WO2004104059A1 - 硬化型樹脂組成物、光学部品および光導波路 - Google Patents
硬化型樹脂組成物、光学部品および光導波路 Download PDFInfo
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- WO2004104059A1 WO2004104059A1 PCT/JP2004/007405 JP2004007405W WO2004104059A1 WO 2004104059 A1 WO2004104059 A1 WO 2004104059A1 JP 2004007405 W JP2004007405 W JP 2004007405W WO 2004104059 A1 WO2004104059 A1 WO 2004104059A1
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Classifications
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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
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/20—Esters of polyhydric alcohols or phenols, e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(meth)acrylate
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B6/00—Light guides; Structural details of arrangements comprising light guides and other optical elements, e.g. couplings
- G02B6/10—Light guides; Structural details of arrangements comprising light guides and other optical elements, e.g. couplings of the optical waveguide type
- G02B6/12—Light guides; Structural details of arrangements comprising light guides and other optical elements, e.g. couplings of the optical waveguide type of the integrated circuit kind
- G02B6/13—Integrated optical circuits characterised by the manufacturing method
- G02B6/138—Integrated optical circuits characterised by the manufacturing method by using polymerisation
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- 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
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
- C08F222/102—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B6/00—Light guides; Structural details of arrangements comprising light guides and other optical elements, e.g. couplings
- G02B6/10—Light guides; Structural details of arrangements comprising light guides and other optical elements, e.g. couplings of the optical waveguide type
- G02B6/12—Light guides; Structural details of arrangements comprising light guides and other optical elements, e.g. couplings of the optical waveguide type of the integrated circuit kind
- G02B2006/12083—Constructional arrangements
- G02B2006/121—Channel; buried or the like
Definitions
- the present invention relates to a curable resin composition, an optical component, and an optical waveguide. More specifically, the present invention relates to a curable resin composition which forms a cured product having excellent heat resistance and a precisely controlled refractive index by light curing or Z and thermal curing, and a cured product formed therefrom. Optical components, and optical waveguides. Background art
- Optical parts using polymer materials include micro lens and microphone aperture lens end lens, Fresno lens, lens, lenticular lens, prism sheet, diffraction grating, aspheric lens, camera lens, eyeglass lens, etc.
- There are various optical lenses and optical communication parts such as optical fibers, optical waveguides, and optical switches.
- Refractive index control is important in any optical component, but in particular, in optical waveguides, the refractive index must be controlled precisely to three decimal places or less. Since precise control of the refractive index is affected not only by the polymer material but also by the method of forming the optical waveguide, many proposals have been made for the formation method as well as the polymer material for the optical waveguide.
- the main forming methods are categorized as follows.
- a polymer film (substrate) is impregnated with a monomer containing a photopolymerization initiator (the refractive index of the polymer after photopolymerization is smaller than that of the substrate), and then the cladding is made through a photomask. Irradiation is carried out only to cause a polymerization reaction. Then, an optical waveguide is formed by removing the monomer in the unirradiated portion (core portion) using a solvent or the like.
- Photolithography + RIE method A method in which an optical waveguide layer is formed by photolithography, a core is formed by dry etching, and an upper clad is applied and formed.
- Direct exposure method After forming the core by photolithography, the upper cladding How to apply and form parts.
- Pleating method A method in which an arbitrary portion of a polymer film is irradiated with energy such as light only through a photomask to a cladding portion to cause a chemical reaction, thereby changing a refractive index.
- Stamper method A method in which a recess is formed on the monomer (lower clad part) applied on the substrate using a stamper, and the recess is filled with a monomer for the core and cured, and finally the upper clad is formed. .
- the one that is expected to have high productivity and low cost is called the stamper method, and the method suitable for this forming method is a radical polymerizable atalylate 'monomer or optical Force thione polymerization type epoxy resin and the like.
- a fluorine-containing compound such as a fluorine-containing (meth) acrylate polymer or a homopolymer thereof or a copolymer of another (meth) acrylate polymer and a non-fluoropolyfunctional (meth) acrylate
- An active energy linear curable composition for an optical lens comprising a monomer and a component has been proposed (Japanese Patent Application Laid-Open No. 2001-74812).
- the non-fluorinated polyfunctional (meth) acrylates' monomers aliphatic or aromatic poly (meth) acrylates such as dicyclopentyl (meth) acrylate are exemplified.
- this proposal can realize a low refractive index of the cured product (optical lens), it has a problem that heat resistance such as heat decomposition resistance and coloring resistance at high temperatures is reduced.
- optical waveguides made of polymers with fluorinated polyimide as the main skeleton include:
- the present invention has been made to solve the above-mentioned problems of the conventional technology. That is, the present invention provides an optical component having excellent heat resistance such as thermal decomposition resistance ⁇ coloring resistance, and at the same time, a refractive index precisely controlled, and in particular, a curable resin suitable for forming an optical waveguide by a stamper method. It is intended to provide a composition.
- the expression “refractive index is precisely controlled” means that the variation in the refractive index of a plurality of cured products repeatedly formed by curing from the same curable resin composition is It indicates that control is performed within four decimal places, specifically, within the range of 0.005.
- the present inventors have continued extensive research on combinations of polymerizable monomers in order to achieve the above-mentioned object, and found that the above-mentioned object was achieved only when two specific polymerizable monomers were combined. We have found what we can achieve and arrived at the present invention. That is, the present invention
- the present invention is a cured product and an optical component, particularly an optical waveguide, formed by photo-curing and / or heat-curing the curable resin composition.
- the cured product of the curable resin composition of the present invention not only shares excellent heat resistance and a precisely controlled refractive index, but also has features such as low light loss and good stamper releasability. I have. Therefore, the curable resin composition of the present invention is a polymer material suitable for use in optical components such as various optical lenses and optical communication components, and particularly requires precise refractive index control. Most suitable as a polymer material for optical waveguides. Further, by utilizing the features of the cured product of the present invention, it can be applied to uses other than optical parts, for example, heat-resistant coating / scratch-resistant coating, and water-repellent coating. BRIEF DESCRIPTION OF THE FIGURES
- FIG. 1 is a process flow chart showing an example of a method for forming an optical waveguide using the curable resin composition of the present invention.
- component (A) a monomer having both a polycyclic alicyclic hydrocarbon skeleton and two or more terminal radical polymerizable groups (hereinafter referred to as component (A));
- component (B) a monomer having a perfluoroalkylene skeleton and two or more terminal radical polymerizable groups (hereinafter, referred to as component (B)), and
- component (C) Photopolymerization initiator or Z and thermal polymerization initiator (hereinafter referred to as component (C))
- the monomer which is the component (A) of the present invention comprises a polycyclic alicyclic hydrocarbon skeleton and two or more Has a terminal radical polymerizable group.
- the alicyclic hydrocarbon skeleton is a cyclic hydrocarbon skeleton that does not exhibit aromaticity.
- the alicyclic hydrocarbon skeleton includes monocyclic and bicyclic or more polycyclic, and in a broad sense, includes terpenes and steroids.
- it in order to further improve the heat resistance of the cured product, it must be a bicyclic or more polycyclic alicyclic hydrocarbon skeleton having a particularly bulky molecular structure. More preferably, it is a tricyclic or higher alicyclic hydrocarbon skeleton.
- the monomer having a monocyclic alicyclic hydrocarbon skeleton has insufficient heat resistance and cannot achieve the above-mentioned object of the present invention.
- a monomer having an aliphatic hydrocarbon skeleton which is a monomer having a hydrocarbon skeleton other than the alicyclic hydrocarbon skeleton, has insufficient heat resistance of a cured product, while a monomer having an aromatic hydrocarbon skeleton has a good heat resistance.
- the birefringence of the cured product caused by the aromatic ring is increased, and the heat resistance is also insufficient.
- the polycyclic alicyclic hydrocarbon skeleton may have an internal unsaturated bond such as a double or triple bond, and may have a substituent of a lower alkyl group having a relatively small number of carbon atoms. .
- the number of carbon atoms in each ring constituting the polycyclic alicyclic hydrocarbon skeleton carbon atoms of 3 to 12 are known, but chemically stable carbon atoms of 5 to 8 are preferable, and carbon atoms of 5 or Particularly preferred is a polycyclic alicyclic hydrocarbon skeleton composed of 6 rings.
- polycyclic alicyclic saturated hydrocarbon skeleton examples include bicyclo [2.1.1] hexane, bicyclo [4.1.0] heptane, and bicyclo [2.2.1] heptane.
- (Norpornan) bicyclo [3.2.1] octane, bicyclo [4.2.0] octane, bicyclo [4.3.0] nonane, bicyclo [4.4.0] decane
- the terminal radical polymerizable group of the monomer which is the component (A) of the present invention is located at the end of one molecule of the monomer and is irradiated with light in the presence of a photopolymerization initiator or a thermal polymerization initiator (component (C)). Or a terminal unsaturated bond group capable of undergoing radical polymerization by either heating.
- radical polymerizable groups specifically, (meth) a Cryloyloxy group, (meth) acrylylamide group, bull group (including aryl group and methacryl group.
- Ethyl group isopropyl group, butyl ester group, vinyl thioatenole group, vinyl ketone group , Butyl ester group, butyl amino group and the like.
- (meth) atalyloyloxy group ⁇ (meth) acrylamide group and the like are respectively referred to as both an attaryloy / reoxy group and a methacryloyloxy group, and both an acrylamide group and a metharylamide group.
- the monomer of component (A) must have at least two polymer groups selected from the group of terminal radical polymer groups described above: polycyclic alicyclic hydrocarbon skeleton and only one terminal radical Even if the monomer having a polymerizable group has an unsaturated bond in the skeleton, there is a large difference in the polymerizability between the terminal radical polymerizable group and the unsaturated bond in the skeleton. Since only the polymerization reaction occurs, the heat resistance of the cured product becomes insufficient.
- the preferred terminal radical polymerizable groups of the component (A) monomer are (meth) atalyloinoleoxy group and vinyl group,
- the monomer which is component (A) of the present invention must have at least two of these radically polymerizable groups.
- the two or more terminal radical polymerization groups of the monomer may be different or the same.
- a more preferred terminal radical polymerization group is a (meth) acryloyloxy group, and a tricyclic or higher polycyclic alicyclic hydrocarbon skeleton having two or more (meth) acryloyloxy groups.
- dimethyloltricyclodecane [5.2.
- the monomer that is the component (B) of the present invention has a perfluoroalkylene skeleton and at least two terminal radical polymerizable groups.
- the perfluoroalkylene skeleton is a skeleton structure in which all C—H bonds of an alkylene group are substituted with C—F bonds, and is generally called a perfluoroalkylene group.
- the perfluoroalkylene group has a general formula represented by one (CF 2 > n ), where n is preferably an integer in the range of 2 to 12, and more preferably an integer in the range of 2 to 8.
- the perfluoroalkylene group may have a lower perfluoroalkyl group as a side chain group. If the n-force is S13 or more, the heat resistance of the cured product is greatly reduced, which is not preferable.
- the terminal radical polymerizable group contained in the monomer as the component (B) of the present invention is the same as the radical polymerizable group listed for the monomer as the component (A).
- the monomer of component (B) must also have at least two polymer groups selected from the group of terminal radical polymer groups described above. With a monomer having only one terminal radical polymerizable group, the cured product does not have good heat resistance.
- the preferred terminal radical polymerizable group of the monomer of the component (B) is (meth) acryloyl, if selected from the curability and physical properties of the cured product. Oxy group and bur group.
- the two or more terminal radical polymerizable groups of the monomer may be different or the same.
- the radical polymerizable group is a (meth) atalyloyloleoxy group, and a monomer having two or more terminal (meth) acryloyloxy groups and having a skeleton of the above-mentioned perfluoroalkylene group is particularly preferable.
- a monomer having an atariloyloxyshethyl group directly (CF 2 ) n — (n 2 to 8)
- 2- (meth) ataliloyl A monomer having an oxoshetyloxycarbo group directly is a preferred monomer, and the former monomer has 2 to 8 carbon atoms and is a perfluoroalkylene mono ⁇ , ⁇ , bis (((meth) atalyloyloxymethyl) methyl) And perfluoroalkylene mono ⁇ , ⁇ , monobis (2- (meth) atari inoleoxyethynole) are particularly preferred monomers.
- perfluorotetramethylene-1- (4-methyloxymethyl) is esterified with (meth) acrylic acid or (meth) acrylic acid chloride to give perfluorotetramethylene monoester.
- 1,4-bis ((meth) atalyloyloxymethyl) is obtained.
- perfluorotetramethylene 1,4-dicarboxylic acid is esterified with 2-hydroxyethyl (meth) acrylate to form perfluorotetramethylene 1,4-bis. (2-(meta) acryloyloxysheciloxycarbo) is obtained.
- the photopolymerization initiator which is the component (C) of the present invention, is cured by the light irradiation. It is an essential component for curing the composition.
- photopolymerization initiator there is no compound limited to the present invention, and generally used photopolymerization initiators, i.e., acetophenones, benzophenones, diacetyls, benzyls, benzoins, benzoin ethers Compounds, benzyldimethyl ketanols, benzoylbenzoates, hydroxyphenol ketones, aminophenol ketones, etc., carbonyl compound photopolymerization initiators, thiuram sulfides, thioxanthones, etc. And organic phosphorous compound-based photopolymerization initiators such as acyl phosphoxides and acyl phosphinates. In the present invention, such various kinds of photopolymerization initiators are used alone or in combination of two or more kinds.
- the mixing ratio of the photopolymerization initiator (C) is 0.5 to 10% by weight, preferably 1 to 7% by weight, based on the total amount of the components (A) and (B). If the compounding ratio is less than 0.5% by weight, the photocurability becomes insufficient, and if it exceeds 10% by weight, the curing reaction becomes too abrupt and adversely affects the physical properties of the cured product.
- the thermal polymerization initiator which is another component (C) of the present invention, has a thermal decomposition temperature of about 30 ° C. or higher, preferably about 60 ° C., among thermal polymerization initiators that decompose by heat to generate radicals.
- a thermal polymerization initiator of at least ° C is used.
- examples of such a thermal polymerization initiator include organic peroxides that do not generate by-products such as gas and water, among compounds generally used as thermal polymerization initiators in conventional radical polymerization reactions.
- the use of a product is particularly preferred. It is not preferable to use a thermal polymerization initiator having a thermal decomposition temperature of less than about 30 ° C., since the curable resin composition of the present invention becomes unstable.
- Organic peroxides are classified, depending on their chemical structure, into alkyl or aryl'hydroxide peroxides, dialkyl or diaryl peroxides, alkyl peroxy acids and their esters, diasyl peroxides, ketones' peroxides, etc. Is done. In the present invention, any organic peroxide can be used.
- the mixing ratio of the thermal polymerization initiator (C) is 0.5 to 5% by weight, preferably 1 to 3% by weight, based on the total amount of the components (A) and (B). If the compounding ratio is less than 0.5% by weight, the thermosetting property becomes insufficient, and if it exceeds 5% by weight, the curing reaction becomes too rapid. It is not preferable because it adversely affects the physical properties of the cured product. In the present invention, one kind of such an organic peroxide is used alone, or two or more kinds are used in combination.
- the photopolymerization initiator and the organic peroxide which is a thermal polymerization initiator, are compounded alone or in combination, respectively. Even when they are combined, the mixing ratio of each is as described above.
- a monomer other than the component (A) and the component (B) of the present invention having at least one terminal radical polymerizable group at the terminal of the monomer molecule is blended as a reactive diluent. Is also good.
- the reactive diluent is added when it is necessary to adjust the viscosity and curability of the curable resin composition of the present invention or the physical properties of the cured product.
- Such a monomer has the same terminal radical polymerizable group (meth) atalyloyloxy group or butyl group in order to make the photocurability and thermosetting properties equivalent to those of the component (A) and the component (B).
- Monomers are preferred, and monomers having a (meth) acryloylonoxy group are more preferred. Monomers having two or more (meth) atalyloyloxy groups are more preferred. Specifically, it is a divalent or higher polyvalent (meth) acrylate ester such as an aliphatic or monocyclic alicyclic monomer.
- the mixing ratio of the reactive diluent is 20% by weight or less based on the total amount of the components (A) and (B). If the compounding ratio exceeds 20% by weight, the heat resistance of the cured product is greatly reduced, which is not preferable.
- a polymerization inhibitor In the curable resin composition of the present invention, a polymerization inhibitor, an antifoaming agent, a light stabilizer, a heat stabilizer, a leveling agent, Small amounts of additives such as coupling agents and antistatic agents may be added.
- UV irradiation dose is also different depending component structure of curable resin composition of the present invention, typically, 1, 0 0 0-5 is 0 0 O mj Z cm 2.
- the organic peroxide is cured by heating to a temperature higher than the thermal decomposition temperature. Therefore, the heating temperature depends on the kind of the organic peroxide to be blended.
- the heating time is usually 10 to 60 minutes.
- photocuring In the case of a combination of photocuring and thermal curing, in which a photopolymerization initiator and an organic peroxide are combined, it is common to first cure by photoirradiation with ultraviolet light and then heat to complete the curing. It is a target. Compared to thermal curing, photocuring is more excellent in handleability, curing speed, and the like. Therefore, in the curable resin composition of the present invention, it is preferable to employ photocuring, that is, ultraviolet curing.
- the cured product formed by photo-curing and / or heat-curing the curable resin composition of the present invention has excellent heat resistance such as heat decomposition resistance and coloring resistance, as well as precise control of the refractive index. Have been. Therefore, the curable resin composition of the present invention is suitable for forming the optical component described above. Further, when the curable resin composition of the present invention is used to form an optical waveguide by a photo-curing stamper method, the formability of the stamper method is good, and the formed optical waveguide is Since it also has a characteristic of low loss, it is particularly suitable for forming an optical waveguide.
- the optical waveguide of the present invention can be formed by a known method such as the photolithography + RIE method or the direct exposure method.
- the curable resin composition of the present invention may be used only for one of the cladding part 2 (lower part 2a; upper part 2b) and core part 3 of the optical waveguide 1 (see FIG. 1 (F)). It is preferred that both are used.
- the optical waveguide is formed such that the refractive index of the cladding is slightly lower than that of the core.
- the clad portion and the core portion are formed by slightly changing the mixing ratio of the monomer of the component (A) and the monomer of the component (B).
- the refractive index of the portion can be adjusted.
- a curable resin composition 12a for the lower clad portion is formed on a substrate 10 by a spin coating method, a doctor plate method, or the like. After application by such a known method, the convex stamper 11 is pressed. Then, in the pressed state, by light curing or heat curing, The lower clad portion 2a having the core engraved portion 13 is formed (FIGS.
- the engraved portion 13 is filled with a hardening lubricating composition 14 for the core portion, and while the flat plate 15 is pressed, the core portion 3 is cured by light or heat.
- the curable resin composition 12b for the upper cladding is applied, and while the substrate 16 is pressed, it is cured by light or / and heat.
- the upper cladding 2b is formed (Fig. 1
- the heat resistance and the refractive index precision control '14 were measured by the test method described in 7.
- the curable resin composition was injected between two glass plates (0.7 mm thick, dimensions 10 cm x 10 cm) held at a spacing of 20 soil 1 ⁇ m with spacer tape in between. Thereafter, the glass surface was irradiated with UV light until the amount of UV irradiation on the glass surface reached 3,000 mJZ cm 2 .
- the temperature was raised from room temperature to 250 ° C at a heating rate of 10 ° C using a TG-DTA measuring device (manufactured by Seiko Instruments Inc., Model 220).
- the thermogravimetric loss rate at the time of reaching C was measured, and the result was measured as heat resistance.
- the degree of coloring of the test piece after the measurement was visually determined.
- a resin film light-cured from the same curable resin composition was repeatedly prepared five times, and the center of each cured resin film was prepared.
- the refractive index of each part was measured, and the variation in the refractive index was calculated.
- the refractive index is measured using a prism coupler (Metricon: Model 2010) at 23 ° C according to the prism coupling method up to 4 significant figures after the decimal point. It was measured.
- thermogravimetric reduction rate of this photocurable resin film in a heat resistance test was 1% or less, indicating excellent heat resistance. No coloring was observed on the test piece after the heat resistance test.
- the refractive index variation was 1.4923 ⁇ 0.0003, indicating extremely excellent refractive index precision controllability.
- a curable resin composition (1) was prepared by mixing the same components as in Example 1 except for using OOO g.
- thermogravimetric loss rate in the heat resistance test was extremely large at 30%, and the test piece was colored yellow.
- Example 1 In place of perfluorooctamethylene-1,8-bis (atalyloyloxymethyl) in Example 1, perfluorooctylethyl atearylate (Kyoeisha Chemical Co., Ltd., product name: Light Acrylate FA— 108) Except that 3.000 g was used, the same components as in Example 1 were mixed in the same amount to prepare a curable resin composition (5).
- thermosetting resin film This curable resin composition ( ⁇ ) was poured between two glass plates in the same manner as in the preparation of the test piece of the heat resistance test method described above, and then left standing in a heating furnace. This was heated at 40 ° C. for 40 minutes and then at 120 ° C. for 10 minutes to obtain a thermosetting resin film. The transparency of this thermosetting resin film was very good.
- the thermogravimetric loss rate in the heat resistance test was 1% or less, indicating excellent heat resistance. No coloring was observed on the test piece after the heat resistance test.
- the variation in the refractive index was 1.50115 ⁇ 0.0003, indicating extremely excellent refractive index precision controllability.
- thermosetting resin film was obtained in the same manner as in Example 2. This thermosetting resin film was cloudy, the thermogravimetric loss rate in the heat resistance test was very large at 10%, and the test piece was colored yellow.
- a curable resin composition (7) was prepared by mixing the same components as in Example 2 except that 500 g was used. .
- thermosetting resin film was obtained in the same manner as in Example 2. This thermosetting resin film was cloudy, the thermogravimetric loss rate in the heat resistance test was as very large as 20%, and the test piece was colored slightly yellow.
- an optical waveguide it is necessary to provide a refractive index difference of about 0.50% between the core and the clad.
- the curable resin composition (I) in Example 1 was used for the core part.
- dimethylol tricyclo [5.2.1.02 2 ' 6 ] decandia tarylate (described above) ) 7.000 g, perfluorootatamethylen-1,8-bis (atalyloyloxymethyl) (supra) 3.300 g and da cure 1173 (supra) 0.26 g were mixed.
- an optical waveguide was formed according to the following method.
- the curable resin composition (III) was applied, and the glass substrate was pressed, followed by photocuring (ultraviolet ray irradiation amount: 3,000 Omj / cm 2 ) to form an upper clad portion.
- the core portion of the formed optical waveguide was cut into a cross section, and the state of the cross section after a heat resistance test at 250 ° C for 5 minutes was observed.As a result, the core portion was distorted and the interface was separated from the clad portion. Was. Also, no optical waveguide could be confirmed.
Abstract
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JP2005506430A JPWO2004104059A1 (ja) | 2003-05-26 | 2004-05-24 | 硬化型樹脂組成物、光学部品および光導波路 |
US10/557,123 US7295749B2 (en) | 2003-05-26 | 2004-05-24 | Curable resin composition, optical component and optical waveguide |
DE602004004655T DE602004004655T8 (de) | 2003-05-26 | 2004-05-24 | Härtende harzzusammensetzung, optisches bauteil und lichtwellenleiter |
EP04734608A EP1630180B1 (en) | 2003-05-26 | 2004-05-24 | Curing resin composition, optical component and optical waveguide |
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JP2003147809 | 2003-05-26 | ||
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US (1) | US7295749B2 (ja) |
EP (1) | EP1630180B1 (ja) |
JP (1) | JPWO2004104059A1 (ja) |
KR (1) | KR20060024375A (ja) |
CN (1) | CN1795215A (ja) |
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WO2007126045A1 (ja) | 2006-04-28 | 2007-11-08 | Omron Corporation | パーフルオロアダマンタン構造を含有する光導波路 |
JP2011102373A (ja) * | 2009-11-12 | 2011-05-26 | Toray Ind Inc | ペーストおよびこれを用いた光導波路 |
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EP2368939A1 (en) * | 2004-10-07 | 2011-09-28 | Hitachi Chemical Co., Ltd. | Resin composition for optical material, and resin film for optical material |
CN101416083A (zh) * | 2006-04-07 | 2009-04-22 | 旭硝子株式会社 | 线栅型偏振器及其制造方法 |
US7811640B2 (en) * | 2006-05-02 | 2010-10-12 | Rpo Pty Limited | Methods for fabricating polymer optical waveguides on large area panels |
JP4929998B2 (ja) * | 2006-11-16 | 2012-05-09 | オムロン株式会社 | 表面処理された樹脂を備える光導波路およびその製造方法 |
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- 2004-05-24 WO PCT/JP2004/007405 patent/WO2004104059A1/ja active IP Right Grant
- 2004-05-24 US US10/557,123 patent/US7295749B2/en not_active Expired - Fee Related
- 2004-05-24 KR KR1020057021302A patent/KR20060024375A/ko not_active Application Discontinuation
- 2004-05-24 EP EP04734608A patent/EP1630180B1/en not_active Expired - Fee Related
- 2004-05-24 JP JP2005506430A patent/JPWO2004104059A1/ja active Pending
- 2004-05-24 CN CNA2004800147068A patent/CN1795215A/zh active Pending
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JP2011102373A (ja) * | 2009-11-12 | 2011-05-26 | Toray Ind Inc | ペーストおよびこれを用いた光導波路 |
Also Published As
Publication number | Publication date |
---|---|
EP1630180B1 (en) | 2007-02-07 |
JPWO2004104059A1 (ja) | 2006-07-20 |
EP1630180A4 (en) | 2006-06-21 |
EP1630180A1 (en) | 2006-03-01 |
US20070025679A1 (en) | 2007-02-01 |
DE602004004655D1 (de) | 2007-03-22 |
US7295749B2 (en) | 2007-11-13 |
DE602004004655T2 (de) | 2007-11-08 |
DE602004004655T8 (de) | 2008-02-14 |
KR20060024375A (ko) | 2006-03-16 |
CN1795215A (zh) | 2006-06-28 |
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