WO2021006011A1 - 化合物、ポリマー及び有機材料、並びにこれを用いた光学装置、光学部品及び画像表示装置 - Google Patents

化合物、ポリマー及び有機材料、並びにこれを用いた光学装置、光学部品及び画像表示装置 Download PDF

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WO2021006011A1
WO2021006011A1 PCT/JP2020/024149 JP2020024149W WO2021006011A1 WO 2021006011 A1 WO2021006011 A1 WO 2021006011A1 JP 2020024149 W JP2020024149 W JP 2020024149W WO 2021006011 A1 WO2021006011 A1 WO 2021006011A1
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compound
hydrocarbon group
organic
organic material
chemical formula
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French (fr)
Japanese (ja)
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貴裕 大江
援又 原
健志郎 川崎
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Sony Corp
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Sony Corp
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Priority to KR1020217042887A priority Critical patent/KR20220029590A/ko
Priority to JP2021530567A priority patent/JPWO2021006011A1/ja
Priority to EP20836829.0A priority patent/EP3995491A4/en
Priority to CN202080048914.9A priority patent/CN114174262A/zh
Priority to US17/625,674 priority patent/US20220289678A1/en
Priority to TW109122304A priority patent/TW202110797A/zh
Publication of WO2021006011A1 publication Critical patent/WO2021006011A1/ja
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
    • C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
    • C08F20/10—Esters
    • C08F20/12—Esters of monohydric alcohols or phenols
    • C08F20/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F20/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
    • C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
    • C08F20/10—Esters
    • C08F20/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F22/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides or nitriles thereof
    • C08F22/10—Esters
    • C08F22/1006—Esters of polyhydric alcohols or polyhydric phenols, e.g. ethylene glycol dimethacrylate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F263/00—Macromolecular compounds obtained by polymerising monomers on to polymers of esters of unsaturated alcohols with saturated acids as defined in group C08F18/00
    • C08F263/02—Macromolecular compounds obtained by polymerising monomers on to polymers of esters of unsaturated alcohols with saturated acids as defined in group C08F18/00 on to polymers of vinyl esters with monocarboxylic acids
    • C08F263/04—Macromolecular compounds obtained by polymerising monomers on to polymers of esters of unsaturated alcohols with saturated acids as defined in group C08F18/00 on to polymers of vinyl esters with monocarboxylic acids on to polymers of vinyl acetate
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
    • C09D4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09D159/00 - C09D187/00
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
    • G02B1/041—Lenses
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B3/00—Simple or compound lenses
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
    • G03F7/001—Phase modulating patterns, e.g. refractive index patterns
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03H—HOLOGRAPHIC PROCESSES OR APPARATUS
    • 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
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03H—HOLOGRAPHIC PROCESSES OR APPARATUS
    • G03H1/00—Holographic processes or apparatus using light, infrared or ultraviolet waves for obtaining holograms or for obtaining an image from them; Details peculiar thereto
    • G03H1/02—Details of features involved during the holographic process; Replication of holograms without interference recording
    • G03H2001/026—Recording materials or recording processes
    • G03H2001/0264—Organic recording material
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03H—HOLOGRAPHIC PROCESSES OR APPARATUS
    • G03H2260/00—Recording materials or recording processes
    • G03H2260/12—Photopolymer

Definitions

  • This technology relates to compounds, polymers and organic materials, as well as optical devices, optical components and image display devices using the same.
  • High-performance organic materials have superior design flexibility and impact resistance compared to inorganic materials, and are lightweight. Therefore, application studies to optical materials such as organic thin films, organic lenses, and holograms have been actively conducted. The current situation is that there is.
  • Patent Document 1 proposes a method of imparting a refractive index of an article using a compound having a dibenzothiophene skeleton.
  • Patent Document 2 proposes a refractive index improver containing a compound having a dinaphthophene skeleton.
  • the main object of this technology is to provide compounds and polymers capable of further enhancing the functionality of organic materials, organic materials having high functionality, optical devices, optical components and image display devices using the same. And.
  • the present technology provides a compound represented by the following general formula (1).
  • X 1 is an oxygen atom, a nitrogen atom, a phosphorus atom, a carbon atom or a silicon atom. If X 1 is an oxygen atom, a is 0, if X 1 is a nitrogen or phosphorus atom, a is 1, and if X 1 is a carbon or silicon atom, a is 2. .. Y 1 and Y 2 are benzene rings or naphthalene rings, respectively, and Y 1 and Y 2 are not benzene rings at the same time. When Y 1 or Y 2 is a benzene ring, b or c corresponding to the benzene ring Y 1 or Y 2 is 4.
  • R 1 to R 3 are hydrogen or substituents represented by * -Z 1 (R 4 ) d (* represents a bond position), respectively.
  • R 1 ⁇ R 3 is present in plural, a plurality of R 1 ⁇ R 3 may be the being the same or different, but the general formula (1) all R 1 ⁇ R 3 in It cannot be hydrogen at the same time.
  • Z 1 represents a monobond, a divalent or higher saturated hydrocarbon group or a divalent or higher unsaturated hydrocarbon group, and the saturated hydrocarbon group or unsaturated hydrocarbon group may contain an ether bond and / or a thioether bond. .. If Z 1 is a single bond, d is 1, and if Z 1 is a saturated or unsaturated hydrocarbon group, d is an integer greater than or equal to 1.
  • R 4 represents hydrogen or a polymerizable substituent. If R 4 there are a plurality, the plurality of R 4 may be independently identical or different from each other, but not all of R 4 in the general formula (1) are simultaneously hydrogen.
  • X 1 of the general formula (1) may be a nitrogen atom.
  • the compound may be a compound represented by the following general formula (1-1).
  • R 1 , R 21 to R 26 , and R 31 to R 36 are hydrogen or substitutions represented by * -Z 1 (R 4 ) d (* represents a bond position). Is the basis. R 1 , R 21 to R 26 , and R 31 to R 36 may be the same or different from each other. However, R 1 , R 21 to R 26 , and R 31 to R 36 in the general formula (1-1) are not all hydrogen at the same time.
  • Z 1 represents a monobond, a divalent or higher saturated hydrocarbon group or a divalent or higher unsaturated hydrocarbon group, and the saturated hydrocarbon group or unsaturated hydrocarbon group may contain an ether bond and / or a thioether bond. ..
  • the present technology also provides organic materials containing the compounds.
  • the organic material may be an organic thin film, an organic lens or a hologram. Further, the organic material may be a composition for an organic thin film, a composition for an organic lens, or a photosensitive composition for hologram recording.
  • the present technology also provides a polymer obtained by polymerizing the compound.
  • the present technology also provides a copolymerized polymer obtained by polymerizing the compound and other polymerizable compounds.
  • the art also provides organic materials containing the polymers.
  • the organic material may be an organic thin film, an organic lens or a hologram. Further, the organic material may be a composition for an organic thin film, a composition for an organic lens, or a photosensitive composition for hologram recording.
  • the present technology also provides an optical device that includes the organic material.
  • the present technology also provides optical components, including the organic material. Further, the present technology also provides an image display device containing the organic material.
  • the present technology also provides a composition containing the compound and a radically polymerizable monomer.
  • the radically polymerizable monomer may be one or more selected from a carbazole-based monomer, a dinaphthophene-based monomer, a fluorene-based monomer, and a dibenzofuran-based monomer.
  • FIG. 1 is a cross-sectional view schematically showing an example of a hologram recording medium according to an embodiment of the present technology.
  • the present technology relates to compounds, polymers and organic materials, and optical devices, optical components and image display devices using the same.
  • Organic compounds and polymers are called high-refractive index materials when, for example, the refractive index exceeds 1.5.
  • the refractive index exceeds 1.5.
  • a compound having a high refractive index is applied to an optical material, the following facts exist. -It has low solubility in organic solvents, and it is difficult to form a film using a solution. -The compatibility with the resin is poor, and the compound concentration in the mixture cannot be increased. -Some compounds are colored and are not suitable for application to transparent thin films and lenses.
  • a compound having high functionality for example, high refractive index, transparency and good solubility in an organic solvent is required.
  • an organic compound having a specific skeleton and having a polymerizable substituent has a high refractive index, and has good transparency and solubility in an organic solvent. I found it.
  • the compound of the first embodiment according to the present technology is a compound represented by the following general formula (1).
  • the compound of the first embodiment according to the present technology can realize further high functionality of the organic material. That is, the compound of the first embodiment according to the present technology has a high refractive index, and has good transparency and solubility in an organic solvent.
  • X 1 is an oxygen atom, a nitrogen atom, a phosphorus atom, a carbon atom or a silicon atom. If X 1 is an oxygen atom, a is 0, if X 1 is a nitrogen or phosphorus atom, a is 1, and if X 1 is a carbon or silicon atom, a is 2. .. Y 1 and Y 2 are benzene rings or naphthalene rings, respectively, and Y 1 and Y 2 are not benzene rings at the same time. When Y 1 or Y 2 is a benzene ring, b or c corresponding to the benzene ring Y 1 or Y 2 is 4.
  • R 1 to R 3 are hydrogen or substituents represented by * -Z 1 (R 4 ) d (* represents a bond position), respectively.
  • R 1 ⁇ R 3 is present in plural, a plurality of R 1 ⁇ R 3 may be the being the same or different, but the general formula (1) all R 1 ⁇ R 3 in It cannot be hydrogen at the same time.
  • Z 1 represents a monobond, a divalent or higher saturated hydrocarbon group or a divalent or higher unsaturated hydrocarbon group, and the saturated hydrocarbon group or unsaturated hydrocarbon group may contain an ether bond and / or a thioether bond. .. If Z 1 is a single bond, d is 1, and if Z 1 is a saturated or unsaturated hydrocarbon group, d is an integer greater than or equal to 1.
  • R 4 represents hydrogen or a polymerizable substituent. If R 4 there are a plurality, the plurality of R 4 may be independently identical or different from each other, but not all of R 4 in the general formula (1) are simultaneously hydrogen.
  • X 1 is an oxygen atom, a nitrogen atom, a phosphorus atom, a carbon atom or a silicon atom. Further, it is considered that the effect of this technique can be expected for Group 14 elements, Group 15 elements and Group 16 elements (excluding transition metals) other than the above.
  • oxygen atom, nitrogen atom, and carbon atom which are typical elements of organic compounds, are preferable from the viewpoint of easiness of synthesizing the compound, and each atomic refraction is oxygen atom: 1.6 to 2.2.
  • Nitrogen atom: 3.5-4.4, carbon atom: 1.7-2.4 Optical, Vol. 44, No. 8, 2015, p298-303.
  • X 1 of the general formula (1) is a nitrogen atom having a high value of atomic refraction.
  • the compound of the present embodiment may have the following structure.
  • Y 1 and Y 2 are benzene rings or naphthalene rings, respectively, and Y 1 and Y 2 are not benzene rings at the same time.
  • Y 1 or Y 2 is a benzene ring
  • b or c corresponding to the benzene ring Y 1 or Y 2 is 4.
  • Y 1 and / or Y 2 is a naphthalene ring
  • b and / or c corresponding to the naphthalene ring Y 1 and / or Y 2 is 6.
  • R 1 , R 2 , R 3 , R 11 and R 12 are hydrogen or substituents represented by * -Z 1 (R 4 ) d (* represents a bond position), respectively.
  • R 1 ⁇ R 3 is present in plural, a plurality of R 1 - R 3 may be the being the same or different, but the general formula (2-1) to (2-5) in the Not all of R 1 , R 2 , R 3 , R 11 and R 12 are hydrogen at the same time.
  • Z 1 represents a monobond, a divalent or higher saturated hydrocarbon group or a divalent or higher unsaturated hydrocarbon group, and the saturated hydrocarbon group or unsaturated hydrocarbon group may contain an ether bond and / or a thioether bond. ..
  • R 4 represents hydrogen or a polymerizable substituent. If R 4 there are a plurality, the plurality of R 4 may be independently identical or different each other, the formula (2-1) to (2-5) in all R 4 are hydrogen at the same time in There is no such thing.
  • Y 1 and Y 2 are benzene rings or naphthalene rings, respectively, and Y 1 and Y 2 are not benzene rings at the same time.
  • the molecular refraction of phenyl (C 6 H 5 ) and naphthyl (C 10 H 7 ) is phenyl (C 6 H 5 ): 25.5, naphthyl (C 10 H 7 ): 43.3 (optics, 44th). Volume 8, 2015, p298-303).
  • Y 1 and Y 2 are naphthalene rings having high molecular refraction values, respectively.
  • the compound of the present embodiment may have the following structure.
  • X 1 is an oxygen atom, a nitrogen atom, a phosphorus atom, a carbon atom or a silicon atom. If X 1 is an oxygen atom, a is 0, if X 1 is a nitrogen or phosphorus atom, a is 1, and if X 1 is a carbon or silicon atom, a is 2. ..
  • R 1 , R 21 to R 26 , and R 31 to R 36 are hydrogen or substituents represented by * -Z 1 (R 4 ) d (* represents a bond position), respectively.
  • R 1 , R 21 to R 26 , and R 31 to R 36 may be the same or different from each other.
  • R 1 there are a plurality, the plurality of R 1 may be the being the same or different.
  • R 1 , R 21 to R 26 , and R 31 to R 36 in the general formulas (3-1) to (3-3) and (4-1) to (4-6) are all hydrogen at the same time. There is no such thing.
  • Z 1 represents a monobond, a divalent or higher saturated hydrocarbon group or a divalent or higher unsaturated hydrocarbon group, and the saturated hydrocarbon group or unsaturated hydrocarbon group may contain an ether bond and / or a thioether bond. .. If Z 1 is a single bond, d is 1, and if Z 1 is a saturated or unsaturated hydrocarbon group, d is an integer greater than or equal to 1.
  • R 4 represents hydrogen or a polymerizable substituent. If R 4 there are a plurality, the plurality of R 4 may be independently identical or different each other, the formula (3-1) to (3-3) and (4-1) to (4- 6) all R 4 in does not simultaneously hydrogen.
  • Z 1 represents a single bond, a divalent or higher saturated hydrocarbon group, or a divalent or higher unsaturated hydrocarbon group.
  • the saturated or unsaturated hydrocarbon group may contain an ether bond and / or a thioether bond.
  • Z 1 is a divalent or higher valent saturated hydrocarbon group
  • the saturated hydrocarbon group may be a linear, branched or cyclic substituted or unsubstituted hydrocarbon group.
  • organic compounds tend to obtain solubility more easily as the number of simple carbon chains is longer, while the refractive index tends to be lower as the number of simple carbon chains is longer. Therefore, the saturated hydrocarbon group preferably has a simple carbon chain number of 1 to 15, and more preferably 1 to 10.
  • the unsaturated hydrocarbon group is a linear, branched or cyclic substituted or unsubstituted hydrocarbon group or aromatic group.
  • the unsaturated hydrocarbon group preferably has a simple carbon chain number of 1 to 15, and more preferably 1 to 10.
  • the aromatic group is a substituted or unsubstituted divalent or higher aromatic group represented by the following chemical formulas (5-1) to (5-8). It is preferable to have.
  • five or more benzene rings are linearly connected, they have absorption in the visible light region and have a color, which may not be preferable from the viewpoint of transparency.
  • the aromatic group preferably has a structure in which four or more benzene rings are not linearly arranged, and the linear shape is preferably up to a benzene ring, a naphthalene ring, or an anthracene ring.
  • examples of the polymerizable substituent represented by R 4 include those having a polymerizable unsaturated group and those having a reactive substituent.
  • examples of those having a polymerizable unsaturated group include a vinyl group, an acrylic group, a methacryl group, an acrylamide group, a methacrylicamide group, a cyanoacrylate group, a cyanomethacrylate group, a vinyl ether group, a vinyl cyanide group, a vinyl nitrate group, and a conjugate.
  • examples thereof include a polyene group, a vinyl halide group, a vinyl ketone group, and a styryl group.
  • Examples of those having a reactive substituent include an epoxy group, an oxetane group, a hydroxyl group, an amino group, a carboxyl group, an acid anhydride group, an acid halide group, an isocyanate group and the like.
  • X 1 is a nitrogen atom and Y 1 and Y 2 are naphthalene rings, respectively. That is, the compound is preferably a compound represented by the following general formula (1-1).
  • R 1 , R 21 to R 26 , and R 31 to R 36 are hydrogen or substitutions represented by * -Z 1 (R 4 ) d (* represents a bond position). Is the basis. R 1 , R 21 to R 26 , and R 31 to R 36 may be the same or different from each other. However, R 1 , R 21 to R 26 , and R 31 to R 36 are not all hydrogen at the same time.
  • Z 1 represents a monobond, a divalent or higher saturated hydrocarbon group or a divalent or higher unsaturated hydrocarbon group, and the saturated hydrocarbon group or unsaturated hydrocarbon group may contain an ether bond and / or a thioether bond. ..
  • R 1 is a substituent represented by * -Z 1 (R 4 ) d (* represents a bonding position), and R 21 to R 26 and R 31 to R 36. Is preferably hydrogen.
  • the refractive index of the compound of the present embodiment is preferably 1.60 or more, more preferably 1.65 or more, and further preferably 1.70 or more.
  • the refractive index of the compound of the first embodiment is, for example, 1.80 or less, but may be more than 1.80.
  • the refractive index can be measured by the critical angle method or the spectroscopic ellipsometry method.
  • measurement can be performed using an Abbe refractive index meter ER-1 manufactured by Elma Sales Co., Ltd. (measurement wavelength is in the visible light region using 486 nm, 589 nm, 656 nm, etc.).
  • the polymer of the second embodiment according to the present technology is a polymer obtained by polymerizing the compound of the first embodiment according to the present technology.
  • the compound of the first embodiment according to the present technology is a monofunctional monomer or a polyfunctional (bifunctional) monomer
  • the compound of the first embodiment according to the present technology is polymerized to form a second according to the present technology.
  • the polymer of the embodiment can be prepared.
  • the compound of the first embodiment according to the present technology and other polymerizable compounds may be copolymerized. That is, the polymer of the second embodiment according to the present technology may be a copolymerized polymer obtained by polymerizing the compound of the first embodiment according to the present technology and other polymerizable compounds.
  • the polymer of the second embodiment according to the present technology can realize further high functionality of the organic material. That is, the polymer of the second embodiment according to the present technology has a high refractive index, and has good transparency and solubility in an organic solvent.
  • the organic material of the third embodiment according to the present technology is a material containing the compound of the first embodiment according to the present technology or the polymer of the second embodiment according to the present technology.
  • Examples of the organic material of the third embodiment according to the present technology include an organic thin film, an organic lens, a hologram, a composition for an organic thin film, a composition for an organic lens, a composition for hologram recording, and the like.
  • the organic thin film and the composition for the organic thin film, the organic lens and the composition for the organic lens, and the hologram and the composition for hologram recording will be described in detail.
  • the composition for an organic thin film of the present embodiment contains at least the compound of the first embodiment according to the present technology.
  • the organic thin film can be obtained by subjecting the composition for an organic thin film to a polymerization treatment such as light irradiation or heating. That is, the organic thin film contains the polymer of the second embodiment according to the present technology.
  • the organic thin film is a so-called polymer film, and is usually contained in one or more layers in a flat panel display such as a liquid crystal display (hereinafter, also referred to as LCD (Liquid Crystal Display)).
  • LCD Liquid Crystal Display
  • the organic thin film is incorporated into a flat panel display as, for example, a protective film in an LCD, a layer constituting an antireflection film, and the like.
  • organic thin films are widely used in various fields that require surface protection, antireflection, and the like.
  • the compound of the first embodiment according to the present technology has a high refractive index and good transparency and solubility in an organic solvent, it can be applied to an organic thin film having a high refractive index surface (for example, a refractive index gradient film). Can be used.
  • the polymer of the compound of the first embodiment having a refractive index of 1.60 or more is used as one of the organic thin films (polymer film). It is preferable to localize it on the surface layer portion on the surface side (high refractive index surface side). Further, as the compound of the first embodiment, two or more different kinds may be mixed and used at an arbitrary ratio.
  • the composition for an organic lens of the present embodiment contains at least the first compound according to the present technology.
  • the organic lens can be obtained by subjecting the composition for an organic lens to a polymerization treatment such as light irradiation or heating. That is, the organic lens contains the polymer of the second embodiment according to the present technology.
  • Organic lenses have the advantages of being lighter, harder to break, and easier to process than inorganic materials, and organic lenses are used for eyeglasses and cameras. Since the compound of the first embodiment according to the present technology has a high refractive index and good transparency, when used as an organic lens, the thickness of the lens can be made thinner than that of glass, and the like can be used in optical applications. It has the advantage of being excellent in convenience.
  • the composition for hologram recording of the present embodiment is a composition containing at least a photopolymerizable monomer, a photopolymerization initiator, a binder resin, and a polymerization inhibitor.
  • the photopolymerizable monomer the compound of the first embodiment according to the present technology can be used. Further, the photopolymerizable monomer may contain a radically polymerizable monomer other than the compound of the first embodiment according to the present technology.
  • the hologram recording composition of the present embodiment has high functionality, for example, has a high refractive index modulation amount ( ⁇ n), and an effect of excellent diffraction characteristics is exhibited.
  • any photopolymerizable monomer can be used.
  • monofunctional or polyfunctional carbazole-based monomers, dinaphthothiophene-based monomers, fluorene-based monomers, dibenzofuran-based monomers and the like can be mentioned, and one or more of these can be used.
  • the photopolymerization initiator contained in the hologram recording composition of the present embodiment is not particularly limited, and any photopolymerization initiator can be used, but imidazole-based, bisimidazole-based, and N are preferable.
  • -Aromatic glycine type organic azide compound type, organic boron compound type, titanosen type, aluminate complex type, organic peroxide type, N-alkoxypyridinium salt type, thioxanthone derivative type, sulfonic acid ester type, imidesulfonate type, Dialkyl-4-hydroxysulfonium salt system, aryl sulfonic acid-p-nitrobenzyl ester system, silanol-aluminum complex system, ( ⁇ 6-benzene) ( ⁇ 5-cyclopentadienyl) iron (II) system, ketone system, diaryliodonium Initiation of one or more radical polymerizations selected from salt-based, diarylio
  • the binder resin contained in the hologram recording composition of the present embodiment is not particularly limited, and any binder resin can be used, but a vinyl acetate-based resin is preferable, and polyvinyl acetate or a polyvinyl acetate thereof is preferable.
  • a hydrolyzate is preferably used, an acrylic resin is preferable, and a poly (meth) acrylic acid ester or a partial hydrolyzate thereof is preferably used.
  • the polymerization inhibitor contained in the hologram recording composition of the present embodiment is not particularly limited, and any optional polymerization inhibitor can be used.
  • quinone compounds such as hydroquinone; hindered phenol compounds; benzotriazole compounds; thiazine compounds such as phenothiazines can be mentioned, and one or more of these can be used.
  • the hologram recording composition of the present embodiment may further contain inorganic fine particles, a plasticizer, a sensitizing dye, a chain transfer agent, a solvent and the like.
  • the sensitizing dye may contain either or both of a dye having absorption in the visible light region and a UV sensitizing dye (anthracene compound, etc.) added for the purpose of improving the light efficiency during UV irradiation. Good.
  • only one kind of sensitizing dye may be used, and a plurality of kinds of sensitizing dyes may be used in order to correspond to a plurality of wavelengths.
  • a photopolymerizable monomer, a photopolymerization initiator, a binder resin, and a polymerization inhibitor are added in a predetermined amount to the above-mentioned solvent at room temperature or the like, and dissolved and mixed. , for example, can be manufactured. Further, the above-mentioned inorganic fine particles, plasticizer, sensitizing dye, chain transfer agent and the like may be added depending on the intended use and purpose.
  • the hologram recording composition of the present embodiment is formed on the transparent base material contained in the hologram recording medium described later, the hologram recording composition may be used as a coating liquid.
  • the hologram recording medium of the present embodiment contains at least a photocurable resin layer containing the above-mentioned hologram recording composition and at least one transparent substrate, and the photocurable resin layer is on the at least one transparent substrate. It is a hologram recording medium formed in.
  • the photocurable resin layer is formed on the first transparent base material, and the first transparent base material is not formed on the main surface of the photocurable resin layer.
  • a claw transparent base material may be formed to form a three-layer structure.
  • FIG. 1 shows a schematic cross-sectional view of an example of the hologram recording medium of the present embodiment.
  • a transparent protective film sometimes referred to as a first transparent substrate
  • a glass or film substrate sometimes referred to as a second transparent substrate
  • a photocurable resin layer 12 is formed on the hologram recording medium 1, and the hologram recording medium 1 has a three-layer structure.
  • the hologram recording medium of the present embodiment has high functionality, for example, has a high refractive index modulation amount ( ⁇ n), and is effective in excellent diffraction characteristics.
  • a coating liquid composed of the above-mentioned hologram recording composition is applied onto a transparent base material using a spin coater, a gravure coater, a comma coater, a bar coater, or the like, and then dried. It can be obtained, for example, by forming a photocurable resin layer.
  • the hologram of the present embodiment has high functionality, for example, has a high refractive index modulation amount ( ⁇ n), and has excellent diffraction characteristics.
  • the hologram recording medium described above is exposed to two light beams using a semiconductor laser in the visible light region, and then UV (ultraviolet rays) is irradiated over the entire surface to remove uncured monomers and the like. It can be obtained by curing and fixing the refractive index distribution to a hologram recording medium.
  • the conditions for the two luminous flux exposure may be appropriately set by those skilled in the art according to the use and purpose of the hologram, but preferably, the light intensity of one luminous flux on the hologram recording medium is 0.1 to 100 mW / cm 2. Therefore, it is desirable to perform exposure for 1 to 1000 seconds and perform interference exposure so that the angle formed by the two luminous fluxes is 0.1 to 179.9 degrees.
  • the optical device of the fourth embodiment according to the present technology is an device containing the organic material of the third embodiment according to the present technology. Since the optical device of the present embodiment contains the organic material of the third embodiment according to the present technology, it exhibits excellent optical characteristics and excellent optical stability.
  • the optical component of the fifth embodiment according to the present technology is a component containing the organic material of the third embodiment according to the present technology. Since the optical component of the present embodiment contains the organic material of the third embodiment according to the present technology, it exhibits excellent optical characteristics and excellent optical stability.
  • Examples of the optical device of the fourth embodiment according to the present technology and the optical component of the fifth embodiment according to the present technology include an image pickup device, an image pickup element, a color filter, a diffractive lens, a light guide plate, a spectroscopic element, and a hologram sheet.
  • Information recording media such as optical disks and magneto-optical disks, optical pickup devices, polarizing microscopes, sensors, and the like can be exemplified.
  • the image display device of the sixth embodiment according to the present technology is an apparatus containing the organic material of the third embodiment according to the present technology. Since the image display device of the present embodiment contains the organic material of the third embodiment according to the present technology, the effect of excellent image display performance is exhibited.
  • an image display device such as an eyewear, a holographic screen, a transparent display, a head-mounted display, and a head-up display can be exemplified.
  • composition of the seventh embodiment according to the present technology is a composition containing the compound of the first embodiment according to the present technology and a radically polymerizable monomer.
  • composition of the present embodiment has a high refractive index
  • it can be used as a high refractive index curing resin, for example, for an organic thin film, an organic lens, an optical film, a hologram, or the like.
  • any radically polymerizable monomer can be used.
  • monofunctional or polyfunctional carbazole-based monomers, dinaphthothiophene-based monomers, fluorene-based monomers, dibenzofuran-based monomers and the like can be mentioned, and one or more of these can be used.
  • Step A Step A of the synthesis method (synthesis route) shown above will be described. Under an inert atmosphere, 110 mL of an N, N-dimethylformamide (manufactured by Kanto Chemical Co., Inc.) solution mixed with 20 g of potassium hydroxide (manufactured by Kanto Chemical Co., Inc.) was prepared to prepare Compound 1 (7H-dibenzo [c, g] carbazole (Tokyo). (Manufactured by Kasei Kogyo Co., Ltd.)) 15 g was added and stirred for 1 hour, and then 25 g of 2-bromoethanol (manufactured by Tokyo Kasei Kogyo Co., Ltd.) was added and reacted for 20 hours. Water was added for quenching, extraction was performed with toluene using a separatory funnel, and column purification was performed to obtain 10 g of the target intermediate 1.
  • N, N-dimethylformamide manufactured by Kanto Chemical Co., Inc.
  • Step B Step B of the synthesis method (synthesis route) shown above will be described.
  • 9 g of Intermediate A was dissolved in a solution prepared by mixing 50 mL of methylene chloride (manufactured by Kanto Chemical Co., Inc.) with triethylamine (manufactured by Kanto Chemical Co., Inc.) and cooled in an ice bath.
  • 3 mL of acrylic chloride manufactured by Tokyo Chemical Industry Co., Ltd.
  • the C3 step of the compound synthesis method (synthesis route) represented by the chemical formula (10-1) is the same as the method represented by the C1 step of the compound synthesis method (synthesis route) represented by the chemical formula (6-8).
  • the compound represented by the chemical formula (10-1) was obtained by using various methods.
  • intermediate 10-1B was obtained by proceeding with the synthesis using the methods shown in the A3 step and the B3 step of the compound synthesis method (synthesis route) represented by the chemical formula (10-1).
  • the mixture was concentrated under reduced pressure, chloroform and water were added to the residue to separate the liquids.
  • the substance solidified by column purification and cooling is made into a slurry with a mixed solvent of heptane / ethyl acetate (manufactured by Tokyo Chemical Industry Co., Ltd.) and filtered. It was.
  • the crystals were washed with a mixed solvent of heptane / ethyl acetate, the obtained white solid was dissolved in chloroform, and 10 mL of 0.04 mg / mL phenothiazine-chloroform solution was added. Then, 1 g of the compound represented by the chemical formula (10-3) was obtained by concentrated drying.
  • step A6 of the compound synthesis method (synthesis route) represented by the chemical formula (10-4) was advanced using the method shown in step A6 of the compound synthesis method (synthesis route) represented by the chemical formula (10-4) to obtain intermediate 10-4A.
  • step A6 of the compound synthesis method (synthesis route) represented by the chemical formula (10-4) was proceeded using the method shown in step A6 of the compound synthesis method (synthesis route) represented by the chemical formula (10-4) to obtain intermediate 10-4A.
  • step A6 of the compound synthesis method (synthesis route) represented by the chemical formula (10-4) was carried out using the method shown in step A6 of the compound synthesis method (synthesis route) represented by the chemical formula (10-4) to obtain the intermediate 10-4A, and then the chemical formula (10-).
  • Intermediate 10-6B was obtained by proceeding with the synthesis using the method shown in step B8 of the compound synthesis method (synthesis route) represented by 6).
  • step A1 of the compound synthesis method represented by the chemical formula (6-8) to obtain the intermediate 2, and then the chemical formula (6-8).
  • the intermediate 3 was obtained by proceeding with the synthesis using the method shown in step B1 of the compound synthesis method (synthesis route) represented by.
  • A12 process The A12 step of the synthesis method (synthesis route) shown above will be described. Under an inert atmosphere, 230 mL of an aqueous sodium hydroxide solution (concentration 8.0 mol / L, manufactured by Fuji Film Wako Pure Chemical Industries, Ltd.), 8.5 g of tetrabutylammonium bromide (manufactured by Tokyo Chemical Industry Co., Ltd.), and 25 g of intermediate 3 are mixed. After cooling with ice water, 46 mL of 2- (2-chloroethoxy) tetrahydro-2H-pyran (manufactured by Tokyo Chemical Industry Co., Ltd.) was added.
  • 2- (2-chloroethoxy) tetrahydro-2H-pyran manufactured by Tokyo Chemical Industry Co., Ltd.
  • B12 process The B12 step of the synthesis method (synthesis route) shown above will be described.
  • a phenothiazine preparation solution was prepared by adding 10 mg of phenothiazine (manufactured by Tokyo Chemical Industry Co., Ltd.) to 50 mL of ultra-dehydrated tetrahydrofuran (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.).
  • the reaction solution was filtered, and 210 mL of ultra-dehydrated tetrahydrofuran, 1.1 g of 4-dimethylaminopyridine, and 7.3 mL of acrylic acid were mixed with the obtained filtrate. After cooling with ice water, 19 mL of N, N'-diisopropylcarbodiimide was added, and the mixture was returned to room temperature and stirred overnight. The reaction mixture is filtered, the filtrate is concentrated under reduced pressure, and then column purification is performed. 5.0 mL of the phenothiazine preparation solution is added to the obtained fraction and concentrated to dryness, which is represented by the chemical formula (10-10). 5.9 g of the compound was obtained.
  • step A1 of the compound synthesis method represented by the chemical formula (6-8) to obtain the intermediate 2, and then the chemical formula (6-8).
  • the intermediate 3 was obtained by proceeding with the synthesis using the method shown in step B1 of the compound synthesis method (synthesis route) represented by.
  • a phenothiazine preparation solution was prepared by adding 6.6 mg of phenothiazine (manufactured by Tokyo Chemical Industry Co., Ltd.) to 50 mL of ultra-dehydrated tetrahydrofuran (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.). In an inert atmosphere, 16 g of the intermediate 10-12C and 9 mL of the phenothiazine preparation solution are mixed, and 1.0 g of 4-dimethylaminopyridine (manufactured by Tokyo Chemical Industry) and 6.7 mL of acrylic acid (manufactured by Tokyo Chemical Industry) are added.
  • Acetone solution or chloroform solution of each compound of Test Examples 1 to 15 was prepared, and the average refractive index with respect to light at 589 nm at room temperature of 25 ⁇ 1 ° C. was measured with an Abbe refractive index meter (ER-1 manufactured by Elma Sales Co., Ltd.).
  • a calibration line was prepared by measuring and plotting against the volume fraction of each compound.
  • the density of each compound used was a value determined by a dry densitometer (Accupic II 1340-10CC (manufactured by Shimadzu Corporation)).
  • the calibration curve was extrapolated, and the refractive index when the volume fraction of each compound was 1, was defined as the refractive index of each compound.
  • the measurement results of the refractive index and density (g / cm 3 ) of each of the compounds of Test Examples 1 to 15 are shown in Table 1 below.
  • the compound of Test Example 1 (6-3), the compound of Test Example 2 (6-8), the compound of Test Example 3 (10-1) and the compound of Test Example 12 (10-10) have a refractive index of 1. Since it is as high as 75 or more, it can be suitably used as a high refractive index material. Further, the compound of Test Example 1 (6-3).
  • Compound of Test Example 2 (6-8), Compound of Test Example 3 (10-1), Compound of Test Example 4 (10-2), Compound of Test Example 5 (10-3), Compound of Test Example 6 ( 10-4), Compound of Test Example 7 (10-5), Compound of Test Example 8 (10-6), Compound of Test Example 9 (10-7), Compound of Test Example 10 (10-8), Test The refractive index of each of the compound of Example 11 (10-9), the compound of Test Example 12 (10-10), the compound of Test Example 13 (10-11) and the compound of Test Example 14 (10-12) was tested. It was higher than the refractive index of compound (11-1) of Example 15 and was good.
  • the solubility in an organic solvent is larger than 20 wt%.
  • the solubility in chloroform is larger than 20 wt%, it can be suitably used as a monomer material for holograms. Further, the compound (10-3) of Test Example 5 has a solubility in acetone and chloroform, which are general-purpose organic solvents, more than 20 wt%. Since it is large, it can be suitably used as a monomer material for holograms.
  • Example 1> (Preparation of composition 1 for hologram recording) According to the amounts shown in Table 2 below, the compound (6-3) of Test Example 1 and bisphenoxyethanol full orange acrylate (manufactured by Osaka Gas Chemical Co., Ltd., "EA-0200", refractive index: 1.62) as photopolymerizable monomers. , Polyvinyl acetate (manufactured by Electrochemical Industry Co., Ltd., "SN-77T”) as a binder resin, 1,6-hexanediol diglycidyl ether (manufactured by Nagase ChemteX Co., Ltd., "EX-212L”) as a plasticizer, sensitizing dye.
  • Rose Bengal manufactured by SIGMA ALDRICH, "RB”
  • 4-isopropyl-4'-methyldiphenyliodonium tetrakis (pentafluorophenyl) borate manufactured by Tokyo Kasei Kogyo Co., Ltd., "I0591”
  • chain transfer agent 2-Mercaptobenzoxazole manufactured by Tokyo Kasei Kogyo Co., Ltd., "2-MBO”
  • 2-MBO 2-Mercaptobenzoxazole
  • hologram recording medium 1 (Preparation of hologram recording medium 1)
  • the hologram recording composition 1 is applied onto a polyvinyl alcohol film having a thickness of 2.5 ⁇ m with a bar coater so that the dry film thickness is 3 ⁇ m, and then photocurable on a glass substrate having a thickness of 1.0 mm.
  • the thin film surface of the resin layer was pressure-bonded to obtain a hologram recording medium 1 formed by laminating a glass substrate, a photocurable resin layer, and a polyvinyl alcohol film in this order.
  • the hologram recording medium 1 is exposed to two light beams with an exposure amount of 180 mJ / cm 2 using a semiconductor laser having an exposure wavelength of 532 nm, and then the uncured monomer is cured by irradiating the entire surface with UV (ultraviolet rays). ,
  • the refractive index distribution was fixed to the medium 1.
  • the conditions for the two luminous flux exposure are that the light intensity of one luminous flux on the recording medium is 3.0 mW / cm 2 , the exposure is performed for 30 seconds, and the interference exposure is performed so that the angle formed by the two luminous fluxes is 5.0 degrees. It was.
  • a refractive index distribution was formed on the hologram recording medium 1, and the hologram 1 was obtained.
  • the refractive index modulation amount ( ⁇ n) is evaluated using Kogelnik's coupled wave theory (Bell System Technical Journal, 48, 2909 (1969)) from the maximum transmittance and full width at half maximum of the transmittance spectrum obtained by incident on the hologram. did.
  • the transmittance spectrum was obtained by measuring the transmittance at 400-700 nm using a spot light source manufactured by Hamamatsu Photonics Co., Ltd. as a light source and a small fiber optical spectroscope USB-4000 manufactured by Ocean Optics Co., Ltd. as a spectroscope.
  • Example 2 the same materials as in Example 1 were used except that the amount of the photopolymerizable monomer was changed as shown in Table 2, and for hologram recording in the same manner as in Example 1 according to the amount shown in Table 2. Composition 2 was obtained.
  • Example 3 the amounts of the photopolymerizable monomer and the chain transfer agent were changed as shown in Table 2, and Astrazone Orange G (manufactured by SIGMA ALDRICH, “AOG”) was used as the sensitizing dye as the polymerization initiator.
  • Astrazone Orange G manufactured by SIGMA ALDRICH, “AOG”
  • Example 4 the same materials as in Example 1 were used except that the amount of the photopolymerizable monomer was changed as shown in Table 2, and for hologram recording in the same manner as in Example 1 according to the amount shown in Table 2. Composition 4 was obtained.
  • Example 5 the amount of the photopolymerizable monomer was changed as shown in Table 2, and polyvinyl acetate (manufactured by Denki Kagaku Kogyo Co., Ltd., “SN-55T”) was used as the binder resin.
  • the hologram recording composition 5 was obtained in the same manner as in Example 1 according to the amounts shown in Table 2.
  • Example 6 the amount of the compound (6-3) which is a photopolymerizable monomer was changed as shown in Table 2, and the photopolymerizable monomer bisphenoxyethanol full orange acrylate (manufactured by Osaka Gas Chemical Co., Ltd., “ The same materials as in Example 1 were used except that the compound (10-3), which is a photopolymerizable monomer, was used in the amounts shown in Table 2 without using EA-020 ”, refractive index: 1.62). , The composition 6 for hologram recording was obtained in the same manner as in Example 1 according to the amounts shown in Table 2.
  • Example 7 the amount of the compound (6-3) which is a photopolymerizable monomer was changed as shown in Table 2, and the photopolymerizable monomer bisphenoxyethanol full orange acrylate (manufactured by Osaka Gas Chemical Co., Ltd., “ The same materials as in Example 1 were used except that the compound (10-2), which is a photopolymerizable monomer, was used in the amounts shown in Table 2 without using EA-020 ”, refractive index: 1.62). , The composition 7 for hologram recording was obtained in the same manner as in Example 1 according to the amounts shown in Table 2.
  • Example 8 the amount of the compound (6-3) which is a photopolymerizable monomer was changed as shown in Table 2, and the photopolymerizable monomer bisphenoxyethanol full orange acrylate (manufactured by Osaka Gas Chemical Co., Ltd., “ The same materials as in Example 1 were used except that the compound (10-10), which is a photopolymerizable monomer, was used in the amount shown in Table 2 without using EA-020 ”, refractive index: 1.62). , The composition 8 for hologram recording was obtained in the same manner as in Example 1 according to the amounts shown in Table 2.
  • Example 9 the amount of the compound (6-3) which is a photopolymerizable monomer was changed as shown in Table 2, and the photopolymerizable monomer bisphenoxyethanol full orange acrylate (manufactured by Osaka Gas Chemical Co., Ltd., “ The same materials as in Example 1 were used except that the compound (10-12), which is a photopolymerizable monomer, was used in the amount shown in Table 2 without using EA-020 ”, refractive index: 1.62). , The composition 9 for hologram recording was obtained in the same manner as in Example 1 according to the amounts shown in Table 2.
  • Example 10 the compound (6-3) which is a photopolymerizable monomer was not used, but the compound (10-8) which was a photopolymerizable monomer was used in the amount shown in Table 2, and the photopolymerizable monomer was used.
  • the same material as in Example 1 was used except that the amount of bisphenoxyethanol full orange acrylate (manufactured by Osaka Gas Chemical Co., Ltd., "EA-0200", refractive index: 1.62) was changed as shown in Table 2.
  • the composition 10 for hologram recording was obtained in the same manner as in Example 1 according to the amounts shown in Table 2.
  • Example 11 the compound (6-3) which is a photopolymerizable monomer and the bisphenoxyethanol full orange acrylate (manufactured by Osaka Gas Chemical Co., Ltd., “EA-0200”, refractive index: 1.62) which is a photopolymerizable monomer are used.
  • the same materials as in Example 1 were used and shown in Table 2, except that the photopolymerizable monomers, compound (10-8) and compound (10-10), were used in the amounts shown in Table 2.
  • the composition 11 for hologram recording was obtained in the same manner as in Example 1 according to the amount.
  • Example 12 the compound (6-3) which is a photopolymerizable monomer and the bisphenoxyethanol full orange acrylate (manufactured by Osaka Gas Chemical Co., Ltd., “EA-0200”, refractive index: 1.62) which is a photopolymerizable monomer are used.
  • the same materials as in Example 1 were used and are shown in Table 2, except that the photopolymerizable monomers, compound (10-8) and compound (10-12), were used in the amounts shown in Table 2.
  • the composition 12 for hologram recording was obtained in the same manner as in Example 1 according to the amount.
  • Example 13 the amount of the compound (6-3) which is a photopolymerizable monomer was changed as shown in Table 2, and the photopolymerizable monomer bisphenoxyethanol full orange acrylate (manufactured by Osaka Gas Chemical Co., Ltd., “ The same materials as in Example 1 were used except that the compound (10-11), which is a photopolymerizable monomer, was used in the amount shown in Table 2 without using EA-020 ”, refractive index: 1.62).
  • the hologram recording composition 13 was obtained in the same manner as in Example 1 according to the amounts shown in Table 2.
  • Comparative example 1 (Preparation of composition 101 for hologram recording)
  • the compound (11-1) ((2- (9H-carbazole-9-yl) ethyl acrylate (SIGMA ALDRICH) of Test Example 15) was used as a photopolymerizable monomer according to the amount shown in Table 2 below.
  • the same materials as in Example 1 were used, except that bisphenoxyethanol full orange acrylate (manufactured by Osaka Gas Chemical Co., Ltd., "EA-0200", refractive index: 1.62) was used.
  • a hologram recording composition 101 was obtained in the same manner as in Example 1 according to the amount shown in 2.
  • the hologram 101 was produced in the same manner as in Example 1 according to the exposure conditions shown in Table 2.
  • Comparative example 2 (Preparation of composition 102 for hologram recording)
  • the compound (11-1) ((2- (9H-carbazole-9-yl) ethyl acrylate (SIGMA ALDRICH) of Test Example 15) was used as a photopolymerizable monomer according to the amount shown in Table 2 below.
  • the same materials as in Example 1 were used, except that bisphenoxyethanol full orange acrylate (manufactured by Osaka Gas Chemical Co., Ltd., "EA-0200", refractive index: 1.62) was used.
  • a hologram recording composition 102 was obtained in the same manner as in Example 1 according to the amount shown in 2.
  • Table 2 shows the experimental results of the holograms of Examples 1 to 13 and Comparative Examples 1 and 2 described above. In Table 2, the numerical value of each component is shown in mass%.
  • a compound represented by the following general formula (1) A compound represented by the following general formula (1).
  • X 1 is an oxygen atom, a nitrogen atom, a phosphorus atom, a carbon atom or a silicon atom. If X 1 is an oxygen atom, a is 0, if X 1 is a nitrogen or phosphorus atom, a is 1, and if X 1 is a carbon or silicon atom, a is 2. ..
  • Y 1 and Y 2 are benzene rings or naphthalene rings, respectively, and Y 1 and Y 2 are not benzene rings at the same time.
  • R 1 to R 3 are hydrogen or substituents represented by * -Z 1 (R 4 ) d (* represents a bond position), respectively.
  • R 1 ⁇ R 3 is present in plural, a plurality of R 1 ⁇ R 3 may be the being the same or different, but the general formula (1) all R 1 ⁇ R 3 in It cannot be hydrogen at the same time.
  • Z 1 represents a monobond, a divalent or higher saturated hydrocarbon group or a divalent or higher unsaturated hydrocarbon group, and the saturated hydrocarbon group or unsaturated hydrocarbon group may contain an ether bond and / or a thioether bond. .. If Z 1 is a single bond, d is 1, and if Z 1 is a saturated or unsaturated hydrocarbon group, d is an integer greater than or equal to 1.
  • R 4 represents hydrogen or a polymerizable substituent. If R 4 there are a plurality, the plurality of R 4 may be independently identical or different from each other, but not all of R 4 in the general formula (1) are simultaneously hydrogen. [2] The compound according to [1], wherein X 1 of the general formula (1) is a nitrogen atom.
  • R 1 , R 21 to R 26 , and R 31 to R 36 are hydrogen or substitutions represented by * -Z 1 (R 4 ) d (* represents a bond position). Is the basis. R 1 , R 21 to R 26 , and R 31 to R 36 may be the same or different from each other. However, R 1 , R 21 to R 26 , and R 31 to R 36 in the general formula (1-1) are not all hydrogen at the same time.
  • Z 1 represents a monobond, a divalent or higher saturated hydrocarbon group or a divalent or higher unsaturated hydrocarbon group, and the saturated hydrocarbon group or unsaturated hydrocarbon group may contain an ether bond and / or a thioether bond. .. If Z 1 is a single bond, d is 1, and if Z 1 is a saturated or unsaturated hydrocarbon group, d is an integer greater than or equal to 1.
  • R 4 represents hydrogen or a polymerizable substituent. If R 4 there are a plurality, the plurality of R 4 may be independently identical or different from each other, but not the general formula (1-1) all R 4 in are hydrogen at the same time.
  • R 21 to R 26 and R 31 to R 36 are all hydrogen.
  • [7] A polymer obtained by polymerizing the compound according to any one of [1] to [3].
  • the organic material according to [8] which is a composition for an organic thin film, a composition for an organic lens, or a photosensitive composition for hologram recording.
  • An optical device comprising the organic material according to [4].
  • An optical device comprising the organic material according to [8].
  • composition according to [17], wherein the radically polymerizable monomer is at least one selected from a carbazole-based monomer, a dinaphthophene-based monomer, a fluorene-based monomer, and a dibenzofuran-based monomer.

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PCT/JP2020/024149 2019-07-08 2020-06-19 化合物、ポリマー及び有機材料、並びにこれを用いた光学装置、光学部品及び画像表示装置 Ceased WO2021006011A1 (ja)

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