WO2021131355A1 - 樹脂組成物、硬化物、紫外線吸収剤、紫外線カットフィルタ、レンズ、保護材、化合物及び化合物の合成方法 - Google Patents
樹脂組成物、硬化物、紫外線吸収剤、紫外線カットフィルタ、レンズ、保護材、化合物及び化合物の合成方法 Download PDFInfo
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- WO2021131355A1 WO2021131355A1 PCT/JP2020/041670 JP2020041670W WO2021131355A1 WO 2021131355 A1 WO2021131355 A1 WO 2021131355A1 JP 2020041670 W JP2020041670 W JP 2020041670W WO 2021131355 A1 WO2021131355 A1 WO 2021131355A1
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- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
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Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/22—Absorbing filters
- G02B5/223—Absorbing filters containing organic substances, e.g. dyes, inks or pigments
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/45—Heterocyclic compounds having sulfur in the ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L101/00—Compositions of unspecified macromolecular compounds
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- 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
- C09D125/00—Coating compositions based on homopolymers or 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 an aromatic carbocyclic ring; Coating compositions based on derivatives of such polymers
- C09D125/02—Homopolymers or copolymers of hydrocarbons
- C09D125/04—Homopolymers or copolymers of styrene
- C09D125/08—Copolymers of styrene
- C09D125/12—Copolymers of styrene with unsaturated nitriles
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- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F21—LIGHTING
- F21V—FUNCTIONAL FEATURES OR DETAILS OF LIGHTING DEVICES OR SYSTEMS THEREOF; STRUCTURAL COMBINATIONS OF LIGHTING DEVICES WITH OTHER ARTICLES, NOT OTHERWISE PROVIDED FOR
- F21V9/00—Elements for modifying spectral properties, polarisation or intensity of the light emitted, e.g. filters
- F21V9/06—Elements for modifying spectral properties, polarisation or intensity of the light emitted, e.g. filters for filtering out ultraviolet radiation
-
- 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
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/208—Filters for use with infrared or ultraviolet radiation, e.g. for separating visible light from infrared and/or ultraviolet radiation
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/005—Stabilisers against oxidation, heat, light, ozone
Definitions
- the present invention relates to a resin composition. More specifically, it relates to a resin composition containing a benzodithiol compound.
- the present invention also relates to a cured product, an ultraviolet absorber, an ultraviolet cut filter, a lens, a protective material, a compound, and a method for synthesizing a compound.
- the benzodithiol compound has excellent ultraviolet absorption and is used as an ultraviolet absorber.
- Patent Document 1 describes that a specific benzodithiol compound is used as an ultraviolet absorber.
- UV absorbers One of the required properties of UV absorbers is that they are less colored. Further, in recent years, it has been required to have a high absorption capacity for ultraviolet rays having a longer wavelength near 400 nm.
- an object of the present invention is the synthesis of a resin composition, a cured product, an ultraviolet absorber, an ultraviolet cut filter, a lens, a protective material, a compound, and a compound capable of producing a cured product having an excellent ability to absorb ultraviolet rays in the vicinity of a wavelength of 400 nm. To provide a method.
- a resin composition containing the compound represented by the formula (1) and a resin In formula (1), R 1 and R 2 independently represent an alkyl group, an aryl group or a heterocyclic group, respectively. R 3 and R 6 independently represent an alkoxy group, an acyloxy group, a carbamoyloxy group or an alkoxycarbonyloxy group, respectively.
- R 4 represents an alkyl group, an aryl group, an alkoxy group, an aryloxy group, an acyloxy group, an alkylamino group, an anilino group, an acylamino group, an alkylsulfonylamino group, an arylsulfonylamino group, an alkylthio group or an arylthio group.
- R 5 represents a hydrogen atom, an alkyl group, an aryl group, an alkoxy group, an aryloxy group, an acyloxy group, an alkylamino group, an anilino group, an acylamino group, an alkylsulfonylamino group, an arylsulfonylamino group, an alkylthio group or an arylthio group.
- R 1 and R 2 may be combined with each other to form a ring;
- R 3 and R 4 may combine with each other to form a ring;
- R 4 and R 5 may combine with each other to form a ring;
- R 5 and R 6 may combine with each other to form a ring;
- R 3 and R 6 are independently acyloxy groups or carbamoyloxy groups
- at least one of R 4 and R 5 is an aryl group, an alkoxy group, an aryloxy group, an acyloxy group, an alkylamino group, an anilino group, and the like.
- R 4 is an alkyl group, an aryl group, an alkoxy group or an aryloxy group
- R 5 is a hydrogen atom, an alkyl group, an aryl group, an alkoxy group or an aryloxy group, ⁇ 1.
- the resin composition according to. ⁇ 3> The resin composition according to ⁇ 1> or ⁇ 2>, wherein at least one of R 3 and R 6 is an alkoxy group in the formula (1).
- R 4a represents an alkyl group or an alkoxy group and represents R 5a represents a hydrogen atom, an alkyl group or an alkoxy group
- R 1a and R 2a may be coupled to each other to form a ring
- R 3a and R 4a may be coupled to each other to form a ring
- R 4a and R 5a may be coupled to each other to form a ring
- R 5a and R 6a may be coupled to each other to form a ring
- R 3a and R 6a are acyloxy groups
- at least one of R 4a and R 5a is an alkoxy group.
- R 11 and R 12 independently represent an alkyl group, an aryl group or a heterocyclic group, respectively.
- R 13 and R 16 independently represent a hydroxy group, an alkoxy group, an aryloxy group, an acyloxy group, a carbamoyloxy group, an alkoxycarbonyloxy group, an aryloxycarbonyloxy group, a sulfinyloxy group or a sulfonyloxy group, respectively.
- R 14 represents an alkyl group, an aryl group, an alkoxy group, an aryloxy group, an acyloxy group, an alkylamino group, an anirino group, an acylamino group, an alkylsulfonylamino group, an arylsulfonylamino group, an alkylthio group or an arylthio group.
- R 15 represents a hydrogen atom, an alkyl group, an aryl group, an alkoxy group, an aryloxy group, an acyloxy group, an alkylamino group, an anilino group, an acylamino group, an alkylsulfonylamino group, an arylsulfonylamino group, an alkylthio group or an arylthio group;
- R 11 and R 12 may be combined with each other to form a ring;
- R 13 and R 14 may be combined with each other to form a ring;
- R 14 and R 15 may combine with each other to form a ring;
- R 15 and R 16 may combine with each other to form a ring;
- at least one of R 13 and R 16 is a hydroxy group.
- the above resin is at least one selected from (meth) acrylic resin, polystyrene resin, polyester resin, polyurethane resin, polythiourethane resin, polyimide resin, epoxy resin, polycarbonate resin and cellulose acylate resin.
- ⁇ 8> A cured product obtained by using the resin composition according to any one of ⁇ 1> to ⁇ 7>.
- R 1 and R 2 independently represent an alkyl group, an aryl group or a heterocyclic group, respectively.
- R 3 and R 6 independently represent an alkoxy group, an acyloxy group, a carbamoyloxy group or an alkoxycarbonyloxy group, respectively.
- R 4 represents an alkyl group, an aryl group, an alkoxy group, an aryloxy group, an acyloxy group, an alkylamino group, an anilino group, an acylamino group, an alkylsulfonylamino group, an arylsulfonylamino group, an alkylthio group or an arylthio group.
- R 5 represents a hydrogen atom, an alkyl group, an aryl group, an alkoxy group, an aryloxy group, an acyloxy group, an alkylamino group, an anilino group, an acylamino group, an alkylsulfonylamino group, an arylsulfonylamino group, an alkylthio group or an arylthio group.
- R 1 and R 2 may be combined with each other to form a ring;
- R 3 and R 4 may combine with each other to form a ring;
- R 4 and R 5 may combine with each other to form a ring;
- R 5 and R 6 may combine with each other to form a ring;
- R 3 and R 6 are independently acyloxy groups or carbamoyloxy groups
- at least one of R 4 and R 5 is an aryl group, an alkoxy group, an aryloxy group, an acyloxy group, an alkylamino group, an anilino group, and the like.
- the ultraviolet absorber according to ⁇ 9> further comprising a compound represented by the formula (2);
- R 11 and R 12 independently represent an alkyl group, an aryl group or a heterocyclic group, respectively.
- R 13 and R 16 independently represent a hydroxy group, an alkoxy group, an aryloxy group, an acyloxy group, a carbamoyloxy group, an alkoxycarbonyloxy group, an aryloxycarbonyloxy group, a sulfinyloxy group or a sulfonyloxy group, respectively.
- R 14 represents an alkyl group, an aryl group, an alkoxy group, an aryloxy group, an acyloxy group, an alkylamino group, an anirino group, an acylamino group, an alkylsulfonylamino group, an arylsulfonylamino group, an alkylthio group or an arylthio group.
- R 15 represents a hydrogen atom, an alkyl group, an aryl group, an alkoxy group, an aryloxy group, an acyloxy group, an alkylamino group, an anilino group, an acylamino group, an alkylsulfonylamino group, an arylsulfonylamino group, an alkylthio group or an arylthio group;
- R 11 and R 12 may be combined with each other to form a ring;
- R 13 and R 14 may be combined with each other to form a ring;
- R 14 and R 15 may combine with each other to form a ring;
- R 15 and R 16 may combine with each other to form a ring;
- at least one of R 13 and R 16 is a hydroxy group.
- R 1a and R 2a each independently represent an alkyl group.
- R 3a and R 6a independently represent an alkoxy group or an acyloxy group, respectively.
- R 4a represents an alkyl group or an alkoxy group and represents R 5a represents a hydrogen atom, an alkyl group or an alkoxy group
- R 1a and R 2a may be coupled to each other to form a ring
- R 3a and R 4a may be coupled to each other to form a ring
- R 4a and R 5a may be coupled to each other to form a ring
- R 5a and R 6a may be coupled to each other to form a ring
- R 3a and R 6a are acyloxy groups
- at least one of R 4a and R 5a is an alkoxy group.
- R 1a and R 2a each independently represent an alkyl group.
- R 3a and R 6a independently represent an alkoxy group or an acyloxy group, respectively.
- R 4a represents an alkyl group or an alkoxy group and represents R 5a represents a hydrogen atom, an alkyl group or an alkoxy group
- R 1a and R 2a may be coupled to each other to form a ring
- R 3a and R 4a may be coupled to each other to form a ring
- R 4a and R 5a may be coupled to each other to form a ring
- R 5a and R 6a may be coupled to each other to form a ring
- R 11a and R 12a each independently represent an alkyl group.
- R 14a represents an alkyl group or an alkoxy group.
- R 15a represents a hydrogen atom, an alkyl group or an alkoxy group;
- R 14a and R 15a may be coupled to each other to form a ring.
- a resin composition, a cured product, an ultraviolet absorber, an ultraviolet cut filter, a lens, a protective material, a compound, and a method for synthesizing a compound capable of producing a cured product having an excellent ability to absorb ultraviolet rays in the vicinity of a wavelength of 400 nm can be obtained.
- FIG. 5 is a schematic view showing a configuration in which an ultraviolet absorber of the present invention is added to a polarizing plate protective film on the front side, which is an embodiment of a liquid crystal display device.
- FIG. 5 is a schematic view showing a configuration in which an ultraviolet absorber of the present invention is added to a polarizing plate protective film on the backlight side according to an embodiment of a liquid crystal display device.
- FIG. 5 is a schematic view showing a configuration in which an ultraviolet absorber of the present invention is added to an inner protective film on the front side, which is an embodiment of a liquid crystal display device.
- FIG. 5 is a schematic view showing a configuration in which an ultraviolet absorber of the present invention is added to an inner protective film on the backlight side, which is an embodiment of a liquid crystal display device.
- FIG. 5 is a schematic view showing a configuration in which an optical film containing an ultraviolet absorber of the present invention is attached to a retardation film on the front side via an adhesive or an adhesive, which is an embodiment of a liquid crystal display device.
- FIG. 5 is a schematic view showing a configuration in which an optical film containing an ultraviolet absorber of the present invention is bonded to a retardation film on the backlight side via an adhesive or an adhesive, which is an embodiment of a liquid crystal display device.
- FIG. 5 is a schematic view showing a configuration in which an optical film containing an ultraviolet absorber of the present invention is bonded to a retardation film on the backlight side via an adhesive or an adhesive, which is an embodiment of a liquid crystal display device.
- FIG. 5 is a schematic view showing a configuration in which an ultraviolet absorber of the present invention is added to an adhesive or an adhesive on the front side according to an embodiment of a liquid crystal display device.
- FIG. 5 is a schematic view showing a configuration in which an ultraviolet absorber of the present invention is added to an adhesive or an adhesive on the backlight side, which is an embodiment of a liquid crystal display device.
- FIG. 5 is a schematic view showing a configuration in which an ultraviolet absorber of the present invention is added to a functional layer on the front side, which is an embodiment of a liquid crystal display device.
- FIG. 5 is a schematic view showing a configuration in which an ultraviolet absorber of the present invention is added to a functional layer on the backlight side, which is an embodiment of a liquid crystal display device.
- FIG. 5 is a schematic view showing a configuration in which an ultraviolet absorber of the present invention is added to a functional layer on the backlight side, which is an embodiment of a liquid crystal display device.
- FIG. 5 is a schematic view showing a configuration in which an ultraviolet absorber of the present invention is added to a polarizing plate protective film, which is an embodiment of an organic electroluminescence display device.
- FIG. 5 is a schematic view showing a configuration in which an ultraviolet absorber of the present invention is added to an adhesive or an adhesive, which is an embodiment of an organic electroluminescence display device.
- FIG. 5 is a schematic view showing a configuration in which an optical film containing an ultraviolet absorber of the present invention is attached to a touch panel via an adhesive or an adhesive, which is an embodiment of an organic electroluminescence display device.
- the notation not describing substitution and non-substituent includes a group having a substituent as well as a group having no substituent.
- the "alkyl group” includes not only an alkyl group having no substituent (unsubstituted alkyl group) but also an alkyl group having a substituent (substituted alkyl group).
- the numerical range represented by using "-" in the present specification means a range including the numerical values before and after "-" as the lower limit value and the upper limit value.
- the total solid content means the total amount of the components excluding the solvent from all the components of the resin composition.
- (meth) acrylate represents both acrylate and methacrylate, or either, and “(meth) acrylic” represents both acrylic and methacrylic, or either.
- Allyl represents both allyl and methacrylic, or either, and“ (meth) acryloyl ”represents both acryloyl and methacrylic acid, or either.
- process not only means an independent process, but also the term “process” as long as the intended action of the process is achieved even if it cannot be clearly distinguished from other processes. include.
- the weight average molecular weight (Mw) and the number average molecular weight (Mn) are defined as polystyrene-equivalent values measured by gel permeation chromatography (GPC).
- the resin composition of the present invention is characterized by containing a compound represented by the formula (1) and a resin.
- the compound represented by the formula (1) is a compound having an excellent ability to absorb ultraviolet rays in the vicinity of a wavelength of 400 nm and having little coloring. Therefore, the resin composition of the present invention can produce a cured product having an excellent ability to absorb ultraviolet rays in the vicinity of a wavelength of 400 nm. Further, the compound represented by the formula (1) has good compatibility with a resin or the like, and can suppress surface unevenness on the surface of the cured product.
- the resin composition of the present invention contains a compound represented by the formula (1) (hereinafter, also referred to as compound (1)).
- R 1 and R 2 independently represent an alkyl group, an aryl group or a heterocyclic group, respectively.
- R 3 and R 6 independently represent an alkoxy group, an acyloxy group, a carbamoyloxy group or an alkoxycarbonyloxy group, respectively.
- R 4 represents an alkyl group, an aryl group, an alkoxy group, an aryloxy group, an acyloxy group, an alkylamino group, an anilino group, an acylamino group, an alkylsulfonylamino group, an arylsulfonylamino group, an alkylthio group or an arylthio group.
- R 5 represents a hydrogen atom, an alkyl group, an aryl group, an alkoxy group, an aryloxy group, an acyloxy group, an alkylamino group, an anilino group, an acylamino group, an alkylsulfonylamino group, an arylsulfonylamino group, an alkylthio group or an arylthio group.
- R 1 and R 2 may be combined with each other to form a ring;
- R 3 and R 4 may combine with each other to form a ring;
- R 4 and R 5 may combine with each other to form a ring;
- R 5 and R 6 may combine with each other to form a ring;
- R 3 and R 6 are independently acyloxy groups or carbamoyloxy groups
- at least one of R 4 and R 5 is an aryl group, an alkoxy group, an aryloxy group, an acyloxy group, an alkylamino group, an anilino group, and the like. It is an acylamino group, an alkylsulfonylamino group, an arylsulfonylamino group, an alkylthio group or an arylthio group.
- R 1 and R 2 independently represent an alkyl group, an aryl group or a heterocyclic group, respectively, and are preferably an alkyl group or an aryl group. From the viewpoint of light resistance, it is preferable that R 1 and R 2 are independently alkyl groups. Further, from the viewpoint of absorption of ultraviolet rays having a wavelength near 400 nm, it is preferable that R 1 and R 2 are independently aryl groups.
- the number of carbon atoms of the alkyl group represented by R 1 and R 2 is preferably 1 to 30, more preferably 1 to 20, further preferably 1 to 15, particularly preferably 1 to 10, and most preferably 1 to 8.
- the alkyl group may be linear, branched or cyclic, preferably linear or branched.
- the alkyl group may have a substituent. Examples of the substituent include the group described in Substituent T described later.
- the aryl group represented by R 1 and R 2 preferably has 6 to 40 carbon atoms, more preferably 6 to 30 carbon atoms, further preferably 6 to 20 carbon atoms, particularly preferably 6 to 15 carbon atoms, and most preferably 6 to 12 carbon atoms.
- a phenyl group and a naphthyl group are preferable, and a phenyl group is more preferable.
- the aryl group may have a substituent. Examples of the substituent include the group described in Substituent T described later.
- the heterocycle in the heterocyclic group represented by R 1 and R 2 preferably contains a 5- or 6-membered saturated or unsaturated heterocycle.
- the heterocycle may be fused with an aliphatic ring, an aromatic ring or another heterocycle.
- Examples of the heteroatom constituting the ring of the heterocycle include B, N, O, S, Se and Te, and N, O and S are preferable.
- the carbon atom of the heterocycle has a free valence (monovalent) (the heterocyclic group is bonded at the carbon atom).
- the preferred heterocyclic group has 1 to 40 carbon atoms, more preferably 1 to 30, and even more preferably 1 to 20.
- Examples of saturated heterocycles in the heterocyclic group include pyrrolidine ring, morpholine ring, 2-bora-1,3-dioxolane ring and 1,3-thiazolidine ring.
- Examples of the unsaturated heterocycle in the heterocyclic group include an imidazole ring, a thiazole ring, a benzothiazole ring, a benzoxazole ring, a benzotriazole ring, a benzoselenazole ring, a pyridine ring, a pyrimidine ring and a quinoline ring.
- the heterocyclic group may have a substituent. Examples of the substituent include the group described in Substituent T described later.
- R 1 and R 2 may be combined with each other to form a ring.
- the ring formed by combining R 1 and R 2 is preferably a 5-membered or 6-membered ring.
- the ring formed by combining R 1 and R 2 may have a substituent. Examples of the substituent include the group described in Substituent T described later.
- R 3 and R 6 each independently represent an alkoxy group, an acyloxy group, a carbamoyloxy group or an alkoxycarbonyloxy group, preferably an alkoxy group or an acyloxy group, and have a wavelength while suppressing coloring. It is more preferable that at least one of R 3 and R 6 is an alkoxy group because it is easier to increase the absorption of ultraviolet rays in the vicinity of 400 nm. According to the study by the present inventor, it has been found that the higher the electron donating ability of the substituent on the benzene ring of benzodithiol, the easier it is to shift the maximum absorption wavelength of the compound to the longer wavelength side. Since the alkoxy group is a substituent having a higher electron donating ability, it is presumed that the maximum absorption wavelength of the compound could be shifted to the longer wavelength side. It is particularly preferred that both R 3 and R 6 are alkoxy groups.
- the number of carbon atoms of the alkoxy group represented by R 3 and R 6 is preferably 1 to 30, more preferably 1 to 20, further preferably 1 to 15, particularly preferably 1 to 10, and most preferably 1 to 8.
- the alkoxy group may be linear or branched.
- the alkoxy group may have a substituent. Examples of the substituent include the group described in Substituent T described later.
- the number of carbon atoms of the acyloxy group represented by R 3 and R 6 is preferably 2 to 30, more preferably 2 to 20, further preferably 2 to 15, and particularly preferably 2 to 10.
- the acyloxy group may have a substituent. Examples of the substituent include the group described in Substituent T described later.
- the carbon number of the carbamoyloxy group represented by R 3 and R 6 is preferably 2 to 30, more preferably 2 to 20, further preferably 2 to 15, particularly preferably 2 to 10, and most preferably 2 to 8.
- the carbamoyloxy group may be linear or branched.
- the carbamoyloxy group may have a substituent. Examples of the substituent include the group described in Substituent T described later.
- the number of carbon atoms of the alkoxycarbonyloxy group represented by R 3 and R 6 is preferably 2 to 30, more preferably 2 to 20, further preferably 2 to 15, particularly preferably 2 to 10, and most preferably 2 to 8.
- the alkoxycarbonyloxy group may be linear or branched.
- the alkoxycarbonyloxy group may have a substituent. Examples of the substituent include the group described in Substituent T described later.
- R 4 is an alkyl group, an aryl group, an alkoxy group, an aryloxy group, an acyloxy group, an alkylamino group, an anirino group, an acylamino group, an alkylsulfonylamino group, an arylsulfonylamino group, an alkylthio group or an arylthio group.
- R 5 is a hydrogen atom, an alkyl group, an aryl group, an alkoxy group, an aryloxy group, an acyloxy group, an alkylamino group, an anilino group, an acylamino group, alkylsulfonylamino group, arylsulfonylamino group, an alkylthio group or an Represents an arylthio group.
- the number of carbon atoms of the alkyl group represented by R 4 and R 5 is preferably 1 to 30, more preferably 1 to 20, further preferably 1 to 15, particularly preferably 1 to 10, and most preferably 1 to 8.
- the alkyl group may be linear, branched or cyclic, preferably linear or branched.
- the alkyl group may have a substituent. Examples of the substituent include the group described in Substituent T described later.
- the aryl group represented by R 4 and R 5 preferably has 6 to 40 carbon atoms, more preferably 6 to 30 carbon atoms, further preferably 6 to 20 carbon atoms, particularly preferably 6 to 15 carbon atoms, and most preferably 6 to 12 carbon atoms.
- a phenyl group and a naphthyl group are preferable, and a phenyl group is more preferable.
- the aryl group may have a substituent. Examples of the substituent include the group described in Substituent T described later.
- the number of carbon atoms of the alkoxy group represented by R 4 and R 5 is preferably 1 to 30, more preferably 1 to 20, further preferably 1 to 15, particularly preferably 1 to 10, and most preferably 1 to 8.
- the alkoxy group may be linear or branched.
- the alkoxy group may have a substituent. Examples of the substituent include the group described in Substituent T described later.
- the aryloxy group represented by R 4 and R 5 preferably has 6 to 40 carbon atoms, more preferably 6 to 30 carbon atoms, further preferably 6 to 20 carbon atoms, particularly preferably 6 to 15 carbon atoms, and most preferably 6 to 12 carbon atoms.
- the aryloxy group may have a substituent. Examples of the substituent include the group described in Substituent T described later.
- the number of carbon atoms of the anilino group represented by R 4 and R 5 is preferably 6 to 40, more preferably 6 to 30, further preferably 6 to 20, particularly preferably 6 to 15, and most preferably 6 to 12.
- the anilino group may have a substituent. Examples of the substituent include the group described in Substituent T described later.
- the number of carbon atoms of the acylamino group represented by R 4 and R 5 is preferably 2 to 30, more preferably 2 to 20, further preferably 2 to 15, and particularly preferably 2 to 10.
- the acylamino group may have a substituent. Examples of the substituent include the group described in Substituent T described later.
- the number of carbon atoms of the alkylsulfonylamino group represented by R 4 and R 5 is preferably 2 to 30, more preferably 2 to 20, further preferably 2 to 15, and particularly preferably 2 to 10.
- the alkylsulfonylamino group may have a substituent. Examples of the substituent include the group described in Substituent T described later.
- the arylsulfonylamino group represented by R 4 and R 5 preferably has 6 to 40 carbon atoms, more preferably 6 to 30 carbon atoms, further preferably 6 to 20 carbon atoms, particularly preferably 6 to 15 carbon atoms, and most preferably 6 to 12 carbon atoms.
- the arylsulfonylamino group may have a substituent. Examples of the substituent include the group described in Substituent T described later.
- the number of carbon atoms of the alkylthio group represented by R 4 and R 5 is preferably 1 to 30, more preferably 1 to 20, further preferably 1 to 15, particularly preferably 1 to 10, and most preferably 1 to 8.
- the alkylthio group may be linear or branched.
- the alkylthio group may have a substituent. Examples of the substituent include the group described in Substituent T described later.
- the number of carbon atoms of the arylthio group represented by R 4 and R 5 is preferably 6 to 40, more preferably 6 to 30, further preferably 6 to 20, particularly preferably 6 to 15, and most preferably 6 to 12.
- the arylthio group may have a substituent. Examples of the substituent include the group described in Substituent T described later.
- R 3 and R 4 may be bonded to each other to form a ring
- R 4 and R 5 may be bonded to each other to form a ring
- R 5 and R 6 may be bonded to each other to form a ring. They may be combined with each other to form a ring.
- the ring formed by bonding these groups to each other is preferably a 5-membered or 6-membered ring.
- the ring formed by bonding these groups to each other may have a substituent. Examples of the substituent include the group described in Substituent T described later.
- R 4 is an alkyl group, an aryl group, an alkoxy group or an aryloxy group
- R 5 is a hydrogen atom, an alkyl group, an aryl group, because it is easier to enhance the absorption of ultraviolet rays in the vicinity of a wavelength of 400 nm while suppressing coloring. It is preferably an alkoxy group or an aryloxy group, more preferably R 4 is an alkyl group or an alkoxy group, and R 5 is a hydrogen atom, an alkyl group or an alkoxy group.
- R 4 is preferably an alkyl group, an aryl group, an alkoxy group or an aryloxy group
- R 5 is preferably a hydrogen atom
- R 4 is an alkyl group or an alkoxy group
- R 5 Is more preferably a hydrogen atom
- R 4 and R 5 are preferably alkyl groups, aryl groups, alkoxy groups or aryloxy groups, respectively, and more preferably alkyl groups or alkoxy groups. , R 4 and R 5 are both alkyl groups, or both R 4 and R 5 are more preferably alkoxy groups.
- R 4 and R 5 are bonded to each other to form a ring.
- R 3 and R 6 are acyloxy groups
- at least one of R 4 and R 5 is an aryl group, an alkoxy group, an aryloxy group, an acyloxy group, an alkylamino group, anilino group or an acylamino group.
- the compound represented by the formula (1) is preferably a compound represented by the following formula (1a).
- R 1a and R 2a each independently represent an alkyl group.
- R 3a and R 6a independently represent an alkoxy group or an acyloxy group, respectively.
- R 4a represents an alkyl group or an alkoxy group and represents R 5a represents a hydrogen atom, an alkyl group or an alkoxy group
- R 1a and R 2a may be coupled to each other to form a ring
- R 3a and R 4a may be coupled to each other to form a ring
- R 4a and R 5a may be coupled to each other to form a ring
- R 5a and R 6a may be coupled to each other to form a ring
- R 3a and R 6a are acyloxy groups
- at least one of R 4a and R 5a is an alkoxy group.
- the number of carbon atoms of the alkyl group represented by R 1a and R 2a is preferably 1 to 30, more preferably 1 to 20, further preferably 1 to 15, particularly preferably 1 to 10, and most preferably 1 to 8.
- the alkyl group may be linear, branched or cyclic, preferably linear or branched.
- the alkyl group may have a substituent. Examples of the substituent include the group described in Substituent T described later.
- R 1a and R 2a may be coupled to each other to form a ring.
- the ring formed by combining R 1a and R 2a is preferably a 5-membered or 6-membered ring.
- the ring formed by combining R 1a and R 2a may have a substituent. Examples of the substituent include the group described in Substituent T described later.
- R 3a and R 6a are each independently represents an alkoxy group or an acyloxy group, while suppressing the coloration, because it further increased easily absorbable ultraviolet wavelength of around 400nm of R 3a and R 6a At least one is preferably an alkoxy group, and more preferably both R 3a and R 6a are alkoxy groups.
- the alkoxy group represented by R 3a and R 6a has preferably 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, further preferably 1 to 15 carbon atoms, particularly preferably 1 to 10 carbon atoms, and most preferably 1 to 8 carbon atoms.
- the alkoxy group may be linear or branched.
- the alkoxy group may have a substituent. Examples of the substituent include the group described in Substituent T described later.
- the number of carbon atoms of the acyloxy group represented by R 3a and R 6a is preferably 2 to 30, more preferably 2 to 20, further preferably 2 to 15, and particularly preferably 2 to 10.
- the acyloxy group may have a substituent. Examples of the substituent include the group described in Substituent T described later.
- R 4a represents an alkyl group or an alkoxy group
- R 5a represents a hydrogen atom, an alkyl group or an alkoxy group
- the number of carbon atoms of the alkyl group represented by R 4a and R 5a is preferably 1 to 30, more preferably 1 to 20, further preferably 1 to 15, particularly preferably 1 to 10, and most preferably 1 to 8.
- the alkyl group may be linear, branched or cyclic, preferably linear or branched.
- the alkyl group may have a substituent. Examples of the substituent include the group described in Substituent T described later.
- the alkoxy group represented by R 4a and R 5a has preferably 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, further preferably 1 to 15 carbon atoms, particularly preferably 1 to 10 carbon atoms, and most preferably 1 to 8 carbon atoms.
- the alkoxy group may be linear or branched.
- the alkoxy group may have a substituent. Examples of the substituent include the group described in Substituent T described later.
- R 3a and R 4a may be coupled to each other to form a ring
- R 4a and R 5a may be coupled to each other to form a ring
- R 5a and R 6a may be coupled to each other to form a ring. They may be combined with each other to form a ring.
- the ring formed by bonding these groups to each other is preferably a 5-membered or 6-membered ring.
- the ring formed by bonding these groups to each other may have a substituent. Examples of the substituent include the group described in Substituent T described later.
- substituent T examples include the following groups.
- Halogen atom eg chlorine atom, bromine atom, iodine atom
- Alkylation group [straight, branched, cyclic alkyl group.
- a linear or branched alkyl group preferably a linear or branched alkyl group having 1 to 30 carbon atoms, for example, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, a t-butyl group, n.
- cycloalkyl group preferably cycloalkyl group having 3 to 30 carbon atoms, for example, cyclohexyl group, cyclopentyl group, 4- n-dodecylcyclohexyl group
- bicycloalkyl group preferably a bicycloalkyl group having 5 to 30 carbon atoms, that is, a monovalent group obtained by removing one hydrogen atom from a bicycloalkane having 5 to 30 carbon atoms.
- bicyclo It also includes 1,2,2] heptan-2-yl group, bicyclo [2,2,2] octane-3-yl group), and tricyclostructure having many ring structures.
- the alkyl group among the substituents described below (for example, the alkyl group of the alkylthio group) also represents the alkyl group of such a concept. ]; Alkenyl group [straight, branched, cyclic alkenyl group.
- a linear or branched alkenyl group (preferably a linear or branched alkenyl group having 2 to 30 carbon atoms, for example, a vinyl group, an allyl group, a prenyl group, a geranyl group, an oleyl group), a cycloalkenyl group.
- a cycloalkenyl group having 3 to 30 carbon atoms that is, a monovalent group from which one hydrogen atom of cycloalkene having 3 to 30 carbon atoms has been removed.
- bicycloalkenyl group preferably a bicycloalkenyl group having 5 to 30 carbon atoms, that is, a monovalent group from which one hydrogen atom of bicycloalkene having one double bond has been removed, for example.
- An alkynyl group preferably a linear or branched alkynyl group having 2 to 30 carbon atoms, for example, an ethynyl group or a propargyl group
- Aryl groups preferably aryl groups having 6 to 30 carbon atoms, such as phenyl group, p-tolyl group, naphthyl group, m-chlorophenyl group, o-hexadecanoylaminophenyl group
- Heterocyclic group preferably a monovalent group obtained by removing one hydrogen atom from an aromatic or non-aromatic heterocyclic compound having 5 or 6 members, and more preferably 5 or 6 members having 3 to 30 carbon atoms.
- Alkoxy groups preferably linear or branched alkoxy groups having 1 to 30 carbon atoms, such as methoxy group, ethoxy group, isopropoxy group, t-butoxy group, n-octyloxy group
- Heterocyclic oxy group preferably a heterocyclic oxy group having 2 to 30 carbon atoms, for example, 1-phenyltetrazole-5-oxy group, 2-tetrahydropyranyloxy group
- Acyloxy group preferably formyloxy group, alkylcarbonyloxy group having 2 to 30 carbon atoms, arylcarbonyloxy group having 6 to 30 carbon atoms, for example, formyloxy group, acetyloxy group, pivaloyloxy group, stearoyloxy group, benzoyloxy group.
- Carbamoyloxy group (preferably a carbamoyloxy group having 1 to 30 carbon atoms, for example, N, N-dimethylcarbamoyloxy group, N, N-diethylcarbamoyloxy group, morpholinocarbonyloxy group, N, N-di-n- Octylaminocarbonyloxy group, Nn-octylcarbamoyloxy group); Alkoxycarbonyloxy group (preferably alkoxycarbonyloxy group having 2 to 30 carbon atoms, for example, methoxycarbonyloxy group, ethoxycarbonyloxy group, t-butoxycarbonyloxy group, n-octylcarbonyloxy group); Aryloxycarbonyloxy group (preferably an aryloxycarbonyloxy group having 7 to 30 carbon atoms; for example, a phenoxycarbonyloxy group, a p-methoxyphenoxycarbonyloxy group, a pn-hexade
- Diphenylamino group Diphenylamino group
- Acylamino group preferably formylamino group, alkylcarbonylamino group having 2 to 30 carbon atoms, arylcarbonylamino group having 6 to 30 carbon atoms, for example, formylamino group, acetylamino group, pivaloylamino group, lauroylamino group, benzoyl.
- Aminocarbonylamino group (preferably an aminocarbonylamino group having 1 to 30 carbon atoms; for example, a carbamoylamino group, an N, N-dimethylaminocarbonylamino group, an N, N-diethylaminocarbonylamino group, a morpholinocarbonylamino group); Alkoxycarbonylamino group (preferably an alkoxycarbonylamino group having 2 to 30 carbon atoms, for example, a methoxycarbonylamino group, an ethoxycarbonylamino group, a t-butoxycarbonylamino group, an n-octadecyloxycarbonylamino group, an N-methyl-methoxy group.
- Alkoxycarbonylamino group preferably an alkoxycarbonylamino group having 2 to 30 carbon atoms, for example, a methoxycarbonylamino group, an ethoxycarbonylamino group, a
- Aryloxycarbonylamino group preferably an aryloxycarbonylamino group having 7 to 30 carbon atoms; for example, a phenoxycarbonylamino group, a p-chlorophenoxycarbonylamino group, an mn-octyloxyphenoxycarbonylamino group
- Sulfamoylamino group preferably a sulfamoylamino group having 0 to 30 carbon atoms; for example, a sulfamoylamino group, an N, N-dimethylaminosulfonylamino group, an Nn-octylaminosulfonylamino group
- Alkyl or arylsulfonylamino groups preferably alkylsulfonylamino groups having 1 to 30 carbon atoms, arylsulfonylamino groups having 6 to 30 carbon atoms, such as methylsulfonylamino groups, buty
- Sulfamoyl group (preferably a sulfamoyl group having 0 to 30 carbon atoms, for example, N-ethylsulfamoyl group, N- (3-dodecyloxypropyl) sulfamoyl group, N, N-dimethylsulfamoyl group, N-acetylsul.
- Famoyl group N-benzoyl sulfamoyl group, N- (N'-phenylcarbamoyl) sulfamoyl group); Sulfone group; Alkyl or arylsulfinyl groups (preferably alkylsulfinyl groups having 1 to 30 carbon atoms, arylsulfinyl groups having 6 to 30 carbon atoms, for example, methylsulfinyl groups, ethylsulfinyl groups, phenylsulfinyl groups, p-methylphenylsulfinyl groups); Alkyl or arylsulfonyl groups (preferably alkylsulfonyl groups having 1 to 30 carbon atoms, arylsulfonyl groups of 6 to 30; for example, methylsulfonyl groups, ethylsulfonyl groups, phenylsulfonyl groups, p-methylphen
- An acyl group (preferably a formyl group, an alkylcarbonyl group having 2 to 30 carbon atoms, an arylcarbonyl group having 7 to 30 carbon atoms, a heterocyclic carbonyl group bonded to the carbonyl group with a carbon atom having 4 to 30 carbon atoms, for example.
- Aryl or heterocyclic azo groups preferably arylazo groups having 6 to 30 carbon atoms, heterocyclic azo groups having 3 to 30 carbon atoms, for example, phenylazo groups, p-chlorophenylazo groups, 5-ethylthio-1,3,4- Thianazol-2-ylazo group
- Imid group preferably N-succinimide group, N-phthalimide group
- a phosphino group preferably a phosphino group having 2 to 30 carbon atoms, for example, a dimethylphosphino group, a diphenylphosphino group, a methylphenoxyphosphino group).
- a phosphinyl group (preferably a phosphinyl group having 2 to 30 carbon atoms; for example, a phosphinyl group, a dioctyloxyphosphinyl group, a diethoxyphosphinyl group);
- a phosphinyloxy group (preferably a phosphinyloxy group having 2 to 30 carbon atoms; for example, a diphenoxyphosphinyloxy group, a dioctyloxyphosphinyloxy group);
- a phosphinylamino group (preferably a phosphinylamino group having 2 to 30 carbon atoms; for example, a dimethoxyphosphinylamino group, a dimethylaminophosphinylamino group);
- one or more hydrogen atoms may be substituted with the above-mentioned substituent T.
- substituents include alkylcarbonylaminosulfonyl groups, arylcarbonylaminosulfonyl groups, alkylsulfonylaminocarbonyl groups, and arylsulfonylaminocarbonyl groups. Specific examples include a methylsulfonylaminocarbonyl group, a p-methylphenylsulfonylaminocarbonyl group, an acetylaminosulfonyl group, a benzoylaminosulfonyl group and the like.
- the compound (1) include compounds having the following structures.
- Me is a methyl group
- Et is an ethyl group
- Bu is a butyl group
- tBu is a tert-butyl group
- Pr is a propyl group
- Ph is a phenyl group. ..
- Compound (1) is preferably used as an ultraviolet absorber.
- the maximum absorption wavelength of compound (1) is preferably in the wavelength range of 381 to 420 nm, and more preferably in the wavelength range of 381 to 400 nm.
- the molar extinction coefficient ⁇ 405 of the compound (1) calculated from the following formula at a wavelength of 405 nm is preferably 500 or more, more preferably 1000 or more, further preferably 2000 or more, and 3000 or more. Is particularly preferred.
- ⁇ 405 ⁇ max ⁇ (A 405 / A max )
- ⁇ 405 is the molar absorption coefficient of the compound (1) at a wavelength of 405 nm
- ⁇ max is the molar absorption coefficient of the compound (1) at the maximum absorption wavelength
- a 405 is the absorbance of the compound (1) at a wavelength of 405 nm.
- a max is the absorbance of the compound (1) at the maximum absorption wavelength.
- the ratio (A 430 / A 405 ) of the absorbance A 405 at a wavelength of 405 nm to the absorbance A 430 at a wavelength of 430 nm is preferably less than 0.13. , 0.1 or less is more preferable.
- the lower limit of the above ratio is not particularly limited, but may be 0 or more. Those having such an absorbance ratio are excellent in light transmission in the visible region near the ultraviolet region despite high absorption in the vicinity of the wavelength of 405 nm, and thus are excellent in absorption of ultraviolet rays on the longer wavelength side. Has excellent visible transparency.
- the ultraviolet absorption region of the compound When the ultraviolet absorption region of the compound is to be shifted to the longer wavelength side, the light transmission in the visible region (particularly, the light transmission in the visible region near the ultraviolet region) tends to decrease.
- the compound (1) of the present invention it has a technically excellent effect of excellent absorption of ultraviolet rays on the longer wavelength side while maintaining a high level of light transmission in the visible region. ..
- Compound (1) can be synthesized by referring to the synthetic methods described in JP-A-2016-081035, Japanese Patent No. 5376858, and the like.
- the content of the compound (1) in the total solid content of the resin composition is preferably 0.01 to 50% by mass.
- the lower limit is preferably 0.05% by mass or more, and more preferably 0.1% by mass or more.
- the upper limit is preferably 40% by mass or less, more preferably 30% by mass or less, and even more preferably 20% by mass or less.
- the content of the compound (1) is preferably 0.01 to 50 parts by mass with respect to 100 parts by mass of the resin.
- the lower limit is preferably 0.05 parts by mass or more, and more preferably 0.1 parts by mass or more.
- the upper limit is preferably 40 parts by mass or less, more preferably 30 parts by mass or less, and more preferably 20 parts by mass or less.
- the resin composition may contain only one kind of the compound (1), or may contain two or more kinds of the compound (1). When two or more kinds of the compound (1) are contained, the total amount thereof is preferably in the above range.
- the resin composition of the present invention preferably further contains a compound represented by the formula (2) (hereinafter, also referred to as compound (2)). According to this aspect, the storage stability of the resin composition can be further improved.
- R 11 and R 12 independently represent an alkyl group, an aryl group or a heterocyclic group, respectively.
- R 13 and R 16 independently represent a hydroxy group, an alkoxy group, an aryloxy group, an acyloxy group, a carbamoyloxy group, an alkoxycarbonyloxy group, an aryloxycarbonyloxy group, a sulfinyloxy group or a sulfonyloxy group, respectively.
- R 14 represents a halogen atom, an alkyl group, an aryl group, an alkoxy group, an aryloxy group, an acyloxy group, an alkylamino group, an anilino group, an acylamino group, an alkylsulfonylamino group, an arylsulfonylamino group, an alkylthio group or an arylthio group.
- R 15 is a hydrogen atom, a halogen atom, an alkyl group, an aryl group, an alkoxy group, an aryloxy group, an acyloxy group, an alkylamino group, an anirino group, an acylamino group, an alkylsulfonylamino group, an arylsulfonylamino group, an alkylthio group or an arylthio group.
- R 11 and R 12 may be combined with each other to form a ring
- R 13 and R 14 may be combined with each other to form a ring
- R 14 and R 15 may combine with each other to form a ring
- R 15 and R 16 may combine with each other to form a ring
- at least one of R 13 and R 16 is a hydroxy group.
- the alkyl group, aryl group and heterocyclic group represented by R 11 and R 12 of the formula (2) are synonymous with the alkyl group, aryl group and heterocyclic group represented by R 1 and R 2 of the formula (1) and are preferable.
- the range is similar.
- R 11 and R 12 of the formula (2) are preferably an alkyl group or an aryl group.
- R 13 and R 16 of the formula (2) are independently hydroxy groups, alkoxy groups, aryloxy groups, acyloxy groups, carbamoyloxy groups, alkoxycarbonyloxy groups, aryloxycarbonyloxy groups, sulfinyloxy groups or sulfonyloxy groups, respectively. It is preferably a hydroxy group, an alkoxy group or an acyloxy group, more preferably a hydroxy group or an alkoxy group, and further preferably a hydroxy group. However, at least one of R 13 and R 16 is a hydroxy group.
- the number of carbon atoms of the alkoxy group represented by R 13 and R 16 is preferably 1 to 30, more preferably 1 to 20, further preferably 1 to 15, particularly preferably 1 to 10, and most preferably 1 to 8.
- the alkoxy group may be linear or branched.
- the alkoxy group may have a substituent. Examples of the substituent include the group described in Substituent T described above.
- the aryloxy group represented by R 13 and R 16 preferably has 6 to 40 carbon atoms, more preferably 6 to 30, still more preferably 6 to 20, particularly preferably 6 to 15, and most preferably 6 to 12.
- the aryloxy group may have a substituent. Examples of the substituent include the group described in Substituent T described above.
- the number of carbon atoms of the acyloxy group represented by R 13 and R 16 is preferably 2 to 30, more preferably 2 to 20, further preferably 2 to 15, and particularly preferably 2 to 10.
- the acyloxy group may have a substituent. Examples of the substituent include the group described in Substituent T described later.
- the carbon number of the carbamoyloxy group represented by R 13 and R 16 is preferably 2 to 30, more preferably 2 to 20, further preferably 2 to 15, particularly preferably 2 to 10, and most preferably 2 to 8.
- the carbamoyloxy group may be linear or branched.
- the carbamoyloxy group may have a substituent. Examples of the substituent include the group described in Substituent T described above.
- the number of carbon atoms of the alkoxycarbonyloxy group represented by R 13 and R 16 is preferably 2 to 30, more preferably 2 to 20, further preferably 2 to 15, particularly preferably 2 to 10, and most preferably 2 to 8.
- the alkoxycarbonyloxy group may be linear or branched.
- the alkoxycarbonyloxy group may have a substituent. Examples of the substituent include the group described in Substituent T described above.
- the aryloxycarbonyloxy group represented by R 13 and R 16 preferably has 7 to 40 carbon atoms, more preferably 7 to 30 carbon atoms, further preferably 7 to 20 carbon atoms, particularly preferably 7 to 15 carbon atoms, and most preferably 7 to 12 carbon atoms.
- the aryloxycarbonyloxy group may have a substituent. Examples of the substituent include the group described in Substituent T described above.
- the number of carbon atoms of the sulfinyloxy group represented by R 13 and R 16 is preferably 1 to 30, more preferably 1 to 20, and even more preferably 1 to 15.
- the sulfinyloxy group may have a substituent. Examples of the substituent include the group described in Substituent T described above.
- the number of carbon atoms of the sulfonyloxy group represented by R 13 and R 16 is preferably 1 to 30, more preferably 1 to 20, and even more preferably 1 to 15.
- the sulfonyloxy group may have a substituent. Examples of the substituent include the group described in Substituent T described above.
- R 14 of the formula (2) is an alkyl group, an aryl group, an alkoxy group, an aryloxy group, an acyloxy group, an alkylamino group, an anilino group, an acylamino group, an alkylsulfonylamino group, an arylsulfonylamino group, an alkylthio group or an arylthio group.
- R 15 is a hydrogen atom, a halogen atom, an alkyl group, an aryl group, an alkoxy group, an aryloxy group, an acyloxy group, an alkylamino group, an anilino group, an acylamino group, alkylsulfonylamino group, arylsulfonylamino group, an alkylthio group or an Represents an arylthio group.
- the details of these groups represented by R 14 and R 15 of the formula (2) are the same as those of R 4 and R 5 of the formula (1), and the preferred range is also the same.
- R 14 is preferably an alkyl group, an aryl group, an alkoxy group or an aryloxy group
- R 15 is preferably a hydrogen atom, an alkyl group, an aryl group, an alkoxy group or an aryloxy group
- R 14 is an alkyl group or an alkoxy group.
- R 15 is more preferably a hydrogen atom, an alkyl group or an alkoxy group.
- R 14 is an alkyl group, an aryl group, an alkoxy group or an aryloxy group, and R 15 is a hydrogen atom.
- R 14 is preferably an alkyl group or an alkoxy group, and R 15 is preferably a hydrogen atom.
- R 14 and R 15 are independently alkyl groups, aryl groups, alkoxy groups or aryloxy groups, respectively.
- R 14 and R 15 are preferably independent alkyl or alkoxy groups, respectively , both R 14 and R 15 are alkyl groups, or both R 14 and R 15 are alkoxy groups. Is more preferable.
- the compound (2) include compounds having the following structures.
- Me is a methyl group
- Et is an ethyl group
- tBu is a tert-butyl group
- Pr is a propyl group
- Bu is a butyl group
- Ph is a phenyl group. ..
- Compound (2) can be synthesized according to the method described in Japanese Patent No. 5376858, International Publication No. 2019/142039.
- Compound (2) is preferably used as an ultraviolet absorber.
- the maximum absorption wavelength of compound (2) is preferably in the wavelength range of 381 to 420 nm, and more preferably in the wavelength range of 381 to 400 nm.
- the content of the compound (2) is preferably 5 parts by mass or less, preferably 3 parts by mass or less, based on 100 parts by mass of the compound (1). More preferably, it is 1 part by mass or less.
- the lower limit is preferably 0.1 parts by mass or more.
- the total content of the compound (1) and the compound (2) in the total solid content of the resin composition is preferably 0.01 to 50% by mass.
- the lower limit is preferably 0.05% by mass or more, and more preferably 0.1% by mass or more.
- the upper limit is preferably 40% by mass or less, more preferably 30% by mass or less, and even more preferably 20% by mass or less.
- the total content of the compound (1) and the compound (2) is preferably 0.01 to 50 parts by mass with respect to 100 parts by mass of the resin.
- the lower limit is preferably 0.05 parts by mass or more, and more preferably 0.1 parts by mass or more.
- the upper limit is preferably 40 parts by mass or less, more preferably 30 parts by mass or less, and more preferably 20 parts by mass or less.
- the resin composition may contain only one kind of the compound (2), or may contain two or more kinds of the compound (2). When two or more kinds of the compound (2) are contained, the total amount thereof is preferably in the above range.
- the resin composition does not substantially contain the compound (2). According to this aspect, more excellent light resistance can be easily obtained.
- the content of the compound (2) in the total solid content of the resin composition is 0.001% by mass or less. That is, it is preferably 0.0001% by mass or less, and more preferably not contained.
- the resin composition of the present invention may contain an ultraviolet absorber other than the above-mentioned compound (1) (hereinafter, also referred to as another ultraviolet absorber). According to this aspect, it is possible to form a cured product capable of blocking light having a wavelength in the ultraviolet region over a wide range.
- the maximum absorption wavelength of other UV absorbers is preferably in the wavelength range of 390 nm or less, and more preferably in the wavelength range of 380 nm or less.
- UV absorbers examples include benzotriazole-based UV absorbers, benzophenone-based UV absorbers, salicylic acid-based UV absorbers, acrylate-based UV absorbers, benzodithiol-based UV absorbers, and triazine-based UV absorbers.
- Benzotriazole-based UV absorbers, benzophenone-based UV absorbers and triazine-based UV absorbers are preferable, and benzotriazole-based UV absorbers and triazine-based UV absorbers are more preferable.
- benzotriazole-based UV absorber Specific examples of the benzotriazole-based UV absorber, the benzophenone-based UV absorber, the salicylic acid-based UV absorber, the acrylate-based UV absorber, and the triazine-based UV absorber are described in paragraphs 0065 to 0070 of JP2009-263616A. Examples thereof include the compounds described, the compounds described in paragraph No. 0065 of WO 2017/122503, and the contents thereof are incorporated in the present specification. Further, a compound having the following structure can also be preferably used as another ultraviolet absorber.
- the content of the other UV absorber in the total solid content of the resin composition is preferably 0.01 to 50% by mass.
- the lower limit is preferably 0.05% by mass or more, and more preferably 0.1% by mass or more.
- the upper limit is preferably 40% by mass or less, more preferably 30% by mass or less, and even more preferably 20% by mass or less.
- the total content of the compound (1), the compound (2), and other ultraviolet absorbers in the total solid content of the resin composition is preferably 0.01 to 50% by mass.
- the lower limit is preferably 0.05% by mass or more, and more preferably 0.1% by mass or more.
- the upper limit is preferably 40% by mass or less, more preferably 30% by mass or less, and even more preferably 20% by mass or less.
- the resin composition may contain only one type of other ultraviolet absorber, or may contain two or more types. When two or more other UV absorbers are contained, the total amount thereof is preferably in the above range.
- the resin composition of the present invention contains a resin.
- resins include (meth) acrylic resins, polyester resins, polycarbonate resins, vinyl polymers [eg, polydiene resins, polyalkene resins, polystyrene resins, polyvinyl ether resins, polyvinyl alcohol resins, polyvinyl ketone resins, polyfluorovinyl resins and Polyvinyl bromide resin, etc.], polythioether resin, polyphenylene resin, polyurethane resin, polythiourethane resin, polysulfonate resin, nitrosopolymer resin, polysiloxane resin, polysulfide resin, polythioester resin, polysulfone resin, polysulfoneamide resin, polyamide Resin, polyimine resin, polyurea resin, polyphosphazene resin, polysilane resin, polysilazane resin, polyfuran resin, polybenzoxazole resin, polyoxadiazole
- vinyl polymers
- a resin having a polymerizable group can also be used.
- Commercially available products of resins having a polymerizable group include dianal BR series (polymethyl methacrylate (PMMA), for example, dianal BR-80, BR-83, BR-87; Mitsubishi Chemical Co., Ltd.); Photomer 6173 (containing COOH).
- (meth) acrylic resin, polystyrene resin, polyester resin, polyurethane resin, polythio because it has good compatibility with compound (1) and it is easy to obtain a cured product with suppressed surface unevenness. It is preferably at least one selected from urethane resin, polyimide resin, epoxy resin, polycarbonate resin and cellulose acylate resin, and is preferably (meth) acrylic resin, polystyrene resin, polyester resin, polyurethane resin, polythiourethane resin, polycarbonate resin. And at least one selected from cellulose acylate resins is more preferred.
- the cellulose acylate resin As the cellulose acylate resin, the cellulose acylate described in paragraphs 0016 to 0021 of JP2012-215689A is preferably used.
- the polyester resin a commercially available product such as the Byron series (for example, Byron 500) manufactured by Toyobo Co., Ltd. can also be used.
- the SK Dyne series As a commercially available product of the (meth) acrylic resin, the SK Dyne series (for example, SK Dyne-SF2147) manufactured by Soken Chemical Co., Ltd. can also be used.
- the polystyrene resin it is preferable to use the polystyrene-based resin described below.
- the styrene-based resin represents a resin in which the monomer unit having the highest ratio among the monomer units constituting the resin is the monomer unit derived from the styrene monomer.
- the styrene-based monomer means a monomer having a styrene skeleton in its structure.
- the styrene-based resin preferably contains 70% by mass or more of monomer units derived from the styrene-based monomer, and more preferably 85% by mass or more.
- the styrene-based monomer may be a homopolymer of styrene or a derivative thereof, and may be a binary or more copolymer of styrene or a derivative thereof and another copolymerizable monomer.
- the styrene derivative is a compound in which another group is bonded to styrene, and is, for example, o-methylstyrene, m-methylstyrene, p-methylstyrene, 2,4-dimethylstyrene, o-ethylstyrene, and the like.
- Alkylstyrene such as p-ethylstyrene, and hydroxyl group, alkoxy group, carboxyl group, etc. on the benzene nucleus of styrene such as hydroxystyrene, tert-butoxystyrene, vinyl benzoic acid, o-chlorostyrene, p-chlorostyrene, etc. Examples thereof include substituted styrene in which halogen and the like are introduced.
- the styrene-based resin also includes a styrene-based monomer component copolymerized with another monomer component.
- the copolymerizable monomer include alkyl methacrylates such as methyl methacrylate, cyclohexyl methacrylate, methyl phenyl methacrylate, and isopropyl methacrylate; methylacryllate, ethylacryllate, and the like.
- Unsaturated carboxylic acid alkyl ester monomers such as alkylacryllates such as butylacryllate, 2-ethylhexylacryllate, cyclohexylacryllate; methacrylic acid, acrylic acid, itaconic acid, maleic acid, fumaric acid , Unsaturated carboxylic acid monomer such as cinnamic acid; unsaturated dicarboxylic acid anhydride monomer which is an anhydride such as maleic anhydride, itaconic acid, ethylmaleic acid, methylitaconic acid, chloromaleic acid; Unsaturated nitrile monomers such as lonitrile; 1,3-butadiene, 2-methyl-1,3-butadiene (isoprene), 2,3-dimethyl-1,3-butadiene, 1,3-pentadiene, 1, Examples thereof include conjugated diene such as 3-hexadiene, and it is also possible to copolymerize two or more
- styrene resin examples include AS-70 (acrylonitrile / styrene copolymer resin, manufactured by Nippon Steel & Sumikin Chemical Co., Ltd.), SMA2000P (styrene / maleic acid copolymer, Kawahara Yuka Co., Ltd.) and the like.
- the styrene resin As the styrene resin, a plurality of types having different compositions, molecular weights, etc. can be used in combination.
- the styrene resin can be obtained by a known anion, lump, suspension, emulsification or solution polymerization method.
- the unsaturated double bond of the benzene ring of the conjugated diene or the styrene-based monomer may be hydrogenated.
- the hydrogenation rate can be measured by a nuclear magnetic resonance apparatus (NMR).
- the weight average molecular weight (Mw) of the resin is preferably 3000 to 2000000.
- the upper limit is preferably 1,000,000 or less, and more preferably 500,000 or less.
- the lower limit is preferably 4000 or more, and more preferably 5000 or more.
- the total light transmittance of the resin is preferably 80% or more, more preferably 85% or more, and further preferably 90% or more.
- the total light transmittance of the resin is a value measured based on the contents described on pages 225 to 232 of "4th Edition Experimental Chemistry Course 29 Polymer Material Medium” (Maruzen, 1992) edited by the Chemical Society of Japan. Is.
- the content of the resin in the total solid content of the resin composition is preferably 1 to 99.9% by mass.
- the lower limit is preferably 70% by mass or more.
- the upper limit is preferably 95% by mass or less, and more preferably 90% by mass or less.
- the resin composition may contain only one type of resin, or may contain two or more types of resin. When two or more kinds of resins are contained, the total amount thereof is preferably in the above range.
- the resin composition can contain a curable compound.
- the curable compound include a polymerizable compound and a compound having an —O—Si—O— structure.
- the polymerizable compound a compound that can be polymerized and cured by applying energy can be used without limitation.
- the polymerizable compound include a compound having an ethylenically unsaturated bond-containing group, a compound having an epoxy group, a compound having a methylol group, and the like, and a compound having an ethylenically unsaturated bond-containing group is preferable, and ethylene is preferable. It is more preferable that the compound has two or more sex unsaturated bond-containing groups.
- the ethylenically unsaturated bond-containing group include a vinyl group, an allyl group, and a (meth) acryloyl group.
- the polymerizable compound is, for example, a monomer, a prepolymer (that is, a dimer, a trimer, or an oligomer), and a mixture thereof, and a (co) polymer of a compound selected from the monomer and the prepolymer. It may be either.
- Examples of compounds having an ethylenically unsaturated bond-containing group used as a polymerizable compound include unsaturated carboxylic acids (for example, acrylic acid, methacrylic acid, itaconic acid, crotonic acid, isocrotonic acid, maleic acid, etc.) and unsaturated carboxylic acids. And amides of unsaturated carboxylic acids, and (co) polymers of unsaturated carboxylic acids or esters or amides thereof. Of these, esters of unsaturated carboxylic acids and aliphatic polyhydric alcohols, amides of unsaturated carboxylic acids and aliphatic polyhydric amines, and homopolymers or copolymers thereof are preferable.
- an unsaturated carboxylic acid ester or an unsaturated carboxylic acid having a nucleophilic substituent for example, a hydroxy group, an amino group, a mercapto group, etc.
- the compound having an ethylenically unsaturated bond-containing group used as a polymerizable compound includes a plurality of compounds having different functional numbers or a plurality of compounds having different types of polymerizable groups (for example, acrylic acid ester, methacrylic acid ester, etc.).
- a styrene compound, a vinyl ether compound, etc. may be used in combination.
- Examples of the compound having an epoxy group used as a polymerizable compound include a monofunctional or polyfunctional glycidyl ether compound and a polyfunctional aliphatic glycidyl ether compound. Further, as the epoxy compound, a compound having an alicyclic epoxy group can also be used. Examples of the epoxy compound include compounds having one or more epoxy groups in one molecule.
- the epoxy compound is preferably a compound having 1 to 100 epoxy groups in one molecule.
- the upper limit of the number of epoxy groups may be, for example, 10 or less, or 5 or less.
- the lower limit of the epoxy group is preferably two or more.
- the monofunctional epoxy compound examples include 2-ethylhexyl glycidyl ether.
- Specific examples of the polyfunctional epoxy compound include 1,4-cyclohexanedimethanol diglycidyl ether, 3', 4'-epoxycyclohexylmethyl 3,4-epoxycyclohexanecarboxylate and the like.
- the epoxy compound may be either a low molecular weight compound (for example, a molecular weight of less than 1000) or a high molecular weight compound (macromolecule) (for example, a molecular weight of 1000 or more, and in the case of a polymer, a weight average molecular weight of 1000 or more).
- the weight average molecular weight of the epoxy compound is preferably 2000 to 100,000.
- the upper limit of the weight average molecular weight is preferably 10,000 or less, more preferably 5000 or less, and even more preferably 3000 or less.
- epoxy compounds include celloxide 2021P (trade name: 3', 4'-epoxycyclohexylmethyl 3,4-epoxycyclohexanecarboxylate) manufactured by Daicel Co., Ltd., and ricaredin DME-100 manufactured by Shin Nihon Rika Co., Ltd.
- polyfunctional epoxy compounds such as (trade name, containing 1,4-cyclohexanedimethanol diglycidyl ether as a main component).
- Examples of the compound having a methylol group include a compound in which the methylol group is bonded to a nitrogen atom or a carbon atom forming an aromatic ring.
- Compounds in which the methylol group is bonded to a nitrogen atom include alkoxymethylated melamine, methylolated melamine, alkoxymethylated benzoguanamine, methylolated benzoguanamine, alkoxymethylated glycoluryl, methylolated glycoluryl, alkoxymethylated urea, and methylol.
- Examples thereof include a trimethylolpropane-imparted product of urea compound and tolylene diisocyanate.
- a polymer compound can also be used as the polymerizable compound.
- the polymerizable compound of the polymer include (meth) acrylic resin, ester resin, urethane resin, and fluororesin.
- examples of commercially available products on the market are the dianal BR series (polymethyl methacrylate (PMMA), for example, dianal BR-80, BR-83, BR-87; Mitsubishi Chemical Corporation); Photomer 6173 (COOH-containing polyurethane).
- Acrylic oligomer Diamond Shamlock Co., Ltd.
- Viscort R-264 KS resist 106 (all from Osaka Organic Chemical Corporation)
- Cyclomer P series for example, ACA230AA
- Praxel CF200 series all from Daicel Co., Ltd.
- Ebecryl3800 Dycel UCB Co., Ltd.
- Acrycure-RD-F8 Nippon Catalyst Co., Ltd.
- the polymerizable compound is a component that also corresponds to a resin.
- the polymer polymerizable compound is preferably a compound capable of forming a crosslinked structure from the viewpoint of improving the strength after curing.
- the formation of the crosslinked structure is not particularly limited, and for example, a method in which a polymer polymerizable compound and a polyfunctional (meth) acrylate monomer are used in combination; Examples thereof include a method in which a cross-linking agent having a cross-linking group capable of reacting with the above-mentioned reactive group is used in combination.
- Examples of the reactive group include a group containing active hydrogen, and specific examples thereof include a group selected from the group consisting of a hydroxyl group, a primary amino group and a secondary amino group.
- Examples of the polymerizable compound of the polymer into which the reactive group has been introduced include a (meth) acrylic resin containing a structural unit derived from a (meth) acrylate monomer and having two or more groups containing active hydrogen.
- Examples of the cross-linking agent include polyisocyanates having two or more isocyanate groups as cross-linking groups, and examples of commercially available products on the market are AD-TMP and A-9550 of Shin Nakamura Chemical Industry Co., Ltd. (both). Product name) and the like.
- a (meth) acrylic resin having 2 or more (preferably 3 or more) groups containing active hydrogen and a cross-linking agent having 2 or more isocyanate groups are preferable, and more preferably 3.
- Polyisocyanate having the above isocyanate group is preferably used in combination.
- a crosslinked structure can be formed by reacting a group containing active hydrogen with an isocyanate group.
- the compound having an —O—Si—O— structure is preferably a hydrolyzable silicon compound, more preferably a hydrolyzable alkoxysilane, and further preferably a trifunctional or tetrafunctional alkoxysilane. preferable.
- Specific examples of the compound having an —O—Si—O— structure include tetramethoxysilane, tetraethoxysilane, tetra-n-propoxysilane, tetra-i-propoxysilane, tetra-n-butoxysilane, and methyltrimethoxysilane.
- the content of the curable compound in the total solid content of the resin composition is preferably 0.1 to 90% by mass.
- the lower limit is preferably 1% by mass or more, and more preferably 5% by mass or more.
- the upper limit is preferably 80% by mass or less, and more preferably 70% by mass or less.
- the resin composition may contain only one type of curable compound, or may contain two or more types. When two or more kinds of curable compounds are contained, the total amount thereof is preferably in the above range.
- the resin composition can contain a polymerization initiator.
- a polymerizable compound when used as the curable compound, it is preferable to contain a polymerization initiator.
- the polymerization reaction of the polymerizable compound can be started satisfactorily.
- the polymerization initiator a compound capable of generating an initiator required for the polymerization reaction by applying energy can be used.
- the polymerization initiator for example, a photopolymerization initiator and a thermal polymerization initiator can be appropriately selected, and a photopolymerization initiator is preferable.
- the photopolymerization initiator for example, a compound having light absorption from the ultraviolet region to the visible region (for example, 280 nm to 400 nm) is preferable, and a photoradical initiator and photocationic polymerization that generate active radicals to initiate photoradical polymerization are preferable. Included are cation initiators that initiate radicals.
- Examples of the photopolymerization initiator include halogenated hydrocarbon derivatives (for example, compounds having a triazine skeleton, compounds having an oxadiazole skeleton, etc.), acylphosphine compounds, hexaarylbiimidazoles, oxime compounds, organic peroxides, and thio compounds. , Ketone compounds, aromatic onium salts, aminoacetophenone compounds, hydroxyacetophenone compounds and the like. Examples of the aminoacetophenone compound include aminoacetophenone-based initiators described in JP-A-2009-191179 and JP-A-10-291969. Examples of the acylphosphine compound include the acylphosphine-based initiator described in Japanese Patent No. 4225898. As the photopolymerization initiator, a synthetic product may be used, or a commercially available product on the market may be used.
- Examples of commercially available hydroxyacetophenone compounds include Omnirad 184, Omnirad 1173, Omnirad 2959, Omnirad 127 (all manufactured by IGM Resins BV) and the like.
- Examples of commercially available aminoacetophenone compounds include Omnirad 907, Omnirad 369, Omnirad 369E, Omnirad 379EG (all manufactured by IGM Resins BV) and the like.
- Examples of commercially available acylphosphine compounds include Omnirad 819 and Omnirad TPO (all manufactured by IGM Resins BV).
- an oxime compound is preferable.
- the oxime compound include the compound described in JP-A-2001-233842, the compound described in JP-A-2000-080068, the compound described in JP-A-2006-342166, and JP-A-2016-006475. Examples thereof include the compounds described in paragraphs 0073 to 0075 of the publication.
- the oxime compounds the oxime ester compound is preferable. Examples of commercially available oxime compounds include Irgacure OXE01, Irgacure OXE02 (manufactured by BASF), and Irgacure OXE03 (manufactured by BASF).
- Examples of the cationic polymerization initiator include an initiator for initiating photocationic polymerization, a photochromic agent for a dye compound, a photochromic agent, a known acid generator used in a microresist, and the like, and a mixture thereof.
- examples of the cationic polymerization initiator include onium compounds, organic halogen compounds, and disulfone compounds.
- Examples of the onium compound include diazonium salt, ammonium salt, iminium salt, phosphonium salt, iodonium salt, sulfonium salt, arsonium salt, selenonium salt and the like. Details of the onium compound include the compounds described in paragraphs 0058 to 0059 of JP-A-2002-209162.
- the content of the polymerization initiator in the total solid content of the resin composition is preferably 0.1 to 20% by mass.
- the lower limit is preferably 0.3% by mass or more, and more preferably 0.4% by mass or more.
- the upper limit is preferably 15% by mass or less, and more preferably 10% by mass or less.
- the resin composition may contain only one type of polymerization initiator, or may contain two or more types of polymerization initiators. When two or more kinds of polymerization initiators are contained, the total amount thereof is preferably in the above range.
- the resin composition of the present invention can contain an acid generator.
- an acid generator may be a photoacid generator or a thermoacid generator.
- the acid generator means a compound that generates an acid by applying energy such as heat or light.
- the thermoacid generator means a compound that generates an acid by thermal decomposition.
- the photoacid generator means a compound that generates an acid by irradiation with light.
- Types of acid generators, specific compounds, and preferred examples include the compounds described in paragraphs 0066 to 0122 of JP2008-013646, which can also be applied to the present invention. it can.
- thermoacid generator examples include compounds having a thermal decomposition temperature in the range of 130 ° C. to 250 ° C., and more preferably a compound in the range of 150 ° C. to 220 ° C.
- thermoacid generator examples include compounds that generate low nucleophilic acids such as sulfonic acid, carboxylic acid, and disulfonylimide by heating.
- an acid having a pKa of 4 or less is preferable, an acid having a pKa of 3 or less is more preferable, and an acid having a pKa of 2 or less is further preferable.
- alkylcarboxylic acids, arylcarboxylic acids, disulfonylimides and the like substituted with sulfonic acids and electron-withdrawing groups are preferable.
- the electron-withdrawing group include a halogen atom such as a fluorine atom, a haloalkyl group such as a trifluoromethyl group, a nitro group, and a cyano group.
- Photoacid generators include onium salt compounds such as diazonium salt, phosphonium salt, sulfonium salt, and iodonium salt, which are decomposed by light irradiation to generate acid, imide sulfonate, oxime sulfonate, diazodisulfone, disulfone, ortho-nitrobenzyl. Examples thereof include sulfonate compounds such as sulfonate.
- photoacid generators examples include WPAG-469 (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.), CPI-100P (manufactured by Sun Appro Co., Ltd.), Irgacure 290 (manufactured by BASF Japan Ltd.), and the like. Further, 2-isopropylthioxanthone or the like can also be used as the photoacid generator.
- the content of the acid generator is preferably 0.1 to 100 parts by mass, more preferably 0.1 to 50 parts by mass with respect to 100 parts by mass of the curable compound. Yes, more preferably 0.1 to 20 parts by mass.
- the resin composition may contain only one type of acid generator, or may contain two or more types. When two or more types of acid generator media are contained, the total amount thereof is preferably in the above range.
- the resin composition can contain a catalyst.
- a catalyst when a compound having an —O—Si—O— structure is used as the curable compound, it is preferable to contain a catalyst. According to this aspect, the sol-gel reaction is promoted, and a stronger film can be easily obtained.
- the catalyst include acid catalysts such as hydrochloric acid, sulfuric acid, acetic acid and propionic acid, and base catalysts such as sodium hydroxide, potassium hydroxide and triethylamine.
- the content of the catalyst is preferably 0.1 to 100 parts by mass, more preferably 0.1 to 50 parts by mass, and further preferably 0.1 to 50 parts by mass with respect to 100 parts by mass of the curable compound. Is 0.1 to 20 parts by mass.
- the resin composition may contain only one type of catalyst, or may contain two or more types of catalysts. When two or more types of catalysts are contained, the total amount thereof is preferably in the above range.
- the resin composition of the present invention can contain a silane coupling agent.
- the adhesion of the obtained film to the support can be further improved.
- the silane coupling agent means a silane compound having a hydrolyzable group and other functional groups.
- the hydrolyzable group refers to a substituent that is directly linked to a silicon atom and can form a siloxane bond by at least one of a hydrolysis reaction and a condensation reaction. Examples of the hydrolyzable group include a halogen atom, an alkoxy group, an acyloxy group and the like, and an alkoxy group is preferable.
- the silane coupling agent is preferably a compound having an alkoxysilyl group.
- the functional group other than the hydrolyzable group include a vinyl group, a (meth) allyl group, a (meth) acryloyl group, a mercapto group, an epoxy group, an oxetanyl group, an amino group, a ureido group, a sulfide group and an isocyanate group.
- a phenyl group and the like preferably an amino group, a (meth) acryloyl group and an epoxy group.
- silane coupling agent examples include the compounds described in paragraphs 0018 to 0036 of JP2009-288703A and the compounds described in paragraphs 0056 to 0066 of JP2009-242604A. The contents of are incorporated herein by reference.
- examples of commercially available silane coupling agents include A-50 (organosilane) manufactured by Soken Chemical Co., Ltd.
- the content of the silane coupling agent in the total solid content of the resin composition is preferably 0.1 to 5% by mass.
- the upper limit is preferably 3% by mass or less, and more preferably 2% by mass or less.
- the lower limit is preferably 0.5% by mass or more, and more preferably 1% by mass or more.
- the silane coupling agent may be only one kind or two or more kinds. In the case of two or more types, the total amount is preferably in the above range.
- the resin composition of the present invention can contain a surfactant.
- various surfactants such as a fluorine-based surfactant, a nonionic surfactant, a cationic surfactant, an anionic surfactant, and a silicon-based surfactant can be used.
- the surfactant is preferably a fluorine-based surfactant.
- the fluorine content in the fluorine-based surfactant is preferably 3 to 40% by mass, more preferably 5 to 30% by mass, and particularly preferably 7 to 25% by mass.
- a fluorine-based surfactant having a fluorine content within this range is effective in terms of uniformity of coating film thickness and liquid saving property, and has good solubility in a resin composition.
- fluorine-based surfactants include, for example, Megafuck F-171, F-172, F-173, F-176, F-177, F-141, F-142, F-143, F-144. , F-437, F-475, F-477, F-479, F-482, F-554, F-555-A, F-556, F-557, F-558, F-559, F-560.
- Nonionic surfactants include glycerol, trimethylolpropane, trimethylolethane, their ethoxylates and propoxylates (eg, glycerol propoxylate, glycerol ethoxylate, etc.), polyoxyethylene lauryl ethers, polyoxyethylene stearyl ethers, etc.
- silicone-based surfactant examples include Torre Silicone DC3PA, Torre Silicone SH7PA, Torre Silicone DC11PA, Torre Silicone SH21PA, Torre Silicone SH28PA, Torre Silicone SH29PA, Torre Silicone SH30PA, Torre Silicone SH8400 (all, Toray Dow Corning Co., Ltd.).
- TSF-4440, TSF-4300, TSF-4445, TSF-4460, TSF-4452 above, manufactured by Momentive Performance Materials
- KP-341, KF-6001, KF-6002 above, (Made by Shin-Etsu Chemical Industry Co., Ltd.), BYK-307, BYK-323, BYK-330, BYK-3760, BYK-UV3510 (all manufactured by Big Chemie) and the like.
- the fluorine-based surfactant has a linear perfluoroalkyl group having 7 or more carbon atoms, such as perfluorooctanoic acid (PFOA) and perfluorooctanesulfonic acid (PFOS), from the viewpoint of improving environmental suitability. It is preferable to use a surfactant derived from a substitute material for the compound.
- PFOA perfluorooctanoic acid
- PFOS perfluorooctanesulfonic acid
- the content of the surfactant in the total solid content of the resin composition is preferably 0.001% by mass to 5.0% by mass, more preferably 0.005 to 3.0% by mass.
- the surfactant may be only one kind or two or more kinds. In the case of two or more types, the total amount is preferably in the above range.
- the resin composition preferably further contains a solvent.
- the solvent is not particularly limited, and examples thereof include water and an organic solvent.
- examples of the organic solvent include alcohol solvents, ester solvents, ketone solvents, amide solvents, ether solvents, hydrocarbon solvents, halogen solvents and the like.
- organic solvent examples include methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 2-butanol, 2-methyl-1-propanol, 1-methoxy-2-propanol, 2-ethoxyethanol, 2 -Butoxyethanol, polyethylene glycol monoalkyl ether, polypropylene glycol monoalkyl ether, ethylene glycol, propylene glycol, polyethylene glycol, polypropylene glycol, glycerin, ethylene carbonate, N-methylpyrrolidone, dioxane, tetrahydrofuran, ethylene glycol dialkyl ether, propylene glycol dialkyl Ether, polyethylene glycol dialkyl ether, polypropylene glycol dialkyl ether, acetonitrile, propionitrile, benzonitrile, carboxylic acid ester, phosphoric acid ester, phosphonic acid ester, dimethyl sulfoxide, sulfolane, dimethylformamide,
- the resin composition may appropriately contain any additive such as an antioxidant, a light stabilizer, a processing stabilizer, an antioxidant, and a compatibilizer, if necessary. By appropriately containing these components, various properties of the obtained cured product can be appropriately adjusted.
- the resin composition of the present invention can also be suitably used for applications that may be exposed to light including sunlight or ultraviolet rays.
- Specific examples include coating materials or films for window glass of houses, facilities, transportation equipment, etc .; interior / exterior materials and interior / exterior paints of houses, facilities, transportation equipment, etc .; members for light sources that emit ultraviolet rays, such as fluorescent lamps and mercury lamps.
- the resin composition of the present invention is preferably used for an ultraviolet cut filter, a lens, or a protective material.
- the form of the protective material is not particularly limited, and examples thereof include a coating film shape, a film shape, and a sheet shape. Further, the resin composition of the present invention can also be used as an adhesive or an adhesive.
- the resin composition of the present invention can also be used for various members of a display device.
- a liquid crystal display device it can be used for each member constituting the liquid crystal display device such as an antireflection film, a polarizing plate protective film, an optical film, a retardation film, an adhesive, and an adhesive.
- an organic electroluminescence display device an optical film, a polarizing plate protective film in a circularly polarizing plate, a retardation film such as a 1/4 wave plate, and an organic electroluminescence display device such as an adhesive or an adhesive are configured. It can be used for each member.
- the cured product of the present invention is obtained by using the above-mentioned resin composition of the present invention.
- the "cured product" in the present specification includes a dried product obtained by drying and solidifying the resin composition, and, when the resin composition undergoes a curing reaction, a cured product obtained by curing the resin composition and curing the resin composition. ..
- the cured product of the present invention may be obtained as a molded product obtained by molding a resin composition into a desired shape.
- the shape of the molded product can be appropriately selected according to the intended use and purpose. For example, coating film-like, film-like, sheet-like, plate-like, lenticular-like, tubular, fibrous-like and the like can be mentioned.
- the cured product of the present invention is preferably used as an optical member.
- the optical member include an ultraviolet cut filter, a lens, and a protective material. It can also be used as a polarizing plate or the like.
- the ultraviolet cut filter can be used for articles such as optical filters, display devices, solar cells, and window glass.
- the type of display device is not particularly limited, and examples thereof include a liquid crystal display device and an organic electroluminescence display device.
- the cured product of the present invention When the cured product of the present invention is used for a lens, the cured product of the present invention itself may be formed into a lens shape and used. Further, the cured product of the present invention may be used for the coating film on the lens surface, the intermediate layer (adhesive layer) of the bonded lens, and the like. Examples of the bonded lens include those described in paragraphs 0094 to 0102 of International Publication No. 2019/131572, the contents of which are incorporated in the present specification.
- the type of protective material is not particularly limited, and examples thereof include a protective material for display devices, a protective material for solar cells, a protective material for window glass, and an organic electroluminescence display device.
- the shape of the protective material is not particularly limited, and examples thereof include a coating film shape, a film shape, and a sheet shape.
- the ultraviolet absorber of the present invention contains the compound represented by the above formula (1) (compound (1)).
- the compound (1) is the same as the content described in the above-mentioned section of the resin composition, and the preferable range is also the same.
- the compound (1) used for the ultraviolet absorber is preferably the compound represented by the above-mentioned formula (1a).
- the ultraviolet absorber of the present invention can also be used by adding it to an adhesive or an adhesive.
- the pressure-sensitive adhesive include an acrylic pressure-sensitive adhesive, a rubber-based pressure-sensitive adhesive, and a silicone-based pressure-sensitive adhesive.
- the acrylic pressure-sensitive adhesive refers to a pressure-sensitive adhesive containing a polymer of a (meth) acrylic monomer ((meth) acrylic polymer).
- the adhesive include urethane resin adhesives, polyester adhesives, acrylic resin adhesives, ethylene vinyl acetate resin adhesives, polyvinyl alcohol adhesives, polyamide adhesives, silicone adhesives and the like. Among them, a urethane resin adhesive or a silicone adhesive is preferable as the adhesive in terms of high adhesive strength.
- the adhesive a commercially available product on the market may be used.
- the commercially available product are urethane resin adhesive (LIS-073-50U: trade name) of Toyo Ink Co., Ltd. and acrylic of Soken Kagaku Co., Ltd. Examples thereof include a system adhesive (SK Dyne-SF2147: trade name).
- a curing agent may be further used in combination with the adhesive. Examples of commercially available curing agents include CR-001 (trade name) of Toyo Ink Co., Ltd.
- the content of the compound (1) in the ultraviolet absorber is preferably 1 to 100% by mass, more preferably 10 to 100% by mass, and even more preferably 20 to 100% by mass.
- the ultraviolet absorber may contain only one type of compound (1), or may contain two or more types. When two or more kinds of the compound (1) are contained, the total amount thereof is preferably in the above range.
- the ultraviolet absorber of the present invention preferably further contains the compound represented by the above-mentioned formula (2) (compound (2)).
- compound (2) has the same contents as those described in the above-mentioned section of the resin composition, and the preferable range is also the same.
- the content of the compound (2) is preferably 5 parts by mass or less, preferably 3 parts by mass or less, based on 100 parts by mass of the compound (1). More preferably, it is 1 part by mass or less.
- the lower limit is preferably 0.1 parts by mass or more.
- the ultraviolet absorber may contain only one type of compound (2), or may contain two or more types. When two or more kinds of the compound (2) are contained, the total amount thereof is preferably in the above range.
- the optical member of the present invention includes the above-mentioned ultraviolet absorber of the present invention. It is also preferable that the optical member of the present invention contains a cured product obtained by using the above-mentioned resin composition of the present invention.
- the cured product of the present invention may be obtained as a molded product obtained by molding the above-mentioned resin composition of the present invention into a desired shape.
- the shape of the molded product can be appropriately selected according to the intended use and purpose. For example, coating film-like, film-like, sheet-like, plate-like, lenticular-like, tubular, fibrous-like and the like can be mentioned.
- the optical member of the present invention may be obtained by using an adhesive or an adhesive containing the ultraviolet absorber of the present invention.
- it may be a member in which a polarizing plate and a polarizing plate protective film are attached using an adhesive or an adhesive containing an ultraviolet absorber.
- optical members examples include ultraviolet cut filters, lenses, protective materials, and the like.
- the ultraviolet cut filter can be used for articles such as optical filters, display devices, solar cells, and window glass.
- the type of display device is not particularly limited, and examples thereof include a liquid crystal display device and an organic electroluminescence display device.
- the lens is a lens formed by the cured product of the present invention itself; a coating film on the lens surface, an intermediate layer (adhesive layer or adhesive layer) of a bonded lens, or the like containing the ultraviolet absorber of the present invention. Can be mentioned.
- the type of protective material is not particularly limited, and examples thereof include a protective material for display devices, a protective material for solar cells, and a protective material for window glass.
- the shape of the protective material is not particularly limited, and examples thereof include a coating film shape, a film shape, and a sheet shape.
- a resin film can be mentioned.
- the resin film can be formed by using the resin composition of the present invention described above.
- the resin used in the resin composition for forming a resin film include the above-mentioned resins, and (meth) acrylic resin, polyester fiber, cyclic olefin resin and cellulose acylate resin are preferable, and cellulose acylate resin is more preferable.
- the resin composition containing the cellulose acylate resin can contain the additives described in paragraphs 0022 to 0067 of JP2012-215689A. Examples of such additives include sugar esters and the like.
- the sugar ester compound By adding the sugar ester compound to the resin composition containing the cellulose acylate resin, it is possible to reduce the total haze and the internal haze without impairing the expressiveness of the optical properties and even if the heat treatment is not performed before the stretching step. it can.
- the sugar ester include sugar ester 1 and sugar ester 2 described in Examples described later.
- the resin film (cellulose acylate film) can be produced by the method described in paragraphs 0068 to 0906 of JP2012-215689A using the resin composition containing the cellulose acylate resin. Further, the hard coat layer described in paragraphs 0907 to 0113 of JP2012-215689A may be further laminated on the resin film.
- an optical member having a laminated body of a transparent support base material and a resin layer can be mentioned.
- at least one of the supporting base material and the resin layer is obtained by using the above-mentioned resin composition of the present invention, or contains the above-mentioned ultraviolet absorber of the present invention.
- Such an optical member is preferably used as a film or sheet-shaped ultraviolet cut filter or protective material.
- the supporting base material preferably has transparency as long as the optical performance is not impaired.
- the fact that the supporting base material is transparent means that it is optically transparent, and specifically, that the total light transmittance of the supporting base material is 85% or more.
- the total light transmittance of the supporting base material is preferably 90% or more, more preferably 95% or more.
- the total light transmittance of the supporting base material can be measured by the following method.
- the supporting base material has a spectral spectrum measured using a UV / vis spectrum meter (for example, a UV / vis spectrum meter UV3400 manufactured by Shimadzu Corporation), and is a value obtained from the measured values.
- a resin film is a preferable example of the supporting base material.
- the resin forming the supporting base material include ester resins (for example, polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polybutylene terephthalate (PBT), polycyclohexanedimethylene terephthalate (PCT), etc.), and olefin resins (for example, , Polypropylene (PP), polyethylene (PE), etc.), polyvinyl chloride (PVA), tricellulose acetate (TAC) and the like.
- PET is preferable in terms of versatility.
- the support base material is obtained by molding the above resin into a plate shape by a conventional method. Further, as the supporting base material, a commercially available resin film or the like on the market may be used. Further, it may be obtained by using the above-mentioned resin composition of the present invention.
- the thickness of the supporting base material can be appropriately selected according to the application, purpose, and the like. Generally, the thickness is preferably 5 ⁇ m to 2500 ⁇ m, more preferably 20 ⁇ m to 500 ⁇ m.
- the resin layer is a layer formed by using the resin composition.
- the resin composition the above-mentioned resin composition of the present invention can be used.
- the resin layer may be a layer that has been dried and solidified, or may be a cured layer obtained by a curing reaction.
- the thickness of the resin layer is not particularly limited and can be arbitrarily selected from the viewpoint of desired visible light transmittance.
- the thickness of the resin layer can be, for example, 5 ⁇ m to 2500 ⁇ m.
- the thickness of the resin layer is preferably 5 ⁇ m to 500 ⁇ m, more preferably 5 ⁇ m to 100 ⁇ m, particularly from the viewpoint of the function of blocking or suppressing ultraviolet rays and blue light, the easy securing of visible light transmittance, and the ease of handling.
- a peelable supporting base material peelable supporting base material (peeling laminated film) can also be used.
- An optical member using such a supporting base material is preferably used for a polarizing plate or the like.
- peelable laminated film examples include a peelable laminated film having a structure in which a support containing polyethylene terephthalate and a resin layer containing an ultraviolet absorber of the present invention are in direct contact with each other.
- the support of the peelable laminated film is a material that can be peeled from the resin layer.
- the stress when peeling the support from the resin layer is preferably 0.05 N / 25 mm or more and 2.00 N / 25 mm or less, and more preferably 0.08 N / 25 mm or more and 0.50 N / 25 mm or less. It is more preferably 0.11 N / 25 mm or more and 0.20 N / 25 mm or less.
- the stress is 0.05 N / 25 mm or more, peeling is less likely to occur during the polarizing plate processing process, and it is preferable.
- the stress is 2.00 N / 25 mm or less, polarized light is obtained when the support is peeled. This is preferable because the plate does not break.
- the stress when peeling the support of the peelable laminated film from the resin layer is that the surface of the optical film of the peelable laminated film cut into a width of 25 mm and a length of 80 mm is applied to a glass base material via an acrylic adhesive sheet.
- a tensile tester (RTF-1210 manufactured by A & D Co., Ltd.) is used to grab the base film at one end (one side with a width of 25 mm) in the length direction of the test piece and heat it.
- the support of the peelable laminated film will be described.
- the support of the peelable laminated film one containing polyethylene terephthalate (PET) is used.
- the main component of the support (the component having the highest mass-based content among the components constituting the support) is preferably polyethylene terephthalate (PET).
- PET polyethylene terephthalate
- the weight average molecular weight of PET is preferably 20,000 or more, more preferably 30,000 or more, and further preferably 40,000 or more.
- the weight average molecular weight of PET can be determined by dissolving the support in hexafluoroisopropanol (HFIP) and using the above-mentioned GPC method.
- HFIP hexafluoroisopropanol
- the thickness of the support is not particularly limited, but is preferably 0.1 to 100 ⁇ m, more preferably 0.1 to 75 ⁇ m, further preferably 0.1 to 55 ⁇ m, and 0.1. It is particularly preferably about 10 ⁇ m. Further, the support may be subjected to corona treatment, glow discharge treatment, undercoating or the like as known surface treatments.
- the peelable laminated film can be produced by applying a solution containing the ultraviolet absorber, resin, and solvent of the present invention on the support and drying it to form a resin layer.
- the solvent should be appropriately selected from the viewpoints of being able to dissolve or disperse the resin, easily forming a uniform surface in the coating process and the drying process, ensuring liquid storage stability, and having an appropriate saturated vapor pressure. Can be done.
- a hard coat layer, a transparent support base material, and a laminate having an adhesive layer or an adhesive layer laminated in this order can be mentioned.
- a laminate is preferably used as an ultraviolet cut filter or a protective material (protective film, protective sheet).
- any of the supporting base material, the hard coat layer, and the adhesive layer or the adhesive layer may contain the above-mentioned ultraviolet absorber of the present invention.
- Examples of the transparent supporting base material include those described in the first embodiment.
- the optical member of this form has a hard coat layer on the supporting base material.
- the hard coat layer may be formed by either a wet coating method or a dry coating method (vacuum film formation).
- the wet coating method is preferable in terms of excellent productivity.
- the hard coat layer is formed by using the resin composition of the present invention, it is preferably formed by a wet coating method.
- examples of the hard coat layer include JP2013-045045, JP2013-0433352, JP2012-232459, and 2012. -128157, JP2011-131409, JP2011-131404, JP2011-126162, JP2011-075705, JP2009-286981, JP2009-263567 No., JP-A-2009-075248, JP-A-2007-164206, JP-A-2006-096811, JP-A-2004-075970, JP-A-2002-156505, JP-A-2001-272503. , International Publication No. 2012/01887, International Publication No. 2012/098967, International Publication No. 2012/0866559, and International Publication No. 2011/105594 can be applied.
- the thickness of the hard coat layer is preferably 5 ⁇ m to 100 ⁇ m in terms of further improving scratch resistance.
- the optical member of this form has an adhesive layer or an adhesive layer on the side opposite to the side having the hard coat layer of the supporting base material.
- the type of the pressure-sensitive adhesive or the adhesive used for the pressure-sensitive adhesive layer or the adhesive layer is not particularly limited. Examples thereof include the above-mentioned pressure-sensitive adhesive or adhesive. Further, as the pressure-sensitive adhesive or the adhesive, those to which the above-mentioned ultraviolet absorber of the present invention is added can also be used. Further, the resin composition of the present invention described above can be used as the pressure-sensitive adhesive or the adhesive.
- the pressure-sensitive adhesive or adhesive use one containing the acrylic resin described in paragraphs 0056 to 0076 of JP-A-2017-142412 and the cross-linking agent described in paragraphs 0077-0087 of JP-A-2017-142412. Is also preferable.
- the pressure-sensitive adhesive or adhesive is the adhesion improver (silane-based compound) described in paragraph Nos. 0088 to 0097 of JP-A-2017-142912, and JP-A-2017-142412.
- the additive described in paragraph number 0098 of the publication may be included.
- the adhesive layer or the adhesive layer can be formed by the method described in paragraph Nos. 00099 to 0100 of JP-A-2017-142412.
- the thickness of the adhesive layer or the adhesive layer is preferably 5 ⁇ m to 100 ⁇ m in terms of both adhesive strength and handleability.
- the optical member of the present invention can be preferably used as a component of a display such as a liquid crystal display device (LCD) and an organic electroluminescence display device (OLED).
- a liquid crystal display device LCD
- OLED organic electroluminescence display device
- Examples of the liquid crystal display device include a liquid crystal display device containing the ultraviolet absorber of the present invention in a member such as an antireflection film, a polarizing plate protective film, an optical film, a retardation film, an adhesive, and an adhesive.
- the optical member containing the ultraviolet absorber of the present invention may be arranged on either the viewer side (front side) or the backlight side with respect to the liquid crystal cell, and the side far from the liquid crystal cell with respect to the polarizer ( It can be placed on either the outer side (outer) or the near side (inner).
- FIGS. 1 to 10 show a preferable configuration of a liquid crystal display device including an optical member containing the ultraviolet absorber of the present invention. It should be noted that FIGS. 1 to 10 are schematic views, and the relationship of thickness and positional relationship of each layer do not always match the actual ones.
- FIG. 1 is a schematic view showing a configuration in which the ultraviolet absorber of the present invention is added to the polarizing plate protective film on the front side, and FIG.
- FIG. 2 is a schematic view showing the structure in which the ultraviolet absorber of the present invention is added to the polarizing plate protective film on the backlight side. It is the schematic which shows the structure.
- FIG. 3 is a schematic view showing a configuration in which the ultraviolet absorber of the present invention is added to the inner protective film on the front side
- FIG. 4 is a configuration in which the ultraviolet absorber of the present invention is added to the inner protective film on the backlight side.
- the inner protective film can also serve as a retardation film.
- FIG. 5 is a schematic view showing a configuration in which an optical film containing the ultraviolet absorber of the present invention is bonded to a retardation film on the front side via an adhesive or an adhesive, and FIG.
- FIG. 6 is a schematic view showing a position on the backlight side. It is a schematic diagram which shows the structure which attached the optical film containing the ultraviolet absorber of this invention to the retardation film with an adhesive or an adhesive.
- FIG. 7 is a schematic view showing a configuration in which the ultraviolet absorber of the present invention is added to the adhesive or adhesive on the front side
- FIG. 8 is an ultraviolet ray of the present invention in the adhesive or adhesive on the backlight side.
- FIG. 9 is a schematic view showing a configuration in which the ultraviolet absorber of the present invention is added to the functional layer on the front side
- FIG. 10 is a configuration in which the ultraviolet absorber of the present invention is added to the functional layer on the backlight side.
- Examples of the functional layer include an antireflection layer and a hard coat layer.
- the optical member containing the ultraviolet absorber of the present invention When the optical member containing the ultraviolet absorber of the present invention is arranged on the viewer side (front side), deterioration of the material in the liquid crystal cell due to external light can be prevented.
- the ultraviolet absorber of the present invention When the ultraviolet absorber of the present invention is added to the polarizing plate protective film, it is preferable to use the above-mentioned cellulose acylate film or the resin layer in the above-mentioned peelable laminated film as the polarizing plate protective film.
- the ultraviolet absorber of the present invention When the ultraviolet absorber of the present invention is added to the polarizing plate protective film, the ultraviolet absorber of the present invention may be contained on either the side closer to the liquid crystal cell side or the side far from the liquid crystal cell, or both.
- a cellulose acylate film is used as the polarizing plate used in the liquid crystal display device.
- the polarizing plate containing the cellulose acylate film can be produced by the method described in paragraphs 0114 to 0117 of JP2012-215689A.
- the surface of the releasable laminated film opposite to the support side interface is bonded to the polarizer via an adhesive.
- the support can be peeled off to obtain a polarizing plate having a resin layer containing a polarizing element and an ultraviolet absorber of the present invention.
- the penetration depth into the resin layer containing the ultraviolet absorber is the difference in SP value (solubility parameter) between the adhesive and the resin layer containing the ultraviolet absorber, as well as the difference between the adhesive and the resin layer containing the ultraviolet absorber. It also changes depending on the aging conditions (temperature, time) after contact.
- the penetration rate can be reduced by irradiating the active energy rays once, so the durability of the polarizing plate is ensured after the penetration depth is suppressed by temporary irradiation. It is also effective to perform additional irradiation for the purpose of promoting curing.
- the surface of the resin layer containing the ultraviolet absorber of the peelable laminated film opposite to the interface on the support side may be hydrolyzed by glow discharge treatment, corona treatment, alkali saponification treatment or the like, if necessary.
- the support can be peeled off by the same method as the separator (peeling film) peeling step performed by a normal polarizing plate with an adhesive.
- the support may be peeled off immediately after the step of laminating a resin layer containing an ultraviolet absorber and a polarizer via an adhesive and drying, or once after the drying step, it is rolled into a roll. It may be taken up and peeled off separately in the subsequent process.
- Organic electroluminescence display device contains the ultraviolet absorber of the present invention in members such as an optical film, a polarizing plate protective film in a circularly polarizing plate, a retardation film such as a 1/4 wave plate, an adhesive, and an adhesive.
- An organic electroluminescence display device can be mentioned.
- a form in which the peelable laminated film is attached to a circularly polarizing plate via an adhesive or an adhesive is also preferable as a method for introducing the ultraviolet absorber of the present invention.
- FIGS. 11 to 13 show a preferable configuration of an organic electroluminescence display device including an optical member containing the ultraviolet absorber of the present invention. Note that FIGS. 11 to 13 are schematic views, and the thickness relationship and positional relationship of each layer do not always match the actual ones.
- FIG. 11 is a schematic view showing a configuration in which the ultraviolet absorber of the present invention is added to the polarizing plate protective film.
- FIG. 12 is a schematic view showing a configuration in which the ultraviolet absorber of the present invention is added to an adhesive or a pressure-sensitive adhesive.
- FIG. 13 is a schematic view showing a configuration in which an optical film containing the ultraviolet absorber of the present invention is attached to a touch panel via an adhesive or an adhesive.
- the compound of the present invention is a compound represented by the above-mentioned formula (1a).
- the compound represented by the formula (1a) has the same contents as those described in the above-mentioned section of the resin composition, and the preferable range is also the same.
- the compound represented by the formula (1a) is preferably used as an ultraviolet absorber.
- the maximum absorption wavelength of the compound represented by the formula (1a) is preferably in the wavelength range of 381 to 420 nm, and more preferably in the wavelength range of 381 to 400 nm.
- the molar extinction coefficient ⁇ 405 of the compound represented by the formula (1a) calculated from the following formula at a wavelength of 405 nm is preferably 500 or more, more preferably 1000 or more, and further preferably 2000 or more. It is particularly preferably 3000 or more.
- ⁇ 405 ⁇ max ⁇ (A 405 / A max )
- ⁇ 405 is the molar extinction coefficient of the compound represented by the formula (1a) at a wavelength of 405 nm
- ⁇ max is the molar extinction coefficient of the compound represented by the formula (1a) at the maximum absorption wavelength
- a 405 is the molar extinction coefficient of the compound represented by the formula (1a). It is the absorbance of the compound represented by 1a) at a wavelength of 405 nm
- a max is the absorbance of the compound represented by the formula (1a) at the maximum absorption wavelength.
- the ratio (A 430 / A 405 ) of the absorbance A 405 at a wavelength of 405 nm to the absorbance A 430 at a wavelength of 430 nm is less than 0.13. It is preferably 0.10 or less, and more preferably 0.10 or less. The lower limit of the above ratio is not particularly limited, but may be 0 or more.
- the compound represented by the above formula (1a) can be synthesized via a step of reacting the compound represented by the formula (2a) with an alkyl halide compound or a carboxylic acid halide.
- R 11a and R 12a each independently represent an alkyl group.
- R 14a represents an alkyl group or an alkoxy group.
- R 15a represents a hydrogen atom, an alkyl group or an alkoxy group; R 14a and R 15a may be coupled to each other to form a ring.
- R 11a , R 12a , R 14a and R 15a of the formula (2a) are synonymous with the groups described as R 11 , R 12 , R 14 and R 15 of the formula (2), and have a preferable range. The same is true.
- Examples of the alkyl halide compound to be reacted with the compound represented by the formula (2a) include a compound represented by R 30- X 30 .
- R 30 is an alkyl group and X 30 is a halogen atom.
- the number of carbon atoms of the alkyl group represented by R 30 is preferably 1 to 30, more preferably 1 to 20, further preferably 1 to 15, particularly preferably 1 to 10, and most preferably 1 to 8.
- the alkyl group may be linear or branched.
- the alkyl group may have a substituent. Examples of the substituent include the group described in Substituent T described above.
- Examples of the halogen-halogen atom represented by X 30 include a chlorine atom, a bromine atom and an iodine atom.
- Me is a methyl group
- Et is an ethyl group
- Bu is a butyl group
- tBu is a tert-butyl group
- Pr is a propyl group
- Ph is a phenyl group.
- Ac is an acetyl group.
- compound (2) -31 was synthesized according to the following synthesis scheme.
- synthesis of Intermediate 1-1 to Compound (2) -31 refer to the method described in paragraphs 0154 to 0155 of Japanese Patent No. 5376858, 1- (4,7-dihydroxybenzo [1,3].
- Dithiol-2-iriden This was done by using Intermediate 1-1 instead of Piperidinium Acetate.
- Synthesis Example 2 Synthesis of Compound (1) -2 to Compound (1) -8)
- Synthesis Example 1 Compounds (1) -2 to Compound (1) -8 were synthesized in the same manner as in Synthesis Example 1 except that the corresponding alkylating agent was used instead of 2-iodopropane.
- Example 1 Compounds listed in the table below (Compound (1) -1 to Compound (1) -16, Compound (1) -37, Compound (1) -46, Compound (1) -47, Compound (1) -48, Comparison After dissolving 2 mg of Compounds 1 to 4) in 100 mL of ethyl acetate, the sample solutions 101 to 120 were prepared by diluting with ethyl acetate so that the absorbance of the solution was in the range of 0.6 to 1.2. Compounds having the following structures were used as the comparative compounds 1 to 4.
- the absorbance of each of the sample solutions 101 to 120 was measured in a 1 cm quartz cell using a spectrophotometer UV-1800PC (manufactured by Shimadzu Corporation).
- the maximum absorption wavelength ( ⁇ max ) was measured from the spectrum chart obtained for each sample solution. The values of ⁇ max are shown in the table below.
- ⁇ 405 ⁇ max ⁇ (A 405 / A max )
- ⁇ 405 is the molar absorbance coefficient of the sample solution at a wavelength of 405 nm
- ⁇ max is the molar absorbance coefficient of the sample solution at the maximum absorption wavelength
- a 405 is the absorbance of the sample solution at a wavelength of 405 nm
- a max is the sample solution of the sample solution. Absorbance at the maximum absorption wavelength.
- a value of ⁇ 405 of 3000 or more was evaluated as A, a value of less than 3000 and 500 or more was evaluated as B, and a value of less than 500 was evaluated as C on a three-point scale.
- the evaluation results are shown in the column of ⁇ 405 in Table 1 below.
- the value of the absorbance at the wavelength of 430 nm is calculated when the absorbance of the sample solution at the wavelength of 405 nm is 1, and the absorbance at the wavelength of 430 nm is less than 0.13, A is defined as A, and 0.13 or more is defined as B for coloring. evaluated. The smaller the absorbance value at a wavelength of 430 nm, the less coloring it means. The results are shown in the coloring column of Table 1 below.
- compounds (1) -1 to (1) -16, compound (1) -37, compound (1) -46, compound (1) -47, and compound (1) -48 have wavelengths.
- the molar extinction coefficient ( ⁇ 405 ) at 405 nm was high, and there was little coloring.
- Example 2-1> The compounds listed in the table below, 7.6 g of chloroform, and 1.1 g of (meth) acrylic resin (Dianal BR-80, Mitsubishi Chemical Co., Ltd., containing 60% by mass or more of methyl methacrylate as a monomer unit, Mw95000). And were mixed to prepare a resin composition. The obtained resin composition was spin-coated on a glass substrate to form a coating film, and the obtained coating film was dried at 110 ° C. for 2 minutes to prepare a resin film. In addition, compound (1) -1, compound (1) -2, compound (1) -8, compound (1) -11, compound (1) -12, compound described in the column of compound type of Table 2 below.
- the resin film produced above was subjected to a light resistance test under the following condition 1, the retention rate of absorbance at the maximum absorption wavelength ( ⁇ max ) was determined, and the light resistance was evaluated. Specifically, after measuring the absorbance at the maximum absorption wavelength ( ⁇ max ) of the resin film, the resin film was subjected to a light resistance test for one week under condition 1, and the maximum absorption wavelength of the resin film after the light resistance test ( ⁇ max). The absorbance at ⁇ max ) was measured.
- the absorbance maintenance rate (%) was calculated from the value of the absorbance at the maximum absorption wavelength ( ⁇ max ) of the resin film before and after the light resistance test from the following formula.
- the maintenance rate was calculated according to the following formula.
- Retention absorbance (%) 100 ⁇ (absorbance at lambda max of the resin film after irradiation) / (absorbance at lambda max of the resin film before irradiation)
- C Absorbance maintenance rate is less than 80%
- the resin films 201a to 212a absorbed more light in the vicinity of the wavelength of 400 nm than the resin films 213a to 216a, and were excellent in the absorption of ultraviolet rays on the long wavelength side. Further, the resin films 201a to 212a were less colored. That is, the resin films 201a to 212a absorbed a large amount of light in the vicinity of a wavelength of 400 nm and were less colored.
- the resin films 201a to 212a had less surface unevenness and were also excellent in light resistance.
- the resin composition used for forming the resin films 20a1 to 212a contains the compound (2) (compound represented by the formula (2)) described in the present specification described above to form the resin composition. Storage stability was improved, and for example, precipitation of compound (1) was not observed even when a resin film was formed using the resin composition after storage at 5 ° C. for 2 weeks.
- ⁇ Test Example 2-2> The compounds listed in the table below, 7.6 g of chloroform, and 1.1 g of (meth) acrylic resin (Dianal BR-80, Mitsubishi Chemical Co., Ltd., containing 60% by mass or more of methyl methacrylate as a monomer unit, Mw95000). And were mixed to prepare a resin composition. The obtained resin composition was spin-coated on a glass substrate to form a coating film, and the obtained coating film was dried at 110 ° C. for 2 minutes to prepare a resin film.
- compound (1) -1, compound (1) -5, and compound (1) -8 are compounds having the above-mentioned structures, respectively.
- UV-1 to UV-6 are compounds having the following structures.
- the resin film produced above was subjected to a light resistance test under condition 1 of Test Example 2-1 to determine the retention rate of absorbance at a wavelength of 405 nm, and the light resistance 2 was evaluated. Specifically, after measuring the absorbance of the resin film at a wavelength of 405 nm, the resin film was subjected to a light resistance test under condition 1 for one week, and the absorbance of the resin film after the light resistance test at a wavelength of 405 nm was measured. The absorbance maintenance rate (%) was calculated from the value of the absorbance of the resin film at 405 nm before and after the light resistance test from the following formula. The maintenance rate was calculated according to the following formula.
- Absorbance retention rate (%) 100 ⁇ (absorbance of the resin film after irradiation at a wavelength of 405 nm) / (absorbance of the resin film before irradiation at a wavelength of 405 nm)
- the resin films 201b to 206b absorbed a large amount of light in the vicinity of a wavelength of 400 nm, and were excellent in absorbing ultraviolet rays on the long wavelength side. In addition, the maintenance rate of the absorbance at 405 nm after the light resistance test was also good, and the light resistance was excellent.
- the resin film 301 was produced by the method shown below.
- (1) Preparation of raw materials (1-1) Preparation of cellulose acylate A cellulose acylate having an acetyl substitution degree of 2.85 was prepared. Sulfuric acid (7.8 parts by mass with respect to 100 parts by mass of cellulose) was added as a catalyst, and each carboxylic acid was added to carry out an acylation reaction at 40 ° C. Then, the total substitution degree and the 6-position substitution degree were adjusted by adjusting the amount of sulfuric acid catalyst, the amount of water and the aging time. The aging temperature was 40 ° C. Further, the low molecular weight component of this cellulose acylate was washed with acetone to remove it.
- sugar ester compound 1 having the following structure was synthesized by the method described in Synthesis of Example Compound 3 in Paragraph No. 0054 of International Publication No. 2009/003164. Further, the sugar ester compound 2 was also synthesized by the same method.
- Dope preparation The following composition is put into a mixing tank, stirred to dissolve each component, further heated to 80 ° C. for about 180 minutes, and then filtered with a filter paper having an average pore size of 34 ⁇ m and a sintered metal filter having an average pore size of 10 ⁇ m. Filtered.
- the solid content concentration of the dope is 16.0% by mass
- the amount of the plasticizer added is all the ratio to the cellulose ester
- the film thickness is 60 ⁇ m.
- the specific structure of the sugar ester is shown below.
- the amount of the sugar ester 1 added was 7.5% by mass, and the sugar ester 1 having the following structure with an average degree of substitution of 5.5 was used.
- the degree of substitution was calculated by HPLC (High Performance Liquid Chromatography).
- the amount of the sugar ester 2 added is 2.5% by mass, and the amount of the compound (1) -5 is 0.1% by mass.
- the doping of each of the other Examples and Comparative Examples was prepared in the same manner as the doping of the resin film 301A except that the addition amounts of the ultraviolet absorber 1 and the ultraviolet absorber 2 were changed.
- the above-mentioned dope was cast using a drum film forming machine.
- the dope of the core layer was co-cast from the die so that the dope of the surface layer was on the dope of the core layer so as to be in contact with the metal support cooled to ⁇ 10 ° C., gelled and peeled off.
- the drum was made of stainless steel.
- the web (film) obtained by casting is peeled off from the drum, and then inside the tenter device using a tenter device that clips and conveys both ends of the web at 30 to 40 ° C. during film transfer. It was dried for 20 minutes. Then, the dried product was framed and post-dried at 140 ° C.
- the drying temperature referred to here means the film surface temperature of the film.
- Winding A film having the composition shown in the table below was prepared, and at least 24 rolls having a roll width of 1280 mm and a roll length of 2600 mm were prepared for the purpose of determining the production suitability thereof. For one of the 24 rolls produced continuously, a sample (width 1280 mm) having a length of 1 m was cut out at intervals of 100 m and each measurement was performed. The obtained cellulose acylate films were used as resin films 301 to 309 of each Example and Comparative Example.
- the absorbance of each of the resin films 301A to 309A prepared above was measured using a spectrophotometer UV3600 (manufactured by Shimadzu Corporation).
- the value obtained by dividing the absorbance at a wavelength of 405 nm by the amount of the ultraviolet absorber added is A for 50 or more, B for 25 to 50, and C for 25 or less, and the long-wavelength ultraviolet absorption ability.
- the results are shown in the column of long wavelength UV absorption capacity in the table below.
- Compounds (1) -5 used as the ultraviolet absorber 1 are compounds having the above-mentioned structure. Further, the comparative compound 5 used as the ultraviolet absorber 2 is a compound having the following structure.
- the resin films 301A to 306A absorbed more light in the vicinity of the wavelength of 400 nm than the resin films 307A to 309A, and were excellent in the absorption of ultraviolet rays on the long wavelength side.
- polarizing plate was prepared by the method shown below. (6-1) Saponification Treatment of Resin Films The prepared resin films 303A, 304A, and 308A were immersed in a 2.3 mol / L sodium hydroxide aqueous solution at 55 ° C. for 3 minutes. It was washed in a water washing bath at room temperature (25 ° C.) and neutralized at 30 ° C. with 0.05 mol / L sulfuric acid. It was washed again in a water washing bath at room temperature, and further dried with warm air at 100 ° C.
- VA Vertical Alignment
- VA retardation film 2 was used as the phase difference film.
- ⁇ Preparation of fine particle dispersion 11 parts by mass of fine particles (Aerosil R812 manufactured by Nippon Aerosil Co., Ltd.) and 89 parts by mass of ethanol were stirred and mixed with a dissolver for 50 minutes and then dispersed with manton gorin to prepare a fine particle dispersion.
- ⁇ Preparation of fine particle additive solution 4 parts by mass of cycloolefin polymer A was added to a dissolution tank containing 99 parts by mass of methylene chloride, heated to completely dissolve it, and then 11 parts by mass of the fine particle dispersion was added while sufficiently stirring. was slowly added and dispersed with an attritor. This was filtered with a filter (Finemet NF manufactured by Nippon Seisen Co., Ltd.) to prepare a fine particle additive solution.
- a filter Feinemet NF manufactured by Nippon Seisen Co., Ltd.
- ⁇ Preparation of VA retardation film 1> First, methylene chloride and methanol were added to the pressurized dissolution tank. The cycloolefin polymer A was put into a pressure dissolution tank containing a solvent with stirring. This was heated and completely dissolved with stirring to prepare a main doping solution. Add 2 parts by mass of the fine particle addition liquid to 100 parts by mass of the main doping liquid, mix thoroughly with an in-line mixer (Toray static in-tube mixer Hi-Mixer, SWJ), and then use a belt casting device to make stainless steel with a width of 2 m. It was evenly spread over the band support.
- an in-line mixer Toray static in-tube mixer Hi-Mixer, SWJ
- the solvent was evaporated until the residual solvent amount became 110% by mass, and the web (film) was peeled off from the stainless band support. After peeling, tension was applied to stretch the material so that the longitudinal stretching ratio was 2%. Then, the film was dried until the amount of residual solvent in the film was less than 1% by mass, and then further stretched by 35% at 165 ° C. in the direction orthogonal to the film transport direction using a tenter.
- the amount of residual solvent was calculated according to the following formula.
- Residual solvent amount (mass%) ⁇ (MN) / N ⁇ x 100
- M is the mass of the web at an arbitrary time point
- N is the mass of the web on which M is measured when the web is dried at 120 ° C. for 2 hours.
- a VA retardation film 1 having a width of 1.5 m, a width of 1 cm and a height of 8 ⁇ m at the end, a film thickness of 35 ⁇ m, and an Rth of 121 nm was produced.
- Additive A was synthesized by a method similar to or similar to the method described in Japanese Patent No. 6095766.
- the structural formula of the synthesized compound is shown below.
- Additive B was synthesized by a method similar to or similar to the method described in WO2015/005398. The structural formula of the synthesized compound is shown below.
- Additive C was synthesized by a method similar to or similar to the method described in Japanese Patent No. 4260332. The structural formula of the synthesized compound is shown below.
- composition of Doping for Core Layer Formation Cellulose acetate (degree of substitution 2.4) ⁇ ⁇ ⁇ 100.0 parts by mass Additive A ⁇ ⁇ ⁇ 12.0 parts by mass Additive B ⁇ ⁇ ⁇ 3.5 parts by mass Additive C ⁇ ⁇ ⁇ 1.0 part by mass Methylene chloride ⁇ ⁇ 392.0 parts by mass Methanol ⁇ ⁇ ⁇ 58.5 parts by mass
- composition of Doping for Skin Layer Formation Cellulose acetate (degree of substitution 2.8) ⁇ ⁇ ⁇ 100 parts by mass Methylene chloride ⁇ ⁇ ⁇ 440 parts by mass Methanol ⁇ ⁇ ⁇ 65.8 parts by mass
- the prepared core layer forming dope and skin layer forming dope were co-spread in three layers so as to stack the skin layer, the core layer, and the skin layer in this order.
- the film thickness of the core layer after drying was 39 ⁇ m, and the film thickness of each skin layer was 1 ⁇ m.
- the obtained film (web) was peeled off from the band, sandwiched between clips, and when the amount of residual solvent with respect to the total mass of the film was 20 to 5% by mass, a tenter was used to draw 1.1 times at 140 ° C. It was stretched laterally (stretched in the width direction). After that, the clip was removed from the film, dried at 140 ° C.
- the loss direct contact tan ⁇ is the following conditions for a film sample that has been preliminarily adjusted to a humidity of 25 ° C.
- Residual solvent amount (mass%) ⁇ (MN) / N ⁇ x 100 M is the mass of the web at an arbitrary time point, and N is the mass of the web on which M is measured when the web is dried at 120 ° C. for 2 hours.
- VA retardation film 1 and polarizer ⁇ Adhesion of VA retardation film 1 and polarizer>
- the above VA retardation film 1 is attached to one side of the polarizing element using an ultraviolet curable adhesive 1, and after 5 seconds, ultraviolet rays are irradiated from the VA retardation film 1 side at an intensity of 200 mJ to obtain an ultraviolet curable adhesive. 1 was cured to obtain a VA retardation film 1 with a polarizer.
- the liquid crystal display devices 303C1, 303C2, 304C1 and 304C2 containing the ultraviolet absorber of the present invention were preferred because the change in image quality was small even during long-term display as compared with the liquid crystal display devices 308C1 and 308C2.
- composition of cellulose acylate solution Cellulose acetate (degree of acetylation 2.86) ⁇ ⁇ ⁇ 100 parts by mass Methylene chloride (first solvent) ⁇ ⁇ ⁇ 320 parts by mass Methanol (second solvent) ⁇ ⁇ ⁇ 83 parts by mass 1-butanol (third solvent) ⁇ . ⁇ ⁇ 3 parts by mass Triphenyl phosphate ⁇ ⁇ ⁇ 7.6 parts by mass Biphenyldiphenyl phosphate ⁇ ⁇ ⁇ 3.8 parts by mass
- composition of matting agent dispersion Silica particle dispersion (average particle size 16 nm, AEROSIL R972, manufactured by Nippon Aerosil Co., Ltd. ⁇ ⁇ ⁇ 10.0 parts by mass Methylene chloride ⁇ ⁇ ⁇ 72.8 parts by mass Methanol ⁇ ⁇ ⁇ 3.9 parts by mass Butanol ⁇ ⁇ ⁇ 0.5 parts by mass Cellulosilate solution ⁇ ⁇ ⁇ 0.3 parts by mass
- UV absorber Compound having a structure represented by the formula (UV-11)
- UV absorber compound having a structure represented by the formula (UV-12)
- UV absorber compound having a structure represented by the formula (UV-12)
- Methylene chloride ⁇ ⁇ ⁇ 55.7 parts by mass Methanol ⁇ ⁇ ⁇ 10 parts by mass Butanol ⁇ ⁇ ⁇ 1.3 parts by mass Cellulose acylate solution ⁇ ⁇ ⁇ 12.9 parts by mass
- An ultraviolet absorber solution was added so that each of (UV-2) was 1.0 part by mass, and each component was dissolved by sufficiently stirring while heating to prepare a dope.
- the obtained dope was heated to 30 ° C. and cast on a mirror-finished stainless steel support, which is a drum having a diameter of 3 m, through a casting geser.
- the surface temperature of the mirror-finished stainless steel support was set to ⁇ 5 ° C., and the coating width was 1470 mm.
- the cast dope film was dried by applying a drying air at 34 ° C. on the drum at 150 m 3 / min, and the dope film was peeled off from the drum with a residual solvent of 150%.
- stretching was performed by 15% in the transport direction (longitudinal direction). After that, both ends of the film in the width direction (direction orthogonal to the casting direction) are conveyed while being gripped by a pin tenter (pin tenter described in FIG. 3 of JP-A-04-00109), and stretched in the width direction. No processing was performed.
- the film was further dried by being conveyed between the rolls of the heat treatment apparatus to produce a cellulose acylate film (T1).
- the produced long cellulose acylate film (T1) has a residual solvent amount of 0.2%, a thickness of 60 ⁇ m, and Re (in-plane retardation) and Rth (thickness direction retardation) at a wavelength of 550 nm are 0, respectively. It was 0.8 nm and 40 nm.
- Alkaline saponification treatment After passing the above-mentioned cellulose acylate film (T1) through a dielectric heating roll having a temperature of 60 ° C. and raising the film surface temperature to 40 ° C., an alkaline solution having the composition shown below is applied to the band surface of the film. It was applied using a coater at a coating amount of 14 ml / m 2 . Then, the cell roll acylate film coated with the alkaline solution was conveyed for 10 seconds under a steam-type far-infrared heater manufactured by Noritake Co., Ltd. Limited, which was heated to 110 ° C.
- composition of alignment film coating liquid Modified polyvinyl alcohol with the following structure: 10 parts by mass Water: 308 parts by mass Methanol: 70 parts by mass Isopropanol: 29 parts by mass Photopolymerization initiator (Omnirad 2959, manufactured by IGM Resins BV) ⁇ ⁇ ⁇ 0.8 parts by mass
- the alignment film prepared above was continuously subjected to a rubbing treatment.
- the longitudinal direction of the long film and the conveying direction are parallel, and the angle between the longitudinal direction of the film (the conveying direction) and the rotation axis of the rubbing roller is 72.5 ° (the longitudinal direction of the film (the conveying direction).
- the counterclockwise direction is represented by a positive value with respect to the film width direction as a reference (0 °) when observed from the alignment film side.
- the rotation axis of the rubbing roller is -17.5 °.
- the position of the rotation axis of the rubbing roller corresponds to the position rotated by 72.5 ° counterclockwise with respect to the longitudinal direction of the film.
- the optically anisotropic layer coating liquid (A) containing the discotic liquid crystal (DLC) compound having the following composition was continuously coated on the above-prepared alignment film with a # 5.0 wire bar.
- the transport speed (V) of the film was set to 26 m / min.
- the coating film was irradiated with UV (ultraviolet rays) at 80 ° C. (exposure amount: 70 mJ / cm 2 ) to fix the orientation of the liquid crystal compound.
- the thickness of the optically anisotropic layer A was 2.0 ⁇ m.
- the average inclination angle of the disk surface of the DLC compound with respect to the film surface was 90 °, and it was confirmed that the DLC compound was oriented perpendicularly to the film surface.
- the angle of the slow axis is parallel to the rotation axis of the rubbing roller, and the film longitudinal direction (conveyance direction) is 90 ° (the film width direction is 0 °.
- the film width direction is used as a reference (0 °) when observed from the alignment film side. ) Is represented by a positive value in the counterclockwise direction.), It was -17.5 °.
- the obtained optically anisotropic layer A corresponds to a ⁇ / 2 plate, and Re and Rth at a wavelength of 550 nm were Re (550): 238 nm and Rth (550): -119 nm, respectively.
- Polymer A Resin with the following structure
- Polymer B Resin having the following structure (in the structural formula, a represents 90 and b represents 10).
- Polymer C Resin with the following structure
- the optically anisotropic layer coating liquid (B) containing the discotic liquid crystal compound having the following composition was continuously coated on the alignment film after the rubbing treatment with a # 2.8 wire bar.
- the transport speed (V) of the film was set to 26 m / min.
- the coating film is heated with warm air at 60 ° C. for 60 seconds, and then the obtained coating film is irradiated with UV at 60 ° C. to discotic.
- the orientation of the liquid crystal compound was fixed.
- the thickness of the optically anisotropic layer B was 0.8 ⁇ m.
- the average inclination angle of the discotic liquid crystal compound with respect to the film surface on the long axis was 90 °, and it was confirmed that the discotic liquid crystal compound was oriented perpendicularly to the film surface.
- the angle of the slow-phase axis is orthogonal to the rotation axis of the rubbing roller, and the film longitudinal direction is 90 ° (the film width direction is 0 °. Observed from the alignment film side, the film width direction is counterclockwise (0 °). When the rotation direction is represented by a positive value), it was 102.5 ° (-77.5 °).
- the obtained optically anisotropic layer B corresponded to a ⁇ / 4 plate, and Re (550) was 118 nm and Rth (550) was ⁇ 59 nm.
- Polarizer A polyvinyl alcohol (PVA) film having a thickness of 80 ⁇ m is immersed in an aqueous iodine solution having an iodine concentration of 0.05% by mass at 30 ° C. for 60 seconds for dyeing, and then a boric acid concentration of 4% by mass. While immersed in a% boric acid aqueous solution for 60 seconds, it was longitudinally stretched to 5 times the original length and then dried at 50 ° C. for 4 minutes to obtain a polarizer having a thickness of 19 ⁇ m.
- PVA polyvinyl alcohol
- the resin film 303A saponified above was attached to one side of the polarizer prepared above using a polyvinyl alcohol-based adhesive to prepare a polarizing plate.
- a pressure-sensitive adhesive (SK-2057, manufactured by Soken Kagaku Co., Ltd.) is applied to the polarizer (without resin film 303A) side of the above-mentioned prepared polarizing plate to apply a pressure-sensitive adhesive layer.
- the prepared cellulose acylate film, the alignment film, and the film having the optically anisotropic layer A were bonded together so that the pressure-sensitive adhesive layer and the optically anisotropic layer A were in close contact with each other. Then, the cellulose acylate film and the alignment film were peeled off to obtain a laminate.
- an adhesive (SK-2057, manufactured by Soken Chemical Co., Ltd.) was applied to the optically anisotropic layer A in the obtained laminate to form an adhesive layer.
- the pressure-sensitive adhesive layer and the optically anisotropic layer B adhere to the laminate on which the pressure-sensitive adhesive layer is arranged and the film having the cellulose acylate film, the alignment film, and the optically anisotropic layer B prepared above. It was pasted together so as to do. Then, the cellulose acylate film and the alignment film were peeled off.
- the angle formed by the slow axis of the optically anisotropic layer A ( ⁇ / 2 plate) and the transmission axis of the polarizer is 17.5 °, and the delay of the optically anisotropic layer A ( ⁇ / 2 plate).
- the angle formed by the phase axis and the slow axis of the optically anisotropic layer B ( ⁇ / 4 plate) was 60 °.
- the organic electroluminescence display devices 303E and 304E containing the ultraviolet absorber of the present invention were preferred as compared with the organic electroluminescence display device 308E because there was little change in image quality even during long-term display.
- An optical film 401A was formed on the base film by the method shown below to prepare a peelable laminated film 401B.
- (1) Preparation of coating liquid A coating liquid 1 for forming the optical film 401A was prepared with the composition shown below. The obtained coating liquid was filtered through a filter having an absolute filtration accuracy of 5 ⁇ m.
- composition of coating liquid 1 AS-70 (acrylonitrile / styrene copolymer resin, manufactured by Nippon Steel & Sumikin Chemical Co., Ltd.) ⁇ ⁇ ⁇ 100.0 parts by mass Byron 500 (polyester resin, manufactured by Toyo Boseki Co., Ltd.) ⁇ ⁇ ⁇ 0.9 parts by mass SMA2000P (styrene) ⁇ Maleic acid copolymer, Kawahara Yuka Co., Ltd.) ⁇ ⁇ ⁇ 4.2 parts by mass Styrene 1 ⁇ ⁇ ⁇ 0.1 parts by mass Ultraviolet absorber (Compound (1) -5) ⁇ ⁇ ⁇ 3.
- Surfactant 1 Compound with the following structure
- Compounds (1) -5 and comparative compound 5 used as ultraviolet absorbers are compounds having the above-mentioned structures, respectively.
- Coating liquids 2 to 6 were prepared in the same manner as in coating liquid 1 except that the addition amounts of compound (1) -5 and comparative compound 5 were changed as shown in the table below.
- the coating liquid 1 is applied onto the base film under the condition of a transport speed of 30 m / min by the die coating method using the slot die described in Example 1 of JP-A-2006-122889, and the temperature is 105 ° C. It was dried for 30 seconds. Then it was wound up.
- the obtained peelable laminated films were designated as the peelable laminated films 401B to 406B of each Example and Comparative Example.
- the absorbance of each of the peelable laminated films 401B to 406B prepared above was measured using a spectrophotometer UV3600 (manufactured by Shimadzu Corporation). Further, the value obtained by dividing the absorbance at a wavelength of 405 nm by the amount of the ultraviolet absorber added (mass% with respect to AS-70) is 50 or more as A, 25 to 50 as B, and 25 or less as C, and the long wavelength ultraviolet absorption ability. was evaluated. The larger the value, the higher the ability to absorb ultraviolet rays of long wavelengths. The results are shown in the column of long wavelength UV absorption capacity in the table below.
- the peelable laminated films 401B to 403B absorbed more light near the wavelength of 400 nm than the peelable laminated films 404B to 406B, and were excellent in absorbing ultraviolet rays on the long wavelength side.
- Polarizing Plate A polarizing plate was prepared by the method shown below. (3-1) Saponification Treatment of Polarizing Plate Protective Film A 60 ⁇ m triacetyl cellulose film (Fujitac TG60, manufactured by FUJIFILM Corporation) was immersed in a 2.3 mol / L sodium hydroxide aqueous solution at 55 ° C. for 3 minutes. It was washed in a water washing bath at room temperature (25 ° C.) and neutralized at 30 ° C. with 0.05 mol / L sulfuric acid. It was washed again in a water washing bath at room temperature, and further dried with warm air at 100 ° C.
- 3-1 Saponification Treatment of Polarizing Plate Protective Film A 60 ⁇ m triacetyl cellulose film (Fujitac TG60, manufactured by FUJIFILM Corporation) was immersed in a 2.3 mol / L sodium hydroxide aqueous solution at 55 ° C. for 3 minutes. It was washed in a water
- Polarizing plate 4C1 was produced in the same manner as the polarizing plate 303B1 except that the above 60 ⁇ m triacetyl cellulose film was used instead of the resin film 303A.
- Polarizing plate 4C2 was produced in the same manner as the polarizing plate 303B2 except that the above 60 ⁇ m triacetyl cellulose film was used instead of the resin film 303A.
- the liquid crystal display devices 402E1 and 402E2 containing the ultraviolet absorber of the present invention were preferred as compared with the liquid crystal display devices 405E1 and 405E2 because the change in image quality was small even during long-term display.
- Adhesive 501 was prepared by the method shown below. (1) Preparation of coating liquid
- composition of coating liquid 1 Acrylic resin (SK Dyne-SF2147) ⁇ ⁇ ⁇ 100.0 parts by mass Polymerizable compound (TD-75) ⁇ ⁇ ⁇ 0.04 parts by mass silane coupling agent (A-50) ⁇ ⁇ ⁇ 0.06 parts by mass Ultraviolet rays Absorbent (Compound (1) -5) ⁇ ⁇ ⁇ 0.2 parts by mass UV absorber (Comparative compound 5) ⁇ ⁇ ⁇ 0.0 parts by mass
- the materials used are shown below.
- the compounds (1) -5 and the comparative compound 5 used as the ultraviolet absorbers are compounds having the above-mentioned structures, respectively.
- SK Dyne-SF2147 Acrylic acid ester copolymer. Solid content concentration 10 to 20% by mass, ethyl acetate, butyl acrylate solvent (Soken Chemical Co., Ltd.)
- TD-75 Trimethylolpropane-imparted body of tolylene diisocyanate (Soken Chemical Co., Ltd.)
- A-50 Organosilane (Soken Chemical Co., Ltd.)
- Coating liquids 2 to 6 were prepared in the same manner as in coating liquid 1 except that the addition amounts of compound (1) -5 and comparative compound 5 were changed as shown in the table below.
- the peelable laminated films 501B to 503B absorbed more light near the wavelength of 400 nm than the peelable laminated films 504B to 506B, and were excellent in absorbing ultraviolet rays on the long wavelength side.
- liquid crystal display devices 502C1, 505C1, 502C2, 505C2 Take out the liquid crystal panel of the commercially available liquid crystal display device FlexScan 19-inch color liquid crystal monitor S1923-HBK (trade name, manufactured by EIZO Co., Ltd.) and use the polarizing plate on the backlight side. Was peeled off, and instead, the VA retardation film side of the polarizing plate 4C1 was attached via the pressure-sensitive adhesive sheet 502A. In this way, the liquid crystal display device 502C1 was manufactured. Further, the liquid crystal display devices 505C1, 502C2, and 505C2 were manufactured in the same manner except that the type of the pressure-sensitive adhesive sheet and the type of the polarizing plate were changed.
- the liquid crystal display devices 502C1 and 502C2 containing the ultraviolet absorber of the present invention were preferred as compared with the liquid crystal display devices 505C1 and 505C2 because the change in image quality was small even during long-term display.
- Liquid crystal display device 11 to 13 Organic electroluminescence display device 22, 49, 176: Polarizing plate protective film containing an ultraviolet absorber of the present invention 56, 75: Inner protective film containing an ultraviolet absorber of the present invention (phase difference) film) 88, 107, 206: Optical member (optical film) containing an ultraviolet absorber of the present invention.
- Adhesive or adhesive containing UV absorber of the present invention 145, 174: Functional layer containing UV absorber of the present invention 21, 35, 36, 50, 51, 65, 66, 80, 81, 97, 98, 114, 115, 129, 130, 144, 159, 160, 175, 186, 197: Functional layers 23, 25, 27, 29, 31, 33, 38, 40, 42, 44, 46, 48 , 53, 55, 57, 59, 61, 63, 68, 70, 72, 74, 76, 78, 83, 85, 87, 89, 91, 93, 95, 100, 102, 104, 106, 108, 110 , 112, 117, 119, 123, 125, 127, 132, 134, 136, 140, 142, 147, 149, 151, 153, 155, 157, 162, 164, 166, 168, 170, 172, 177, 179.
Abstract
Description
<1> 式(1)で表される化合物と、樹脂とを含む樹脂組成物;
R3およびR6は、各々独立にアルコキシ基、アシルオキシ基、カルバモイルオキシ基またはアルコキシカルボニルオキシ基を表し、
R4は、アルキル基、アリール基、アルコキシ基、アリールオキシ基、アシルオキシ基、アルキルアミノ基、アニリノ基、アシルアミノ基、アルキルスルホニルアミノ基、アリールスルホニルアミノ基、アルキルチオ基またはアリールチオ基を表し、
R5は、水素原子、アルキル基、アリール基、アルコキシ基、アリールオキシ基、アシルオキシ基、アルキルアミノ基、アニリノ基、アシルアミノ基、アルキルスルホニルアミノ基、アリールスルホニルアミノ基、アルキルチオ基またはアリールチオ基を表す;
R1とR2は互いに結合して環を形成していてもよい;
R3とR4は互いに結合して環を形成していてもよい;
R4とR5は互いに結合して環を形成していてもよい;
R5とR6は互いに結合して環を形成していてもよい;
ただし、R3およびR6がそれぞれ独立にアシルオキシ基またはカルバモイルオキシ基の場合、R4およびR5の少なくとも一方は、アリール基、アルコキシ基、アリールオキシ基、アシルオキシ基、アルキルアミノ基、アニリノ基、アシルアミノ基、アルキルスルホニルアミノ基、アリールスルホニルアミノ基、アルキルチオ基またはアリールチオ基である。
<2> 式(1)中、R4はアルキル基、アリール基、アルコキシ基またはアリールオキシ基であり、R5は水素原子、アルキル基、アリール基、アルコキシ基またはアリールオキシ基である、<1>に記載の樹脂組成物。
<3> 式(1)中、R3およびR6の少なくとも一方はアルコキシ基である、<1>または<2>に記載の樹脂組成物。
<4> 上記式(1)で表される化合物が、下記式(1a)で表される化合物である、<1>に記載の樹脂組成物;
R3aおよびR6aは、各々独立にアルコキシ基またはアシルオキシ基を表し、
R4aはアルキル基またはアルコキシ基を表し、
R5aは、水素原子、アルキル基またはアルコキシ基を表す;
R1aとR2aは互いに結合して環を形成していてもよい;
R3aとR4aは互いに結合して環を形成していてもよい;
R4aとR5aは互いに結合して環を形成していてもよい;
R5aとR6aは互いに結合して環を形成していてもよい;
ただし、R3aおよびR6aがアシルオキシ基の場合、R4aおよびR5aの少なくとも一方はアルコキシ基である。
<5> 更に、式(2)で表される化合物を含む、<1>~<4>のいずれか1つに記載の樹脂組成物;
R13およびR16は、各々独立にヒドロキシ基、アルコキシ基、アリールオキシ基、アシルオキシ基、カルバモイルオキシ基、アルコキシカルボニルオキシ基、アリールオキシカルボニルオキシ基、スルフィニルオキシ基またはスルホニルオキシ基を表し、
R14はアルキル基、アリール基、アルコキシ基、アリールオキシ基、アシルオキシ基、アルキルアミノ基、アニリノ基、アシルアミノ基、アルキルスルホニルアミノ基、アリールスルホニルアミノ基、アルキルチオ基またはアリールチオ基を表し、
R15は水素原子、アルキル基、アリール基、アルコキシ基、アリールオキシ基、アシルオキシ基、アルキルアミノ基、アニリノ基、アシルアミノ基、アルキルスルホニルアミノ基、アリールスルホニルアミノ基、アルキルチオ基またはアリールチオ基を表す;
R11とR12は互いに結合して環を形成していてもよい;
R13とR14は互いに結合して環を形成していてもよい;
R14とR15は互いに結合して環を形成していてもよい;
R15とR16は互いに結合して環を形成していてもよい;
ただし、R13およびR16の少なくとも一方はヒドロキシ基である。
<6> 更に、上記式(1)で表される化合物以外の他の紫外線吸収剤を含む、<1>~<5>のいずれか1つに記載の樹脂組成物。
<7> 上記樹脂が、(メタ)アクリル樹脂、ポリスチレン樹脂、ポリエステル樹脂、ポリウレタン樹脂、ポリチオウレタン樹脂、ポリイミド樹脂、エポキシ樹脂、ポリカーボネート樹脂およびセルロースアシレート樹脂から選ばれる少なくとも1種である、<1>~<6>のいずれか1つに記載の樹脂組成物。
<8> <1>~<7>のいずれか1つに記載の樹脂組成物を用いて得られる硬化物。
<9> 式(1)で表される化合物を含む紫外線吸収剤;
R3およびR6は、各々独立にアルコキシ基、アシルオキシ基、カルバモイルオキシ基またはアルコキシカルボニルオキシ基を表し、
R4は、アルキル基、アリール基、アルコキシ基、アリールオキシ基、アシルオキシ基、アルキルアミノ基、アニリノ基、アシルアミノ基、アルキルスルホニルアミノ基、アリールスルホニルアミノ基、アルキルチオ基またはアリールチオ基を表し、
R5は、水素原子、アルキル基、アリール基、アルコキシ基、アリールオキシ基、アシルオキシ基、アルキルアミノ基、アニリノ基、アシルアミノ基、アルキルスルホニルアミノ基、アリールスルホニルアミノ基、アルキルチオ基またはアリールチオ基を表す;
R1とR2は互いに結合して環を形成していてもよい;
R3とR4は互いに結合して環を形成していてもよい;
R4とR5は互いに結合して環を形成していてもよい;
R5とR6は互いに結合して環を形成していてもよい;
ただし、R3およびR6がそれぞれ独立にアシルオキシ基またはカルバモイルオキシ基の場合、R4およびR5の少なくとも一方は、アリール基、アルコキシ基、アリールオキシ基、アシルオキシ基、アルキルアミノ基、アニリノ基、アシルアミノ基、アルキルスルホニルアミノ基、アリールスルホニルアミノ基、アルキルチオ基またはアリールチオ基である。
<10> 更に、式(2)で表される化合物を含む、<9>に記載の紫外線吸収剤;
R13およびR16は、各々独立にヒドロキシ基、アルコキシ基、アリールオキシ基、アシルオキシ基、カルバモイルオキシ基、アルコキシカルボニルオキシ基、アリールオキシカルボニルオキシ基、スルフィニルオキシ基またはスルホニルオキシ基を表し、
R14はアルキル基、アリール基、アルコキシ基、アリールオキシ基、アシルオキシ基、アルキルアミノ基、アニリノ基、アシルアミノ基、アルキルスルホニルアミノ基、アリールスルホニルアミノ基、アルキルチオ基またはアリールチオ基を表し、
R15は水素原子、アルキル基、アリール基、アルコキシ基、アリールオキシ基、アシルオキシ基、アルキルアミノ基、アニリノ基、アシルアミノ基、アルキルスルホニルアミノ基、アリールスルホニルアミノ基、アルキルチオ基またはアリールチオ基を表す;
R11とR12は互いに結合して環を形成していてもよい;
R13とR14は互いに結合して環を形成していてもよい;
R14とR15は互いに結合して環を形成していてもよい;
R15とR16は互いに結合して環を形成していてもよい;
ただし、R13およびR16の少なくとも一方はヒドロキシ基である。
<11> <9>または<10>に記載の紫外線吸収剤を含む紫外線カットフィルタ。
<12> <9>または<10>に記載の紫外線吸収剤を含むレンズ。
<13> <9>または<10>に記載の紫外線吸収剤を含む保護材。
<14> 式(1a)で表される化合物;
R3aおよびR6aは、各々独立にアルコキシ基またはアシルオキシ基を表し、
R4aはアルキル基またはアルコキシ基を表し、
R5aは、水素原子、アルキル基またはアルコキシ基を表す;
R1aとR2aは互いに結合して環を形成していてもよい;
R3aとR4aは互いに結合して環を形成していてもよい;
R4aとR5aは互いに結合して環を形成していてもよい;
R5aとR6aは互いに結合して環を形成していてもよい;
ただし、R3aおよびR6aがアシルオキシ基の場合、R4aおよびR5aの少なくとも一方はアルコキシ基である。
<15> 式(2a)で表される化合物と、ハロゲン化アルキル化合物またはカルボン酸ハロゲン化物とを反応させる工程を含む、式(1a)で表される化合物の合成方法;
R3aおよびR6aは、各々独立にアルコキシ基またはアシルオキシ基を表し、
R4aはアルキル基またはアルコキシ基を表し、
R5aは、水素原子、アルキル基またはアルコキシ基を表す;
R1aとR2aは互いに結合して環を形成していてもよい;
R3aとR4aは互いに結合して環を形成していてもよい;
R4aとR5aは互いに結合して環を形成していてもよい;
R5aとR6aは互いに結合して環を形成していてもよい;
ただし、R3aおよびR6aがアシルオキシ基の場合、R4aおよびR5aの少なくとも一方はアルコキシ基である;
R14aはアルキル基またはアルコキシ基を表し、
R15aは水素原子、アルキル基またはアルコキシ基を表す;
R14aとR15aは互いに結合して環を形成していてもよい。
本明細書における基(原子団)の表記において、置換および無置換を記していない表記は、置換基を有さない基と共に置換基を有する基を包含する。例えば、「アルキル基」とは、置換基を有さないアルキル基(無置換アルキル基)のみならず、置換基を有するアルキル基(置換アルキル基)をも包含する。
本明細書において「~」を用いて表される数値範囲は、「~」の前後に記載される数値を下限値および上限値として含む範囲を意味する。
本明細書において、全固形分とは、樹脂組成物の全成分から溶剤を除いた成分の合計量をいう。
本明細書において、「(メタ)アクリレート」は、アクリレートおよびメタクリレートの双方、または、いずれかを表し、「(メタ)アクリル」は、アクリルおよびメタクリルの双方、または、いずれかを表し、「(メタ)アリル」は、アリルおよびメタリルの双方、または、いずれかを表し、「(メタ)アクリロイル」は、アクリロイルおよびメタクリロイルの双方、または、いずれかを表す。
本明細書において「工程」との語は、独立した工程を意味するだけではなく、他の工程と明確に区別できない場合であってもその工程の所期の作用が達成されれば、本用語に含まれる。
本明細書において、重量平均分子量(Mw)および数平均分子量(Mn)は、ゲルパーミエーションクロマトグラフィ(GPC)により測定したポリスチレン換算値として定義される。
本発明の樹脂組成物は、式(1)で表される化合物と、樹脂とを含むことを特徴とする。
式(1)で表される化合物は、波長400nm近傍の紫外線の吸収能に優れ、かつ、着色の少ない化合物である。このため、本発明の樹脂組成物は、波長400nm近傍の紫外線の吸収能に優れた硬化物などを製造できる。
また、式(1)で表される化合物は、樹脂などとの相溶性も良好であり、硬化物表面の面状ムラなども抑制できる。このような効果が得られる詳細な理由は不明であるが、式(1)で表される化合物は、R3とR4との間で立体反発などの影響によりねじれが生じやすいと推測される。このようなねじれが生じることにより、化合物の結晶性が低下して、樹脂などとの相溶性が向上したものと推測される。
以下、本発明の樹脂組成物について詳細に説明する。
本発明の樹脂組成物は、式(1)で表される化合物(以下、化合物(1)ともいう)を含む。
R3およびR6は、各々独立にアルコキシ基、アシルオキシ基、カルバモイルオキシ基またはアルコキシカルボニルオキシ基を表し、
R4は、アルキル基、アリール基、アルコキシ基、アリールオキシ基、アシルオキシ基、アルキルアミノ基、アニリノ基、アシルアミノ基、アルキルスルホニルアミノ基、アリールスルホニルアミノ基、アルキルチオ基またはアリールチオ基を表し、
R5は、水素原子、アルキル基、アリール基、アルコキシ基、アリールオキシ基、アシルオキシ基、アルキルアミノ基、アニリノ基、アシルアミノ基、アルキルスルホニルアミノ基、アリールスルホニルアミノ基、アルキルチオ基またはアリールチオ基を表す;
R1とR2は互いに結合して環を形成していてもよい;
R3とR4は互いに結合して環を形成していてもよい;
R4とR5は互いに結合して環を形成していてもよい;
R5とR6は互いに結合して環を形成していてもよい;
ただし、R3およびR6がそれぞれ独立にアシルオキシ基またはカルバモイルオキシ基の場合、R4およびR5の少なくとも一方は、アリール基、アルコキシ基、アリールオキシ基、アシルオキシ基、アルキルアミノ基、アニリノ基、アシルアミノ基、アルキルスルホニルアミノ基、アリールスルホニルアミノ基、アルキルチオ基またはアリールチオ基である。
R3およびR6が表すアシルオキシ基の炭素数は、2~30が好ましく、2~20がより好ましく、2~15が更に好ましく、2~10が特に好ましい。アシルオキシ基は置換基を有していてもよい。置換基としては後述する置換基Tで説明した基が挙げられる。
R3およびR6が表すカルバモイルオキシ基の炭素数は、2~30が好ましく、2~20がより好ましく、2~15が更に好ましく、2~10が特に好ましく、2~8が最も好ましい。カルバモイルオキシ基は直鎖および分岐のいずれでもよい。カルバモイルオキシ基は置換基を有していてもよい。置換基としては後述する置換基Tで説明した基が挙げられる。
R3およびR6が表すアルコキシカルボニルオキシ基の炭素数は、2~30が好ましく、2~20がより好ましく、2~15が更に好ましく、2~10が特に好ましく、2~8が最も好ましい。アルコキシカルボニルオキシ基は直鎖および分岐のいずれでもよい。アルコキシカルボニルオキシ基は置換基を有していてもよい。置換基としては後述する置換基Tで説明した基が挙げられる。
R3aおよびR6aは、各々独立にアルコキシ基またはアシルオキシ基を表し、
R4aはアルキル基またはアルコキシ基を表し、
R5aは、水素原子、アルキル基またはアルコキシ基を表す;
R1aとR2aは互いに結合して環を形成していてもよい;
R3aとR4aは互いに結合して環を形成していてもよい;
R4aとR5aは互いに結合して環を形成していてもよい;
R5aとR6aは互いに結合して環を形成していてもよい;
ただし、R3aおよびR6aがアシルオキシ基の場合、R4aおよびR5aの少なくとも一方はアルコキシ基である。
R3aおよびR6aが表すアシルオキシ基の炭素数は、2~30が好ましく、2~20がより好ましく、2~15が更に好ましく、2~10が特に好ましい。アシルオキシ基は置換基を有していてもよい。置換基としては後述する置換基Tで説明した基が挙げられる。
置換基Tとしては、以下の基が挙げられる。
ハロゲン原子(例えば、塩素原子、臭素原子、ヨウ素原子);
アルキル基[直鎖、分岐、環状のアルキル基。具体的には、直鎖または分岐のアルキル基(好ましくは炭素数1~30の直鎖または分岐のアルキル基、例えばメチル基、エチル基、n-プロピル基、イソプロピル基、t-ブチル基、n-オクチル基、エイコシル基、2-クロロエチル基、2-シアノエチル基、2-エチルヘキシル基)、シクロアルキル基(好ましくは、炭素数3~30のシクロアルキル基、例えば、シクロヘキシル基、シクロペンチル基、4-n-ドデシルシクロヘキシル基)、ビシクロアルキル基(好ましくは、炭素数5~30のビシクロアルキル基、つまり、炭素数5~30のビシクロアルカンから水素原子を一個取り去った一価の基。例えば、ビシクロ[1,2,2]ヘプタン-2-イル基、ビシクロ[2,2,2]オクタン-3-イル基)、更に環構造が多いトリシクロ構造なども包含するものである。以下に説明する置換基の中のアルキル基(例えばアルキルチオ基のアルキル基)もこのような概念のアルキル基を表す。];
アルケニル基[直鎖、分岐、環状のアルケニル基。具体的には、直鎖または分岐のアルケニル基(好ましくは炭素数2~30の直鎖または分岐のアルケニル基、例えば、ビニル基、アリル基、プレニル基、ゲラニル基、オレイル基)、シクロアルケニル基(好ましくは、炭素数3~30のシクロアルケニル基。つまり、炭素数3~30のシクロアルケンの水素原子を一個取り去った一価の基である。例えば、2-シクロペンテン-1-イル基、2-シクロヘキセン-1-イル基)、ビシクロアルケニル基(好ましくは、炭素数5~30のビシクロアルケニル基、つまり二重結合を一個持つビシクロアルケンの水素原子を一個取り去った一価の基である。例えば、ビシクロ[2,2,1]ヘプト-2-エン-1-イル基、ビシクロ[2,2,2]オクト-2-エン-4-イル基)を包含するものである。];
アルキニル基(好ましくは、炭素数2~30の直鎖または分岐のアルキニル基。例えば、エチニル基、プロパルギル基);
複素環基(好ましくは5または6員の芳香族もしくは非芳香族のヘテロ環化合物から一個の水素原子を取り除いた一価の基であり、更に好ましくは、炭素数3~30の5もしくは6員の芳香族の複素環基である。例えば、2-フリル基、2-チエニル基、2-ピリミジニル基、2-ベンゾチアゾリル基);
シアノ基;
ヒドロキシ基;
ニトロ基;
カルボキシル基;
アルコキシ基(好ましくは、炭素数1~30の直鎖または分岐のアルコキシ基。例えば、メトキシ基、エトキシ基、イソプロポキシ基、t-ブトキシ基、n-オクチルオキシ基、2-メトキシエトキシ基);
アリールオキシ基(好ましくは、炭素数6~30のアリールオキシ基。例えば、フェノキシ基、2-メチルフェノキシ基、4-t-ブチルフェノキシ基、3-ニトロフェノキシ基、2-テトラデカノイルアミノフェノキシ基);
ヘテロ環オキシ基(好ましくは、炭素数2~30のヘテロ環オキシ基。例えば、1-フェニルテトラゾール-5-オキシ基、2-テトラヒドロピラニルオキシ基);
アシルオキシ基(好ましくはホルミルオキシ基、炭素数2~30のアルキルカルボニルオキシ基、炭素数6~30のアリールカルボニルオキシ基。例えば、ホルミルオキシ基、アセチルオキシ基、ピバロイルオキシ基、ステアロイルオキシ基、ベンゾイルオキシ基、p-メトキシフェニルカルボニルオキシ基);
アルコキシカルボニルオキシ基(好ましくは、炭素数2~30のアルコキシカルボニルオキシ基。例えばメトキシカルボニルオキシ基、エトキシカルボニルオキシ基、t-ブトキシカルボニルオキシ基、n-オクチルカルボニルオキシ基);
アリールオキシカルボニルオキシ基(好ましくは、炭素数7~30のアリールオキシカルボニルオキシ基。例えば、フェノキシカルボニルオキシ基、p-メトキシフェノキシカルボニルオキシ基、p-n-ヘキサデシルオキシフェノキシカルボニルオキシ基);
アミノ基(好ましくは、アミノ基、炭素数1~30のアルキルアミノ基、炭素数6~30のアニリノ基。例えば、アミノ基、メチルアミノ基、ジメチルアミノ基、アニリノ基、N-メチル-アニリノ基、ジフェニルアミノ基);
アシルアミノ基(好ましくは、ホルミルアミノ基、炭素数2~30のアルキルカルボニルアミノ基、炭素数6~30のアリールカルボニルアミノ基。例えば、ホルミルアミノ基、アセチルアミノ基、ピバロイルアミノ基、ラウロイルアミノ基、ベンゾイルアミノ基、3,4,5-トリ-n-オクチルオキシフェニルカルボニルアミノ基);
アルコキシカルボニルアミノ基(好ましくは炭素数2~30のアルコキシカルボニルアミノ基。例えば、メトキシカルボニルアミノ基、エトキシカルボニルアミノ基、t-ブトキシカルボニルアミノ基、n-オクタデシルオキシカルボニルアミノ基、N-メチルーメトキシカルボニルアミノ基);
アリールオキシカルボニルアミノ基(好ましくは、炭素数7~30のアリールオキシカルボニルアミノ基。例えば、フェノキシカルボニルアミノ基、p-クロロフェノキシカルボニルアミノ基、m-n-オクチルオキシフェノキシカルボニルアミノ基);
スルファモイルアミノ基(好ましくは、炭素数0~30のスルファモイルアミノ基。例えば、スルファモイルアミノ基、N,N-ジメチルアミノスルホニルアミノ基、N-n-オクチルアミノスルホニルアミノ基);
アルキル又はアリールスルホニルアミノ基(好ましくは炭素数1~30のアルキルスルホニルアミノ基、炭素数6~30のアリールスルホニルアミノ基。例えば、メチルスルホニルアミノ基、ブチルスルホニルアミノ基、フェニルスルホニルアミノ基、2,3,5-トリクロロフェニルスルホニルアミノ基、p-メチルフェニルスルホニルアミノ基);
メルカプト基;
アルキルチオ基(好ましくは、炭素数1~30のアルキルチオ基。例えばメチルチオ基、エチルチオ基、n-ヘキサデシルチオ基);
アリールチオ基(好ましくは炭素数6~30のアリールチオ基。例えば、フェニルチオ基、p-クロロフェニルチオ基、m-メトキシフェニルチオ基);
ヘテロ環チオ基(好ましくは炭素数2~30のヘテロ環チオ基。例えば、2-ベンゾチアゾリルチオ基、1-フェニルテトラゾール-5-イルチオ基);
スルホ基;
アルキル又はアリールスルフィニル基(好ましくは、炭素数1~30のアルキルスルフィニル基、6~30のアリールスルフィニル基。例えば、メチルスルフィニル基、エチルスルフィニル基、フェニルスルフィニル基、p-メチルフェニルスルフィニル基);
アルキル又はアリールスルホニル基(好ましくは、炭素数1~30のアルキルスルホニル基、6~30のアリールスルホニル基。例えば、メチルスルホニル基、エチルスルホニル基、フェニルスルホニル基、p-メチルフェニルスルホニル基);
アリールオキシカルボニル基(好ましくは、炭素数7~30のアリールオキシカルボニル基。例えば、フェノキシカルボニル基、o-クロロフェノキシカルボニル基、m-ニトロフェノキシカルボニル基、p-t-ブチルフェノキシカルボニル基);
アルコキシカルボニル基(好ましくは、炭素数2~30のアルコキシカルボニル基。例えば、メトキシカルボニル基、エトキシカルボニル基、t-ブトキシカルボニル基、n-オクタデシルオキシカルボニル基);
カルバモイル基(好ましくは、炭素数1~30のカルバモイル基。例えば、カルバモイル基、N-メチルカルバモイル基、N,N-ジメチルカルバモイル基、N,N-ジ-n-オクチルカルバモイル基、N-(メチルスルホニル)カルバモイル基);
アリール又はヘテロ環アゾ基(好ましくは炭素数6~30のアリールアゾ基、炭素数3~30のヘテロ環アゾ基。例えば、フェニルアゾ基、p-クロロフェニルアゾ基、5-エチルチオ-1,3,4-チアジアゾール-2-イルアゾ基);
イミド基(好ましくは、N-スクシンイミド基、N-フタルイミド基);
ホスフィノ基(好ましくは、炭素数2~30のホスフィノ基。例えば、ジメチルホスフィノ基、ジフェニルホスフィノ基、メチルフェノキシホスフィノ基)
ホスフィニル基(好ましくは、炭素数2~30のホスフィニル基。例えば、ホスフィニル基、ジオクチルオキシホスフィニル基、ジエトキシホスフィニル基);
ホスフィニルオキシ基(好ましくは、炭素数2~30のホスフィニルオキシ基。例えば、ジフェノキシホスフィニルオキシ基、ジオクチルオキシホスフィニルオキシ基);
ホスフィニルアミノ基(好ましくは、炭素数2~30のホスフィニルアミノ基。例えば、ジメトキシホスフィニルアミノ基、ジメチルアミノホスフィニルアミノ基);
ε405=εmax×(A405/Amax)
ε405は化合物(1)の波長405nmにおけるモル吸光係数であり、εmaxは化合物(1)の極大吸収波長におけるモル吸光係数であり、A405は化合物(1)の波長405nmにおける吸光度であり、Amaxは化合物(1)の極大吸収波長における吸光度である。
化合物(1)の含有量は、樹脂の100質量部に対して、0.01~50質量部であることが好ましい。下限は、0.05質量部以上であることが好ましく、0.1質量部以上であることがより好ましい。上限は、40質量部以下であることが好ましく、30質量部以下であることがより好ましく、20質量部以下であることがより好ましい。
樹脂組成物は、化合物(1)を1種のみ含んでいてもよく、2種以上含んでいてもよい。化合物(1)を2種以上含む場合は、それらの合計量が上記範囲であることが好ましい。
本発明の樹脂組成物は、更に式(2)で表される化合物(以下、化合物(2)ともいう)を含むことが好ましい。この態様によれば、樹脂組成物の保存安定性をより向上させることができる。
R13およびR16は、各々独立にヒドロキシ基、アルコキシ基、アリールオキシ基、アシルオキシ基、カルバモイルオキシ基、アルコキシカルボニルオキシ基、アリールオキシカルボニルオキシ基、スルフィニルオキシ基またはスルホニルオキシ基を表し、
R14はハロゲン原子、アルキル基、アリール基、アルコキシ基、アリールオキシ基、アシルオキシ基、アルキルアミノ基、アニリノ基、アシルアミノ基、アルキルスルホニルアミノ基、アリールスルホニルアミノ基、アルキルチオ基またはアリールチオ基を表し、
R15は水素原子、ハロゲン原子、アルキル基、アリール基、アルコキシ基、アリールオキシ基、アシルオキシ基、アルキルアミノ基、アニリノ基、アシルアミノ基、アルキルスルホニルアミノ基、アリールスルホニルアミノ基、アルキルチオ基またはアリールチオ基を表す;
R11とR12は互いに結合して環を形成していてもよい;
R13とR14は互いに結合して環を形成していてもよい;
R14とR15は互いに結合して環を形成していてもよい;
R15とR16は互いに結合して環を形成していてもよい;
ただし、R13およびR16の少なくとも一方はヒドロキシ基である。
また、樹脂組成物の全固形分中における化合物(1)と化合物(2)との合計の含有量は、0.01~50質量%であることが好ましい。下限は、0.05質量%以上であることが好ましく、0.1質量%以上であることがより好ましい。上限は、40質量%以下であることが好ましく、30質量%以下であることがより好ましく、20質量%以下であることがより好ましい。
化合物(1)と化合物(2)との合計の含有量は、樹脂の100質量部に対して、0.01~50質量部であることが好ましい。下限は、0.05質量部以上であることが好ましく、0.1質量部以上であることがより好ましい。上限は、40質量部以下であることが好ましく、30質量部以下であることがより好ましく、20質量部以下であることがより好ましい。
樹脂組成物は、化合物(2)を1種のみ含んでいてもよく、2種以上含んでいてもよい。化合物(2)を2種以上含む場合は、それらの合計量が上記範囲であることが好ましい。
本発明の樹脂組成物は、上述した化合物(1)以外の他の紫外線吸収剤(以下、他の紫外線吸収剤ともいう)を含むことができる。この態様によれば、紫外領域の波長の光を広範囲にわたって遮光できる硬化物を形成することができる。
また、樹脂組成物の全固形分中における化合物(1)と化合物(2)と他の紫外線吸収剤の合計の含有量は、0.01~50質量%であることが好ましい。下限は、0.05質量%以上であることが好ましく、0.1質量%以上であることがより好ましい。上限は、40質量%以下であることが好ましく、30質量%以下であることがより好ましく、20質量%以下であることがより好ましい。
樹脂組成物は、他の紫外線吸収剤を1種のみ含んでいてもよく、2種以上含んでいてもよい。他の紫外線吸収剤を2種以上含む場合は、それらの合計量が上記範囲であることが好ましい。
本発明の樹脂組成物は樹脂を含む。樹脂の種類としては、(メタ)アクリル樹脂、ポリエステル樹脂、ポリカーボネート樹脂、ビニル重合体[例えば、ポリジエン樹脂、ポリアルケン樹脂、ポリスチレン樹脂、ポリビニルエーテル樹脂、ポリビニルアルコール樹脂、ポリビニルケトン樹脂、ポリフルオロビニル樹脂およびポリ臭化ビニル樹脂など]、ポリチオエーテル樹脂、ポリフェニレン樹脂、ポリウレタン樹脂、ポリチオウレタン樹脂、ポリスルホネート樹脂、ニトロソポリマー樹脂、ポリシロキサン樹脂、ポリサルファイド樹脂、ポリチオエステル樹脂、ポリスルホン樹脂、ポリスルホンアミド樹脂、ポリアミド樹脂、ポリイミン樹脂、ポリウレア樹脂、ポリホスファゼン樹脂、ポリシラン樹脂、ポリシラザン樹脂、ポリフラン樹脂、ポリベンゾオキサゾール樹脂、ポリオキサジアゾール樹脂、ポリベンゾチアジノフェノチアジン樹脂、ポリベンゾチアゾール樹脂、ポリピラジノキノキサリン樹脂、ポリピロメリットイミド樹脂、ポリキノキサリン樹脂、ポリベンゾイミダゾール樹脂、ポリオキソイソインドリン樹脂、ポリジオキソイソインドリン樹脂、ポリトリアジン樹脂、ポリピリダジン樹脂、ポリピペラジン樹脂、ポリピリジン樹脂、ポリピペリジン樹脂、ポリトリアゾール樹脂、ポリピラゾール樹脂、ポリピロリジン樹脂、ポリカルボラン樹脂、ポリオキサビシクロノナン樹脂、ポリジベンゾフラン樹脂、ポリフタライド樹脂、ポリアセタール樹脂、ポリイミド樹脂、オレフィン樹脂、環状オレフィン樹脂、エポキシ樹脂、セルロースアシレート樹脂などが挙げられる。用途や目的に応じて適宜選択することができる。これらの詳細については、特開2009-263616号公報の段落番号0075~0097の記載を参酌することができ、この内容は本明細書に組み込まれる。
スチレン系樹脂は、公知のアニオン、塊状、懸濁、乳化または溶液重合方法により得ることができる。また、ポリスチレン系樹脂においては、共役ジエンやスチレン系単量体のベンゼン環の不飽和二重結合が水素添加されていてもよい。水素添加率は核磁気共鳴装置(NMR)によって測定できる。
樹脂組成物は、硬化性化合物を含有することができる。硬化性化合物としては、重合性化合物、-O-Si-O-構造を有する化合物などが挙げられる。
架橋剤としては、架橋性基として2以上のイソシアネート基を有するポリイソシアネートが挙げられ、上市されている市販品の例として、新中村化学工業(株)のAD-TMP、A-9550(いずれも商品名)等が挙げられる。なかでも、活性水素を含む基を2以上(好ましくは3以上)有する(メタ)アクリル樹脂と、2以上のイソシアネート基を有する架橋剤(2以上のイソシアネート基を有するポリイソシアネートが好ましく、より好ましく3以上のイソシアネート基を有するポリイソシアネート)と、を併用することが好ましい。これにより、活性水素を含む基とイソシアネート基とを反応させることで、架橋構造を形成することができる。
樹脂組成物は、重合開始剤を含有することができる。特に硬化性化合物として、重合性化合物を用いた場合、重合開始剤を含有させることが好ましい。樹脂組成物が重合開始剤を含むことで、重合性化合物の重合反応を良好に開始することができる。重合開始剤は、エネルギーの付与により重合反応に必要な開始種を発生し得る化合物を用いることができる。重合開始剤としては、例えば、光重合開始剤及び熱重合開始剤の中から適宜選択することができ、光重合開始剤が好ましい。
本発明の樹脂組成物は、酸発生剤を含有することができる。特に、重合性化合物として、エポキシ基を有する化合物など、カチオン重合性化合物を用いた場合には、酸発生剤を含有することが好ましい。酸発生剤は、光酸発生剤であってもよく、熱酸発生剤であってもよい。なお、本明細書において、酸発生剤とは、熱や光などのエネルギーを加えることで酸を発生する化合物を意味する。また、熱酸発生剤とは、熱分解により酸を発生する化合物を意味する。また、光酸発生剤とは、光照射により酸を発生する化合物を意味する。酸発生剤の種類、具体的化合物、および好ましい例としては、特開2008-013646号公報の段落番号0066~0122に記載の化合物などを挙げることができ、これらを本発明にも適用することができる。
樹脂組成物は、触媒を含有することができる。特に硬化性化合物として、-O-Si-O-構造を有する化合物を用いた場合、触媒を含有させることが好ましい。この態様によれば、ゾルゲル反応が促進されて、より強固な膜が得られやすい。触媒としては、塩酸、硫酸、酢酸、プロピオン酸等の酸触媒、水酸化ナトリウム、水酸化カリウム、トリエチルアミン等の塩基触媒などが挙げられる。樹脂組成物が触媒を含有する場合、触媒の含有量は、硬化性化合物の100質量部に対し0.1~100質量部が好ましく、より好ましくは0.1~50質量部であり、更に好ましくは0.1~20質量部である。樹脂組成物は、触媒を1種類のみ含んでいてもよいし、2種類以上含んでいてもよい。触媒を2種類以上含む場合は、それらの合計量が上記範囲となることが好ましい。
本発明の樹脂組成物は、シランカップリング剤を含有することができる。この態様によれば、得られる膜の支持体との密着性をより向上させることができる。本発明において、シランカップリング剤は、加水分解性基とそれ以外の官能基とを有するシラン化合物を意味する。また、加水分解性基とは、ケイ素原子に直結し、加水分解反応及び縮合反応の少なくともいずれかによってシロキサン結合を生じ得る置換基をいう。加水分解性基としては、例えば、ハロゲン原子、アルコキシ基、アシルオキシ基などが挙げられ、アルコキシ基が好ましい。すなわち、シランカップリング剤は、アルコキシシリル基を有する化合物が好ましい。また、加水分解性基以外の官能基としては、例えば、ビニル基、(メタ)アリル基、(メタ)アクリロイル基、メルカプト基、エポキシ基、オキセタニル基、アミノ基、ウレイド基、スルフィド基、イソシアネート基、フェニル基などが挙げられ、アミノ基、(メタ)アクリロイル基およびエポキシ基が好ましい。シランカップリング剤の具体例としては、特開2009-288703号公報の段落番号0018~0036に記載の化合物、特開2009-242604号公報の段落番号0056~0066に記載の化合物が挙げられ、これらの内容は本明細書に組み込まれる。シランカップリング剤の市販品としては、綜研化学(株)のA-50(オルガノシラン)などが挙げられる。樹脂組成物の全固形分中におけるシランカップリング剤の含有量は、0.1~5質量%が好ましい。上限は、3質量%以下が好ましく、2質量%以下がより好ましい。下限は、0.5質量%以上が好ましく、1質量%以上がより好ましい。シランカップリング剤は、1種のみでもよく、2種以上でもよい。2種以上の場合は、合計量が上記範囲となることが好ましい。
本発明の樹脂組成物は、界面活性剤を含有することができる。界面活性剤としては、フッ素系界面活性剤、ノニオン系界面活性剤、カチオン系界面活性剤、アニオン系界面活性剤、シリコン系界面活性剤などの各種界面活性剤を使用することができる。界面活性剤はフッ素系界面活性剤であることが好ましい。樹脂組成物にフッ素系界面活性剤を含有させることで液特性(特に、流動性)がより向上し、厚みムラの小さい膜を形成することもできる。フッ素系界面活性剤中のフッ素含有率は、3~40質量%が好適であり、より好ましくは5~30質量%であり、特に好ましくは7~25質量%である。フッ素含有率がこの範囲内であるフッ素系界面活性剤は、塗布膜の厚さの均一性や省液性の点で効果的であり、樹脂組成物中における溶解性も良好である。
樹脂組成物は、更に溶剤を含むことが好ましい。溶剤としては、特に限定は無く、水及び有機溶剤が挙げられる。有機溶剤としては、アルコール系溶剤、エステル系溶剤、ケトン系溶剤、アミド系溶剤、エーテル系溶剤、炭化水素系溶剤、ハロゲン系溶剤などが挙げられる。有機溶剤の具体例としては、メタノール、エタノール、1-プロパノール、2-プロパノール、1-ブタノール、2-ブタノール、2-メチル-1-プロパノール、1-メトキシ-2-プロパノール、2-エトキシエタノール、2-ブトキシエタノール、ポリエチレングリコールモノアルキルエーテル、ポリプロピレングリコールモノアルキルエーテル、エチレングリコール、プロピレングリコール、ポリエチレングリコール、ポリプロピレングリコール、グリセリン、エチレンカーボネート、N-メチルピロリドン、ジオキサン、テトラヒドロフラン、エチレングリコールジアルキルエーテル、プロピレングリコールジアルキルエーテル、ポリエチレングリコールジアルキルエーテル、ポリプロピレングリコールジアルキルエーテル、アセトニトリル、プロピオニトリル、ベンゾニトリル、カルボン酸エステル、リン酸エステル、ホスホン酸エステル、ジメチルスルホキシド、スルホラン、ジメチルホルムアミド、ジメチルアセトアミド、酢酸エチル、クロロホルム、メチレンクロライド、酢酸メチル等が挙げられる。溶剤は、1種のみであってもよく、2種類以上を併用してもよい。溶剤の含有量は、樹脂組成物の全量に対し、10~90質量%であることが好ましい。
樹脂組成物は、必要に応じて、酸化防止剤、光安定剤、加工安定剤、老化防止剤、相溶化剤などの任意の添加剤を適宜含有してもよい。これらの成分を適宜含有させることにより、得られる硬化物の各種特性を適宜調整できる。
本発明の樹脂組成物は、日光または紫外線を含む光に晒される可能性のある用途に好適に使用することもできる。具体例としては、住居、施設、輸送機器などの窓ガラス用のコーティング材またはフィルム;住居、施設、輸送機器などの内外装材および内外装用塗料;蛍光灯、水銀灯などの紫外線を発する光源用部材;太陽電池、精密機械、電子電気機器、表示装置用部材;食品、化学品、薬品などの容器または包装材;農工業用シート;スポーツウェア、ストッキング、帽子などの衣料用繊維製品および繊維;プラスチックレンズ、コンタクトレンズ、メガネ、義眼などのレンズまたはそのコーティング材;光学フィルタ、プリズム、鏡、写真材料などの光学用品;テープ、インクなどの文房具;標示板、標示器などとその表面コーティング材などが挙げられる。これらの詳細については、特開2009-263617号公報の段落番号0158~0218の記載を参酌でき、この内容は本明細書に組み込まれる。
本発明の硬化物は、上述した本発明の樹脂組成物を用いて得られるものである。本明細書における「硬化物」には、樹脂組成物を乾燥させて固化された乾燥物、及び樹脂組成物が硬化反応する場合は、樹脂組成物を硬化反応させて硬化した硬化物が含まれる。
本発明の紫外線吸収剤は、上述した式(1)で表される化合物(化合物(1))を含む。化合物(1)については、上述した樹脂組成物の項で説明した内容と同様であり、好ましい範囲も同様である。紫外線吸収剤に用いられる化合物(1)は、上述した式(1a)で表される化合物であることが好ましい。
本発明の光学部材は、上述した本発明の紫外線吸収剤を含む。本発明の光学部材は上述した本発明の樹脂組成物を用いて得られる硬化物を含むものであることも好ましい。本発明の硬化物は、上述した本発明の樹脂組成物を所望の形状に成形した成形物として得られるものでもよい。成形体の形状については、用途や目的に応じて適宜選択することができる。例えば、コーティング膜状、フィルム状、シート状、板状、レンズ状、管状、繊維状などが挙げられる。
本発明の光学部材は、液晶表示装置(LCD)、有機エレクトロルミネッセンス表示装置(OLED)等のディスプレイの構成部材として好ましく用いることができる。
<<液晶表示装置>>
液晶表示装置としては、反射防止フィルム、偏光板保護フィルム、光学フィルム、位相差膜、粘着剤、接着剤等の部材に本発明の紫外線吸収剤を含有する液晶表示装置が挙げられる。本発明の紫外線吸収剤を含む光学部材は、液晶セルに対して視認者側(フロント側)、バックライト側のどちらに配置してもよく、また、偏光子に対して液晶セルから遠い側(アウター)、同じく近い側(インナー)のどちらにも配置できる。図1~10に本発明の紫外線吸収剤を含む光学部材を含む液晶表示装置の好ましい構成を示す。なお、図1~10は模式図であり、各層の厚みの関係や位置関係などは必ずしも実際のものとは一致しない。図1は、フロント側の偏光板保護フィルムに本発明の紫外線吸収剤を添加した構成を示す概略図であり、図2は、バックライト側の偏光板保護フィルムに本発明の紫外線吸収剤を添加した構成を示す概略図である。図3は、フロント側のインナー保護膜に本発明の紫外線吸収剤を添加した構成を示す概略図であり、図4は、バックライト側のインナー保護膜に本発明の紫外線吸収剤を添加した構成を示す概略図である。なお、上記インナー保護膜は位相差膜を兼ねることもできる。図5は、フロント側の位相差膜に接着剤または粘着剤を介して本発明の紫外線吸収剤を含む光学フィルムを貼合した構成を示す概略図であり、図6は、バックライト側の位相差膜に接着剤または粘着剤を介して本発明の紫外線吸収剤を含む光学フィルムを貼合した構成を示す概略図である。図7は、フロント側の接着剤または粘着剤中に本発明の紫外線吸収剤を添加した構成を示す概略図であり、図8は、バックライト側の接着剤または粘着剤中に本発明の紫外線吸収剤を添加した構成を示す概略図である。図9は、フロント側の機能層中に本発明の紫外線吸収剤を添加した構成を示す概略図であり、図10は、バックライト側の機能層中に本発明の紫外線吸収剤を添加した構成を示す概略図である。機能層としては、反射防止層、ハードコート層等が挙げられる。
有機エレクトロルミネッセンス表示装置としては、光学フィルム、円偏光板中の偏光板保護膜、1/4波長板等の位相差膜、接着剤、粘着剤等の部材に本発明の紫外線吸収剤を含有する有機エレクトロルミネッセンス表示装置が挙げられる。また、上記剥離性積層フィルムを接着剤または粘着剤を介して円偏光板に貼合した形態も本発明の紫外線吸収剤の導入方法として好ましい。上記構成で本発明の紫外線吸収剤を添加することにより、有機エレクトロルミネッセンス表示装置の外光による劣化を抑制することができる。
本発明の化合物は、上述した式(1a)で表される化合物である。式(1a)で表される化合物については、上述した樹脂組成物の項で説明した内容と同様であり、好ましい範囲も同様である。式(1a)で表される化合物は、紫外線吸収剤として好ましく用いられる。
ε405=εmax×(A405/Amax)
ε405は式(1a)で表される化合物の波長405nmにおけるモル吸光係数であり、εmaxは式(1a)で表される化合物の極大吸収波長におけるモル吸光係数であり、A405は式(1a)で表される化合物の波長405nmにおける吸光度であり、Amaxは式(1a)で表される化合物の極大吸収波長における吸光度である。
R14aはアルキル基またはアルコキシ基を表し、
R15aは水素原子、アルキル基またはアルコキシ基を表す;
R14aとR15aは互いに結合して環を形成していてもよい。
(合成例1)(化合物(1)-1)の合成)
以下のスキームに従い中間体1-1を合成した。下記スキーム中、p-トルキノンから中間体1-1までの合成は、特開2016-081035号公報の段落番号0176に記載の方法を参照し、2-tert-ブチル-1,4-ベンゾキノンの代わりにp-トルキノンを使用して行った。
合成例1において、2-ヨードプロパンの代わりに対応するアルキル化剤を使用した以外は合成例1と同様の方法で化合物(1)-2~化合物(1)-8をそれぞれ合成した。
合成例1において、中間体1-2の代わりに、1,2-ジメチル-ピラゾリジン-3,5-ジオンを使用する以外は合成例1と同様の方法で化合物(1)-9および化合物(1)-10をそれぞれ合成した。
合成例1と同様の方法により、下記のスキームに従い、化合物(2)-40を合成した。
合成例1と同様の方法により、以下のスキームに従い、中間体15-2を合成した。下記スキーム中、中間体1-1から中間体15-2までの合成は、合成例1で使用した中間体1-2の代わりに中間体15-1を使用する事で行った。なお、中間体15-1は、Journal of the American Chemical Society,2009,vol.131,33,p.11875-11881に記載された方法で合成した。
下記のスキームに従い、中間体16-2を合成した。下記スキーム中、1,4-ナフトキノンから中間体16-2までの合成は、合成例1で使用したp-トルキノンの代わりに1,4-ナフトキノンを使用し、中間体1-2の代わりに中間体16-1を使用する事で行った。
下記のスキームに従い、化合物(2)-22を合成した。下記スキーム中、中間体1-1から化合物(2)-22までの合成は、合成例1で使用した中間体1-2の代わりに中間体37-1を使用する事で行った。
下記のスキームに従い、化合物(2)-1を合成した。下記スキーム中、2,3ジメチル-p-ベンゾキノンから化合物(2)-1までの合成は、合成例1で使用したp-トルキノンの代わりに2,3ジメチル-p-ベンゾキノンを使用する事で行った。
下記のスキームに従い、化合物(2)-54を合成した。下記スキーム中、2,3ジメチル-p-ベンゾキノンから化合物(2)-54までの合成は、合成例1で使用したp-トルキノンの代わりに2,3ジメチル-p-ベンゾキノンを使用する事で行った。
下記表に記載の化合物(化合物(1)-1~化合物(1)-16、化合物(1)-37、化合物(1)-46、化合物(1)-47、化合物(1)-48、比較化合物1~4)の2mgを酢酸エチル100mLに溶解した後、溶液の吸光度が0.6~1.2の範囲になるように酢酸エチルで希釈して試料溶液101~120を調製した。なお、比較化合物1~4として以下の構造の化合物を用いた。
ε405=εmax×(A405/Amax)
ε405は試料溶液の波長405nmにおけるモル吸光係数であり、εmaxは試料溶液の極大吸収波長におけるモル吸光係数であり、A405は試料溶液の波長405nmにおける吸光度であり、Amaxは試料溶液の極大吸収波長における吸光度である。
ε405の値が、3000以上であるものをA、3000未満500以上であるものをB、500未満であるものをCとして3段階で評価した。ε405の値が大きいほど、405nmにおける吸収能が高い事を意味する。評価結果を下記表1のε405の欄に記す。
下記表に記載の化合物と、クロロホルムの7.6gと、(メタ)アクリル樹脂(ダイヤナールBR-80、三菱ケミカル株式会社、モノマー単位としてメチルメタクリレートを60質量%以上含有、Mw95000)の1.1gとを混合して樹脂組成物を調製した。得られた樹脂組成物をガラス基板上にスピンコート塗布して塗布膜を形成し、得られた塗布膜を110℃で2分間乾燥させて、樹脂膜を作製した。なお、下記表2の化合物の種類の欄に記載の化合物(1)-1、化合物(1)-2、化合物(1)-8、化合物(1)-11、化合物(1)-12、化合物(1)-13、化合物(1)-14、化合物(1)-5、化合物(1)-37、化合物(1)-46、化合物(1)-47、化合物(1)-48、比較化合物1~4は、それぞれ上述した構造の化合物である。
上記で作製した樹脂膜について、光学顕微鏡(オリンパス社製、MX-61L)を用いて明視野200倍で観察し、樹脂膜にムラが無いか観察した。光学顕微鏡でムラが確認されず均一な膜となっている場合、成膜時の熱応力に対する耐性が優れていると判断される。面状ムラの評価結果を下記表2に示す。
A:光学顕微鏡でムラが見られない。
B:光学顕微鏡で僅かにムラがみられる。
C:光学顕微鏡でムラが強くみられる。
上記で作製した樹脂膜について、以下の条件1にて耐光性試験を行い、極大吸収波長(λmax)での吸光度の維持率を求め、耐光性を評価した。具体的には、樹脂膜の極大吸収波長(λmax)における吸光度を測定した後、樹脂膜を条件1にて1週間耐光性試験を行った、耐光性試験後の樹脂膜の極大吸収波長(λmax)における吸光度を測定した。
装置:キセノンキセノンウェザーメーター(スガ試験機社:XL75)
照度:10klx(40w/m2)
試験期間:1週間
環境:23℃、相対湿度50%
吸光度の維持率(%)=100×(照射後の樹脂膜のλmaxにおける吸光度)/(照射前の樹脂膜のλmaxにおける吸光度)
A:吸光度の維持率が90%以上
B:吸光度の維持率が80%以上90%未満
C:吸光度の維持率が80%未満
下記表に記載の化合物と、クロロホルムの7.6gと、(メタ)アクリル樹脂(ダイヤナールBR-80、三菱ケミカル株式会社、モノマー単位としてメチルメタクリレートを60質量%以上含有、Mw95000)の1.1gとを混合して樹脂組成物を調製した。得られた樹脂組成物をガラス基板上にスピンコート塗布して塗布膜を形成し、得られた塗布膜を110℃で2分間乾燥させて、樹脂膜を作製した。なお、下記表3の化合物の種類の欄に記載の化合物のうち、化合物(1)-1、化合物(1)-5、化合物(1)-8はそれぞれ上述した構造の化合物である。また、UV-1~UV-6は下記構造の化合物である。
上記で作製した樹脂膜について、試験例2-1と同様の方法及び評価基準にて面状ムラを評価した。
上記で作製した樹脂膜について、試験例2-1の条件1にて、耐光性試験を行い、波長405nmでの吸光度の維持率を求め、耐光性2を評価した。具体的には、樹脂膜の波長405nmにおける吸光度を測定した後、樹脂膜を条件1にて1週間耐光性試験を行った、耐光性試験後の樹脂膜の波長405nmにおける吸光度を測定した。耐光性試験前後の樹脂膜の405nmにおける吸光度の値から下記式より吸光度の維持率(%)を算出した。維持率は下記式に従い計算した。
吸光度の維持率(%)=100×(照射後の樹脂膜の波長405nmにおける吸光度)/(照射前の樹脂膜の波長405nmにおける吸光度)
A:吸光度の維持率が90%以上
B:吸光度の維持率が80%以上90%未満
C:吸光度の維持率が80%未満
下記に示す方法で、樹脂膜301を作製した。
(1)原料の調製
(1-1)セルロースアシレートの調製
アセチル置換度2.85のセルロースアシレートを調製した。触媒として硫酸(セルロース100質量部に対し7.8質量部)を添加し、各カルボン酸を添加し40℃でアシル化反応を行った。その後、硫酸触媒量、水分量および熟成時間を調整することで全置換度と6位置換度を調整した。熟成温度は40℃で行った。さらにこのセルロースアシレートの低分子量成分をアセトンで洗浄し除去した。
糖エステル化合物を以下の方法で調製した。
まず、下記構造の糖エステル化合物1を国際公開第2009/003164号の段落番号0054の例示化合物3の合成に記載の方法で合成した。また、糖エステル化合物2についても、同様の方法で合成した。
下記組成物をミキシングタンクに投入し、撹拌して各成分を溶解し、さらに80℃に約180分間加熱した後、平均孔径34μmのろ紙および平均孔径10μmの焼結金属フィルターでろ過した。
セルロースアシレート(置換度2.85) ・・・100.0質量部
糖エステル1 ・・・7.5質量部
糖エステル2 ・・・2.5質量部
紫外線吸収剤1(化合物(1)-5) ・・・0.1質量部
紫外線吸収剤2(比較化合物5) ・・・0.1質量部
塩化メチレン ・・・475.3質量部
メタノール ・・・103.9質量部
ブタノール ・・・4.6質量部
具体的な糖エステルの構造を以下に示す。糖エステル1の添加量は7.5質量%で平均置換度5.5の下記構造のものを使用した。置換度の算出はHPLC(高効率液体クロマトグラフィー)にて測定を行った。糖エステル2の添加量は2.5質量%であり、化合物(1)-5は0.1質量%である。
上述のドープを、ドラム製膜機を用いて流延した。-10℃に冷却された金属支持体上に接するようにコア層のドープを、コア層のドープ上に表層のドープがくるようにダイから共流延しゲル化させて剥ぎ取った。なお、ドラムはステンレス製であった。
流延されて得られたウェブ(フィルム)を、ドラムから剥離後、フィルム搬送時に30~40℃で、クリップでウェブの両端をクリップして搬送するテンター装置を用いてテンター装置内で20分間乾燥した。その後、乾燥されたものを枠張りして140℃で後乾燥した。なお、ここでいう乾燥温度とは、フィルムの膜面温度のことを意味する。
下記表に示した組成のフィルムを作製し、その製造適性を判断する目的で、ロール幅1280mm、ロール長2600mmのロールを上記条件で最低24ロール作製した。連続で製造した24ロールの中の1ロールについて100m間隔で長手1mのサンプル(幅1280mm)を切り出して各測定を行った。得られたセルロースアシレートフィルムを各実施例および比較例の樹脂膜301~309とした。
下記に示す方法で偏光板を作製した。
(6-1)樹脂膜の鹸化処理
作製した樹脂膜303A、304A、308Aを、2.3mol/Lの水酸化ナトリウム水溶液に、55℃で3分間浸漬した。室温(25℃)の水洗浴槽中で洗浄し、30℃で0.05mol/Lの硫酸を用いて中和した。再度、室温の水洗浴槽中で洗浄し、更に100℃の温風で乾燥した。
厚さ80μmのポリビニルアルコール(PVA)フィルムを、ヨウ素濃度0.05質量%のヨウ素水溶液中に30℃で60秒浸漬して染色し、次いでホウ酸濃度4質量%のホウ酸水溶液中に60秒浸漬している間に元の長さの5倍に縦延伸した後、50℃で4分間乾燥させて、厚さ19μmの偏光子を得た。
位相差膜として下記のVA位相差膜1またはVA位相差膜2を使用した。
<シクロオレフィン系ポリマーAの合成>
8-メトキシカルボニル-8-メチルテトラシクロ[4.4.0.12,5.17,10]-3-ドデセン72.5質量部、ジシクロペンタジエン27.5質量部、分子量調節剤として1-へキセン5.6質量部及びトルエン200質量部を、窒素置換した反応容器に仕込み、80℃に加熱した。これにトリエチルアルミニウム(0.6モル/L)のトルエン溶液0.18ml、メタノール変性WCl6のトルエン溶液(0.025モル/L)0.58mlを加え、80℃で3時間反応させることにより開環重合体を得た。次いで、得られた開環重合体の溶液をオートクレーブに入れ、更にトルエンを200質量部加えた。水添触媒であるRuHCl(CO)[P(C6H5)]3をモノマー仕込み量に対して2500ppm添加し、水素ガス圧を9-10MPaとし、160-165℃にて3時間の反応を行った。反応終了後、多量のメタノール溶液に沈殿させることにより開環重合体の水素添加物(シクロオレフィン系ポリマーA)を得た。得られた開環重合体の水素添加物は、重量平均分子量(Mw)=119×103、分子量分布(Mw/Mn)=3.1であった。
微粒子(アエロジル R812 日本アエロジル社製)の11質量部と、エタノールの89質量部をディゾルバーで50分間攪拌混合した後、マントンゴーリンで分散して、微粒子分散液を調製した。
メチレンクロライドの99質量部を入れた溶解タンクにシクロオレフィン系ポリマーAの4質量部を添加し、加熱して完全に溶解させた後、充分に撹拌しながら、ここに微粒子分散液の11質量部をゆっくりと添加し、アトライターにて分散を行った。これをフィルタ(日本精線社製、ファインメットNF)でろ過し、微粒子添加液を調製した。
まず、加圧溶解タンクにメチレンクロライドとメタノールを添加した。溶剤の入った加圧溶解タンクにシクロオレフィン系ポリマーAを攪拌しながら投入した。これを加熱し、攪拌しながら、完全に溶解し、主ドープ液を調製した。主ドープ液100質量部に微粒子添加液を2質量部加えて、インラインミキサー(東レ静止型管内混合機Hi-Mixer、SWJ)で十分に混合し、次いでベルト流延装置を用い、幅2mのステンレスバンド支持体に均一に流延した。得られたウェブ(フィルム)について、残留溶剤量が110質量%になるまで溶剤を蒸発させ、ステンレスバンド支持体から剥離した。剥離後に張力をかけて縦延伸倍率が2%となるように延伸した。次いで、フィルムの残留溶剤量が1質量%未満となるまで乾燥させた後、更にテンターを用いてフィルム搬送方向に直交する方向へ165℃で、35%延伸した。なお、残留溶剤量は下記の式にしたがって求めた。
残留溶剤量(質量%)={(M-N)/N}×100
ここで、Mはウェブの任意時点での質量、NはMを測定したウェブを120℃で2時間乾燥させた時の質量である。
以上により、幅1.5m、かつ端部に幅1cm、高さ8μmのナーリングを有する膜厚35μm、Rthが121nmのVA位相差膜1を作製した。
<セルロースアシレートの作成>
特開平10-045804号公報、特開平08-231761号公報に記載の方法で、セルロースアシレートを合成し、そのアシル基置換度を測定した。具体的には、触媒として硫酸(セルロース100質量部に対し7.8質量部)を添加し、アシル基の原料となるカルボン酸(酢酸)を添加し40℃でアシル化反応を行った。この時、カルボン酸の量を調整することでアシル基(アセチル基)の置換度を調整した。またアシル化後に40℃で熟成を行った。さらにこのセルロースアシレート(セルロースアセテート)の低分子量成分をアセトンで洗浄し除去し、種々の平均アシル基置換度を有するセルロースアシレートを得た。
下記の組成物をミキシングタンクに投入し、撹拌して、各成分を溶解し、コア層形成用ドープを調製した。
(コア層形成用ドープの組成)
セルロースアセテート(置換度2.4) ・・・100.0質量部
添加剤A ・・・12.0質量部
添加剤B ・・・3.5質量部
添加剤C ・・・1.0質量部
メチレンクロライド ・・392.0質量部
メタノール ・・・58.5質量部
下記の組成物をミキシングタンクに投入し、撹拌して、セルロースアセテートを溶解し、スキン層形成用ドープを調製した。
(スキン層形成用ドープの組成)
セルロースアセテート(置換度2.8) ・・・100質量部
メチレンクロライド ・・・440質量部
メタノール ・・・65.8質量部
バンド流延装置を用い、調製したコア層形成用ドープ及びスキン層形成用ドープをスキン層、コア層、スキン層の順に積層するように三層共流延した。乾燥後のコア層の膜厚が39μm、各スキン層の膜厚が1μmとなるようにした。得られたフィルム(ウェブ)をバンドから剥離し、クリップに挟み、フィルム全体の質量に対する残留溶媒量が20~5質量%の状態のときにテンターを用いて140℃で1.1倍の延伸倍率で横延伸(幅方向に延伸)した。その後にフィルムからクリップを外して140℃で20分間乾燥させた後、更にテンターを用いてフィルムのTg(ガラス転移温度)-3℃で1.2倍の延伸倍率で横延伸しVA位相差膜2を作製した。得られたVA位相差膜2の膜厚は40μmであった。なお、「延伸倍率(%)」とは、以下の式により求められるものを意味する。
延伸倍率(%)=100×{(延伸後の長さ)-(延伸前の長さ)}/延伸前の長さなお、Tgは動的粘弾性測定により求められる損失正接tanδが最大値となる温度である。損失正接tanδは動的粘弾性測定装置(アイティー計測制御株式会社製DVA-200)を用いて、あらかじめ温度25℃、相対湿度60%雰囲気下で2時間以上調湿したフィルム試料について、下記条件において、E”(損失弾性率)とE’(貯蔵弾性率)を測定し、tanδ(=E”/E’)とその最大値を求め、Tgを測定した。
装置:アイティー計測制御株式会社製 DVA-200
試料:5mm、長さ50mm(ギャップ20mm)
測定条件:引張りモード
測定温度:-25℃~220℃
昇温条件:5℃/min
周波数:1Hz
また、残留溶媒量は下記の式にしたがって求めた。
残留溶媒量(質量%)={(M-N)/N}×100
Mはウェブの任意時点での質量、NはMを測定したウェブを120℃で2時間乾燥させた時の質量である。
<紫外線硬化性接着剤1の調製>
下記に示す組成にて、紫外線硬化性接着剤を調製した。
(紫外線硬化性接着剤1の組成)
セロキサイド2021P(ダイセル(株)、多官能エポキシ化合物) ・・・100.0質量部
リカレジンDME-100(新日本理化(株)、多官能エポキシ化合物) ・・・28.6質量部
2-エチルヘキシルグリシジルエーテル(単官能エポキシ化合物) ・・・14.3質量部
CPI-100P(光酸発生剤、サンアプロ(株)) ・・・2.9質量部
Irgacure290(光酸発生剤、BASFジャパン(株)) ・・・5.7質量部
2-イソプロピルチオキサントン(光酸発生剤) ・・・1.4質量部
上記のVA位相差膜1を紫外線硬化性接着剤1を用いて、偏光子の片側に貼り付け、5秒後にVA位相差膜1側から紫外線を200mJの強度で照射し、紫外線硬化性接着剤1を硬化させ偏光子付きVA位相差膜1とした。
鹸化処理した樹脂膜303Aを、ポリビニルアルコール系接着剤を用いて、偏光子付きVA位相差膜1の偏光子側と貼り付け、偏光板303B1を作製した。
鹸化処理した樹脂膜303Aを、ポリビニルアルコール系接着剤を用いて、偏光子の片側に貼り付け、更に樹脂膜303Aを貼り合わせたのと反対側の面にVA位相差膜2を貼り合わせ、偏光板303B2を作製した。
市販の液晶表示装置FlexScan19インチカラー液晶モニターS1923-HBK(商品名、EIZO(株)製)の液晶パネルを取り出してフロント側の偏光板を剥がし、代わりに偏光板303B1のVA位相差膜側を、粘着剤(SK-2057、綜研化学株式会社製)を介して貼り付けた。こうして、液晶表示装置303C1を製造した。下記表に示すように樹脂膜の種類を変えた以外は同様にして液晶表示装置304C1、308C1を製造した。
市販の液晶表示装置FlexScan19インチカラー液晶モニターS1923-HBK(商品名、EIZO(株)製)の液晶パネルを取り出してフロント側の偏光板を剥がし、代わりに偏光板303B2のVA位相差膜側を、粘着剤(SK-2057、綜研化学株式会社製)を介して貼り付けた。こうして、液晶表示装置303C2を製造した。下記表に示すように樹脂膜の種類を変えた以外は同様にして液晶表示装置304C2、308C2を製造した。
下記に示す方法で有機エレクトロルミネッセンス表示装置を作製した。
(セルロースアシレート溶液の調製)
下記の組成物をミキシングタンクに投入し、加熱しながら攪拌して、各成分を溶解し、セルロースアシレート溶液を調製した。
セルロースアセテート(アセチル化度2.86) ・・・100質量部
メチレンクロライド(第1溶媒) ・・・320質量部
メタノール(第2溶媒) ・・・83質量部
1-ブタノール(第3溶媒) ・・・3質量部
トリフェニルフォスフェート ・・・7.6質量部
ビフェニルジフェニルフォスフェート ・・・3.8質量部
下記の組成物を分散機に投入し、攪拌して各成分を溶解し、マット剤分散液を調製した。
シリカ粒子分散液(平均粒径16nm、AEROSIL R972、日本アエロジル(株)製 ・・・10.0質量部
メチレンクロライド ・・・72.8質量部
メタノール ・・・3.9質量部
ブタノール ・・・0.5質量部
セルロースアシレート溶液 ・・・0.3質量部
下記の組成物をミキシングタンクに投入し、加熱しながら撹拌して、各成分を溶解し、紫外線吸収剤溶液を調製した。
紫外線吸収剤(式(UV-11)で表される構造の化合物) ・・・10.0質量部
紫外線吸収剤(式(UV-12)で表される構造の化合物) ・・・10.0質量部
メチレンクロライド ・・・55.7質量部
メタノール ・・・10質量部
ブタノール ・・・1.3質量部
セルロースアシレート溶液 ・・・12.9質量部
セルロースアシレート溶液の94.6質量部と、マット剤分散液の1.3質量部とを混合した混合液に、セルロースアシレート100質量部当たり、紫外線吸収剤(UV-1)および紫外線吸収剤(UV-2)がそれぞれ1.0質量部となるように、紫外線吸収剤溶液を加え、加熱しながら充分に撹拌して各成分を溶解し、ドープを調製した。得られたドープを30℃に加温し、流延ギーサーを通して直径3mのドラムである鏡面ステンレス支持体上に流延した。鏡面ステンレス支持体の表面温度は-5℃に設定し、塗布幅は1470mmとした。流延したドープ膜をドラム上で34℃の乾燥風を150m3/分で当てることにより乾燥させ、残留溶剤が150%の状態でドラムより剥離した。剥離の際、搬送方向(長手方向)に15%の延伸を行った。その後、フィルムの幅方向(流延方向に対して直交する方向)の両端をピンテンター(特開平04-001009号公報の図3に記載のピンテンター)で把持しながら搬送し、幅手方向には延伸処理を行わなかった。さらに、熱処理装置のロール間を搬送することによりさらに乾燥し、セルロースアシレートフィルム(T1)を製造した。作製した長尺状のセルロースアシレートフィルム(T1)の残留溶剤量は0.2%で、厚みは60μmで、波長550nmにおけるRe(面内レタデーション)とRth(厚さ方向のレタデーション)はそれぞれ0.8nm、40nmであった。
前述のセルロースアシレートフィルム(T1)を、温度60℃の誘電式加熱ロールを通過させ、フィルム表面温度を40℃に昇温した後に、フィルムのバンド面に下記に示す組成のアルカリ溶液を、バーコーターを用いて塗布量14ml/m2で塗布した。その後、アルカリ溶液が塗布されたセルロールアシレートフィルムを、110℃に加熱した(株)ノリタケカンパニーリミテド製のスチーム式遠赤外ヒーターの下に、10秒間搬送した。続いて、同じくバーコーターを用いて、得られたフィルム上に純水を3ml/m2塗布した。次いで、得られたフィルムに対して、ファウンテンコーターによる水洗とエアナイフによる水切りを3回繰り返した後に、フィルムを70℃の乾燥ゾーンに10秒間搬送して乾燥し、アルカリ鹸化処理したセルロースアシレートフィルムを作製した。
水酸化カリウム ・・・4.7質量部
水 ・・・15.8質量部
イソプロパノール ・・・63.7質量部
界面活性剤SF-1(C14H29O(CH2CH2O)20H) ・・・1.0質量部
プロピレングリコール ・・・14.8質量部
セルロースアシレートフィルム(T1)のアルカリ鹸化処理を行った面に、下記組成の配向膜塗布液を#14のワイヤーバーで連続的に塗布した。配向膜塗布液が塗布されたフィルムを、60℃の温風で60秒、さらに100℃の温風で120秒乾燥して、配向膜を形成した。使用した変性ポリビニルアルコールの鹸化度は88%であった。
下記構造の変性ポリビニルアルコール ・・・10質量部
水 ・・・308質量部
メタノール ・・・70質量部
イソプロパノール ・・・29質量部
光重合開始剤(Omnirad 2959、IGM Resins B.V.社製) ・・・0.8質量部
上記作製した配向膜に連続的にラビング処理を施した。このとき、長尺状のフィルムの長手方向と搬送方向は平行であり、フィルム長手方向(搬送方向)とラビングローラーの回転軸とのなす角度が72.5°とした(フィルム長手方向(搬送方向)を90°とし、配向膜側から観察してフィルム幅方向を基準(0°)に反時計回り方向を正の値で表すと、ラビングローラーの回転軸は-17.5°にある。言い換えれば、ラビングローラーの回転軸の位置は、フィルム長手方向を基準に、反時計回りに72.5°回転させた位置に該当する。)。
下記のディスコティック液晶化合物(A) ・・・80質量部
下記のディスコティック液晶化合物(B) ・・・20質量部
エチレンオキサイド変性トリメチロールプロパントリアクリレート(V#360、大阪有機化学(株)製) ・・・5質量部
光重合開始剤(Omnirad 907、IGM Resins B.V.社製) ・・・4質量部
下記のピリジニウム塩(A) ・・・2質量部
下記のポリマー(A) ・・・0.2質量部
下記のポリマー(B) ・・・0.1質量部
下記のポリマー(C) ・・・0.1質量部
メチルエチルケトン ・・・211質量部
(光学異方性層Bの形成)
上記(光学異方性層Aの作製)と同様の手順に従って、セルロースアシレートフィルム(T1)上に配向膜を形成し、配向膜に連続的にラビング処理を施した。このとき、長尺状のフィルムの長手方向と搬送方向は平行であり、フィルム長手方向(搬送方向)とラビングローラーの回転軸とのなす角度が102.5°とした(フィルム長手方向(搬送方向)を90°とし、配向膜側から観察してフィルム幅方向を基準に反時計回り方向を正の値で表すと、ラビングローラーの回転軸は12.5°。言い換えれば、ラビングローラーの回転軸の位置は、フィルム長手方向を基準に、反時計回りに102.5°回転させた位置に該当する。)。
上記ディスコティック液晶化合物(A) ・・・80質量部
上記ディスコティック液晶化合物(B) ・・・20質量部
エチレンオキサイド変性トリメチロールプロパントリアクリレート(V#360、大阪有機化学(株)製) ・・・10質量部
光重合開始剤(Omnirad 907、IGM Resins B.V.社製) ・・・5質量部
上記のピリジニウム塩(A) ・・・1質量部
上記のポリマー(A) ・・・0.2質量部
上記のポリマー(B) ・・・0.1質量部
上記のポリマー(C) ・・・0.1質量部
メチルエチルケトン ・・・348質量部
上記の作製した樹脂膜303A、304A、308Aを、2.3mol/Lの水酸化ナトリウム水溶液に、55℃で3分間浸漬した。室温(25℃)の水洗浴槽中で洗浄し、30℃で0.05mol/Lの硫酸を用いて中和した。再度、室温の水洗浴槽中で洗浄し、更に100℃の温風で乾燥した。
厚さ80μmのポリビニルアルコール(PVA)フィルムを、ヨウ素濃度0.05質量%のヨウ素水溶液中に30℃で60秒浸漬して染色し、次いでホウ酸濃度4質量%のホウ酸水溶液中に60秒浸漬している間に元の長さの5倍に縦延伸した後、50℃で4分間乾燥させて、厚さ19μmの偏光子を得た。
上記作製した偏光板中の偏光子(樹脂膜303Aのない)側に、粘着剤(SK-2057、綜研化学株式会社製)を塗布して粘着剤層を形成し、上記作製したセルロースアシレートフィルム、配向膜および光学異方性層Aを有するフィルムを、粘着剤層と光学異方性層Aとが密着するように、貼り合せた。その後、セルロースアシレートフィルムおよび配向膜を剥離して、積層体を得た。次に、得られた積層体中の光学異方性層Aに、粘着剤(SK-2057、綜研化学株式会社製)を塗布して、粘着剤層を形成した。次に、粘着剤層が配置された積層体と、上記作製したセルロースアシレートフィルム、配向膜および光学異方性層Bを有するフィルムとを、粘着剤層と光学異方性層Bとが密着するように、貼り合せた。その後、セルロースアシレートフィルムおよび配向膜を剥離した。上記手順により、偏光子、光学異方性層A(λ/2板)、および、光学異方性層B(λ/4板)がこの順に配置されている円偏光板303Dを作製した。なお、偏光子側から観察して、偏光子の透過軸を基準(0°)に反時計回りを正の値で表すと、λ/2板の遅相軸の角度は-17.5°であり、λ/4板の遅相軸の角度は-77.5°であった。つまり、光学異方性層A(λ/2板)の遅相軸と偏光子の透過軸とのなす角度は17.5°であり、光学異方性層A(λ/2板)の遅相軸と光学異方性層B(λ/4板)の遅相軸とのなす角度は60°であった。
市販の有機エレクトロルミネッセンス表示装置GALAXY S5(商品名、SAMSUNG社製)から、円偏光板付きタッチパネルを剥離し、さらにタッチパネルから円偏光板を剥がし、有機エレクトロルミネッセンス表示素子、タッチパネルおよび円偏光板をそれぞれ単離した。続いて、単離したタッチパネルを有機エレクトロルミネッセンス表示素子と再度貼合し、さらに上記作製した円偏光板303Eを空気が入らないようにしてタッチパネル上に貼合し、有機エレクトロルミネッセンス表示装置を作製した。表3のように樹脂膜の種類を変えた以外は同様にして液晶表示装置304E、308Eを製造した。
基材フィルム上に、下記に示す方法で、光学フィルム401Aを形成し、剥離性積層フィルム401Bを作製した。
(1)塗布液の調製
下記に示す組成で、光学フィルム401A形成用の塗布液1を調製した。得られた塗布液は絶対ろ過精度5μmのフィルタでろ過した。
AS-70(アクリロニトリル・スチレン共重合樹脂、新日鉄住金化学(株)製) ・・・100.0質量部
バイロン500(ポリエステル樹脂、東洋紡(株)製) ・・・0.9質量部
SMA2000P(スチレン・マレイン酸共重合体、川原油化(株)) ・・・4.2質量部
界面活性剤1 ・・・0.1質量部
紫外線吸収剤(化合物(1)-5) ・・・3.1質量部
紫外線吸収剤(比較化合物5) ・・・0.0質量部
酢酸メチル ・・・255.1質量部
アセトニトリル ・・・229.6質量部
エタノール ・・・25.5質量部
市販のポリエチレンテレフタレートフィルム(エンブレットS38、膜厚38μm、短波側の吸収端波長310nm、ユニチカ(株)製)を基材フィルムとして用い、塗布液1~6を使用し、膜厚が5μmとなるように光学フィルム401A~406Aを作製して、剥離性積層フィルム(膜厚43μm、短波側の吸収端波長310nm)を得た。具体的には、特開2006-122889号公報の実施例1記載のスロットダイを用いたダイコート法で、基材フィルム上に、搬送速度30m/分の条件で塗布液1を塗布し、105℃で30秒乾燥させた。その後、巻き取った。得られた剥離性積層フィルムを各実施例および比較例の剥離性積層フィルム401B~406Bとした。
下記に示す方法で偏光板を作製した。
(3-1)偏光板保護膜の鹸化処理
60μmのトリアセチルセルロースフィルム(フジタックTG60、富士フイルム社製)を、2.3mol/Lの水酸化ナトリウム水溶液に、55℃で3分間浸漬した。室温(25℃)の水洗浴槽中で洗浄し、30℃で0.05mol/Lの硫酸を用いて中和した。再度、室温の水洗浴槽中で洗浄し、更に100℃の温風で乾燥した。
樹脂膜303Aの代わりに上記60μmのトリアセチルセルロースフィルムを使用する以外は、偏光板303B1と同様にして偏光板4C1を作製した。
樹脂膜303Aの代わりに上記60μmのトリアセチルセルロースフィルムを使用する以外は、偏光板303B2と同様にして偏光板4C2を作製した。
剥離性積層フィルム402の光学フィルム側と偏光板4C-1のVA位相差膜側を紫外線硬化性接着剤1を介して貼り合わせた後、紫外線を200mJの強度で照射し、紫外線硬化性接着剤1を硬化させて剥離性積層フィルム付き偏光板402D1とした。
剥離性積層フィルム402の光学フィルム側と偏光板4C-2のVA位相差膜側を紫外線硬化性接着剤1を介して貼り合わせた後、紫外線を200mJの強度で照射し、紫外線硬化性接着剤1を硬化させて剥離性積層フィルム付き偏光板402D2とした。
偏光板402D1のエンブレットS38を剥離し、光学フィルムを露出させたのち、市販の液晶表示装置FlexScan19インチカラー液晶モニターS1923-HBK(商品名、EIZO(株)製)の液晶パネルを取り出してフロント側の偏光板を剥がし、代わりに偏光板402D1の光学フィルム側を、粘着剤(SK-2057、綜研化学株式会社製)を介して貼り付けた。こうして、液晶表示装置402E1を製造した。下記表に示すように剥離性積層フィルム付き偏光板の種類を変えた以外は同様にして液晶表示装置405E1、402E2、405E2を製造した。
下記に示す方法で、粘着剤501を作製した。
(1)塗工液の調製
アクリル樹脂(SKダイン-SF2147) ・・・100.0質量部
重合性化合物(TD-75) ・・・0.04質量部
シランカップリング剤(A-50) ・・・0.06質量部
紫外線吸収剤(化合物(1)-5) ・・・0.2質量部
紫外線吸収剤(比較化合物5) ・・・0.0質量部
SKダイン-SF2147:アクリル酸エステル共重合体。固形分濃度10~20質量%%、酢酸エチル、アクリル酸ブチル溶剤(綜研化学(株))
TD-75:トリレンジイソシアネートのトリメチロールブロパン付与体(綜研化学(株))
A-50:オルガノシラン(綜研化学(株))
離型処理が施されたポリエチレンテレフタレートフィルム(藤森工業(株)製、MASTACK AS3-310、以下セパレーターと略記する。)の離型処理面に、上記塗工液1~6を乾燥後の厚みが35μmになるようにアプリケーターを用いて塗工し、110℃で3分乾燥させた。その後セパレーターの離型処理面を貼合し、温度25℃湿度60%で24時間調湿し、粘着剤シート501A~506Aを作製した。
粘着剤シート501A~506Aのセパレーターを剥離し、厚さ1.1mmのイーグルガラスに貼合しガラス貼合粘着剤501B~506Bを作製した。上記で作成したガラス貼合粘着剤501B~506Bについてそれぞれ分光光度計UV3600(島津製作所社製)を用いて吸光度を測定した。また、波長405nmにおける吸光度を紫外線吸収剤の添加量(SKダイン-SF2147に対する質量%)で除算した際の値が50以上をA、25~50をB、25以下をCとして長波長の紫外線吸収能を評価した。値が大きいほど長波長の紫外線吸収能が高いことを意味する。結果を下記表の長波長の紫外線吸収能の欄に示す。
市販の液晶表示装置FlexScan19インチカラー液晶モニターS1923-HBK(商品名、EIZO(株)製)の液晶パネルを取り出してバックライト側の偏光板を剥がし、代わりに偏光板4C1のVA位相差膜側を、粘着剤シート502Aを介して貼り付けた。こうして、液晶表示装置502C1を製造した。また、粘着剤シートの種類および偏光板の種類を変えた以外は同様にして液晶表示装置505C1、502C2、505C2を製造した。
11~13:有機エレクトロルミネッセンス表示装置
22、49、176:本発明の紫外線吸収剤入り偏光板保護膜
56、75:本発明の紫外線吸収剤入りインナー保護膜(位相差膜)
88、107、206:本発明の紫外線吸収剤入り光学部材(光学フィルム)
121、138、194:本発明の紫外線吸収剤入り粘着剤または接着剤
145、174:本発明の紫外線吸収剤入り機能性層
21、35、36、50、51、65、66、80、81、97、98、114、115、129、130、144、159、160、175、186、197:機能性層
23、25、27、29、31、33、38、40、42、44、46、48、53、55、57、59、61、63、68、70、72、74、76、78、83、85、87、89、91、93、95、100、102、104、106、108、110、112、117、119、123、125、127、132、134、136、140、142、147、149、151、153、155、157、162、164、166、168、170、172、177、179、181、183、188、190、192、199、201、203、205、207:接着剤または粘着剤
24、32、39、47、54、62、69、77、84、94、101、111、118、126、133、141、148、156、163、171、178、189、200:偏光子
26、30、41、45、56、60、71、75、86、92、103、109、120、124、135、139、150、154、165、169:位相差膜
28、43、58、73、90、105、122、137、152、167:液晶セル
34、37、52、64、67、79、82、96、99、113、116、128、1 31、143、146、158、161、173、187、198:偏光板保護膜
180、191、202:2/λ板
182、193、204:4/λ板
184、195、208:タッチパネル
185、196、209:有機エレクトロルミネッセンス発光素子
Claims (15)
- 式(1)で表される化合物と、樹脂とを含む樹脂組成物;
R3およびR6は、各々独立にアルコキシ基、アシルオキシ基、カルバモイルオキシ基またはアルコキシカルボニルオキシ基を表し、
R4は、アルキル基、アリール基、アルコキシ基、アリールオキシ基、アシルオキシ基、アルキルアミノ基、アニリノ基、アシルアミノ基、アルキルスルホニルアミノ基、アリールスルホニルアミノ基、アルキルチオ基またはアリールチオ基を表し、
R5は、水素原子、アルキル基、アリール基、アルコキシ基、アリールオキシ基、アシルオキシ基、アルキルアミノ基、アニリノ基、アシルアミノ基、アルキルスルホニルアミノ基、アリールスルホニルアミノ基、アルキルチオ基またはアリールチオ基を表す;
R1とR2は互いに結合して環を形成していてもよい;
R3とR4は互いに結合して環を形成していてもよい;
R4とR5は互いに結合して環を形成していてもよい;
R5とR6は互いに結合して環を形成していてもよい;
ただし、R3およびR6がそれぞれ独立にアシルオキシ基またはカルバモイルオキシ基の場合、R4およびR5の少なくとも一方は、アリール基、アルコキシ基、アリールオキシ基、アシルオキシ基、アルキルアミノ基、アニリノ基、アシルアミノ基、アルキルスルホニルアミノ基、アリールスルホニルアミノ基、アルキルチオ基またはアリールチオ基である。 - 式(1)中、R4はアルキル基、アリール基、アルコキシ基またはアリールオキシ基であり、R5は水素原子、アルキル基、アリール基、アルコキシ基またはアリールオキシ基である、請求項1に記載の樹脂組成物。
- 式(1)中、R3およびR6の少なくとも一方はアルコキシ基である、請求項1または2に記載の樹脂組成物。
- 前記式(1)で表される化合物が、下記式(1a)で表される化合物である、請求項1に記載の樹脂組成物;
R3aおよびR6aは、各々独立にアルコキシ基またはアシルオキシ基を表し、
R4aはアルキル基またはアルコキシ基を表し、
R5aは、水素原子、アルキル基またはアルコキシ基を表す;
R1aとR2aは互いに結合して環を形成していてもよい;
R3aとR4aは互いに結合して環を形成していてもよい;
R4aとR5aは互いに結合して環を形成していてもよい;
R5aとR6aは互いに結合して環を形成していてもよい;
ただし、R3aおよびR6aがアシルオキシ基の場合、R4aおよびR5aの少なくとも一方はアルコキシ基である。 - 更に、式(2)で表される化合物を含む、請求項1~4のいずれか1項に記載の樹脂組成物;
R13およびR16は、各々独立にヒドロキシ基、アルコキシ基、アリールオキシ基、アシルオキシ基、カルバモイルオキシ基、アルコキシカルボニルオキシ基、アリールオキシカルボニルオキシ基、スルフィニルオキシ基またはスルホニルオキシ基を表し、
R14はアルキル基、アリール基、アルコキシ基、アリールオキシ基、アシルオキシ基、アルキルアミノ基、アニリノ基、アシルアミノ基、アルキルスルホニルアミノ基、アリールスルホニルアミノ基、アルキルチオ基またはアリールチオ基を表し、
R15は水素原子、アルキル基、アリール基、アルコキシ基、アリールオキシ基、アシルオキシ基、アルキルアミノ基、アニリノ基、アシルアミノ基、アルキルスルホニルアミノ基、アリールスルホニルアミノ基、アルキルチオ基またはアリールチオ基を表す;
R11とR12は互いに結合して環を形成していてもよい;
R13とR14は互いに結合して環を形成していてもよい;
R14とR15は互いに結合して環を形成していてもよい;
R15とR16は互いに結合して環を形成していてもよい;
ただし、R13およびR16の少なくとも一方はヒドロキシ基である。 - 更に、前記式(1)で表される化合物以外の他の紫外線吸収剤を含む、請求項1~5のいずれか1項に記載の樹脂組成物。
- 前記樹脂が、(メタ)アクリル樹脂、ポリスチレン樹脂、ポリエステル樹脂、ポリウレタン樹脂、ポリチオウレタン樹脂、ポリイミド樹脂、エポキシ樹脂、ポリカーボネート樹脂およびセルロースアシレート樹脂から選ばれる少なくとも1種である、請求項1~6のいずれか1項に記載の樹脂組成物。
- 請求項1~7のいずれか1項に記載の樹脂組成物を用いて得られる硬化物。
- 式(1)で表される化合物を含む紫外線吸収剤;
R3およびR6は、各々独立にアルコキシ基、アシルオキシ基、カルバモイルオキシ基またはアルコキシカルボニルオキシ基を表し、
R4は、アルキル基、アリール基、アルコキシ基、アリールオキシ基、アシルオキシ基、アルキルアミノ基、アニリノ基、アシルアミノ基、アルキルスルホニルアミノ基、アリールスルホニルアミノ基、アルキルチオ基またはアリールチオ基を表し、
R5は、水素原子、アルキル基、アリール基、アルコキシ基、アリールオキシ基、アシルオキシ基、アルキルアミノ基、アニリノ基、アシルアミノ基、アルキルスルホニルアミノ基、アリールスルホニルアミノ基、アルキルチオ基またはアリールチオ基を表す;
R1とR2は互いに結合して環を形成していてもよい;
R3とR4は互いに結合して環を形成していてもよい;
R4とR5は互いに結合して環を形成していてもよい;
R5とR6は互いに結合して環を形成していてもよい;
ただし、R3およびR6がそれぞれ独立にアシルオキシ基またはカルバモイルオキシ基の場合、R4およびR5の少なくとも一方は、アリール基、アルコキシ基、アリールオキシ基、アシルオキシ基、アルキルアミノ基、アニリノ基、アシルアミノ基、アルキルスルホニルアミノ基、アリールスルホニルアミノ基、アルキルチオ基またはアリールチオ基である。 - 更に、式(2)で表される化合物を含む、請求項9に記載の紫外線吸収剤;
R13およびR16は、各々独立にヒドロキシ基、アルコキシ基、アリールオキシ基、アシルオキシ基、カルバモイルオキシ基、アルコキシカルボニルオキシ基、アリールオキシカルボニルオキシ基、スルフィニルオキシ基またはスルホニルオキシ基を表し、
R14はアルキル基、アリール基、アルコキシ基、アリールオキシ基、アシルオキシ基、アルキルアミノ基、アニリノ基、アシルアミノ基、アルキルスルホニルアミノ基、アリールスルホニルアミノ基、アルキルチオ基またはアリールチオ基を表し、
R15は水素原子、アルキル基、アリール基、アルコキシ基、アリールオキシ基、アシルオキシ基、アルキルアミノ基、アニリノ基、アシルアミノ基、アルキルスルホニルアミノ基、アリールスルホニルアミノ基、アルキルチオ基またはアリールチオ基を表す;
R11とR12は互いに結合して環を形成していてもよい;
R13とR14は互いに結合して環を形成していてもよい;
R14とR15は互いに結合して環を形成していてもよい;
R15とR16は互いに結合して環を形成していてもよい;
ただし、R13およびR16の少なくとも一方はヒドロキシ基である。 - 請求項9または10に記載の紫外線吸収剤を含む紫外線カットフィルタ。
- 請求項9または10に記載の紫外線吸収剤を含むレンズ。
- 請求項9または10に記載の紫外線吸収剤を含む保護材。
- 式(1a)で表される化合物;
R3aおよびR6aは、各々独立にアルコキシ基またはアシルオキシ基を表し、
R4aはアルキル基またはアルコキシ基を表し、
R5aは、水素原子、アルキル基またはアルコキシ基を表す;
R1aとR2aは互いに結合して環を形成していてもよい;
R3aとR4aは互いに結合して環を形成していてもよい;
R4aとR5aは互いに結合して環を形成していてもよい;
R5aとR6aは互いに結合して環を形成していてもよい;
ただし、R3aおよびR6aがアシルオキシ基の場合、R4aおよびR5aの少なくとも一方はアルコキシ基である。 - 式(2a)で表される化合物と、ハロゲン化アルキル化合物またはカルボン酸ハロゲン化物とを反応させる工程を含む、式(1a)で表される化合物の合成方法;
R3aおよびR6aは、各々独立にアルコキシ基またはアシルオキシ基を表し、
R4aはアルキル基またはアルコキシ基を表し、
R5aは、水素原子、アルキル基またはアルコキシ基を表す;
R1aとR2aは互いに結合して環を形成していてもよい;
R3aとR4aは互いに結合して環を形成していてもよい;
R4aとR5aは互いに結合して環を形成していてもよい;
R5aとR6aは互いに結合して環を形成していてもよい;
ただし、R3aおよびR6aがアシルオキシ基の場合、R4aおよびR5aの少なくとも一方はアルコキシ基である;
R14aはアルキル基またはアルコキシ基を表し、
R15aは水素原子、アルキル基またはアルコキシ基を表す;
R14aとR15aは互いに結合して環を形成していてもよい。
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CN114867790A (zh) | 2022-08-05 |
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