WO2007125937A1 - Composition photoreactive, materiau optique, materiau d'enregistrement optique, materiau d'enregistrement d'un hologramme en relief, support d'enregistrement optique et procede d'enregistrement optique correspondant - Google Patents

Composition photoreactive, materiau optique, materiau d'enregistrement optique, materiau d'enregistrement d'un hologramme en relief, support d'enregistrement optique et procede d'enregistrement optique correspondant Download PDF

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WO2007125937A1
WO2007125937A1 PCT/JP2007/058910 JP2007058910W WO2007125937A1 WO 2007125937 A1 WO2007125937 A1 WO 2007125937A1 JP 2007058910 W JP2007058910 W JP 2007058910W WO 2007125937 A1 WO2007125937 A1 WO 2007125937A1
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Prior art keywords
sensitizer
reaction
reactive group
light
optical recording
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PCT/JP2007/058910
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English (en)
Japanese (ja)
Inventor
Makoto Takahashi
Yutaka Sasaki
Hideaki Ito
Jun Endo
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Mitsubishi Chemical Corporation
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Priority to JP2008513229A priority Critical patent/JPWO2007125937A1/ja
Publication of WO2007125937A1 publication Critical patent/WO2007125937A1/fr

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    • 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
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y10/00—Nanotechnology for information processing, storage or transmission, e.g. quantum computing or single electron logic
    • 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
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C1/00—Photosensitive materials
    • G03C1/72—Photosensitive compositions not covered by the groups G03C1/005 - G03C1/705
    • G03C1/73—Photosensitive compositions not covered by the groups G03C1/005 - G03C1/705 containing organic compounds
    • 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
    • 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
    • G11B2007/0003—Recording, reproducing or erasing systems characterised by the structure or type of the carrier
    • G11B2007/0009—Recording, reproducing or erasing systems characterised by the structure or type of the carrier for carriers having data stored in three dimensions, e.g. volume storage

Definitions

  • Photoreactive composition optical material, optical recording material, volume hologram recording material, optical recording medium, and optical recording method thereof
  • the present invention relates to a photoreactive composition, an optical material, an optical recording material, a volume hologram recording material, an optical recording medium, and an optical recording method thereof.
  • hologram recording has been actively studied because high-density recording, multiple recording, and the like are possible.
  • hologram recording there are known those using an amplitude hologram that utilizes a change in transmittance of a recording material, and those that use a phase hologram that uses a change in refractive index or irregularity of a recording material. .
  • a known volume phase hologram recording material generally uses a photopolymer method in which radical polymerization or cationic polymerization is combined with a sensitizer as a write-once method that does not require wet treatment or bleaching treatment.
  • the photopolymer method is a very simple method that can change the characteristics just by changing the monomer and the matrix to be combined.
  • Patent Document 3 a two-photon absorption optical material
  • Patent Document 1 a two-stage absorption optical material
  • Patent Document 1 Japanese Patent Application Laid-Open No. 2002-318433
  • Patent Document 2 Japanese Patent Application Laid-Open No. 2004-78224
  • Patent Document 3 Japanese Patent Laid-Open No. 2005-99416
  • Non-Patent Literature l The Journal of Physical Chemistry 1981, 85, 123. Disclosure of the Invention Problems to be solved by the invention
  • the present invention was devised in view of the above problems, and by providing a gate function, a photoreactive composition that enables reading of a record without destroying the recorded content when used for holographic recording.
  • An object is to provide an optical material, an optical recording material, a volume hologram recording material, an optical recording medium, and an optical recording method thereof.
  • the present inventor used a photoreactive composition having a sensitizer and a polymer having a reactive group as the material of the hologram recording medium, and Non-destructive readout function (that is, a function capable of reading a record without destroying the recorded content) by using a sensitizer having a reduced electron configuration with respect to the reactive group
  • Non-destructive readout function that is, a function capable of reading a record without destroying the recorded content
  • the gist of the present invention contains a sensitizer (A) excited by absorbing photons, and a polymer (B) having a reactive group (C) capable of causing chemical conversion,
  • the sensitizer (A) resides in a photoreactive composition characterized in that it has a reduced electron configuration with respect to the reactive group (C) (claim 1).
  • the sensitizer (A) is excited by absorbing two or more photons (claim 2).
  • the sensitizer (A) is preferably excited by absorbing photons of different wavelengths having a force of 2 or more (claim 3).
  • the sensitizer (A) is excited to a singlet excited state by absorbing the photons of the first excitation light, and then transitions to the lowest triplet excited state by intersystem crossing, Subsequently, by absorbing photons of the second excitation light having a wavelength different from that of the first excitation light, the multistage excitation type sensitization is excited to a triplet excited state higher than the lowest triplet excited state.
  • the body is preferred (claim 4).
  • the reaction is caused by the contribution of the excited sensitizer (A). It is preferred that the reactive group (c) undergoes chemical conversion to change the optical properties of the photoreactive composition (Claim 5).
  • the chemical conversion is an isomeric reaction (claim 6).
  • Another gist of the present invention resides in an optical material comprising the photoreactive composition (claim 7).
  • Still another subject matter of the present invention lies in an optical recording material characterized in that it also has the above-mentioned optical material force (claim 8).
  • Still another subject matter of the present invention lies in a volume holographic recording material characterized in that the optical recording material force is also provided (claim 9).
  • Still another subject matter of the present invention lies in an optical recording medium comprising a layer containing the optical recording material (claim 10).
  • Still another subject matter of the present invention lies in an optical recording method for an optical recording medium, wherein the excitation light is irradiated to the layer of the optical recording medium. ). At this time, it is preferable to irradiate reference light together with the excitation light, and record a hologram on the layer by interference between the excitation light and the reference light (claim 12).
  • a photoreactive composition capable of reading a record without destroying the recorded content
  • an optical material using the composition an optical recording material
  • an optical recording material an optical recording material
  • FIG. 1 is a diagram schematically showing how electrons move due to photon absorption.
  • FIG. 2 is a diagram schematically showing how electrons move due to photon absorption.
  • FIG. 3 is a diagram schematically showing how electrons move due to photon absorption.
  • FIG. 4 is a diagram showing an example of changes in the sensitizer and the reactive group at the time of reading when the sensitizer has an oxidized electron configuration with respect to the reactive group.
  • FIG. 5 (a) to FIG. 5 (c) show the sensitizer and reactive group at the time of readout when the sensitizer has an oxidized electron configuration with respect to the reactive group, respectively.
  • FIG. 6 is a diagram showing an example of changes in sensitizer (A) and reactive group (C) during readout in the photoreactive composition of the present invention.
  • FIG. 7 (a) to FIG. 7 (c) are examples of the electron arrangement of the sensitizer (A) and the reactive group (C) at the time of readout in the photoreactive composition of the present invention, respectively.
  • FIG. 7 (a) to FIG. 7 (c) are examples of the electron arrangement of the sensitizer (A) and the reactive group (C) at the time of readout in the photoreactive composition of the present invention, respectively.
  • FIG. 8 (a) to FIG. 8 (c) are sensitizers at the time of writing when the reactive group (C) is activated by reduction in the photoreactive composition of the present invention, respectively.
  • FIG. 4 is a diagram illustrating an example of an electron configuration of (A) and a reactive group (C).
  • FIGS. 9 (a) to 9 (c) are sensitizers at the time of writing when the reactive group (C) is activated by energy transfer in the photoreactive composition of the present invention, respectively. It is a figure showing an example of the electronic arrangement
  • FIG. 10 is a diagram schematically showing an outline of a measurement system used in Example 1 of the present invention.
  • the photoreactive composition of the present invention is a sensitizer that is excited by absorbing photons (hereinafter referred to as “excitation light”, which is light that can also excite the sensitizer (A) as appropriate).
  • excitation light which is light that can also excite the sensitizer (A) as appropriate.
  • A) and a polymer (B) are contained. Further, the polymer) has a reactive group (C) capable of causing chemical conversion.
  • the symbols “(A)”, “(B)”, and “(C)” that appear here are symbols for distinguishing sensitizers, polymers, and reactive groups.
  • the photoreactive composition of the present invention may contain other components as long as the effects of the present invention are not significantly impaired.
  • the sensitizer (A) has a reduced electron configuration with respect to the reactive group (C).
  • the sensitizer (A) can donate electrons to the reactive group (C).
  • the highest occupied orbit of the sensitizer (A) (Highest Occ upied Molecular Orbital (HOMO) is higher in energy than the highest occupied orbital of the reactive group (C)!
  • the sensitizer (A) is a substance (a whole compound or a part that exerts its sensitizing action) that is excited by absorbing photons upon irradiation with excitation light.
  • the sensitizer (A) when the sensitizer (A) is appropriately excited, electron or energy transfer occurs due to the contribution of the excited sensitizer (A), and the reactive group.
  • the chemical conversion of (C) is occurring.
  • the sensitizer (A) one having a reduced electron configuration with respect to the reactive group (C) is used.
  • the electron configuration of the sensitizer (A) and the reactive group (C) can be confirmed by measurement of acid reduction potential.
  • sensitizer (A) for example, a known sensitizer can be used.
  • sensitizer Means a molecule
  • sensitizer (A) means the whole or a part of a molecule.
  • compounds that can be used as the sensitizer (A) include synthetic dyes, natural pigments, aromatic compounds, and heterocyclic compounds.
  • synthetic dyes include atalidine dyes, azo dyes, alizarin dyes, anthraquinone dyes, indigoid dyes, carbo dyes, xanthene dyes, quinoline dyes, quinonimine dyes, diphenylmethane dyes, stilbene dyes, thiazoles.
  • synthetic dyes include atalidine dyes, azo dyes, alizarin dyes, anthraquinone dyes, indigoid dyes, carbo dyes, xanthene dyes, quinoline dyes, quinonimine dyes, diphenylmethane dyes, stilbene dyes, thiazoles.
  • examples include dyes, triphenyl methane dyes, nitro dyes, nitroso dyes, pyrazolone dyes, methine dyes, and sulfur dyes.
  • pigments include carotene, flavones, quinones, xanthones, petas-azine, blood pigments (such as porphyrins), chlorophyll, phenazine, phenoxane derivatives, and indole derivatives. .
  • aromatic compound examples include condensed aromatic rings, oligophenylenes, and conjugated genes.
  • heterocyclic compound examples include coumarin, azacoumarin, quinoline, azaquinoline, oxazonole, benzoxazonole, oxazionole, furan, benzofuran, pyrazoline, phthalimide, naphthalimide, pteridine, oligothiophene, heterocyclic salt And so on.
  • a dye such as cyanine, merocyanine, phthalocyanine, porphyrin, xanthene, triallylmethane, acylolidine, azine, chlorophyll.
  • benzophenone, oligothiophene, tetrazine, force rubazole, porphyrin, and the like are particularly preferable because they can function as a multistage excitation sensitizer (described later).
  • the portion exhibiting the sensitizing action of these exemplified compounds is used as the sensitizer (A).
  • the sensitizer (A) may be used alone or in combination of two or more in any combination and ratio.
  • the sensitizers (A) those which are excited by absorbing two or more photons (multiphoton absorption) (for example, a multiphoton absorbing compound or a portion thereof) are preferable.
  • the non-destructive readout function is realized by the combination of the sensitizer (A) and the reactive group (C) that affects the acid-reducibility. If the sensitizer (A) is excited by absorbing two or more photons (for example, a multiphoton absorbing compound or a portion thereof), the sensitizer (A) itself has a nondestructive readout function. This is because it can be realized more stably.
  • Multiphoton absorption refers to an orbital level that is sufficient to supply the reactant (in the present invention, reactive group (C)) with the energy necessary to initiate the reaction (chemical conversion). It is forcibly excited by absorbing a plurality of photons simultaneously or stepwise into the sensitizer.
  • Multiphoton absorption includes (a) one that absorbs light emitted from a single wavelength light source (see Figs. 1 and 2) and (b) one that absorbs light emitted from multiple light sources of different wavelengths ( (See Fig. 3)
  • Multiphoton absorption that absorbs light emitted from a single wavelength light source includes (i) a singlet excited state (S1) force that supplies energy to the reactive group (C), and (ii) a singlet excited state. From (S1) to the triplet excited state (T1) due to intersystem crossing, energy is transferred from there to the reactive group (C). Some supply one.
  • the minimum amount of photon energy required is the amount of energy ⁇ E from the ground state (SO) to the-singlet excited state (S 1).
  • Fig. 1 is a diagram schematically showing how electrons move due to photon absorption.
  • the ground state (SO) and the singlet excited state (S1) represent the existing energy states.
  • the virtual state (Sx) represents an energy state that is one photon higher than the ground state (SO). However, since the virtual state (Sx) is set temporarily and not in the existing energy state, electrons cannot move to the virtual state.
  • Absorption in the case of (i) is an absorption called simultaneous multiphoton absorption (in this example, simultaneous two-photon absorption).
  • simultaneous multiphoton absorption in this example, simultaneous two-photon absorption.
  • the sensitizer (A) when excitation is performed, the sensitizer (A) is irradiated with light (excitation light) and absorbs the two photons, thereby basing the sensitizer (A) on the base.
  • the electrons in the state (SO) move to the singlet excited state (S1).
  • the sensitizer (A) is excited and can react with the reactive group (C).
  • non-resonant two-photon absorption In this way, in simultaneous two-photon absorption, it is sufficient if the actual excited state exists at twice the energy level of the photon used for excitation, so there is no absorption in the absorption spectrum, and the region (non-resonant region) It is possible to excite molecules using light of a wavelength of.
  • the case where two-photon absorption occurs nonlinearly using light with a wavelength in the non-resonant region is called non-resonant two-photon absorption.
  • the efficiency of this non-resonant two-photon absorption is proportional to the square of the photoelectric field applied to the sensitizer (A) (the two-photon absorption squared characteristic). For this reason, in a three-dimensional space, two-photon absorption occurs only in a region where the applied light intensity is high, and no two-photon absorption occurs in a region where the light intensity is low. Therefore, non-resonant two-photon absorption is derived from this square characteristic in comparison with linear absorption where excitation occurs at all positions in proportion to the intensity of the applied photoelectric field. Since excitation occurs only in a predetermined region, the spatial resolution is significantly improved.
  • a laser having a wavelength longer than the wavelength region where linear absorption is performed that is, the wavelength region where one-photon absorption exists
  • a laser having no absorption Often uses light.
  • a laser in a transparent region that is, a laser that emits laser light in a wavelength region where there is no one-photon absorption
  • the laser light is subjected to absorption and scattering. Without reaching the inside of the photoreactive yarn and the product.
  • the two-photon absorption cross section indicating the two-photon absorption, but usually 100GM or more, preferably 1000GM or more, more preferably 10000GM.
  • a sensitizer (A) having the above is preferred.
  • the evaluation method of the two-photon absorption cross section is as follows. The evaluation of the two-photon absorption cross-section of a compound is performed with reference to the open-chamber type Z-scan method described in Reference I (IEEE J. Quant. Electron. 26 (1990) 760).
  • a Ti: sapphire laser and an optical parametric oscillator laser pumped by the laser are used as a light source for measuring the two-photon absorption cross section.
  • the pulse width of the light source pulse is 110 femtoseconds to 130 femtoseconds, the pulse repetition frequency is 76 Hz, and the average power is 10-1QQ mW.
  • the wavelength range is 570 ⁇ ! Measure at ⁇ 1200nm. As described in Document I, the measurement is performed by converging the pulse laser beam from the light source with a lens, scanning the sample to be measured in the direction of travel of the laser beam (Z axis), and Measure the transmittance at the sample position.
  • Figure 2 shows the movement of electrons associated with photon absorption. It is a figure which shows a mode typically.
  • the same reference numerals as those in FIG. 1 denote the same elements as in FIG.
  • the sensitizer (A) is irradiated with excitation light and absorbs two photons, so that electrons in the ground state (SO) move to the singlet excited state (SI). To do. However, in the case of (ii), the electrons in the singlet excited state (S1) move to the triplet excited state (T1) due to intersystem crossing. Thus, the sensitizer (A) is excited and can react with the reactive group (C).
  • any sensitizer (A) can be used as long as it is a compound having absorption and a portion thereof (a portion that exhibits a sensitizing action).
  • the energy is too low, and a large number of photons are required to supply the sensitizer (A) with energy necessary for excitation of the sensitizer (A). In particular, the efficiency can be significantly reduced.
  • sensitization suitable for multiphoton absorption that absorbs light emitted from a single wavelength light source for example, a compound having absorption in the visible region is preferably used.
  • dyes such as cyanine, merocyanine, phthalocyanine, ponolephyrin, xanthene, triarinolemethane, asylidine, azine, chlorophyll, aromatic compounds such as condensed aromatic rings, oligophenolene, conjugated gen, coumarin, azacoumarin, quinoline, azaquinoline.
  • heterocyclic compounds such as oxazole, benzoxazole, oxadiol, furan, benzofuran, pyrazoline, phthalimide, naphthalimide, pteridine, and heterocyclic salts.
  • a portion that exhibits the sensitizing action of these exemplified compounds can be used as a sensitizer (.
  • Multistage absorption is an example of multiphoton absorption that absorbs light emitted from a plurality of light sources having different wavelengths.
  • the sensitizer (A) changes from the ground state (SO) to the singlet excited state (S1) by absorbing the photons of the first light (first excitation light) emitted from the first light source.
  • the lowest triplet excited state (T1) By being excited and then transitioning to the lowest triplet excited state (T1) by intersystem crossing, followed by absorbing photons of the second light (second excitation light) emitted from the second light source
  • T1 the lowest triplet excited state
  • Tn triplet excited state
  • the triplet excited state (Tn) is an orbital level having sufficient energy for the initiation of the reaction, from this triplet excited state (Tn) to the reactive group (C) for the initiation of the reaction. Of energy is supplied.
  • FIG. 3 is a diagram schematically showing how electrons move due to photon absorption.
  • the same reference numerals as those in FIGS. 1 and 2 denote the same elements as those in FIGS.
  • This multistage absorption is an absorption called stepped multiphoton absorption (in this example, stepped two-photon absorption).
  • the sensitizer (A) was in the ground state (SO) of the sensitizer (A) by absorbing one photon of the first light. Electrons move to the singlet excited state (S1). After that, due to intersystem crossing, electrons existing in the singlet excited state (S1) move to the lowest triplet excited state (T1). [0042] Thereafter, the sensitizer (A) absorbs one photon of the second light. By absorbing this photon (second photon), electrons in the lowest triplet excited state (T1) of the sensitizer (A) become triplet excited states (Tn) at higher energy levels. Move to. As a result, the sensitizer ( ⁇ ) is excited and can react with the reactive group (C).
  • the wavelength of the first light causing the first stage excitation is shorter than the wavelength of the second light causing the second stage excitation (high energy). Is preferred.
  • the sensitizer ( ⁇ ) also excites the ground state (SO) force to the singlet excited state (S 1), it absorbs light of the second wavelength only weakly or not at all. Is preferred.
  • the orbital level of the singlet excited state (S1) in the first stage or Z and the lowest triplet excited state (T1) passing through the intersystem crossing from there is the reactive group (C) starting chemical conversion. It is preferable that the orbital level does not have enough energy to be able to start chemical conversion only after being excited to the triplet excited state (Tn) via the second stage excitation. . By selecting such a system, it is not possible to supply sufficient energy to the reactive group (C) with only one of the first light and the second light, and irradiation with light of both wavelengths. It is possible to add a so-called "light gate function" that can start chemical conversion of the reactive group (C) for the first time.
  • stepwise multiphoton absorption is caused by the addition of actual excitation.
  • the excitation wavelength of the first photon that is, the wavelength of the first light
  • the optical recording medium hologram recording medium formed from the photoreactive composition of the present invention is required for excitation after recording. Even if only one wavelength (that is, either the first light or the second light) of the two wavelengths of excitation light (that is, the first light or the second light) is irradiated, the sensitization is performed.
  • the body (A) is never excited.
  • Sensitizers (A) suitable for such stepwise multiphoton absorption include (1) singlet excited state (S (1) Long lifetime, (2) —low fluorescence in the singlet excited state (S 1), that is, good intersystem crossing efficiency, and (3) lowest triplet excited state (T1) Examples include compounds that have a long life span and satisfy at least one of them. It is more preferable that the above requirements are satisfied more. Specific examples of suitable sensitizers (A) that satisfy such requirements include ponorephrine, oligothiophene, xanthene, phthalocyanine, coumarin, oxazole, benzophenone, oligophenolene, and pyrene. In addition, a portion that exhibits the sensitizing action of the compounds shown in these examples can also be used as the sensitizer (A).
  • the quantum yield ( ⁇ ) in the triplet excited state is not particularly limited, but is preferably 0.5 or more, more preferably 0. . 7 or more
  • the triplet-triplet molar extinction coefficient ( ⁇ ) in the wavelength region of the excitation light of the second stage of the sensitizer (A) is not particularly limited, but is preferred.
  • each stage of excitation eg, first stage excitation, second stage excitation, etc.
  • each stage of excitation is independent of each other.
  • Multi-photon absorption that absorbs light emitted from a single wavelength it may occur by absorbing a plurality of photons of each wavelength.
  • a sensitizer (A) that is excited by multiphoton absorption for example, a multiphoton absorption compound or a portion thereof
  • optical recording is performed using the photoreactive composition of the present invention.
  • a medium is manufactured, recording and reproduction can be performed with excitation light having a relatively long wavelength with respect to the optical recording medium. For this reason, it is possible to record and replay using a long wavelength laser that is inexpensive and easily available without using a short wavelength laser that is generally expensive and difficult to obtain.
  • Advantages such as the ability to suppress side reactions that are likely to occur with ultraviolet light and recording with good recording quality can be obtained.
  • stepwise multiphoton absorption is preferable because an optical gate function can be realized. Therefore, as the sensitizer (A), among the multiphoton absorbing compound or a part thereof, a multistep excitation type multiphoton absorption compound (multistage excitation sensitizer) that generates stepwise multiphoton absorption or a part thereof is used. It is preferable to use the part as a sensitizer (A).
  • a multistep excitation type multiphoton absorption compound multistage excitation sensitizer
  • the sensitizer (A) when the sensitizer (A) absorbs two or more photons as described above, it is preferably excited by absorbing two or more different photons.
  • the type of photon wavelength means that the wavelengths are different from each other by 30 nm or more, preferably 50 nm or more.
  • the wavelength of the photon absorbed by the sensitizer (A) is two or more, stepwise multi-photon absorption is possible, and the photoreactive composition of the present invention has an advantage that a photogate function can be realized. be able to.
  • the use of the first excitation light and the second excitation light in the above-described stepwise two-photon absorption is an example of two or more photon wavelengths.
  • the content of the sensitizer (A) contained in the photoreactive composition of the present invention is arbitrary as long as the effects of the present invention are not significantly impaired. 0.001% by weight or more, preferably 0.01% by weight or more, more preferably 0.1% by weight or more, and usually 50% by weight or less, preferably 40% by weight or less, more preferably 30% by weight or less. . If the amount of the sensitizer (A) is too small, the sensitivity may decrease. If the amount is too large, absorption of light used for recording and reproduction increases, and light may not reach the depth direction.
  • the sensitizer (A) is a part of a compound (for example, a functional group)
  • the sensitizer (A) is included in the polymer) unless the effects of the present invention are impaired. Also good.
  • the sensitizer (A) is contained in the polymer (B)
  • the sensitizer (A) is heavy as a part of the main chain that may be contained in the polymer (B) as a side chain. It may be contained in coalescence (B).
  • Any polymer (B) may be used as long as it is a polymer (polymer) having a reactive group (C) capable of causing a predetermined chemical conversion.
  • the reactive group (C) will be described first, and then the polymer) will be described.
  • the reactive group (C) is a group of atoms that can substantially participate in chemical conversion, and causes chemical conversion. Any group can be used. There is no limitation on the chemical transformation in which the reactive group (C) is generated. Any appropriate chemical transformation can be used depending on the use of the photoreactive composition of the present invention. However, it is preferable that the reactive group (C) causes chemical conversion when the sensitizer (A) is appropriately excited. Therefore, it is preferable that the chemical transformation of the reactive group (C) occurs due to the contribution of the excited sensitizer (A).
  • organic reactions can be mentioned as examples of suitable ones. Among these, photoreaction, polymerization reaction, polymer reaction and the like are particularly preferable.
  • examples of the photoreaction include an isomerization reaction, a transfer reaction, a cyclization reaction, a dimerization reaction, a hydrogen abstraction reaction, and an addition reaction.
  • Examples of isomeric reactions include isomerization reactions of olefins, azo compounds, and carbonyl compounds.
  • isomerization reactions of olefins include cis-trans isomerization reactions (eg, cis-trans isomerism such as stilbene, 1,3 pentagen, cyclic olefin, olefins conjugated with carboleyl, and nitrogen compounds). Ii reaction). Further, the isomerization reaction of the azo compound includes a cis-trans isomerization reaction.
  • Examples of the rearrangement reaction include rearrangement reaction of olefin, polyene, and enone compounds, and photorearrangement reaction of carbo-louie compound.
  • rearrangement reactions of olefin and polyene include rearrangement reactions that occur during cyclization and isomerization reactions due to intramolecular rearrangement of protons, rearrangement reactions of di- ⁇ methane compounds (for example, 1,4 pentagen derivatives).
  • a rearrangement reaction that occurs during the formation of bulucyclopropane by the reaction a rearrangement reaction that occurs during the formation of cyclopropane by the photorearrangement of cyclic ⁇ -methane (for example, the rearrangement reaction of norbornagen-quadricicrane) Etc.)) and the like.
  • rearrangement reactions of enone compounds include rearrangement reactions that occur during 1,2-aryl and lumiketone rearrangements in ⁇ , ⁇ -cyclohexenone, photorearrangement reactions of cyclopentenone, ⁇ , Photorearrangement reaction of ⁇ -enone, rearrangement reaction of Genony compound (rearrangement reaction that occurs during the formation of bicyclohexenone or hydroxyketone from 2,5 cyclohexagenone; hetero 2,5 cyclohexagenone, 2, 4 -Rearrangement reaction that occurs during the rearrangement and ring cleavage reaction of cyclohexagenone; Rearrangement reaction that occurs during the photochemical reaction of trobolone (cycloheptatrienone).
  • the photorearrangement reaction of a carbo-Louis compound includes a photorearrangement reaction that occurs in the formation reaction of ketene and aldehyde by decomposition of a cyclic ketone, and a carbon monoxide elimination reaction from a carbonyl compound. Photorearrangement reaction that occurs during the reaction, and photorearrangement reaction that occurs during the formation reaction of the cyclic ether by ring expansion reaction of the cyclic ketone.
  • Examples of the cyclization reaction include a cyclization reaction of Gen and Trien, a photocyclization reaction of stilbene and a derivative thereof, and an intermolecular photocyclization reaction of olefin.
  • the cyclization reaction of gen and triene includes the cyclization reaction that occurs during the formation reaction of cyclobutane by the intramolecular cyclization reaction of non-conjugated gen, and the formation of cyclobutene by intramolecular cyclization of conjugated gen.
  • Examples include a cyclization reaction that occurs during the reaction, a cyclization reaction of cyclic conjugation, a ring formation reaction having triene by ring opening of bicyclohexagen, and a cyclization reaction of heterogene and triene.
  • photocyclization reaction of stilbene and its derivative includes photocyclization reaction that occurs in the synthesis reaction of phenanthrene, photocyclization reaction of azobenzene-aniline derivative, photocyclization of stilbene having anthrone and heterocycle And the like.
  • the intermolecular photocyclization reaction of olefins includes intermolecular photocyclization reaction between conjugated olefin and olefin, intermolecular photocyclization reaction that occurs in the photoaddition reaction to enony compound, and olefin to acetylene. And the intermolecular photocyclization reaction that occurs during the addition reaction of olefins to the aromatic ring.
  • dimerization reaction examples include the photodimerization reaction of olefin.
  • the photodimerization reaction of olefin is the dimer of alkylolefin.
  • divinylcyclobutane by the dimerization of cyclobutane by the dimerization of cyclobutane by the dimerization of cyclobutane the dimerization of cyclobutane by the dimerization of aromatic olefin
  • Photodimer reaction that occurs during the formation reaction photodimer reaction that occurs during the formation reaction of cyclobutane due to the dimerization of the enone compound (for example, the photodimer reaction of a chain enone compound; Photodimer reaction of tenone, cyclohexenone, heterocycle, etc .; photodimer reaction of quinone compounds), photodimer reaction of fumaric acid and maleic acid with their derivatives.
  • Examples of the hydrogen abstraction reaction include a hydrogen abstraction reaction of a carbonyl compound.
  • the hydrogen abstraction reaction of a carbonyl compound includes an intramolecular hydrogen abstraction reaction of an aromatic ketone, a hydrogen abstraction reaction that occurs during the formation reaction of cyclobutanol from a cycloalkyl ketone, and a cyclic ketone.
  • Abstraction reaction during bicycloalcohol formation reaction from ⁇ -diketones hydrogen abstraction reaction within ⁇ -diketone molecule, hydrogen bow I extraction reaction within ⁇ , ⁇ unsaturated ketone molecule, ortho-substituted aromatic ketone Examples include a hydrogen abstraction reaction that occurs during the cyclization and enantiomer reaction, a hydrogen abstraction reaction that occurs during the intramolecular cyclization reaction of phthalimide, and a hydrogen abstraction reaction that occurs during the reduction reaction of carbonyl.
  • Examples of the addition reaction include an addition reaction of a carbonyl compound to olefin.
  • the addition reaction of carbonyl compounds to olefins includes addition reactions that occur during the formation of oxetane by reaction with electron-rich olefins; carbonyl compounds and lack of electrons.
  • Addition reaction that occurs during the formation reaction of oxetane by reaction with olephine Addition reaction that occurs during the formation reaction of oxetane by intramolecular addition reaction of unsaturated ketone;
  • By addition reaction of ketone having electron withdrawing group to olefin Addition reactions that occur during the formation reaction of oxetane; addition reactions to olefins such as benzoquinone, fluoroketone, and nitrobenzene.
  • photoreactions of aromatic compounds include isomeric reactions of benzene and its derivatives, Isomerization reaction of gin and its derivatives, addition reaction to aromatic ring, synthesis reaction of substituted phenol and arlin by photofleece rearrangement, photosubstitution reaction of aromatic compound (nucleophilic reaction of nitroaromatic compound, And photo-substitution reaction of benzene and its analogues, photo-substitution reaction of poly-substituted benzene, photo-addition and substitution reaction to benzo-tolyl).
  • Examples of the polymerization reaction include addition polymerization reaction, transition metal catalyzed polymerization reaction, ring-opening polymerization reaction, cyclopolymerization reaction, polycondensation reaction, polyaddition / addition condensation reaction, and the like.
  • addition polymerization examples include radical polymerization reactions (for example, radical polymerization reactions of ethylene, vinyl chloride, butyl acetate, vinylidene chloride, styrene, butadiene, methacrylic monomers, acrylic monomers, acrylonitrile, etc.); cationic polymerization reactions (for example, cationic polymerization reaction such as styrene, isobutene, butyl ether, N-bulu force rubazole), ion polymerization reaction (eg, cation polymerization reaction such as styrene, butadiene, methacrylic monomer, acrylic monomer, nitroethylene) And ionic polymerization reactions.
  • radical polymerization reactions for example, radical polymerization reactions of ethylene, vinyl chloride, butyl acetate, vinylidene chloride, styrene, butadiene, methacrylic monomers, acrylic monomers, acrylonitrile, etc.
  • the transition metal catalyzed polymerization reaction includes, for example, a polymerization reaction using a Zeiggler-Natta catalyst (for example, a catalytic polymerization reaction of olefin, styrene, acetylene, gen, etc.), or a polymerization reaction using a metathesis catalyst. (For example, catalytic polymerization reaction of cyclic olefin, alkyne, gen, etc.).
  • a Zeiggler-Natta catalyst for example, a catalytic polymerization reaction of olefin, styrene, acetylene, gen, etc.
  • a metathesis catalyst for example, catalytic polymerization reaction of cyclic olefin, alkyne, gen, etc.
  • Examples of the ring-opening polymerization reaction include a ring-opening polymerization reaction of a cyclic monomer.
  • a crosslinking reaction for example, an epoxy-amine reaction, an epoxy mercaptan reaction, an unsaturated ester-amine reaction, an unsaturated ester-mercaptan reaction, a hydrocycle reaction, a urethanization reaction, etc.
  • dendrimer for example, an epoxy-amine reaction, an epoxy mercaptan reaction, an unsaturated ester-amine reaction, an unsaturated ester-mercaptan reaction, a hydrocycle reaction, a urethanization reaction, etc.
  • isomerization reaction and rearrangement reaction are preferred.
  • a reactive group (C) that generates an isomerization reaction or a rearrangement reaction it is possible to obtain the advantage that it is not dependent on the surrounding environment where the free volume is small.
  • the chemical conversion it is also preferable to use one that changes the optical properties of the photoreactive composition of the present invention by the chemical conversion. That is, the sensitizer (A) is excited In such a case, it is preferable to employ a compound in which the reactive group (C) is chemically converted by the contribution of the excited sensitizer (A) and the optical properties of the photoreactive composition of the present invention are changed. ,.
  • the optical characteristics that change include refractive index and Abbe number (reverse dispersion ratio). Among them, refractive index is preferable.
  • the photoreactive composition of the present invention can be suitably used as a hologram recording material.
  • Examples of chemical transformations that can change the optical properties of the photoreactive composition as described above include addition reactions, isomerization reactions, rearrangement reactions, cyclization reactions, and the like. Of these, isomerization reaction, rearrangement reaction, and cyclization reaction are preferable in order to greatly change the refractive index.
  • Particular preferred isomerization reactions include cis-trans isomerization reactions, and among them, more preferable reactions include cis-trans isomerization reactions of azo compounds.
  • rearrangement reactions include intramolecular rearrangement reactions of olefin and polyene.
  • a more preferable reaction is a rearrangement reaction from norbornagen to quadricyclane.
  • particularly suitable cyclization reactions include intermolecular photocyclization reactions, and among them, more preferred reactions include intermolecular photocyclization reactions of anthracene.
  • the refractive index changes as a change in optical characteristics
  • there is no limit to the degree to which the refractive index changes but usually 0.001 or more, preferably 0.01 or more, more preferably 0.05 or more. Chemical transformations that cause this change are preferred. This is because the greater the change in refractive index, the higher the multiplicity of recording and the larger the recording capacity per unit volume.
  • Specific examples of the reactive group (C) that causes chemical conversion as described above include a norbornagen group.
  • porphyrin as the sensitizer (A) and norbornagen group as the reactive group (C).
  • the reactive group (C) one kind may be used alone. Two or more kinds may be used in any combination and in any ratio. Accordingly, the polymer) may have two or more kinds of reactive groups (C).
  • the molecular weight of the reactive group (C) is not limited.
  • the polymer) is a polymer having a reactive group (C).
  • the reactive group (C) may be contained in the polymer (B) as a part of the main chain which may be contained in the polymer (B) as a side chain. Further, it may contain a reactive group (C) that is not contained in the polymer.
  • the polymer (B) may be a polymer obtained by polymerizing only one kind of monomer, or may be a copolymer obtained by copolymerizing two or more kinds of monomers in an arbitrary combination and ratio. ! / Further, there is no limitation on the type of polymerization, and a polymer obtained by any type of polymerization method such as block polymerization, random polymerization, graft polymerization or the like can be used. Furthermore, the polymer) may be linear or branched.
  • suitable polymers (B) include polymetatalylate, polyacrylate, polystyrene, polyester, polyamide, polyurethane, polycarbonate, polyetherol, cenorelose esterol, poly (polyacrylate) having a reactive group (C). Vininoles Estenore, Polyvinylenoatenore, Polysiloxane, Polyolefin derivatives and the like.
  • the polymer (B) may be used alone or in combination of two or more in any combination and ratio.
  • the viewpoint of improving the sensitivity upon photoexcitation is that the polymer is optically transparent in the spectral region (that is, in the wavelength region) absorbed by the sensitizer (A).
  • the polymer preferably has no significant absorption at the wavelength of excitation light (excitation wavelength).
  • the haze of the polymer (B) at a thickness of 1 mm is usually 30% or less, preferably 10% or less, more preferably 5% or less.
  • the haze is preferably as small as possible, and the lower limit is 0%.
  • the polymer (B) is preferably one that does not interfere with the chemical conversion of the reactive group (C). That is, the reactive group (C) is converted into a component other than the reactive group (C) in the molecular structure of the polymer (B). It is preferable that the academic conversion is not disturbed.
  • the polymer (B) may have a substituent other than the reactive group (C) as long as the effects of the present invention are not significantly impaired.
  • the substituent may be used alone or in combination of two or more in any combination and ratio.
  • the weight average molecular weight of the polymer (B) is not limited, and any force as long as the effect of the present invention is not significantly impaired. Usually 1000 or more, preferably 3000 or more, more preferably 5000 or more, and further Preferably it is 10,000 or more. There is no particular upper limit. If the molecular weight is too small, the archive life may be shortened.
  • the weight average molecular weight of the polymer (B) can be measured by GPC (gel permeation chromatography).
  • the viewpoint power to increase the archive life when the photoreactive composition of the present invention is used as an optical recording material or a volume hologram recording material is that the micro-Brownian motion of the polymer (B) is in use. It is preferable to make it smaller. To achieve this, the polymer (B)
  • the glass transition temperature Tg of (B) is suitably 20 ° C or higher, preferably 30 ° C or higher, more preferably 50 ° C or higher, and usually 300 ° C or lower, preferably 290 ° C or lower. More preferably, it is 280 ° C or lower.
  • the content of the polymer (B) contained in the photoreactive composition of the present invention is arbitrary as long as the effects of the present invention are not significantly impaired.
  • the polymer (B) can be produced by bonding the reactive group (C) to an arbitrary polymer (polymer before bonding the reactive group (C)).
  • the reaction performed during the synthesis include urethanization, esterification, etherification, sulfidation, carboxylic acid epoxy reaction, amine-epoxy reaction, thiol epoxy reaction, amidation reaction, acid anhydride-amine reaction, and the like.
  • the photoreactive composition of the present invention may contain other components (additives).
  • an arbitrary additive may be used for the purpose of controlling the excitation of the sensitizer (A) (controlling the excitation wavelength and excitation energy), controlling the reaction, and improving the characteristics. Absent.
  • a sensitization aid is used as an additive for controlling excitation of the sensitizer (A).
  • the additive for controlling the reaction include an initiator, a chain transfer agent, a polymerization terminator, a compatibilizing agent, and a reaction auxiliary agent.
  • additives for improving the properties include dispersants, antifoaming agents, plasticizers, preservatives, stabilizers and the like.
  • the amount of the additive used is arbitrary as long as the effects of the present invention are not significantly impaired.
  • the concentration in the photoreactive composition of the present invention is usually 0.001% by weight or more, preferably 0.01% by weight or more, and usually 30% by weight or less, preferably 10% by weight or less.
  • the sensitizer (A) since the sensitizer (A) has a reduced electron configuration with respect to the reactive group (C), it is used for an optical recording medium such as a hologram recording medium. In addition, it is possible to read the record without destroying the recorded content. The reason why such an excellent advantage can be obtained is assumed as follows.
  • FIG. 4 shows an example of changes in the sensitizer and the reactive group at the time of readout when the sensitizer has an oxidized electron configuration with respect to the reactive group!
  • FIGS. 5 (a) to 5 (c) show the sensitizer and reactive group at the time of readout when the sensitizer has an oxidized electron configuration with respect to the reactive group. It is a figure showing an example of electronic arrangement
  • FIG. 6 is a diagram showing an example of changes in the sensitizer (A) and the reactive group (C) during readout in the photoreactive composition of the present invention.
  • FIG. 7 (a) to FIG. 7 (c) show the electron configuration of the sensitizer (A) and the reactive group (C) at the time of readout, respectively, in the photoreactive composition of the present invention. It is a figure showing an example.
  • a composition having a sensitizer such as sensitizer (A)
  • a substance having a reactive group such as reactive group (C)
  • a volume hologram recording medium is formed using
  • the volume hologram recording medium is irradiated with reading light (reproduction light).
  • the sensitizer When the readout light is irradiated, the sensitizer is excited (see stepl in Fig. 4). At this time, the electrons in the occupied orbit AO of the sensitizer move to an intermediate empty orbit Ax according to the intensity of the readout light (see Fig. 5 (a)). As a result, an occupant orbit AO of the sensitizer becomes empty, and electrons enter. (See Fig. 5 (b)).
  • the sensitizer has an oxidized electron configuration with respect to the reactive group, so the occupied orbital AO of the sensitizer has an energy level higher than the occupied orbital CO of the reactive group. Low. For this reason, electrons move from the occupied orbit CO of the reactive group to the occupied orbit AO of the sensitizer in which the vacancy is generated, as indicated by the solid line arrow in FIG. 5 (b). This electron transfer oxidizes the reactive group (see step 2 in Fig. 4). As shown in Fig. 5 (c), the oxidized reactive group becomes an excited state in which only one electron is present in the occupied orbital CO, and thus becomes an active state that can cause chemical mutation.
  • Reactive groups that have become active may cause chemical transformations. If the reactive group undergoes chemical conversion, the recorded content may be destroyed. In other words, the chemical conversion is a force that occurs when information is written. When this chemical conversion occurs when information is read, the program of the recording section changes and the recorded contents are destroyed.
  • A1 and C1 indicate the vacant orbitals of the sensitizer and the reactive group, respectively.
  • a volume hologram recording medium is formed using the photoreactive composition of the present invention. That is, at the time of reading information, when the reading light is irradiated to the volume hologram recording medium, the sensitizer (A) is excited (see stepl in FIG. 6). At this time, electrons in the occupied orbit AO of the sensitizer (A) move to an intermediate air path Ax corresponding to the intensity of the readout light (see Fig. 7 (a)). As a result, a space is generated in the occupied orbit AO of the sensitizer (A) and electrons can enter (see Fig. 7 (b)).
  • the sensitizer (A) has a reduced electron configuration with respect to the reactive group (C).
  • Occupied orbital AO has a higher energy level than the occupied orbital CO of the reactive group (C). For this reason, electrons do not move from the occupied orbit CO of the reactive group (C) to the occupied orbit AO of the sensitizer (A) in which the vacant space is generated.
  • the intermediate empty orbit AX is made lower than the empty orbit C1 of the reactive group (C) by keeping the energy of the readout light within an appropriate range, etc.
  • the sensitizer (A) If the electron in the occupied track AO is not given too much energy), the electron may not move from the intermediate track Ax to the empty track C 1 of the reactive group (C). (See dashed arrow in Figure 7 (b)). Therefore, the electrons that have moved to the intermediate empty orbit Ax move to the occupied orbit AO of the sensitizer (A) as shown by the solid line arrow in FIG. 7 (b). In this way, the sensitizer (A) relaxes and returns to the state before excitation (see Fig. 7 (c)), and the reactive group (C) is not oxidized. ) Remains inactive (see step 2 in Figure 6). Therefore, the recorded content is not destroyed without the reactive group (C) causing a chemical transformation.
  • A1 represents an empty orbit of the sensitizer (A).
  • the photoreactive composition of the present invention can read a record without destroying the recorded content.
  • the reactive group (C) undergoes chemical transformation when irradiated with appropriate excitation light. That is, in the photoreactive composition of the present invention, chemical reaction can be caused to the reactive group (C) by using light of a certain predetermined condition, and the reactive group (C) is not exposed to light of other conditions. If no chemical conversion occurs! /, It is possible to realize the function (ie, optical gate function). Specifically, the energy force that the irradiated light gives to the sensitizer (A) Chemical conversion occurs depending on whether the intermediate empty orbit Ax is higher or lower than the empty orbit C1 of the reactive group (C). It is possible to control whether or not.
  • the photoreactive composition of the present invention when used for hologram recording, excites the sensitizer (A) and contributes to the reactive group (C) by the contribution of the excited sensitizer (A). It is possible to write information by converting the data.
  • the mechanism is explained below with an example.
  • FIG. 8 (a) to FIG. 8 (c) show the sensitizer (A) and reaction at the time of writing when the reactive group (C) is activated by reduction in the photoreactive composition of the present invention, respectively.
  • AO and A1 represent the occupant and empty orbital electron configurations of the sensitizer (A), respectively
  • CO and C1 represent the groups of the reactive group (C).
  • the energy of the photon is used to move electrons in the occupied orbit AO of the sensitizer (A) to the empty orbit A1 (Fig. 8 (a ) Arrow).
  • the electrons in the occupied orbit AO of the sensitizer (A) move to the empty orbit A1 as shown in FIG. 8 (b).
  • the reactive group (C) has electrons in the vacant orbit C1, and becomes active. Therefore, the reactive group (C) that has become active thereafter undergoes chemical transformation. Therefore, if information is written using this chemical conversion, a volume hologram recording medium can be formed using the photoreactive composition of the present invention. That is, in this volume hologram recording medium, information can be written when the sensitizer (A) absorbs photons.
  • FIG. 9 (a) to FIG. 9 (c) show the sensitizer (A) and reaction during writing when the reactive group (C) is activated by energy transfer in the photoreactive composition of the present invention, respectively. It is a figure showing an example of the electronic arrangement of group (C).
  • AO and A 1 represent the occupant and empty orbital electron configurations of the sensitizer (A), respectively
  • CO and C1 represent the reactive group (C). Represents the electronic configuration of the occupied orbit and empty orbit, respectively.
  • the photoreactive composition of the present invention when writing information, is irradiated with recording light, and the sensitizer (A) absorbs photons of this recording light.
  • the energy of the photon is the same as that explained in the example of reduction using Fig. 8 (a) above, as shown in Fig. 9 (a), the electrons in the occupied orbit AO of the sensitizer (A). Is used to move to orbit A1 (see arrow in Fig. 9 (a)).
  • the electrons in the occupied orbit AO of the sensitizer (A) move to the empty orbit A1 as shown in FIG. 9 (b).
  • a space is generated in the occupied track AO of the sensitizer (A).
  • a volume hologram recording medium that can be used can be formed. That is, this volume hologram recording medium can also write information by the photosensitizer absorbing the photons.
  • the photoreactive composition of the present invention it is possible to lengthen the one-life eve life when a volume hologram recording medium is used. Specifically, how much archive life can be obtained is not uniform depending on the composition of the photoreactive composition, the usage environment of the volume hologram recording medium, and the like.
  • the information written on the volume hologram recording medium using the photoreactive composition of the present invention is usually at least 3 years, preferably at least 10 years, more preferably at least 30 years at room temperature (25 ° C). Have an archive life of.
  • the photoreactive composition of the present invention can be used as a material in any industrial field. Of these, use as an optical material is preferable because the characteristics of the photoreactive composition of the present invention can be effectively utilized.
  • the photoreactive composition of the present invention When the photoreactive composition of the present invention is used as an optical material, the photoreactive composition of the present invention alone can coexist with other components that can be used as an optical material, together with the photoreactive composition, It may be used as an optical material. There are no restrictions on the other components. For example, it is possible to use a light dispersing agent, a coloring material, or the like. The amount of other components used is also arbitrary.
  • optical material is arbitrary, but it is particularly preferable to use it as an optical recording material.
  • the optical recording material is preferably used as a volume hologram recording material. This makes it possible to effectively utilize the advantages of the photoreactive composition of the present invention described above.
  • the optical recording medium of the present invention is formed by using the photoreactive composition of the present invention as an optical recording medium or a volume hologram recording material. As long as it is configured to include the photoreactive composition of the present invention as the material for recording information, the specific configuration is not limited and is arbitrary.
  • the optical recording medium of the present embodiment includes a recording layer formed of an optical recording material.
  • the optical recording material is a material containing at least the photoreactive composition of the present invention.
  • the optical recording medium is configured to include a support and other layers as necessary.
  • the recording layer is a layer on which information is recorded. Information is usually recorded as a hologram.
  • the recording layer contains the photoreactive composition of the present invention. It is made of an optical recording material.
  • the optical recording material may be formed of the photoreactive composition of the present invention alone, but may contain other components as required. Further, how much other components are contained is arbitrary as long as the effects of the present invention are not significantly impaired.
  • the thickness of the recording layer is not limited. Usually, the thickness of the recording layer varies depending on the recording method. However, in the optical recording medium, the thickness of the recording layer is usually 1 ⁇ m or more, preferably 10 ⁇ m or more, and usually 1 cm or less, preferably 2000 ⁇ m or less. If the recording layer is too thick, the selectivity of each hologram may be lowered during multiplex recording on an optical recording medium, and the degree of multiplex recording may be reduced. If the recording layer is too thin, it is difficult to form the entire recording layer uniformly, and it is difficult to perform multiplex recording with a uniform diffraction efficiency of each hologram and a high SZN ratio.
  • the optical recording medium has a support, and the recording layer and other layers are laminated on the support to constitute the optical recording medium.
  • the support is usually required to have the necessary strength and durability. Although there is no restriction
  • the material constituting the support is not limited and may be transparent or opaque.
  • transparent materials include organic materials such as acrylic, polyethylene terephthalate film, polyethylene naphthoate, polycarbonate, polyethylene, polystyrene, and cellulose acetate; and inorganic materials such as glass, silicon, and quartz.
  • organic materials such as acrylic, polyethylene terephthalate film, polyethylene naphthoate, polycarbonate, polyethylene, polystyrene, and cellulose acetate
  • inorganic materials such as glass, silicon, and quartz.
  • polycarbonate, acrylic, polyester, glass and the like are preferable, and acrylic, polycarbonate, and glass are more preferable.
  • an opaque material is cited as the support material, a metal such as aluminum; a metal such as gold, silver, or aluminum on the transparent support, or magnesium fluoride, zirconium oxide, etc. And those coated with a dielectric material.
  • the thickness of the support is not limited. However, usually 0. lmn! It is preferably ⁇ lmm. If the support is too thin, the mechanical strength of the optical recording medium may be insufficient, and if it is too thick, the cost may increase.
  • the surface of the support may be subjected to a surface treatment.
  • This surface treatment is usually performed to improve the adhesion between the support and the recording layer.
  • Examples of surface treatment include corona discharge treatment and forming a layer for surface treatment.
  • examples of the layer for the surface treatment include a layer formed from a halogen phenol or a partially hydrolyzed vinyl chloride-vinyl acetate copolymer (such as an undercoating layer and an undercoat layer). .
  • the surface treatment may be performed for purposes other than the improvement of adhesiveness.
  • examples include a reflective coating process that forms a reflective coating layer made of a metal such as gold, silver, or aluminum; a dielectric coating process that forms a dielectric layer such as magnesium fluoride or zirconium oxide. Is mentioned. These layers may be formed as a single layer or two or more layers.
  • the support may be provided only on one or both of the upper and lower sides of the recording layer of the optical recording medium of the present invention. However, in the case where supports are provided on both the upper and lower sides of the recording layer, at least one of the supports is transparent so as to transmit active energy rays (excitation light, reference light, reproduction light, etc.).
  • a transmissive or reflective hologram can be recorded.
  • a reflection hologram can be recorded.
  • the support may be provided with a pattern for data address.
  • the patterning method is not limited.
  • the support itself may be formed with irregularities, or a pattern may be formed on a reflective layer (described later), or a combination of these methods may be used.
  • it is not necessary to have a support as long as the support layer is not essential and the recording layer and other layers have the required strength and durability.
  • a protective layer In addition to the recording layer and the support described above, other layers may be provided on the optical recording medium.
  • the protective layer is a layer for preventing adverse effects such as a decrease in sensitivity due to oxygen and deterioration in storage stability.
  • a protective layer can be formed of a layer having a water-soluble polymer and the like.
  • the reflective layer is formed when the optical recording medium is configured in a reflective type.
  • the reflective layer may be formed between the support and the recording layer, or may be formed on the outer surface of the support. It is preferable to be between the layers.
  • an antireflection film may be provided on the side where the recording light and the reading light enter and exit, or between the recording layer and the support. .
  • the antireflection film functions to improve the light utilization efficiency and suppress the generation of ghost images.
  • it can be produced by coating the photoreactive composition of the present invention on a support without solvent and forming a recording layer.
  • any coating method can be used. Specific examples include spray method, spin coating method, wire bar method, dip method, air knife coating method, roll coating method, blade coating method, doctor roll coating method and the like.
  • the recording layer in particular, when forming a thick recording layer, it is also possible to use a method of placing in a mold and molding, or a method of coating on a release film and punching the mold.
  • the photoreactive composition of the present invention and a solvent or additive may be mixed to prepare a coating solution, which may be coated on a support and dried to form a recording layer. good.
  • a coating solution which may be coated on a support and dried to form a recording layer. good.
  • any coating method can be used.
  • the same method as described above can be used. Can be adopted.
  • the solvent it is usually preferable to use a solvent that has sufficient solubility for the components used, gives good coating properties, and does not attack a support such as a resin substrate. ,.
  • solvents examples include ketone solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, and methyl amyl ketone; aromatic solvents such as toluene and xylene; methanol, ethanol, propanol Alcohol solvents such as n-butanol, heptanol, hexanol, diacetone alcohol, furfuryl alcohol; ketone alcohol solvents such as diacetone alcohol, 3 -hydroxy- 3 -methyl-2-butanone; tetrahydrofuran, dioxane, etc.
  • ketone solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, and methyl amyl ketone
  • aromatic solvents such as toluene and xylene
  • methanol, ethanol, propanol Alcohol solvents such as n
  • Ether solvents Halogen solvents such as dichloromethane, dichloroethane, chloroform, etc .
  • Cellosolve solvents such as methyl solvosolve, ethinorecero soleb, butinorecellosolve, methyl cecrosolve acetate, ethilce solvate acetate
  • Propylene such as polyethylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monobutyl ether, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monobutyl ether acetate, dipropylene glycol dimethyl ether
  • Glycol solvents Ethyl acetate, butyl acetate, amyl acetate, butyl acetate, ethylenic glycol diacetate, jetyloxalate, ethyl pyruvate, ethyl
  • the solvent one kind may be used alone, and two kinds or more may be used in optional combination and ratio. Moreover, there is no restriction
  • the photoreactive composition of the present invention is thermoplastic
  • the photoreactive composition of the present invention is molded by, for example, an injection molding method, a sheet molding method, a hot press method, etc.
  • the recording layer is produced by molding the photoreactive composition of the present invention by, for example, a reaction injection molding method or a liquid injection molding method. can do.
  • the molded body has sufficient thickness, rigidity, strength, etc., the molded body can be used as it is as an optical recording medium.
  • a method for producing an optical recording medium for example, a method of producing a recording layer by applying a photoreactive composition melted by heat onto a support, and cooling and solidifying the composition, A method in which a photoreactive composition is applied to a support and cured by thermal polymerization to form a recording layer, and a liquid photoreactive composition is applied to a support and cured by photopolymerization. And a method of manufacturing the recording layer by forming the recording layer.
  • the optical recording medium manufactured in this way can take the form of a self-supporting slab or a disk, and can be used for a three-dimensional image display device, a diffractive optical element, a large-capacity memory, and the like.
  • Both writing (recording) and reading (reproduction) of information with respect to the optical recording medium are performed by light irradiation.
  • the recording layer is irradiated with excitation light from the sensitizer (A), that is, light corresponding to the excitation wavelength of the sensitizer (A), as a recording light. Convert (C) to record information.
  • the reproducing light is irradiated onto the recording layer, and the transmitted light is read if it is a transmissive optical recording medium, and the reflected light is read if it is a reflective optical recording medium. , Play back information.
  • the recording layer is irradiated with reference light together with recording light (also called object light). If the recording light and the reference light are caused to interfere with each other in the recording layer, the interference fringes are recorded as chemical conversion of the reactive group (C) in the recording layer.
  • the reactive group (C) In other words, when the photoreactive composition of the present invention causes a change in refractive index, interference fringes are recorded as a difference in refractive index in the recording layer.
  • a hologram is recorded on the recording layer by the interference fringes recorded in the recording layer.
  • the recording light is used as the first and second lights.
  • the reference light may be used as the first and second light, or one of the recording light and the reference light may be used as the first light and the other as the second light.
  • the recording layer is irradiated with predetermined reproduction light (usually reference light).
  • the irradiated reproduction light is diffracted according to the interference fringes. Since this diffracted light contains the same information as that of the recording layer, it is possible to reproduce the information recorded on the recording layer by reading the diffracted light.
  • the reference light and the reproduction light have wavelengths and intensities that do not cause excitation of the sensitizer (A) and the reactive group (C) by themselves.
  • non-destructive reading at the time of reproduction which has been difficult to realize in the past, becomes possible, and an optical recording medium having an optical gate function can be obtained.
  • the wavelength range of the recording light, the reproduction light, and the reference light is arbitrary depending on each application, and may be in the infrared region, visible light region, or ultraviolet region.
  • solid lasers such as ruby, glass, Nd—YAG (neodymium yttrium aluminum garnet), Nd—YV04 (neodymium yttrium vanadium tetraoxide); Diode lasers such as GaAs and InGaAs; gas lasers such as helium neon, argon, krypton, excimer, and CO;
  • Lasers that are excellent in monochromaticity and directivity, such as one-on-one may be a pulse laser or a continuous wave laser! / ⁇
  • the recording light, the reproducing light, and the reference light are V, and the deviation is not limited to the irradiation amount, so long as it can be recorded and reproduced.
  • the recording light, the reproduction light and the reference light are usually 0.1 to 20 JZC m 2 according to the composition of the recording layer forming composition, the type of polymerization initiator of the reactive group (C), and the blending amount. Irradiate in the range of.
  • Mn represents a number average molecular weight
  • Mw represents a weight average molecular weight
  • a polymer (B) having a reactive group (C) was synthesized by an operation corresponding to the description on page 2 of “Photoresponsive Polymers, 1764, 2001”.
  • Sensitizer (A) uses 5, 10, 15, 20-tetra [3,5 bis (trifluoromethyl) phenol]-21H, 23H porphyrin platinum (II), and polymer (B Using NBD-PS synthesized in Synthesis Example 1 as above, a sample was produced as an optical recording medium as follows.
  • NBD-PS (1. Og) synthesized in Synthesis Example 1 and 5, 10, 15, 20-tetra [3,5 bis (trifluoromethyl) phenol] 21H, 23H-porphyrin platinum (II) (50 mg) was used as a tetrahydrofuran solution, cast on a glass substrate, and dried to form a 200 / zm thick film as a sample.
  • the specific method of casting is as follows. It was cast on a slide glass substrate and left to stand in the dark at room temperature for 12 hours to dry. After that, it was dried by heating in an oven at 80 ° C for 2 hours. After drying by heating, place a Teflon (registered trademark) film with a thickness of 50 m on both sides of the slide glass as a spacer and heat it in an oven at 80 ° C for 1 hour by fixing it with another glass slide with a cover and a clip. Thus, a smooth recording medium (sample) having a thickness of 50 m was obtained.
  • the casting method was the same as in Example 1.
  • the casting method was the same as in Example 1.
  • sensitizer (A) 2, 2 ,: 5, 2 "-Terthiophene-5-Carboxaldehyde (2, 2,: 5, 2" -Terthiophene-5-carboxaldehyde) (manufactured by Tokyo Chemical Industry Co., Ltd.) is used.
  • the casting method was the same as in Example 1.
  • the casting method was the same as in Example 1.
  • the casting method was the same as in Example 1.
  • sensitizer (A) 2, 2,: 5,2 "-terthiophene (2, 2,: 5,2" -Terthiophene) (manufactured by Wako Pure Chemical Industries, Ltd.) is used, and a polymer ( As B), polysilane (trade name: Ogsol SI-10-10, manufactured by Osaka Gas Co., Ltd.) was used to prepare a sample as an optical recording medium as follows.
  • a film with a thickness of 50 m was formed by casting and drying on top, and used as a sample.
  • the casting method was the same as in Example 1.
  • FIG. 10 is a diagram schematically showing an outline of the measurement system used in this example.
  • the light source for hologram recording is a diode that excites the Nd—YV04 crystal with a diode, and uses a non-linear optical crystal LiB 2 O (also referred to as “LBO”) to obtain 532 nm light.
  • LiB 2 O also referred to as “LBO”
  • Verdi—V2 Verdi—V2
  • Laser2 a diode laser capable of obtaining light of 405 nm
  • Laser2 a diode laser capable of obtaining light of 405 nm
  • the bisector of the angle formed by the two beams is perpendicular to the recording surface, and the vibration planes of the electric field vectors of the two beams obtained by the division are two intersecting lines. It was made to be parallel to the plane containing the beam.
  • the hologram was recorded on the recording layer of the sample [Sample] by the interference of the light [L1, L2] from Laserl and Laser2.
  • the 405 nm light [L2] is blocked, and one of the two 532 nm lights [L1] obtained by the division is blocked, and recording is performed at the same angle as during recording.
  • the diffracted light irradiated on the surface was recorded using a power meter (not shown) and a detector (Newport 2930-C, 918-SL) [PD1, PD2].
  • the diffraction efficiency of a hologram is given by the ratio of the diffracted light intensity to the incident light intensity.
  • Table 1 below shows the results of measuring the sample prepared by the above preparation method using the above measurement method.
  • the beam irradiation intensity during recording is L Recording was performed with the aserl beam intensity set to lWcm- 2 and the Laser2 set to 80mWcm- 2 .
  • the irradiation time of Laserl and Laser2 was 3000 seconds in Example 1, 500 / second in Example 2, and 200 / second in Examples 3-7!
  • the recording state does not change even if the sample after recording is exposed to 532 nm light [L1]. In the absence of 405 nm gate light [L2], It became apparent that no recording occurred and no light was exposed to the readout light. This confirmed that non-destructive reading is possible.
  • the Tl level of the sensitizer ( ⁇ ) 2, 2 ': 5, 2 "-terthiophene has sufficient energy to chemically change the reactive group of the polymer NBD PS.
  • the energy for starting the reaction is supplied to the reactive group only after reaching the Tn level.
  • the present invention can be used in any industrial field, but is particularly suitable for use in an optical recording medium such as a hologram recording medium.

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  • General Physics & Mathematics (AREA)
  • Mathematical Physics (AREA)
  • Theoretical Computer Science (AREA)
  • Crystallography & Structural Chemistry (AREA)
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  • Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
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Abstract

La présente invention concerne une composition photoréactive qui, lorsqu'elle est utilisée au cours d'un enregistrement d'hologramme, peut lire l'enregistrement sans réduire la capacité d'un enregistrement résiduel. La composition photoréactive comprend un sensibilisateur (A), excité lors de l'absorption d'un photon, et un polymère (B) contenant un groupe réactif chimiquement convertible (C). Dans le cas présent, le sensibilisateur (A) prend une configuration électronique réduite par rapport au groupe réactif (C).
PCT/JP2007/058910 2006-04-28 2007-04-25 Composition photoreactive, materiau optique, materiau d'enregistrement optique, materiau d'enregistrement d'un hologramme en relief, support d'enregistrement optique et procede d'enregistrement optique correspondant WO2007125937A1 (fr)

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JP2011054266A (ja) * 2009-08-31 2011-03-17 General Electric Co <Ge> 組成物、光学データ記憶媒体及び光学データ記憶媒体の使用方法
WO2011102545A1 (fr) * 2010-02-18 2011-08-25 Fujifilm Corporation Matériau d'enregistrement d'absorption biphotonique non résonant et composé d'absorption biphotonique non résonant
JP2012022317A (ja) * 2010-07-16 2012-02-02 Lg Chem Ltd 光反応性重合体およびこの製造方法
JP2012053974A (ja) * 2010-08-31 2012-03-15 General Electric Co <Ge> 光データ記憶媒体における付加色素の使用

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JP2011053676A (ja) * 2009-08-31 2011-03-17 General Electric Co <Ge> 組成物、光データ記憶媒体及び光データ記憶媒体の使用方法
JP2011054266A (ja) * 2009-08-31 2011-03-17 General Electric Co <Ge> 組成物、光学データ記憶媒体及び光学データ記憶媒体の使用方法
WO2011102545A1 (fr) * 2010-02-18 2011-08-25 Fujifilm Corporation Matériau d'enregistrement d'absorption biphotonique non résonant et composé d'absorption biphotonique non résonant
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JP2012053974A (ja) * 2010-08-31 2012-03-15 General Electric Co <Ge> 光データ記憶媒体における付加色素の使用

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