WO2012026298A1 - 体積ホログラム記録用感光性組成物および媒体製造法 - Google Patents
体積ホログラム記録用感光性組成物および媒体製造法 Download PDFInfo
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- WO2012026298A1 WO2012026298A1 PCT/JP2011/067779 JP2011067779W WO2012026298A1 WO 2012026298 A1 WO2012026298 A1 WO 2012026298A1 JP 2011067779 W JP2011067779 W JP 2011067779W WO 2012026298 A1 WO2012026298 A1 WO 2012026298A1
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- polymerizable compound
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- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 description 1
- FHLPGTXWCFQMIU-UHFFFAOYSA-N [4-[2-(4-prop-2-enoyloxyphenyl)propan-2-yl]phenyl] prop-2-enoate Chemical class C=1C=C(OC(=O)C=C)C=CC=1C(C)(C)C1=CC=C(OC(=O)C=C)C=C1 FHLPGTXWCFQMIU-UHFFFAOYSA-N 0.000 description 1
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- XUCHXOAWJMEFLF-UHFFFAOYSA-N bisphenol F diglycidyl ether Chemical compound C1OC1COC(C=C1)=CC=C1CC(C=C1)=CC=C1OCC1CO1 XUCHXOAWJMEFLF-UHFFFAOYSA-N 0.000 description 1
- PCDHSSHKDZYLLI-UHFFFAOYSA-N butan-1-one Chemical compound CCC[C]=O PCDHSSHKDZYLLI-UHFFFAOYSA-N 0.000 description 1
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- 238000007796 conventional method Methods 0.000 description 1
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- PESYEWKSBIWTAK-UHFFFAOYSA-N cyclopenta-1,3-diene;titanium(2+) Chemical class [Ti+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 PESYEWKSBIWTAK-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
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- 238000010894 electron beam technology Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- NHOGGUYTANYCGQ-UHFFFAOYSA-N ethenoxybenzene Chemical compound C=COC1=CC=CC=C1 NHOGGUYTANYCGQ-UHFFFAOYSA-N 0.000 description 1
- MXKYJNXORGALPX-UHFFFAOYSA-N ethenoxyethene;oxetane Chemical compound C1COC1.C=COC=C MXKYJNXORGALPX-UHFFFAOYSA-N 0.000 description 1
- 229940052303 ethers for general anesthesia Drugs 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000005865 ionizing radiation Effects 0.000 description 1
- 229910052743 krypton Inorganic materials 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- DZVCFNFOPIZQKX-LTHRDKTGSA-M merocyanine Chemical compound [Na+].O=C1N(CCCC)C(=O)N(CCCC)C(=O)C1=C\C=C\C=C/1N(CCCS([O-])(=O)=O)C2=CC=CC=C2O\1 DZVCFNFOPIZQKX-LTHRDKTGSA-M 0.000 description 1
- NFLOWLFQCMNSRE-UHFFFAOYSA-N methyl 2-tert-butylperoxycarbonyl-4-(3-tert-butylperoxycarbonyl-4-methoxycarbonylbenzoyl)benzoate Chemical compound C1=C(C(=O)OOC(C)(C)C)C(C(=O)OC)=CC=C1C(=O)C1=CC=C(C(=O)OC)C(C(=O)OOC(C)(C)C)=C1 NFLOWLFQCMNSRE-UHFFFAOYSA-N 0.000 description 1
- ZGYTYDNWEZVHEL-UHFFFAOYSA-N methyl 2-tert-butylperoxycarbonyl-4-(4-tert-butylperoxycarbonyl-3-methoxycarbonylbenzoyl)benzoate Chemical compound C1=C(C(=O)OOC(C)(C)C)C(C(=O)OC)=CC=C1C(=O)C1=CC=C(C(=O)OOC(C)(C)C)C(C(=O)OC)=C1 ZGYTYDNWEZVHEL-UHFFFAOYSA-N 0.000 description 1
- ZNEQIOWZBXJFCG-UHFFFAOYSA-N methyl 2-tert-butylperoxycarbonyl-5-(4-tert-butylperoxycarbonyl-3-methoxycarbonylbenzoyl)benzoate Chemical compound C1=C(C(=O)OOC(C)(C)C)C(C(=O)OC)=CC(C(=O)C=2C=C(C(C(=O)OOC(C)(C)C)=CC=2)C(=O)OC)=C1 ZNEQIOWZBXJFCG-UHFFFAOYSA-N 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
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- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 1
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- 239000005022 packaging material Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
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- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
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- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920006267 polyester film Polymers 0.000 description 1
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- 229920001223 polyethylene glycol Polymers 0.000 description 1
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- 239000003505 polymerization initiator Substances 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- WVIICGIFSIBFOG-UHFFFAOYSA-N pyrylium Chemical class C1=CC=[O+]C=C1 WVIICGIFSIBFOG-UHFFFAOYSA-N 0.000 description 1
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- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
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- OKYDCMQQLGECPI-UHFFFAOYSA-N thiopyrylium Chemical class C1=CC=[S+]C=C1 OKYDCMQQLGECPI-UHFFFAOYSA-N 0.000 description 1
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- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
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- 239000001018 xanthene dye Substances 0.000 description 1
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Images
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03H—HOLOGRAPHIC PROCESSES OR APPARATUS
- G03H1/00—Holographic processes or apparatus using light, infrared or ultraviolet waves for obtaining holograms or for obtaining an image from them; Details peculiar thereto
- G03H1/02—Details of features involved during the holographic process; Replication of holograms without interference recording
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/24—Di-epoxy compounds carbocyclic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
- C08G59/687—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used containing sulfur
-
- G—PHYSICS
- G11—INFORMATION STORAGE
- G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
- G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
- G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
- G11B7/2403—Layers; Shape, structure or physical properties thereof
- G11B7/24035—Recording layers
- G11B7/24044—Recording layers for storing optical interference patterns, e.g. holograms; for storing data in three dimensions, e.g. volume storage
-
- G—PHYSICS
- G11—INFORMATION STORAGE
- G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
- G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
- G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
- G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
- G11B7/242—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers
- G11B7/244—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only
- G11B7/245—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing a polymeric component
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03H—HOLOGRAPHIC PROCESSES OR APPARATUS
- G03H1/00—Holographic processes or apparatus using light, infrared or ultraviolet waves for obtaining holograms or for obtaining an image from them; Details peculiar thereto
- G03H1/02—Details of features involved during the holographic process; Replication of holograms without interference recording
- G03H2001/026—Recording materials or recording processes
- G03H2001/0264—Organic recording material
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03H—HOLOGRAPHIC PROCESSES OR APPARATUS
- G03H2260/00—Recording materials or recording processes
- G03H2260/12—Photopolymer
Definitions
- the present invention relates to a photosensitive composition for volume hologram recording, a volume hologram recording medium obtained from the composition, a method for producing the recording medium, and a hologram recording method using the recording medium.
- Holographic memory that records information as holograms is attracting attention as a next-generation information recording medium capable of high-capacity and high-speed transfer.
- a hologram recording medium for example, a medium mainly composed of a radical polymerizable monomer, a thermoplastic binder resin, a photo radical polymerizable compound, and a sensitizing dye is widely known.
- Information is recorded by forming a photosensitive composition for hologram recording into a film and performing interference light exposure.
- a radically polymerizable monomer is polymerized in a portion that is strongly irradiated with light, and the radically polymerizable monomer diffuses from a portion that is weakly irradiated to a portion that is strongly irradiated with light, thereby generating a concentration gradient. Thereby, a refractive index difference corresponding to the intensity of light is generated, and a hologram is formed.
- a medium in which a polymerizable monomer is dispersed in a three-dimensional crosslinked epoxy matrix has been proposed.
- Such a medium is required to have a certain degree of hardness, but if the matrix is hardened, sufficient free space in the matrix where the photopolymerizable monomer can be diffused cannot be obtained, and a sufficient refractive index difference is obtained. Can't get. Further, when the matrix is softened and the free space in the matrix is increased, the recording layer locally contracts with the polymerization of the polymerizable monomer, and it is difficult to accurately reproduce the recorded data.
- the object of the present invention is to use two or more radically polymerizable compounds and a three-dimensional cross-linked polymer matrix as reactive compounds used for hologram recording, so that the diffraction efficiency is high, the curing shrinkage is small, and the storage stability is excellent. Another object is to provide a hologram recording medium. Another object of the present invention is to obtain a volume hologram recording medium having excellent moisture resistance and thermal stability and further suppressed curing shrinkage, using the above composition. Another object of the present invention is to obtain a method for producing the recording medium and a recording method using the recording medium.
- the present invention relates to a three-dimensional crosslinked polymer matrix precursor material (I) containing a cationically polymerizable compound (C) and a thermal acid generator (F), two or more kinds of radically polymerizable compounds (X),
- the photosensitive composition for volume hologram recording characterized by containing a radical photopolymerization initiator (E) and a sensitizing dye (G).
- the three-dimensional crosslinked polymer matrix precursor material (I) includes an alicyclic epoxy compound (Ia) having an epoxy group composed of two adjacent carbon atoms and oxygen atoms constituting the alicyclic ring, and the alicyclic epoxy.
- One or more cationically polymerizable compounds selected from the group consisting of epoxy compounds (Ib-1), oxetane compounds (Ib-2), and vinyl ether compounds (Ib-3) other than compound (Ia) It is preferable to contain.
- the radical polymerizable compound (X) includes a radical polymerizable compound (B) having an ethylenically unsaturated bond capable of radical polymerization and having at least one hydroxyl group or carboxyl group, and ethylene capable of radical polymerization. It is preferable to contain the radically polymerizable compound (A) which has an ionic unsaturated bond and does not have a hydroxyl group and a carboxyl group.
- the molar ratio of the total amount of hydroxyl groups and carboxyl groups to the total amount of unsaturated bonds is in the range of 0.01 to 0.5. It is preferable to combine the radical polymerizable compound (A) and the radical polymerizable compound (B) so as to be inside.
- the present invention also relates to a volume hologram containing a radical polymerizable compound, a three-dimensional cross-linked polymer matrix, a photo radical polymerization initiator, and a sensitizing dye obtained by heat-treating the photosensitive composition for volume hologram recording.
- a photosensitive composition for recording is provided.
- the present invention also provides a volume hologram recording medium obtained by sandwiching the photosensitive composition for volume hologram recording with a substrate and aging it for a predetermined time.
- the present invention also provides a volume hologram recording medium having a substrate and a volume hologram recording layer made of the photosensitive composition for volume hologram recording sandwiched between the substrates.
- the present invention also provides a method for producing a volume hologram recording medium, characterized in that the photosensitive composition for volume hologram recording is sandwiched between substrates and heat-treated and / or aged for a certain period of time.
- the present invention also provides a hologram recording method characterized in that the radically polymerizable compound is polymerized by irradiating the volume hologram recording medium with a laser beam.
- the present invention provides a volume hologram recording medium characterized in that the transmittance after recording a hologram by the above method is 80% or more.
- the hologram recording medium of the present invention has a recording layer containing a three-dimensional cross-linked polymer matrix, a radical polymerizable compound, a photo radical polymerization initiator, and a sensitizing dye, by combining two or more kinds of radical polymerizable compounds. Curing shrinkage, which is a problem of radical polymerization hologram recording media, can be remarkably suppressed. According to the present invention, there are provided a hologram recording medium having a high recording capacity, a high refractive index modulation and a small volume change by light irradiation, and a hologram recording method using the same.
- the photosensitive composition for volume hologram recording of the present invention comprises a three-dimensional crosslinked polymer matrix precursor material (I) containing a cationic polymerizable compound (C) and a thermal acid generator (F), and two or more radicals. It contains a polymerizable compound (X), a radical photopolymerization initiator (E), and a sensitizing dye (G).
- the three-dimensional crosslinked polymer matrix precursor material (I) contained in the volume hologram recording photosensitive composition of the present invention contains a cationically polymerizable compound (C) and a thermal acid generator (F).
- cationic polymerizable compound (C) examples include an alicyclic epoxy compound (Ia) having an epoxy group composed of two adjacent carbon atoms and oxygen atoms constituting the alicyclic ring, and the alicyclic epoxy compound (Ia). And cationically polymerizable compounds such as epoxy compound (Ib-1), oxetane compound (Ib-2) and vinyl ether compound (Ib-3).
- the alicyclic epoxy compound (Ia) is not particularly limited as long as it is a compound having an epoxy group, and may be either a monofunctional epoxy compound or a polyfunctional epoxy compound, but a polyfunctional epoxy compound is preferred. .
- the compound which has an epoxy group can be used individually or in combination of 2 or more types.
- alicyclic epoxy compound (Ia) include 3,4,3 ′, 4′-diepoxybicyclohexyl, 2,2-bis (3,4-epoxycyclohexyl) propane, 2,2- Bis (3,4-epoxycyclohexyl) -1,3-hexafluoropropane, bis (3,4-epoxycyclohexyl) methane, 1- [1,1-bis (3,4-epoxycyclohexyl)] ethylbenzene, bis ( 3,4-epoxycyclohexyl) adipate, 3,4-epoxycyclohexylmethyl (3,4-epoxy) cyclohexanecarboxylate, (3,4-epoxy-6-methylcyclohexyl) methyl-3 ′, 4′-epoxy-6 -Methylcyclohexanecarboxylate, ethylene-1,2-bis (3,4-epoxycyclohexane Bon
- Examples of commercially available alicyclic epoxy resins include Celoxide 2000, Celoxide 2021, Celoxide 3000, EHPE 3150 manufactured by Daicel Chemical Industries, Ltd .; Epomic VG-3101 manufactured by Mitsui Chemicals; Examples thereof include TETRAD-X and TETRAD-C manufactured by Mitsubishi Gas Chemical Company; EPB-13 and EPB-27 manufactured by Nippon Soda Co., Ltd.
- Examples of the epoxy compound (Ib-1) other than the alicyclic epoxy compound (Ia) include biphenol diglycidyl ether, bisphenol A diglycidyl ether, bisphenol F diglycidyl ether, bisphenol S diglycidyl ether, and tetramethylbiphenol diglycidyl.
- Examples thereof include epoxy resins having a glycidyl group such as ether, naphthalenediol diglycidyl ether, bisphenol fluorenediglycidyl ether, biscresol fluorenediglycidyl ether, and bisphenoxyethanol fluorenediglycidyl ether. These compounds can be used alone or in combination of two or more.
- the oxetane compound (Ib-2) is not particularly limited as long as it is a compound having an oxetanyl group, and may be either a monofunctional oxetane compound or a polyfunctional oxetane compound, but a polyfunctional oxetane compound is preferable.
- the compounds having an oxetanyl group can be used alone or in combination of two or more.
- Representative examples of the compound having an oxetanyl group include 3-ethyl-3- (phenoxymethyl) oxetane (POX), di [1-ethyl (3-oxetanyl)] methyl ether (DOX), 3 manufactured by Toagosei Co., Ltd.
- POX 3-ethyl-3- (phenoxymethyl) oxetane
- DOX di [1-ethyl (3-oxetanyl)] methyl ether
- EHOX 3-ethyl-3- ⁇ [3- (triethoxysilyl) propoxy] methyl ⁇ oxetane
- TEOX 3-ethyl-3- ⁇ [3- (triethoxysilyl) propoxy] methyl ⁇ oxetane
- OX- SQ oxetanylsilsesquioxane
- PNOX-1009 phenol novolac oxetane
- a compound having a different cationically polymerizable group in the molecule such as 3,3-dimethanol divinyl ether oxetane having an oxetanyl group and a vinyl ether group can also be used.
- the vinyl ether compound (Ib-3) is not particularly limited as long as it is a compound having a vinyl ether group, and may be either a monofunctional vinyl ether compound or a polyfunctional vinyl ether compound, but a polyfunctional vinyl ether compound is preferred.
- the compounds having a vinyl ether group can be used alone or in combination of two or more.
- the compound having a vinyl ether group include cyclic ether type vinyl ethers such as isosorbite divinyl ether and oxanorbornene divinyl ether (vinyl ethers having a cyclic ether group such as oxirane ring, oxetane ring and oxolane ring); phenyl vinyl ether and the like Aryl vinyl ethers; alkyl vinyl ethers such as n-butyl vinyl ether and octyl vinyl ether; cycloalkyl vinyl ethers such as cyclohexyl vinyl ether; polyfunctional vinyl ethers such as hydroquinone divinyl ether, 1,4-butanediol divinyl ether, cyclohexane divinyl ether and cyclohexane dimethanol divinyl ether Etc.
- cyclic ether type vinyl ethers such as isosorbite divinyl ether and oxanorbornen
- HEVE 2-hydroxyethyl vinyl ether
- DEGV diethylene glycol monovinyl ether
- HBVE 2-hydroxybutyl vinyl ether
- triethylene glycol divinyl ether etc. manufactured by Maruzen Petrochemical Co., Ltd.
- the vinyl ether compound which has substituents, such as an alkyl group and an allyl group, in alpha and / or beta position can also be used.
- Examples of the cationic polymerizable compound (C) include an alicyclic epoxy compound (Ia) having an epoxy group composed of two adjacent carbon atoms and oxygen atoms constituting the alicyclic ring, and the alicyclic epoxy compound (Ia).
- an alicyclic epoxy compound (Ia) having an epoxy group composed of two adjacent carbon atoms and oxygen atoms constituting the alicyclic ring
- the alicyclic epoxy compound (Ia) Other than the epoxy compound (Ib-1), the oxetane compound (Ib-2), and the vinyl ether compound (Ib-3). It is preferable.
- the thermal acid generator (F) contained in the photosensitive composition for volume hologram recording of the present invention is not particularly limited as long as it is a compound that activates thermal cationic polymerization.
- Sun Aid SI-60L, Sun Aid SI- Aromatic sulfonium salts such as 80L, Sun-Aid SI-100L, Sun-Aid SI-110L, Sun-Aid SI-150L (manufactured by Sanshin Chemical Co., Ltd.) can be used.
- the thermal acid generator is used in a proportion of, for example, 0.1 to 30 parts by weight, preferably 0.5 to 10 parts by weight, based on 100 parts by weight of the cationically polymerizable compound (total amount).
- the radically polymerizable compound (X) contained in the photosensitive composition for volume hologram recording of the present invention has a radically polymerizable unsaturated double bond having a radically polymerizable group such as acrylate, methacrylate or vinyl compound. A combination of two or more compounds.
- the radical polymerizable compound (X) may be monofunctional or polyfunctional. Examples of the radical polymerizable compound include unsaturated carboxylic acids, salts of unsaturated carboxylic acids, ester compounds of unsaturated carboxylic acids and aliphatic polyhydric alcohols, and amides of unsaturated carboxylic acids and aliphatic polyvalent amine compounds. A compound or the like is preferably used.
- the radical polymerizable compound (X) includes a radical polymerizable compound (B) having an ethylenically unsaturated bond capable of radical polymerization and having at least one hydroxyl group or carboxyl group, and an ethylenically unsaturated compound capable of radical polymerization. It can be set as the compound containing the radically polymerizable compound (A) which has a saturated bond and does not have a hydroxyl group and a carboxyl group.
- radically polymerizable compound having no hydroxyl group and carboxyl group (A) those not containing a fluorine atom are preferably used.
- styrene, 2-chlorostyrene, 2-bromostyrene, Styrenes such as methoxystyrene
- vinylnaphthalenes such as 1-vinylnaphthalene and 2-vinylnaphthalene
- vinylbenzenes such as vinylbenzene and divinylbenzene
- 2-phenoxyethyl (meth) acrylate ethylene glycol di (meth) acrylate, 1,3-butanediol di (meth) acrylate, tetramethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, trimethylolpropane tri (meth) acrylate , Trimethylolethane tri (meth) acrylate, tetraethylene glycol di (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipent
- radical polymerizable compound (B) having at least one hydroxyl group or carboxyl group those not containing a fluorine atom are preferably used.
- bisphenol A epoxy (meth) acrylate bisphenol A ethylene glycol Mono (meth) acrylate, triethylene glycol mono (meth) acrylate, 1,3-butanediol mono (meth) acrylate, 1,2-propanediol-1- (meth) acrylate, tetramethylene glycol mono (meth) acrylate, Propyleneglycol mono (meth) acrylate, neopentyl glycol mono (meth) acrylate, triethylene glycol di (meth) acrylate, pentaerythritol di (meth) acrylate, pentaerythritol tri (me ) Hydroxyls such as acrylate, dipentaerythritol di (meth) acrylate, dipentaerythritol tri (meth) acrylate, dipentaerythritol tetra (meth) acrylate, 2,2,2-tris (meth) acryl
- the hologram recording medium of the present invention has a recording layer containing a three-dimensional cross-linked polymer matrix, a radical polymerizable compound, a photo radical polymerization initiator, and a sensitizing dye, preferably a radical polymerization having a hydroxyl group or a carboxyl group.
- the curing shrinkage that is a problem of the radical polymerization type hologram recording medium can be remarkably suppressed by combining the functional compound and the radical polymerizable compound having no hydroxyl group and carboxyl group at a certain ratio.
- the radical polymerizable compound (X) has an ethylenically unsaturated bond capable of radical polymerization, and the molar ratio of the total amount of hydroxyl group and carboxyl group to the unsaturated bond (OH group and COOH group / unsaturated). It is preferable to combine the radical polymerizable compound (A) and the radical polymerizable compound (B) so that the saturated bond) is in the range of 0.01 to 0.5.
- the radically polymerizable compound in the photosensitive composition for volume hologram recording can be used at a ratio of, for example, 10 to 500 parts by weight, preferably 50 to 300 parts by weight with respect to 100 parts by weight of the cationically polymerizable compound (C).
- the radical photopolymerization initiator (E) is not particularly limited as long as it is a compound that activates radical radical polymerization.
- benzoin benzoin alkyl ethers such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether; acetophenone, 2,2-dimethoxy-2-phenylacetophenone, 2,2-diethoxy-2-phenylacetophenone 1,1-dichloroacetophenone, 2-methyl-1- [4- (methylthio) phenyl] -2-morpholino-propan-1-one, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) ) -Acetophenones such as butan-1-one; anthraquinones such as 2-methylanthraquinone, 2-ethylanthraquinone, 2-tertiarybutylanthraquinone, 1-chloroanthraquinone, 2-amylanthraquinone; 2,4-di Thioxanthones such as methyl
- the radical photopolymerization initiator is used in a proportion of, for example, 0.1 to 30 parts by weight, preferably 1 to 20 parts by weight, based on 100 parts by weight of the total amount of the radical polymerizable compound (E). Is used in a proportion of, for example, 0.1 to 30 parts by weight, preferably 1 to 20 parts by weight, based on 100 parts by weight of the radical photopolymerizable compound (total amount).
- the sensitizing dye (G) is not particularly limited as long as it sensitizes the photopolymerization initiator, and known ones can be used.
- Examples of sensitizing dyes include thiopyrylium salt dyes, merocyanine dyes, quinoline dyes, styrylquinoline dyes, ketocoumarin dyes, thioxanthene dyes, xanthene dyes, oxonol dyes, cyanine dyes, rhodamine dyes, Examples include pyrylium salt dyes.
- the visible light sensitizing dye is preferably colorless and transparent when decomposed by a post-process after hologram recording, heating or ultraviolet irradiation when high transparency such as an optical element is required.
- a sensitizing dye can be used individually or in combination of 2 or more types. Of these, cyanine dyes are preferably used. Specifically, 3-ethyl-2- [3- (3-ethyl-5-phenyl-2-benzoxazolinylidene represented by the following formula (1) is used.
- the photosensitive composition for volume hologram recording of the present invention may contain a plasticizer, if necessary.
- a plasticizer diethyl sebacate or the like can be used.
- the volume hologram recording medium of the present invention includes a substrate and a volume hologram recording layer made of the photosensitive composition for volume hologram recording sandwiched between the substrates.
- the volume hologram recording medium is obtained by sandwiching the photosensitive composition for volume hologram recording with a substrate and heat-treating and / or aging for a certain period of time.
- the volume hologram recording medium of the present invention is a hologram recording medium in which curing shrinkage is remarkably suppressed, a high recording capacity, a high refractive index modulation, and a small volume change due to light irradiation.
- the thickness of the volume hologram recording layer is, for example, 1 to 2000 ⁇ m, preferably 10 to 1000 ⁇ m. In general, if the thickness is too thin, a hologram with low angle selectivity is likely to be formed. Conversely, if the thickness is thick, a hologram with high angle selectivity can be obtained.
- the base material (substrate) may be any material that is transparent to visible light.
- a glass plate for example, a cycloolefin polymer film (for example, “TOPAS” manufactured by Daicel Chemical Industries, Ltd.), a polyethylene film , Polypropylene film, Polyfluoroethylene film, Polyvinylidene fluoride film, Polyvinyl chloride film, Polyvinylidene chloride film, Polymethylmethacrylate film, Polycarbonate (PC) film, Polyethersulfone film, Polyetherketone film, Polyamide film, Tetra Fluoroethylene-perfluoroalkyl vinyl ether copolymer film, polyester film such as polyethylene terephthalate (PET) film, plastic film such as polyimide film Is like including g), these substrates can be used in the same, or a different combination.
- PET polyethylene terephthalate
- plastic film such as polyimide film Is like including g
- the volume hologram recording medium of the present invention can be, for example, a transmission type volume hologram recording medium.
- the sensitizing dye is preferably decomposed after hologram recording, and the transmittance is 80% or more.
- the volume hologram recording medium of the present invention is produced by sandwiching the photosensitive composition for volume hologram recording between the substrates, heat treatment and / or aging for a certain time.
- the time for the heat treatment and aging can be a time for completing the curing reaction of the components of the three-dimensional polymer matrix precursor material in the system.
- the heat treatment is preferably performed at 40 ° C. or higher and 300 ° C. or lower, and more preferably performed at 40 ° C. or higher and 150 ° C. or lower.
- the heating time is, for example, 10 minutes to 5 hours, preferably 10 minutes to 3 hours. When the heating time is shorter than 10 minutes, the curing reaction does not end even if a subsequent aging step is performed, which may be undesirable. If the heating time exceeds 5 hours, the reaction of the radical polymerizable compound may proceed, and sufficient hologram characteristics may not be obtained.
- the aging is carried out, for example, by subjecting the cationically polymerizable compound to a dark reaction at -15 ° C. or higher and lower than 40 ° C., preferably 0 ° C. or higher and 35 ° C. or lower (room temperature) under light-shielding conditions.
- a dark reaction at -15 ° C. or higher and lower than 40 ° C., preferably 0 ° C. or higher and 35 ° C. or lower (room temperature) under light-shielding conditions.
- the reaction in the medium can be calmed down.
- the curing reaction of the volume hologram recording layer can be terminated by aging.
- the completion of the curing reaction can be confirmed by, for example, evaluating the formed film by using an infrared spectrum measuring device (IR), DSC, or the like to confirm the cured state of the matrix.
- the aging step also includes a step of sufficiently returning the volume hologram recording medium after the heat treatment to room temperature. After heating, the volume
- the aging time is determined by the time required for completion of the above curing reaction, and is about 5 minutes to 1 week, preferably about 10 minutes to 4 days, and more preferably about 30 minutes to 48 hours. Since the time for completely curing the epoxy group varies depending on the composition of the photosensitive composition, the heat treatment and the aging time are selected appropriately for each photosensitive composition.
- the radically polymerizable compound is polymerized by irradiating a volume hologram recording medium with laser light.
- the sensitizing dye is preferably decomposed, and the transmittance after recording can be 80% or more.
- a method of irradiating the volume hologram recording medium with laser light a known method can be used.
- the original is adhered to the volume hologram recording material layer of the volume hologram recording medium, and the volume is obtained by performing interference exposure using ionizing radiation such as visible light, ultraviolet light, or electron beam from the transparent substrate film side.
- visible laser light such as argon ion laser (458 nm, 488 nm, 514.5 nm), krypton ion laser (647.1 nm), helium-neon ion laser (633 nm), YAG laser ( 532 nm) or the like can be used.
- the hologram recording mechanism using the photosensitive composition for volume hologram recording will be described as follows. That is, when the photosensitive composition (volume hologram recording layer) formed in a film shape is subjected to interference exposure with a laser, polymerization of the photocurable compound is started in a portion where light is strong, and accordingly, the photopolymerizable compound A concentration gradient is formed, and the photopolymerizable compound diffuses and moves from a weak light portion to a strong light portion. As a result, the photopolymerizable compound can be made dense and dense depending on the strength of the interference fringes, and appears as a difference in refractive index. A hologram is recorded by the refractive index difference.
- a matrix polymer can be used in order to suppress the fluidity of the monomer in the photosensitive composition for volume hologram recording.
- the matrix polymer can be prepared by placing compounds having different reactivity in the photosensitive composition and three-dimensionally crosslinking in the step of preparing a recording medium.
- a matrix polymer in a cationic curing system, can be produced in a recording medium using radical polymerization.
- a matrix polymer in a radical curing system, a matrix polymer can be produced in a recording medium using cationic polymerization.
- a hologram is recorded by the difference in refractive index between the photopolymerizable compound and the matrix polymer.
- Refractive index modulation can be promoted by heating after interference exposure with a laser, but especially when a matrix polymer is contained, the monomer movement is further promoted by making the heating temperature close to the glass transition temperature of the matrix polymer. Thus, the amount of refractive index modulation can be increased.
- the volume hologram recording medium of the present invention has a diffraction efficiency of 10% or more, preferably 50% or more by forming a three-dimensional crosslinked polymer matrix and containing two or more radically polymerizable compounds (X) in the recording monomer.
- X radically polymerizable compounds
- it can be 80% or more.
- the curing shrinkage is a cure shrinkage when the radically polymerizable compound (A) having no hydroxyl group and carboxyl group is used alone by containing two or more kinds of radically polymerizable compounds (X) in the recording monomer. From the rate, the curing shrinkage can be gradually decreased at a rate of 10% or more, preferably 50% or more, particularly 80% or more. In particular, it is preferable to combine the radically polymerizable compound (B) having a hydroxyl group or a carboxyl group and the radically polymerizable compound (A) having no hydroxyl and carboxyl groups at a certain ratio.
- FIG. 1 shows a schematic diagram of the optical system used in the experiment.
- the light source was a 532 nm semiconductor laser, which was divided into two lights by a beam splitter (BS) through a mirror (M), a spatial filter (OL and Ph), a plano-convex lens (PCL), and a wave plate (PP).
- the two lights separated by the BS were incident and interfered with the sample at 30 ° and 30 ° through the mirror, respectively.
- the intensity of diffracted light and transmitted light was detected by a power meter (PM: manufactured by ADC Corporation).
- the diffraction efficiency and the ratio of the second-order diffracted light to the first-order diffracted light were determined by the following method.
- the diffraction efficiency of a hologram recorded by the two-beam interference method was measured using a power meter.
- a 532 nm semiconductor laser having a diameter of 5 ⁇ was incident at an angle of 30 °, and transmitted light and diffracted light were detected.
- the volume hologram recording medium was axially rotated in the range of ⁇ 5 ° to 5 °, and the diffraction efficiency ⁇ was calculated using the following (formula 1) at the position where the diffracted light intensity was highest.
- ⁇ L 1 / (L 0 + L 1 )
- Formula 1) Transmitted light intensity: L 0 , diffracted light intensity: L 1 )
- the volume hologram recording medium was installed at an angle of 10 °, and hologram recording was performed with the angles of the recording light and the reference light being 20 ° and 40 °, respectively. Thereafter, the reference light was incident at an angle of 40 °, and the angle indicating the maximum diffraction efficiency was detected ( ⁇ 1 ). When there is no contraction, the angle indicated by the maximum diffraction efficiency obtained at that time is 40 °, but the contraction causes a deviation from 40 °. Similarly, only the recording light was incident at an angle of 20 °, and the angle ( ⁇ 2 ) indicating the maximum diffraction efficiency was detected.
- the grating vector (K 1 and K 2 ) in the thickness direction of the recording medium was obtained from the following (Equation 2) and (Equation 3), and the shrinkage was calculated from (Equation 4).
- K 1 (2 ⁇ / ⁇ ) ⁇ (n 2 ⁇ sin 2 ⁇ 1 ) 1/2 ) ⁇ (n 2 ⁇ sin 2 ⁇ 2 ) 1/2 ) ⁇ ...
- Example 1 10 parts by weight of 1,2-propanediol-1-acrylate, a monofunctional acrylate compound having an OH group as a radical polymerizable compound, 40 parts by weight of pentaerythritol tetraacrylate, a tetrafunctional acrylate compound, cationic polymerizable 25 parts by weight of a bifunctional alicyclic epoxy compound (3,4,3 ′, 4′-diepoxybicyclohexyl) as a compound, 25 parts by weight of diethyl sebacate as a plasticizer, 3, as a radical photopolymerization initiator 10 parts by weight of 3 ′, 4,4′-tetra (t-butylperoxycarbonyl) benzophenone with respect to 50 parts by weight of the radical polymerizable compound, triphenylsulfonium salt (trade name “Sun-Aid SI-60L” as a thermal acid generator) "Sanshin Chemical Co., Ltd.) 1 part by weight per
- the photosensitive liquid 1 is sandwiched between two 3 ⁇ 3 cm 1 mm-thick glass substrates together with a spacer film (PET) having a thickness of 100 ⁇ m, the periphery is sealed, and then heated in an oven at 90 ° C. for 1 hour to produce a hologram recording medium 1 was obtained.
- PET spacer film
- the maximum diffraction efficiency was 52% and the cure shrinkage rate was 0.29%.
- ⁇ Comparative Example 1 50 parts by weight of pentaerythritol tetraacrylate which is a tetrafunctional acrylate compound as a radical polymerizable compound, and a bifunctional alicyclic epoxy compound (3,4,3 ′, 4′-diepoxybicyclohexyl) as a cationic polymerizable compound 25 parts by weight of diethyl sebacate as a plasticizer, and 50 parts by weight of radically polymerizable compound of 3,3 ′, 4,4′-tetra (t-butylperoxycarbonyl) benzophenone as a radical photopolymerization initiator Sensitizing dye, 10 parts by weight of triphenylsulfonium salt (trade name “Sun-Aid SI-60L”, Sanshin Chemical Co., Ltd.) as thermal acid generator, 1 part by weight of 25 parts by weight of cationically polymerizable compound As the photosensitive solution C1, 0.1 part by weight of cyanine dye 1 was stirred
- ⁇ Comparative Example 6 50 parts by weight of 1,2-propanediol-1-acrylate, which is a monofunctional acrylate compound having an OH group as a radical polymerizable compound, and a bifunctional alicyclic epoxy compound (3,4,3) as a cationic polymerizable compound 25 parts by weight of ', 4'-diepoxybicyclohexyl), 25 parts by weight of diethyl sebacate as a plasticizer, and 3,3', 4,4'-tetra (t-butylperoxycarbonyl) as a radical photopolymerization initiator ) 10 parts by weight of benzophenone with respect to 50 parts by weight of radically polymerizable compound, and 25 parts by weight of cationically polymerizable compound of triphenylsulfonium salt (trade name “Sun-Aid SI-60L” manufactured by Sanshin Chemical Co., Ltd.)
- the photosensitive solution C6 was prepared by stirring and dissolving 1 part by weight of the dye
- Example 22 40 parts by weight of 1,2-propanediol-1-acrylate, a monofunctional acrylate compound having an OH group as a radical polymerizable compound, 10 parts by weight of pentaerythritol tetraacrylate, a tetrafunctional acrylate compound, cationic polymerizable 25 parts by weight of a bifunctional alicyclic epoxy compound (3,4,3 ′, 4′-diepoxybicyclohexyl) as a compound, 25 parts by weight of diethyl sebacate as a plasticizer, 3, as a radical photopolymerization initiator 10 parts by weight of 3 ′, 4,4′-tetra (t-butylperoxycarbonyl) benzophenone with respect to 50 parts by weight of the radical polymerizable compound, triphenylsulfonium salt (trade name “Sun-Aid SI-60L” as a thermal acid generator) "Sanshin Chemical Co., Ltd.) 1 part by weight per
- A1 Pentaerythritol tetraacrylate
- A2 o-phenylphenol acrylate
- A3 9,9-bis [4- (2-acryloyloxyethoxy) phenyl] fluorene
- A4 ethoxylated bisphenol A diacrylate
- A5 styrene
- B1 1,2-propanediol-1-acrylate
- B2 pentaerythritol triacrylate
- B3 bisphenol A epoxy acrylate
- B4 2,2,2-trisacryloyloxymethyl ethyl succinic acid
- C1 3,4,3 ′, 4′-diepoxybicyclohexyl
- C2 2,2-bis (3,4-epoxycyclohexyl) propane
- C3 2,2-bis (3,4-epoxycyclohexyl) -1, 3-hexafluoropropane
- C4 bis (3,4-epoxycyclohexyl)
- the photosensitive composition for volume hologram recording of the present invention it is possible to obtain a hologram recording medium having a high recording capacity, a high refractive index modulation, and a small volume change by light irradiation.
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Abstract
Description
また、本発明の他の目的は、上記組成物を用いて、優れた耐湿性、熱安定性を有し、さらに、硬化収縮が抑制された体積ホログラム記録媒体を得ることにある。
さらに、本発明の他の目的は、上記記録媒体の製造法ならびに上記記録媒体を用いた記録方法を得ることにある。
本発明の体積ホログラム記録用感光性組成物は、カチオン重合性化合物(C)と熱酸発生剤(F)とを含有する三次元架橋ポリマーマトリックス前駆体材料(I)と、2種以上のラジカル重合性化合物(X)と、光ラジカル重合開始剤(E)と、増感色素(G)とを含有することを特徴とする。
本発明の体積ホログラム記録用感光性組成物に含まれる三次元架橋ポリマーマトリックス前駆体材料(I)は、カチオン重合性化合物(C)と熱酸発生剤(F)とを含有する。
カチオン重合性化合物(C)としては、脂環を構成する隣接する2つの炭素原子と酸素原子とで構成されるエポキシ基を有する脂環エポキシ化合物(Ia)、前記脂環エポキシ化合物(Ia)以外のエポキシ化合物(Ib-1)、オキセタン化合物(Ib-2)、ビニルエーテル化合物(Ib-3)などのカチオン重合性化合物が挙げられる。
本発明の体積ホログラム記録用感光性組成物に含まれる熱酸発生剤(F)としては、熱カチオン重合を活性化する化合物であれば特に限定されず、例えば、サンエイドSI-60L、サンエイドSI-80L、サンエイドSI-100L、サンエイドSI-110L、サンエイドSI-150L(三新化学社製)などの芳香族スルホニウム塩を用いることができる。熱酸発生剤は、カチオン重合性化合物(総量)100重量部に対して、例えば0.1~30重量部、好ましくは0.5~10重量部の割合で使用される。
本発明の体積ホログラム記録用感光性組成物に含まれるラジカル重合性化合物(X)は、例えば、アクリレート、メタクリレート、ビニル化合物等のラジカル重合性基を有するラジカル重合可能な不飽和二重結合を持つ化合物を2種以上組み合わせたものである。ラジカル重合性化合物(X)は、単官能であっても多官能であってもよい。ラジカル重合性化合物としては、例えば、不飽和カルボン酸、不飽和カルボン酸の塩、不飽和カルボン酸と脂肪族多価アルコールとのエステル化合物、不飽和カルボン酸と脂肪族多価アミン化合物とのアミド化合物などが好ましく用いられる。ラジカル重合性化合物(X)としては、ラジカル重合可能なエチレン性不飽和結合を有し、且つヒドロキシル基またはカルボキシル基を1つ以上有するラジカル重合性化合物(B)と、ラジカル重合可能なエチレン性不飽和結合を有し、且つヒドロキシル基及びカルボキシル基を有していないラジカル重合性化合物(A)とを含有する化合物とすることができる。
ヒドロキシル基またはカルボキシル基を有していないラジカル重合性化合物(A)としては、好ましくは、フッ素原子を含有しないものが使用され、具体的には、スチレン、2-クロロスチレン、2-ブロモスチレン、メトキシスチレンなどのスチレン類;1-ビニルナフタレン、2-ビニルナフタレンなどのビニルナフタレン類;ビニルベンゼン、ジビニルベンゼンなどのビニルベンゼン類;2-フェノキシエチル(メタ)アクリレート、エチレングリコールジ(メタ)アクリレート、1,3-ブタンジオールジ(メタ)アクリレート、テトラメチレングリコールジ(メタ)アクリレート、プロピレングリコールジ(メタ)アクリレート、ネオペンチルグリコールジ(メタ)アクリレート、トリメチロールプロパントリ(メタ)アクリレート、トリメチロールエタントリ(メタ)アクリレート、テトラエチレングリコールジ(メタ)アクリレート、ペンタエリスリトールテトラ(メタ)アクリレート、ジペンタエリスリトールヘキサ(メタ)アクリレート、o-フェニルフェノール(メタ)アクリレート、エポキシ化ビスフェノールAジ(メタ)アクリレート、ビスフェノールAエチレングリコールジ(メタ)アクリレート、9,9-ビス[4-(2-(メタ)アクリロイルオキシエトキシ)フェニル]フルオレンなどのヒドロキシル基及びカルボキシル基を有しておらず、フッ素原子を含有しない(メタ)アクリレート類などが挙げられる。
ヒドロキシル基またはカルボキシル基を1つ以上有するラジカル重合性化合物(B)としては、好ましくは、フッ素原子を含有しないものが使用され、具体的には、ビスフェノールAエポキシ(メタ)アクリレート、ビスフェノールAエチレングリコールモノ(メタ)アクリレート、トリエチレングリコールモノ(メタ)アクリレート、1,3-ブタンジオールモノ(メタ)アクリレート、1,2-プロパンジオール-1-(メタ)アクリレート、テトラメチレングリコールモノ(メタ)アクリレート、プロピレングリコオールモノ(メタ)アクリレート、ネオペンチルグリコールモノ(メタ)アクリレート、トリエチレングリコールジ(メタ)アクリレート、ペンタエリスリトールジ(メタ)アクリレート、ペンタエリスリトールトリ(メタ)アクリレート、ジペンタエリスリトールジ(メタ)アクリレート、ジペンタエリスリトールトリ(メタ)アクリレート、ジペンタエリスリトールテトラ(メタ)アクリレート、2,2,2-トリス(メタ)アクリロイロキシメチルエチルコハク酸などのヒドロキシル基またはカルボキシル基を1つ以上有し、フッ素原子を含有しない(メタ)アクリレート類が挙げられる。
光ラジカル重合開始剤(E)としては光ラジカル重合を活性化する化合物であれば特に限定されず、例えば、3,3’,4,4’-テトラ(t-ブチルパーオキシカルボニル)ベンゾフェノン(製品名「BTTB」、日本油脂社製)、3,3’-ジ(t-ブチルパーオキシカルボニル)-4,4’-ジ(メトキシカルボニル)ベンゾフェノン、3,3’-ジ(メトキシカルボニル)-4,4’-ジ(t-ブチルパーオキシカルボニル)ベンゾフェノン、3,4’-ジ(t-ブチルパーオキシカルボニル)-3’,4-ジ(メトキシカルボニル)ベンゾフェノンの位置異性体混合物、t-ブチルペルオキシベンゾエート(商品名:「パーブチルZ」、日本油脂社製)などの過酸化エステル類;t-ブチルヒドロペルオキシド、ジ-t-ブチルペルオキシドなどの過酸化物類;ベンゾイン、ベンゾインメチルエーテル、ベンゾインエチルエーテル、ベンゾインイソプロピルエーテルなどのベンゾイン・ベンゾインアルキルエーテル類;アセトフェノン、2,2-ジメトキシ-2-フェニルアセトフェノン、2,2-ジエトキシ-2-フェニルアセトフェノン、1,1-ジクロロアセトフェノン、2-メチル-1-[4-(メチルチオ)フェニル]-2-モルフォリノ-プロパン-1-オン、2-ベンジル-2-ジメチルアミノ-1-(4-モルフォリノフェニル)-ブタン-1-オンなどのアセトフェノン類;2-メチルアントラキノン、2-エチルアントラキノン、2-ターシャリーブチルアントラキノン、1-クロロアントラキノン、2-アミルアントラキノンなどのアントラキノン類;2,4-ジメチルチオキサントン、2,4-ジエチルチオキサントン、2-クロロチオキサントン、2,4-イソプロピルチオキサントンなどのチオキサントン類;アセトフェノンジメチルケタール、ベンジルジメチルケタールなどのケタール類;ベンゾフェノンなどのベンゾフェノン類;キサントン類;1,7-ビス(9-アクリジニル)ヘプタン;Irgacure784(CIBA社製)などのチタノセン化合物;芳香族ヨードニウム塩、芳香族スルホニウム塩;などの公知の光重合開始剤を単独で又は2種以上を組み合わせて用いることができる。
増感色素(G)としては、光重合開始剤を増感するものであれば特に限定されず、公知のものを使用できる。増感色素として、例えば、チオピリリウム塩系色素、メロシアニン系色素、キノリン系色素、スチリルキノリン系色素、ケトクマリン系色素、チオキサンテン系色素、キサンテン系色素、オキソノール系色素、シアニン系色素、ローダミン系色素、ピリリウム塩系色素等が例示される。可視光増感色素は、光学素子のような高透明性が要求される場合には、ホログラム記録後の後工程、加熱や紫外線照射により分解し無色透明になるものが好ましい。増感色素は単独で又は2種以上組み合わせて使用できる。なかでも、シアニン系色素が好ましく用いられ、具体的には、下記式(1)で表される3-エチル-2-[3-(3-エチル-5-フェニル-2-ベンゾキサゾリニリデン)プロペニル]-5-フェニルベンゾキサゾィウムブロミド{3-Ethyl-2-[3-(3-ethyl-5-phenyl-2-benzoxazolinylidene)propenyl]-5-phenylbenzoxazolium bromide、シアニン色素1}が挙げられる。
本発明の体積ホログラム記録媒体は、基板と、該基板間に挟持された上記体積ホログラム記録用感光性組成物からなる体積ホログラム記録層とを有する。体積ホログラム記録媒体は、上記体積ホログラム記録用感光性組成物を基板で挟み込み、加熱処理及び/又は一定時間熟成させることによって得られる。本発明の体積ホログラム記録媒体は、硬化収縮が著しく抑制され、高記録容量、高屈折率変調かつ光照射による体積変化の少ないホログラム記録媒体である。
体積ホログラム記録層の厚みは、例えば、1~2000μm、好ましくは10~1000μmである。一般に、この厚みが薄すぎると、角度選択性の低いホログラムになりやすく、逆に厚い場合には、角度選択性が高いホログラムが得られる。
基材(基板)としては、可視光に対して透明性を有するものであればよく、例えば、ガラス板;シクロオレフィン系ポリマーフィルム(例えば、ダイセル化学工業社製の「TOPAS」等)、ポリエチレンフィルム、ポリプロピレンフィルム、ポリフッ化エチレン系フィルム、ポリフッ化ビニリデンフィルム、ポリ塩化ビニルフィルム、ポリ塩化ビニリデンフィルム、ポリメチルメタクリレートフィルム、ポリカーボネート(PC)フィルム、ポリエーテルスルホンフィルム、ポリエーテルケトンフィルム、ポリアミドフィルム、テトラフルオロエチレン-パーフルオロアルキルビニルエーテル共重合フィルム、ポリエチレンテレフタレート(PET)フィルム等のポリエステルフィルム、ポリイミドフィルム等のプラスチックフィルム(シートを含む)などが挙げられ、これらの基材は、同一、又は異種の組合せで用いることができる。
本発明の体積ホログラム記録媒体は、上記体積ホログラム記録用感光性組成物を上記基板で挟み込み、加熱処理及び/又は一定時間熟成させることにより製造する。加熱処理及び熟成の時間は、系内の三次元ポリマーマトリックス前駆体材料の構成成分の硬化反応が終了する時間とすることができる。加熱処理後に熟成することにより、優れた耐湿性、熱安定性を有し、さらに硬化収縮が抑制された体積ホログラム媒体を得ることができる。
具体的には、加熱処理は、40℃以上300℃以下で行うことが好ましく、特に40℃以上150℃以下で行うことがより好ましい。加熱時間は、例えば、10分~5時間であり、好ましくは10分~3時間である。加熱時間が10分より短いと、後の熟成工程を施しても硬化反応が終了しないので、好ましくない場合がある。加熱時間が5時間を超えると、ラジカル重合性化合物の反応が進行することがあり、十分なホログラム特性を得ることができない場合がある。
熟成は、例えば、-15℃以上40℃未満、好ましくは、0℃以上35℃以下(室温)にて、遮光条件下でカチオン重合反応性化合物を暗反応させて行う。熟成することにより、媒体中での反応を落ち着かせることができる。また、上記加熱処理で硬化が不十分な場合に、熟成することにより体積ホログラム記録層の硬化反応を終了させることができる。本願において硬化反応の終了は、例えば、形成された膜を、赤外スペクトル測定器(IR)やDSC等を用いて評価することにより、マトリックスの硬化状態を確認することができる。また、熟成工程は、加熱処理後の体積ホログラム記録媒体を十分に室温まで戻す工程も含む。加熱後、体積ホログラム記録媒体を十分に室温まで戻すことにより、安定したホログラム特性を得ることができる。
本発明のホログラム記録方法では、体積ホログラム記録媒体にレーザー光を照射させて前記ラジカル重合性化合物を重合させる。本発明のホログラム記録方法でホログラムを記録した後、好ましくは増感色素が分解し、記録後の透過率が80%以上とできる。体積ホログラム記録媒体にレーザー光を照射する方法としては、公知の方法を用いることができる。例えば、体積ホログラム記録媒体の体積ホログラム記録材料層に原版を密着させ、透明な基材フィルムの側から可視光、あるいは紫外光や電子線のような電離放射線を用いて干渉露光を行うことにより体積ホログラムを記録する方法(密着露光方式)や、媒体がガラスやフィルムに挟まれている場合に、媒体側からレーザー光を入射し、原版からの反射レーザー光と入射レーザー光との干渉により記録する方法(1光束干渉)や、レーザー光を2方向に分割し、一方を感材に直接入射し、他方は記録したい情報を持つ物体を通した光(情報光)を入射することにより記録する方法(2光束干渉)、情報光と参照光を同軸から照射する方法(コリニア方式)などが挙げられる。
図1に実験で用いた光学系の概略図を示す。光源は532nm半導体レーザーを用い、ミラー(M)、スペーシャルフィルター(OL及びPh)、平凸レンズ(PCL)、波長板(PP)を介し、ビームスプリッター(BS)で2つの光に分けた。BSで分けられた2つの光をミラーを介し、サンプルに対してそれぞれ30°、30°で入射、干渉させた。回折光及び透過光の強度はパワーメーター(PM:株式会社エーディーシー社製)にてそれぞれ検出した。
(回折効率)
二光束干渉法で記録したホログラムの回折効率をパワーメーターを用いて測定した。口径5φの532nm半導体レーザーを30°の角度で入射し、透過光と回折光を検出した。体積ホログラム記録媒体を-5°~5°の範囲で軸回転させ、回折光強度が最も高くなる位置で回折効率ηを下記(式1)を用いて算出した。
η=L1/(L0+L1) (式1)
(透過光強度:L0、回折光強度:L1)
体積ホログラム記録媒体を10°傾けて設置し、記録光と参照光の角度をそれぞれ20°と40°でホログラム記録を行った。その後、参照光を40°の角度で入射させ、最大回折効率を示す角度を検出した(θ1)。収縮がない場合には、その際に得られる最大回折効率の示す角度は40°であるが、収縮が起こることで40°からのずれが生じる。また、同様にして、記録光のみを20°の角度で入射させ、最大回折効率を示す角度(θ2)を検出した。これらの角度を用いて、以下の(式2)、(式3)より記録媒体の厚み方向のグレーティングベクトル(K1およびK2)を求め、(式4)より収縮率を算出した。
K1=(2π/λ){(n2-sin2θ1)1/2)-(n2-sin2θ2)1/2)}
… (式2)
(λ:記録波長、n:記録層の屈折率、θ1,θ2:記録前の入射角:40°,20°)
K2=(2π/λ){(n2-sin2θ1 ')1/2)-(n2-sin2θ2 ')1/2)}
… (式3)
(λ:記録波長、n:記録層の屈折率、θ1 ',θ2 ':回折効率が最大となる入射角)
収縮率(%)=(K1-K2)/K1 × 100 … (式4)
(記録前:K1、記録後:K2)
ラジカル重合性化合物としてOH基を持つ単官能のアクリレート化合物である1,2-プロパンジオール-1-アクリレートを10重量部、4官能のアクリレート化合物であるペンタエリスリトールテトラアクリレートを40重量部、カチオン重合性化合物として2官能の脂環式エポキシ化合物(3,4,3’,4’-ジエポキシビシクロヘキシル)を25重量部、可塑剤としてセバシン酸ジエチルを25重量部、光ラジカル重合開始剤として3,3’,4,4’-テトラ(t-ブチルパーオキシカルボニル)ベンゾフェノンをラジカル重合性化合物50重量部に対して10重量部、熱酸発生剤としてトリフェニルスルホニウム塩(商品名「サンエイドSI-60L」、三新化学社製)をカチオン重合性化合物25重量部に対して1重量部、増感色素として上記式(1)で表される構造を有するシアニン色素1を0.025重量部を室温下で攪拌、溶解させたものを感光液1とした。この時のOH基/アクリロイル基の比率は、0.14である。
ラジカル重合性化合物として4官能のアクリレート化合物であるペンタエリスリトールテトラアクリレートを50重量部、カチオン重合性化合物として2官能の脂環式エポキシ化合物(3,4,3’,4’-ジエポキシビシクロヘキシル)を25重量部、可塑剤としてセバシン酸ジエチルを25重量部、光ラジカル重合開始剤として3,3’,4,4’-テトラ(t-ブチルパーオキシカルボニル)ベンゾフェノンをラジカル重合性化合物50重量部に対して10重量部、熱酸発生剤としてトリフェニルスルホニウム塩(商品名「サンエイドSI-60L」、三新化学社製)をカチオン重合性化合物25重量部に対して1重量部、増感色素としてシアニン色素1を0.1重量部を室温下で攪拌、溶解させたものを感光液C1とした。
この感光液C1を用いて実施例1と同様にし透過型ホログラムを記録すると最大回折効率60%、硬化収縮率1.01%であった(532nm、光強度:1mW/cm2、露光量100mJ/cm2)。
ラジカル重合性化合物としてOH基を持つ単官能のアクレート化合物である1,2-プロパンジオール-1-アクリレートを50重量部、カチオン重合性化合物として2官能の脂環式エポキシ化合物(3,4,3’,4’-ジエポキシビシクロヘキシル)を25重量部、可塑剤としてセバシン酸ジエチルを25重量部、光ラジカル重合開始剤として3,3’,4,4’-テトラ(t-ブチルパーオキシカルボニル)ベンゾフェノンをラジカル重合性化合物50重量部に対して10重量部、熱酸発生剤としてトリフェニルスルホニウム塩(商品名「サンエイドSI-60L」、三新化学社製)をカチオン重合性化合物25重量部に対して1重量部、増感色素としてシアニン色素1を0.1重量部を室温下で攪拌、溶解させたものを感光液C6とした。
この感光液C6を用いて実施例1と同様にして透過型ホログラムを記録すると最大回折効率20%、硬化収縮率1.59%であった(532nm、光強度:1mW/cm2、露光量100mJ/cm2)
ラジカル重合性化合物としてOH基を持つ単官能のアクレート化合物である1,2-プロパンジオール-1-アクリレートを40重量部、4官能のアクリレート化合物であるペンタエリスリトールテトラアクリレートを10重量部、カチオン重合性化合物として2官能の脂環式エポキシ化合物(3,4,3’,4’-ジエポキシビシクロヘキシル)を25重量部、可塑剤としてセバシン酸ジエチルを25重量部、光ラジカル重合開始剤として3,3’,4,4’-テトラ(t-ブチルパーオキシカルボニル)ベンゾフェノンをラジカル重合性化合物50重量部に対して10重量部、熱酸発生剤としてトリフェニルスルホニウム塩(商品名「サンエイドSI-60L」、三新化学社製)をカチオン重合性化合物25重量部に対して1重量部、増感色素としてシアニン色素1を0.1重量部を室温下で攪拌、溶解させたものを感光液22とした。
この感光液22を用いて実施例1と同様にして透過型ホログラムを記録すると最大回折効率29%、硬化収縮率1.32%であった(532nm、光強度:1mW/cm2、露光量100mJ/cm2)
表1~4に示す配合で種々のラジカル重合性モノマー、およびカチオン重合性化合物を用い、実施例1と同様にして感光液2~21,23、C2~C5,C7~C17を調製した。なお、表において、各化合物の配合量は重量部で示した。
A1:ペンタエリスリトールテトラアクリレート
A2:o-フェニルフェノールアクリレート
A3:9,9-ビス[4-(2-アクリロイルオキシエトキシ)フェニル]フルオレン
A4:エトキシ化ビスフェノールAジアクリレート
A5:スチレン
B1:1,2-プロパンジオール-1-アクリレート
B2:ペンタエリスリトールトリアクリレート
B3:ビスフェノールAエポキシアクリレート
B4:2,2,2-トリスアクリロイロキシメチルエチルコハク酸
C1:3,4,3’,4’-ジエポキシビシクロヘキシル
C2:2,2-ビス(3,4-エポキシシクロヘキシル)プロパン
C3:2,2-ビス(3,4-エポキシシクロヘキシル)-1,3-ヘキサフルオロプロパン
C4:ビス(3,4-エポキシシクロヘキシル)メタン
C5:1-[1,1-ビス(3,4-エポキシシクロヘキシル)]エチルベンゼン
C6:3,4-エポキシシクロヘキシルメチル(3,4-エポキシ)シクロヘキサンカルボキシレート(商品名「セロキサイド2021P」、ダイセル化学工業社製)
C7:シクロヘキセンオキサイド(和光純薬社製)
C8:オキサノルボルネンジビニルエーテル
C9:ジ[1-エチル(3-オキセタニル)]メチルエーテル(商品名「DOX」、東亞合成社製)
D1:セバシン酸ジエチル(和光純薬社製)
E1:3,3’,4,4’-テトラ(t-ブチルパーオキシカルボニル)ベンゾフェノン
(商品名「BTTB」、日本油脂社製)
F1:サンエイドSI-60L(三新化学社製)
G1:シアニン色素1[上記式(1)の化合物]
Claims (10)
- カチオン重合性化合物(C)と熱酸発生剤(F)とを含有する三次元架橋ポリマーマトリックス前駆体材料(I)と、2種以上のラジカル重合性化合物(X)と、光ラジカル重合開始剤(E)と、増感色素(G)とを含有することを特徴とする体積ホログラム記録用感光性組成物。
- 前記三次元架橋ポリマーマトリックス前駆体材料(I)が、脂環を構成する隣接する2つの炭素原子と酸素原子とで構成されるエポキシ基を有する脂環エポキシ化合物(Ia)と、前記脂環エポキシ化合物(Ia)以外のエポキシ化合物(Ib-1)、オキセタン化合物(Ib-2)、ビニルエーテル化合物(Ib-3)からなる群から選択されたいずれか1種または2種以上のカチオン重合性化合物を含有する、請求項1記載の体積ホログラム記録用感光性組成物。
- 前記ラジカル重合性化合物(X)が、ラジカル重合可能なエチレン性不飽和結合を有し、且つヒドロキシル基またはカルボシキシル基を1つ以上有するラジカル重合性化合物(B)と、ラジカル重合可能なエチレン性不飽和結合を有し、且つヒドロキシル基及びカルボキシル基を有していないラジカル重合性化合物(A)とを含有する、請求項1又は2記載の体積型ホログラム記録用感光性組成物。
- 前記ラジカル重合性化合物(X)が、前記不飽和結合の総量に対するヒドロキシル基及びカルボキシル基の総量のモル比率(OH基及びCOOH基/不飽和結合)が0.01~0.5の範囲内になるようにラジカル重合性化合物(A)とラジカル重合性化合物(B)とを組み合わせる、請求項3記載の体積型ホログラム記録用感光性組成物。
- 請求項1~4の何れか1項に記載の体積ホログラム記録用感光性組成物を加熱処理することにより得られるラジカル重合性化合物、三次元架橋ポリマーマトリックス、光ラジカル重合開始剤、および増感色素を含有する体積型ホログラム記録用感光性組成物。
- 請求項1~4の何れか1項に記載の体積ホログラム記録用感光性組成物を基板で挟み込み、加熱処理及び/又は一定時間熟成させることによって得られる体積ホログラム記録媒体。
- 基板と、該基板間に挟持された請求項5記載の体積ホログラム記録用感光性組成物からなる体積ホログラム記録層とを有する体積ホログラム記録媒体。
- 請求項1~4のいずれか1項に記載の体積ホログラム記録用感光性組成物を基板で挟み込み、加熱処理及び/又は一定時間熟成させることを特徴とする体積ホログラム記録媒体の製造方法。
- 請求項6又は7記載の体積ホログラム記録媒体にレーザー光を照射させて前記ラジカル重合性化合物を重合させることを特徴とするホログラム記録方法。
- 請求項9記載の方法でホログラムを記録した後の透過率が80%以上であることを特徴とする体積ホログラム記録媒体。
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WO2013161524A1 (ja) * | 2012-04-23 | 2013-10-31 | 株式会社ダイセル | 体積ホログラム記録用感光性組成物、これを用いた体積ホログラム記録媒体及びその製造方法、並びにホログラム記録方法 |
WO2014061559A1 (ja) * | 2012-10-15 | 2014-04-24 | 株式会社ダイセル | 体積ホログラム記録層形成用感光性組成物 |
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