# US 12,001,141 B2 · Photopolymer composition > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 12,001,141 B2 - Document ID: US12001141B2 - Status: Granted - Kind: B2 - Application number: 16/976,206 - Filed: 2019-04-29 - Published: 2021-01-07 - Granted: 2024-06-04 - Earliest claimed: 2018-06-01 - Assignees: LG Chem, Ltd.; Korea Advanced Institute of Science and Technology - Applicants: LG Chem, Ltd.; Korea Advanced Institute of Science and Technology - Inventors: Heon Kim; Yoosik Kim; Raisa Kharbash; Se Hyun Kwon; Yeongrae Chang; Seokhoon Jang - Web page: https://patentgrep.com/patent/US12001141B2 ## CPC - C09B 11/28: Pyronines {; Xanthon, thioxanthon, selenoxanthan, telluroxanthon dyes} - G03F 7/0755: {Non-macromolecular compounds containing Si-O, Si-C or Si-N bonds (G03F7/0752 takes precedence)} - C07F 7/081: {comprising at least one atom selected from the elements N, O, halogen, S, Se or Te} - C09B 11/24: Phthaleins containing amino groups {; Phthalanes; Fluoranes; Phthalides; Rhodamine dyes; Phthaleins having heterocyclic aryl rings; Lactone or lactame forms of triarylmethane dyes} - C09B 57/00: Other synthetic dyes of known constitution - C09B 69/103: {containing a diaryl- or triarylmethane dye} - G02B 5/1857: {using exposure or etching means, e.g. holography, photolithography, exposure to electron or ion beams} - G02B 5/32: Holograms used as optical elements - G03F 7/028: with photosensitivity-increasing substances, e.g. photoinitiators - G03F 7/029: Inorganic compounds; Onium compounds; Organic compounds having hetero atoms other than oxygen, nitrogen or sulfur - G03F 7/033: the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers - G03F 7/035: the binders being polyurethanes - G03F 7/0758: {with silicon- containing groups in the side chains} - G03F 7/105: having substances, e.g. indicators, for forming visible images - G03H 1/0402: {Recording geometries or arrangements (G03H1/0443, G03H1/0476, G03H1/16 take precedence)} - G03H 2001/0439: {for recording Holographic Optical Element [HOE]} - G03H 2260/12: Photopolymer - C09B: ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES {, e.g. PIGMENTS}; MORDANTS; LAKES (fermentation or enzyme using processes to synthesise a desired chemical compound C12P) - 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; (phototypographic composing devices B41B; photosensitive materials or processes for photographic purposes G03C; electrophotography, sensitive layers or processes therefor G03G) - C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22) - G02B: OPTICAL ELEMENTS, SYSTEMS OR APPARATUS - G03H: HOLOGRAPHIC PROCESSES OR APPARATUS (holograms, e.g. point holograms, used as ordinary optical elements G02B5/32; producing stereoscopic or other three-dimensional effects G02B30/00; diffraction-grating systems G02B27/44; systems using moiré fringes G02B27/60; optical logic elements G02F3/00; stereo-photography G03B35/00; photosensitive materials or processes for photographic purposes G03C; {stereo-photographic or similar processes G03C9/00}; apparatus for processing exposed photographic materials G03D; analogue computers performing mathematical operations with the aid of optical elements G06E3/00; authentication by radiation, of concealed information carried by holograms or diffraction gratings G06K19/16; holographic storage G11B7/0065, G11C13/04; {stereoscopic or other three dimensional effects in television systems H04N13/00}) ## Abstract The present disclosure relates to a photopolymer composition, and more particularly, to a compound having a novel structure, a photopolymer composition including the compound as a dye, a hologram recording medium produced from the photopolymer composition, an optical element including the hologram recording medium, and a holographic recording method using the photopolymer composition. ## Claims ### Claim 1 A photopolymer composition comprising: a polymer matrix or a precursor thereof; a dye including a compound represented by Chemical Formula 1; a photoreactive monomer; and a photoinitiator: in the Chemical Formula 1, X is silicon (Si), Z1 and Z2 are identical to or different from each other, and each is nitrogen (N) or phosphorus (P), R1 to R12 are identical to or different from each other, and each is hydrogen, an alkyl group having 1 to 20 carbon atoms; a halogen group; a nitrile group; a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms; a substituted or unsubstituted aryloxy group having 6 to 20 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, n and m are each 0 or 1, An− is an anion, Ar1 is an aromatic divalent functional group having 6 to 30 carbon atoms unsubstituted or substituted with one or more functional groups selected from the group consisting of an alkyl group having 1 to 20 carbon atoms; a halogen group; a nitrile group; an alkoxy group having 1 to 20 carbon atoms; an aryloxy group having 6 to 20 carbon atoms and an aryl group having 6 to 20 carbon atoms, and Y1 is a functional group represented by Chemical Formula 2, wherein, in the Chemical Formula 2, Y2 is an ether group or an ester, and Ar2 is an aromatic functional group having 6 to 20 carbon atoms substituted with one or more halogen groups. ### Claim 2 (depends on 1) The photopolymer composition according to claim 1, wherein in the Chemical Formula 1, An− is a halide ion, a cyano ion, an alkoxy ion having 1 to 30 carbon atoms, an alkoxycarbonyl ion having 1 to 30 carbon atoms, a sulfonate ion, an alkyl-sulfonate ion having 1 to 30 carbon atoms, a substituted or unsubstituted aromatic sulfonate ion having 6 to 30 carbon atoms, an alkyl sulfate ion having 1 to 30 carbon atoms, a sulfate ion, or a substituted or unsubstituted aromatic sulfate ion having 6 to 30 carbon atoms. ### Claim 3 (depends on 1) The photopolymer composition according to claim 1, wherein in the Chemical Formula 1, n and m are each 1, Z1 and Z2 are each nitrogen (N), R1 to R12 are identical to or different from each other, and each is hydrogen, an alkyl group having 1 to 20 carbon atoms; or a halogen group, and Ar1 is an aromatic divalent functional group having 6 to 20 carbon atoms to which at least one hydrogen, an alkyl group having 1 to 20 carbon atoms or halogen group is bonded. ### Claim 4 (depends on 1) The photopolymer composition according to claim 1, wherein the polymer matrix or a precursor thereof includes a silane crosslinking agent; and 1) a reaction product between a compound containing one or more isocyanate groups and a polyol; or 2) a polymer matrix including a (meth)acrylate-based (co)polymer having a silane-based functional group in a branched chain. ### Claim 5 (depends on 4) The photopolymer composition according to claim 4, wherein the silane crosslinking agent includes a linear polyether main chain having a weight average molecular weight of 100 to 2000, and a silane-based functional group bonded at a terminal end or a branched chain of the main chain. ### Claim 6 (depends on 4) The photopolymer composition according to claim 4, wherein the (meth)acrylate-based (co)polymer includes a (meth)acrylate repeating unit and a (meth)acrylate repeating unit having a silane-based functional group in a branched chain, and has a weight average molecular weight of 100,000 to 1,000,000. ### Claim 7 (depends on 1) The photopolymer composition according to claim 1, wherein the photoreactive monomer includes a polyfunctional (meth)acrylate monomer, or a monofunctional (meth)acrylate monomer. ### Claim 8 (depends on 1) The photopolymer composition according to claim 1, comprising 1% to 80% by weight of the polymer matrix or a 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 the photoinitiator. ### Claim 9 (depends on 1) The photopolymer composition according to claim 1, further comprising at least one compound selected from the group of a catalyst, a phosphate-based compound, and a low refractive index fluorine-based compound. ### Claim 10 (depends on 9) The photopolymer composition according to claim 9, wherein the low refractive index fluorine-based compound includes at least one functional group selected from the group of an ether group, an ester group and an amide group; and at least two difluoromethylene groups. ### Claim 11 (depends on 1) The photopolymer composition according to claim 1, wherein the photopolymer composition is for hologram recording. ### Claim 12 (depends on 1) A hologram recording medium comprising a cured product of the photopolymer composition of claim 1, wherein the hologram recording medium comprises one or more stored holograms. ### Claim 13 (depends on 12) An optical element comprising the hologram recording medium of claim 12. ### Claim 14 (depends on 13) The optical element according to claim 13, the optical element being a hologram display device. ### Claim 15 (depends on 1) A holographic recording method comprising selectively polymerizing photoreactive monomers of the photopolymer composition of claim 1 by a coherent laser, wherein a light interference pattern is stored as a hologram by photopolymerization of the photopolymer composition.