Resin composition, cured product, ultraviolet absorber, ultraviolet cut filter, lens, protective material, compound, and method for synthesizing the compound

Abstract

The present invention provides a resin composition comprising a compound represented by formula (1) and a resin. 1 and R 2 Each independently represents an alkyl group, etc., R 3 and R 6 Each independently represents an alkoxy group, etc., R 4 represents an alkyl group, an aryl group, an alkoxy group, an aryloxy group, etc., R 5 represents a hydrogen atom, an alkyl group, an aryl group, an alkoxy group, an aryloxy group, etc. The present invention also provides a cured product, an ultraviolet absorber, an ultraviolet cut filter, a lens, a protective material, a compound, and a method for synthesizing the compound. #imgabs0#

Description

Technical Field

[0001] The present invention relates to a resin composition. More specifically, it relates to a resin composition containing a benzodithiol compound. Furthermore, the present invention relates to a cured product, a UV absorber, a UV cut filter, a lens, a protective material, a compound, and a method for synthesizing the compound. Background Art

[0002] Benzodithiol compounds have excellent ultraviolet absorption properties and are used as ultraviolet absorbers, etc. For example, Patent Document 1 describes the use of a specific benzodithiol compound as an ultraviolet absorber.

[0003] Previous technical literature

[0004] Patent Literature

[0005] Patent Document 1: International Publication No. 2019 / 159570 Summary of the Invention

[0006] Technical issues to be solved by the invention

[0007] One of the properties required of ultraviolet absorbers is low coloration. Furthermore, in recent years, they are also required to have high absorption capabilities even for ultraviolet rays with longer wavelengths, such as around 400 nm.

[0008] Therefore, an object of the present invention is to provide 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 the compound, which can produce a cured product having excellent absorption ability for ultraviolet rays around a wavelength of 400 nm.

[0009] Means for solving technical problems

[0010] The present inventors have conducted extensive research on compounds having a skeleton represented by formula (1). As a result, they have discovered that a compound represented by formula (1) described below has excellent absorption capacity for ultraviolet rays having a wavelength of approximately 400 nm and exhibits minimal coloration, and is useful as an ultraviolet absorber. Consequently, the present invention has been completed. Therefore, the present invention provides the following.

[0011] <1> A resin composition comprising a compound represented by formula (1) and a resin;

[0012] [Chemical Formula 1]

[0013]

[0014] In formula (1), R 1 and R 2 Each independently represents an alkyl group, an aryl group or a heterocyclic group,

[0015] R 3 and R 6 each independently represents an alkoxy group, an acyloxy group, a carbamoyloxy group or an alkoxycarbonyloxy group,

[0016] 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,

[0017] 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;

[0018] R 1 With R 2 can bond to each other to form a ring;

[0019] R 3 With R 4 can bond to each other to form a ring;

[0020] R 4 With R 5 can bond to each other to form a ring;

[0021] R 5 With R 6 can bond to each other to form a ring;

[0022] Among them, R 3 and R 6 When each independently represents an acyloxy group or a carbamoyloxy group, R 4 and R 5 At least one of them is 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.

[0023] <2> The resin composition according to <1>, wherein

[0024] In formula (1), 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.

[0025] <3> The resin composition according to <1> or <2>, wherein

[0026] In formula (1), R 3 and R 6 At least one of them is an alkoxy group.

[0027] <4> The resin composition according to <1>, wherein

[0028] The compound represented by the above formula (1) is a compound represented by the following formula (1a);

[0029] [Chemical Formula 2]

[0030]

[0031] In formula (1a), R 1a and R 2a Each independently represents an alkyl group,

[0032] R 3a and R 6a Each independently represents an alkoxy group or an acyloxy group,

[0033] R 4a represents an alkyl group or an alkoxy group,

[0034] R 5a represents a hydrogen atom, an alkyl group or an alkoxy group;

[0035] R 1a With R 2a can bond to each other to form a ring;

[0036] R 3a With R 4a can bond to each other to form a ring;

[0037] R 4a With R 5a can bond to each other to form a ring;

[0038] R 5a With R 6a can bond to each other to form a ring;

[0039] Among them, R 3a and R 6a When it is an acyloxy group, R 4a and R 5a At least one of them is an alkoxy group.

[0040] <5> The resin composition according to any one of <1> to <4>, further comprising a compound represented by formula (2);

[0041] [Chemical Formula 3]

[0042]

[0043] In formula (2), R 11 and R 12 Each independently represents an alkyl group, an aryl group or a heterocyclic group,

[0044] R 13 and R 16 each independently represents a hydroxyl 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,

[0045] R 14 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,

[0046] 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;

[0047] R 11 With R 12 can bond to each other to form a ring;

[0048] R 13 With R 14 can bond to each other to form a ring;

[0049] R 14 With R 15 can bond to each other to form a ring;

[0050] R 15 With R 16 can bond to each other to form a ring;

[0051] Among them, R 13 and R 16 At least one of them is a hydroxyl group.

[0052] <6> The resin composition according to any one of <1> to <5>, further comprising another ultraviolet absorber other than the compound represented by the above formula (1).

[0053] <7> The resin composition according to any one of <1> to <6>, wherein

[0054] The resin is at least one selected from the group consisting of (meth)acrylic resin, polystyrene resin, polyester resin, polyurethane resin, polythiourethane resin, polyimide resin, epoxy resin, polycarbonate resin, and cellulose acylate resin.

[0055] <8> A cured product obtained by using the resin composition according to any one of <1> to <7>.

[0056] <9> An ultraviolet absorber comprising a compound represented by formula (1);

[0057] [Chemical Formula 4]

[0058]

[0059] In formula (1), R 1 and R 2 Each independently represents an alkyl group, an aryl group or a heterocyclic group,

[0060] R 3 and R 6 each independently represents an alkoxy group, an acyloxy group, a carbamoyloxy group or an alkoxycarbonyloxy group,

[0061] 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,

[0062] 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;

[0063] R 1 With R 2 can bond to each other to form a ring;

[0064] R 3 With R 4 can bond to each other to form a ring;

[0065] R 4 With R 5 can bond to each other to form a ring;

[0066] R 5 With R 6 can bond to each other to form a ring;

[0067] Among them, R 3 and R 6 When each independently represents an acyloxy group or a carbamoyloxy group, R 4 and R 5 At least one of them is 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.

[0068] <10> The ultraviolet absorber according to <9>, further comprising a compound represented by formula (2);

[0069] [Chemical Formula 5]

[0070]

[0071] In formula (2), R 11 and R 12 Each independently represents an alkyl group, an aryl group or a heterocyclic group,

[0072] R 13 and R 16 each independently represents a hydroxyl 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,

[0073] R 14 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,

[0074] 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;

[0075] R 11 With R 12 can bond to each other to form a ring;

[0076] R 13 With R 14 can bond to each other to form a ring;

[0077] R 14 With R 15 can bond to each other to form a ring;

[0078] R 15 With R 16 can bond to each other to form a ring;

[0079] Among them, R 13 and R 16 At least one of them is a hydroxyl group.

[0080] <11> An ultraviolet cut filter comprising the ultraviolet absorber according to <9> or <10>.

[0081] <12> A lens comprising the ultraviolet absorber according to <9> or <10>.

[0082] <13> A protective material comprising the ultraviolet absorber according to <9> or <10>.

[0083] <14> A compound represented by formula (1a), wherein

[0084] [Chemical Formula 6]

[0085]

[0086] In formula (1a), R 1a and R 2a Each independently represents an alkyl group,

[0087] R 3a and R 6a Each independently represents an alkoxy group or an acyloxy group,

[0088] R 4a represents an alkyl group or an alkoxy group,

[0089] R 5a represents a hydrogen atom, an alkyl group or an alkoxy group;

[0090] R 1a With R 2a can bond to each other to form a ring;

[0091] R 3a With R 4a can bond to each other to form a ring;

[0092] R 4a With R 5a can bond to each other to form a ring;

[0093] R 5a With R 6a can bond to each other to form a ring;

[0094] Among them, R 3a and R 6a When it is an acyloxy group, R 4a and R 5a At least one of them is an alkoxy group.

[0095] <15> A method for synthesizing a compound represented by formula (1a), comprising reacting a compound represented by formula (2a) with a halogenated alkyl compound or a carboxylic acid halide;

[0096] [Chemical Formula 7]

[0097]

[0098] In formula (1a), R 1a and R 2a Each independently represents an alkyl group,

[0099] R 3a and R 6a Each independently represents an alkoxy group or an acyloxy group,

[0100] R 4a represents an alkyl group or an alkoxy group,

[0101] R 5arepresents a hydrogen atom, an alkyl group or an alkoxy group;

[0102] R 1a With R 2a can bond to each other to form a ring;

[0103] R 3a With R 4a can bond to each other to form a ring;

[0104] R 4a With R 5a can bond to each other to form a ring;

[0105] R 5a With R 6a can bond to each other to form a ring;

[0106] Among them, R 3a and R 6a When it is an acyloxy group, R 4a and R 5a At least one of them is an alkoxy group;

[0107] [Chemical Formula 8]

[0108]

[0109] In formula (2a), R 11a and R 12a Each independently represents an alkyl group,

[0110] R 14a represents an alkyl group or an alkoxy group,

[0111] R 15a represents a hydrogen atom, an alkyl group or an alkoxy group;

[0112] R 14a With R 15a They may be bonded to each other to form a ring.

[0113] Effects of the Invention

[0114] The present invention can provide a resin composition, cured product, ultraviolet absorber, ultraviolet cut filter, lens, protective material, compound, and compound synthesis method capable of producing a cured product having excellent ability to absorb ultraviolet rays having a wavelength of around 400 nm. BRIEF DESCRIPTION OF THE DRAWINGS

[0115] Figure 1 This is one embodiment of a liquid crystal display device and is a schematic diagram showing a structure in which the ultraviolet absorber of the present invention is added to a front polarizer protective film.

[0116] Figure 2This is an embodiment of a liquid crystal display device and is a schematic diagram showing a structure in which the ultraviolet absorber of the present invention is added to a polarizer protective film on the backlight side.

[0117] Figure 3 This is an embodiment of a liquid crystal display device and is a schematic diagram showing a structure in which the ultraviolet absorber of the present invention is added to a front inner protective film.

[0118] Figure 4 This is an embodiment of a liquid crystal display device and is a schematic diagram showing a structure in which the ultraviolet absorber of the present invention is added to an inner protective film on the backlight side.

[0119] Figure 5 This is one embodiment of a liquid crystal display device, and is a schematic diagram showing a structure in which an optical film containing the ultraviolet absorber of the present invention is bonded to a front retardation film via an adhesive or a pressure-sensitive adhesive.

[0120] Figure 6 This is one embodiment of a liquid crystal display device, and is a schematic diagram showing a structure in which an optical film containing the ultraviolet absorber of the present invention is bonded to a retardation film on the backlight side via an adhesive or a pressure-sensitive adhesive.

[0121] Figure 7 This is an embodiment of a liquid crystal display device and is a schematic diagram showing a structure in which the ultraviolet absorber of the present invention is added to a front-side adhesive or a pressure-sensitive adhesive.

[0122] Figure 8 This is an embodiment of a liquid crystal display device and is a schematic diagram showing a structure in which the ultraviolet absorber of the present invention is added to a binder or adhesive on the backlight side.

[0123] Figure 9 This is one embodiment of a liquid crystal display device and is a schematic diagram showing a structure in which the ultraviolet absorber of the present invention is added to a front-side functional layer.

[0124] Figure 10 This is one embodiment of a liquid crystal display device and is a schematic diagram showing a structure in which the ultraviolet absorber of the present invention is added to a functional layer on the backlight side.

[0125] Figure 11 This is an embodiment of an organic electroluminescent display device and is a schematic diagram showing a structure in which the ultraviolet absorber of the present invention is added to a polarizer protective film.

[0126] Figure 12 This is an embodiment of an organic electroluminescent display device and is a schematic diagram showing a structure in which the ultraviolet absorber of the present invention is added to a binder or an adhesive.

[0127] Figure 13This is an embodiment of an organic electroluminescent display device, and is a schematic diagram showing a structure in which an optical film containing the ultraviolet absorber of the present invention is bonded to a touch panel via an adhesive or a pressure-sensitive adhesive. DETAILED DESCRIPTION

[0128] Hereinafter, the contents of the present invention will be described in detail.

[0129] In the notation of groups (atomic groups) in this specification, the notation not indicating "substituted" or "unsubstituted" includes both groups having no substituent and groups having substituent. For example, "alkyl" includes not only alkyl groups having no substituent (unsubstituted alkyl) but also alkyl groups having substituent (substituted alkyl).

[0130] In this specification, the numerical range expressed using "to" means a range including the numerical values described before and after "to" as the lower limit and the upper limit.

[0131] In this specification, the total solid content means the total amount of components excluding the solvent from the total components of the resin composition.

[0132] In this specification, “(meth)acrylate” means both or either acrylate and methacrylate, “(meth)acrylic acid” means both or either acrylic acid and methacrylic acid, “(meth)allyl” means both or either allyl and methallyl, and “(meth)acryloyl” means both or either acryloyl and methacryloyl.

[0133] In this specification, the term "process" includes not only independent processes but also processes that cannot be clearly distinguished from other processes as long as the intended effect of the process can be achieved.

[0134] In this specification, 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).

[0135] <Resin composition>

[0136] The resin composition of the present invention is characterized by comprising a compound represented by formula (1) and a resin.

[0137] The compound represented by formula (1) is a compound that has excellent absorption of ultraviolet rays having a wavelength of around 400 nm and exhibits little coloration. Therefore, the resin composition of the present invention can produce a cured product having excellent absorption of ultraviolet rays having a wavelength of around 400 nm.

[0138] Furthermore, the compound represented by formula (1) has good compatibility with resins and the like, and can also suppress unevenness of the surface of the cured product. The detailed reason for this effect is not clear, but it is speculated that the compound represented by formula (1) is easily sterically repelled in R 3 With R 4 It is speculated that the generation of this distortion reduces the crystallinity of the compound and improves its compatibility with resins and the like.

[0139] Hereinafter, the resin composition of the present invention will be described in detail.

[0140] <<Compound represented by formula (1) (Compound (1))>>

[0141] The resin composition of the present invention contains a compound represented by formula (1) (hereinafter, also referred to as compound (1)).

[0142] [Chemical Formula 9]

[0143]

[0144] In formula (1), R 1 and R 2 Each independently represents an alkyl group, an aryl group or a heterocyclic group,

[0145] R 3 and R 6 each independently represents an alkoxy group, an acyloxy group, a carbamoyloxy group or an alkoxycarbonyloxy group,

[0146] 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,

[0147] 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;

[0148] R 1 With R 2 can bond to each other to form a ring;

[0149] R 3 With R 4 can bond to each other to form a ring;

[0150] R 4 With R 5 can bond to each other to form a ring;

[0151] R 5 With R 6can bond to each other to form a ring;

[0152] Among them, R 3 and R 6 When each independently represents an acyloxy group or a carbamoyloxy group, R 4 and R 5 At least one of them is 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.

[0153] In formula (1), R 1 and R 2 Each independently represents an alkyl group, an aryl group or a heterocyclic group, preferably an alkyl group or an aryl group. 1 and R 2 Furthermore, from the viewpoint of the absorption of ultraviolet rays with a wavelength of about 400 nm, it is preferred that R 1 and R 2 are each independently an aryl group.

[0154] R 1 and R 2 The number of carbon atoms in the alkyl group is preferably 1 to 30, more preferably 1 to 20, even more 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 those described below in the substituent T.

[0155] R 1 and R 2 The number of carbon atoms in the aryl group represented is preferably 6 to 40, more preferably 6 to 30, even more preferably 6 to 20, particularly preferably 6 to 15, and most preferably 6 to 12. The aryl group is preferably phenyl or naphthyl, more preferably phenyl. The aryl group may have a substituent. Examples of the substituent include those described below in the substituent T.

[0156] R 1 and R 2The heterocyclic ring in the heterocyclic group represented by the present invention preferably includes a 5-membered or 6-membered saturated or unsaturated heterocyclic ring. An aliphatic ring, an aromatic ring, or another heterocyclic ring may be condensed in the heterocyclic ring. Examples of heteroatoms constituting the heterocyclic ring include B, N, O, S, Se, and Te, preferably N, O, and S. The carbon atoms in the heterocyclic ring preferably have a free valence (monovalent) (the heterocyclic group is bonded to a carbon atom). The preferred number of carbon atoms in the heterocyclic group is 1 to 40, more preferably 1 to 30, and even more preferably 1 to 20. Examples of saturated heterocyclic rings in the heterocyclic group include a pyrrolidine ring, a morpholine ring, a 2-boron-1,3-dioxolane ring, and a 1,3-thiazolidine ring. Examples of unsaturated heterocyclic rings 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 groups described in the substituent T described later.

[0157] R 1 With R 2 They may bond to each other to form a ring. 1 With R 2 The ring formed by the bonding is preferably a 5-membered ring or a 6-membered ring. 1 With R 2 The ring formed by the bonding may have a substituent. Examples of the substituent include the groups described in the substituent T described later.

[0158] In formula (1), R 3 and R 6 Each independently represents an alkoxy group, an acyloxy group, a carbamoyloxy group or an alkoxycarbonyloxy group, preferably an alkoxy group or an acyloxy group, and is more preferably R 3 and R 6 At least one of them is an alkoxy group. According to the research of the present inventors, it was found that the substituents on the benzene ring of benzodithiol with higher electron donating ability are more likely to shift the maximum absorption wavelength of the compound to the long wavelength side. Since the alkoxy group is a substituent with higher electron donating ability, it is speculated that it is more likely to shift the maximum absorption wavelength of the compound to the long wavelength side. In particular, R 3 and R 6 Both are alkoxy groups.

[0159] R 3 and R 6 The number of carbon atoms in the alkoxy group is preferably 1 to 30, more preferably 1 to 20, even more preferably 1 to 15, particularly preferably 1 to 10, and most preferably 1 to 8. The alkoxy group may be either linear or branched. The alkoxy group may have a substituent. Examples of the substituent include those described below in the substituent T.

[0160] R 3 and R 6 The number of carbon atoms in the acyloxy group 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 those described in the substituent T below.

[0161] R 3 and R 6 The number of carbon atoms in the carbamoyloxy group is preferably 2 to 30, more preferably 2 to 20, even more preferably 2 to 15, particularly preferably 2 to 10, and most preferably 2 to 8. The carbamoyloxy group may be either linear or branched. The carbamoyloxy group may have a substituent. Examples of the substituent include those described below for the substituent T.

[0162] R 3 and R 6 The number of carbon atoms in the alkoxycarbonyloxy group is preferably 2 to 30, more preferably 2 to 20, even more 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 those described below for the substituent T.

[0163] In formula (1), 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, and 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.

[0164] R 4 and R 5 The number of carbon atoms in the alkyl group is preferably 1 to 30, more preferably 1 to 20, even more 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 those described below in the substituent T.

[0165] R 4 and R 5 The number of carbon atoms in the aryl group represented is preferably 6 to 40, more preferably 6 to 30, even more preferably 6 to 20, particularly preferably 6 to 15, and most preferably 6 to 12. The aryl group is preferably phenyl or naphthyl, more preferably phenyl. The aryl group may have a substituent. Examples of the substituent include those described below in the substituent T.

[0166] R 4 and R 5 The number of carbon atoms in the alkoxy group is preferably 1 to 30, more preferably 1 to 20, even more preferably 1 to 15, particularly preferably 1 to 10, and most preferably 1 to 8. The alkoxy group may be either linear or branched. The alkoxy group may have a substituent. Examples of the substituent include those described below in the substituent T.

[0167] R 4 and R 5 The number of carbon atoms in the aryloxy group 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 aryloxy group may have a substituent. Examples of the substituent include those described in the substituent T below.

[0168] R 4 and R 5 The number of carbon atoms in the aniline group represented 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 aniline group may have a substituent. Examples of the substituent include those described in the substituent T below.

[0169] R 4 and R 5 The number of carbon atoms in the acylamino group 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 those described in the substituent T below.

[0170] R 4 and R 5 The number of carbon atoms in the alkylsulfonylamino group 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 those described in the substituent T below.

[0171] R 4 and R 5 The number of carbon atoms in the arylsulfonylamino group is preferably 6 to 40, more preferably 6 to 30, even more preferably 6 to 20, particularly preferably 6 to 15, and most preferably 6 to 12. The arylsulfonylamino group may have a substituent. Examples of the substituent include those described in the substituent T below.

[0172] R 4 and R 5The number of carbon atoms in the alkylthio group is preferably 1 to 30, more preferably 1 to 20, even more 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 those described below for the substituent T.

[0173] R 4 and R 5 The number of carbon atoms in the arylthio group represented is preferably 6 to 40, more preferably 6 to 30, even more 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 those described in the substituent T described below.

[0174] In formula (1), R 3 With R 4 Can bond with each other to form a ring, R 4 With R 5 Can bond with each other to form a ring, R 5 With R 6 These groups may be bonded to each other to form a ring. The ring formed by these groups bonding to each other is preferably a 5-membered ring or a 6-membered ring. The ring formed by these groups bonding to each other may have a substituent. As a substituent, the group described in the substituent T described below can be given.

[0175] From the viewpoint of suppressing coloration and more easily improving the absorption of ultraviolet rays near a wavelength of 400 nm, R is preferred. 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, more preferably R 4 is an alkyl group or an alkoxy group, R 5 is a hydrogen atom, an alkyl group or an alkoxy group.

[0176] Furthermore, from the viewpoint of ease of synthesis, R 4 is an alkyl group, an aryl group, an alkoxy group or an aryloxy group, R 5 is a hydrogen atom, more preferably R 4 is an alkyl group or an alkoxy group, R 5 A hydrogen atom.

[0177] Furthermore, from the viewpoint of increasing the wavelength of the absorption spectrum, it is preferred that R 4 and R 5 Each is independently an alkyl group, an aryl group, an alkoxy group or an aryloxy group, more preferably an alkyl group or an alkoxy group, and further preferably R 4 and R 5 Both are alkyl or R 4 and R 5 Both are alkoxy groups.

[0178] Furthermore, R is also preferred. 4 With R 5 They are bonded to each other to form a ring.

[0179] However, in formula (1), R 3 and R 6 When it is an acyloxy group, R 4 and R 5 At least one of them is 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, preferably an aryl group, an alkoxy group, an aryloxy group or an acyloxy group, more preferably an alkoxy group.

[0180] The compound represented by formula (1) (compound (1)) is preferably a compound represented by the following formula (1a).

[0181] [Chemical Formula 10]

[0182]

[0183] In formula (1a), R 1a and R 2a Each independently represents an alkyl group,

[0184] R 3a and R 6a Each independently represents an alkoxy group or an acyloxy group,

[0185] R 4a represents an alkyl group or an alkoxy group,

[0186] R 5a represents a hydrogen atom, an alkyl group or an alkoxy group;

[0187] R 1a With R 2a can bond to each other to form a ring;

[0188] R 3a With R 4a can bond to each other to form a ring;

[0189] R 4a With R 5a can bond to each other to form a ring;

[0190] R 5a With R 6a can bond to each other to form a ring;

[0191] Among them, R 3a and R 6a When it is an acyloxy group, R 4a and R 5a At least one of them is an alkoxy group.

[0192] R 1a and R 2a The number of carbon atoms in the alkyl group is preferably 1 to 30, more preferably 1 to 20, even more 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 those described below in the substituent T.

[0193] R 1a With R 2a They may bond to each other to form a ring. 1a With R 2a The ring formed by the bonding is preferably a 5-membered ring or a 6-membered ring. 1a With R 2a The ring formed by the bonding may have a substituent. Examples of the substituent include the groups described in the substituent T described later.

[0194] In formula (1a), R 3a and R 6a Each independently represents an alkoxy group or an acyloxy group. From the perspective of suppressing coloration and more easily improving the absorption of ultraviolet rays with a wavelength of around 400 nm, R 3a and R 6a At least one of them is an alkoxy group, more preferably R 3a and R 6a Both are alkoxy groups.

[0195] R 3a and R 6a The number of carbon atoms in the alkoxy group is preferably 1 to 30, more preferably 1 to 20, even more preferably 1 to 15, particularly preferably 1 to 10, and most preferably 1 to 8. The alkoxy group may be either linear or branched. The alkoxy group may have a substituent. Examples of the substituent include those described below in the substituent T.

[0196] R 3a and R 6a The number of carbon atoms in the acyloxy group 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 those described in the substituent T below.

[0197] In formula (1a), R 4a represents an alkyl group or an alkoxy group, R 5a represents a hydrogen atom, an alkyl group or an alkoxy group.

[0198] R 4a and R 5aThe number of carbon atoms in the alkyl group is preferably 1 to 30, more preferably 1 to 20, even more 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 those described below in the substituent T.

[0199] R 4a and R 5a The number of carbon atoms in the alkoxy group is preferably 1 to 30, more preferably 1 to 20, even more preferably 1 to 15, particularly preferably 1 to 10, and most preferably 1 to 8. The alkoxy group may be either linear or branched. The alkoxy group may have a substituent. Examples of the substituent include those described below in the substituent T.

[0200] In formula (1a), R 3a With R 4a Can bond with each other to form a ring, R 4a With R 5a Can bond with each other to form a ring, R 5a With R 6a These groups may be bonded to each other to form a ring. The ring formed by these groups bonding to each other is preferably a 5-membered ring or a 6-membered ring. The ring formed by these groups bonding to each other may have a substituent. As a substituent, the group described in the substituent T described below can be given.

[0201] (Substituent T)

[0202] As the substituent T, the following groups can be mentioned.

[0203] Halogen atoms (e.g., chlorine, bromine, and iodine);

[0204] Alkyl groups [straight-chain, branched, or cyclic alkyl groups. Specifically, straight-chain or branched alkyl groups (preferably straight-chain or branched alkyl groups having 1 to 30 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, tert-butyl, n-octyl, eicosyl, 2-chloroethyl, 2-cyanoethyl, and 2-ethylhexyl), cycloalkyl groups (preferably cycloalkyl groups having 3 to 30 carbon atoms, such as cyclohexyl, cyclopentyl, and 4-n-dodecylcyclohexyl), and bicycloalkyl groups (preferably bicycloalkyl groups having 5 to 30 carbon atoms, i.e., monovalent groups obtained by removing one hydrogen atom from a bicycloalkane having 5 to 30 carbon atoms, such as bicyclo[1,2,2]heptane-2-yl and bicyclo[2,2,2]octan-3-yl), and also include tricyclic structures having multiple ring structures. The alkyl groups in the substituents described below (such as the alkyl group of an alkylthio group) also represent alkyl groups of this concept.];

[0205] Alkenyl [straight-chain, branched-chain, or cyclic alkenyl. Specifically, a straight-chain or branched alkenyl (preferably a straight-chain or branched alkenyl having 2 to 30 carbon atoms, for example, vinyl, allyl, isoprenyl, geranyl, and oleyl), a cycloalkenyl (preferably a cycloalkenyl having 3 to 30 carbon atoms. That is, a monovalent group obtained by removing one hydrogen atom from a cycloolefin having 3 to 30 carbon atoms. For example, 2-cyclopenten-1-yl and 2-cyclohexen-1-yl), a bicycloalkenyl (preferably a bicycloalkenyl having 5 to 30 carbon atoms. That is, a monovalent group obtained by removing one hydrogen atom from a bicycloolefin having one double bond. For example, it includes bicyclo[2,2,1]hept-2-en-1-yl and bicyclo[2,2,2]oct-2-en-4-yl).];

[0206] Alkynyl (preferably a linear or branched alkynyl group having 2 to 30 carbon atoms. For example, ethynyl and propargyl);

[0207] Aryl group (preferably an aryl group having 6 to 30 carbon atoms, such as phenyl, p-tolyl, naphthyl, m-chlorophenyl, and o-hexadecanoylaminophenyl);

[0208] Heterocyclic group (preferably a monovalent group obtained by removing one hydrogen atom from a 5-membered or 6-membered aromatic or non-aromatic heterocyclic compound, more preferably a 5-membered or 6-membered aromatic heterocyclic group having 3 to 30 carbon atoms. For example, 2-furyl, 2-thienyl, 2-pyrimidinyl, 2-benzothiazolyl);

[0209] cyano group;

[0210] hydroxyl group;

[0211] Nitro;

[0212] carboxyl;

[0213] an alkoxy group (preferably a linear or branched alkoxy group having 1 to 30 carbon atoms, for example, a methoxy group, an ethoxy group, an isopropoxy group, a tert-butoxy group, an n-octyloxy group, or a 2-methoxyethoxy group);

[0214] an aryloxy group (preferably an aryloxy group having 6 to 30 carbon atoms, for example, a phenoxy group, a 2-methylphenoxy group, a 4-tert-butylphenoxy group, a 3-nitrophenoxy group, and a 2-tetradecanoylaminophenoxy group);

[0215] a heterocyclic oxy group (preferably a heterocyclic oxy group having 2 to 30 carbon atoms, for example, 1-phenyltetrazol-5-oxy and 2-tetrahydropyranyloxy);

[0216] an acyloxy group (preferably a formyloxy group, an alkylcarbonyloxy group having 2 to 30 carbon atoms, or an arylcarbonyloxy group having 6 to 30 carbon atoms. For example, a formyloxy group, an acetoxy group, a pivaloyloxy group, a stearoyloxy group, a benzoyloxy group, or a p-methoxyphenylcarbonyloxy group);

[0217] a carbamoyloxy group (preferably a carbamoyloxy group having 1 to 30 carbon atoms, for example, an N,N-dimethylcarbamoyloxy group, an N,N-diethylcarbamoyloxy group, a morpholinylcarbonyloxy group, an N,N-di-n-octylaminocarbonyloxy group, and an N-n-octylcarbamoyloxy group);

[0218] an alkoxycarbonyloxy group (preferably an alkoxycarbonyloxy group having 2 to 30 carbon atoms, for example, a methoxycarbonyloxy group, an ethoxycarbonyloxy group, a tert-butoxycarbonyloxy group, and an n-octylcarbonyloxy group);

[0219] an aryloxycarbonyloxy group (preferably an aryloxycarbonyloxy group having 7 to 30 carbon atoms, for example, a phenoxycarbonyloxy group, a p-methoxyphenoxycarbonyloxy group, and a p-n-hexadecyloxyphenoxycarbonyloxy group);

[0220] amino group (preferably an amino group, an alkylamino group having 1 to 30 carbon atoms, or an anilino group having 6 to 30 carbon atoms. For example, an amino group, a methylamino group, a dimethylamino group, an anilino group, an N-methyl-anilino group, or a diphenylamino group);

[0221] an acylamino group (preferably a formylamino group, an alkylcarbonylamino group having 2 to 30 carbon atoms, or an arylcarbonylamino group having 6 to 30 carbon atoms. For example, formylamino, acetylamino, trimethylacetylamino, lauroylamino, benzylamino, and 3,4,5-tri-n-octyloxyphenylcarbonylamino);

[0222] an aminocarbonylamino group (preferably an aminocarbonylamino group having 1 to 30 carbon atoms, for example, carbamoylamino, N,N-dimethylaminocarbonylamino, N,N-diethylaminocarbonylamino, and morpholinylcarbonylamino);

[0223] an alkoxycarbonylamino group (preferably an alkoxycarbonylamino group having 2 to 30 carbon atoms, for example, methoxycarbonylamino, ethoxycarbonylamino, tert-butoxycarbonylamino, n-octadecyloxycarbonylamino, and N-methyl-methoxycarbonylamino);

[0224] an aryloxycarbonylamino group (preferably an aryloxycarbonylamino group having 7 to 30 carbon atoms, for example, a phenoxycarbonylamino group, a p-chlorophenoxycarbonylamino group, and a m-n-octyloxyphenoxycarbonylamino group);

[0225] a sulfamoylamino group (preferably a sulfamoylamino group having 0 to 30 carbon atoms, for example, a sulfamoylamino group, an N,N-dimethylaminosulfonylamino group, and an N-octylaminosulfonylamino group);

[0226] an alkylsulfonylamino group or an arylsulfonylamino group (preferably an alkylsulfonylamino group having 1 to 30 carbon atoms or an arylsulfonylamino group having 6 to 30 carbon atoms. For example, a methylsulfonylamino group, a butylsulfonylamino group, a phenylsulfonylamino group, a 2,3,5-trichlorophenylsulfonylamino group, and a p-methylphenylsulfonylamino group);

[0227] thiol;

[0228] an alkylthio group (preferably an alkylthio group having 1 to 30 carbon atoms, such as methylthio, ethylthio, and n-hexadecylthio);

[0229] an arylthio group (preferably an arylthio group having 6 to 30 carbon atoms, for example, a phenylthio group, a p-chlorophenylthio group, and a m-methoxyphenylthio group);

[0230] a heterocyclic thio group (preferably a heterocyclic thio group having 2 to 30 carbon atoms, for example, 2-benzothiazolylthio and 1-phenyltetrazol-5-ylthio);

[0231] a sulfamoyl group (preferably a sulfamoyl group having 0 to 30 carbon atoms, for example, N-ethylsulfamoyl, N-(3-dodecyloxypropyl)sulfamoyl, N,N-dimethylsulfamoyl, N-acetylsulfamoyl, N-benzoylsulfamoyl, and N-(N'-phenylcarbamoyl)sulfamoyl);

[0232] sulfonic acid;

[0233] an alkyl or arylsulfinyl group (preferably an alkylsulfinyl group having 1 to 30 carbon atoms or an arylsulfinyl group having 6 to 30 carbon atoms. For example, methylsulfinyl, ethylsulfinyl, phenylsulfinyl, and p-methylphenylsulfinyl);

[0234] an alkyl or arylsulfonyl group (preferably an alkylsulfonyl group having 1 to 30 carbon atoms or an arylsulfonyl group having 6 to 30 carbon atoms. For example, methylsulfonyl, ethylsulfonyl, phenylsulfonyl, and p-methylphenylsulfonyl);

[0235] acyl group (preferably a formyl group, an alkylcarbonyl group having 2 to 30 carbon atoms, an arylcarbonyl group having 7 to 30 carbon atoms, or a heterocyclic carbonyl group bonded to a carbonyl group via a carbon atom having 4 to 30 carbon atoms. For example, acetyl, pivaloyl, 2-chloroacetyl, stearoyl, benzoyl, p-n-octyloxyphenylcarbonyl, 2-pyridylcarbonyl, and 2-furylcarbonyl);

[0236] an aryloxycarbonyl group (preferably an aryloxycarbonyl group having 7 to 30 carbon atoms, for example, a phenoxycarbonyl group, an o-chlorophenoxycarbonyl group, a m-nitrophenoxycarbonyl group, and a p-tert-butylphenoxycarbonyl group);

[0237] an alkoxycarbonyl group (preferably an alkoxycarbonyl group having 2 to 30 carbon atoms, for example, a methoxycarbonyl group, an ethoxycarbonyl group, a tert-butoxycarbonyl group, and an n-octadecyloxycarbonyl group);

[0238] a carbamoyl group (preferably a carbamoyl group having 1 to 30 carbon atoms, for example, a carbamoyl group, an N-methylcarbamoyl group, an N,N-dimethylcarbamoyl group, an N,N-di-n-octylcarbamoyl group, and an N-(methylsulfonyl)carbamoyl group);

[0239] an aryl or heterocyclic azo group (preferably an arylazo group having 6 to 30 carbon atoms or a heterocyclic azo group having 3 to 30 carbon atoms, for example, a phenylazo group, a p-chlorophenylazo group, and a 5-ethylthio-1,3,4-thiadiazol-2-ylazo group);

[0240] an imide group (preferably an N-succinimide group or an N-phthalimide group);

[0241] A phosphino group (preferably a phosphino group having 2 to 30 carbon atoms, for example, a dimethylphosphino group, a diphenylphosphino group, a methylphenoxyphosphino group)

[0242] a phosphono group (preferably a phosphono group having 2 to 30 carbon atoms, for example, a phosphono group, a dioctyloxyphosphono group, and a diethoxyphosphono group);

[0243] a phosphonooxy group (preferably a phosphonooxy group having 2 to 30 carbon atoms, for example, a diphenoxyphosphonooxy group and a dioctyloxyphosphonooxy group);

[0244] a phosphonylamino group (preferably a phosphonylamino group having 2 to 30 carbon atoms, for example, a dimethoxyphosphonylamino group and a dimethylaminophosphonylamino group);

[0245] Among the groups listed above, for groups having hydrogen atoms, one or more hydrogen atoms may be substituted by the above-mentioned substituent T. Examples of such substituents include alkylcarbonylaminosulfonyl groups, arylcarbonylaminosulfonyl groups, alkylsulfonylaminocarbonyl groups, and arylsulfonylaminocarbonyl groups. Specific examples include methylsulfonylaminocarbonyl groups, p-methylphenylsulfonylaminocarbonyl groups, acetylaminosulfonyl groups, and benzoylaminosulfonyl groups.

[0246] Specific examples of compound (1) include compounds having the following structures: In the structural formula shown below, 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, and Ph is a phenyl group.

[0247] [Chemical Formula 11]

[0248]

[0249] [Chemical Formula 12]

[0250]

[0251] [Chemical Formula 13]

[0252]

[0253] Compound (1) can be preferably used as an ultraviolet absorber. The maximum absorption wavelength of compound (1) is preferably present in the wavelength range of 381 to 420 nm, more preferably in the wavelength range of 381 to 400 nm.

[0254] The molar absorption coefficient ε of compound (1) at a wavelength of 405 nm was calculated according to the following formula: 405 It is preferably 500 or more, more preferably 1000 or more, further preferably 2000 or more, and particularly preferably 3000 or more.

[0255] ε 405 =ε max ×(A 405 / A max )

[0256] ε 405 is the molar absorption coefficient of compound (1) at a wavelength of 405 nm, ε max is the molar absorptivity of compound (1) at the maximum absorption wavelength, A 405 is the absorbance of compound (1) at a wavelength of 405 nm, A max is the absorbance of compound (1) at the maximum absorption wavelength.

[0257] In the optical absorption spectrum of compound (1) measured in ethyl acetate, the absorbance A at a wavelength of 405 nm is 405 and the absorbance A at a wavelength of 430 nm 430 The ratio (A 430 / A 405 ) is preferably less than 0.13, more preferably less than 0.1. The lower limit of the above ratio is not particularly limited and can be set to be greater than 0. The compound having such an absorbance ratio has excellent transmittance in the visible region near the ultraviolet region regardless of the high absorption near the wavelength of 405 nm, and therefore has excellent absorbance of ultraviolet rays on the longer wavelength side and excellent visible transparency. In addition, when the ultraviolet absorption region in the compound is shifted to the longer wavelength side, the transmittance in the visible region (especially, the transmittance in the visible region near the ultraviolet region) also tends to decrease. However, according to the compound (1) of the present invention, there are technically excellent effects such as maintaining the transmittance in the visible region at a high level and having excellent absorbance of ultraviolet rays on the longer wavelength side.

[0258] Compound (1) can be synthesized by referring to the synthesis methods described in Japanese Patent Application Laid-Open No. 2016-081035, Japanese Patent No. 5376885, and the like.

[0259] The content of 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, 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.

[0260] The content of compound (1) is preferably 0.01 to 50 parts by mass per 100 parts by mass of the resin. The lower limit is preferably 0.05 parts by mass or more, 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 even more preferably 20 parts by mass or less.

[0261] The resin composition may contain only one compound (1) or two or more compounds (1). When containing two or more compounds (1), the total amount thereof is preferably within the above range.

[0262] <<Compound represented by formula (2) (Compound (2))>>

[0263] The resin composition of the present invention further preferably contains a compound represented by formula (2) (hereinafter also referred to as compound (2)). According to this embodiment, the storage stability of the resin composition can be further improved.

[0264] [Chemical Formula 14]

[0265]

[0266] In formula (2), R 11 and R 12 Each independently represents an alkyl group, an aryl group or a heterocyclic group,

[0267] R 13 and R 16 each independently represents a hydroxyl 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,

[0268] 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,

[0269] R 15represents 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, an alkylsulfonylamino group, an arylsulfonylamino group, an alkylthio group, or an arylthio group;

[0270] R 11 With R 12 can bond to each other to form a ring;

[0271] R 13 With R 14 can bond to each other to form a ring;

[0272] R 14 With R 15 can bond to each other to form a ring;

[0273] R 15 With R 16 can bond to each other to form a ring;

[0274] Among them, R 13 and R 16 At least one of them is a hydroxyl group.

[0275] R in formula (2) 11 and R 12 The meanings of the alkyl, aryl and heterocyclic groups represented by the formula (1) are the same as those of R 1 and R 2 The alkyl, aryl and heterocyclic groups represented are the same and their preferred ranges are also the same. 11 and R 12 Preferred is an alkyl group or an aryl group.

[0276] R in formula (2) 13 and R 16 Each independently represents a hydroxyl group, an alkoxyl group, an aryloxy group, an acyloxy group, a carbamoyloxy group, an alkoxycarbonyloxy group, an aryloxycarbonyloxy group, a sulfinyloxy group or a sulfonyloxy group, preferably a hydroxyl group, an alkoxyl group or an acyloxy group, more preferably a hydroxyl group or an alkoxyl group, and further preferably a hydroxyl group. 13 and R 16 At least one of them is a hydroxyl group.

[0277] R 13 and R 16 The number of carbon atoms in the alkoxy group is preferably 1 to 30, more preferably 1 to 20, even more preferably 1 to 15, particularly preferably 1 to 10, and most preferably 1 to 8. The alkoxy group may be straight-chain or branched. The alkoxy group may have a substituent. Examples of the substituent include those described above for the substituent T.

[0278] R 13 and R 16The number of carbon atoms in the aryloxy group 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 aryloxy group may have a substituent. Examples of the substituent include those described above for the substituent T.

[0279] R 13 and R 16 The number of carbon atoms in the acyloxy group 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 those described in the substituent T below.

[0280] R 13 and R 16 The number of carbon atoms in the carbamoyloxy group is preferably 2 to 30, more preferably 2 to 20, even more preferably 2 to 15, particularly preferably 2 to 10, and most preferably 2 to 8. The carbamoyloxy group may be either linear or branched. The carbamoyloxy group may have a substituent. Examples of the substituent include those described above for the substituent T.

[0281] R 13 and R 16 The number of carbon atoms in the alkoxycarbonyloxy group is preferably 2 to 30, more preferably 2 to 20, even more 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 those described above for the substituent T.

[0282] R 13 and R 16 The number of carbon atoms in the aryloxycarbonyloxy group is preferably 7 to 40, more preferably 7 to 30, even more preferably 7 to 20, particularly preferably 7 to 15, and most preferably 7 to 12. The aryloxycarbonyloxy group may have a substituent. Examples of the substituent include those described above for the substituent T.

[0283] R 13 and R 16 The number of carbon atoms in the sulfinyloxy group 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 those described above for the substituent T.

[0284] R 13 and R 16 The number of carbon atoms in the sulfonyloxy group 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 those described above for the substituent T.

[0285] R in formula (2) 14 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, and R 15 represents 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, an alkylsulfonylamino group, an arylsulfonylamino group, an alkylthio group, or an arylthio group. 14 and R 15 The detailed meanings of these groups are the same as those of R in formula (1). 4 and R 5 The preferred ranges are also the same.

[0286] Preferred R 14 is an alkyl group, an aryl group, an alkoxy group or an aryloxy group, R 15 is a hydrogen atom, an alkyl group, an aryl group, an alkoxy group or an aryloxy group, more preferably R 14 is an alkyl group or an alkoxy group, R 15 is a hydrogen atom, an alkyl group or an alkoxy group.

[0287] As one of the preferred embodiments, R 14 is an alkyl, aryl, alkoxy or aryloxy group and R 15 In this embodiment, R 14 is an alkyl group or an alkoxy group, R 15 A hydrogen atom.

[0288] Furthermore, as another preferred embodiment, R 14 and R 15 In this embodiment, R 14 and R 15 are independently alkyl or alkoxy, more preferably R 14 and R 15 Both are alkyl or R 14 and R 15 Both are alkoxy groups.

[0289] Furthermore, as another preferred embodiment, R 14 With R 15 They can be bonded to each other to form a ring.

[0290] Specific examples of compound (2) include compounds having the following structures: In the structural formula shown below, 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, and Ph is a phenyl group.

[0291] [Chemical Formula 15]

[0292]

[0293] [Chemical Formula 16]

[0294]

[0295] [Chemical Formula 17]

[0296]

[0297] [Chemical Formula 18]

[0298]

[0299] Compound (2) can be synthesized according to the method described in Japanese Patent No. 5376885 and International Publication No. 2019 / 142539.

[0300] Compound (2) is preferably used as an ultraviolet absorber. The maximum absorption wavelength of compound (2) is preferably present in the wavelength range of 381 to 420 nm, more preferably in the wavelength range of 381 to 400 nm.

[0301] When the resin composition contains compound (2), the content of compound (2) is preferably 5 parts by mass or less, more preferably 3 parts by mass or less, and even more preferably 1 part by mass or less, based on 100 parts by mass of compound (1). The lower limit is preferably 0.1 parts by mass or more.

[0302] Furthermore, the total content of compound (1) and 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, 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.

[0303] The total content of compound (1) and compound (2) is preferably 0.01 to 50 parts by mass per 100 parts by mass of the resin. The lower limit is preferably 0.05 parts by mass or more, 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 even more preferably 20 parts by mass or less.

[0304] The resin composition may contain one compound (2) or two or more compounds (2). When containing two or more compounds (2), the total amount thereof is preferably within the above range.

[0305] Furthermore, it is also preferred that the resin composition does not substantially contain compound (2). According to this embodiment, it is easy to obtain more excellent light resistance. In addition, in this specification, the resin composition does not substantially contain compound (2) means that the content of compound (2) in the total solid content of the resin composition is 0.001% by mass or less, preferably 0.0001% by mass or less, and more preferably does not contain it.

[0306] <<Other UV absorbers>>

[0307] The resin composition of the present invention may contain other ultraviolet absorbers (hereinafter also referred to as other ultraviolet absorbers) in addition to the compound (1). According to this embodiment, a cured product that blocks light of a wide range of wavelengths in the ultraviolet region can be formed.

[0308] The maximum absorption wavelength of the other ultraviolet absorber preferably exists in the wavelength range of 390 nm or less, and more preferably exists in the wavelength range of 380 nm or less.

[0309] Other UV absorbers 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 preferred, and benzotriazole-based UV absorbers and triazine-based UV absorbers are more preferred. Specific examples of benzotriazole-based UV absorbers, benzophenone-based UV absorbers, salicylic acid-based UV absorbers, acrylate-based UV absorbers, and triazine-based UV absorbers include the compounds described in paragraphs 0065 to 0070 of Japanese Patent Application Publication No. 2009-263616 and the compounds described in paragraph 0065 of International Publication No. 2017 / 122503, the contents of which are incorporated herein. Furthermore, compounds with the following structures can also be preferably used as other UV absorbers.

[0310] [Chemical Formula 19]

[0311]

[0312] When the resin composition contains another ultraviolet absorber, the content of the other ultraviolet 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, 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.

[0313] Furthermore, the total content of compound (1), 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, 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.

[0314] The resin composition may contain only one other ultraviolet absorber or two or more. When containing two or more other ultraviolet absorbers, the total amount thereof is preferably within the above range.

[0315] <<Resin>>

[0316] The resin composition of the present invention comprises a resin. Examples of the resin include (meth) acrylic resins, polyester resins, polycarbonate resins, vinyl polymers [e.g., polydiene resins, polyolefin resins, polystyrene resins, polyvinyl ether resins, polyvinyl alcohol resins, polyvinyl ketone resins, polyvinyl fluoride resins, and polyvinyl bromide resins], polysulfide ether resins, polyphenylene resins, polyurethane resins, polythiocarbamate resins, polysulfonate resins, nitroso polymer resins, polysiloxane resins, polysulfide resins, polythioester resins, polysulfone resins, polysulfoneamide resins, polyamide resins, polyimine resins, polyurea resins, polyphosphazene resins, polysilane resins, polysilazane resins, polyfuran resins, and the like. Resin, polybenzoxazole resin, polyoxadiazole resin, polybenzothiazine phenothiazine resin, polybenzothiazole resin, polypyrazinoquinoxaline resin, polypyromellitimide resin, polyquinoxaline resin, polybenzimidazole resin, polyoxyisoindoline resin, polydioxyisoindoline resin, polytriazine resin, polypyridazine resin, polypiperazine resin, polypyridine resin, polypiperidine resin, polytriazole resin, polypyrazole resin, polypyrrolidine resin, polycarborane resin, polyoxybicyclononane resin, polydibenzofuran resin, polyphthalolactone resin, polyacetal resin, polyimide resin, olefin resin, cyclic olefin resin, epoxy resin, cellulose acylate resin etc.Can suitably select according to purposes and purpose.About these details, can refer to the record in paragraph 0075~0097 of Japanese Patent Laid-Open No. 2009-263616 gazette, this content is incorporated in this specification sheets.

[0317] Furthermore, a resin having a polymerizable group can also be used as the resin. Commercially available products of resins having a polymerizable group include the Dianal BR series (polymethyl methacrylate (PMMA), such as Dianal BR-80, BR-83, and BR-87; Mitsubishi Chemical Corporation); Photomer 6173 (COOH-containing urethane acrylic oligomer, Diamond Shamrock Co., Ltd.); Viscoat R-264 and KS Resist 106 (both from OSAKA ORGANIC CHEMICAL INDUSTRY LTD.); CYCLOMER P series (such as ACA230AA) and PLACCEL CF200 series (both from Daicel Corporation); Ebecryl 3800 (Daicel UCB Co., Ltd.); and Acrycure-RD-F8 (NIPPONSHOKUBAI CO., LTD.).

[0318] The resin is preferably at least one selected from the group consisting of (meth)acrylic resins, polystyrene resins, polyester resins, polyurethane resins, polythiocarbamate resins, polyimide resins, epoxy resins, polycarbonate resins and cellulose acylate resins, and more preferably at least one selected from the group consisting of (meth)acrylic resins, polystyrene resins, polyester resins, polyurethane resins, polythiocarbamate resins, polycarbonate resins and cellulose acylate resins, because it is easy to obtain a cured product having good compatibility with compound (1) and suppressed surface unevenness.

[0319] As the cellulose acylate resin, the cellulose acylate described in paragraphs 0016 to 0021 of Japanese Patent Application Laid-Open No. 2012-215689 can be preferably used. As the polyester resin, commercially available products such as the Byron series (e.g., Byron 500) manufactured by Toyobo Co., Ltd. can also be used. As commercially available (meth)acrylic resins, the SK Dyne series (e.g., SK Dyne-SF2147) manufactured by Soken Chemical & Engineering Co., Ltd. can also be used.

[0320] As the polystyrene resin, the polystyrene resin described below is preferably used. Here, the styrene resin refers to a resin in which the monomer units constituting the resin have the highest ratio of monomer units derived from styrene monomers. For example, in the case of a resin composed of two components, it refers to a resin comprising 50% by mass or more of monomer units derived from styrene monomers. Here, the styrene monomer refers to a monomer having a styrene skeleton in its structure. The styrene resin preferably comprises 70% by mass or more of monomer units derived from styrene monomers, more preferably 85% by mass or more.

[0321] Specific examples of styrene-based monomers include homopolymers of styrene or its derivatives, and binary or higher copolymers of styrene or its derivatives with other copolymerizable monomers. Styrene derivatives herein are compounds in which other groups are bonded to styrene. Examples include alkyl styrenes such as o-methylstyrene, m-methylstyrene, p-methylstyrene, 2,4-dimethylstyrene, o-ethylstyrene, and p-ethylstyrene; and substituted styrenes such as hydroxystyrene, tert-butoxystyrene, vinylbenzoic acid, o-chlorostyrene, and p-chlorostyrene, in which hydroxyl groups, alkoxy groups, carboxyl groups, halogen groups, or the like are introduced into the benzene nucleus of styrene.

[0322] Furthermore, styrene-based resins include those obtained by copolymerizing other monomer components with styrene-based monomer components. Examples of copolymerizable monomers include methacrylic acid alkyl esters such as methyl methacrylate, cyclohexyl methacrylate, methylphenyl methacrylate, and isopropyl methacrylate; unsaturated carboxylic acid alkyl ester monomers such as alkyl acrylates such as methyl acrylate, ethyl acrylate, butyl acrylate, 2-ethylhexyl acrylate, and cyclohexyl acrylate; unsaturated carboxylic acid monomers such as methacrylic acid, acrylic acid, itaconic acid, maleic acid, fumaric acid, and cinnamic acid; unsaturated dicarboxylic acid anhydride monomers such as maleic anhydride, itaconic acid, ethylmaleic acid, methylitaconic acid, and chloromaleic acid; unsaturated nitrile monomers such as acrylonitrile and methacrylonitrile; and conjugated dienes such as 1,3-butadiene, 2-methyl-1,3-butadiene (isoprene), 2,3-dimethyl-1,3-butadiene, 1,3-pentadiene, and 1,3-hexadiene. Two or more of these monomers can also be copolymerized. Commercially available styrene resins may also be used, and examples of commercially available products include AS-70 (acrylonitrile / styrene copolymer resin, manufactured by Nippon Steel Chemical & Material Co., Ltd.) and SMA2000P (styrene / maleic acid copolymer, manufactured by Kawahara Petrochemical Co., Ltd.).

[0323] As the styrene-based resin, multiple types having different compositions, molecular weights, etc. can be used simultaneously.

[0324] Styrene resins can be obtained by known anionic, bulk, suspension, emulsification, or solution polymerization methods. Furthermore, in polystyrene resins, the unsaturated double bonds of the benzene rings of the conjugated dienes and styrene monomers may be hydrogenated. The hydrogenation rate can be measured by nuclear magnetic resonance (NMR).

[0325] The weight average molecular weight (Mw) of the resin is preferably 3,000 to 2,000,000. The upper limit is preferably 1,000,000 or less, more preferably 500,000 or less. The lower limit is preferably 4,000 or more, more preferably 5,000 or more.

[0326] The total light transmittance of the resin is preferably 80% or more, more preferably 85% or more, and even more preferably 90% or more. In this specification, the total light transmittance of the resin is a value measured in accordance with the contents described in "Experimental Chemistry Lecture 29: Polymer Materials and Media, 4th Edition," edited by the Chemical Society of Japan (Maruzen, 1992), pages 225-232.

[0327] The resin content in the total solids 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 one resin or two or more resins. When containing two or more resins, the total amount of these resins is preferably within the above range.

[0328] <<Curing compound>>

[0329] The resin composition may contain a curable compound. Examples of the curable compound include polymerizable compounds and compounds having an -O-Si-O- structure.

[0330] As the polymerizable compound, a compound capable of polymerizing and curing by imparting energy can be used without limitation. As the polymerizable compound, a compound having a group containing an ethylenically unsaturated bond, a compound having an epoxy group, a compound having a hydroxymethyl group, etc. can be enumerated, preferably a compound having a group containing an ethylenically unsaturated bond, more preferably a compound having two or more groups containing an ethylenically unsaturated bond. As the group containing an ethylenically unsaturated bond, vinyl, allyl, (meth) acryloyl, etc. can be enumerated.

[0331] The polymerizable compound may be, for example, a monomer, a prepolymer (ie, a dimer, a trimer, or an oligomer), a mixture thereof, or a (co)polymer of a compound selected from monomers and prepolymers.

[0332] Examples of the compound having an ethylenically unsaturated bond-containing group used as a polymerizable compound include unsaturated carboxylic acids (e.g., acrylic acid, methacrylic acid, itaconic acid, crotonic acid, isocrotonic acid, maleic acid, etc.), esters of unsaturated carboxylic acids, amides of unsaturated carboxylic acids, and (co)polymers of unsaturated carboxylic acids or their esters or amides. Among these, esters of unsaturated carboxylic acids and aliphatic polyols, amides of unsaturated carboxylic acids and aliphatic polyamines, and homopolymers or copolymers thereof are preferred.

[0333] Examples of compounds having a group containing an ethylenically unsaturated bond that can be used as polymerizable compounds include addition reaction products of unsaturated carboxylic acid esters or unsaturated carboxylic acid amides having a nucleophilic substituent (e.g., hydroxyl, amino, mercapto, etc.) with monofunctional or polyfunctional isocyanate compounds or epoxy compounds; dehydration condensation reaction products of unsaturated carboxylic acid esters or unsaturated carboxylic acid amides having a nucleophilic substituent (e.g., isocyanate, epoxy, etc.) with monofunctional or polyfunctional alcohols, amines, or thiols; and substitution reaction products of unsaturated carboxylic acid esters or unsaturated carboxylic acid amides having a leaving substituent (e.g., halogen, tosyloxy, etc.) with monofunctional or polyfunctional alcohols, amines, or thiols. Furthermore, examples include compounds obtained by substituting the above-mentioned unsaturated carboxylic acids with unsaturated phosphonic acids, styrenes, vinyl ethers, etc.

[0334] Furthermore, among the compounds having a group containing an ethylenically unsaturated bond used as the polymerizable compound, multiple compounds having different functional groups or multiple compounds having different types of polymerizable groups (e.g., acrylates, methacrylates, styrene-based compounds, vinyl ether-based compounds, etc.) can be used simultaneously.

[0335] Commercially available compounds having a group containing an ethylenically unsaturated bond include polyfunctional (meth)acrylate compounds such as the KYARAD (registered trademark) series (e.g., PET-30, TPA-330, etc.) of Nippon Kayaku Co., Ltd., POLYVEST (registered trademark) 110M of EVONIK, and the NK Ester series (e.g., NK Ester A-9300, etc.) of SHIN-NAKAMURA CHEMICAL Co., Ltd.

[0336] As compounds having epoxy groups used as polymerizable compounds (hereinafter also referred to as epoxy compounds), monofunctional or polyfunctional glycidyl ether compounds, polyfunctional aliphatic glycidyl ether compounds, etc. can be mentioned. In addition, as epoxy compounds, compounds having alicyclic epoxy groups can also be used. As epoxy compounds, compounds having one epoxy group in one molecule can be mentioned. 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 can be set to 10 or less, or 5 or less, for example. The lower limit of the epoxy group is preferably 2 or more. Specific examples of monofunctional epoxy compounds include 2-ethylhexyl glycidyl ether, etc. Specific examples of polyfunctional epoxy compounds include 1,4-cyclohexanedimethanol diglycidyl ether, 3',4'-epoxycyclohexylmethyl 3,4-epoxycyclohexanecarboxylate, etc.

[0337] The epoxy compound may be 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 100000. The upper limit of the weight average molecular weight is preferably 10000 or less, more preferably 5000 or less, and further preferably 3000 or less. Commercially available products of epoxy compounds include multifunctional epoxy compounds such as CELLOXIDE 2021P (trade name, 3',4'-epoxycyclohexylmethyl 3,4-epoxycyclohexanecarboxylate) manufactured by Daicel Corporation and RIKARESIN DME-100 (trade name, containing 1,4-cyclohexanedimethanol diglycidyl ether as a main component) manufactured by New Japan Chemical Co., Ltd.

[0338] Examples of compounds having a methylol group (hereinafter also referred to as a methylol compound) include compounds in which a methylol group is bonded to a nitrogen atom or a carbon atom forming an aromatic ring. Examples of compounds in which a methylol group is bonded to a nitrogen atom include alkoxymethylated melamine, methylolated melamine, alkoxymethylated benzoguanamine, methylolated benzoguanamine, alkoxymethylated glycoluril, methylolated glycoluril, alkoxymethylated urea, methylolated urea, and trimethylolpropane-modified toluene diisocyanate.

[0339] As the polymerizable compound, a high molecular weight compound can also be used. Examples of the high molecular weight polymerizable compound include (meth)acrylic resins, ester resins, urethane resins, and fluorine-based resins. Examples of commercially available products include the Dianal BR series (polymethyl methacrylate (PMMA), such as Dianal BR-80, BR-83, and BR-87; Mitsubishi Chemical Corporation); Photomer 6173 (COOH-containing urethane acrylic oligomer; Diamond Shamrock Co., Ltd.); Viscoat R-264 and KS Resist 106 (both from OSAKA ORGANIC CHEMICAL INDUSTRY LTD.); CYCLOMER P series (such as ACA230AA) and PLACCEL CF200 series (both from Daicel Corporation); Ebecryl 3800 (Daicel UCB Co., Ltd.); and Acrycure-RD-F8 (NIPPONSHOKUBAI CO., LTD.). Furthermore, high-molecular-weight polymerizable compounds also qualify as components of resins.

[0340] From the perspective of improving the strength after curing, the polymerizable polymer compound is preferably a compound capable of forming a crosslinked structure. The formation of the crosslinked structure is not particularly limited, and examples thereof include a method of simultaneously using a polymerizable polymer compound and a multifunctional (meth)acrylate monomer; a method of simultaneously using a polymerizable polymer compound having a reactive group introduced therein and a crosslinking agent having a crosslinking group capable of reacting with the reactive group; and the like.

[0341] Examples of reactive groups include groups containing active hydrogen, specifically groups selected from hydroxyl groups, primary amino groups, and secondary amino groups. Examples of polymerizable compounds into which reactive groups are introduced include (meth)acrylic resins containing structural units derived from (meth)acrylate monomers and having two or more active hydrogen-containing groups.

[0342] Examples of crosslinking agents include polyisocyanates having two or more isocyanate groups as crosslinkable groups. Examples of commercially available products include AD-TMP and A-9550 (both trade names) from SHIN-NAKAMURA CHEMICAL Co., LTD. Among these, it is preferred to use a (meth)acrylic resin having two or more (preferably three or more) active hydrogen-containing groups and a crosslinking agent having two or more isocyanate groups (preferably a polyisocyanate having two or more isocyanate groups, more preferably a polyisocyanate having three or more isocyanate groups) simultaneously. Thus, a crosslinked structure can be formed by reacting the active hydrogen-containing groups with the isocyanate groups.

[0343] The compound having an -O-Si-O- structure is preferably a hydrolyzable silicon compound, more preferably a hydrolyzable alkoxysilane, and still more preferably a trifunctional or tetrafunctional alkoxysilane. Specific examples of the compound having an -O-Si-O- structure include tetramethoxysilane, tetraethoxysilane, tetra-n-propoxysilane, tetra-isopropoxysilane, tetra-n-butoxysilane, methyltrimethoxysilane, methyltriethoxysilane, ethyltrimethoxysilane, ethyltriethoxysilane, n-propyltrimethoxysilane, n-propyltriethoxysilane, phenyltrimethoxysilane, phenyltriethoxysilane, γ-glycidoxypropyltrimethoxysilane, γ-glycidoxypropyltriethoxysilane, γ-glycidoxypropylmethyldimethoxysilane, γ-methacryloxypropylmethyldiethoxysilane, γ-methacryloxypropyltrimethoxysilane, γ-methacryloxypropyltriethoxysilane, γ-methacryloxypropyltriethoxysilane, Methyldimethoxysilane, vinyltrimethoxysilane, vinyltriethoxysilane, 3,4-epoxycyclohexylethyltrimethoxysilane, 3,4-epoxycyclohexylethyltriethoxysilane, tris-(trimethoxysilylpropyl)isocyanurate, 4-trimethoxysilylstyrene, 3,3,3-trifluoropropyltrimethoxysilane, dimethyldimethoxysilane, dimethyldiethoxysilane, diethyldimethoxysilane, diethyldiethoxysilane, di-n-propyldimethoxysilane, di-n-propyldiethoxysilane, diphenyldimethoxysilane, divinyldiethoxysilane, bis(triethoxysilylpropyl)tetrasulfide, 3-(trimethoxysilyl)propyl isocyanate, 3-(triethoxysilyl)propyl isocyanate, etc.

[0344] When the resin composition contains a curable compound, 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, more preferably 5% by mass or more. The upper limit is preferably 80% by mass or less, more preferably 70% by mass or less. The resin composition may contain only one curable compound or more than two. When containing two or more curable compounds, the total amount of these is preferably within the above range.

[0345] <<Polymerization initiator>>

[0346] The resin composition may contain a polymerization initiator. In particular, when a polymerizable compound is used as the curable compound, it is preferably contained in a polymerization initiator. By including a polymerization initiator in the resin composition, the polymerization reaction of the polymerizable compound can be started well. The polymerization initiator can be a compound that can generate the starting material required for the polymerization reaction by imparting energy. As the polymerization initiator, for example, it can be appropriately selected from photopolymerization initiators and thermal polymerization initiators, and is preferably a photopolymerization initiator.

[0347] The photopolymerization initiator is preferably a compound having light absorption in the ultraviolet region to the visible region (eg, 280 nm to 400 nm), and examples thereof include photoradical initiators that generate active radicals to initiate photoradical polymerization and cationic initiators that initiate photocationic polymerization.

[0348] As the photopolymerization initiator, there can be mentioned halogenated hydrocarbon derivatives (for example, compounds having a triazine skeleton, compounds having an oxadiazole skeleton, etc.), acylphosphine compounds, hexaarylbisimidazoles, oxime compounds, organic peroxides, sulfur compounds, ketone compounds, aromatic onium salts, aminoacetophenone compounds, hydroxyacetophenone compounds, etc. As the aminoacetophenone compound, there can be mentioned the aminoacetophenone-based initiators described in Japanese Patent Application Laid-Open No. 2009-191179 and Japanese Patent Application Laid-Open No. 10-291969. As the acylphosphine compound, there can be mentioned the acylphosphine-based initiators described in Japanese Patent Application No. 4225898. The photopolymerization initiator can be a synthetic product or a commercially available product sold on the market.

[0349] Examples of commercially available hydroxyacetophenone compounds include Omnirad 184, Omnirad 1173, Omnirad 2959, and Omnirad 127 (all manufactured by IGM Resins BV). Examples of commercially available aminoacetophenone compounds include Omnirad 907, Omnirad 369, Omnirad 369E, and Omnirad 379EG (all manufactured by IGM Resins BV). Examples of commercially available acylphosphine compounds include Omnirad 819 and Omnirad TPO (all manufactured by IGM Resins BV).

[0350] As a photopolymerization initiator, an oxime compound is preferably used. Specific examples of oxime compounds include compounds described in Japanese Patent Application Laid-Open No. 2001-233842, compounds described in Japanese Patent Application Laid-Open No. 2000-080068, compounds described in Japanese Patent Application Laid-Open No. 2006-342166, and compounds described in paragraphs 0073 to 0075 of Japanese Patent Application Laid-Open No. 2016-006475. Among oxime compounds, oxime ester compounds are preferred. Commercially available products of oxime compounds include Irgacure OXE01, Irgacure OXE02 (manufactured by BASF), and Irgacure OXE03 (manufactured by BASF).

[0351] Examples of cationic polymerization initiators include initiators for initiating photocationic polymerization, photodecolorizers for pigment compounds, photochromic agents, known acid generators for microresists, and mixtures thereof. Specifically, examples of cationic polymerization initiators include onium compounds, organic halogen compounds, and disulfone compounds.

[0352] Examples of the onium compound include diazonium salts, ammonium salts, iminium salts, phosphonium salts, iodonium salts, sulfonium salts, arsonium salts, and selenium salts. Detailed descriptions of the onium compound include the compounds described in paragraphs 0058 to 0059 of JP-A-2002-029162.

[0353] When the resin composition contains a polymerization initiator, 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, more preferably 0.4% by mass or more. The upper limit is preferably 15% by mass or less, more preferably 10% by mass or less. The resin composition may contain only one polymerization initiator or two or more. When containing two or more polymerization initiators, the total amount of these is preferably within the above range.

[0354] <<Acid Generator>>

[0355] The resin composition of the present invention may contain an acid generator. In particular, when a cationic polymerizable compound such as a compound having an epoxy group is used as the polymerizable compound, it is preferable to contain an acid generator. The acid generator may be a photoacid generator or a thermal acid generator. In this specification, an acid generator refers to a compound that generates an acid by applying energy such as heat or light. Furthermore, a thermal acid generator refers to a compound that generates an acid by thermal decomposition. Furthermore, a photoacid generator refers to a compound that generates an acid by light irradiation. Examples of acid generators, specific compounds, and preferred examples include the compounds described in paragraphs 0066 to 0122 of Japanese Patent Application Laid-Open No. 2008-013646, which can be applied to the present invention.

[0356] Thermal acid generators include compounds having a thermal decomposition temperature preferably within the range of 130°C to 250°C, more preferably within the range of 150°C to 220°C. Examples of thermal acid generators include compounds that generate low-nucleophilic acids such as sulfonic acid, carboxylic acid, and disulfonylimide upon heating. The acid generated from the thermal acid generator preferably has a pKa of 4 or less, more preferably 3 or less, and even more preferably 2 or less. Examples include sulfonic acid, alkyl carboxylic acids substituted with electron-withdrawing groups, aryl carboxylic acids, and disulfonylimide. Examples of electron-withdrawing groups include halogen atoms such as fluorine atoms, halogenated alkyl groups such as trifluoromethyl, nitro groups, and cyano groups.

[0357] Examples of photoacid generators include onium salt compounds such as diazonium salts, phosphonium salts, sulfonium salts, and iodonium salts, which generate an acid by decomposition upon light irradiation; and sulfonate compounds such as imide sulfonates, oxime sulfonates, diazonium disulfones, disulfones, and o-nitrobenzyl sulfonates. Commercially available photoacid generators include WPAG-469 (manufactured by FUJIFILM Wako Pure Chemical Corporation.), CPI-100P (manufactured by San-Apro Ltd.), and Irgacure 290 (manufactured by BASF Japan Ltd.). Furthermore, 2-isopropylthioxanthone and the like can also be used as photoacid generators.

[0358] When the resin composition contains an acid 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, and even more preferably 0.1 to 20 parts by mass, relative to 100 parts by mass of the curable compound. The resin composition may contain only one acid generator or two or more. When containing two or more acid generator media, the total amount of these media is preferably within the above range.

[0359] Catalyst

[0360] The resin composition can contain a catalyst. In particular, when a compound having an -O-Si-O- structure is used as a curable compound, it is preferred to contain a catalyst. According to this embodiment, the sol-gel reaction is promoted and a stronger film is easily obtained. Examples of 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. When the resin composition contains a catalyst, 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 20 parts by mass relative to 100 parts by mass of the curable compound. The resin composition may contain only one catalyst or two or more. When two or more catalysts are included, the total amount of these is preferably within the above range.

[0361] <<Silane coupling agent>>

[0362] The resin composition of the present invention can contain a silane coupling agent. According to this method, the adhesion between the obtained film and the support can be further improved. In the present invention, a silane coupling agent refers to a silane compound having a hydrolyzable group and a functional group other than the hydrolyzable group. Furthermore, a hydrolyzable group refers to a substituent that is directly bonded to a silicon atom and can generate a siloxane bond through at least one of a hydrolysis reaction and a condensation reaction. As a hydrolyzable group, for example, a halogen atom, an alkoxy group, an acyloxy group, etc. can be mentioned, preferably an alkoxy group. That is, the silane coupling agent is preferably a compound having an alkoxysilyl group. Furthermore, as a functional group other than the hydrolyzable group, for example, a vinyl group, a (meth) allyl group, a (meth) acryloyl group, a thiol group, an epoxy group, an oxetanyl group, an amino group, a urea group, a thioether group, an isocyanate group, a phenyl group, etc. can be mentioned, preferably an amino group, a (meth) acryloyl group and an epoxy group. As specific examples of silane coupling agents, compounds described in paragraphs 0018 to 0036 of Japanese Patent Application Publication No. 2009-288703 and compounds described in paragraphs 0056 to 0066 of Japanese Patent Application Publication No. 2009-242604 are included in this specification. Commercially available silane coupling agents include A-50 (organosilane) from Soken Chemical & Engineering Co., Ltd. The content of the silane coupling agent in the total solids content of the resin composition is preferably 0.1 to 5% by mass. The upper limit is preferably 3% by mass or less, more preferably 2% by mass or less. The lower limit is preferably 0.5% by mass or more, more preferably 1% by mass or more. The silane coupling agent may be only one or more. In the case of two or more, the total amount is preferably within the above range.

[0363] <<Surfactants>>

[0364] The resin composition of the present invention can contain a surfactant. As a surfactant, various surfactants such as fluorine-based surfactants, nonionic surfactants, cationic surfactants, anionic surfactants, silicone surfactants, etc. can be used. The surfactant is preferably a fluorine-based surfactant. By containing a fluorine-based surfactant in the resin composition, the liquid properties (especially fluidity) are further improved, and a film with less uneven thickness can also be formed. 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. Fluorine-based surfactants with a fluorine content within this range are effective in terms of uniformity of thickness of the coating film and liquid saving, and also have good solubility in the resin composition.

[0365] Examples of commercially available fluorochemical surfactants include MEGAFAC 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, F-561, F-565, F-563, F-568, F-575, F-780, EXP, MFS-330, R-01, R-40, R-40-LM, R-41, R-41-LM, RS-43, TF-1956, RS-90, R-94, RS-72-K, DS-21 (all DIC Corporation), FLUORAD FC430, FC431, FC171 (all manufactured by Sumitomo 3M Limited), Surflon S-382, SC-101, SC-103, SC-104, SC-105, SC-1068, SC-381, SC-383, S-393, KH-40 (all manufactured by AGC Inc.), PolyFox PF636, PF656, PF6320, PF6520, PF7002 (all manufactured by OMNOVA Solutions Inc.), Footgent 208G, 215M, 245F, 601AD, 601ADH2, 602A, 610FM, 710FL, 710FM, 710FS, FTX-218 (all manufactured by NEOS Company Limited), etc. Furthermore, the following compounds are also exemplified as the fluorine-based surfactant used in the present invention.

[0366] [Chemical Formula 20]

[0367]

[0368] Examples of the nonionic surfactant include glycerol, trimethylolpropane, trimethylolethane, and ethoxylates and propoxylates thereof (e.g., glycerol propoxylate, glycerol ethoxylate, etc.), polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, polyoxyethylene oleyl ether, polyoxyethylene octylphenyl ether, polyoxyethylene nonylphenyl ether, polyethylene glycol dilaurate, polyethylene glycol distearate, sorbitan fatty acid esters, Pluronic L10, L31, L61, L62, 10R5, 17R2, and 25R2 (manufactured by BASF), Tetronic 304, 701, 704, 901, 904, and 150R1 (manufactured by BASF), Solsperse 20000 (manufactured by Japan Lubrizol Corporation), NCW-101, NCW-1001, and NCW-1002 (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.). Corporation), Pionin D-6112, D-6112-W, D-6315 (manufactured by Takemoto Oil & Fat Co., Ltd.), Olfin E1010, Surfynol 104, 400, 440 (manufactured by Nissin Chemical Industry Co., Ltd.), and the like.

[0369] Examples of the silicone surfactant include Toray Silicone DC3PA, Toray Silicone SH7PA, Toray Silicone DC11PA, Toray Silicone SH21PA, Toray Silicone SH28PA, Toray Silicone SH29PA, Toray Silicone SH30PA, and Toray Silicone SH8400 (all manufactured by Dow Corning Toray Co., Ltd.), TSF-4440, TSF-4300, TSF-4445, TSF-4460, and TSF-4452 (all manufactured by Momentive Performance Materials Inc.), KP-341, KF-6001, and KF-6002 (all manufactured by Shin-Etsu Chemical Co., Ltd.), BYK-307, BYK-323, BYK-330, BYK-3760, and BYK-UV3510 (all manufactured by BYK Chemie Co., Ltd.) etc.

[0370] In recent years, it has become clear that the toxicity and bioaccumulation of compounds with straight-chain perfluoroalkyl groups having more than 7 carbon atoms are high, and therefore the use of perfluorooctane acid and perfluorooctane sulfonic acid has been gradually restricted. Therefore, it is preferred to use a surfactant using an alternative material of perfluorooctane acid and perfluorooctane sulfonic acid. In addition, as a fluorine-based surfactant, from the viewpoint of improving environmental suitability, it is preferred to use a surfactant derived from an alternative material of a compound with straight-chain perfluoroalkyl groups having more than 7 carbon atoms, such as perfluorooctane acid (PFOA) and perfluorooctane sulfonic acid (PFOS).

[0371] The content of the surfactant in the total solid content of the resin composition is preferably 0.001% to 5.0% by mass, more preferably 0.005% to 3.0% by mass. The surfactant may be a single surfactant or two or more surfactants. In the case of two or more surfactants, the total amount is preferably within the above range.

[0372] <<Solvent>>

[0373] The resin composition preferably further comprises a solvent. The solvent is not particularly limited, and examples thereof include water and organic solvents. Examples of the organic solvent include alcohol solvents, ester solvents, ketone solvents, amide solvents, ether solvents, hydrocarbon solvents, and halogen solvents. Specific examples of organic solvents 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, glycerol, 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, dimethylacetamide, ethyl acetate, chloroform, dichloromethane, methyl acetate, etc. The solvent may be only one kind or two or more kinds may be used simultaneously. The content of the solvent is preferably 10 to 90% by mass relative to the total amount of the resin composition.

[0374] <<Other additives>>

[0375] The resin composition may contain any additives such as an antioxidant, a light stabilizer, a processing stabilizer, an anti-aging agent, a compatibilizer, etc. as needed. By appropriately containing these components, various properties of the obtained cured product can be appropriately adjusted.

[0376] <<Application>>

[0377] The resin composition of the present invention can be preferably used in applications that are likely to be exposed to light, including sunlight or ultraviolet light. Specific examples include coating materials or films for window panes of buildings, facilities, and transportation equipment; interior and exterior decorative materials and coatings for buildings, facilities, and transportation equipment; components for ultraviolet-emitting light sources such as fluorescent lamps and mercury lamps; components for solar cells, precision machinery, electronic and electrical equipment, and display devices; containers or packaging materials for food, chemicals, and pharmaceuticals; agricultural and industrial sheets; fiber products and fibers for clothing such as sportswear, stockings, and hats; lenses such as plastic lenses, contact lenses, spectacles, and prosthetic eyes, or their coating materials; optical products such as filters, prisms, mirrors, and photographic materials; stationery such as tapes and inks; signboards, markers, and their surface coating materials. For details on these, reference can be made to paragraphs 0158 to 0218 of Japanese Patent Application Laid-Open No. 2009-263617, which is incorporated herein by reference.

[0378] The resin composition of the present invention is preferably used for ultraviolet cutoff filters, lenses, or protective materials. The protective material is not particularly limited in form, and may be in the form of a coating, a film, or a sheet. Furthermore, the resin composition of the present invention can also be used as a binder or adhesive.

[0379] Furthermore, the resin composition of the present invention can also be used in various components of display devices. For example, in the case of a liquid crystal display device, it can be used in various components of the liquid crystal display device, such as an anti-reflection film, a polarizer protective film, an optical film, a phase difference film, a binder, an adhesive, etc. Furthermore, in the case of an organic electroluminescent display device, it can be used in various components of the organic electroluminescent display device, such as an optical film, a polarizer protective film in a circular polarizer, a phase difference film such as a quarter-wave plate, an adhesive, etc.

[0380] Cured products and their applications

[0381] The cured product of the present invention can be obtained using the resin composition of the present invention. The term "cured product" herein includes a dried product obtained by drying the resin composition and a cured product obtained by subjecting the resin composition to a curing reaction.

[0382] The cured product of the present invention can be a molded product obtained by molding the resin composition into a desired shape. About the shape of the molded product, it is possible to suitably select according to use and purpose. For example, a coating film, a film, a sheet, a plate, a lens, a tubular, a fiber, etc. can be enumerated.

[0383] The cured product of the present invention can be preferably used as an optical component. Examples of optical components include ultraviolet cut filters, lenses, and protective materials. Furthermore, it can also be used in polarizing plates and the like.

[0384] 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 liquid crystal display devices and organic electroluminescent display devices.

[0385] When the cured product of the present invention is used in a lens, the cured product of the present invention itself can be formed into a lens shape for use. Furthermore, the cured product of the present invention can be used as a coating on the surface of a lens, an intermediate layer (adhesive layer) of a cemented lens, etc. Regarding cemented lenses, the contents described in paragraphs 0094 to 0102 of International Publication No. 2019 / 131572 can be cited, and such contents are incorporated into this specification.

[0386] The type of protective material is not particularly limited, and examples thereof include protective materials for display devices, protective materials for solar cells, protective materials for window glass, and organic electroluminescent displays. The shape of the protective material is not particularly limited, and examples thereof include coatings, films, and sheets.

[0387] UV absorbers

[0388] The ultraviolet absorber of the present invention comprises a compound represented by the above formula (1) (compound (1)). Compound (1) is the same as described in the above resin composition, and its preferred range is also the same. Compound (1) used in the ultraviolet absorber is preferably a compound represented by the above formula (1a).

[0389] The ultraviolet absorber of the present invention can also be added to a binder or adhesive for use. As a binder, for example, acrylic binders, rubber binders, silicone binders, etc. can be mentioned. Acrylic binders refer to binders containing polymers of (meth) acrylic acid monomers ((meth) acrylic polymers). As adhesives, for example, urethane resin adhesives, polyester adhesives, acrylic resin adhesives, ethylene vinyl acetate resin adhesives, polyvinyl alcohol adhesives, polyamide adhesives and silicone adhesives can be mentioned. Among them, from the perspective of high adhesive strength, urethane resin adhesives or silicone adhesives are preferred as adhesives. Commercially available products sold on the market can be used as adhesives. As examples of commercially available products, urethane resin adhesive (LIS-073-50U: trade name) from TOYO INK CO., LTD. and acrylic binder (SK Dyne-SF2147: trade name) from Soken Chemical & Engineering Co., Ltd. can be mentioned. The adhesive can be further used together with a curing agent. Examples of commercially available curing agents include CR-001 (trade name) manufactured by TOYO INK CO., LTD.

[0390] The content of 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 compound (1) or two or more. When containing two or more compounds (1), the total amount of these compounds (1) is preferably within the above range.

[0391] The ultraviolet absorber of the present invention preferably further contains a compound represented by the above formula (2) (compound (2)). The compound (2) is the same as that described in the above resin composition, and the preferred range is also the same.

[0392] When the ultraviolet absorber contains compound (2), the content of compound (2) is preferably 5 parts by mass or less, more preferably 3 parts by mass or less, and even more preferably 1 part by mass or less, relative to 100 parts by mass of compound (1). The lower limit is preferably 0.1 parts by mass or more. The ultraviolet absorber may contain only one compound (2) or two or more. When containing two or more compounds (2), the total amount of these compounds is preferably within the above range.

[0393] Optical components

[0394] The optical component of the present invention comprises the above-mentioned ultraviolet light absorber of the present invention. The optical component of the present invention also preferably comprises a cured product obtained using the above-mentioned resin composition of the present invention. The cured product of the present invention can be 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 application and purpose. For example, a coating film, a film, a sheet, a plate, a lens, a tubular, a fiber, etc. can be mentioned.

[0395] Furthermore, the optical component of the present invention can be obtained using the adhesive or pressure-sensitive adhesive containing the ultraviolet absorber of the present invention. For example, the optical component can be a component in which a polarizer and a polarizer protective film are bonded using the adhesive or pressure-sensitive adhesive containing the ultraviolet absorber.

[0396] Examples of the optical components include ultraviolet cut filters, lenses, and protective materials.

[0397] 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 liquid crystal display devices and organic electroluminescent display devices.

[0398] Examples of the lens include lenses in which the cured product of the present invention itself is formed into a lens shape; lenses in which the ultraviolet absorber of the present invention is contained in a coating film on the lens surface, an intermediate layer (adhesive layer, adhesive layer) for bonding lenses, and the like.

[0399] The type of protective material is not particularly limited, and examples thereof include protective materials for display devices, solar cells, and window glass. The shape of the protective material is not particularly limited, and examples thereof include coatings, films, and sheets.

[0400] Furthermore, as one mode of the optical component, a resin film can be mentioned. The resin film can be formed using the resin composition of the present invention described above. As the resin of the resin composition used for forming the resin film, the above resins can be mentioned, preferably (meth) acrylic resin, polyester fiber, cyclic olefin resin and cellulose acylate resin, more preferably cellulose acylate resin. The resin composition comprising the cellulose acylate resin can include the additives described in paragraphs 0022 to 0067 of Japanese Patent Application Laid-Open No. 2012-215689. As such additives, for example, sugar esters can be mentioned. By adding a sugar ester compound to the resin composition comprising the cellulose acylate resin, the total haze and internal haze can be reduced without damaging the visual appearance of the optical properties and without performing a heat treatment before the stretching process. As sugar esters, for example, sugar ester 1 and sugar ester 2 described in the embodiments described later can be mentioned. A resin film (cellulose acylate film) made of a resin composition containing a cellulose acylate resin can be produced by the method described in paragraphs 0068 to 0096 of JP-A-2012-215689. Furthermore, the resin film may be further laminated with a hard coat layer described in paragraphs 0097 to 0113 of JP-A-2012-215689.

[0401] Another embodiment of the optical component includes a laminate comprising a transparent support substrate and a resin layer. In this case, at least one of the support substrate and the resin layer is obtained using the resin composition of the present invention or contains the ultraviolet absorber of the present invention. Such an optical component can be preferably used as a film or sheet-like ultraviolet cutoff filter or protective material.

[0402] As a supporting substrate, it is preferred to have transparency within a range that does not impair optical performance. Transparency of the supporting substrate means optical transparency, specifically, it means that the total light transmittance of the supporting substrate is 85% or more. The total light transmittance of the supporting substrate is preferably 90% or more, more preferably 95% or more. The total light transmittance of the supporting substrate can be measured by the following method. The total light transmittance of the supporting substrate is a value obtained by measuring the spectral spectrum of the supporting substrate using a UV / vis spectrometer (for example, UV / vis spectrometer UV3400 manufactured by SHIMADZU CORPORATION) and the measured value.

[0403] As a preferred example of the supporting substrate, a resin film can be cited. Examples of the resin forming the supporting substrate include ester resins (e.g., polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polybutylene terephthalate (PBT), polycyclohexane dimethyl terephthalate (PCT), etc.), olefin resins (e.g., polypropylene (PP), polyethylene (PE), etc.), polyvinyl chloride (PVA), and cellulose triacetate (TAC). Among them, PET is preferred due to its versatility.

[0404] The supporting substrate can be obtained by molding the above-mentioned resin into a plate-like shape by conventional methods. Alternatively, a commercially available resin film or the like can be used as the supporting substrate. Alternatively, the supporting substrate can be obtained using the resin composition of the present invention.

[0405] The thickness of the support substrate can be appropriately selected depending on the application, purpose, etc. Usually, the thickness is preferably 5 μm to 2500 μm, more preferably 20 μm to 500 μm.

[0406] The resin layer is a layer formed of a resin composition. The resin composition of the present invention can be used as the resin composition. The resin layer may be a layer that has been dried and solidified, or a cured layer obtained by a curing reaction.

[0407] The thickness of the resin layer is not particularly limited and can be arbitrarily selected based on the desired visible light transmittance. For example, the thickness of the resin layer can be set to 5 μm to 2500 μm. The thickness of the resin layer is preferably 5 μm to 500 μm, and more preferably 5 μm to 100 μm, particularly from the perspectives of ensuring the function of blocking or even suppressing ultraviolet and blue light, visible light transmittance, and ease of handling.

[0408] Furthermore, as the transparent support substrate, a releasable support substrate (releasable laminate film) can be used. An optical component using such a support substrate can be preferably used for a polarizing plate or the like.

[0409] Examples of the releasable laminated film include a film having a structure in which a support made of polyethylene terephthalate and a resin layer containing the ultraviolet absorber of the present invention are in direct contact with each other.

[0410] The support of the peelable laminate 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, more preferably 0.08 N / 25 mm or more and 0.50 N / 25 mm or less, and even more preferably 0.11 N / 25 mm or more and 0.20 N / 25 mm or less. If the stress is 0.05 N / 25 mm or more, it is preferred because it is less likely to peel during polarizing plate processing. If the stress is 2.00 N / 25 mm or less, it is preferred because it is less likely to bend the polarizing plate when peeling from the support. After the surface of the optical film cut into a peelable laminate film with a width of 25 mm and a length of 80 mm was bonded and fixed to a glass substrate using an acrylic adhesive sheet, the substrate film was clamped at one end of the length direction of the test piece (the side with a width of 25 mm) using a tensile testing machine (RTF-1210 manufactured by A&D Company, Limited). In an atmosphere with a temperature of 23°C and a relative humidity of 60%, a 90° peel test was carried out at a crosshead speed of 200 mm / min (clamping movement speed) (in accordance with Japanese Industrial Standard (JIS) K 6854-1:1999 "Adhesives - Peel Adhesion Strength Test Method - Part 1: 90 Degree Peel") to evaluate the stress when the support body of the peelable laminate film is peeled off from the resin layer.

[0411] The support body possessed by the peelable laminated film is described. The support body possessed by the peelable laminated film can use a support body containing polyethylene terephthalate (PET). The main component of the support body (the component with the largest mass-based content among the components constituting the support body) is preferably polyethylene terephthalate (PET). From the viewpoint of mechanical strength, 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 support body can be dissolved in hexafluoroisopropanol (HFIP) and the weight average molecular weight of PET can be determined by the aforementioned GPC method. The thickness of the support body is not particularly limited, but is preferably 0.1 to 100 μm, more preferably 0.1 to 75 μm, further preferably 0.1 to 55 μm, and particularly preferably 0.1 to 10 μm. In addition, the support body can be subjected to corona treatment, glow discharge treatment, primer coating, etc. as well-known surface treatments.

[0412] The peelable laminate film can be produced by coating a solution comprising the ultraviolet absorber of the present invention, a resin, and a solvent onto the support and drying the solution to form a resin layer. The solvent can be appropriately selected from the perspectives of being able to dissolve or disperse the resin, facilitating a uniform surface during the coating and drying steps, ensuring liquid storage stability, and having an appropriate saturated vapor pressure.

[0413] Another embodiment of the optical component includes a laminate having a hard coat layer, a transparent support substrate, and an adhesive layer or a pressure-sensitive adhesive layer laminated in this order. Such a laminate can be preferably used as an ultraviolet cut filter or a protective material (protective film, protective sheet).

[0414] In the optical component of this embodiment, the ultraviolet absorber of the present invention may be contained in any one of the support substrate, the hard coat layer, and the adhesive layer or the pressure-sensitive adhesive layer.

[0415] The optical component of this mode has a hard coat on a supporting substrate. By having a hard coat on the outermost layer of the optical component, the scratch resistance of the optical component can be improved. The hard coat can be formed by any one of a wet coating method or a dry coating method (vacuum film forming). From the aspect of excellent productivity, the wet coating method is preferably used. When forming a hard coat with the resin composition of the present invention, it is preferably formed by a wet coating method.

[0416] When the hard coat layer is not a cured product of the resin composition of the present invention, as the hard coat layer, for example, Japanese Patent Application Laid-Open No. 2013-045045, Japanese Patent Application Laid-Open No. 2013-043352, Japanese Patent Application Laid-Open No. 2012-232459, Japanese Patent Application Laid-Open No. 2012-128157, Japanese Patent Application Laid-Open No. 2011-131409, Japanese Patent Application Laid-Open No. 2011-131404, Japanese Patent Application Laid-Open No. 2011-126162, Japanese Patent Application Laid-Open No. 2011-075705, Japanese Patent Application Laid-Open No. 2009-286981 ... Hard coat layers described in Japanese Patent Application Publication No. 2009-263567, Japanese Patent Application Publication No. 2009-075248, Japanese Patent Application Publication No. 2007-164206, Japanese Patent Application Publication No. 2006-096811, Japanese Patent Application Publication No. 2004-075970, Japanese Patent Application Publication No. 2002-156505, Japanese Patent Application Publication No. 2001-272503, International Publication No. 2012 / 018087, International Publication No. 2012 / 098967, International Publication No. 2012 / 086659, and International Publication No. 2011 / 105594.

[0417] From the viewpoint of further improving the scratch resistance, the thickness of the hard coat layer is preferably 5 μm to 100 μm.

[0418] The optical component of this embodiment has a bonding layer or adhesive layer on the side of the supporting substrate opposite to the side having the hard coat layer. The type of adhesive or adhesive used for the bonding layer or adhesive layer is not particularly limited. The above-mentioned adhesives or adhesives can be mentioned. In addition, an adhesive or adhesive to which the ultraviolet absorber of the present invention is added can also be used. In addition, the resin composition of the present invention can be used in the adhesive or adhesive. Regarding the adhesive or adhesive, it is also preferred to use an acrylic resin described in paragraphs 0056 to 0076 of Japanese Patent Application Publication No. 2017-142412 and an adhesive or adhesive containing a crosslinking agent described in paragraphs 0077 to 0082 of Japanese Patent Application Publication No. 2017-142412. Furthermore, the adhesive or pressure-sensitive adhesive may contain an adhesion improver (silane compound) described in paragraphs 0088 to 0097 of JP-A-2017-142412 and an additive described in paragraph 0098 of JP-A-2017-142412. Furthermore, the adhesive layer or pressure-sensitive adhesive layer can be formed by the method described in paragraphs 0099 to 0100 of JP-A-2017-142412.

[0419] From the viewpoint of achieving both adhesive strength and workability, the thickness of the adhesive layer or pressure-sensitive adhesive layer is preferably 5 μm to 100 μm.

[0420] <Optical Component Arrangement for Display Applications>

[0421] The optical component of the present invention can be preferably used as a component of displays such as liquid crystal display devices (LCD) and organic electroluminescent display devices (OLED).

[0422] Liquid Crystal Display Devices

[0423] Examples of liquid crystal display devices include those containing the ultraviolet absorber of the present invention in components such as anti-reflection films, polarizer protective films, optical films, phase difference films, adhesives, and pressure-sensitive adhesives. The optical component containing the ultraviolet absorber of the present invention can be arranged on either the observer side (front side) or the backlight side in the liquid crystal cell, and can be arranged on either the side away from the liquid crystal cell (outside) or the side close to the liquid crystal cell (inside) in the polarizer. Figures 1 to 10 A preferred structure of a liquid crystal display device having an optical component containing the ultraviolet absorber of the present invention is shown in FIG. Figures 1 to 10 This is a schematic diagram; the relationship between the thickness and position of each layer may not necessarily be consistent with the actual situation. Figure 1 This is a schematic diagram showing a structure in which the ultraviolet absorber of the present invention is added to the front polarizer protective film. Figure 2 This is a schematic diagram showing a structure in which the ultraviolet absorber of the present invention is added to a polarizing plate protective film on the backlight side. Figure 3 This is a schematic diagram showing a structure in which the ultraviolet absorber of the present invention is added to the inner protective film on the front side. Figure 4 This is a schematic diagram showing a structure in which the ultraviolet absorber of the present invention is added to the inner protective film on the backlight side. In addition, the inner protective film can also serve as a retardation film. Figure 5 This is a schematic diagram showing a structure in which an optical film containing the ultraviolet absorber of the present invention is bonded to a front retardation film via an adhesive or a bonding agent. Figure 6 This is a schematic diagram showing a structure in which an optical film containing the ultraviolet absorber of the present invention is bonded to a retardation film on the backlight side via an adhesive or a pressure-sensitive adhesive. Figure 7 This is a schematic diagram showing a structure in which the ultraviolet absorber of the present invention is added to the adhesive or binder on the front side. Figure 8 This is a schematic diagram showing a structure in which the ultraviolet absorber of the present invention is added to a binder or adhesive on the backlight side. Figure 9 This is a schematic diagram showing a structure in which the ultraviolet absorber of the present invention is added to the front functional layer. Figure 10 This is a schematic diagram showing a structure in which the ultraviolet absorber of the present invention is added to a functional layer on the backlight side. Examples of the functional layer include an antireflection layer and a hard coat layer.

[0424] When the optical component containing the ultraviolet absorber of the present invention is arranged on the viewer side (front side), it is possible to prevent degradation of materials in the liquid crystal cell due to external light.

[0425] When the ultraviolet absorber of the present invention is added to a polarizer protective film, the cellulose acylate film or the resin layer of the peelable laminated film is preferably used as the polarizer protective film. When the ultraviolet absorber of the present invention is added to a polarizer protective film, the ultraviolet absorber of the present invention may be contained on either the side close to the liquid crystal cell or the side away from the liquid crystal cell, or on both sides.

[0426] Cellulose acylate films are used in polarizing plates used in liquid crystal displays. A polarizing plate including a cellulose acylate film can be produced by the method described in paragraphs 0114 to 0117 of JP-A-2012-215689.

[0427] Furthermore, when the resin layer in the above-mentioned peelable laminated film is used as a polarizer protective film, the surface of the peelable laminated film on the side opposite to the support side interface of the resin layer is attached to the polarizer by an adhesive, and then the support is peeled off, thereby obtaining a polarizer having a polarizer and a resin layer containing the ultraviolet absorber of the present invention. The penetration depth of the resin layer containing the above-mentioned ultraviolet absorber varies not only according to the difference in the (solubility parameter) SP value between the adhesive and the resin layer containing the ultraviolet absorber, but also according to the time conditions (temperature, time) after the adhesive and the resin layer containing the ultraviolet absorber come into contact. For example, low temperature / short time conditions are suitable for suppressing penetration. Furthermore, regarding the penetration depth, since the penetration rate can be reduced once by irradiating active energy rays, it is also effective to perform additional irradiation after suppressing the penetration depth by temporary irradiation for the purpose of promoting curing for ensuring the durability of the polarizer.

[0428] If necessary, the surface of the peelable laminate film opposite to the support-side interface of the ultraviolet absorbent-containing resin layer may be hydrophilized by glow discharge treatment, corona treatment, alkali saponification treatment, or the like.

[0429] The support can be peeled off by the same method as the separator (peeling film) peeling process performed in conventional polarizers with adhesives. The support can be peeled off directly after the step of laminating the resin layer containing the ultraviolet absorber and the polarizer with the adhesive and drying them, or it can be temporarily wound into a roll after the drying step and peeled off in a subsequent step.

[0430] Organic electroluminescent display device

[0431] Examples of organic electroluminescent displays include those containing the ultraviolet absorber of the present invention in components such as optical films, polarizer protective films in circular polarizers, phase difference films such as quarter-wave plates, adhesives, and bonding agents. Furthermore, a method of attaching the above-mentioned peelable laminated film to the circular polarizer via an adhesive or bonding agent is also preferred as a method for introducing the ultraviolet absorber of the present invention. By adding the ultraviolet absorber of the present invention to the above-mentioned structure, degradation of the organic electroluminescent display device caused by external light can be suppressed.

[0432] Figures 11 to 13 A preferred structure of an organic electroluminescent display device having an optical component containing the ultraviolet absorber of the present invention is shown. Figures 11 to 13 This is a schematic diagram; the relationship between the thickness and position of each layer may not necessarily be consistent with the actual situation. Figure 11 This is a schematic diagram showing a structure in which the ultraviolet absorber of the present invention is added to a polarizing plate protective film. Figure 12This is a schematic diagram showing a structure in which the ultraviolet absorber of the present invention is added to an adhesive or a binder. Figure 13 This is a schematic diagram showing a structure in which an optical film containing the ultraviolet absorber of the present invention is bonded to a touch panel via an adhesive or a pressure-sensitive adhesive.

[0433] <Compounds and methods for synthesizing the same>

[0434] The compound of the present invention is a compound represented by the above formula (1a). The compound represented by formula (1a) is the same as that described in the above resin composition, and the preferred range is also the same. The compound represented by formula (1a) can be preferably used as a UV absorber.

[0435] The maximum absorption wavelength of the compound represented by formula (1a) preferably exists in the wavelength range of 381 to 420 nm, and more preferably exists in the wavelength range of 381 to 400 nm.

[0436] The molar absorption coefficient ε of the compound represented by formula (1a) at a wavelength of 405 nm was calculated according to the following formula: 405 It is preferably 500 or more, more preferably 1000 or more, further preferably 2000 or more, and particularly preferably 3000 or more.

[0437] ε 405 =ε max ×(A 405 / A max )

[0438] ε 405 is the molar absorption coefficient of the compound represented by formula (1a) at a wavelength of 405 nm, ε max is the molar absorptivity of the compound represented by formula (1a) at the maximum absorption wavelength, A 405 is the absorbance of the compound represented by formula (1a) at a wavelength of 405 nm, A max is the absorbance of the compound represented by formula (1a) at the maximum absorption wavelength.

[0439] In the optical absorption spectrum of the compound represented by formula (1a) measured in ethyl acetate, the absorbance A at a wavelength of 405 nm is 405 and the absorbance A at a wavelength of 430 nm 430 The ratio (A 430 / A 405 ) is preferably less than 0.13, more preferably less than 0.10. The lower limit of the above ratio is not particularly limited and can be set to 0 or more.

[0440] The compound represented by the above formula (1a) can be synthesized through a step of reacting a compound represented by the formula (2a) with a halogenated alkyl compound or a carboxylic acid halide.

[0441] [Chemical Formula 21]

[0442]

[0443] In formula (2a), R 11a and R 12a Each independently represents an alkyl group,

[0444] R 14a represents an alkyl group or an alkoxy group,

[0445] R 15a represents a hydrogen atom, an alkyl group or an alkoxy group;

[0446] R 14a With R 15a They may be bonded to each other to form a ring.

[0447] R in formula (2a) 11a 、R 12a 、R 14a and R 15a The meanings of the groups represented are the same as those of R in formula (2). 11 、R 12 、R 14 and R 15 The groups described are the same and the preferred ranges are also the same.

[0448] Examples of the halogenated alkyl compound to be reacted with the compound represented by formula (2a) include: 30 -X 30 Examples of the carboxylic acid halide to be reacted with the compound represented by formula (2a) include: 30 -C(=O)-X 30 The compound represented by R 30 is an alkyl group, X 30 is a halogen atom. 30 The number of carbon atoms in the alkyl group represented 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 either linear or branched. The alkyl group may have a substituent. As the substituent, the groups described in the substituent T above can be cited. As X 30 Examples of the halogen atom represented by include a chlorine atom, a bromine atom and an iodine atom.

[0449] Example

[0450] Hereinafter, the present invention will be further described in detail with reference to the following examples. The materials, usage amounts, ratios, processing contents, processing steps, etc. shown in the following examples can be appropriately changed without departing from the main purpose of the present invention. Therefore, the scope of the present invention is not limited to the specific examples shown below. In addition, in the structural formula shown below, 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, and Ac is an acetyl group.

[0451] <Synthesis example>

[0452] (Synthesis Example 1) (Synthesis of Compound (1)-1)

[0453] Intermediate 1-1 was synthesized according to the following scheme. In the following scheme, the synthesis of Intermediate 1-1 from methyl p-benzoquinone was carried out with reference to the method described in paragraph 0176 of JP-A-2016-081035, using methyl p-toluquinone instead of 2-tert-butyl-1,4-benzoquinone.

[0454] [Chemical Formula 22]

[0455]

[0456] Next, compound (2)-31 was synthesized according to the following synthesis scheme. Referring to the method described in paragraphs 0154-0155 of Japanese Patent No. 5376885, the synthesis of compound (2)-31 from intermediate 1-1 was carried out using intermediate 1-1 instead of 1-(4,7-dihydroxybenzo[1,3]dithiol-2-ylidene)piperidinium acetate.

[0457] [Chemical Formula 23]

[0458]

[0459] Next, 0.5 g of compound (2)-31, 0.39 g of potassium carbonate and 5 ml of N,N-dimethylacetamide were mixed and stirred at room temperature for 5 minutes. 0.46 g of 2-iodopropane was added thereto and stirred while heating at 90°C for 4 hours. After the reaction was completed, the mixture was cooled to room temperature, 1.5 ml of water was added and stirred for 20 minutes. After filtering out the precipitated solid, 2.5 ml of methanol and 2.5 ml of acetonitrile were added and heated and refluxed for 1 hour under a nitrogen atmosphere. After cooling to room temperature, the solid was filtered out after stirring at room temperature for 1 hour and washed with a mixed solvent of 2.5 ml of methanol and 2.5 ml of acetonitrile, thereby obtaining 0.4 g of compound (1)-1 (yield 70%). 1H-NMR(CDCl3): δ6.70(s,1H), 4.62(m,1H), 4.42(m,1H), 3.66(m,4H), 2.34(s,3H), 1.54(m,4H), 1.4~1.2(m,16H), 0.91(m,6H)

[0460] [Chemical Formula 24]

[0461]

[0462] (Synthesis Example 2) (Synthesis of Compounds (1)-2 to (1)-8)

[0463] Compounds (1)-2 to (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.

[0464] [Chemical Formula 25]

[0465]

[0466] (Synthesis Example 3) (Synthesis of Compounds (1)-9 to (1)-10)

[0467] Compound (1)-9 and Compound (1)-10 were synthesized in the same manner as in Synthesis Example 1, except that 1,2-dimethyl-pyrazolidine-3,5-dione was used instead of Intermediate 1-2.

[0468] [Chemical Formula 26]

[0469]

[0470] (Synthesis Example 4) (Synthesis of Compound (1)-11)

[0471] Compound (1)-11 was synthesized by the same method as in Synthesis Example 1, except that 2-tert-butyl-1,4-benzoquinone was used instead of methyl-p-benzoquinone.

[0472] [Chemical Formula 27]

[0473]

[0474] (Synthesis Example 5) (Synthesis of Compound (1)-12)

[0475] Compound (1)-12 was synthesized by the same method as in Synthesis Example 1, except that 2-phenyl-1,4-benzoquinone was used instead of methyl-p-benzoquinone.

[0476] [Chemical Formula 28]

[0477]

[0478] (Synthesis Example 6) (Synthesis of Compound (1)-13)

[0479] Compound (2)-40 was synthesized in the same manner as in Synthesis Example 1 according to the following scheme.

[0480] [Chemical Formula 29]

[0481]

[0482] Compound (1)-13 was synthesized in the same manner as in Synthesis Example 1 according to the following scheme.

[0483] [Chemical formula 30]

[0484]

[0485] (Synthesis Example 7) (Synthesis of Compound (1)-14)

[0486] With reference to the method described in paragraphs 0154 to 0155 of Japanese Patent No. 5376885, compound (1)-14 was synthesized according to the following scheme.

[0487] [Chemical Formula 31]

[0488]

[0489] (Synthesis Example 8) (Synthesis of Compound (1)-15)

[0490] Intermediate 15-2 was synthesized according to the following scheme using the same method as in Synthesis Example 1. In the following scheme, Intermediate 15-1 was used instead of Intermediate 1-2 used in Synthesis Example 1 to synthesize Intermediate 15-2. Intermediate 15-1 was also synthesized according to the method described in Journal of the American Chemical Society, 2009, vol. 131, 33, pp. 11875-11881.

[0491] [Chemical Formula 32]

[0492]

[0493] Compound (1)-15 was synthesized in the same manner as in Synthesis Example 1 according to the following scheme.

[0494] [Chemical Formula 33]

[0495]

[0496] (Synthesis Example 9) (Synthesis of Compound (1)-16)

[0497] Intermediate 16-2 was synthesized according to the following scheme. In the following scheme, 1,4-naphthoquinone was used instead of methyl-p-benzoquinone used in Synthesis Example 1, and Intermediate 16-1 was used instead of Intermediate 1-2, thereby synthesizing Intermediate 16-2 from 1,4-naphthoquinone.

[0498] [Chemical Formula 34]

[0499]

[0500] Compound (1)-16 was synthesized in the same manner as in Synthesis Example 1 according to the following scheme.

[0501] [Chemical Formula 35]

[0502]

[0503] (Synthesis Example 10) (Synthesis of Compound (1)-37 and Compound (1)-46)

[0504] Compound (2)-22 was synthesized according to the following scheme. In the following scheme, Intermediate 37-1 was used instead of Intermediate 1-2 used in Synthesis Example 1, thereby synthesizing Compound (2)-22 from Intermediate 1-1.

[0505] [Chemical Formula 36]

[0506]

[0507] Compound (1)-37 and compound (1)-46 were synthesized in the same manner as in Synthesis Example 1, except that compound (2)-22 was used instead of compound (2)-31 and the corresponding alkylating agent was used instead of 2-iodopropane.

[0508] [Chemical Formula 37]

[0509]

[0510] (Synthesis Example 11) (Synthesis of Compound (1)-47)

[0511] Compound (2)-1 was synthesized according to the following scheme. In the following scheme, 2,3-dimethyl-p-benzoquinone was used instead of the methyl-p-benzoquinone used in Synthesis Example 1, thereby synthesizing Compound (2)-1 from 2,3-dimethyl-p-benzoquinone.

[0512] [Chemical Formula 38]

[0513]

[0514] Compound (1)-47 was synthesized in the same manner as in Synthesis Example 1 according to the following scheme.

[0515] [Chemical Formula 39]

[0516]

[0517] (Synthesis Example 12) (Synthesis of Compound (1)-48)

[0518] Compound (2)-54 was synthesized according to the following scheme. In the following scheme, 2,3-dimethyl-p-benzoquinone was used instead of the methyl-p-benzoquinone used in Synthesis Example 1, thereby synthesizing compound (2)-54 from 2,3-dimethyl-p-benzoquinone.

[0519] [Chemical Formula 40]

[0520]

[0521] Compound (1)-48 was synthesized in the same manner as in Synthesis Example 1 according to the following scheme.

[0522] [Chemical Formula 41]

[0523]

[0524] <Test Example 1>

[0525] 2 mg of the compounds listed in the following table (Compounds (1)-1 to (1)-16, (1)-37, (1)-46, (1)-47, (1)-48, and Comparative Compounds 1 to 4) were dissolved in 100 mL of ethyl acetate and then diluted with ethyl acetate until the absorbance of the solution was within the range of 0.6 to 1.2, thereby preparing sample solutions 101 to 120. In addition, the compounds with the following structures were used as Comparative Compounds 1 to 4.

[0526] [Chemical Formula 42]

[0527]

[0528] The absorbance of each sample solution at 101 to 120 nm was measured using a spectrophotometer UV-1800PC (manufactured by Shimadzu Corporation) through a 1 cm quartz cell. The maximum absorption wavelength (λ) of each sample solution was determined from the obtained spectra. max ). max The values are listed in the following table.

[0529] The molar absorption coefficient (ε) at a wavelength of 405 nm was calculated according to the following formula: 405 ).

[0530] ε 405 =ε max ×(A 405 / A max )

[0531] ε 405 is the molar absorption coefficient of the sample solution at a wavelength of 405 nm, ε max is the molar absorptivity 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 It is the absorbance of the sample solution at the maximum absorption wavelength.

[0532] ε 405 The evaluation was conducted in three stages: A was assigned to a value of 3000 or more, B was assigned to a value of less than 3000 and 500 or more, and C was assigned to a value of less than 500. 405 The larger the value of , the higher the absorption capacity at 405nm. The evaluation results are recorded in ε in the following Table 1. 405 One column.

[0533] The absorbance at 430 nm was calculated, with the absorbance of the sample solution at 405 nm being set to 1. Coloration was evaluated by assigning an absorbance of less than 0.13 at 430 nm to A and a value of 0.13 or greater to B. Lower absorbance values at 430 nm indicate less coloration. The results are shown in the "Coloration" column of Table 1 below.

[0534] [Table 1]

[0535] Sample solution No. Type of compound <![CDATA[λ max (nm)]]> <![CDATA[ε 405 ]]> Coloring 101 Compound (1)-1 383 A A 102 Compound (1)-2 381 A A 103 Compound (1)-3 383 A A 104 Compound (1)-4 383 A A 105 Compound (1)-5 383 A A 106 Compound (1)-6 383 A A 107 Compound (1)-7 384 A A 108 Compound (1)-8 383 A A 109 Compound (1)-9 381 A A 110 Compound (1)-10 382 A A 111 Compound (1)-11 383 A A 112 Compound (1)-12 383 A A 113 Compound (1)-13 388 A A 114 Compound (1)-14 382 A A 115 Compound (1)-15 393 A A 116 Compound (1)-16 388 A A 117 Compound (1)-37 386 A A 118 Compound (1)-46 387 A A 119 Compound (1)-47 385 A A 120 Compound (1)-48 388 A A 121 Comparative Compound 1 350 C B 122 Comparative Compound 2 352 C A 123 Comparative Compound 3 350 C B 124 Comparative Compound 4 380 B A

[0536] As shown in the above table, the molar absorption coefficients (ε) of compounds (1)-1 to (1)-16, compound (1)-37, compound (1)-46, compound (1)-47, and compound (1)-48 at a wavelength of 405 nm are 405 ) is high and less colored.

[0537] <Test Example 2-1>

[0538] The compounds listed in the following table, 7.6 g of chloroform and 1.1 g of (meth) acrylic resin (Dianal BR-80, Mitsubishi Chemical Corporation, containing 60% by mass or more of methyl methacrylate as a monomer unit, Mw 95000) 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 (1)-13, compound (1)-14, compound (1)-5, compound (1)-37, compound (1)-46, compound (1)-47, compound (1)-48, and comparative compounds 1 to 4 listed in the column of the type of compound in the following Table 2 are compounds of the above-mentioned structures, respectively.

[0539] (Evaluation of surface unevenness)

[0540] The resin film produced above was observed using an optical microscope (MX-61L, manufactured by Olympus Corporation) at 200x bright field magnification to check for any unevenness. A uniform film with no unevenness observed under the optical microscope was judged to have excellent resistance to thermal stress during film formation. The evaluation results for planar unevenness are shown in Table 2 below.

[0541] A: No unevenness was observed under an optical microscope.

[0542] B: Slight unevenness was observed under an optical microscope.

[0543] C: Obvious unevenness was observed under an optical microscope.

[0544] (Lightfastness)

[0545] The resin film prepared above was subjected to a light resistance test under the following conditions 1 to determine the maximum absorption wavelength (λ max ) was used to evaluate the light resistance of the resin film. max ) and then measured the absorbance at the maximum absorption wavelength (λ max ) is the absorbance at .

[0546] (Condition 1)

[0547] Equipment: Xenon weathering tester (Suga Test Instruments Co., Ltd.: XL75)

[0548] Illumination: 10klx(40w / m 2 )

[0549] Trial period: 1 week

[0550] Environment: 23°C, relative humidity 50%

[0551] According to the maximum absorption wavelength (λ max ) was taken as the absorbance value at , and the absorbance maintenance rate (%) was calculated using the following formula. The maintenance rate was calculated using the following formula.

[0552] Absorbance maintenance rate (%) = 100 × (the resin film after irradiation at λ max Absorbance of the resin film before irradiation at λ max Absorbance at

[0553] A: Absorbance maintenance rate is more than 90%

[0554] B: Absorbance maintenance rate is 80% or more and less than 90%

[0555] C: Absorbance maintenance rate is less than 80%

[0556] Furthermore, the degree of coloration change of the resin film after the light resistance test was visually confirmed. The evaluation results are shown in Table 2 below.

[0557] [Table 2]

[0558]

[0559] Compared to resin films 213a-216a, resin films 201a-212a absorb light at wavelengths near 400 nm more strongly and are superior in absorbing ultraviolet light at longer wavelengths. Furthermore, resin films 201a-212a exhibit minimal coloration. Specifically, resin films 201a-212a exhibit significant light absorption near 400 nm and exhibit minimal coloration.

[0560] Furthermore, as shown in the above table, the resin films 201 a to 212 a have little surface unevenness and are also excellent in light resistance.

[0561] Furthermore, regarding the resin composition used to form the resin films 20a1 to 212a, the storage stability of the resin composition is improved by containing the compound (2) (the compound represented by formula (2)) described above in this specification. For example, even when the resin composition is stored at 5°C for 2 weeks to form a resin film, no precipitation of the compound (1) is found.

[0562] <Test Example 2-2>

[0563] The compounds described in the following table, 7.6 g of chloroform and 1.1 g of (meth) acrylic resin (Dianal BR-80, Mitsubishi Chemical Corporation, containing 60% by mass or more of methyl methacrylate as a monomer unit, Mw 95000) 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, among the compounds described in the "Type of Compound" column of Table 3 below, compound (1)-1, compound (1)-5, and compound (1)-8 are compounds of the above-mentioned structures, respectively. Furthermore, UV-1 to UV-6 are compounds of the following structures.

[0564] [Chemical Formula 43]

[0565]

[0566] (Evaluation of surface unevenness)

[0567] The surface unevenness of the resin film produced above was evaluated by the same method and evaluation criteria as in Test Example 2-1.

[0568] (Light resistance 2 (maintenance of absorbance at 405 nm))

[0569] The resin film produced above was subjected to a light resistance test under Condition 1 of Test Example 2-1. The absorbance retention rate at a wavelength of 405 nm was determined, and Light Resistance 2 was evaluated. Specifically, the absorbance of the resin film at a wavelength of 405 nm was measured, and then the absorbance of the resin film at a wavelength of 405 nm was measured after the light resistance test, which was conducted for one week under Condition 1. The absorbance retention rate (%) was calculated using the following formula based on the absorbance values at 405 nm of the resin film before and after the light resistance test. The retention rate was calculated using the following formula.

[0570] Absorbance maintenance rate (%) = 100 × (absorbance of the resin film at a wavelength of 405 nm after irradiation) / (absorbance of the resin film at a wavelength of 405 nm before irradiation)

[0571] A: Absorbance maintenance rate is more than 90%

[0572] B: Absorbance maintenance rate is 80% or more and less than 90%

[0573] C: Absorbance maintenance rate is less than 80%

[0574] [Table 3]

[0575]

[0576] The resin films 201b to 206b have a large absorption of light near a wavelength of 400nm and are excellent in absorbing ultraviolet rays on the long wavelength side. Furthermore, the retention rate of absorbance at 405nm after the light resistance test is also good, indicating excellent light resistance.

[0577] <Test Example 3>

[0578] The resin film 301 was produced by the method shown below.

[0579] (1) Preparation of raw materials

[0580] (1-1) Preparation of cellulose acylate

[0581] Cellulose acylate with an acetyl substitution degree of 2.85 was prepared. Sulfuric acid (7.8 parts by mass per 100 parts by mass of cellulose) was added as a catalyst, and the carboxylic acids were added, and the acylation reaction was carried out at 40°C. The total degree of substitution and the degree of substitution at the 6th position were then adjusted by adjusting the amount of sulfuric acid catalyst, the amount of water, and the aging time. The aging temperature was 40°C. Furthermore, the cellulose acylate was washed with acetone to remove low-molecular-weight components.

[0582] (1-2) Preparation of sugar ester compounds

[0583] The sugar ester compound was prepared by the following method.

[0584] First, sugar ester compound 1 having the following structure was synthesized by the method described in the synthesis of exemplary compound 3 in paragraph 0054 of International Publication No. 2009 / 003164. Sugar ester compound 2 was also synthesized by the same method.

[0585] (2) Preparation of dopants

[0586] The following composition was placed in a mixing tank and stirred to dissolve the components. The mixture was then heated at 80° C. for about 180 minutes and then filtered through filter paper with an average pore size of 34 μm and a sintered metal filter with an average pore size of 10 μm.

[0587] (Composition of dopants)

[0588] Cellulose acylate (substitution degree 2.85) 100.0 parts by mass

[0589] Sugar ester 1...7.5 parts by mass

[0590] Sugar ester 2...2.5 parts by mass

[0591] Ultraviolet absorber 1 (compound (1)-5) 0.1 parts by mass

[0592] Ultraviolet absorber 2 (comparative compound 5) 0.1 parts by mass

[0593] Dichloromethane 475.3 parts by mass

[0594] Methanol...103.9 parts by mass

[0595] Butanol...4.6 parts by mass

[0596] The solid content concentration of the dopant was 16.0% by mass, the amount of plasticizer added was the ratio relative to the cellulose ester, and the solvent of the dopant was methylene chloride / methanol / butanol = 81 / 18 / 1 (mass ratio).

[0597] The specific sugar ester structure is shown below. Sugar ester 1 was added in an amount of 7.5% by mass, and a sugar ester with the following structure was used with an average degree of substitution of 5.5. The degree of substitution was calculated by HPLC (high performance liquid chromatography). Sugar ester 2 was added in an amount of 2.5% by mass, and compound (1)-5 was added in an amount of 0.1% by mass.

[0598] [Chemical Formula 44]

[0599]

[0600] [Chemical Formula 45]

[0601]

[0602] As shown in the table below, dopants of other examples and comparative examples were prepared in the same manner as the dopant of the resin film 301A, except that the addition amounts of the ultraviolet absorber 1 and the ultraviolet absorber 2 were changed.

[0603] (3)Casting

[0604] The dopant was cast using a drum film machine. The core layer was co-cast from a die, with the surface layer dopant placed on top of the core layer dopant, and the gel was peeled off. The dopant was then placed in contact with a metal support cooled to -10°C. The drum was made of stainless steel.

[0605] (4) Drying

[0606] After the cast web (film) was peeled from the drum, it was conveyed, held at both ends with clamps, and dried in a tentering apparatus at 30-40°C for 20 minutes. The dried film was then framed and post-dried at 140°C. The drying temperature here refers to the film surface temperature.

[0607] (5) Coiling

[0608] Films having the compositions shown in the table below were produced. To assess their suitability for production, at least 24 rolls of 1280 mm in width and 2600 mm in length were produced under the above-described conditions. From one of the 24 continuously produced rolls, samples (1280 mm in width) with a long side of 1 m were cut out at 100 m intervals and subjected to various measurements. The resulting cellulose acylate films were used as resin films 301 to 309 in each of the Examples and Comparative Examples.

[0609] The absorbance of each of the resin films 301A to 309A produced above was measured using a spectrophotometer UV3600 (manufactured by Shimadzu Corporation).

[0610] The long-wavelength ultraviolet absorption capacity was evaluated by dividing the absorbance at a wavelength of 405 nm by the amount of ultraviolet absorber added (mass % relative to cellulose acylate). Values of 50 or greater were designated as A, 25 to 50 as B, and 25 or less as C. Larger values indicate higher long-wavelength ultraviolet absorption capacity. The results are shown in the "Long-wavelength Ultraviolet Absorption Capacity" column of the following table.

[0611] [Table 4]

[0612]

[0613] Compound (1)-5 used as the ultraviolet absorber 1 is a compound having the above structure. Furthermore, comparative compound 5 used as the ultraviolet absorber 2 is a compound having the following structure.

[0614] [Chemical Formula 46]

[0615]

[0616] The resin films 301A to 306A absorb light having a wavelength of approximately 400 nm more strongly than the resin films 307A to 309A, and are excellent in absorbing ultraviolet rays on the longer wavelength side.

[0617] (6) Preparation of polarizer

[0618] A polarizing plate was produced by the method shown below.

[0619] (6-1) Saponification treatment of resin film

[0620] 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. They were then washed in a water bath at room temperature (25°C) and neutralized with 0.05 mol / L sulfuric acid at 30°C. They were then washed again in a water bath at room temperature and dried with hot air at 100°C.

[0621] (6-2) Preparation of polarizer

[0622] A polyvinyl alcohol (PVA) film having a thickness of 80 μm was dyed by immersing it in an iodine aqueous solution having an iodine concentration of 0.05% by mass at 30°C for 60 seconds, then immersed in a boric acid aqueous solution having a boric acid concentration of 4% by mass for 60 seconds, stretched longitudinally to 5 times its original length, and dried at 50°C for 4 minutes to obtain a polarizer having a thickness of 19 μm.

[0623] (6-3) Fabrication of VA (Vertical Alignment) Retardation Film

[0624] As the retardation film, the following VA retardation film 1 or VA retardation film 2 was used.

[0625] (6-3-1) Preparation of VA Phase Difference Film 1

[0626] <Synthesis of Cycloolefin Polymer A>

[0627] 8-methoxycarbonyl-8-methyltetracyclo[4.4.0.1 2,5 .1 7,10 ] 72.5 parts by mass of 3-dodecene, 27.5 parts by mass of dicyclopentadiene, 5.6 parts by mass of 1-hexene as a molecular weight regulator, and 200 parts by mass of toluene were placed in a nitrogen-substituted reaction vessel and heated to 80°C. 0.18 ml of a toluene solution of triethylaluminum (0.6 mol / L) and 0.58 ml of a toluene solution of methanol-modified WCl6 (0.025 mol / L) were added thereto, and the mixture was reacted at 80°C for 3 hours to obtain a ring-opening polymer. Subsequently, the obtained solution of the ring-opening polymer was placed in an autoclave, and 200 parts by mass of toluene was further added. 2500 ppm of a hydrogenation catalyst RuHCl(CO)[P(C6H5)]3 was added relative to the amount of monomer added, the hydrogen pressure was set to 9-10 MPa, and the reaction was carried out at 160-165°C for 3 hours. After the reaction was completed, the mixture was precipitated in a large amount of methanol solution to obtain a hydrogenated ring-opening polymer (cycloolefin polymer A). The weight average molecular weight (Mw) of the hydrogenated ring-opening polymer obtained is 119×10 3 , molecular weight distribution (Mw / Mn) = 3.1.

[0628] <Preparation of fine particle dispersion>

[0629] 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 in a dissolver for 50 minutes, and then dispersed in a Manton-Gaulin to prepare a fine particle dispersion.

[0630] Preparation of microparticle additive solution

[0631] 4 parts by mass of cycloolefin polymer A was added to a dissolving tank containing 99 parts by mass of dichloromethane. After heating to completely dissolve the polymer, 11 parts by mass of the fine particle dispersion was gradually added while stirring thoroughly and dispersed using an attritor. The resulting mixture was filtered through a filter (Fine Met NF, manufactured by Nippon Seisen Co., Ltd.) to prepare a fine particle addition solution.

[0632] <Production of VA Retardation Film 1>

[0633] First, dichloromethane and methanol were added to a pressurized dissolution tank. Cycloolefin polymer A was placed in a pressurized dissolution tank to which a solvent was added while stirring. It was heated and completely dissolved while stirring to prepare a main dopant liquid. 2 parts by mass of a microparticle additive liquid were added to 100 parts by mass of the main dopant liquid, and the mixture was thoroughly mixed using an in-line mixer (TORAY static in-line mixer Hi-Mixer, SWJ). Then, a belt casting device was used to uniformly cast the mixture on a stainless steel belt support with a width of 2 m. Regarding the obtained web (film), the solvent was evaporated until the residual solvent content became 110% by mass and then peeled off from the stainless steel belt support. After peeling, tension was applied to stretch the film so that the longitudinal stretching ratio became 2%. Then, after drying the film until the residual solvent content became less than 1% by mass, it was further stretched by 35% at 165°C using a tenter in a direction perpendicular to the film conveying direction. In addition, the residual solvent content was calculated according to the following formula.

[0634] Residual solvent amount (mass %) = {(MN) / N} × 100

[0635] Here, M is the mass of the web at any time, and N is the mass of the web whose M has been measured when dried at 120° C. for 2 hours.

[0636] As described above, a VA retardation film 1 having a width of 1.5 m, a knurling pattern of 1 cm in width and 8 μm in height at the end, a film thickness of 35 μm, and an Rth of 121 nm was produced.

[0637] (6-3-2) Preparation of VA Phase Difference Film 2

[0638] Production of Cellulose Acylate

[0639] Cellulose acylates were synthesized using the methods described in Japanese Patent Application Laid-Open Nos. 10-045804 and 08-231761, and their acyl substitution degrees were measured. Specifically, sulfuric acid (7.8 parts by mass per 100 parts by mass of cellulose) was added as a catalyst, and carboxylic acid (acetic acid) as a raw material for the acyl groups was added, and an acylation reaction was carried out at 40°C. The degree of acyl (acetyl) substitution was adjusted by adjusting the amount of carboxylic acid. After acylation, the cellulose acylates were aged at 40°C. Furthermore, the cellulose acylates (cellulose acetates) were washed with acetone to remove low-molecular-weight components, thereby obtaining cellulose acylates having various average acyl substitution degrees.

[0640] <Synthesis of Additive A>

[0641] Additive A was synthesized by a method similar to or based on the method described in Japanese Patent No. 6095766. The structural formula of the synthesized compound is shown below.

[0642] [Chemical Formula 47]

[0643]

[0644] <Synthesis of Additive B>

[0645] Additive B was synthesized by a method similar to or based on the method described in International Publication No. 2015 / 005398. The structural formula of the synthesized compound is shown below.

[0646] [Chemical Formula 48]

[0647]

[0648] <Synthesis of Additive C>

[0649] Additive C was synthesized by a method similar to or based on the method described in Japanese Patent No. 4260332. The structural formula of the synthesized compound is shown below.

[0650] [Chemical Formula 49]

[0651]

[0652] <Preparation of dopant for core layer formation>

[0653] The following composition was placed in a mixing tank and stirred to dissolve the components, thereby preparing a dopant for forming a core layer.

[0654] (Composition of dopant for core layer formation)

[0655] Cellulose acetate (degree of substitution 2.4) 100.0 parts by mass

[0656] Additive A...12.0 parts by mass

[0657] Additive B ... 3.5 parts by mass

[0658] Additive C...1.0 part by mass

[0659] Dichloromethane 392.0 parts by mass

[0660] Methanol...58.5 parts by mass

[0661] <Preparation of dopant for skin layer formation>

[0662] The following composition was placed in a mixing tank and stirred to dissolve cellulose acetate, thereby preparing a dope for forming a skin layer.

[0663] (Composition of dopant for forming skin layer)

[0664] Cellulose acetate (degree of substitution 2.8) 100 parts by mass

[0665] Dichloromethane 440 parts by mass

[0666] Methanol...65.8 parts by mass

[0667] <Casting of VA Retardation Film 2>

[0668] The prepared core layer forming dopant and skin layer forming dopant were co-cast in three layers using a belt casting device to stack the skin layer, core layer, and skin layer in sequence. The film thickness of the core layer after drying was 39 μm, and the film thickness of each skin layer was 1 μm. The obtained film (mesh) was peeled off from the belt and clamped in a clamp. When the residual solvent amount was 20 to 5% by mass relative to the mass of the entire film, it was stretched transversely (stretched in the width direction) at a stretching ratio of 1.1 times at 140°C using a tenter. After that, the clamp was removed from the film, and after it was dried at 140°C for 20 minutes, it was further stretched transversely at a stretching ratio of 1.2 times at a Tg (glass transition temperature) of -3°C using a tenter, thereby producing a VA phase difference film 2. The film thickness of the obtained VA phase difference film 2 was 40 μm. In addition, "stretching ratio (%)" refers to the value obtained by the following formula.

[0669] Stretch ratio (%) = 100 × {(length after stretching) - (length before stretching)} / length before stretching. Tg is the temperature at which the loss tangent tanδ, determined by dynamic viscoelasticity measurement, reaches its maximum value. The loss tangent tanδ is determined by measuring E" (loss modulus) and E' (storage modulus) under the following conditions using a dynamic viscoelasticity measuring apparatus (DVA-200, manufactured by IT Measurement Control Co., Ltd.) on a film sample that has been pre-conditioned at 25°C and 60% relative humidity for at least 2 hours. Tanδ (=E" / E') and its maximum value are then calculated to determine Tg.

[0670] Device: DVA-200 manufactured by IT Measurement Control Co., Ltd.

[0671] Specimen: 5mm, length 50mm (gap 20mm)

[0672] Measurement conditions: tensile mode

[0673] Measuring temperature: -25℃~220℃

[0674] Heating conditions: 5℃ / min

[0675] Frequency: 1Hz

[0676] Furthermore, the amount of residual solvent was calculated according to the following formula.

[0677] Residual solvent amount (mass %) = {(MN) / N} × 100

[0678] M is the mass of the web at any time, and N is the mass of the web whose M was measured when dried at 120° C. for 2 hours.

[0679] (6-4) Preparation of VA Phase Difference Film 1 with Polarizer

[0680] <Preparation of UV-curable adhesive 1>

[0681] An ultraviolet curable adhesive was prepared using the composition shown below.

[0682] (Composition of UV-curable adhesive 1)

[0683] CELLOXIDE 2021P (Daicel Corporation, multifunctional epoxy compound) 100.0 parts by mass

[0684] RIKARESIN DME-100 (New Japan Chemical Co., Ltd., polyfunctional epoxy compound) 28.6 parts by mass

[0685] 2-Ethylhexyl glycidyl ether (monofunctional epoxy compound) 14.3 parts by mass

[0686] CPI-100P (photoacid generator, San-Apro Ltd.) 2.9 parts by mass

[0687] Irgacure 290 (photoacid generator, BASF Japan Ltd.) 5.7 parts by mass

[0688] 2-Isopropylthioxanthone (photoacid generator) 1.4 parts by mass

[0689] <Adhesion of VA Retardation Film 1 to Polarizer>

[0690] The VA retardation film 1 was attached to one side of a polarizer using an ultraviolet curable adhesive 1. After 5 seconds, ultraviolet rays were irradiated from the VA retardation film 1 side at an intensity of 200 mJ to cure the ultraviolet curable adhesive 1 to obtain a VA retardation film 1 with a polarizer.

[0691] (6-5-1) Manufacturing of Polarizing Plate 303B1

[0692] A polarizing plate 303B1 was prepared by attaching a saponified resin film 303A to the polarizer side of the VA phase difference film 1 with a polarizer using a polyvinyl alcohol-based adhesive.

[0693] (6-5-2) Manufacturing of Polarizer 303B2

[0694] A saponified resin film 303A was attached to one side of the polarizer using a polyvinyl alcohol-based adhesive, and a VA retardation film 2 was attached to the surface opposite to the surface attached with the resin film 303A, thereby producing a polarizing plate 303B2.

[0695] (6-6-1) Manufacturing of Liquid Crystal Display Devices 303C1, 304C1, and 308C1

[0696] The liquid crystal panel of a commercially available liquid crystal display device, the FlexScan 19-inch color liquid crystal display S1923-HBK (trade name, manufactured by EIZO Corporation), was removed, and the front polarizer was removed. In its place, the VA retardation film side of polarizer 303B1 was attached using an adhesive (SK-2057, manufactured by Soken Chemical & Engineering Co., Ltd.). This produced liquid crystal display device 303C1. As shown in the table below, liquid crystal display devices 304C1 and 308C1 were produced using the same method, except that the type of resin film was changed.

[0697] (6-6-2) Manufacturing of Liquid Crystal Display Devices 303C2, 304C2, and 308C2

[0698] The liquid crystal panel of a commercially available liquid crystal display device, the FlexScan 19-inch color liquid crystal display S1923-HBK (trade name, manufactured by EIZO Corporation), was removed, and the front polarizer was removed. In its place, the VA retardation film side of polarizer 303B2 was attached using an adhesive (SK-2057, manufactured by Soken Chemical & Engineering Co., Ltd.). This produced liquid crystal display device 303C2. As shown in the table below, liquid crystal display devices 304C2 and 308C2 were produced using the same method, except that the type of resin film was changed.

[0699] [Table 5]

[0700] Liquid crystal display device No. Polarizer No. Resin film No. VA retardation film No. Figure No. 303C1 303B1 303A 1 Figure 1 304C1 304B1 304A 1 Figure 1 308C1 308B1 308A 1 Figure 1 303C2 303B2 303A 2 Figure 1 304C2 304B2 304A 2 Figure 1 308C2 308B2 308A 2 Figure 1

[0701] The liquid crystal display devices 303C1, 303C2, 304C1, and 304C2 including the ultraviolet absorber of the present invention are preferred because they exhibit less change in image quality during long-term display than the liquid crystal display devices 308C1 and 308C2.

[0702] (7) Fabrication of organic electroluminescent display devices

[0703] An organic electroluminescent display device was produced by the method shown below.

[0704] (7-1) Preparation of Optically Anisotropic Layer A

[0705] (Preparation of Cellulose Acylate Solution)

[0706] The following composition was placed in a mixing tank and stirred while heating to dissolve the components, thereby preparing a cellulose acylate solution.

[0707] (Composition of Cellulose Acylate Solution)

[0708] Cellulose acetate (acetylation degree 2.86) 100 parts by mass

[0709] Dichloromethane (first solvent) 320 parts by mass

[0710] Methanol (second solvent) 83 parts by mass

[0711] 1-Butanol (third solvent) 3 parts by mass

[0712] Triphenyl phosphate...7.6 parts by mass

[0713] Biphenyl diphenyl phosphate... 3.8 parts by mass

[0714] (Preparation of Matting Agent Dispersion)

[0715] The following composition was placed in a dispersing machine and stirred to dissolve the components, thereby preparing a matting agent dispersion.

[0716] (Composition of Matting Agent Dispersion)

[0717] Silica particle dispersion (average particle size 16 nm, AEROSIL R972, manufactured by Nippon Aerosil Co., Ltd.) 10.0 parts by mass

[0718] Dichloromethane...72.8 parts by mass

[0719] Methanol...3.9 parts by mass

[0720] Butanol...0.5 parts by mass

[0721] Cellulose acylate solution: 0.3 parts by mass

[0722] (Preparation of UV Absorber Solution)

[0723] The following composition was placed in a mixing tank and stirred while heating to dissolve the components, thereby preparing an ultraviolet absorbent solution.

[0724] (Composition of UV absorber solution)

[0725] Ultraviolet absorber (compound having a structure represented by formula (UV-11)) 10.0 parts by mass

[0726] Ultraviolet absorber (compound having a structure represented by formula (UV-12)) 10.0 parts by mass

[0727] Dichloromethane 55.7 parts by mass

[0728] Methanol...10 parts by mass

[0729] Butanol...1.3 parts by mass

[0730] Cellulose acylate solution: 12.9 parts by mass

[0731] [Chemical Formula 50]

[0732]

[0733] (Production of Cellulose Acylate Film)

[0734] To a mixture of 94.6 parts by mass of cellulose acylate solution and 1.3 parts by mass of a matting agent dispersion, an ultraviolet absorber solution was added so that the ultraviolet absorber (UV-1) and the ultraviolet absorber (UV-2) were each 1.0 part by mass per 100 parts by mass of cellulose acylate, and the mixture was stirred thoroughly while heating to dissolve the components, thereby preparing a dopant. The obtained dopant was heated to 30°C and cast on a mirror-finished stainless steel support having a diameter of 3m through a casting die. The surface temperature of the mirror-finished stainless steel support was set to -5°C, and the coating width was set to 1470mm. By heating the dopant on the drum at a speed of 150m 3 / minute, the cast dopant film was dried by blowing dry air at 34°C, and peeled from the drum in a state where the residual solvent was 150%. During the peeling, it was stretched 15% in the conveying direction (longitudinal direction). After that, it was stretched using a pin tenter (Japanese Patent Publication No. 04-001009). Figure 3 The film was conveyed while being held at both ends in the width direction (orthogonal to the casting direction) using a pin tenter (described in [ 1 ]). No stretching treatment was performed in the width direction. Furthermore, the film was conveyed between rollers of a heat treatment apparatus for further drying, thereby producing a cellulose acylate film (T1). The produced long cellulose acylate film (T1) had a residual solvent content of 0.2%, a thickness of 60 μm, and Re (in-plane retardation) and Rth (retardation in the thickness direction) at a wavelength of 550 nm of 0.8 nm and 40 nm, respectively.

[0735] (Alkali saponification treatment)

[0736] The cellulose acylate film (T1) was passed through a dielectric heating roller at a temperature of 60°C, and the film surface temperature was raised to 40°C. The film was then coated with a bar coater at a temperature of 14 ml / m 2 The following alkaline solution was applied to the tape surface of the film. The cellulose acylate film coated with the alkaline solution was then passed under a steam-type far-infrared heater manufactured by NORITAKE CO., LIMITED and heated to 110°C for 10 seconds. 3 ml / m² of the obtained film was then applied using a bar coater. 2 The obtained film was then subjected to three repetitions of water washing with a fountain coater and water removal with an air knife, and then dried by passing through a drying zone at 70°C for 10 seconds to prepare an alkali saponified cellulose acylate film.

[0737] (Composition of alkaline solution)

[0738] Potassium hydroxide 4.7 parts by mass

[0739] Water...15.8 parts by mass

[0740] Isopropyl alcohol...63.7 parts by mass

[0741] Surfactant SF-1(C 14 H 29 O(CH2CH2O) 20 H) 1.0 part by mass

[0742] Propylene glycol...14.8 parts by mass

[0743] (Formation of Orientation Film)

[0744] The alkali-saponified surface of a cellulose acylate film (T1) was continuously coated with an alignment film coating solution having the following composition using a #14 wire bar coater. The film coated with the alignment film coating solution was dried with hot air at 60°C for 60 seconds and then with hot air at 100°C for 120 seconds to form an alignment film. The modified polyvinyl alcohol used had a saponification degree of 88%.

[0745] (Composition of Alignment Film Coating Liquid)

[0746] 10 parts by mass of modified polyvinyl alcohol having the following structure

[0747] Water...308 parts by mass

[0748] Methanol...70 parts by mass

[0749] Isopropyl alcohol...29 parts by mass

[0750] Photopolymerization initiator (Omnirad 2959, manufactured by IGM Resins BV) 0.8 parts by mass

[0751] [Chemical Formula 51]

[0752]

[0753] (Formation of Optically Anisotropic Layer A)

[0754] The oriented film produced above was continuously subjected to a friction treatment. At this time, the long side direction of the long strip of film was parallel to the conveying direction, and the angle between the long side direction of the film (conveying direction) and the rotation axis of the friction roller was set to 72.5° (if the long side direction of the film (conveying direction) is set to 90°, when viewed from the oriented film side, with the width direction of the film as the reference (0°), and the counterclockwise rotation direction represented by a positive value, the rotation axis of the friction roller is at -17.5°.) In other words, the position of the rotation axis of the friction roller corresponds to the position of 72.5° counterclockwise rotation based on the long side direction of the film.).

[0755] The optically anisotropic coating liquid (A) containing the discotic liquid crystal (DLC) compound of the following composition was continuously coated on the oriented film prepared above using a #5.0 wire bar coater. The film conveying speed (V) was set to 26 m / min. In order to dry the solvent of the coating liquid and mature the orientation of the discotic liquid crystal compound (DLC compound), it was dried with hot air at 115°C for 90 seconds, then with hot air at 80°C for 60 seconds, and then the obtained coating film was irradiated with UV (ultraviolet light) at 80°C (exposure: 70 mJ / cm 2 ), thereby fixing the orientation of the liquid crystal compound. The thickness of the optically anisotropic layer A is 2.0 μm. It was confirmed that the average tilt angle of the disk surface of the DLC compound relative to the film surface was 90°, and the DLC compound was oriented perpendicular to the film surface. In addition, the angle of the slow axis is parallel to the rotation axis of the friction roller. If the long side direction (transmission direction) of the film is set to 90° (the width direction of the film is set to 0°. When observed from the oriented film side, the counterclockwise direction is expressed as a positive value with the width direction of the film as the reference (0°).), the angle of the slow axis is -17.5°. The obtained optically anisotropic layer A conforms to the λ / 2 plate, and the Re and Rth at a wavelength of 550 nm are Re (550): 238 nm, Rth (550): -119 nm, respectively.

[0756] (Composition of Optically Anisotropic Layer Coating Liquid (A))

[0757] The following discotic liquid crystal compound (A) 80 parts by mass

[0758] The following discotic liquid crystal compound (B) 20 parts by mass

[0759] Ethylene oxide-modified trimethylolpropane acrylate (V#360, manufactured by OSAKA ORGANIC CHEMICAL INDUSTRY LTD) 5 parts by mass

[0760] Photopolymerization initiator (Omnirad 907, manufactured by IGM Resins BV) ... 4 parts by mass

[0761] The following pyridinium salt (A) ... 2 parts by mass

[0762] The following polymer (A) ... 0.2 parts by mass

[0763] The following polymer (B) ... 0.1 parts by mass

[0764] The following polymer (C) ... 0.1 parts by mass

[0765] Methyl ethyl ketone... 211 parts by mass

[0766] [Chemical Formula 52]

[0767]

[0768] Polymer A: Resin with the following structure

[0769] [Chemical Formula 53]

[0770]

[0771] Polymer B: A resin having the following structure (In the structural formula, a represents 90 and b represents 10.)

[0772] [Chemical Formula 54]

[0773]

[0774] Polymer C: Resin with the following structure

[0775] [Chemical Formula 55]

[0776]

[0777] (7-2) Preparation of Optically Anisotropic Layer B

[0778] (Formation of Optically Anisotropic Layer B)

[0779] Following the same steps as above (production of optically anisotropic layer A), an oriented film was formed on the cellulose acylate film (T1), and the oriented film was continuously subjected to a rubbing treatment. At this time, the long side of the long film was parallel to the transport direction, and the angle between the long side of the film (the transport direction) and the rotation axis of the rubbing roller was set to 102.5° (if the long side of the film (the transport direction) is set to 90°, when viewed from the oriented film side, with the film width direction as the reference, and the counterclockwise rotation direction is expressed as a positive value, the rotation axis of the rubbing roller is located at 12.5°. In other words, the position of the rotation axis of the rubbing roller corresponds to the position of 102.5° rotated counterclockwise with respect to the long side of the film.).

[0780] The optically anisotropic layer coating liquid (B) containing the discotic liquid crystal compound of the following composition was continuously coated on the rubbing-treated alignment film using a #2.8 wire bar coater. The film conveying speed (V) was set to 26 m / min. In order to dry the solvent of the coating liquid and mature the orientation of the discotic liquid crystal compound, it was heated with hot air at 60°C for 60 seconds. After that, the obtained coating film was UV irradiated at 60°C, thereby fixing the orientation of the discotic liquid crystal compound. The thickness of the optically anisotropic layer B was 0.8 μm. It was confirmed that the average tilt angle of the long axis of the discotic liquid crystal compound relative to the film surface was 90°, and the discotic liquid crystal compound was oriented perpendicular to the film surface. In addition, the angle of the slow axis was orthogonal to the rotation axis of the rubbing roller. If the long side direction of the film was set to 90° (the width direction of the film was set to 0°. When viewed from the alignment film side, the width direction of the film was used as the reference (0°), and the counterclockwise direction was expressed as a positive value.), the angle of the slow axis was 102.5° (-77.5°). The obtained optically anisotropic layer B conformed to a λ / 4 plate, and had Re(550) of 118 nm and Rth(550) of -59 nm.

[0781] (Composition of Optically Anisotropic Layer Coating Liquid (B))

[0782] 80 parts by mass of the above-mentioned discotic liquid crystal compound (A)

[0783] 20 parts by mass of the above-mentioned discotic liquid crystal compound (B)

[0784] Ethylene oxide-modified trimethylolpropane acrylate (V#360, manufactured by OSAKA ORGANIC CHEMICAL INDUSTRY LTD) 10 parts by mass

[0785] Photopolymerization initiator (Omnirad 907, manufactured by IGM Resins BV) 5 parts by mass

[0786] 1 part by mass of the pyridinium salt (A)

[0787] The above polymer (A) ... 0.2 parts by mass

[0788] The above polymer (B) ... 0.1 parts by mass

[0789] The above polymer (C) ... 0.1 parts by mass

[0790] Methyl ethyl ketone...348 parts by mass

[0791] (7-3) Saponification treatment of resin film

[0792] The resin films 303A, 304A, and 308A prepared above were immersed in a 2.3 mol / L sodium hydroxide aqueous solution at 55°C for 3 minutes. They were then washed in a room temperature (25°C) water bath and neutralized with 0.05 mol / L sulfuric acid at 30°C. They were then washed again in a room temperature water bath and dried with hot air at 100°C.

[0793] (7-4) Preparation of polarizer

[0794] A polyvinyl alcohol (PVA) film having a thickness of 80 μm was dyed by immersing it in an iodine aqueous solution having an iodine concentration of 0.05% by mass at 30°C for 60 seconds, then immersed in a boric acid aqueous solution having a boric acid concentration of 4% by mass for 60 seconds, stretched longitudinally to 5 times its original length, and dried at 50°C for 4 minutes to obtain a polarizer having a thickness of 19 μm.

[0795] The saponified resin film 303A was attached to one side of the polarizer produced above using a polyvinyl alcohol-based adhesive, thereby producing a polarizing plate.

[0796] (7-5) Manufacturing of Circular Polarizer 303D

[0797] An adhesive (SK-2057, manufactured by Soken Chemical & Engineering Co., Ltd.) was applied to the polarizer side (without the resin film 303A) of the polarizing plate produced above to form an adhesive layer. The cellulose acylate film, the oriented film, and the film having the optically anisotropic layer A produced above were then laminated together so that the adhesive layer and the optically anisotropic layer A were in close contact. The cellulose acylate film and the oriented film were then peeled off to obtain a laminate. Next, an adhesive (SK-2057, manufactured by Soken Chemical & Engineering Co., Ltd.) was applied to the optically anisotropic layer A in the laminate obtained to form an adhesive layer. Next, the laminate provided with the adhesive layer was laminated together with the cellulose acylate film, the oriented film, and the film having the optically anisotropic layer B produced above so that the adhesive layer and the optically anisotropic layer B were in close contact. The cellulose acylate film and the oriented film were then peeled off. Through the above steps, a circular polarizing plate 303D was produced, which was configured in this order with a polarizer, an optically anisotropic layer A (λ / 2 plate), and an optically anisotropic layer B (λ / 4 plate). Furthermore, when viewed from the polarizer side, with the transmission axis of the polarizer as the reference (0°), and the counterclockwise direction expressed as positive values, the slow axis angle of the λ / 2 plate was -17.5°, and the slow axis angle of the λ / 4 plate was -77.5°. In other words, the slow axis of the optically anisotropic layer A (λ / 2 plate) formed an angle of 17.5° with the transmission axis of the polarizer, and the slow axis of the optically anisotropic layer A (λ / 2 plate) formed an angle of 60° with the slow axis of the optically anisotropic layer B (λ / 4 plate).

[0798] (7-6) Manufacturing of Organic Electroluminescent Display Devices 303E, 304E, and 308E

[0799] The touch panel with a circular polarizer was peeled off from a commercially available organic electroluminescent display device, the GALAXY S5 (trade name, manufactured by SAMSUNG), and the circular polarizer was further peeled off from the touch panel, thereby separating the organic electroluminescent display element, touch panel, and circular polarizer. The separated touch panel and organic electroluminescent display element were then laminated together again, and the circular polarizer 303E, prepared above, was laminated to the touch panel to prevent air from entering, thereby producing an organic electroluminescent display device. As shown in Table 3, liquid crystal display devices 304E and 308E were manufactured using the same method, except for changing the type of resin film.

[0800] [Table 6]

[0801] Organic electroluminescent display device No Circular polarizer No. Resin film No. Figure No. 303E 303D 303A Figure 11 304E 304D 304A Figure 11 308E 308D 308A Figure 11

[0802] Compared to the organic electroluminescent display device 308E, the organic electroluminescent display devices 303E and 304E including the ultraviolet absorber of the present invention are preferred because they have less change in image quality during long-term display.

[0803] <Test Example 4>

[0804] The optical film 401A was formed on the base film by the method described below to produce the peelable laminated film 401B.

[0805] (1) Preparation of coating liquid

[0806] A coating liquid 1 for forming the optical film 401A was prepared with the following composition. The obtained coating liquid was filtered using a filter having an absolute filtration accuracy of 5 μm.

[0807] (Composition of coating liquid 1)

[0808] AS-70 (acrylonitrile / styrene copolymer resin, manufactured by NIPPON STEEL Chemical & Material Co., Ltd.) 100.0 parts by mass

[0809] Byron 500 (polyester resin, manufactured by TOYOBO CO., LTD.) 0.9 parts by mass

[0810] SMA2000P (styrene / maleic acid copolymer, KAWAHARA PETROCHEMICAL CO., LTD) 4.2 parts by mass

[0811] Surfactant 1...0.1 parts by mass

[0812] Ultraviolet absorber (compound (1)-5) 3.1 parts by mass

[0813] Ultraviolet absorber (comparative compound 5) ... 0.0 parts by mass

[0814] Methyl acetate...255.1 parts by mass

[0815] Acetonitrile...229.6 parts by mass

[0816] Ethanol...25.5 parts by mass

[0817] Surfactant 1: Compound with the following structure

[0818] [Chemical Formula 56]

[0819]

[0820] Compound (1)-5 used as an ultraviolet absorber and comparative compound 5 have the above-mentioned structures.

[0821] As shown in the following table, coating solutions 2 to 6 were prepared in the same manner as coating solution 1 except that the addition amounts of compound (1)-5 and comparative compound 5 were changed.

[0822] (2) Coating of peelable laminated film

[0823] A commercially available polyethylene terephthalate film (EMBLET S38, 38 μm thick, short-wave absorption edge wavelength 310 nm, manufactured by UNITIKA LTD) was used as a substrate film. Coating solutions 1 to 6 were used to produce optical films 401A to 406A with a thickness of 5 μm, thereby obtaining peelable laminated films (43 μm thick, short-wave absorption edge wavelength 310 nm). Specifically, coating solution 1 was applied to the substrate film at a conveyor speed of 30 m / min using the slot die coating method described in Example 1 of Japanese Patent Application Laid-Open No. 2006-122889, and dried at 105°C for 30 seconds. The film was then wound up. The resulting peelable laminated films were used as peelable laminated films 401B to 406B in each of the Examples and Comparative Examples.

[0824] The absorbance of each of the releasable laminated films 401B to 406B prepared above was measured using a spectrophotometer UV3600 (manufactured by Shimadzu Corporation). The absorbance at a wavelength of 405 nm was divided by the amount of UV absorber added (mass % relative to AS-70). The long-wavelength UV absorption capacity was evaluated by dividing the absorbance at a wavelength of 405 nm by the amount of UV absorber added (mass % relative to AS-70). Values of 50 or greater were assigned as A, 25 to 50 as B, and 25 or less as C. Larger values indicate higher long-wavelength UV absorption capacity. The results are shown in the "Long-wavelength UV absorption capacity" column in the table below.

[0825] [Table 7]

[0826]

[0827] The releasable laminated films 401B to 403B absorb light having a wavelength of approximately 400 nm more strongly than the releasable laminated films 404B to 406B, and are excellent in absorbing ultraviolet rays on the longer wavelength side.

[0828] (3) Production of polarizer

[0829] A polarizing plate was produced by the method shown below.

[0830] (3-1) Saponification treatment of polarizer protective film

[0831] A 60 μm triacetylcellulose 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. The film was then washed in a room temperature (25°C) water bath and neutralized with 0.05 mol / L sulfuric acid at 30°C. The film was then washed again in a room temperature water bath and dried with hot air at 100°C.

[0832] (3-2-1) Production of Polarizing Plate 4C1

[0833] A polarizing plate 4C1 was produced by the same method as that of the polarizing plate 303B1 except that the above-mentioned 60-μm triacetyl cellulose film was used instead of the resin film 303A.

[0834] (3-2-2) Manufacturing of Polarizer 4C2

[0835] A polarizing plate 4C2 was produced by the same method as that of the polarizing plate 303B2 except that the above-mentioned 60-μm triacetyl cellulose film was used instead of the resin film 303A.

[0836] (3-3-1) Production of Polarizing Plate 402D1 with Releasable Laminated Film

[0837] After the optical film side of the releasable laminated film 402 is bonded to the VA phase difference film side of the polarizer 4C-1 by the ultraviolet curing adhesive 1, ultraviolet rays are irradiated at an intensity of 200mJ to cure the ultraviolet curing adhesive 1 to form a polarizer 402D1 with a releasable laminated film.

[0838] (3-3-2) Production of Polarizing Plate 402D2 with Releasable Laminated Film

[0839] After the optical film side of the releasable laminated film 402 is bonded to the VA phase difference film side of the polarizer 4C-2 by the ultraviolet curing adhesive 1, ultraviolet rays are irradiated at an intensity of 200mJ to cure the ultraviolet curing adhesive 1 to form a polarizer 402D2 with a releasable laminated film.

[0840] (3-4) Manufacturing of Liquid Crystal Display Devices 402E1, 405E1, 402E2, and 405E2

[0841] After peeling EMBLET S38 from polarizer 402D1 to expose the optical film, the liquid crystal panel of a commercially available liquid crystal display device, a FlexScan 19-inch color liquid crystal display S1923-HBK (trade name, manufactured by EIZO Corporation), was removed. The front polarizer was peeled off and replaced with the optical film side of polarizer 402D1 using an adhesive (SK-2057, manufactured by Soken Chemical & Engineering Co., Ltd.). In this manner, liquid crystal display device 402E1 was manufactured. As shown in the table below, liquid crystal display devices 405E1, 402E2, and 405E2 were manufactured using the same method, except that the type of polarizer with a releasable laminated film was changed.

[0842] [Table 8]

[0843] Liquid crystal display device No. Polarizing plate with peelable laminated film No. Polarizer No. Peelable laminated film No. Figure No. 402E1 402D1 4C1 402A Figure 5 405E1 405D1 4C1 405A Figure 5 402E2 402D2 4C2 402A Figure 5 405E2 405D2 4C2 405A Figure 5

[0844] The liquid crystal display devices 402E1 and 402E2 containing the ultraviolet absorber of the present invention are preferred because they have less change in image quality during long-term display than the liquid crystal display devices 405E1 and 405E2.

[0845] <Test Example 5>

[0846] The adhesive 501 was produced by the method shown below.

[0847] (1) Preparation of coating liquid

[0848] (Composition of coating liquid 1)

[0849] Acrylic resin (SK Dyne-SF2147) 100.0 parts by mass

[0850] Polymerizable compound (TD-75) 0.04 parts by mass

[0851] Silane coupling agent (A-50) 0.06 parts by mass

[0852] Ultraviolet absorber (compound (1)-5) 0.2 parts by mass

[0853] Ultraviolet absorber (comparative compound 5) ... 0.0 parts by mass

[0854] The materials used are shown below: Compound (1)-5 and Comparative Compound 5 used as ultraviolet absorbers have the above-mentioned structures.

[0855] SK Dyne-SF2147: Acrylate copolymer. Solid content concentration 10-20% by mass, ethyl acetate, butyl acrylate solvent (Soken Chemical & Engineering Co., Ltd.)

[0856] TD-75: Trimethylolpropane-based toluene diisocyanate (Soken Chemical & Engineering Co., Ltd.)

[0857] A-50: Organosilane (Soken Chemical & Engineering Co., Ltd.)

[0858] As shown in the following table, coating solutions 2 to 6 were prepared in the same manner as coating solution 1 except that the addition amounts of compound (1)-5 and comparative compound 5 were changed.

[0859] (2) Preparation of adhesive sheet

[0860] The above-described coating solutions 1 to 6 were applied to the release-treated surface of a polyethylene terephthalate film (manufactured by Fujimoto Co., Ltd., MASTACK AS3-310, hereinafter referred to as the separator) using an applicator to a thickness of 35 μm after drying. The film was then dried at 110°C for 3 minutes. The film was then bonded to the release-treated surface of the separator and humidity was adjusted at 25°C and 60% for 24 hours to produce adhesive sheets 501A to 506A.

[0861] (3) Preparation of glass bonding adhesive

[0862] The diaphragms of adhesive sheets 501A to 506A were peeled off and bonded to EAGLE glass with a thickness of 1.1 mm, thereby producing glass bonding adhesives 501B to 506B. The absorbance of each of the glass bonding adhesives 501B to 506B produced above was measured using a spectrophotometer UV3600 (manufactured by Shimadzu Corporation). Furthermore, the absorbance at a wavelength of 405 nm was divided by the amount of UV absorber added (mass % relative to SK Dyne-SF2147). The absorbance at a wavelength of 405 nm was divided by the amount of UV absorber added (mass % relative to SK Dyne-SF2147). The absorbance at a wavelength of 50 or more was set as A, the absorbance at a wavelength of 25 to 50 was set as B, and the absorbance at a wavelength of 25 or less was set as C to evaluate the long-wavelength UV absorption capacity. The larger the value, the higher the long-wavelength UV absorption capacity. The results are shown in the long-wavelength UV absorption capacity column of the table below.

[0863] [Table 9]

[0864]

[0865] The releasable laminated films 501B to 503B absorb light having a wavelength of approximately 400 nm more strongly than the releasable laminated films 504B to 506B, and are excellent in absorbing ultraviolet rays on the longer wavelength side.

[0866] (4) Manufacturing of Liquid Crystal Display Devices 502C1, 505C1, 502C2, and 505C2

[0867] The liquid crystal panel of a commercially available liquid crystal display device, the FlexScan 19-inch color liquid crystal display S1923-HBK (trade name, manufactured by EIZO Corporation), was removed, and the polarizer on the backlight side was removed. In its place, the VA retardation film side of the polarizer 4C1 was attached via an adhesive sheet 502A. This produced liquid crystal display device 502C1. Liquid crystal display devices 505C1, 502C2, and 505C2 were also produced using the same method, except for varying the types of adhesive sheets and polarizers.

[0868] [Table 10]

[0869] Liquid crystal display device No. Polarizer No. Adhesive sheet No. Figure No. 502C1 4C1 502A Figure 8 505C1 4C1 505A Figure 8 502C2 4C2 502A Figure 8 505C2 4C2 505A Figure 8

[0870] The liquid crystal display devices 502C1 and 502C2 containing the ultraviolet absorber of the present invention are preferred because they have less change in image quality during long-term display than the liquid crystal display devices 505C1 and 505C2.

[0871] Explanation of symbols

[0872] 1-10 - Liquid crystal display device, 11-13 - Organic electroluminescent display device, 22, 49, 176 - Polarizer protective film containing the ultraviolet absorber of the present invention, 56, 75 - Inner protective film (retardation film) containing the ultraviolet absorber of the present invention, 88, 107, 206 - Optical component (optical film) containing the ultraviolet absorber of the present invention, 121, 138, 194 - Binder or adhesive containing the ultraviolet absorber of the present invention, 145, 174 - Functional layer containing the ultraviolet 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 layer, 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, 1 55, 157, 162, 164, 166, 168, 170, 172, 177, 179, 181, 183, 188, 190, 192, 199, 201, 203, 205, 207- adhesive or binder, 24, 32, 39, 47, 54, 62, 69, 77, 84, 94, 101, 111, 118, 126, 133, 141, 148, 156, 163, 171, 178, 189, 200- polarizer, 26, 30, 41, 45, 56, 60, 71, 75, 86, 92, 103, 109, 120, 124, 135, 139, 150, 154, 165, 169-phase difference film, 28, 43, 58, 73, 90, 105, 122, 137, 152, 167-liquid crystal unit, 34, 37, 52, 64, 67, 79, 82, 96, 99, 113, 116, 128, 131, 143, 146, 158, 161, 173, 187, 198-polarizer protective film, 180, 191, 202-2 / λ plate, 182, 193, 204-4 / λ plate, 184, 195, 208-touch panel, 185, 196, 209-organic electroluminescent element.

Claims

1. A resin composition comprising a compound represented by formula (1) and a resin; In formula (1), R 1 and R 2 each independently represents an alkyl group having 1 to 8 carbon atoms or an aryl group having 6 to 12 carbon atoms, R 3 and R 6 each independently represents an alkoxy group having 1 to 10 carbon atoms or an acyloxy group having 2 to 10 carbon atoms, R 4 represents an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 12 carbon atoms, or an alkoxy group having 1 to 8 carbon atoms, R 5 represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms; in, R 3 and R 6 When each independently represents an acyloxy group having 2 to 10 carbon atoms, R 4 It is an alkoxy group having 1 to 8 carbon atoms.

2. The resin composition according to claim 1, wherein In formula (1), R 3 and R 6 At least one of them is an alkoxy group.

3. The resin composition according to claim 1, wherein The compound represented by the formula (1) is a compound represented by the following formula (1a); In formula (1a), R 1a and R 2a Each independently represents an alkyl group having 1 to 8 carbon atoms, R 3a and R 6a each independently represents an alkoxy group having 1 to 10 carbon atoms or an acyloxy group having 2 to 10 carbon atoms, R 4a represents an alkyl group having 1 to 8 carbon atoms or an alkoxy group having 1 to 8 carbon atoms, R 5a represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms; Among them, R 3a and R 6a When it is an acyloxy group having 2 to 10 carbon atoms, R 4a It is an alkoxy group having 1 to 8 carbon atoms.

4. The resin composition according to claim 1 or 2, further comprising a compound represented by formula (2); In formula (2), R 11 and R 12 each independently represents an alkyl group having 1 to 8 carbon atoms or an aryl group having 6 to 12 carbon atoms, R 13 and R 16 Each independently represents a hydroxyl group, an alkoxy group having 1 to 10 carbon atoms, or an acyloxy group having 2 to 10 carbon atoms, R 14 represents an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 12 carbon atoms, or an alkoxy group having 1 to 8 carbon atoms, R 15 represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms; in, R 13 and R 16 At least one of them is a hydroxyl group. 5 . The resin composition according to claim 1 , further comprising an ultraviolet absorber other than the compound represented by the formula (1).

6. The resin composition according to claim 1 or 2, wherein The resin is at least one selected from the group consisting of (meth)acrylic resin, polystyrene resin, polyester resin, polyurethane resin, polythiocarbamate resin, polyimide resin, epoxy resin, polycarbonate resin and cellulose acylate resin. 7 . A cured product obtained by using the resin composition according to claim 1 .

8. An ultraviolet absorber comprising a compound represented by formula (1); In formula (1), R 1 and R 2 each independently represents an alkyl group having 1 to 8 carbon atoms or an aryl group having 6 to 12 carbon atoms, R 3 and R 6 each independently represents an alkoxy group having 1 to 10 carbon atoms or an acyloxy group having 2 to 10 carbon atoms, R 4 represents an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 12 carbon atoms, or an alkoxy group having 1 to 8 carbon atoms, R 5 represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms; in, R 3 and R 6 When each independently represents an acyloxy group having 2 to 10 carbon atoms, R 4 It is an alkoxy group having 1 to 8 carbon atoms.

9. The ultraviolet absorber according to claim 8, further comprising a compound represented by formula (2); In formula (2), R 11 and R 12 each independently represents an alkyl group having 1 to 8 carbon atoms or an aryl group having 6 to 12 carbon atoms, R 13 and R 16 Each independently represents a hydroxyl group, an alkoxy group having 1 to 10 carbon atoms, or an acyloxy group having 2 to 10 carbon atoms, R 14 represents an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 12 carbon atoms, or an alkoxy group having 1 to 8 carbon atoms, R 15 represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms; in, R 13 and R 16 At least one of them is a hydroxyl group. 10 . An ultraviolet cut filter comprising the ultraviolet absorber according to claim 8 .

11. A lens comprising the ultraviolet absorber according to claim 8 or 9.

12. A protective material comprising the ultraviolet absorber according to claim 8 or 9.

13. A compound represented by formula (1a), wherein In formula (1a), R 1a and R 2a Each independently represents an alkyl group having 1 to 8 carbon atoms, R 3a and R 6a each independently represents an alkoxy group having 1 to 10 carbon atoms or an acyloxy group having 2 to 10 carbon atoms, R 4a represents an alkyl group having 1 to 8 carbon atoms or an alkoxy group having 1 to 8 carbon atoms, R 5a represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms; Among them, R 3a and R 6a When it is an acyloxy group having 2 to 10 carbon atoms, R 4a It is an alkoxy group having 1 to 8 carbon atoms.

14. A method for synthesizing a compound represented by formula (1a), comprising reacting a compound represented by formula (2a) with a halogenated alkyl compound or a carboxylic acid halide; In formula (1a), R 1a and R 2a Each independently represents an alkyl group having 1 to 8 carbon atoms, R 3a and R 6a each independently represents an alkoxy group having 1 to 10 carbon atoms or an acyloxy group having 2 to 10 carbon atoms, R 4a represents an alkyl group having 1 to 8 carbon atoms or an alkoxy group having 1 to 8 carbon atoms, R 5a represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms; in, R 3a and R 6a When it is an acyloxy group having 2 to 10 carbon atoms, R 4a is an alkoxy group having 1 to 8 carbon atoms; In formula (2a), R 11a and R 12a Each independently represents an alkyl group having 1 to 8 carbon atoms, R 14a represents an alkyl group having 1 to 8 carbon atoms or an alkoxy group having 1 to 8 carbon atoms, R 15a It represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms.

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