Tg) of the cured product obtained by curing the resin layer is, from the viewpoint of further suppressing thermal shrinkage of the optical waveguide, preferably 150° C. or higher, more preferably 160° C. or higher, and even more preferably 180° C. or higher, and the upper limit is not particularly limited, but is, for example, 400° C. or lower.
  • the glass transition temperature (Tg) means a glass transition temperature calculated from the top peak of tan ⁇ using a dynamic mechanical analyzer (DMA).
  • the storage modulus E' at 100°C, the storage modulus E' at 200°C, and the glass transition temperature (Tg) of the cured product obtained by curing the resin layer of the above-mentioned film can be calculated by the method described in the Examples. Specifically, the cured product obtained by curing the resin layer is heated from 30°C to 400°C using a dynamic viscoelasticity measuring device under conditions of a nitrogen atmosphere, a frequency of 1 Hz, a tensile mode, a sample distance of 1 cm, a sample width of 1 cm, and a heating rate of 5°C/min, and the storage modulus E' and tan ⁇ versus temperature are measured.
  • the storage modulus E' at 100°C and 200°C of the cured product obtained by curing the resin layer is calculated.
  • the glass transition temperature (Tg) of the cured product obtained by curing the resin layer is calculated from the top peak of the obtained tan ⁇ .
  • the cured product obtained by curing the resin layer means a cured product in a state where the resin composition constituting the resin layer is completely cured (C stage).
  • a method for determining whether a resin composition is in a completely cured state for example, there is a method of confirming whether the increase or decrease in peak intensity derived from a functional group involved in the curing reaction (e.g., a CO group in a cyclic ether structure) is constant by Fourier transform infrared spectroscopy (FT-IR method).
  • the method for curing the resin layer is not particularly limited, and examples thereof include a method of heating the resin layer, a method of irradiating the resin layer with light, and a method of irradiating the resin layer with light while heating, but a preferred method is a method of heating the resin layer in air at 180° C. for 2 hours.
  • a preferred method for irradiating the resin layer with light is a method of exposing the resin layer to light using a high-pressure mercury lamp at an integrated light quantity of 1000 mJ/ cm2 .
  • the resin layer is preferably formed from the resin composition of this embodiment.
  • the resin layer of this embodiment is preferably semi-cured or uncured, and more preferably semi-cured.
  • the thickness of the resin layer in this embodiment is preferably 1 ⁇ m or more, more preferably 5 ⁇ m or more, even more preferably 10 ⁇ m or more, even more preferably 15 ⁇ m or more, and even more preferably 20 ⁇ m or more, from the viewpoint of further improving embeddability, and is preferably 150 ⁇ m or less, more preferably 100 ⁇ m or less, even more preferably 50 ⁇ m or less, even more preferably 40 ⁇ m or less, and even more preferably 30 ⁇ m or less, from the viewpoint of further improving the light propagation efficiency of the optical waveguide.
  • the film of this embodiment is preferably a dry film.
  • the thickness of the film in this embodiment is preferably 10 ⁇ m or more, more preferably 30 ⁇ m or more, even more preferably 50 ⁇ m or more, even more preferably 80 ⁇ m or more, even more preferably 100 ⁇ m or more, and is preferably 500 ⁇ m or less, even more preferably 300 ⁇ m or less, even more preferably 200 ⁇ m or less, even more preferably 150 ⁇ m or less, even more preferably 130 ⁇ m or less.
  • the film of the present embodiment preferably further includes a base film, and a resin layer is provided on the base film.
  • the base film may be, for example, a resin film.
  • the resin constituting the base film is not particularly limited, but it is preferable that the base film contains at least one or more types selected from the group consisting of polyimide and polyethylene terephthalate.
  • the thickness of the base film in this embodiment is preferably 10 ⁇ m or more, more preferably 15 ⁇ m or more, even more preferably 20 ⁇ m or more, preferably 30 ⁇ m or more, and is preferably 100 ⁇ m or less, more preferably 80 ⁇ m or less, even more preferably 60 ⁇ m or less, even more preferably 40 ⁇ m or less.
  • the substrate film of this embodiment may be subjected to surface treatment such as antistatic treatment and release treatment.
  • the film of the present embodiment may further include a cover film.
  • the cover film is preferably provided so as to be in direct contact with the resin layer.
  • the cover film is preferably provided on the surface of the resin layer opposite to the base film.
  • the cover film is not particularly limited, but for example, an OPP cover film can be used.
  • the film of this embodiment can be obtained, for example, by applying the varnish-like resin composition of this embodiment onto a substrate film and drying it.
  • application methods include direct application using various coater devices such as a pin coater, die coater, comma coater, curtain coater, etc., and printing methods such as screen printing.
  • the film set of this embodiment includes a first film and a second film, and at least one of the first film and the second film is the film of this embodiment.
  • both the first film and the second film are preferably the film of this embodiment.
  • the optical waveguide of this embodiment will be described with reference to FIG.
  • the optical waveguide 100 of this embodiment is an optical waveguide in which a first clad layer 20, a core layer 30, and a second clad layer 40 are laminated in this order, and at least one of the first clad layer 20 and the second clad layer 40 contains the resin composition of this embodiment.
  • both the first cladding layer 20 and the second cladding layer 40 contain the resin composition of this embodiment.
  • the resin composition of this embodiment contained in at least one of the first clad layer 20 and the second clad layer 40 may be a cured product, a semi-cured product, or an uncured product, but is preferably a cured product.
  • the first cladding layer 20 be on the substrate 110 side.
  • the preferred thicknesses of the first cladding layer 20 and the second cladding layer 40 are as follows.
  • the thickness of the first cladding layer 20 is preferably 1 ⁇ m or more, more preferably 3 ⁇ m or more, even more preferably 5 ⁇ m or more, even more preferably 8 ⁇ m or more, even more preferably 10 ⁇ m or more, even more preferably 15 ⁇ m or more, and even more preferably 20 ⁇ m or more, and from the viewpoint of further improving the light propagation efficiency of the optical waveguide, the thickness is preferably 150 ⁇ m or less, more preferably 100 ⁇ m or less, even more preferably 70 ⁇ m or less, even more preferably 50 ⁇ m or less, even more preferably 40 ⁇ m or less, and even more preferably 30 ⁇ m or less.
  • the thickness of the second cladding layer 40 is preferably 1 ⁇ m or more, more preferably 3 ⁇ m or more, even more preferably 5 ⁇ m or more, and even more preferably 8 ⁇ m or more, and is preferably 150 ⁇ m or less, more preferably 100 ⁇ m or less, even more preferably 70 ⁇ m or less, even more preferably 50 ⁇ m or less, even more preferably 40 ⁇ m or less, even more preferably 30 ⁇ m or less, and even more preferably 20 ⁇ m or less.
  • the material for forming the core layer 30 is not particularly limited, but may be, for example, a resin composition.
  • the resin for forming the core layer 30 may be, for example, a resin used for the core of a known optical waveguide, but preferably contains a cyclic olefin resin, and more preferably contains a norbornene resin.
  • the resin composition for forming the core layer 30 may contain an antioxidant, a photoacid generator, and the like.
  • the thickness of the core layer 30 is preferably 1 ⁇ m or more, more preferably 5 ⁇ m or more, even more preferably 10 ⁇ m or more, even more preferably 20 ⁇ m or more, even more preferably 30 ⁇ m or more, and is preferably 100 ⁇ m or less, more preferably 80 ⁇ m or less, even more preferably 60 ⁇ m or less, even more preferably 50 ⁇ m or less.
  • the core layer 30 may have a waveguide pattern formed therein.
  • Methods for forming the waveguide pattern include, for example, exposure, etching, and replication.
  • the optical waveguide 100 may have a mirror formed thereon, and a mirror 50 on the light-emitting element side and a mirror 60 on the light-receiving element side may be formed.
  • the mirror may be formed, for example, by forming an inclined surface by laser processing or the like.
  • the optical waveguide 100 may have other layers as long as they do not affect the good performance of the optical waveguide 100.
  • the optical and electrical composite substrate of this embodiment will be described with reference to FIG.
  • the optical/electrical composite substrate 200 includes a substrate 110 and an optical waveguide 100 provided on the substrate 110 .
  • Examples of the substrate 110 include a printed circuit board and a flexible substrate, and a flexible substrate is preferable.
  • the substrate 110 may have vias 140 formed therein.
  • the photoelectric composite substrate 200 may include a light-emitting element 120, a light-receiving element 130, etc.
  • the optical-electrical composite substrate 200 can be obtained, for example, by (i) forming a first clad layer 20 on a substrate 110, (ii) forming a core layer 30 on the first clad layer 20, and (iii) forming a second clad layer 40 on the core layer 30.
  • methods for forming each layer include methods in which films for forming each layer are laminated in order by roll lamination, vacuum roll lamination, flat plate lamination, vacuum flat plate lamination, atmospheric pressing, vacuum pressing, etc.
  • the electronic component of this embodiment includes the optical/electrical composite substrate of this embodiment.
  • Examples of the electronic components of this embodiment include electronic components in electronic devices such as mobile phones, game machines, router devices, WDM devices, personal computers, televisions, and home servers.
  • the obtained polyimide solution was poured into 1,000 g of methanol in a 5 L container while stirring to precipitate a polyimide resin. Thereafter, the solid polyimide resin was filtered using a suction filtration device and washed with 1,000 g of methanol. The solid polyimide resin was then dried at 100° C. for 24 hours using a vacuum dryer and further dried at 200° C. for 3 hours to obtain a powdered polyimide resin (A-1).
  • the weight average molecular weight (Mw) of the polyimide resin (A-1) measured by GPC was 51,000.
  • the polyimide resin (A-1) was measured by 1 H-NMR, and the imidization rate was calculated from the quantitative value of the amide peak relative to the peak of the aromatic ring of the polyimide, and the imidization rate was found to be 99% or more.
  • Polyimide resin (A-1) was dissolved in propylene glycol monomethyl ether acetate to a solid content of 25%, and then coated using an applicator to a film thickness of 30 ⁇ m, followed by drying in an oven at 100° C. for 10 minutes to obtain a polyimide coating film.
  • the refractive index of the obtained coating film was measured using an Abbe refractometer (manufactured by Atago Co., Ltd., product name: NAR-1T SOLID) under conditions of 23° C. and 589 nm, and the refractive index of the polyimide was 1.54.
  • a polyimide resin (A-2) was obtained by carrying out polymer synthesis in the same manner as in the synthesis of polyimide resin (A-1), except that the amount of 2,2'-bis(trifluoromethyl)-4,4'-diaminobiphenyl was changed to 68.9 g (0.215 mol).
  • the weight average molecular weight (Mw) of the polyimide resin (A-2) measured by GPC was 101,000
  • the imidization rate of the polyimide resin (A-2) measured by NMR was 99% or more
  • the refractive index of the polyimide resin (A-2) measured by an Abbe refractometer under conditions of 23°C and 589 nm was 1.54.
  • the polyimide resin (A-3) had a weight average molecular weight (Mw) of 48,000 as measured by GPC, an imidization rate of 99% or more as measured by NMR, and a refractive index of 1.55 at 23° C. and 589 nm as measured by an Abbe refractometer.
  • the weight average molecular weight (Mw) of polyimide resin (A-4) measured by GPC was 49,000, the imidization rate of polyimide resin (A-4) measured by NMR was 99% or more, and the refractive index of polyimide resin (A-4) measured by an Abbe refractometer under conditions of 23°C and 589 nm was 1.55.
  • the weight average molecular weight (Mw) of the norbornene structure-containing resin (A-6) measured by GPC was 50,000, and the refractive index of the norbornene structure-containing resin (A-6) measured by an Abbe refractometer under conditions of 23° C. and 589 nm was 1.50.
  • the vessel was sealed and reacted at 70°C for 16 hours.
  • the obtained solution was cooled to room temperature and then reprecipitated in a large amount of heptane to obtain a polymer precipitate.
  • the polymer was then filtered off using a suction filter, and the powder was washed with heptane and then dried in a dryer at 60° C. for 24 hours to obtain a resin (A-7) having a norbornene skeleton.
  • the weight average molecular weight (Mw) of the norbornene skeleton-containing resin (A-7) measured by GPC was 8,500, and the refractive index of the norbornene skeleton-containing resin (A-7) measured by an Abbe refractometer under conditions of 23° C. and 589 nm was 1.51.
  • C ⁇ Curing Agent (C)> (C-1) San-Aid SI-110 (manufactured by Sanshin Chemical Industry Co., Ltd., thermal cationic polymerization initiator) (C-2) San-Aid SI-150 (manufactured by Sanshin Chemical Industry Co., Ltd., thermal cationic polymerization initiator) (C-3) San-Aid SI-B3 (manufactured by Sanshin Chemical Industry Co., Ltd., thermal cationic polymerization initiator) (C-4) Curesol C11z (manufactured by Shikoku Kasei Co., Ltd., imidazole compound) (C-5) CPI-310B (manufactured by San-Apro Co., Ltd., photocationic polymerization initiator)
  • D ⁇ Surfactant (D)> (D-1) BYK-333 (BYK Japan Co., Ltd., silicone surfactant) (D-2) BYK-361 (BYK Japan Co., Ltd., acrylic polymer surfactant) (for comparison)
  • Examples 1 to 9, 19 to 22, Comparative Examples 1 and 2, and Reference Example 2 Preparation of resin composition
  • the raw materials formulated according to Tables 1, 2, and 4 were stirred at room temperature until the raw materials were completely dissolved to obtain a solution.
  • the solution was then filtered through a PTFE filter having a pore size of 0.2 ⁇ m to obtain the varnish-like resin compositions of Examples 1 to 9, 19 to 22, Comparative Examples 1 and 2, and Reference Example 2, respectively.
  • Ni catalyst solution 1.56 g (3.2 mmol) of Ni catalyst and 10 mL of dehydrated toluene were weighed in a 100 mL vial, a stirrer tip was inserted and the vial was sealed, and the Ni catalyst was thoroughly stirred to completely dissolve, to obtain a Ni catalyst solution. 1 mL of the Ni catalyst solution was accurately weighed with a syringe, quantitatively injected into the vial in which the above two types of norbornene were dissolved, and stirred at room temperature for 1 hour, whereupon a significant increase in viscosity was confirmed. At this point, the stopper was removed, 60 g of tetrahydrofuran (THF) was added and stirred to obtain a reaction solution.
  • THF tetrahydrofuran
  • acetic anhydride 18 g of hydrogen peroxide (concentration 30%), and 30 g of ion-exchanged water were added to a 100 mL beaker and stirred to prepare an aqueous solution of peracetic acid.
  • the entire amount of the aqueous solution of peracetic acid was added to the reaction solution and stirred for 12 hours to carry out reduction treatment of Ni.
  • the reaction solution after the treatment was transferred to a separatory funnel, and the lower aqueous layer was removed, and then 100 mL of a 30% aqueous solution of isopropyl alcohol was added and vigorously stirred. After the mixture was left to stand and completely separated into two layers, the aqueous layer was removed.
  • the oil layer was dropped into a large excess of acetone to reprecipitate the produced polymer, which was then separated from the filtrate by filtration, and then heated and dried for 12 hours in a vacuum dryer set at 60 ° C. to obtain a polymer for forming a core layer.
  • the molar ratio of each structural unit in the polymer for forming the core layer was identified by NMR measurement and found to be 50 mol% hexylnorbornene structural units and 50 mol% diphenylmethylnorbornene methoxysilane structural units.
  • the obtained core layer forming resin composition was applied to a release-treated PET film using an applicator so that the film thickness after drying would be 40 ⁇ m. After application, the film was placed in a 45 ° C. dryer for 5 minutes to completely remove the solvent to form a coating. The obtained coating was irradiated with ultraviolet light at an exposure dose of 100 mJ/cm 2 using a direct drawing exposure machine (manufactured by SCREEN Co., Ltd., product name: LI-9000) to create 20 lines and spaces with a length of 9 cm and a width of 50 ⁇ m. The film was then placed in a 150 ° C. oven for 30 minutes. When removed from the oven, it was confirmed that a clear waveguide pattern (multiple core parts) with a rectangular cross section appeared on the coating.
  • Examples 24 to 26 In the above-mentioned Examples 10 to 18, 23, and Comparative Example 3 (production of optoelectronic composite substrate), the first clad layer was laminated using a vacuum laminator, and then the entire first clad layer was exposed to light from a high-pressure mercury lamp at an integrated light quantity of 1000 mJ/ cm2.
  • the optoelectronic composite substrates of Examples 24 to 26 were obtained in the same manner as in Examples 10 to 18, 23, and Comparative Example 3, except that the first clad layer was laminated using a vacuum laminator and then exposed to light from a high-pressure mercury lamp at an integrated light quantity of 1000 mJ/cm2.
  • the films of Examples 1 to 9, 19 to 22 and Comparative Examples 1 and 2 were laminated with a laminator under the conditions of temperature: 30°C, pressure: 1.0 MPa, and time: 120 seconds so that the thickness of the resin layer formed by the resin composition was 100 ⁇ m, to obtain a sample. More specifically, two films were laminated to prepare two films with a resin layer thickness of 50 ⁇ m, and then the two films with a resin layer thickness of 50 ⁇ m were laminated to obtain a sample with a resin layer thickness of 100 ⁇ m. When obtaining the sample, the PET film and OPP cover film of the substrate were appropriately removed. The obtained sample was cut into a circle with a diameter of 1 cm to obtain a sample for measuring the flow rate.
  • the sample for measuring the flow rate was sandwiched between glass slides and laminated in a laminator (manufactured by Nikko Materials Co., Ltd., device name: CVP-600) under the conditions of temperature: 100°C, pressure: 5.0 MPa, and time: 180 seconds.
  • the area of the resin layer before and after lamination was measured, and the flow rate [%] was calculated by the following formula (I).
  • Flow rate [%] [(area of resin layer after lamination - area of resin layer before lamination) / area of resin layer before lamination] x 100 (I)
  • the obtained DMA measurement sample was heated from 30°C to 400°C under conditions of a nitrogen atmosphere, a frequency of 1Hz, a tensile mode, a sample distance of 1cm, a sample width of 1cm, and a heating rate of 5°C/min, using a dynamic viscoelasticity measuring device (manufactured by TA, product name: Q800), and the storage modulus E' and tan ⁇ versus temperature were measured. From the obtained storage modulus E', the storage modulus E' [GPa] of the cured product at 100°C and 200°C was read. In addition, the glass transition temperature (Tg) [°C] of the cured product was read from the top peak of the obtained tan ⁇ .
  • a 50 ⁇ m thick double-sided copper-clad laminate (CCL) with a 100 ⁇ m ⁇ via hole was prepared.
  • the OPP cover film of the films of Examples 1 to 9, 19 to 22 and Comparative Examples 1 and 2 was peeled off, and the films were attached to the CCL so that the resin layer formed by the resin composition was on the CCL side, and then lamination was performed using a laminator under the conditions of temperature: 100° C., pressure: 5.0 MPa, and time: 2 minutes.
  • the via holes of the obtained substrate were observed under a microscope, and samples that were filled without voids were evaluated as A, samples that were filled with some voids but had some voids were evaluated as B, and samples that were not filled were evaluated as C.
  • samples with a propagation loss of less than 1 dB were rated as A
  • samples with a propagation loss of 1 dB to 3 dB were rated as B
  • samples with a propagation loss of more than 3 dB were rated as C.
  • the mirror-processed optical waveguide sample was treated three times at a maximum temperature of 250 ° C. in an N2 reflow device, and the mirror angle (angle B) was measured again.
  • the change rate of the mirror angle before and after reflow was calculated from the following formula, and samples with a change rate of ⁇ 1% were evaluated as A, samples with a change rate of 1 to 3% were evaluated as B, and samples with a change rate of more than 3% were evaluated as C.
  • Mirror angle change rate [%] [(angle A - angle B) / angle A] x 100
  • the embeddability of all of the films of the examples was good. That is, it can be seen that the embeddability is improved according to the resin composition and film of the present embodiment.
  • the photoelectric composite substrates of the examples have a small mirror angle deformation ratio and can suppress thermal shrinkage. That is, it can be understood that the resin composition and film of the present embodiment can suppress thermal shrinkage of the optical waveguide.
  • First cladding layer 30 Core layer 40 Second cladding layer 50 Mirror on the light emitting element side 60 Mirror on the light receiving element side 100
  • Optical waveguide 110 Substrate 120
  • Light emitting element 130 Light receiving element 140a, 140b Via 200 Optoelectronic composite substrate

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