WO2003081344A1 - Composition de photopolymere destinee a un materiau d'enregistrement holographique, support d'enregistrement holographique et processus de production de celui-ci - Google Patents

Composition de photopolymere destinee a un materiau d'enregistrement holographique, support d'enregistrement holographique et processus de production de celui-ci Download PDF

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Publication number
WO2003081344A1
WO2003081344A1 PCT/JP2003/003576 JP0303576W WO03081344A1 WO 2003081344 A1 WO2003081344 A1 WO 2003081344A1 JP 0303576 W JP0303576 W JP 0303576W WO 03081344 A1 WO03081344 A1 WO 03081344A1
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WIPO (PCT)
Prior art keywords
derivative
hologram recording
recording material
photopolymer composition
polymerizable compound
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PCT/JP2003/003576
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English (en)
Japanese (ja)
Inventor
Naruhito Iwasa
Tetsuyuki Saika
Yasuo Matoba
Kouji Aoki
Takashi Matsuo
Kazunori Yokoyama
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Daiso Co., Ltd.
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Application filed by Daiso Co., Ltd. filed Critical Daiso Co., Ltd.
Priority to JP2003579014A priority Critical patent/JP4325404B2/ja
Priority to AU2003221077A priority patent/AU2003221077A1/en
Publication of WO2003081344A1 publication Critical patent/WO2003081344A1/fr

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    • 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
    • G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
    • G03F7/001—Phase modulating patterns, e.g. refractive index patterns
    • 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 novel photopolymer composition for a volume phase hologram recording material used for recording the intensity distribution of light and dark of a light interference pattern as a change in refractive index, and particularly the basic characteristics required for a hologram.
  • the present invention relates to a photopolymer composition for a hologram recording material capable of producing a recording medium having excellent sensitivity, transparency, and diffraction efficiency, and further relates to a hologram recording medium obtained therefrom and a method for producing the same.
  • a hologram is a pattern in which the interference pattern of coherent light from a laser is recorded on a light-sensitive material or the like by means of refractive index modulation. Since it has multiple functions, it has an optical element, a stereoscopic image display, interference measurement, It is used for a wide variety of purposes such as processing.
  • photosensitive materials such as silver halide emulsions and gelatin dichromate have been generally used.
  • hologram recording materials that have the characteristics required of hologram recording materials, such as high weather resistance, high storage stability, high resolution, and high diffraction efficiency, without complicated processing, include, for example, Photopolymer resin composition for hologram recording consisting of cyclohexyl methacrylate, N-vinyl canolepazole and benzoin methyl ether, or butyl methacrylate and ethylene glycol dimethacrylate as photopolymerizable monomers 1-phenylnaphtha as an inert component that does not Photopolymerizable recording materials based on ren and photoinitiator (US Patent
  • An object of the present invention is to provide a photopolymer composition for a volume phase type photogram recording material used for recording a light-dark intensity distribution of an optical interference pattern as a change in a refractive index.
  • An object of the present invention is to provide a photopolymer composition for a hologram recording material, which has high transparency in addition to excellent diffraction efficiency and high sensitivity. Disclosure of the invention
  • the present invention relates to a photopolymer composition for a volume phase type photogram recording material used for recording a bright intensity distribution of an interference pattern obtained by interfering light as a change in refractive index.
  • a binder polymer soluble in an organic solvent (A) a polymerizable compound having an ethylenically unsaturated double bond (B), a photopolymerization initiator (C), and a photosensitizing dye (D) And a supersensitizer (E), and optionally a plasticizer (F).
  • a preferred example of the photopolymer composition for a hologram recording material according to the present invention is that the refractive index of the polymerizable compound (B) is larger than that of the pinda-polymer (A) by 0.01 or more so that hologram recording is possible. , Or small.
  • a plasticizer (F.) is included, the refractive index of the polymerizable compound (B) is larger than the weighted average of the refractive index of the binder polymer (A) and that of the plasticizer (F) by 0.01 or more.
  • the binder polymer (A) used in the present invention has good compatibility with the polymerizable compound (B).
  • the binder polymer (A) also has good compatibility with the plasticizer (F), and the organic polymer Any material that does not contain an insoluble portion in the medium and can be completely dissolved may be used.
  • Typical examples include a homopolymer or copolymer obtained by polymerizing a monomer having an ethylenically unsaturated double bond, a condensation polymer of a diphenol compound and a dicarboxylic acid compound, and a carbonic ester group in the molecule. And a polymer having a —SO 2 — group in the molecule, a cell opening derivative, and a combination of two or more of these.
  • the binder polymer (A) used in the present invention may be a thermoplastic resin or a thermosetting resin, but the former is preferred.
  • thermoplastic resin as the inner polymer (A) has good compatibility with the polymerizable compound (B) and the plasticizer (F) and can be completely dissolved in an organic solvent without containing an insoluble portion.
  • Representative examples are a homopolymer or copolymer obtained by polymerizing a monomer having an ethylenically unsaturated double bond, a condensation polymer of a diphenol conjugate and a dicarbone conjugate, and carbonic acid in the molecule. It is selected from the group consisting of a polymer having an ester group, a polymer having one SO 2 group in the molecule, a cellulose derivative, and a combination of two or more of these.
  • thermoplastic resin examples include polyvinyl acetate, polyvinyl butyrate, polyvinyl formal, polyvinyl carbazole, polyacrylic acid, polymethacrylic acid, polymethyl acrylate, polymethyl methacrylate, polyethyl acrylate, and polybutyl acrylate.
  • thermoplastic resin may be used alone or in combination of two or more.
  • polyvinyl acetate, polyvinyl butyrate, cellulose acetate butyrate, ethylene-vinyl acetate copolymer, polymethyl methacrylate, polystyrene, Marl or the like is preferably used.
  • a copolymer of (meth) acrylic acid cyclic aliphatic ester and methyl (meth) acrylate is preferably used.
  • composition ratio is preferably from 5 to 95:95 to 5, more preferably from 10 to 90:90 to: L0 in terms of molar ratio (same ester: same acrylate).
  • the (meth) acrylic acid cycloaliphatic ester constituting the copolymer of (meth) acrylic acid cycloaliphatic ester and methyl (meth) acrylate is represented by the following general formula [I]. Good.
  • R 5 represents a hydrogen atom or a methyl group.
  • R 2 are the same or different and represent a hydrogen atom or a lower alkyl group.
  • k is an integer of 0 to 6
  • m is an integer of 2 to 6
  • n is an integer of 1 to 5 where m> n.
  • Any hydrogen atom in k, (CH 2 ) m and (CH 2 ) n may be substituted with a lower alkyl group.
  • Two hydrogens bonded to different carbons in the alkylene chain (C) m may be substituted at both ends of another alkylene chain having 1 to 8 carbon atoms to form another cycloalkane ring. Any hydrogen in this other cycloalkane ring may be further substituted with a lower alkyl group.
  • One of the carbons in the alkylene chain (C3 ⁇ 4) n has a hydroxyl group, and (meth) acrylic acid is ester-bonded to this hydroxyl group. Indicates an ester bond thus formed. ]
  • the cycloaliphatic portion of the (meth) acrylic acid cyclic aliphatic ester constituting the copolymer of (meth) acrylic acid cyclic aliphatic ester and methyl (meth) acrylate has a bornyl skeleton, isopolnyl skeleton, or norpolnyl skeleton May be
  • Examples of (meth) acrylic cycloaliphatic esters that constitute a copolymer of (meth) acrylic acid cycloaliphatic ester and methyl (meth) acrylate are porunyl (meth) acrylate, isobornyl (meth) acrylate, norpolnil (Meth) acrylate.
  • the (meth) acrylic acid cyclic aliphatic ester may be one kind or two or more kinds.
  • the copolymer is a terpolymer or more of two or more kinds of (meth) acrylic acid cycloaliphatic esters and methyl (meth) acrylate.
  • the copolymer of (meth) acrylic acid cyclic aliphatic ester and methyl (meth) acrylate may be used alone or in a combination of two or more.
  • the polymerizable compound (B) having an ethylenically unsaturated double bond used in the present invention is preferably a radical polymerizable compound.
  • the polymerizable compound (B) may be a monomer or an oligomer of a dimer or trimer thereof.
  • the polymerizable compound (B) may be any compound having good compatibility with the binder polymer (A) and the plasticizer (F), and may be a (meth) acrylate monomer and its oligomer, a vinyl monomer and its oligomer, And may be selected from the group consisting of a combination of two or more of these.
  • (meth) acrylate monomers include methyl methacrylate, ethyl methacrylate, n-butyl methacrylate, isobutyl methacrylate, 2-ethylhexyl methacrylate, isodecyl methacrylate, n-lauryl methacrylate, and n-stearyl.
  • Examples include rutetraacrylate, ditrimethylolpropanetetramethacrylate, ditrimethylol-propanetetraacrylate, tetramethylolmethanetetraacrylate, dipentaerythritolhexamethacrylate, and dipentaerythritolhexaacrylate.
  • the radical polymerizable compound may be a dimer or trimer oligomer of the above (meth) acrylate monomer.
  • vinyl monomer examples include vinyl acetate, 4-vinylaniline, 9-vinylanthracene, 4-vinylanisole, vinylbenzaldehyde, vinylbenzoate, vinylbenzyl chloride, 4-vinylbiphenyl, vinyl bromide, N-vinylcaprolactam, and vinyl chloride.
  • the polymerizable compound (B) preferably has a refractive index of 1.55 or more.
  • the polymerizable compound (B) may also have a bis (thiophenyl) sulfide skeleton, a halogenated phenyl skeleton, a phenolazole skeleton, or a fluorene skeleton.
  • a monomer having a bis (thiophenyl) sulfide skeleton Is bis (4-acryloylthiophenyl) sulfide, bis (4-acryloylthio-12-cyclohexene-1-yl) sulfide, bis (2-acryloylthioenyl) sulfide, bis (3-acrylyl) Ruthiopyridyl) sulfide, bis (5-acryloylthioviranyl) sulfide, bis (5- (meth) acryloylthio 1,4-dithianyl) sulfide, etc.
  • an oligomer of about a dimer or a trimer of the above compound may be used. These may be used alone or in combination of two or more.
  • the monomer having a halogenated phenyl skeleton examples include 2,4-dibromophenyl (meth) acrylate, 2,6-dibromophenyl (meth) acrylate, 4,6-dichloro-1-vinylbenzene, and 2,6-dibromophenyl (meth) acrylate.
  • the oligomer may be a dimer or trimer of the above compound. These can be used alone You may use in combination of the above.
  • the monomer having a carpazole skeleton include: 1-vinylcarbazole, 2-vinylcarbazole, 3-vinylcarbazole, 4-vinylcarbazole, 9-vinylcarbazole, 1- (meth) acryloyloxycarbazoline 2- (meth) acryloyloxycarbazole, 3- (meth) acryloyloxycarbazole, 4- (meth) acryloyloxycarbazole, 9- (meta) ) Acryloyloxycarbazole, 1,9-divinylcarbazole, 1,5,9-trivinylcarbazole, 2,7-di (meth) acryloyloxycarbazole, 2-methyl-1 , 9-divinylcarbazole, 1,9-di (meth) acryloyloxycarbazole and the like.
  • oligomers such as dimers or trimers of the above compounds may be used.
  • the monomer having a fluorene skeleton may be represented by the following general formula [II].
  • R 3 and R 4 represent the same or different monovalent organic groups, and at least one of them has a (meth) acryloyl group or a (meth) acryloyloxy group at a terminal.
  • ⁇ ⁇ and M 2 are the same or different from each other and are represented by one (OR 6 ) n — (R 6 is a lower alkylene group which may have a hydroxyl group, n is 0, 1 or 2) ′ It means an organic group or a single bond.
  • X 2 are the same or different from each other, and represent a hydrogen atom or a lower alkyl group.
  • the organic group having no (meth) acryloyl group has 1 carbon atom. It may be up to 3 lower alkyl groups.
  • n the number of carbon atoms of the lower alkylene group R 6 is preferably 1-3, more preferably 1-2.
  • R 6 include oxymethylene, oxyethylene, oxypropylene, oxybutylene and the like, and examples of 1 (OR 6 ) n — include dioxymethylene and dioxethylene.
  • the hydroxyl group may be located at any position of the alkylene group, and the alkylene having a hydroxyl group is, for example, (2-hydroxy) propylene.
  • the organic group and X 2 may be an alkyl group having 1 to 5 carbon atoms such as methyl, ethyl and propyl.
  • the monomer having a fluorene skeleton of the polymerizable compound (B) include 9,9-bis (4- (meth) acryloyloxyphenyl) fluorene and 9,9-bis (4- (meta) Acryloyloxymethoxyphenyl) fluorene, 9,9-bis [4- (2- (meth) acryloyloxyethoxy) phenyl] fluorene, 9,9-bis [4- (meth) acryloyl 1-Methoxyphenyl] fluorene, 9,9-bis [4- (meth) acryloyloxymethoxy-3- 3-methylphenyl] fluorene, 9,9-bis [4- (2- (meth) acryloyl 1-3-Methylphenyl] fluorene, 9,9_bis (4- (meth) acryloyloxy-3-3-ethylphenyl) fluorene, 9,9-bis (4- (meth) acryloyloxy
  • an organic group R is required. and R 4 is an acryloyl group and an acryloyloxy group, and n is 0, 1 or 2 and n is 1 or 2 in — ( ⁇ R 6 ) n— of M 2 Is preferably a lower alkylene group R having 1 to 2 carbon atoms, and and X 2 is preferably a hydrogen atom.
  • preferred compounds include the following:
  • the plasticizer (F) used as an optional component in the present invention is a compound that is non-reactive with the binder polymer (A) and the polymerizable compound (B).
  • the plasticizer (F) include phthalic esters represented by dimethyl phthalate, getyl phthalate and octyl phthalate; dimethyl adipate, dibutyl adipate, dimethyl sebacate, getyl sebacate, dibutyl sebacate, getyl succinate Aliphatic dibasic acid esters such as triacetate; orthophosphates such as trimethyl phosphate, triethyl phosphate, triphenyl phosphate and tricresyl phosphate; glyceryl triacetate and 2-ethylhexyl acetate Inactive compounds such as acetic acid esters represented by phosphites represented by triphenyl phosphite and dibutyl hydrogen phosphite. Further, an alkylene glycol alkyl
  • alkylene glycol alkyl ether Typical examples are ethylene dimethyl dimethyl ether, ethylene glycol dimethyl ether, ethylene glycol dipropyl ether, ethylene diol glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, and diethylene diol.
  • polyethylene glycol or silicone oil having a weight average molecular weight of 1000 or less can also be used.
  • the above examples may be used alone or in combination of two or more.
  • the amount of the plasticizer (F) added is preferably about 0.1 to 50 parts by weight in 100 parts by weight of the total of the binder polymer (A), the polymerizable compound (B) and the plasticizer (F). It is.
  • the binder polymer (A) soluble in an organic solvent is a thermoplastic resin
  • the polymerizable compound (B) having an ethylenically unsaturated double bond is a radical polymerizable compound; It also contains a plasticizer (F).
  • Examples of the photopolymerization initiator (C) used in the present invention include carbonyl compounds, organotin compounds, alkylaryl boron salts, ionic salts, iron-allene complexes, trihalogenomethyl-substituted triazine compounds, and organic peroxides. Oxides, bisimidazole derivatives, titanocene compounds and the like are preferably used.
  • Examples of the carbonyl compound include benzyl, benzoinethyl ether, benzophenone, and ethoxyacetophenone.
  • organotin compound examples include tributylbenzyltin.
  • alkylaryl boron salt examples include tetrabutylammonium triphenylbutylporate and triphenyl-n-butylporate.
  • Diphenyl salt may be mentioned as an example of the salt.
  • trioctogenomethyl-substituted triazine compounds include tris (trimethyl) methyl triazine.
  • bisimidazole derivatives examples include 2,2,1-bis (0-chlorophenyl) 1.4,4 ', 5,5,1-tetraphenyl-1,1, -biimidazole and bis (2,4,5-triphenyl) imidazolyl. .
  • titanocene compound bis (7-5-2,4-cyclopentene-1-1-fur) -bis (2,6-difluoro-3-(1H-pyrrol-1--1-yl) -phenyl) titanium is Can be illustrated.
  • the photosensitizing dye (D) used in the present invention includes lasers used for recording holograms: He-Ne (wavelength 633 nm), Ar (wavelengths 515, 488 nm). ), YAG (wavelength 532 nm), He-Cd (wavelength 442 nm), etc., which absorbs laser light are good, and show spectral sensitization to photopolymerization initiator (C) Those are preferred.
  • a photosensitizing dye for example, mihirageton, acridine yellow, merocyanine, methylene blue, camphorquinone, eosin, weakened lipoxylated rose bengal and the like are preferably used.
  • the photosensitizing dye may be any as long as it absorbs light in the visible region.
  • ketocoumarin derivatives include the following: 3, 3'-Carponylbis (7-Jetylaminocoumarin),
  • merocyanine derivative examples include the following:
  • sensitizing dyes include 3,3 ', 4,4'-tetra (tert-butylperoxycarbonyl) benzophenone, and NKX 653, a photosensitizing dye manufactured by Nippon Kogaku Dyestuff Research Institute.
  • NKX3883, NKX 1880, NKX 1595, NKX 1695, M79, NK85, NK 1046, NK4 256, NK1886, NK1473, NK1474, NK4795, NK42 76, NK4278, NK91, NK1046, NK1237, NK1420, NK590, etc. are preferred.
  • the combination of the carbonyl compound and the photosensitizing dye include benzyl monomethyl ketone and benzyl acridine yellow.
  • a photosensitizing dye to be combined with the amine compound weakened lipoxylated rose bengal is preferable.
  • a cyanine dye such as cyanines, isocyanines, and pseudocynins is preferable.
  • the addition amount of the photopolymerization initiator (C) in the composition of the present invention is usually 1 to 20% by weight, preferably 100% by weight of the total of the binder polymer (A) and the polymerizable compound (B). Is about 0.3 to 15% by weight.
  • the composition of the present invention contains a plasticizer (F)
  • the photopolymerization initiator (B) is added to a total of 100 parts by weight of the binder polymer (A), the polymerizable compound (B) and the plasticizer (F).
  • the addition amount of C) is usually about 0.1 to 15% by weight, preferably about 0.3 to 10% by weight.
  • the amount of the photosensitizing dye (D) ′ added to the composition of the present invention is usually 0.01% based on 100 parts by weight of the total of the binder polymer (A) and the polymerizable compound (B). It is about 2% by weight, preferably about 0.03 to 0.15% by weight.
  • the composition of the present invention contains the plasticizer (F)
  • the photosensitizing dye (100 parts by weight in total) of the binder polymer (A), the polymerizable compound (B) and the plasticizer (F) is used.
  • the amount of D) added is usually about 0.01 to 1% by weight, preferably about 0.03 to 0.8% by weight.
  • the supersensitizer (E) used in the present invention does not absorb the light of the wavelength oscillated by the laser used for hologram recording, and when the photosensitizing dye (D) is not added, Preference is given to those which do not themselves exhibit a spectral sensitizing effect on the photopolymerization initiator (C).
  • supersensitizers include basestyryl derivatives, amine compounds and the like. These may be used alone or in combination of two or more. Examples of the base styryl derivative include the following:
  • Examples of the amine compound include the following:
  • Triethylamine pyridine, 2-aminopyridine, 1-aminopiperidine, N-aminophthalimide, 2-aminomethylviridine, 5-amino-2-methoxypyridine.
  • Specific examples of the combination of the photosensitizing dye and the supersensitizer include cyanine dyes, styryl dyes, merocyanine dyes, styryl dyes, coumarin dyes, base styryl dyes, and ketocoumarin dyes. — Amine compounds and the like.
  • the supersensitizer (E) is usually added in an amount of 0.01 to 1.0 with respect to 100 parts by weight of the total of the binder polymer (A) and the polymerizable compound (B). It is about 3% by weight, preferably about 0.02 to 1% by weight.
  • the composition of the present invention contains a plasticizer (F)
  • the photosensitizing dye is used in a total of 100 parts by weight of the binder polymer (A), the polymerizable compound (B) and the plasticizer (F).
  • the amount of (D) added is usually about 0.01 to 1% by weight, preferably about 0.02 to 0.7% by weight.
  • the photosensitizing dye (D A) styryl derivative can be used.
  • the hologram recording material composition according to the present invention can contain additives such as a thickener, a thermal polymerization inhibitor, a chain transfer agent, etc., and a solvent, if necessary.
  • inorganic fine particles for example, Daiso Ichi Gel SP Series manufactured by Daiso Co., Ltd., Silica and Fuji Silica Gel manufactured by Fuji Silica Chemical Co., Ltd., and Shionogi Pharmaceutical Co., Ltd. You can use "Raiichi Plex”, “Aerosil” manufactured by Nippon Aerosil, “Leo mouth seal”, “Tokuseal”, “Fine seal” manufactured by Tokuyama.
  • organic fine particles for example, diaryl phthalate-based polymers which can be prepared by the methods described in JP-A-10-72510 and JP-A-10-310684, or "New material series” Ultrafine particles "PB, 200 Series” manufactured by Kao Corporation, "Bellpar Series” manufactured by Kanebo Co., Ltd. You can use "Tech Polymer Series” manufactured by Seishin Co., Ltd., "Micropal Series” manufactured by Sekisui Fine Chemical Co., Ltd., “MR Series” and “MP Series” manufactured by Soken Chemical Company.
  • the particle size of these fine particles may be smaller than the thickness of the hologram, and is usually in the range of 0.1 to 20 m. Is preferred.
  • the amount of the thickener is preferably about 0.5 to 30 parts by weight based on 100 parts by weight of the total of the thermoplastic polymer (A), the polymerizable compound (B) and the plasticizer (F). It is.
  • thermal polymerization inhibitor examples include those having a function of eliminating generated radicals, such as hydroquinone, p-methoxyphenol, tert-butylcatechol, naphthylamine, diphenylpicrylhydrazine, diphenylamine, and the like.
  • chain transfer agents include ⁇ -methylstyrene dimer, 2-mercaptobenzoxazole, 2-mercaptobenzothiazole, tert-butyl alcohol, n-butanol, isobutanol, isopropylbenzene, ethylbenzene, chloroform, methyle Tilketone, propylene, vinyl chloride, and the like.
  • Organic solvents are effective for improving viscosity and compatibility, as well as improving film forming properties.
  • Examples include acetone, xylene, toluene, methyl ethyl ketone, tetrahydrofuran, benzene, methylene chloride, dichloromethane, and chloroform. Mouth form, methanol, etc. are often used.
  • water cannot be used because it hinders viscosity adjustment, compatibility adjustment, film forming properties, and the like. Water cannot be used as a solvent, even in emulsion form.
  • the amount of the solvent used is about 1 to 150 parts by weight based on 100 parts by weight of the total of the binder polymer (A) and the polymerizable compound (B).
  • the amount of the solvent used is 100 parts by weight in total of the binder polymer (A), the polymerizable compound (B) and the plasticizer (F). Usually, it is about 0.5 to 100 parts by weight.
  • the hologram recording material composition for example, a binder polymer (A), a polymerizable compound CB), a photopolymerization initiator (C), a photosensitizing dye (D) and a supersensitizer (E), If necessary, the above-mentioned optional components including the plasticizer (F) are placed in an organic solvent-resistant container such as a glass beaker, and the whole is stirred. In this case, in order to promote the dissolution of the solid component, the composition may be heated to, for example, about 40 to 90 as long as the composition is not denatured.
  • the recording material composition is applied to one surface of a substrate, and the resulting coating film, that is, a recording layer and a substrate is formed.
  • a recording medium having a layer structure is obtained.
  • a three-layer structure is obtained by covering the recording layer on the substrate with a film-like, sheet-like, or plate-like protective material. It is preferable to use an organic solvent in the step of preparing the composition.
  • the binder polymer (A), polymerizable compound (B), photopolymerization initiator (C), photosensitizing dye (D), supersensitizer (E), and optionally plasticizer ( F) is dissolved in a solvent, and the obtained solution is applied on a substrate. Thereafter, the solvent is volatilized to form a recording layer.
  • the solvent is preferably removed by air drying or evaporation under reduced pressure before coating the protective material.
  • the substrate is made of an optically transparent material, for example, a glass plate, a plastic plate such as a polyethylene terephthalate plate, a polymethyl methacrylate plate, a polymethyl methacrylate plate, or a film.
  • the thickness of the substrate is preferably between 0.02 and 10 mm.
  • the substrate does not need to be flat, but may be bent, curved, or have an uneven structure on the surface.
  • the protective material is also made of an optically transparent material like the substrate.
  • the thickness of the protective material is preferably from 0.02 to: L 0 mm. Coating methods include gravure coating, roll coating, bar coating, and spin coating. It is preferable to apply the recording layer so that the thickness of the recording layer after removing the solvent is preferably 1 to 100 m.
  • a normal recording method can be adopted. That is, the laser beam is split into two light beams by a beam splitter or the like, and the two are combined again by using a mirror or the like to obtain an interference fringe. Alternatively, interference fringes are obtained by reflecting one laser beam with a mirror. The recording medium is placed at a position where this interference fringe can be captured. In this state, when laser light irradiation is normally performed for several seconds to several minutes, interference fringes serving as holograms are recorded on the recording medium. Amount of use are les one The first light is expressed by the product of the light intensity and the irradiation time is preferably 1 ⁇ 1 0, 0 0 O m J / cm 2 approximately. If the amount of light is less than this range, it is difficult to record, and if it exceeds this range, the diffraction efficiency of the hologram tends to decrease.
  • the recording material composition of the present invention comprises a binder polymer (A) and a polymerizable compound before exposure. (B), photopolymerization initiator (C), photosensitizing dye (D), supersensitizer (E) and optionally plasticizer) are compatible with each other.
  • the photopolymerization initiator (C) generates a polymerization active species by the spectral sensitization effect of (D) and the supersensitizer (E), and the polymerizable compound (B) is preferentially photopolymerized to polymerize. Eventually, it becomes a hologram recording layer.
  • Photopolymerization initiator (C) when a two-layer structure obtained by applying the recording material composition according to the present invention on a substrate or a three-layer structure obtained by covering a protective material on the recording layer is exposed to an interference pattern, Photopolymerization initiator (C) generates polymerization active species by spectral sensitization by photosensitizing dye (D) and supersensitizer (E) in a large part, and polymerizable compound rich in photopolymerization reactivity (B) starts photopolymerization, and that portion undergoes volume shrinkage.
  • C Photopolymerization initiator
  • D photosensitizing dye
  • E supersensitizer
  • B polymerizable compound rich in photopolymerization reactivity
  • the unpolymerized material flows from the portion having a small amount of light into the recess formed by this, and the binder polymer (A) is phase-separated from the polymerizable compound (B) and is removed to the portion having a small amount of light.
  • the photopolymerization of the polymerizable compound (B) that has diffused and moved to the portion having a large amount of light proceeds further.
  • a structure in which the polymer of the polymerizable compound (B) accumulates in the portion where the light amount is large, and conversely, a structure in which the binder-polymer (A) is accumulated in the portion where the light amount is small.
  • the plasticizer (F) when the optional plasticizer (F) is present in the system, the plasticizer (F) is a component for adjusting the viscosity and compatibility of the system, and the binder polymer (A) and the polymerizable compound ( It functions as a component to promote the separation of B).
  • the binder polymer (A) is a thermoplastic resin
  • the plasticizer (F) uniformly present in the system at the beginning of the exposure is eventually removed to the portion where the amount of light is small, that is, to the thermoplastic resin side. .
  • an interference pattern is formed as a hologram based on the composition distribution according to the amount of light, that is, the interference pattern based on the difference in refractive index between the portion containing a large amount of the thermoplastic resin and the plasticizer (F) and the portion containing a large amount of the polymerizable compound (B).
  • the photosensitizing dye (D) is a component for absorbing and spectrally sensitizing the laser beam, and functions as a catalyst for promoting radical generation of the photopolymerization initiator (C) by electron transfer or energy transfer. I do.
  • the supersensitizer (E) is a component for increasing the efficiency of spectral sensitization by the photosensitizing dye (D).
  • the normal recording method can be adopted. That is, light having a wavelength in the range of 200 to 80 O nm is divided into two light beams, one of which is referred to as a reference light and the other is irradiated with an object to be recorded.
  • the hologram recording material medium is arranged at a position where it is possible to catch the interference fringes obtained by causing the light to enter the recording object from the same plane or from the front and back surfaces to cause interference, and place the hologram recording material medium on the same medium. Record the object.
  • the laser beam is split into two light beams using a beam splitter or the like, and the two are combined again using a mirror or the like to obtain interference fringes (two-beam exposure method).
  • one laser beam is reflected by a mirror, and both the incident light and the reflected light are recombined to obtain interference fringes (one-beam exposure method).
  • a hologram created separately is placed on the optical path as a mass hologram.
  • the interference fringes may be obtained by one light beam and / or two light beam exposure methods.
  • the recording medium is placed at a position where the light and dark intensity distribution of the interference pattern thus formed can be captured. In this state, when laser light irradiation is performed for several seconds to several minutes, interference fringes that become holo-lam are recorded on the recording medium.
  • the amount of laser light used is expressed as a product of light intensity and irradiation time, and is preferably about 10,000 to 10,000 mJZ cm 2 . If the amount of light is less than this range, recording is difficult, and if it exceeds this range, the diffraction efficiency of the hologram tends to decrease.
  • the light source used in the present invention is a photopolymerization initiator (C) or a photopolymerization initiator (0 and a photosensitizing dye (D) or a photopolymerization initiator (C) and a photosensitizing dye (D).
  • Any material may be used as long as the photopolymerization initiation system composed of the combination of the color sensitizers (E) is irradiated with light emitted from the light source and causes electron transfer to induce polymerization of the polymerizable compound (B).
  • Examples of typical light sources include high-pressure mercury lamps, ultra-high-pressure mercury lamps, low-pressure mercury lamps, xenon lamps, metal halide lamps, etc. These can be used when copying master hologram information to the recording medium.
  • a laser can be used as a preferred light source.
  • the laser has a single wavelength and has coherence, so it can be used as a hologram.
  • Typical lasers have an oscillation wavelength of 200 to 80 Onm, specifically Kr (wavelength 647 nm), He-Ne (wavelength 633 nm), Ar (wavelength 515, 488 ni), YAG (wavelength 532 nm), He-Cd (wavelength 442 nm) and the like.
  • These light sources may be used alone or in combination of two or more. Further, the light source may be a continuous light, or may pulsate at a certain or arbitrary interval. The light obtained from the light source may be applied to the recording material before and after the recording in addition to when the recording is performed.
  • FIG. 1 is a schematic diagram showing an example of a transmission hologram.
  • FIG. 2 is a schematic diagram showing an example of a reflection hologram. BEST MODE FOR CARRYING OUT THE INVENTION
  • thermoplastic resin 2.5 g of vinyl acetate polymer (“Vinyl acetate polymer”, manufactured by Kishida Chemical Co., Ltd., polymerization degree 500, polymer refractive index: 1.43) was used as a viscous liquid at room temperature and pressure.
  • B bisphenoxyethanol full orange acrylate (manufactured by Osaka Gas Co., Ltd., “BPEFA”, refractive index of a single substance: 1.61) 2.2 g, plasticizer (F) Cyl acetate (manufactured by Wako Pure Chemical Industries, “ADE”, refractive index: 1.42) 1.0 g, 3,3 ', 4,4'-tetra (tert-butylpropylcarbonyl) as initiator (C) 3.75 g of 3,3,4,4'-tetra (tert-butylperoxyl-propionyl) benzophenone solid obtained by distilling off the toluene solvent of benzophenone ("BTT B-25J” manufactured by NOF CORPORATION) under reduced pressure, photosensitized Cyanine dye (NK1538, manufactured by Nippon Kogaku Dyestuffs Co.) 0.008 g, strong color A base styryl dye having an equim
  • NK1819 NK1819
  • 0035 g of acetone as a solvent were mixed at room temperature to prepare a photopolymer composition for a hologram recording material.
  • This composition is applied to one side of a 6 Omm x 6 Omm glass substrate by spin coating so that the thickness after drying is 10 to 15 m, and the solvent is removed from the coating layer by applying heat treatment. Then, a recording medium having a two-layer structure including a substrate and a recording layer was prepared.
  • the 515-nm Ar ion laser was split by a beam splitter, the angles of which were changed by a mirror, and the two were combined again to cause interference to obtain interference fringes.
  • the photosensitive plate was set at a position where the interference fringes could be captured.
  • Figures 1 and 2 show examples of transmission holograms and reflection holograms, respectively.
  • ( ⁇ ) is a laser generator
  • (BS) is a beam splitter
  • ( ⁇ ) is a mirror
  • (S) is a photosensitive plate
  • (B1) is object light
  • ( ⁇ 2) is reference light.
  • NK-85 was used as the photosensitizing dye (D) in place of M-1538 at the ratio shown in Table 1.
  • the exposure of the transmission hologram and the reflection-type Horodara beam has one light intensity on the photosensitive plate as 0. 5mWZcm 2, 5 seconds or et 80 seconds, from 2. 5m J / cm 2 as an exposure amount 4 OmJZcm 2 went. Otherwise, the same operation as in Example 1 was performed.
  • the initiator (C) was replaced by 2,2'-bis (0-chloro), instead of 3,3,4,4'-tetra (tert-butylvinyloxyl-propionyl) benzophenone.
  • Phenyl) one, four, four, five, five, one tetraphenyl -Biimidazole (Hodogaya Logistics, B-CIM) was used in combination with 2-mercaptobenzothiazole (Tokyo Kasei Kogyo, 2-mercaptobenzothiazool) in the proportions shown in Table 1.
  • the transmission type exposure hologram and the reflection-type hologram is one of the light intensity on the photosensitive plate as 0. 5mWZcm 2, 80 seconds 5 seconds, as the exposure amount 2. 5mJZcm 2 from 4 OmJ / cm 2 went. Otherwise, the same operation as in Example 1 was performed.
  • Example 3 2-mercaptobenzozoazole (manufactured by Kanto Chemical Co., Ltd., 2-benzoxazothiol) was used instead of 2-mercaptobenzozothiazole (manufactured by Tokyo Chemical Industry Co., Ltd., 2-mercaptobenzothiazool).
  • Table 1 the proportions shown in Table 1.
  • Example 1 In the composition of Example 1, instead of bisphenoxyethanol fluorenediacrylate and rate (“BPEFA” manufactured by Osaka Gas Co., Ltd.), an acrylic acid adduct of glycidyl ether of 9,9-bis (4-hydroxyphenyl) fluorene ( “ASF-400” manufactured by Nippon Steel Chemical Co., Ltd.) was used in the proportions shown in Table 1. Furthermore, transmission type Horodara exposure beam and the reflection hologram, one of the light intensity on the photosensitive plate as 0. 5mW / cm 2, 80 seconds 5 seconds, 40 m from the 2. 5mJZcm 2 as the exposure amount JZ cm 2 I went. Otherwise, the same operation as in Example 1 was performed.
  • BPEFA bisphenoxyethanol fluorenediacrylate and rate
  • Example 3 bisphenoloxyethanol full orange acrylate (manufactured by Osaka Gas Co., Ltd., "BPEFA”) was replaced by pentaerythritol triacrylate (Aldrich, pentaerythritol triacrylate) in the proportions shown in Table 1. Used in. Further, the transmission type exposure hologram and the reflection hologram, one of the light intensity on the photosensitive plate as 0. 5mWZcm 2, 80 seconds 5 seconds, as the exposure amount 2. 5 m JZ cm 2 from 40 m J / cm2. Otherwise, the same operation as in Example 1 was performed. Comparative Example 1
  • a recording photopolymer composition was prepared in which the supersensitizer "NK1819" was removed from the composition of Example 1, that is, no NK1819 was added. Otherwise, the same operation as in Example 1 was performed.
  • a recording photopolymer composition was prepared by removing the supersensitizer "NK1819" from the composition of Example 2, that is, adding no NK1819. Otherwise, the same operation as in Example 2 was performed. '
  • a recording photopolymer composition was prepared by removing the supersensitizer "NK1819" from the composition of Example 3, that is, adding no NK1819. Otherwise, the same operation as in Example 3 was performed.
  • a recording photopolymer composition was prepared by removing the supersensitizer "NK1819" from the composition of Example 4, that is, adding no NK1819. Otherwise, the same operation as in Example 4 was performed.
  • a recording photopolymer composition was prepared in which the supersensitizer "NK1819" was removed from the composition of Example 5, that is, no NK1819 was added. Otherwise, the same operation as in Example 5 was performed.
  • a recording photopolymer composition was prepared by removing the supersensitizer "NK1819" from the composition of Example 6, that is, adding no NK1819. Otherwise, the same operation as in Example 6 was performed.
  • This comparative example corresponds to that of U.S. Pat. No. 3,658,526 shown as prior art.
  • the diffraction efficiency of the transmission hologram is calculated by calculating the ratio of the incident light and the diffracted light using the optical power meter (OPTICAL POWER / ENERGY METER, MODEL 66XLA, manufactured by PH0T0DYNE).
  • OPTICAL POWER / ENERGY METER MODEL 66XLA, manufactured by PH0T0DYNE.
  • Diffraction efficiency (%) (Diffraction light intensity / Incident light intensity) X 100 c)
  • the diffraction efficiency of the reflection hologram is calculated using the UV-visible spectrophotometer (V-550, manufactured by JASCO Corporation). It was determined by measurement.
  • the transmission hologram and the reflection hologram obtained in the examples have extremely high sensitivity, their diffraction efficiency and transmittance are both high, and the hologram has no coloring and is not developed. It was bright even without fixing operation. Further, this hologram recording was performed only by refractive index modulation, not unevenness of the recording layer, and was highly transparent with almost no absorption in the visible part.
  • BPEFA bisphenoxyethanol full orange acrylate (manufactured by Osaka Gas Co., Ltd.)
  • B-CIM 2,2'-bis (0-cloth ferrule) 1-4,4,, 5,5,1-tetraflu 1,2,1-biimidazole (Hodogaya Logistics)
  • BTTB 3,3,, 4,4, -tetra (iert-butylpyroxycarbonyl) benzophenone (manufactured by NOF Corporation)
  • ASF-400 9,9-bis (4-hydroxyphenyl) fluorene adduct of dalicydyl ether with acrylic acid (manufactured by Nippon Steel Corporation)
  • Sensitivity The minimum exposure energy (mJ / cm 2 ) at which holograms began to be recorded Industrial applicability
  • a binder polymer (A) soluble in an organic solvent, a polymerizable compound (B) having an ethylenically unsaturated double bond, a photopolymerization initiator (C), a photosensitizing dye (D ) can contain a supersensitizer (E), whereby a hologram capable of recording an image with high transparency, high sensitivity and high diffraction efficiency can be produced.
  • the photopolymer composition for hologram recording according to the present invention has excellent film-forming properties, and is close to a solid even after film formation, so that a heat treatment for solidifying a fluid composition like a conventional product is required. And not. Furthermore, the diffraction efficiency is sufficiently high without performing heat treatment for amplification of diffraction efficiency after hologram recording. Therefore, the film forming operation and post-processing in the production of the hologram recording medium can be simplified and the workability is excellent.
  • the recording medium after hologram recording has high transparency, and the binder polymer (A) and the polymer of the polymerizable compound (B) both exist as a sufficiently high molecular weight after only one exposure.
  • the binder polymer (A) and the polymer of the polymerizable compound (B) both exist as a sufficiently high molecular weight after only one exposure.
  • it has excellent long-term heat resistance, weather resistance, solvent resistance and the like. Therefore, development and fixing operations for stabilizing the recorded image are not essential, and holograms can be produced in real time.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Holo Graphy (AREA)

Abstract

La présente invention concerne une composition destinée à des matériaux d'enregistrement holographique qui comprend un polymère liant (A) soluble dans des solvants organiques, un composé (B) polymérisable possédant une double liaison éthyléniquement insaturée, un initiateur (C) de photopolymérisation et un colorant (D) photosensibilisant. Ce matériau possède une excellente sensibilité, une excellente transparence et une excellente efficacité de diffraction, ces propriétés étant requises pour l'holographie. Cette composition de photopolymère pour holographie, qui est destinée à être utilisée dans un matériau d'enregistrement holographique en volume dans lequel la distribution de l'intensité concernant l'ombre et la lumière d'une configuration d'interférence lumineuse doit être enregistrée à partir des modifications d'indice de réfraction, comprend un polymère liant (A) soluble dans des solvants organiques, une double liaison, un initiateur (C) de polymérisation, un colorant photosensibilisant (d) et un supersensibilisant (E).
PCT/JP2003/003576 2002-03-27 2003-03-25 Composition de photopolymere destinee a un materiau d'enregistrement holographique, support d'enregistrement holographique et processus de production de celui-ci WO2003081344A1 (fr)

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WO2005101396A1 (fr) * 2004-04-16 2005-10-27 General Electric Company Materiaux de stockage optique pour enregistrement holographique, procedes de fabrication de ces materiaux, et procedes de stockage et de lecture de donnees
JP2005331771A (ja) * 2004-05-20 2005-12-02 Hitachi Chem Co Ltd 感光性樹脂組成物、これを用いた感光性エレメント、レジストパターンの形成方法及びプリント配線板の製造方法
JP2006113164A (ja) * 2004-10-13 2006-04-27 Daiso Co Ltd 高透明なホログラム記録材料組成物、ホログラム記録媒体、およびその製造方法
WO2006095610A1 (fr) * 2005-03-08 2006-09-14 Nippon Steel Chemical Co., Ltd. Composition de resine photosensible pour l'enregistrement d'un hologramme de phase de volume et support d'enregistrement d'informations optiques l'utilisant
WO2008096712A1 (fr) * 2007-02-05 2008-08-14 Nippon Steel Chemical Co., Ltd. Matériau d'enregistrement holographique à phase de volume et support d'enregistrement d'information optique
JP2009175304A (ja) * 2008-01-23 2009-08-06 Nippon Steel Chem Co Ltd 体積位相型ホログラム記録材料及びそれを用いた光情報記録媒体
JP2009271202A (ja) * 2008-05-01 2009-11-19 Hayashibara Biochem Lab Inc 体積型ホログラム記録用感光性組成物
US8034514B2 (en) 2005-03-08 2011-10-11 Nippon Steel Chemical Co., Ltd. Photosensitive resin composition for volume phase hologram recording and optical information recording medium using the same
CN102414616A (zh) * 2009-04-27 2012-04-11 日产化学工业株式会社 使用具有芴骨架的光聚合性聚合物的感光性组合物
US8535852B2 (en) 2010-05-20 2013-09-17 Tdk Corporation Hologram recording material and hologram recording medium
US20210222092A1 (en) * 2018-10-03 2021-07-22 Fujifilm Corporation Chemical liquid and chemical liquid storage body
US11427656B2 (en) * 2016-08-30 2022-08-30 Sony Corporation Photosensitive composition for hologram recording, hologram recording medium, and hologram

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WO2005101396A1 (fr) * 2004-04-16 2005-10-27 General Electric Company Materiaux de stockage optique pour enregistrement holographique, procedes de fabrication de ces materiaux, et procedes de stockage et de lecture de donnees
JP2005331771A (ja) * 2004-05-20 2005-12-02 Hitachi Chem Co Ltd 感光性樹脂組成物、これを用いた感光性エレメント、レジストパターンの形成方法及びプリント配線板の製造方法
JP4496845B2 (ja) * 2004-05-20 2010-07-07 日立化成工業株式会社 感光性樹脂組成物、これを用いた感光性エレメント、レジストパターンの形成方法及びプリント配線板の製造方法
JP2006113164A (ja) * 2004-10-13 2006-04-27 Daiso Co Ltd 高透明なホログラム記録材料組成物、ホログラム記録媒体、およびその製造方法
KR101024744B1 (ko) * 2005-03-08 2011-03-25 신닛테츠가가쿠 가부시키가이샤 체적 위상형 홀로그램 기록용 감광성 수지 조성물 및그것을 사용한 광정보기록매체
WO2006095610A1 (fr) * 2005-03-08 2006-09-14 Nippon Steel Chemical Co., Ltd. Composition de resine photosensible pour l'enregistrement d'un hologramme de phase de volume et support d'enregistrement d'informations optiques l'utilisant
US8034514B2 (en) 2005-03-08 2011-10-11 Nippon Steel Chemical Co., Ltd. Photosensitive resin composition for volume phase hologram recording and optical information recording medium using the same
JP4745333B2 (ja) * 2005-03-08 2011-08-10 新日鐵化学株式会社 体積位相型ホログラム記録用感光性樹脂組成物及びそれを用いた光情報記録媒体
WO2008096712A1 (fr) * 2007-02-05 2008-08-14 Nippon Steel Chemical Co., Ltd. Matériau d'enregistrement holographique à phase de volume et support d'enregistrement d'information optique
US8298726B2 (en) 2007-02-05 2012-10-30 Nippon Steel Chemical Co., Ltd. Volume phase hologram recording material and optical information recording medium
JP5130230B2 (ja) * 2007-02-05 2013-01-30 新日鉄住金化学株式会社 体積位相型ホログラム記録材料及び光情報記録媒体
KR101451265B1 (ko) 2007-02-05 2014-10-15 신닛테츠 수미킨 가가쿠 가부시키가이샤 체적 위상형 홀로그램 기록재료 및 광 정보 기록매체
JP2009175304A (ja) * 2008-01-23 2009-08-06 Nippon Steel Chem Co Ltd 体積位相型ホログラム記録材料及びそれを用いた光情報記録媒体
JP2009271202A (ja) * 2008-05-01 2009-11-19 Hayashibara Biochem Lab Inc 体積型ホログラム記録用感光性組成物
CN102414616A (zh) * 2009-04-27 2012-04-11 日产化学工业株式会社 使用具有芴骨架的光聚合性聚合物的感光性组合物
US8658342B2 (en) 2009-04-27 2014-02-25 Nissan Chemicals Industries, Ltd. Photosensitive composition including photopolymerizable polymer having fluorene skeleton
US8535852B2 (en) 2010-05-20 2013-09-17 Tdk Corporation Hologram recording material and hologram recording medium
US11427656B2 (en) * 2016-08-30 2022-08-30 Sony Corporation Photosensitive composition for hologram recording, hologram recording medium, and hologram
US20210222092A1 (en) * 2018-10-03 2021-07-22 Fujifilm Corporation Chemical liquid and chemical liquid storage body

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