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WO2019117538A1 - Composé colorant et composition photopolymère - Google Patents

Composé colorant et composition photopolymère Download PDF

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Publication number
WO2019117538A1
WO2019117538A1 PCT/KR2018/015464 KR2018015464W WO2019117538A1 WO 2019117538 A1 WO2019117538 A1 WO 2019117538A1 KR 2018015464 W KR2018015464 W KR 2018015464W WO 2019117538 A1 WO2019117538 A1 WO 2019117538A1
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WIPO (PCT)
Prior art keywords
group
substituted
carbon atoms
unsubstituted
compound
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
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PCT/KR2018/015464
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English (en)
Korean (ko)
Inventor
김헌
김유식
카르바쉬라이사
권세현
장영래
장석훈
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
LG Chem Ltd
Korea Advanced Institute of Science and Technology KAIST
Original Assignee
LG Chem Ltd
Korea Advanced Institute of Science and Technology KAIST
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Priority claimed from KR1020180156151A external-priority patent/KR102157366B1/ko
Application filed by LG Chem Ltd, Korea Advanced Institute of Science and Technology KAIST filed Critical LG Chem Ltd
Priority to CN201880057141.3A priority Critical patent/CN111406097B/zh
Priority to JP2020518727A priority patent/JP7012975B2/ja
Priority to US16/651,906 priority patent/US11084933B2/en
Publication of WO2019117538A1 publication Critical patent/WO2019117538A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B57/00—Other synthetic dyes of known constitution
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
    • G03F7/033—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
    • G03F7/035—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polyurethanes
    • 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
    • G11B7/08—Disposition or mounting of heads or light sources relatively to record carriers

Definitions

  • the present invention relates to a dye compound, a photopolymer composition, a hologram recording medium, an optical element and a holographic recording method.
  • the holographic medium 010 records information by changing the refractive index in the holographic recording layer in the medium through the exposure process, and reads the change in refractive index in the recorded medium to reproduce the information.
  • the optical interference pattern can be easily stored in the hologram by photopolymerization of the low-molecular monomer, so that the optical lens, mirror, deflection mirror, filter, diffusing screen,
  • a holographic optical element having functions of a light guide, a waveguide, a projection screen and / or a mask, a medium of an optical memory system and a light diffusion plate, an optical wavelength splitter, a reflection type, and a transmission type color filter.
  • the photopolymer composition for hologram production comprises a polymeric binder, a monomer, and a photoinitiator, and irradiates the photosensitive film produced from such a composition with laser interference light to induce photopolymerization of the local monomer.
  • the refractive index increases at a portion where a relatively large amount of monomer exists, and at a portion where a polymer binder is relatively present, a refractive index is relatively lowered to cause a refractive index modulation, and such a refractive index modulation generates a diffraction grating.
  • the refractive index modulation value II is influenced by the thickness of the photopolymer layer and diffraction efficiency (), and the angular selectivity becomes wider as the thickness becomes thinner.
  • the present invention is to provide a novel structure compound.
  • the present invention is to provide a hologram recording medium which has a thin thickness, a large refractive index modulation value of 10, and improved durability against temperature and humidity.
  • the present invention is to provide an optical element including a hologram recording medium.
  • the present invention also provides a holographic recording method comprising the step of selectively polymerizing a photoreactive monomer contained in the hologram recording medium 15 by a coherent laser.
  • a compound of novel structure is provided. Such a compound can be used as a dye.
  • photopolymer compositions comprising the compounds of the novel structure.
  • a hologram recording medium manufactured from the photopolymer composition is provided.
  • an optical 25 element including the hologram recording medium is provided.
  • Also disclosed herein is a holographic recording method comprising selectively polymerizing a photoreactive monomer contained in the photopolymer composition by an incoherent light source.
  • (meth) acrylate means methacrylate or acrylate.
  • the (co) polymer refers to a homopolymer or copolymer (including random copolymers, block copolymers, and graft copolymers).
  • a hologram means a recording medium in which optical information is recorded in an entire visible range and near-ultraviolet range (300 to 800 nm) through an exposure process, and for example, an in- ) Holograms, of-axes holograms, previous full-aperture holograms, white light transmissive holograms ("rainbow holograms"), deni syuk holograms, biaxial reflective holograms, edge- And includes all of the visual holograms such as an edge-l iterature hologram or a holographic stereogram.
  • the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the alkyl group has 1 to 10 carbon atoms. According to another embodiment, the alkyl group has 1 to 6 carbon atoms.
  • alkyl group examples include a methyl group, an ethyl group, a propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a tert-butyl group, 2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, heptyl, n-hexyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylbutyl, But are not limited to, dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylnucyl and 5-methylnucyl.
  • the alkylene group is a divalent functional group derived from an alkane, for example, a linear, branched or cyclic alkylene group, an ethylene group, a propylene group, an isobutylene group, a sec- Butylenes, tert-butylenes, pentenes, nuclear silicones, and the like. 2019/117538 1 »(: 1 ⁇ ⁇ 2018/015464
  • a compound of formula 1 may be provided. [Chemical Formula 1]
  • XI and Q are the same or different and each is an alkyl group having 1 to 20 carbon atoms and hydrogen; A halogen group; A nitrile group; A substituted or unsubstituted C1-C20 alkoxy group; A substituted or unsubstituted aryloxy group having 6 to 20 carbon atoms; Or a substituted or unsubstituted C6-C20 aryl group,
  • 3 ⁇ 4, 3 ⁇ 4 , 3 ⁇ 4 and 3 ⁇ 4 are the same or different and each represents hydrogen or an alkyl group having 1 to 2 carbon atoms; A halogen group; A nitrile group; A substituted or unsubstituted C1-C20 alkoxy group; A substituted or unsubstituted aryloxy group having 6 to 20 carbon atoms; Or a substituted or unsubstituted C6-C20 aryl group,
  • the above-mentioned groups may form a substituted or unsubstituted alicyclic ring having 4 to 2 carbon atoms or a substituted or unsubstituted aromatic ring having 6 to 20 carbon atoms,
  • 3 ⁇ 4 and 3 ⁇ 4 may form a substituted or unsubstituted alicyclic ring having 4 to 20 carbon atoms or a substituted or unsubstituted aromatic ring having 6 to 20 carbon atoms,
  • the show is an aromatic bifunctional vessel of 6 to 30 carbon atoms
  • the above-mentioned 9 is a functional group containing a carboxyl group ( ⁇ ), an ether group (-0-), or an ester (- (: 00-).
  • the present inventors have newly synthesized the compound of the above formula (1).
  • the compound of the formula (1) has high fluorescence efficiency, excellent light fastness or can realize an improved luminance and color reproduction rate, And it is possible to realize high refractive index modulation in the present invention.
  • the compound of Formula 1 may be used as a dye in a photopolymer composition providing a hologram recording medium.
  • the description of each functional group is as described above. More specific examples of the functional group of the above formula (1)
  • XI and Q are hydrogen, an alkyl group having 1 to 20 carbon atoms; A halogen group; Or a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms,
  • carboxyl group (- 00010; An alkylcarbamoyl group having 1 to 20 carbon atoms; A cycloalkylcarboxylate group having 4 to 20 carbon atoms; An aryl carboxylate group having 6 to 20 carbon atoms,
  • 3 ⁇ 4 and 3 ⁇ 4 may form a substituted or unsubstituted alicyclic monocyclic or polycyclic ring having 4 to 20 carbon atoms or a substituted or unsubstituted aromatic monocyclic or polycyclic ring having 6 to 20 carbon atoms,
  • the show is an aromatic bifunctional vessel of 6 to 20 carbon atoms
  • More specific examples of the compound of the formula (1) include compounds of the following formulas (3) to (5) or mixtures thereof.
  • 3 ⁇ 4 2 is an alkenyl group each is hydrogen, an alkyl group having 1 to 10 straight or branched-chain, or straight-chain or branched-chain having 2 within 20,
  • X I and Q are a halogen group; Or a substituted or unsubstituted C1-C20 alkoxy group,
  • the above-mentioned 3 is an aromatic ring having 6 to 20 carbon atoms in which one or more halogen groups are substituted.
  • a polymer matrix or precursor thereof; A dye comprising the compound of Formula 1; Photoreactive monomers; And a photoinitiator may be provided.
  • the inventors of the present invention newly synthesized the compound of the formula (1).
  • the compound of the formula (1) is used as a dye in a photopolymer composition providing a hologram recording medium, a high refractive index modulation value and a high refractive index
  • the experimental results show that the diffraction efficiency can be realized and the invention is completed.
  • a method of increasing the refractive index modulation value and the diffraction efficiency or changing the polymer matrix or the recording monomer to be used, or using specific additives is known.
  • the compound can improve the refractive index modulation value and the diffraction efficiency more easily even by applying a very high usage amount.
  • the content of the compound of formula (1) is as described above.
  • the polymer matrix or its precursor can serve as a support for the hologram recording medium and the final product made therefrom, and the photoreactive monomer can serve as a recording monomer.
  • the photoreactive monomer may be selectively polymerized on the polymer matrix to cause refractive index modulation due to a portion having a different refractive index.
  • the polymer matrix or its precursor is a compound that can be commonly used in a photopolymer composition providing a hologram recording medium and can be used without any limitations. 2019/117538 1 »(: 1 ⁇ ⁇ 2018/015464
  • the polymer matrix or precursor thereof include 1) a reaction product between a compound containing at least one isocyanate group and a polyol; Or (2) a polymer matrix comprising a (meth) acrylate-based (co) polymer in which the silane-based functional group is located in the branch chain and a silane crosslinking agent.
  • a hologram formed from a polymer matrix comprising a (co) polymer and a silane crosslinker, or a photopolymer composition comprising the precursor thereof, has significantly improved refractive index modulation values and superior temperature and humidity durability It can be implemented.
  • silane crosslinking agent and the silane-based functional group are located in the branch chain
  • the cross-linking density of the coating film or the hologram is optimized from the above-mentioned photopolymer composition to excellent durability against temperature and humidity .
  • the recording property can be improved by maximizing the refractive index modulation by increasing the fluidity (1) between the photoreactive monomer having a high refractive index and the component having a low refractive index.
  • a crosslinked structure mediated by a siloxane bond can be easily introduced through a sol-gel reaction between a modified (meth) acrylate-based (co) polymer containing a silane-based functional group and a silane crosslinking agent containing a terminal silane- ,
  • Such siloxane bonds can provide excellent durability against temperature and humidity.
  • the (meth) acrylate-based (co) polymer and the silane crosslinking agent in which the above-mentioned silane-based functional group is located on the branch chain in the polymer matrix may be present as separate components, and also exist in the form of a complex can do.
  • the silane-based functional group may be located in the branch chain.
  • the silane-based functional group may include a silane functional group or an alkoxysilane functional group, preferably an alkoxysilane functional group A trimethoxysilane group can be used.
  • the silane-based functional group may form a siloxane bond through a sol-gel reaction with the silane-based functional group contained in the silane crosslinking agent to crosslink the (meth) acrylate-based (co) polymer and the silane crosslinking agent.
  • the silane crosslinking agent may be a compound having an average of at least one silane-based functional group per molecule or a mixture thereof, and may be a compound containing at least one silane-based functional group.
  • the silane-based functional group may include a silane functional group or an alkoxysilane functional group, and preferably a triethoxysilane group may be used as an alkoxysilane functional group.
  • the silane-based functional group may form a siloxane bond through a sol-gel reaction with the silane-based functional group contained in the (meth) acrylate-based (co) polymer to crosslink the (meth) acrylate-based (co) polymer and the silane crosslinking agent .
  • the silane crosslinking agent may have an equivalence of the silane-based functional groups of 200 g / g to 1000 g / g. Accordingly, the cross-linking density between the (meth) acrylate-based (co) polymer and the silane cross-linking agent is optimized, and excellent durability against temperature and humidity can be secured compared to the existing matrix. In addition, through the above-mentioned cross-link density optimization, the recording property can be improved by maximizing the refractive index modulation by increasing the mobility between the photoreactive monomer having a high refractive index and the low refractive index component.
  • the equivalence of the silane-based functional groups contained in the silane crosslinking agent is excessively increased to 1000 g / mol or more, the diffraction grating interface after recording may be broken due to the reduction of the crosslinking density of the matrix, and the loose crosslinking density and the glass transition temperature
  • the monomer and plasticizer components can be eluted to the surface to generate haze. If the equivalent of the silane-based functional group contained in the silane crosslinking agent is excessively decreased to less than 200 g / g, crosslinking density becomes too high, which hinders the flowability of the monomer and the plasticizer components, .
  • the silane crosslinking agent may include a linear polyether backbone having a weight average molecular weight of 100 to 2000, or 300 to 1000, or 300 to 700, and a silane-based functional group bound to the terminal or branch chain of the main chain.
  • the linear polyether backbone having a weight average molecular weight of 100 to 2000 may include a repeating unit represented by the following formula (3).
  • 3 ⁇ 4 is an alkylene group having 1 to 10 carbon atoms, II is an integer of 1 or more, or 1 to 50, or 5 to 20, or 8 to 10.
  • the silane crosslinking agent can introduce a flexible polyether polyol as a main chain to improve the fluidity of the components by controlling the glass transition temperature and crosslinking density of the matrix.
  • the bond between the silane functional group and the polyether backbone may be mediated by a urethane bond.
  • the silane-based functional group and the polyether main chain may form a mutual bond through a urethane bond.
  • the silicon atom contained in the silane-based functional group may be bonded directly to the nitrogen atom of the urethane bond or an alkylene group having 1 to 10 carbon atoms Group, and the 1 < 2 > functional group contained in the polyether backbone can be directly bonded to the oxygen atom of the urethane bond.
  • silane crosslinking agent is a reaction between an isocyanate compound containing a silane functional group and a linear polyether polyol compound having a weight average molecular weight of 100 to 2000 ≪ / RTI >
  • the isocyanate compound is an aliphatic, cycloaliphatic, aromatic or aromatic aliphatic mono-isocyanate di-isocyanate, tri-isocyanate or poly-isocyanate; Or oligo- isocyanates of diisocyanates or triisocyanates having urethane, urea, carbodiimide, acyl urea, isocyanurate, allophanate, biuret, oxadiazinetrione, uretdione or iminooxadiazine dione structure Or poly-isocyanate.
  • isocyanate compound containing the silane functional group examples include 3-isocyanatopropyltriethoxysilane.
  • the polyether polyol includes, for example, styrene oxide, ethylene oxide, propylene oxide, tetrahydrofuran, butylene oxide, Polyether polyols and polyhydric alcohols obtained by condensation of polyaddition products of epichlorohydrin with their mixed adducts and graft products, and polyhydric alcohols or mixtures thereof, obtained by alkoxylation of amines and amino alcohols admit.
  • polyether polyol examples include OH functionalities of 1.5 to 6 and
  • silane crosslinking agent when the silane functional group and the polyether main chain are bonded via a urethane bond, a silane crosslinking agent can be more easily synthesized.
  • the weight average molecular weight (GPC measurement) of the silane crosslinking agent may be 1000 to 5,000,000.
  • the weight average molecular weight means the weight average molecular weight (unit: g / mol) in terms of polystyrene measured by GPC method.
  • a detector such as a known analyzer and a refractive index detector may be used, and a column for analysis may be used.
  • Temperature conditions, solvent, and f low rate Specific examples of the measurement conditions include a temperature of 30 ° C, a chloroform solvent (Chloroform), and an f low rate of 1 mL / min.
  • the (meth) acrylate-based (co) polymer may include a (meth) acrylate repeating unit and a (meth) acrylate repeating unit in which the silane functional group is located in the branch chain.
  • Examples of the (meth) acrylate repeating unit in which the silane functional group is located in the branch chain include repeating units represented by the following formula (1).
  • each of 3 ⁇ 4 to 3 ⁇ 4 is independently an alkyl group having 1 to 10 carbon atoms
  • 3 ⁇ 4 is hydrogen or an alkyl group having 1 to 10 carbon atoms
  • 3 ⁇ 4 is an alkylene group having 1 to 10 carbon atoms.
  • each of 3 ⁇ 4 to 3 ⁇ 4 is independently a number of carbon atoms
  • 1 is a methyl group
  • 3 ⁇ 4 is a methyl group having a carbon number of 1
  • 3 ⁇ 4 is a propylene group having a carbon number of 3
  • Derived from the repeating unit, or to 3 ⁇ 4 3 ⁇ 4 are each independently a methyl group having a carbon number of 1
  • 3 ⁇ 4 is hydrogen, 3 ⁇ 4 propylene group having a carbon number of 3, 3-Shows>, 10 ⁇ 71) 1 Ke 11: 1 61:] 10 7 It may be a recurring unit derived from the nucleotide sequence 16 (SEQ ID NO: 5103).
  • Examples of the (meth) acrylate repeating unit include repeating units represented by the following formula (2).
  • 3 ⁇ 4 is an alkyl group having 1 to 20 carbon atoms
  • 3 ⁇ 4 is hydrogen or an alkyl group having 1 to 10 carbon atoms, preferably 3 and 4 in the formula (2) Acrylate-derived repeating unit.
  • the molar ratio of the repeating unit of Formula 2 to the repeating unit of Formula 1 may be 0.5: 1 to 14: 1. If the molar ratio of repeating units of formula (1) is excessively decreased, the cross-linking density of the matrix becomes too low to serve as a support, resulting in a decrease in recording characteristics after recording, , The crosslinking density of the matrix becomes too high and the fluidity of the respective components may be deteriorated, resulting in a decrease in the refractive index modulation value.
  • the weight average molecular weight (GPC measurement) of the (meth) acrylate-based (co) polymer may be 100,000 to 5,000,000, or 300,000 to 900,000.
  • the weight average molecular weight means the weight average molecular weight (unit: g / mol) in terms of polystyrene measured by GPC method.
  • a detector such as a known analyzer and a refractive index detector may be used, and a column for analysis may be used.
  • Temperature conditions, solvent, and f low rate Specific examples of the measurement conditions include a temperature of 30 ° C., a chloroform solvent (Chloroform), and an f low rate of 1 mL / min.
  • the (meth) acrylate-based (co) polymer may have an equivalent weight of the silane-based functional groups of 300 g / g to 2000 g / g, or 500 g / g to 2000 g / / Dog, or from 580 g / dog to 1600 g / dog, or from 586 g / dog to 1562 g / dog.
  • the equivalent weight means the average molecular weight between the silane functional groups. The smaller the equivalent value, the higher the functional group density. The larger the equivalent value, the smaller the functional group density.
  • the cross-linking density between the (meth) acrylate-based (co) polymer and the silane cross-linking agent is optimized, thereby ensuring excellent durability against temperature and humidity compared to the existing matrix.
  • the recording property can be improved by maximizing the refractive index modulation by increasing the fluidity (mobility) between the photoreactive monomer having a high refractive index and the component having a low refractive index.
  • the (meth) acrylate-based (co) polymer preferably has a If the equivalent weight is excessively reduced to less than 300 g / g, the cross-linking density of the matrix becomes too high to inhibit the flowability of the components, thereby causing a decrease in the recording property. If the equivalent of the silane-based functional group contained in the (meth) acrylate-based (co) polymer is excessively increased to more than 2000 g / mol, the crosslinking density becomes too low to serve as a support, The refractive index modulation value can be reduced over time as the interface of the diffraction gratings collapses.
  • the silane crosslinking agent may be used in an amount of 10 to 90 parts by weight, 20 to 70 parts by weight, or 22 to 65 parts by weight based on 100 parts by weight of the (meth) acrylate-based (co) polymer. have.
  • the silane crosslinking agent content is excessively decreased with respect to 100 parts by weight of the (meth) acrylate-based (co) polymer, the curing rate of the matrix is significantly slowed to lose its function as a support, (100) parts by weight of the (meth) acrylate-based (co) polymer in the reaction product, if the content of the silane crosslinking agent is excessively increased, the curing rate of the matrix is accelerated but the reactive silane group content Excessive increase causes compatibility problems with other components and haze occurs.
  • the modulus (storage elastic modulus) of the reaction product may be 0.01 MPa to 5 MPa.
  • the modulus measuring method As a specific example of the modulus measuring method,
  • a storage modulus CG 'value at a frequency of 1 Hz at room temperature (20 ° C to 25 ° C) can be determined using a DHR (di scover hybr idometer) instrument.
  • the glass transition temperature of the reaction product may be -40 ° C to 10 ° C.
  • phase angle (loss modulus) change of the film coated with the photopolymerizable composition in the range of -80 ° C to 30 ° C under the setting condition of 5 ° C / min. 2019/117538 1 »(: 1 ⁇ ⁇ 2018/015464
  • polymer matrix or its precursor is a polymer matrix comprising the reaction product of a compound containing at least one isocyanate group and a polyol.
  • the compound containing at least one isocyanate group may be a known compound having at least one? 0 functional group per molecule or a mixture thereof, and may be a compound containing at least one isocyanate group.
  • the compound containing at least one isocyanate group is an aliphatic, cycloaliphatic , aromatic or aromatic aliphatic mono-di- , tri- or poly-isocyanate.
  • the compound containing at least one isocyanate group may be a monomer having a urethane, urea, carbodiimide, acyl urea, isocyanurate, allophanate, biuret, oxadiazinetrione, uretdione, (Oligo- and polyisocyanates) of relatively high molecular weight of di- and / or triisocyanates.
  • the compound containing at least one isocyanate group include at least one compound selected from the group consisting of butylene diisocyanate, hexamethylene methylene diisocyanate (1), isophorone diisocyanate (1), 1,8-diisocyanato-4- Anethitomethyl) octane,
  • the polyol which reacts with the compound containing at least one isocyanate group to form a polymer matrix may be an aliphatic, aromatic aliphatic or cycloaliphatic diol, triol and / or higher polyol having 2 to 20 carbon atoms.
  • the polyol can have a 300 ⁇ ⁇ 0 1 to about 10, 000 ⁇ ⁇ 0 the 1 hydroxy group equivalent of 100, 000 to 1, 500, a weight average molecular weight of 0000 ⁇ ⁇ 0 1. 2019/117538 1 »(: 1 ⁇ ⁇ 2018/015464
  • diols examples include ethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, dipropylene glycol, tripropylene glycol, 1,2-propanediol, 1,3-propanediol, 1,4-butanediol, neopentyl Glycols, 2-ethyl-2-butylpropanediol, trimethylpentanediol, diethyloctanediol positional isomers, 1,3-butylene glycol, a cyclic nucleic acid diol, 1,4-cyclohexanedimethanol, 2, 2-dimethyl-3-hydroxypropyl, 2,2-bis (4-hydroxycyclohexyl) propane, Dimethyl-3-hydroxypropionate.
  • triols examples include trimethylolethane, trimethylolpropane or glycerol.
  • Suitable highly-functional alcohols are ditrimethylolpropane, pentaerythritol, dipentaerythritol or sorbitol.
  • the polyols also include aliphatic and cycloaliphatic polyols of relatively high molecular weight such as polyester polyols, polyether polyols, polycarbonate polyols, hydroxy-functional acrylic resins, hydroxy-functional polyurethane, hydroxy- Functional epoxy resins and the like can be used.
  • the polyester polyol may be, for example, ethanediol, di-, tri- or tetraethylene glycol, 1,2-propanediol, di-, tri- or tetrapropyleneglycol, 1,3-propanediol, 1,3-butanediol, 2,3-butanediol, 1,5-pentanediol, 1,6-nucleic acid diol, 2,2-dimethyl-1,3-propanediol, 1,4-dihydroxycyclo- Polyhydric alcohols such as 1,4-dimethylolcyclohexyl acid, 1,8-octanediol, 1,10-decanediol, 1,12-dodecanediol or mixtures thereof, and optionally with trimethylolpropane or glycerol It is also possible to use higher functional polyols at the same time, for example, in the presence of a catalyst such as succ
  • polyhydric alcohol for production.
  • free polycarboxylic acids it is also possible to use the corresponding polycarboxylic anhydrides of the lower alcohols or the corresponding polycarboxylates, or mixtures thereof, in the preparation of the polyesters.
  • Polyester polyols that can be used in the synthesis of the polymer matrix also include mono- or copolymers of lactones, which are preferably lactones such as butyrolactone, caprolactone and / or methyl-caprolactone, or mixtures of lactones
  • lactones which are preferably lactones such as butyrolactone, caprolactone and / or methyl-caprolactone, or mixtures of lactones
  • a suitable bifunctional and / or higher functional initiator molecule such as the abovementioned small molecular weight polyhydric alcohols, as a synthetic component for polyester polyols, for example.
  • the polycarbonate having a hydroxyl group is also suitable as a polyhydroxy component for prepolymer synthesis, for example, a diol such as 1,4-butanediol and / or 1,6-nucleic acid diol and / or 3-methyl
  • a diol such as 1,4-butanediol and / or 1,6-nucleic acid diol and / or 3-methyl
  • diaryl carbonates such as diphenyl carbonate, dimethyl carbonate or phosgene.
  • the polyether polyol which can be used for the synthesis of the polymer matrix may be, for example, a polyaddition product of styrene oxide, ethylene oxide, propylene oxide, tetrahydrofuran, butylene oxide and epichlorohydrin, Amides and aminoalcohols obtained by condensation of polyhydric alcohols, mixed adducts and graft products, and polyhydric alcohols or mixtures thereof, and the like.
  • the polyether polyol include a functionality of 011 of 1.5 to 6 and a viscosity of 200 to 18000 A between the number average molecular weight, preferably from 1.8 to 4.0 011 the functionality and 600 to 8000 can be of g / mol for the average molecular weight, and particularly preferably 1.9 to 3.1 uiye the functionality and 650 to 4500 ⁇ / mole number average molecular weight of the (Propylene oxide), poly (ethylene oxide) and combinations thereof, or poly (tetrahydrofuran) and mixtures thereof in the form of a random or block copolymer.
  • the photoreactive monomer may include a polyfunctional (meth) acrylate monomer or a monofunctional (meth) acrylate monomer.
  • the refractive index increases at the portion where the polymer is relatively polymerized and the refractive index is relatively low at the portion where the polymer binder is relatively present, thereby causing the refractive index modulation, and the refractive index modulation generates the diffraction grating.
  • examples of the photoreactive monomer include (meth) acrylate type a, p-unsaturated carboxylic acid derivatives such as (meth) acrylate,
  • the photoreactive monomer is a polyfunctional (meth) acrylate monomer having a refractive index of 1.5 or more, or 1.53 or more, or 1.5 to 1.7, and the refractive index is 1.5 or more, or 1.53 or more, or 1.5 to 1.7.
  • the functional (meth) acrylate monomers may include halogen atoms (bromine, iodine, etc.), sulfur (S), phosphorus (P), or aromatic rings.
  • polyfunctional (meth) acrylate monomer having a refractive index of 1.5 or more include bi sphenol A modi fi ed diacrylate series, fuorene acrylate series (HR 6022, etc.), bi sphenol fuorene epoxy acrylate series , HR6060, HR6042, etc. - Miwonj), and halogenated epoxy acrylate series (HR1139, HR3362, etc. - Miwonjfct).
  • the photoreactive monomer is a monofunctional (meth) acrylate monomer.
  • the monofunctional (meth) acrylate monomer may include an ether bond and a fluorene functional group in the molecule.
  • Specific examples of the monofunctional (meth) acrylate monomer include phenoxybenzyl
  • the photoreactive monomer may have a weight average molecular weight of 50 g / mol to 1000 g / mol, or 200 g / mol to 600 g / mol.
  • the weight average molecular weight means the weight average molecular weight in terms of polystyrene measured by GPC method.
  • the hologram recording medium of the embodiment may further include a photoinitiator.
  • the photoinitiator is a compound which is activated by light or actinic radiation and initiates polymerization of a compound containing a photoreactive functional group such as the photoreactive monomer.
  • conventionally known photoinitiators may be used without any limitation, and specific examples thereof include a photo radical polymerization initiator, a photo cationic polymerization initiator, and a photoanion polymerization initiator.
  • photoradical polymerization initiator examples include imidazole derivatives, bisimidazole derivatives, N-aryl glycine derivatives, organic azide compounds, titanocene, aluminate complexes, organic peroxides, N-alkoxypyridinium salts, Derivatives, and amine derivatives.
  • examples of the photocatalytic polymerization initiator include 1,3-di (t-butyldioxycarbonyl) benzophenone, 3,3 ', 4,4'-tetraxy (t-butyidoxycarbonyl) benzophenone, 3-pheny 5-i soxazo 1 one, 2-mercapto benzimidazole, bi s (2, 4, 5-tr ipheny 1) imidazole, 2,2-dimethoxy- BASF), 1-hydroxy-cyclohexyl-phenyl-ketone (product name: Irgacure 184 / manufacturer: BASF), 2-benzyl-2 di methylhydro1- (4-morpholinopheny 1) but anone- 1 (product name: Irgacure 369 / Manufacturer: BASF), and bis (r
  • photocationic polymerization initiator examples include a diazonium salt, a sulfonium salt, and iodonium salt, and examples thereof include sulfonic acid ester, imidosulfonate ( 1) 6 -benzene) (r. 5- cyclopentadienyl) iron (II), and the like can be used as the dialkyl-4-hydroxysulfonium salt, arylsulfonic acid-p-nitrobenzyl ester, silanol-aluminum complex Further, benzoin tosylate,
  • cationic polymerization initiator examples include Cyracure UVI-6970, Cyracure UVI-6974 and Cyracure UVI-6990 (manufactured by Dow Chemical Co. in USA), Irgacure 264 and Irgacure 250 - 1682 (Manufacturer: Ni-on-Soda).
  • the photoanion polymerization initiator examples include a borate salt, such as butyrylchlorine butyl triphenyl borate (BUTYRYL CHOLINE BUTYL TRIPHENYLBORATE). More specific examples of the photoanion polymerization initiator include commercially available products such as Borate V (manufacturer: Spectra group). - In addition, the photopolymer composition of this embodiment may use one molecule (Type I) or two molecules (Type I I) initiator.
  • the (Type I) system for the free radical photopolymerization is, for example, an aromatic ketone compound in combination with a tertiary amine such as benzophenone, alkylbenzophenone, 4,4'-bis (dimethylamino)
  • the bis (type II) initiators include benzoin and derivatives thereof, benzyl ketal, acylphosphine oxides such as 2,4,6-trimethylbenzoyldiphenylphosphine oxide, bisacylphosphine oxide, phenylglycine Alpha-aminoalkylacetophenone, 1- [4- (phenylthio) phenyl] octane-1,2-dione 2- (0-benzoyloxime) and alpha -Hydroxyalkylphenone, and the like.
  • the photopolymer composition of this embodiment comprises 1 to 80% by weight of the polymeric matrix or precursor thereof; 1% to 80% by weight of the photoreactive monomer; 0.0001 to 10% by weight of the dye; And 0.1% to 20% by weight of a photoinitiator.
  • the photopolymer composition further comprises an organic solvent
  • the content of the above-mentioned components is based on the total of these components (the sum of the components excluding the organic solvent).
  • the hologram recording medium may further include at least one member selected from the group consisting of a catalyst, a phosphate compound, and a low refractive index fluorine compound.
  • the phosphate compound and the low refractive index fluorine compound have a lower refractive index than the photoreactive monomer, thereby lowering the refractive index of the polymer matrix, thereby maximizing the refractive index modulation of the photopolymer composition. Furthermore, the phosphate-based compound acts as a plasticizer to increase the mobility of the photoreactive monomer and the low refractive index by lowering the glass transition temperature of the polymer matrix, thereby contributing to the improvement of moldability of the photopolymer composition.
  • the refractive index of the polymer matrix can be lowered when added to the photopolymer composition, thereby maximizing the refractive index modulation with the monomer .
  • the fluorine-based compound may include at least one functional group selected from the group consisting of an ether group, an ester group and an amide group, and at least two difluoromethylenes groups. More specifically, the fluorine-based compound may have a structure represented by the following formula (4) in which a functional group including an ether group is bonded at both ends of a direct bond or a central functional group including an ether bond in two difluoromethylene periods.
  • R n and R 12 are each independently a difluoromethylene group
  • Ris and R 16 are each independently a methylene group
  • Ri 4 and R 15 are each independently a difluoromethylen group
  • Ri 7 and R 18 are each independently a polyalkylene oxide group
  • m is an integer of 1 or more, or 1 to 10, or an integer of 1 to 3.
  • R n and R 12 each independently represent a difluoromethylene group
  • R 13 and R 16 each independently represents a methylene group
  • R 14 and R 15 each independently represent a fluoromethylene Riy and R 18 are each independently a 2-methoxyethoxymethoxy group
  • m is an integer of 2.
  • the fluorine-based compound may have a refractive index of less than 1.45, or more than 1.3 and less than 1.45. As described above, since the photoreactive monomer has a refractive index of 1.5 or more, the fluorine-based compound has a refractive index lower than that of the photoreactive monomer, 2019/117538 1 »(: 1 ⁇ ⁇ 2018/015464
  • the refractive index of the matrix can be lowered , and the refractive index modulation with the monomer can be maximized.
  • the content of the fluorine-based compound may be 30 parts by weight to 150 parts by weight, or 50 parts by weight to 110 parts by weight based on 100 parts by weight of the light-reactive monomer.
  • the content of the fluorine-based compound is excessively decreased with respect to 100 parts by weight of the photoreactive monomer, the refractive index modulation value after recording is lowered due to the lack of the low refractive index, and the content of the fluorine-based compound is excessively increased with respect to 100 parts by weight of the photoreactive monomer , There may arise haze due to compatibility with other components or a problem that some fluorine compounds are eluted to the surface of the coating layer.
  • the fluorine-based compound may have a weight average molecular weight of about 300 or more, or about 300 to about 1,000.
  • a specific method of measuring the weight average molecular weight is as described above.
  • phosphate compound examples include triphenyl phosphate, tricresyl phosphate, cresyldiphenyl phosphate, octyldiphenyl phosphate, diphenyl biphenyl phosphate, trioctyl phosphate, tributyl phosphate and the like.
  • the phosphate compound may be added together with the above-mentioned fluorine compound at a weight ratio of 1: 5 to 5: 1.
  • the phosphate compound may have a refractive index of less than 1.5 and a molecular weight of 700 or less.
  • the photopolymer composition may further include other additives, a catalyst, and the like.
  • the photopolymer composition may comprise a catalyst commonly known for promoting polymerization of the polymer matrix or light-reactive monomer.
  • the catalyst include tin octanoate, zinc octanoate dibutyl tin dilaurate, dimethyl bis [(1-oxoneodecyl) oxy] stannane, dimethyl tin dicarboxylate, zirconium bis ( 1) or zirconium acetylacetonate, ⁇ ) -toluenesulfonic acid ( ⁇ ) -1: 0 1 116116311 1 1 1 or a tertiary amine such as 1,4-diazabicyclo [2.2.
  • Diazabicyclononane diazabicycloundecane, 1,1,3,3-tetramethylguanidine, 1,3,4,6,7,8-hexahydro- 1-methyl-2H-pyrimido (1,2-a) pyrimidine, and the like.
  • the other additives include a defoaming agent, and the defoaming agent may be a silicone-based reactive additive, for example, Tego Rad 2500.
  • the photopolymer composition of the embodiment may further include a photoreactive dye different from the above-described compound of formula (1).
  • the photosensitive dye acts as an enhancer for increasing or decreasing the photoinitiator. More specifically, the photosensitive dye is stimulated by light irradiated to the photopolymer composition to serve as an initiator for initiating the polymerization of the monomer and the crosslinking monomer can do.
  • the examples of the photosensitive dye different from the compound of the formula (1) are not limited to a wide variety.
  • Specific examples of the photosensitive dye include a sulfonium derivative of ceramidonine (sul fonium derivative ive), new methylene blue, thioerythrosine triethylammonium, 6-acetylamino-2 - 6-acetylamino 2-i Ti ethylcerate Ti idonin, eosin, ery ratio irosine, rose bengal, thionine, basic yellow ), Pinacyanol chloride, rhodamine 6G, gal 1 ° Cyanine, ethyl violet, Vi ctor ia blue R, Celestine Blue (Celest ine blue), QuinaldineRed, crystal violet, Brilli ant Green, Astrazon orange G, darrow red, pyronein Y pyronin Y, basic red 29, I (pyryl ium iodide),
  • Such an organic solvent include ketones such as methyl ethyl ketone, methyl isobutyl ketone, acetylacetone or isobutyl ketone; Alcohols such as methanol, ethanol,? -Propanol, propanol, 11- butanol, butanol, or butanol; Ethyl acetate, propyl acetate, or polyethylene glycol monomethyl ether acetate; Ethers such as tetrahydrofuran or propylene glycol monomethyl ether; Or mixtures of two or more thereof.
  • ketones such as methyl ethyl ketone, methyl isobutyl ketone, acetylacetone or isobutyl ketone
  • Alcohols such as methanol, ethanol,? -Propanol, propanol, 11- butanol, butanol, or butanol
  • the organic solvent may be added to the photopolymer composition at the time of mixing the components contained in the photopolymer composition for producing the hologram recording medium, or may be added to the photopolymer composition while the components are dispersed or mixed in the organic solvent. If the content of the organic solvent in the photopolymer composition is too small, the flowability of the photopolymer composition may be deteriorated, resulting in defects such as streaks in the finally produced film. In addition, when the organic solvent is added in an excess amount, the solid content is lowered and the coating and film formation are not sufficiently performed, so that the physical properties and surface characteristics of the film may be deteriorated, and defects may occur during the drying and curing process.
  • the photopolymer composition may comprise an organic solvent such that the concentration of the total solids of the components contained is from 1 wt% to 70 wt%, or from 2 wt% to 50 wt%.
  • the hologram recording medium can realize a refractive index modulation peak value of 0.020 or more, 0.021 or more, 0.022 or even 0.0225 to 0.035 even in the thickness of 5 to 30).
  • the hologram recording medium A diffraction efficiency of 50% or more, or 85% or more, or 85 to 99% at a thickness of 30 can be realized.
  • the photopolymer composition for producing the hologram recording medium is prepared by homogeneously mixing the respective components contained therein, After the drying and curing at temperatures above, and exposure through a predetermined process can be made of a hologram for optical applications in the entire visible range and the near ultraviolet region (300 to 800 1 L). 2019/117538 1 »(: 1 ⁇ ⁇ 2018/015464
  • the polymer matrix or the precursor-forming component thereof may first be uniformly mixed, and the silane crosslinking agent may be mixed with the catalyst to prepare a process for forming a hologram.
  • the above-mentioned photopolymer composition can be used without any limitations, such as a mixer, a stirrer or a mixer commonly known in the art, and the temperature in the mixing process is preferably 0 ° C to 100 ° C ⁇ .
  • the polymer matrix or its precursor-forming component may first be homogeneously mixed and then a liquid formulation which is cured at a temperature of 20 ° C or higher.
  • the temperature of the curing may vary depending on the composition of the photopolymer and is promoted, for example, by heating to a temperature of 30 to 180 DEG C.
  • the photopolymer may be injected into a predetermined substrate or mold or coated.
  • a method of recording a visual hologram on a hologram recording medium manufactured from the photopolymer composition can use a conventionally known method without any limitation, and the method described in the holographic recording method of the embodiment to be described later can be adopted as an example have.
  • a holographic recording method may be provided, which comprises selectively polymerizing the photoreactive monomer contained in the photopolymer composition by a coherent laser.
  • a medium in a state in which no visual hologram is recorded can be manufactured, and a visual hologram can be recorded on the medium through a predetermined exposure process.
  • a visual hologram can be recorded on media provided through the process of mixing and curing the photopolymer composition, using known devices and methods under commonly known conditions.
  • an optical element including a hologram recording medium can be provided.
  • the optical element include an optical lens, a mirror, a deflecting mirror, a filter, a diffusing screen, a diffraction member, a light guide, a waveguide, a holographic optical element having a function of a projection screen and / A diffusion plate, a light wavelength splitter, a reflection type, and a transmission type color filter.
  • An example of an optical element including the hologram recording medium is a hologram display device.
  • the hologram display device includes a light source unit, an input unit, an optical system, and a display unit.
  • the light source unit irradiates a laser beam used for providing, recording, and reproducing three-dimensional image information of an object in an input unit and a display unit.
  • the input unit pre-inputs three-dimensional image information of an object to be recorded on the display unit.
  • the input unit may include an object such as an intensity and a phase of a space star light in an electric driving liquid crystal SLM (electronically addressed lid crystal SLM) Dimensional information of the input beam can be input, and the input beam can be used at this time.
  • the optical system may include a mirror, a polarizer, a beam splitter, a beam shutter, a lens, and the like.
  • the optical system includes an input beam for transmitting a laser beam emitted from a light source unit to an input unit, a recording beam for sending to a display unit, The beam can be distributed by the beam.
  • the display unit receives the three-dimensional image information of the object from the input unit, records the three-dimensional image information on the hologram plate made of the optically driven SLM (SLM), and reproduces the three-dimensional image of the object.
  • the three-dimensional image information of the object can be recorded through the interference between the input beam and the reference beam.
  • the three-dimensional image information of the object recorded on the hologram plate can be reproduced as a three-dimensional image by the diffraction pattern generated by the reader, and the eraser can be used to quickly remove the formed diffraction pattern.
  • the hologram plate can be moved between a position for inputting the 3D image and a position for reproducing the 3D image.
  • a compound having a novel structure a hologram having a thin thickness, a high refractive index modulation value and a high durability against temperature and humidity
  • the dye synthesized in a methyl ethyl ketone (MEK) solvent was diluted to O.OOlwt% using a UV-Vis spectrophotometer to obtain a dye having a wavelength of 380 nm to 780 nm ⁇ 301 33 ⁇ 4: to 6 (%) measurements were calculated the maximum absorption wavelength.
  • MEK methyl ethyl ketone
  • the above synthesized product 8 (1.5 g, 0.0019 mol) was dissolved in 100 ml of toluene and the solution was heated to reflux. 100 ml of toluene in which DDQ (2, 3-D i ch 1 oro-5, 6-di cyano-p-benzoquinone, 3.9 g, 0.0175 mol) was dissolved was added and refluxing was continued for 4 hours. The reaction was cooled and the solvent was removed in vacuo. The residue was dissolved in ethyl acetate and the solution was washed with saturated sodium bicarbonate (100 ml x 3) and brine (100 ml) and dried over magnesium sulfate.
  • AIBN which is a polymerization initiator
  • a holographic recording was made through interference of two interfering lights (reference light and object light), and the transmissive recording made the two beams incident on the same side of the sample.
  • the diffraction efficiency changes according to the incident angle of the two beams, and becomes non-s l anted when the two incident angles are the same.
  • the non-sl anted recording is generated perpendicular to the film because the incident angles of the two bands are equal to the normal reference.
  • the refractive index modulation value (An) can be calculated from the general formula (2) of the lossless diode selection grating of the transmission type hologram.
  • the hologram recording media of Examples 1 to 4 can realize a refractive index modulation value (II) of 0.022 or more at a thickness of 6.5_.
  • the hologram recording media of Comparative Examples 1 and 2 had a relatively low diffraction efficiency as compared with the Examples, and the hologram recording of Comparative Example 3 using the dipyrromethene boron complex of formula (10) The medium showed very low diffraction efficiency.

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  • Spectroscopy & Molecular Physics (AREA)
  • General Physics & Mathematics (AREA)
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  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
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Abstract

La présente invention concerne un composé ayant une nouvelle structure, une composition photopolymère comprenant le composé en tant que colorant, un support d'enregistrement d'hologramme produit à partir de la composition photopolymère, un élément optique comprenant le support d'enregistrement d'hologramme, et un procédé d'enregistrement holographique faisant appel au support d'enregistrement d'hologramme.
PCT/KR2018/015464 2017-12-15 2018-12-07 Composé colorant et composition photopolymère Ceased WO2019117538A1 (fr)

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JP2020518727A JP7012975B2 (ja) 2017-12-15 2018-12-07 染料化合物およびフォトポリマー組成物
US16/651,906 US11084933B2 (en) 2017-12-15 2018-12-07 Dye compound and photopolymer composition

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JP2002169275A (ja) * 2000-12-04 2002-06-14 Mitsui Chemicals Inc 光酸発生剤及びそれを用いた可視光感光性樹脂組成物
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JP2002169275A (ja) * 2000-12-04 2002-06-14 Mitsui Chemicals Inc 光酸発生剤及びそれを用いた可視光感光性樹脂組成物
KR101474900B1 (ko) * 2006-09-27 2014-12-19 후지필름 가부시키가이샤 화합물 또는 이것의 토토머, 금속착체 화합물, 착색 감광성경화 조성물, 컬러필터, 및 제조
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