Composition, cured product or molded body, optical member, and lens

Abstract

This invention provides a composition containing component A and component B, a cured product or molded article thereof, an optical component, and a lens. Component A: a compound containing a nitrogen-fused aromatic ring as a partial structure; Component B: a compound represented by any one of the following general formulas (B1) to (B5). In the above formulas, Ar... 101 ~Ar 104 X represents aryl or heteroaryl. 1 Y represents a monovalent substituent. 1 This indicates a hydrogen atom or a monovalent substituent. Ar 101 ~Ar 104 X 1 and Y 1 Two adjacent elements in the loop can bond together to form a ring. Among them, the element that can serve as X... 1 Or Y 1 The monovalent substituents used are not aryl or heteroaryl.

Description

Technical Field

[0001] This invention relates to a composition, a cured product or molded body, an optical component, and a lens. Background Technology

[0002] Previously, glass materials were used in the optical components of camera modules in cameras, camcorders, or mobile phones, videophones, or walkie-talkies with cameras. Glass is preferred due to its various optical properties and excellent environmental resistance; however, it also suffers from drawbacks such as difficulty in weight reduction or miniaturization, and poor processability and productivity. In contrast, cured resins can be mass-produced and have excellent processability, thus they have been increasingly used in various optical components in recent years.

[0003] In recent years, the miniaturization of camera modules has necessitated the miniaturization of optical components used in these modules. However, miniaturization of optical components introduces chromatic aberration problems. Therefore, this study investigated how to correct chromatic aberration in optical components using resin-cured materials by adjusting the Abbe number through monomers or additives in the curing composition.

[0004] Polycyclic fused-ring compounds containing nitrogen atoms among the atoms constituting the fused rings are being developed as materials for optical components used in imaging modules, exhibiting low Abbe number νd (wavelength dispersion characteristic of refractive index) or high F-value (θg, partial dispersion ratio). For example, Patent Document 1 describes a thermoplastic resin having structural units containing polycyclic fused rings in which nitrogen atoms are present among the atoms constituting the fused rings.

[0005] On the other hand, since the optical components of the camera module are used in outdoor light environments, it is also important to suppress the coloration of the cured material (i.e., the decrease in transmittance) (hereinafter also referred to as "lightfastness") that occurs during long-term use and storage in outdoor light environments.

[0006] In previous studies by the inventors, such as those described in Patent Document 2, the following was discovered: when using a compound containing a nitrogen-fused aromatic ring in its structure as a monomer, the lightfastness is improved by using an unsaturated carbonyl compound with a specific structure, such as methyl cinnamate, which acts as a quencher.

[0007] Previous technical documents

[0008] Patent documents

[0009] Patent Document 1: Japanese Patent Application Publication No. 2021-1328

[0010] Patent Document 2: International Publication No. 2020 / 009053 Summary of the Invention

[0011] The technical problem to be solved by the invention

[0012] The inventors conducted further research and found that, in the technology using monomers with nitrogen-containing fused aromatic rings, the technology described in Patent Document 2, which uses unsaturated carbonyl compounds with specific structures such as methyl cinnamate as quenching agents, cannot be said to have achieved sufficiently high lightfastness, and there is still room for further improvement.

[0013] The objective of this invention is to provide a composition containing a compound having a nitrogen-fused aromatic ring, which yields a cured product or molded article exhibiting superior lightfastness compared to previous methods. Furthermore, the objective of this invention is to provide a cured product or molded article obtained from the composition, as well as an optical component and lens containing the cured product or molded article.

[0014] means for solving technical problems

[0015] That is, the above-mentioned problems of the present invention have been solved by the following method.

[0016] <1>

[0017] A composition comprising component A and component B:

[0018] Component A: A compound containing a nitrogen-fused aromatic ring as part of its structure.

[0019] Component B: A compound represented by any one of the following general formulas (B1) to (B5).

[0020] [Chemical Formula 1]

[0021]

[0022] In the above formula, Ar 101 ~Ar 104 X represents aryl or heteroaryl. 1 Y represents a monovalent substituent. 1 This indicates a hydrogen atom or a monovalent substituent. Ar 101 ~Ar 104 X 1 and Y 1 Two adjacent elements in the loop can bond together to form a ring. Among them, the element that can serve as X... 1 Or Y 1 The monovalent substituents used are not aryl or heteroaryl.

[0023] <2>

[0024] according to <1> The composition, wherein,

[0025] The above-mentioned component A is a compound represented by the following general formula (A1) or (A2) or a polymer having structural units represented by the following general formula (A3) or (A4).

[0026] [Chemical Formula 2]

[0027]

[0028] In the above formula, R 3 and R 4 L represents a hydrogen atom or a monovalent substituent. 1 and L 2 Indicates an alkylene group with 1-6 carbon atoms, an arylene group with 6-10 carbon atoms, or a heteroarylene group with 5-10 cyclic atoms; LL indicates a single bond or a divalent linker; Sp a ~Sp d This indicates a single bond or a divalent linker.

[0029] Pol 1 and Pol 2 It represents a hydrogen atom or a polymeric group. Among them, Pol... 1 and Pol 2 At least one of them is a polymeric group.

[0030] Ring Ar 1 Ar represents an aromatic ring represented by the following formula (AR1), or a fused ring containing the aromatic ring as a constituent ring of a fused ring. 2 This represents an aromatic ring represented by the following formula (AR2), or a fused ring containing the aromatic ring as a constituent ring of a fused ring. Wherein, ring Ar 1 and the ring Ar 2 At least one of them is the aforementioned nitrogen-containing fused aromatic ring.

[0031] R 1 Indicates ring Ar 1 The substituents present in the cyclic atoms, R 2 Indicates ring Ar 2 The substituents present in the cyclic atoms.

[0032] v is an integer greater than or equal to 0. The largest number of v is the ring Ar. 1 The maximum number of substituents that a cyclic atom can have.

[0033] w is an integer greater than or equal to 0. The largest number of w is the ring Ar. 2 The maximum number of substituents that a cyclic atom can have.

[0034] n is an integer from 0 to 5, and X represents an oxygen atom, a carbonyl group, or an amino group, or a combination of two of them.

[0035] [Chemical Formula 3]

[0036]

[0037] In the above formula, X 11 Y 11 X 12 and Y 12 It represents an oxygen atom, a sulfur atom, a nitrogen atom, or a carbon atom.

[0038] Z 11 Indicates -X 11 -C=CY 11 -Together they form a 5- to 7-membered aromatic ring and are composed of atoms selected from oxygen, sulfur, nitrogen and carbon atoms.

[0039] Z 12 Indicates -X 12 -C=CY 12 -Together they form a 5- to 7-membered aromatic ring and are composed of atoms selected from oxygen, sulfur, nitrogen and carbon atoms.

[0040] * Equivalent to the double bond of the cyclopentadiene ring in general formulas (A1) to (A4).

[0041] <3>

[0042] according to <2> The composition, wherein,

[0043] The above-mentioned component A is a compound represented by the above general formula (A1).

[0044] <4>

[0045] according to <3> The composition, wherein,

[0046] The above-mentioned component A is a compound represented by the following general formula (A11).

[0047] [Chemical Formula 4]

[0048]

[0049] In the above formula, X a and X b This represents a nitrogen atom or CH, where the CH at the # position can be replaced by a nitrogen atom. Where X... a X b At least one of the CH atoms at the # position is a nitrogen atom.

[0050] R 11 and R 21 Represents substituents, v1 and w1 are integers from 0 to 4, R 101 and R 102 It represents a hydrogen atom or a methyl group.

[0051] L 1 L 2 Sp a and Sp b The meanings are respectively the same as L in the above general formula (A1) 1 L 2 Sp a and Sp b The meanings are the same.

[0052] <5>

[0053] according to <1> to <4> The composition described in any one of the following statements, wherein,

[0054] The above-mentioned component B is a compound represented by any one of the following general formulas (B11), (B41) or (B51).

[0055] [Chemical Formula 5]

[0056]

[0057] In the above formula, R 201 ~R 204 Represents substituents, where n1 to n4 are integers from 0 to 5, and X 2 Y represents a monovalent substituent. 2 and Y 3 This represents a hydrogen atom or a monovalent substituent. Among them, those that can act as X... 2 Y 2 Or Y 3 The monovalent substituents used are not aryl or heteroaryl.

[0058] <6>

[0059] according to <5> The composition, wherein,

[0060] R in the above general formula (B11) 201 R 202 X 2 and Y 2 At least one of them, R in the above general formula (B41) 201 ~R 203 and Y 3 At least one of them and R in the above general formula (B51) 201 ~R 204 At least one of them has a partial structure represented by any one of the following equations (Pol-1) to (Pol-6).

[0061] [Chemical Formula 6]

[0062]

[0063] * indicates the bonding location.

[0064] <7>

[0065] according to <5> The composition, wherein,

[0066] The above-mentioned component B is a compound represented by the above general formula (B11) or (B41).

[0067] Among them, the above-mentioned Y 2 It is a monovalent substituent.

[0068] <8>

[0069] according to <6> The composition, wherein,

[0070] The above-mentioned component B is a compound represented by the following general formula (B12).

[0071] [Chemical Formula 7]

[0072]

[0073] In the above formula, L a Represents single bonds, -O-, -C(=O)-, -C(=O)O-, alkylene groups, and -CR. β1 =CR β2 - Cycloalkyl or cycloalkylene groups. The right side of the above -C(=O)O- is related to Sp g Bonding.

[0074] R β1 and R β2 It represents a hydrogen atom or a monovalent substituent.

[0075] Sp g Indicates a single bond or a divalent linker, Pol 7 It is a group represented by any one of the above formulas (Pol-1) to (Pol-6).

[0076] Among them, in L a In the case of a single key, Sp g It is a single key.

[0077] R 201 R 202 n1, n2 and Y 2 The meaning of R above is the same as above. 201 R 202 n1, n2 and Y 2 The meanings are the same.

[0078] <9>

[0079] A sort of <1> to <8> The cured product or molded article of the composition described in any one of the above statements.

[0080] <10>

[0081] An optical component containing <9> The solidified material or molded body.

[0082] <11>

[0083] A lens containing <9> The solidified material or molded body.

[0084] In this invention, when multiple substituents or linking groups (hereinafter referred to as substituents, etc.) represented by specific symbols or formulas are present, or when multiple substituents, etc. are specified simultaneously, unless otherwise specified, each substituent, etc., may be the same as or different from each other (regardless of whether it is stated as "each independently"). This also applies to the specification of the number of substituents, etc. Furthermore, when multiple substituents, etc., are close together (especially, adjacent), unless otherwise specified, they may be linked together to form a ring. Furthermore, unless otherwise specified, rings such as alicyclic rings, aromatic rings, and heterocyclic rings may be further fused to form fused rings.

[0085] In this invention, unless otherwise specified, double bonds can be either E-type or Z-type in the presence of E-type or Z-type in the molecule, or a mixture thereof.

[0086] Furthermore, in this invention, unless otherwise specified, when a compound contains one or more asymmetric carbons, the stereochemistry of such asymmetric carbons can be independently achieved by using either the (R) body or the (S) body. As a result, the compound can be a mixture of stereoisomers such as optical isomers or diastereomers, or it can be a racemic mixture.

[0087] In this invention, unless otherwise specified, when a compound has a repeating structure, the number of repeats of the repeating structure can be the same for all repeats, or it can be a mixture of compounds with different numbers of repeats.

[0088] Furthermore, in this invention, the representation of a compound includes compounds whose structure has been modified to a extent that does not impair the effects of the invention. Moreover, the term "compound without explicit description of substitution or non-substitution" refers to compounds that may have any substituents to a extent that does not impair the effects of the invention.

[0089] In this invention, the term "substituent" (which is not explicitly stated as substituted or unsubstituted, and the same applies to linking groups and rings) means that the group may have any substituents without impairing the desired effect. For example, the term "alkyl" indicates that it includes both unsubstituted alkyl and substituted alkyl groups.

[0090] In this invention, when specifying the number of carbon atoms of a certain group, unless otherwise specified in this invention or specification, the number of carbon atoms refers to the total number of carbon atoms of the group as a whole. That is, if the group is in the form of further having substituents, it refers to the total number of carbon atoms including the substituents.

[0091] In this invention, the numerical range represented by “~” refers to the range encompassed by the values ​​recorded before and after “~” as the lower limit and upper limit values.

[0092] In the compositions of the present invention, each component (component A and component B, and other components that may be further suitably included as described below) may be used individually or in combination of two or more. This also applies to cured or molded articles, optical components, and lenses obtained from the compositions of the present invention.

[0093] In the description of the content of each component in the composition of the present invention, the solid component in the composition of the present invention refers to the component remaining in the cured or molded article obtained from the composition of the present invention, other than component A and component B. Generally, the remainder other than the solvent is the "solid component".

[0094] In this invention, "(meth)acrylate" refers to any one or both of acrylate and methacrylate, and "(meth)acryloyl" refers to any one or both of acryloyl and methacryloyl. The monomers in this invention, as distinct from oligomers and polymers, refer to compounds with a weight-average molecular weight of 1000 or less.

[0095] In this invention, the term "aliphatic hydrocarbon group" refers to an alkyl group obtained by removing an arbitrary hydrogen atom from a straight-chain or branched alkane, an alkenyl group obtained by removing an arbitrary hydrogen atom from a straight-chain or branched alkene, or an alkynyl group obtained by removing an arbitrary hydrogen atom from a straight-chain or branched alkyne. In this specification, an aliphatic hydrocarbon group is preferably an alkyl group obtained by removing an arbitrary hydrogen atom from a straight-chain or branched alkane.

[0096] Examples of alkyl groups include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, 1-methylbutyl, 3-methylbutyl, hexyl, 1-methylpentyl, 4-methylpentyl, heptyl, 1-methylhexyl, 5-methylhexyl, 2-ethylhexyl, octyl, 1-methylheptyl, nonyl, 1-methyloctyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecanyl, octadecyl, nonadecanyl, eicosyl, etc.

[0097] Furthermore, in this invention, the aliphatic hydrocarbon group (unsubstituted) is preferably an alkyl group having 1 to 12 carbon atoms, and particularly preferably methyl or ethyl.

[0098] In this invention, when referred to as alkyl, it means a straight-chain or branched alkyl group. Examples of alkyl groups can be given as described above. Similarly, alkyl groups containing alkyl groups (alkoxy, alkoxycarbonyl, acyl, acyloxy, amide, amino, silyl substituted with alkoxy (alkoxysilyl), etc.) also mean straight-chain or branched alkyl groups, and examples of alkyl groups can be given as described above.

[0099] Furthermore, in this invention, as an example of an alkylene group, a group obtained by removing one arbitrary hydrogen atom from the aforementioned alkyl group can be cited; as an example of a straight-chain alkylene group, a group obtained by removing one hydrogen atom bonded to the terminal carbon atom from the aforementioned alkyl group can be cited.

[0100] In this invention, alicyclic hydrocarbon rings refer to saturated hydrocarbon rings (cycloalkanes). Examples of alicyclic hydrocarbon rings include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclononane, and cyclodecane.

[0101] In this invention, an unsaturated hydrocarbon ring refers to a hydrocarbon ring that is not an aromatic ring within a hydrocarbon ring having carbon-carbon unsaturated double bonds. Examples of unsaturated hydrocarbon rings include indene, indene-monene, and fluorene.

[0102] In this invention, when referred to as an alicyclic hydrocarbon group, it means a cycloalkyl group obtained by removing an arbitrary hydrogen atom from a cycloalkane. Examples of alicyclic hydrocarbon groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, etc., and cycloalkyl groups with 3 to 12 carbon atoms are preferred.

[0103] In this invention, when referred to as an unsaturated hydrocarbon cyclic group, it means a group obtained by removing an arbitrary hydrogen atom from an unsaturated hydrocarbon ring.

[0104] In this invention, cycloalkylene refers to a divalent group obtained by removing two arbitrary hydrogen atoms from a cycloalkane. An example of cycloalkylene is the cyclohexylene group.

[0105] In this invention, when referred to as an aromatic ring, it means any or both of aromatic hydrocarbon rings and aromatic heterocycles.

[0106] In this invention, an aromatic hydrocarbon ring refers to an aromatic ring formed solely by carbon atoms. The aromatic hydrocarbon ring can be a monocyclic or fused ring. Preferably, it is an aromatic hydrocarbon ring with 6 to 14 carbon atoms. Examples of aromatic hydrocarbon rings include benzene rings, naphthalene rings, anthracene rings, and phenanthrene rings. In this specification, when referring to an aromatic hydrocarbon ring bonded to other rings, the aromatic hydrocarbon ring simply needs to substitute a monovalent or divalent aromatic hydrocarbon group on the other ring.

[0107] In this invention, when a monovalent group is referred to as an aromatic hydrocarbon group, it means a monovalent group obtained by removing an arbitrary hydrogen atom from an aromatic hydrocarbon ring. The monovalent aromatic hydrocarbon group (aryl) is preferably an aromatic hydrocarbon group with 6 to 14 carbon atoms. Examples include phenyl, 1-naphthyl, 2-naphthyl, 1-anthrayl, 2-anthrayl, 3-anthrayl, 4-anthrayl, 9-anthrayl, 1-phenanthyl, 2-phenanthyl, 3-phenanthyl, 4-phenanthyl, and 9-phenanthyl. Among these, phenyl is preferred.

[0108] In this invention, when a divalent group is referred to as an aromatic hydrocarbon group, it means a divalent group obtained by removing an arbitrary hydrogen atom from the aforementioned monovalent aromatic hydrocarbon group. Examples of divalent aromatic hydrocarbon groups (aryl groups) include phenylene, naphthylene, phenanthrene, etc., with phenylene being preferred, and 1,4-phenylene being more preferred.

[0109] In this invention, an aromatic heterocycle refers to an aromatic ring formed by carbon atoms and heteroatoms. Examples of heteroatoms include oxygen atoms, nitrogen atoms, and sulfur atoms. The aromatic heterocycle can be a monocyclic or fused ring, and the number of atoms constituting the ring is preferably 5 to 20, more preferably 5 to 14. Each ring constituting the aromatic heterocycle is preferably a 5- or 6-membered ring. The number of heteroatoms in the ring is not particularly limited, but is preferably 1 to 3, more preferably 1 to 2. Examples of aromatic heterocycles include furan rings, thiophene rings, pyrrole rings, imidazole rings, isothiazole rings, isoxazole rings, pyridine rings, pyrazine rings, pyrimidine rings, pyridazine rings, quinoline rings, benzofuran rings, benzothiazole rings, benzooxazole rings, and nitrogen-containing fused aromatic rings described later. In this specification, when referred to as an aromatic heterocycle bonded to other rings, the aromatic heterocycle simply needs to be a monovalent or divalent aromatic heterocyclic group substituting for the other ring.

[0110] In this invention, when a monovalent group is referred to as an aromatic heterocyclic group, it means a monovalent group obtained by removing an arbitrary hydrogen atom from an aromatic heterocycle. Examples of monovalent aromatic heterocyclic groups (heteroaryl groups) include furanyl, thiophene, pyrrole, imidazolyl, isothiazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, benzofuranyl (preferably 2-benzofuranyl), benzothiazolyl (preferably 2-benzothiazolyl), and benzoxazolyl (preferably 2-benzoxazolyl). Among these, furanyl, thiophene, benzofuranyl, benzothiazolyl, and benzoxazolyl are preferred, and 2-furanyl and 2-thiophene are more preferred.

[0111] In this invention, the term "divalent aromatic heterocyclic group" refers to a divalent group obtained by removing two arbitrary hydrogen atoms from an aromatic heterocycle. An example of a divalent aromatic heterocyclic group (heteroaryl) is a divalent group obtained by removing one arbitrary hydrogen atom from the aforementioned (monovalent) aromatic heterocyclic group.

[0112] In this invention, examples of halogen atoms include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.

[0113] In this invention, the structure represented by any of the following descriptions represents an isopropylene structure. This isopropylene structure can be any one of two structural isomers having a methyl group bonded to any carbon atom constituting the vinyl group; these structural isomers can also coexist.

[0114] [Chemical Formula 8]

[0115]

[0116] Examples of structural isomers that can exist, such as the example having the aforementioned isopropylene structure, include the following structural isomers in which, in polymeric compounds represented by any of the general formulas (A0) to (A2) described below, and in polymers having structural units represented by general formulas (A3) or (A4), the substitution positions of the substituents differ when the structure has a structure in which a substituent is substituted on a straight-chain alkylene group. Component A can also be a mixture of such structural isomers.

[0117] Invention Effects

[0118] The cured or molded articles obtained from the compositions of the present invention exhibit excellent lightfastness. Therefore, even when used for extended periods in outdoor or other light-exposed environments, optical components and lenses of the present invention containing this cured or molded article as a constituent part can suppress staining. Detailed Implementation

[0119] The present invention will be described in detail. The description of the constituent elements described below is sometimes based on representative embodiments or specific examples, but the present invention is not limited to such embodiments.

[0120] <Composition>

[0121] The composition of the present invention contains the following components A and B.

[0122] Component A: A compound containing a nitrogen-fused aromatic ring as part of its structure.

[0123] Component B: A compound represented by any one of the general formulas (B1) to (B5) described below.

[0124] As will be described later, the component A contained in the composition of the present invention can be a polymeric compound or a polymer, as long as it has the above-mentioned nitrogen-containing fused aromatic ring as part of the structure.

[0125] When the composition of the present invention contains a polymeric compound comprising a nitrogen-fused aromatic ring (also simply referred to as "a compound comprising a nitrogen-fused aromatic ring") as component A, the composition of the present invention becomes a curable composition; when the composition of the present invention contains a polymer having a nitrogen-fused aromatic ring (preferably a structural unit comprising a nitrogen-fused aromatic ring) as component A, the composition of the present invention becomes a resin composition. Hereinafter, the former will be referred to as the curable composition of the present invention, and the latter as the resin composition of the present invention.

[0126] Furthermore, in the compositions of the present invention, compositions that simultaneously contain both a compound comprising a nitrogen-fused aromatic ring and a polymer having a nitrogen-fused aromatic ring are classified as curable compositions of the present invention. That is, the resin compositions of the present invention do not contain polymerizable compounds comprising nitrogen-fused aromatic rings.

[0127] In addition to components A and B described above, the compositions of the present invention may appropriately contain other components. Specifically, these other components may include, for example, (meth)acrylate monomers (monomers other than components A or B), thermal free radical polymerization initiators, photofree radical polymerization initiators, polymers or monomers other than those described above, dispersants, plasticizers, heat stabilizers, mold release agents, and other additives. Furthermore, the resin compositions of the present invention preferably do not contain polymers or monomers having polymerizable groups, thermal free radical polymerization initiators, or photofree radical polymerization initiators.

[0128] In the compositions of the present invention, component A contains a nitrogen-containing fused aromatic ring as a partial structure. When the compositions of the present invention are curable compositions containing a compound containing a nitrogen-containing fused aromatic ring as component A, their polymers (cured products), and when the compositions of the present invention are resin compositions containing a polymer having a nitrogen-containing fused aromatic ring as component A, their molded bodies exhibit extremely high absorption wavelengths in the ultraviolet region of approximately 300–400 nm. Therefore, as a refractive index dispersion characteristic, they are considered to have low Abbe number (νD) or high partial dispersion ratio (θg, F-value), exhibiting excellent optical properties. However, the aforementioned polymers having a nitrogen-containing fused aromatic ring are prone to photo-induced degradation (photoreaction) due to the nitrogen-containing fused aromatic ring contained as a partial structure.

[0129] Based on the research conducted to date, the inventors have discovered that, as described in Patent Document 2 above, by formulating unsaturated carbonyl compounds with a specific structure, such as methyl cinnamate, from a specific fused-ring compound containing nitrogen atoms, the unsaturated carbonyl compound acts as a quencher, causing energy transfer from the polymer with the nitrogen-containing fused aromatic ring excited by light absorption to the quencher. The polymer with the nitrogen-containing fused aromatic ring returns to its substrate state, thereby improving lightfastness. However, further research by the inventors has revealed that the improvement in lightfastness using the aforementioned unsaturated carbonyl compound with the specific structure is not sufficient; there is a problem that even increasing the amount of the unsaturated carbonyl compound does not further improve lightfastness. To address this issue of peak lightfastness, the inventors have found that by replacing methyl cinnamate with a component B having a specific chemical structure, even with a small amount of component B, a significantly improved lightfastness effect is observed compared to using methyl cinnamate. The reason for this is not yet certain, but it is speculated as follows.

[0130] In the prior art described in Patent Document 2 above, it is believed that in addition to energy transfer from the polymer having a nitrogen-containing fused aromatic ring in the aforementioned transfer state, a reaction occurs in which an unsaturated carbonyl compound with a specific structure, such as methyl cinnamate, accepts energy and undergoes a [2+2] photocycloaddition reaction to produce a corresponding cyclobutane compound. It is believed that in the cyclobutane compound, the hydrogen atom at the benzyl position on the cyclobutane ring is easily abstracted, resulting in a hydrogen abstraction reaction caused by the aforementioned polymer having a nitrogen-containing fused aromatic ring, which is excited by absorbed light. This reaction is considered the main reason for the coloration of the aforementioned polymer having a nitrogen-containing fused aromatic ring. In this invention, it is speculated that, as a compound having a chemical structure that is not prone to the above-mentioned [2+2] photocycloaddition reaction due to steric hindrance and is not prone to subsequent hydrogen abstraction reaction, a compound represented by any one of the general formulas (B1) to (B5) described below can be used as component B by substituents containing at least 3 of the 4 hydrogen atoms in CH2=CH2 being replaced by substituents, wherein at least 2 of them are aryl or heteroaryl.

[0131] [Component A: A compound having a nitrogen-containing fused aromatic ring as part of its structure]

[0132] The compositions of the present invention contain a compound having a nitrogen-fused aromatic ring as a partial structure as component A. Because component A contains a nitrogen-fused aromatic ring as a partial structure, the cured product of the curable composition of the present invention or the molded body of the resin composition of the present invention exhibits absorption in the near-ultraviolet region, which helps to reduce the aberrant dispersion of the refractive index or increase the partial dispersion ratio (θg, F value), thereby improving the chromatic aberration correction function when used as a composite lens.

[0133] (containing nitrogen-fused aromatic rings)

[0134] The nitrogen-containing fused aromatic rings of the compound as component A refer to all nitrogen-containing fused aromatic rings that satisfy all of the following (i) to (iii).

[0135] (i) It has a fused ring structure consisting of two or more 6-membered rings.

[0136] (ii) Having at least one nitrogen atom (N) as a cyclic atom.

[0137] (iii) All cyclic atoms have p orbitals, and all of these p orbitals contribute to aromaticity.

[0138] That is, a nitrogen-containing fused aromatic ring (hereinafter also referred to as "nitrogen-containing fused aromatic ring") that satisfies all of the above (i) to (iii) is an aromatic heterocycle formed by the fusion of two or more six-membered rings, and is an aromatic ring containing at least one nitrogen atom as a cyclic atom constituting the aromatic heterocycle.

[0139] The above-mentioned (i) preferably has a fused ring structure composed of 2 to 5 six-membered rings, and more preferably has a fused ring structure composed of 2 six-membered rings.

[0140] From the viewpoint of further improving lightfastness, the above-mentioned (ii) specification preferably contains two or more nitrogen atoms as cyclic atoms, more preferably two or three, and even more preferably two.

[0141] The nitrogen-fused aromatic ring may contain heteroatoms other than nitrogen (N), such as oxygen (O) or sulfur (S), and preferably does not contain such heteroatoms.

[0142] The above (iii) provision refers to the fact that all rings (monocyclic rings) constituting the nitrogen-containing fused aromatic ring exhibit aromaticity.

[0143] For example, in compounds represented by the general formula (A11) described later, the aforementioned nitrogen-containing fused aromatic ring is a fused ring structure formed by the fusion of two six-membered rings located on the lower right side of the structural formula. That is, it can have an R located on the lower left side of the structural formula. 11The benzene ring and the five-membered ring located to the right of the benzene ring are not included in the above-mentioned nitrogen-containing fused aromatic rings. This is because the structure located at the point where R can have 11 One carbon atom of the five-membered ring on the right side of the benzene ring has a p orbital that does not contribute to aromaticity, and therefore does not satisfy the above requirement (iii).

[0144] Furthermore, any group represented by any of the general formulas (Ar-a) to (Ar-c) described later, as the aforementioned nitrogen-containing fused aromatic ring, has at least a quinoxaloline ring structure; and any group represented by the general formulas (Ar-d) or (Ar-e) described later, as the aforementioned nitrogen-containing fused aromatic ring, has at least a quinazoline ring structure. Additionally, in T... 1 With T 2 or Z 1 With Z 2 When they are bonded together with each other to form nitrogen-containing fused aromatic rings that satisfy all of (i) to (iii) above, the following are included: T 1 With T 2 or Z 1 With Z 2 The aromatic rings formed by their bonding together constitute the aforementioned nitrogen-containing fused aromatic rings.

[0145] Examples of nitrogen-containing fused aromatic rings include those with one nitrogen atom: isoquinoline ring, quinoline ring; those with two nitrogen atoms: phthalazine ring, quinoxaline ring, quinazoline ring, borazine ring, naphthidine ring with a different nitrogen atom configuration; those with three nitrogen atoms: pyrido[3,4-b]pyrazine ring, pyrido[2,3-b]pyrazine ring; or those with four nitrogen atoms: pteridine ring, etc. From the viewpoint of further improving lightfastness, quinoxaline ring or quinazoline ring is preferred among these.

[0146] The aforementioned nitrogen-containing fused aromatic ring may have substituents or be unsubstituted. Furthermore, when the aforementioned nitrogen-containing fused aromatic ring has substituents, adjacent substituents may bond with each other to form a ring.

[0147] The manner in which the nitrogen-containing fused aromatic ring is incorporated as a partial structure in the compound is not particularly limited. For example, it can be incorporated as a monovalent or divalent group into the compound by removing a hydrogen atom from any carbon atom of the ring constituting the nitrogen-containing fused aromatic ring (hereinafter, also simply referred to as "the connecting bond on the nitrogen-containing fused aromatic ring").

[0148] For example, when the nitrogen-containing fused aromatic ring is a quinoxaline ring or a quinazoline ring, the position of the connecting bond on the quinoxaline ring or the quinazoline ring is not particularly limited, and preferably two of them are selected from the 5th to the 8th position, more preferably a combination of the 5th and 8th positions, or a combination of the 6th and 7th positions.

[0149] Furthermore, when the linking bond is a linking bond on a substituent of the quinoxaline ring or quinazoline ring, the position of the substituent having the linking bond and the position of the linking bond are not particularly limited. As the substituent having the linking bond, an aromatic hydrocarbon group or an aromatic heterocyclic group is preferred, more preferably an aromatic hydrocarbon group having 6 to 12 carbon atoms, even more preferably a phenyl group that can have substituents (in the state of having a linking bond, a phenylene group that can have substituents), and particularly preferably a phenyl group (in the state of having a linking bond, a phenylene group). When a phenyl group has a linking bond, its position is preferably at position 4 (setting the bonding position with the quinoxaline ring or quinazoline ring as position 1) (i.e., 1,4-phenylene).

[0150] Component A may be a polymeric compound containing the aforementioned nitrogen-containing fused aromatic ring, or a polymer having the aforementioned nitrogen-containing fused aromatic ring (preferably a structural unit containing the aforementioned nitrogen-containing fused aromatic ring).

[0151] When the composition of the present invention contains a polymerizable compound comprising a nitrogen-fused aromatic ring as component A, the composition of the present invention becomes a curable composition, and the cured product obtained by curing the composition of the present invention, i.e., polymerizing component A, can be used as a cured product with a low Abbe number (νD) or a high partial dispersion ratio (θg, F value). Conversely, when the composition of the present invention contains a polymer having a structural unit comprising a nitrogen-fused aromatic ring as component A, the composition of the present invention becomes a resin composition, and the molded body obtained by molding the composition of the present invention can be used as a molded body with a low Abbe number (νD) or a high partial dispersion ratio (θg, F value).

[0152] [Compounds containing nitrogen-fused aromatic rings]

[0153] As compounds comprising the aforementioned nitrogen-fused aromatic rings, compounds represented by the following general formula (A0) or by the general formulas (A1) or (A2) described below are preferably examples. Among these, compounds represented by the general formulas (A1) or (A2) described below are more preferred from the viewpoint of further improving lightfastness.

[0154] The following sections will describe in detail the compounds represented by the general formula (A0) and the compounds represented by the general formula (A1) or (A2).

[0155] (Compounds represented by the general formula (A0))

[0156] As a compound containing the above-mentioned nitrogen-containing fused aromatic ring, a compound represented by the following general formula (A0) is preferably cited.

[0157] [Chemical Formula 9]

[0158]

[0159] In the above formula, Ar represents a group represented by any one of the following general formulas (Ar-a) to (Ar-e).

[0160] L represents a single bond, -O-, -S-, -C(=O)-, -OC(=O)-, -C(=O)O-, -OC(=O)O-, -NR α1 C(=O)-、-C(=O)NR α2 -、-OC(=O)NR α3 -、-NR α4 C(=O)O-, -SC(=O)- or -C(=O)S-.

[0161] R α1 ~R α4 Indicate -Sp α -Pol 3 Or halogen atoms.

[0162] Sp and Sp α Indicates a single bond or a divalent linker, Pol and Pol 3 It represents a hydrogen atom or a polymeric group.

[0163] Multiple Ls can be the same or different, multiple Sps can be the same or different, and multiple Pols can be the same or different.

[0164] The polymeric compound represented by the general formula (A0) has at least one polymeric group.

[0165] The following discussion focuses on Ar, L, Sp, and Sp. α and Pol and Pol 3 The substituents are explained.

[0166] (1) Ar: A group represented by any one of the general formulas (Ar-a) to (Ar-e).

[0167] [Chemical Formula 10]

[0168]

[0169] In the above formula, Z 1 Z 2 Z 3 and Z 4The following groups represent hydrogen atoms or, as monovalent groups, aliphatic hydrocarbon groups with 1 to 20 carbon atoms, alkoxy groups with 1 to 20 carbon atoms, alkoxycarbonyl groups with 1 to 20 carbon atoms, alicyclic hydrocarbon groups with 3 to 20 carbon atoms, aromatic hydrocarbon groups with 6 to 20 carbon atoms, halogen atoms, cyano groups, nitro groups, and -NR groups. 12 R 13 -SR 12 Or aromatic heterocyclic groups with 5 to 20 cyclic atoms.

[0170] Z 1 and Z 2 They can also bond with each other to form aromatic hydrocarbon rings or aromatic heterocycles.

[0171] R 12 and R 13 It represents an alkyl group having 1 to 6 hydrogen atoms or carbon atoms.

[0172] Furthermore, * indicates the bonding position with Pol-Sp-L-.

[0173] Able to be Z 1 ~Z 4 The following groups are used: aliphatic hydrocarbon groups with 1-20 carbon atoms, alkoxy groups with 1-20 carbon atoms, alkoxycarbonyl groups with 1-20 carbon atoms, alicyclic hydrocarbon groups with 3-20 carbon atoms, aromatic hydrocarbon groups with 6-20 carbon atoms, or aromatic heterocyclic groups with 5-20 cyclic atoms. 1 and Z 2 Aromatic hydrocarbon rings or aromatic heterocycles that can bond together with each other can act as R 12 and R 13 The alkyl groups with 1 to 6 carbon atoms used can be unsubstituted or have substituents.

[0174] As for the substituents or rings that can be present, there are no particular limitations as long as they are not groups with excessively high elimination properties (groups that are easily decomposed), such as acyl chloride (-COCl) or -OTf (-O-SO2CF3). Examples include halogen atoms, hydroxyl groups, amino groups, cyano groups, nitro groups, nitroso groups, carboxyl groups, alkyl groups with 1 to 6 carbon atoms, alkoxy groups with 1 to 6 carbon atoms, alkoxy carbonyl groups with 1 to 6 carbon atoms, alkyl carbonyl groups with 1 to 6 carbon atoms, alkyl carbonyl groups with 1 to 6 carbon atoms, alkyl sulfinyl groups with 1 to 6 carbon atoms, alkyl sulfonyl groups with 1 to 6 carbon atoms, fluoroalkyl groups with 1 to 6 carbon atoms, alkyl thioalkyl groups with 1 to 6 carbon atoms, N-alkylamino groups with 1 to 6 carbon atoms, N,N-dialkylamino groups with 2 to 12 carbon atoms, N-alkylaminosulfonyl groups with 1 to 6 carbon atoms, and N,N-dialkylaminosulfonyl groups with 2 to 12 carbon atoms.

[0175] Among these substituents, halogen atoms, hydroxyl groups, alkyl groups having 1 to 6 carbon atoms, alkoxy groups having 1 to 6 carbon atoms, or fluoroalkyl groups having 1 to 6 carbon atoms are preferred, and fluorine atoms, chlorine atoms, bromine atoms, hydroxyl groups, methyl groups, methoxy groups, or fluoromethyl groups are more preferred.

[0176] Z 1 and Z 2 Preferably, hydrogen atoms or aliphatic hydrocarbon groups with 1 to 20 carbon atoms or Z groups are preferred. 1 With Z 2 They bond together to form an aromatic hydrocarbon ring, more preferably hydrogen atoms or methyl or Z atoms. 1 With Z 2 They bond together to form a benzene ring.

[0177] Z 3 and Z 4 Preferably, it is a hydrogen atom or an aliphatic hydrocarbon group with 1 to 20 carbon atoms, more preferably a hydrogen atom or a methyl group.

[0178] T in general formulas (Ar-a) and (Ar-b) 1 and T 2 and T in general formulas (Ar-d) and (Ar-e) 5 and T 6 Represents halogen, cyano, nitro, -L 6 -Sp β -Pol 6 Alicyclic hydrocarbon groups with 3 to 20 carbon atoms, aromatic hydrocarbon groups with 6 to 20 carbon atoms, aromatic heterocyclic groups with 5 to 20 cyclic atoms, and the above-mentioned -NR 12 R 13 or -SR 12 As a monovalent group.

[0179] L 6 The meaning of is the same as that of L described later. Specifically, in the description of the linking group exemplified by L, the left side is bonded to a quinoxaline ring or a quinazoline ring, and the right side is bonded to Sp. β Bonding. For example, if we take the linking group -OC (=O)- as an example, the left side refers to the ether bond side, and the right side refers to the carbonyl bond side.

[0180] L 6 Preferably, it is a single bond or -O-, -OC(=O)- or -C(=O)O-, more preferably a single bond.

[0181] Sp β The -CH2- group represents a single bond, a straight-chain alkylene group having 1 to 30 carbon atoms, or one or more non-adjacent -CH2- groups in a straight-chain alkylene group having 2 to 30 carbon atoms, selected from -O-, -S-, -C(=O)-, -OC(=O)-, -C(=O)O-, -OC(=O)O-, -NRβ1 C(=O)-、-C(=O)NR β2 -、-OC(=O)NR β3 -、-NR β4 The groups substituted by the groups in C(=O)O-, -SC(=O)- and -C(=O)S-.

[0182] R β1 ~R β4 Indicate -Sp γ -Pol 4 Or halogen atoms.

[0183] Sp γ A group that represents a single bond, a straight-chain alkylene group having 1 to 30 carbon atoms, or a straight-chain alkylene group having 2 to 30 carbon atoms in which one or more non-adjacent -CH2- groups are substituted by groups selected from -O-, -S-, -C(=O)-, -OC(=O)-, -C(=O)O-, -OC(=O)O-, -NHC(=O)-, -C(=O)NH-, -OC(=O)NH-, -NHC(=O)O-, -SC(=O)-, and -C(=O)S-.

[0184] Pol 4 and Pol 6 The meaning of is the same as the meaning of Pol as described later.

[0185] As Sp β and Sp γ Preferably, it is a straight-chain alkylene group having 1 to 10 carbon atoms, or a straight-chain alkylene group having 2 to 10 carbon atoms in which one or more -CH2- groups are replaced by groups selected from -O-, -C(=O)-, -OC(=O)-, -C(=O)O- and -OC(=O)O-.

[0186] As Pol 4 and Pol 6 Hydrogen atoms are preferred.

[0187] As -L 6 -Sp β -Pol 6 Examples include hydrogen atoms, groups described later as groups represented by -L-Sp-Pol, and groups selected from aliphatic hydrocarbon groups having 1 to 20 carbon atoms and alkoxy groups having 1 to 20 carbon atoms, or groups having polymerizable groups at the ends of these groups.

[0188] As -Sp γ -Pol 4 Preferably, it contains hydrogen atoms or alkyl groups having 1 to 4 carbon atoms, more preferably hydrogen atoms or unsubstituted alkyl groups having 1 to 4 carbon atoms.

[0189] R β1 ~R β4 Preferably, it contains hydrogen atoms, alkyl groups with 1 to 4 unsubstituted carbon atoms, or halogen atoms.

[0190] As T 1 and T 2 Preferably, the aromatic hydrocarbon group having 6 to 20 carbon atoms, the aromatic heterocyclic group having 5 to 20 cyclic atoms, the aliphatic hydrocarbon group having 1 to 20 carbon atoms, or the following examples of groups represented by -L-Sp-Pol, are more preferably phenyl, biphenyl, naphthyl, alkyl having 1 to 6 carbon atoms, furanyl or thiophene, and even more preferably phenyl, 4-biphenyl, 1-naphthyl, 2-naphthyl, alkyl having 1 to 6 carbon atoms, 2-furanyl or 2-thiophene, and particularly preferably phenyl.

[0191] T 1 With T 2 They can be the same or different, but the same is preferred. Among them, T is also preferred. 1 and T 2 One of them is a phenyl group, and the other is an alkyl group with 1 to 4 carbon atoms or a hydrogen atom.

[0192] Preferred T 1 and T 2 At least one of them is not a hydrogen atom. And, T 1 and T 2 At least one of them is preferably an aromatic hydrocarbon group with 6 to 20 carbon atoms or an aromatic heterocyclic group with 5 to 20 cyclic atoms.

[0193] T 1 With T 2 They can also bond with each other to form aromatic hydrocarbon rings or aromatic heterocycles. In this case, T 1 With T 2 Preferably, they are bonded together to form an aromatic hydrocarbon ring, more preferably to form benzene, naphthalene, anthracene or phenanthrene, and even more preferably to form benzene or phenanthrene.

[0194] As T 5 and T 6 Preferably, the aromatic hydrocarbon group having 6 to 20 carbon atoms, the aromatic heterocyclic group having 5 to 20 cyclic atoms, the aliphatic hydrocarbon group having 1 to 20 carbon atoms, or the following examples of groups represented by -L-Sp-Pol, are more preferably hydrogen atoms, phenyl, biphenyl, naphthyl, alkyl having 1 to 6 carbon atoms, furanyl or thiophene, and even more preferably hydrogen atoms, phenyl, 4-biphenyl, 1-naphthyl, 2-naphthyl, alkyl having 1 to 6 carbon atoms, 2-furanyl or 2-thiophene, and particularly preferably hydrogen atoms or phenyl.

[0195] T 5 With T6 They can be the same or different. T is preferred. 6 It is any one of the preferred substituents mentioned above, and T 5 It is a hydrogen atom.

[0196] Preferred T 5 and T 6 At least one of them is not a hydrogen atom. And, T 5 and T 6 At least one of them is preferably an aromatic hydrocarbon group or an aromatic heterocyclic group with 6 to 20 carbon atoms.

[0197] In the general formula (Ar-c), T 3 and T 4 It indicates a divalent linking group, representing a divalent aromatic hydrocarbon group or a divalent aromatic heterocyclic group with 6 to 12 carbon atoms.

[0198] As T 3 and T 4 Preferably, it is a divalent aromatic hydrocarbon group with 6 to 12 carbon atoms, more preferably a divalent aromatic hydrocarbon group with 6 to 10 carbon atoms, even more preferably phenylene, and particularly preferably 1,4-phenylene.

[0199] T 3 With T 4 They can be the same or different, but the same is preferred.

[0200] (2)L

[0201] In the general formula (A0), L represents a single bond, -O-, -S-, -C(=O)-, -OC(=O)-, -C(=O)O-, -OC(=O)O-, and -NR. α1 C(=O)-、-C(=O)NR α2 -、-OC(=O)NR α3 -、-NR α4 C(=O)O-, -SC(=O)-, or -C(=O)S-. Furthermore, in the above descriptions of linking groups, the left side is bonded to Ar, and the right side is bonded to Sp. For example, if we take the linking group -OC(=O)- as an example, the left side refers to the ether bond side, and the right side refers to the carbonyl bond side.

[0202] R α1 ~R α4 Indicate -Sp α -Pol 3 Or halogen atoms.

[0203] L is preferably -O-, -OC(=O)-, -C(=O)O-, -OC(=O)O-, or -NR. α1 C(=O)-、-C

[0204] (=O)NR α2 -、-OC(=O)NR α3 -or-NR α4 C(=O)O-, more preferably -O-, -OC(=O)-, -OC(=O)O- or -OC(=O)NR α3 -, more preferably -O- or -OC(=O)-.

[0205] Multiple Ls can be the same or different, but the same is preferred.

[0206] (3) Sp and Sp α

[0207] Sp and Sp α This indicates a single bond or a divalent linker.

[0208] Sp and Sp as divalent linking groups α Examples include straight-chain alkylene groups, cycloalkylene groups, divalent aromatic hydrocarbon groups, and divalent aromatic heterocyclic groups. Furthermore, examples include groups selected from straight-chain alkylene groups, cycloalkylene groups, divalent aromatic cyclic groups, and divalent aromatic heterocyclic groups, connected by two or more linking groups via single bonds, selected from -O-, -S-, -C(=O)-, -OC(=O)-, -C(=O)O-, -OC(=O)O-, and -NR-. α1 C(=O)-、-C(=O)NR α2 -、-OC(=O)NR α3 -、-NR α4 Linking groups are formed by the bonding of linking groups in C(=O)O-, -SC(=O)- and -C(=O)S-.

[0209] Furthermore, in the description of the linking group mentioned above, the left side is connected to L or N (Sp). α (in the case of) bonding, the right side is with Pol or Pol 3 (Sp α (The case of) bonding. For example, if we take the linking group -OC (=O)- as an example, the left side refers to the ether bond side, and the right side refers to the carbonyl bond side.

[0210] R α1 ~R α4 The meanings are respectively the same as those of the aforementioned R α1 ~R α4 The meanings are the same.

[0211] As can be Sp and Sp αThe straight-chain alkylene, cycloalkylene, divalent aromatic hydrocarbon, and divalent aromatic heterocyclic groups that can be used are not particularly limited in terms of substituents, as long as they are not groups with excessive elimination properties (easily decomposed groups) such as acyl chloride (-COCl) or -OTf (-O-SO2CF3). Examples include alkyl, cycloalkyl, alkoxy, acyl, acyloxy, alkoxycarbonyl, amide, amino, halogen, nitro, and cyano groups, as well as substituents formed by combining two or more of the above substituents.

[0212] The substituent can be -Sp 5 -Pol 5 The group indicated by Sp. 5 and Pol 5 The meanings of and are the same as those of Sp and Pol, and the preferred ranges are also the same. The number of substituents is not particularly limited and can range from 1 to 4. When there are 2 or more substituents, the 2 or more substituents can be the same or different from each other.

[0213] As the divalent linking group represented by Sp, preferably a straight-chain alkylene group with 1 to 30 carbon atoms, or a straight-chain alkylene group with 1 to 30 carbon atoms and a cycloalkylene group with 3 to 10 carbon atoms connected via a single bond, -O-, -C(=O)-, -OC(=O)-, -C(=O)O-, -OC(=O)O-, or -NR- α1 C(=O)- or -C(=O)NR α2 -The linking group formed by bonding, or one or more non-adjacent -CH2- groups in a straight-chain alkylene group having 2 to 30 carbon atoms, are selected from -O-, -S-, -C(=O)-, -OC(=O)-, -C(=O)O-, -OC(=O)O-, -NR α1 C(=O)-、-C(=O)NR α2 -、-OC(=O)NR α3 -、-NR α4 The groups substituted by the groups in C(=O)O-, -SC(=O)- and -C(=O)S-.

[0214] In the aforementioned straight-chain alkylene groups with 2 to 30 carbon atoms, -CH2- is selected from -O-, -S-, -C(=O)-, -OC(=O)-, -C(=O)O-, -OC(=O)O-, and -NR. α1 C(=O)-、-C(=O)NR α2 -、-OC(=O)NR α3 -、-NR α4Among the groups substituted by C(=O)O-, -SC(=O)-, and -C(=O)S- (hereinafter referred to as "other divalent groups" in this paragraph), the aforementioned other divalent groups preferably do not directly bond with L. That is, the site substituted by the aforementioned other divalent groups is preferably not the L-side end of Sp.

[0215] As a divalent linking group represented by Sp, more preferably, it is a straight-chain alkylene group having 1 to 20 carbon atoms, a linking group formed by bonding a straight-chain alkylene group having 1 to 20 carbon atoms to a cycloalkylene group having 3 to 6 carbon atoms via -O-, -C(=O)-, -OC(=O)-, -C(=O)O- or -OC(=O)O-, or one or more non-adjacent -CH2- groups in a straight-chain alkylene group having 2 to 20 carbon atoms selected from -O-, -C(=O)-, -OC(=O)-, -C(=O)O-, -OC(=O)O-, -NR- α1 C(=O)-、-C(=O)NR α2 -、-OC(=O)NR α3 -and-NR α4 The substituent group in C(=O)O- is more preferably a straight-chain alkylene group with 1 to 10 carbon atoms, a linking group formed by the bonding of a straight-chain alkylene group with 1 to 10 carbon atoms and a cycloalkylene group with 3 to 6 carbon atoms via -O-, -C(=O)-, -OC(=O)- or -C(=O)O-, or a group in a straight-chain alkylene group with 2 to 10 carbon atoms where one or more non-adjacent -CH2- groups are replaced by a group selected from -O-, -C(=O)-, -OC(=O)- and -C(=O)O-, particularly preferably a group without substituents or with a methyl group as the substituent. A linking group consisting of a straight-chain alkylene group having 1 to 10 carbon atoms, a straight-chain alkylene group having 1 to 10 carbon atoms without substituents or with methyl as a substituent, and an unsubstituted cycloalkylene group having 3 to 6 carbon atoms bonded via -O-, -C(=O)-, -OC(=O)-, or -C(=O)O-, or a group in which one or more -CH2- atoms in a straight-chain alkylene group having 2 to 10 carbon atoms without substituents or with methyl as a substituent are replaced by a group selected from -O-, -C(=O)-, -OC(=O)-, and -C(=O)O-.

[0216] Multiple Sp can be the same or different, but the same is preferred.

[0217] In Pol-Sp-L-, it is preferable that Sp and L are not both single bonds, and more preferably neither are single bonds.

[0218] In the general formula (A0), -L-Sp- is preferably a structure formed by repeating -OC(=O)-C2H4- or -OC(=O)-C2H4- 2 to 10 times, more preferably a structure formed by repeating -OC(=O)-C2H4- 2 to 5 times, and even more preferably -OC(=O)-C2H4-OC(=O)-C2H4-.

[0219] As a result of Sp α The divalent linking group is preferably a single bond or a straight-chain alkylene group having 1 to 10 carbon atoms, more preferably a straight-chain alkylene group having 1 to 5 carbon atoms, even more preferably a straight-chain alkylene group having 1 to 3 carbon atoms, and particularly preferably an unsubstituted straight-chain alkylene group having 1 to 3 carbon atoms.

[0220] (4) Pol and Pol 3

[0221] Pol and Pol 3 It represents a hydrogen atom or a polymeric group.

[0222] As a Pol and Pol 3 The polymerizable group used can be any group containing one of the following structures: vinylidene, ethylene oxide, or oxetane. From the viewpoint of simplicity in compound synthesis, the polymerizable group is preferably associated with Sp or Sp... α The linker is an oxygen atom and contains a group of any one of the following structures: vinylidene structure, ethylene oxide structure, and oxetane structure. For example, polymerizable groups represented by any one of the following formulas (Pol-1) to (Pol-6) can be cited.

[0223] [Chemical Formula 11]

[0224]

[0225] * indicates the bonding location.

[0226] Among these, (meth)acryloyloxy is preferred, and methacryloyloxy is more preferably represented by the above formula (Pol-1) or formula (Pol-2).

[0227] Pol is preferably a polymerizable group, and more preferably (meth)acryloyloxy. In particular, from the viewpoint of improving the humid heat durability of lenses formed from the curable composition of the present invention, Pol is especially preferably methacryloyloxy.

[0228] Multiple Pols can be the same or different, but the same is preferred.

[0229] A polymerizable compound represented by the general formula (A0) is a compound having at least one polymerizable group, preferably at least two polymerizable groups. There is no particular limit to the upper limit of the number of polymerizable groups in a polymerizable compound represented by the general formula (A0), but for example, four or fewer are preferred.

[0230] Polymerizable compounds represented by general formula (A0) preferably have at least a polymerizable group as Pol, and more preferably have a polymerizable group only as Pol.

[0231] Pol 3 Hydrogen atoms are preferred.

[0232] As -Sp α -Pol 3 Preferably, it contains hydrogen atoms or alkyl groups having 1 to 4 carbon atoms, more preferably hydrogen atoms or unsubstituted alkyl groups having 1 to 4 carbon atoms.

[0233] Furthermore, in polymeric compounds represented by the general formula (A0), the plurality of Pol-Sp-L- can be the same or different, but are preferably the same.

[0234] As a specific example of a Pol-Sp-L- structure, the following structure can be cited.

[0235] R represents a hydrogen atom or a methyl group. Furthermore, * indicates the bonding position with Ar.

[0236] [Chemical Formula 12]

[0237]

[0238] (Compounds represented by the general formula (A1) or (A2))

[0239] As compounds containing the aforementioned nitrogen-containing fused aromatic rings, compounds represented by the following general formulas (A1) or (A2) are also preferred examples.

[0240] [Chemical Formula 13]

[0241]

[0242] In the above formula, R 3 and R 4 L represents a hydrogen atom or a monovalent substituent. 1 and L 2 Sp represents an alkylene group having 1 to 6 carbon atoms, an aryl group having 6 to 10 carbon atoms, or a heteroaryl group having 5 to 10 cyclic atoms. a ~Sp d This indicates a single bond or a divalent linker.

[0243] Pol 1 and Pol2 It represents a hydrogen atom or a polymeric group. Among them, Pol... 1 and Pol 2 At least one of them is a polymeric group.

[0244] Ring Ar 1 Ar represents an aromatic ring represented by the following formula (AR1), or a fused ring containing the aromatic ring as a constituent ring of a fused ring. 2 This represents an aromatic ring represented by the following formula (AR2), or a fused ring containing the aromatic ring as a constituent ring of a fused ring. Wherein, ring Ar 1 and the ring Ar 2 At least one of them is the aforementioned nitrogen-containing fused aromatic ring.

[0245] R 1 Indicates ring Ar 1 The substituents present in the cyclic atoms, R 2 Indicates ring Ar 2 The substituents present in the cyclic atoms.

[0246] v is an integer greater than or equal to 0. The largest number of v is the ring Ar. 1 The maximum number of substituents that a cyclic atom can have.

[0247] w is an integer greater than or equal to 0. The largest number of w is the ring Ar. 2 The maximum number of substituents that a cyclic atom can have.

[0248] The substituents, linking groups, and symbols in general formulas (A1) and (A2) will be explained in detail below.

[0249] (1)L 1 and L 2

[0250] L 1 and L 2 It represents an alkylene group having 1 to 6 carbon atoms, an arylene group having 6 to 10 carbon atoms, or a heteroarylene group having 5 to 10 cyclic atoms.

[0251] Able to serve as L 1 and L 2 The alkylene groups with 1 to 6 carbon atoms are preferably alkylene groups with 1 to 4 carbon atoms, and more preferably alkylene groups with 2 or 3 carbon atoms. The alkylene groups can be straight-chain or branched.

[0252] As L 1 or L 2 When using alkylene groups with 1 to 6 carbon atoms, a connecting sp is formed. a or Sp a With ring Ar 1 and the ring Ar2 The number of connecting atoms in the shortest molecular chain of the fused 5-membered ring is preferably 1 to 6, more preferably 1 to 4, and even more preferably 2 or 3.

[0253] Able to serve as L 1 and L 2 The arylene group with 6 to 10 carbon atoms used is preferably a phenylene group with 6 to 10 carbon atoms, and more preferably a phenylene group with 6 or 7 carbon atoms.

[0254] Able to serve as L 1 and L 2 The heteroarylene group with 5 to 10 cyclic atoms used is preferably a heteroarylene group with 5 to 10 cyclic atoms composed of a monocyclic ring.

[0255] As L 1 or L 2 When using arylene groups with 6 to 10 carbon atoms or heteroarylene groups with 5 to 10 cyclic atoms, a connecting sp group is formed. a or Sp a With ring Ar 1 and the ring Ar 2 The number of connecting atoms in the fused 5-membered ring molecular chain that forms the shortest molecular chain is preferably 2 to 6, more preferably 2 to 4.

[0256] Additionally, in L 1 or L 2 In the case of an alkylene group having 1 to 6 carbon atoms, to form L 1 and L 2 The number of carbon atoms in the alkylene group becomes the largest way to determine L. 1 and L 2 That is, in general formulas (A1) and (A2), it can be used as the following Sp a and Sp b The divalent linker used is related to L 1 or L 2 The bonded portion is not an alkylene group.

[0257] As can serve as the above L 1 and L 2 The alkylene group with 1 to 6 carbon atoms, the aryl group with 6 to 10 carbon atoms, or the heteroaryl group with 5 to 10 cyclic atoms that can be used may have substituents, such as alkyl, cycloalkyl, alkenyl, aryl, heteroaryl, alkoxy, acyl, acyloxy, alkoxycarbonyl, carbamoyl, amide, amino, halogen atom, hydroxyl, nitro, cyano, and groups derived from -Sp δ -Pol δ The group indicated.

[0258] Sp δThe Sp group represents a single bond or a divalent linker, applicable to the general formulas (A1) and (A2) described below. a The record. Pol δ It is a polymerizable group, capable of being used in the general formulas (A1) and (A2) described later. 1 The description of polymeric groups in the text.

[0259] As can serve as the above L 1 and L 2 The alkylene group with 1 to 6 carbon atoms may have substituents, preferably alkoxy, alkoxycarbonyl or groups represented by -Sp-Pol above, more preferably -COO-alkylene-Pol, and even more preferably -COO-alkylene-OCOCH=CH2 or -COO-alkylene-OCOC(CH3)=CH2.

[0260] In order to serve as the above L 1 and L 2 When the alkylene group with 1 to 6 carbon atoms has substituents, the number of substituents is not particularly limited. For example, it may have 1 to 4 substituents, preferably 1 or 2, and more preferably 1.

[0261] Able to serve as the above L 1 and L 2 The alkylene groups with 1 to 6 carbon atoms used are preferably without substituents.

[0262] As can serve as the above L 1 and L 2 The arylene group with 6 to 10 carbon atoms or the heteroarylene group with 5 to 10 cyclic atoms may have substituents, preferably halogen atoms, alkyl groups, alkoxy groups, aryl groups or cyano groups, more preferably halogen atoms, alkyl groups with 1 to 5 carbon atoms, alkoxy groups with 1 to 5 carbon atoms, phenyl groups or cyano groups, even more preferably halogen atoms, methyl groups, methoxy groups, phenyl groups or cyano groups, and particularly preferably methyl groups or methoxy groups.

[0263] Able to serve as the above L 1 and L 2 The number of substituents in the arylene group with 6 to 10 carbon atoms or the heteroarylene group with 5 to 10 cyclic atoms is preferably 0 or 1, and more preferably no substituents.

[0264] As mentioned above L 1 and L 2 Preferably, it is an alkylene group having 1 to 6 carbon atoms or an aryl group having 6 to 10 carbon atoms.

[0265] (2)Sp a and Sp b

[0266] Spa and Sp b This indicates a single bond or a divalent linker.

[0267] As a sp a or Sp b The divalent linking group used can be selected from linear alkylene, cycloalkylene, aryl, heteroaryl, -O-, -S-, >C(=O) and >NR. γ1 A divalent linker formed by the bonding of one or more groups in the group.

[0268] The above R γ1 It represents an alkyl group having 1 to 3 hydrogen atoms or carbon atoms.

[0269] Among them, those that can serve as Sp a and Sp b Among the divalent linking groups used, those with L 1 or L 2 The bonded portion is neither a straight-chain alkylene nor a cycloalkylene.

[0270] Able to act as Sp a and Sp b The linear alkylene groups used preferably have 1 to 8 carbon atoms, more preferably 1 to 6, even more preferably 1 to 4, and particularly preferably 1 or 2.

[0271] Able to act as Sp a and Sp b The number of carbon atoms in the cycloalkyl group used is preferably 3 to 6.

[0272] Able to act as Sp a and Sp b The number of carbon atoms in the arylene group used is preferably 6 to 10, more preferably 6.

[0273] Able to act as Sp a and Sp b The number of cyclic atoms in the heteroarylene group used is preferably 5 to 10, more preferably 5 to 7.

[0274] The number of carbon atoms in the aforementioned "straight-chain alkylene" refers to the number of carbon atoms in the unsubstituent state. When the "straight-chain alkylene" has substituents, the alkyl group can also be used as the substituent. In this case, it is considered a branched alkylene overall, but Sp... a and Sp b The connection L in 1 With Pol 1 、 or L 2 With Pol 2 The number of connecting atoms in the part corresponding to the shortest molecular chain corresponds to the "straight-chain alkylene" mentioned above.

[0275] The number of carbon atoms in "cycloalkylene" and "arylene" refers to the number of carbon atoms in the state after removing the substituents.

[0276] As mentioned above Sp a and Sp b The straight-chain alkylene, cycloalkylene, arylene or heteroarylene groups may have substituents, such as alkyl, cycloalkyl, alkoxy, acyl, acyloxy, alkoxycarbonyl, carbamoyl, amide, amino, halogen, nitro and cyano, preferably alkyl, more preferably alkyl with 1 to 3 carbon atoms, and even more preferably methyl.

[0277] The number of substituents is not particularly limited; for example, it can have 1 to 4 substituents.

[0278] Sp, which constitutes a divalent linker a and Sp b The above-mentioned straight-chain alkylene, cycloalkylene, arylene, heteroarylene, -O-, -S-, >C(=O) and >NR γ1 The types are not particularly limited, but 1 to 5 types are preferred, and 1 to 3 types are more preferred. Furthermore, even in the presence of multiple groups classified as linear alkylene groups, as constituents of Sp... a and Sp b The type of group is also calculated as a straight-chain alkylene group. For cycloalkylene, aryl, heteroaryl, or >NR groups... γ1 The same applies.

[0279] Sp, as a divalent linker a and Sp b In, it is represented as -O-, -S-, >C (=O), and >NR. γ1 Groups formed by the connection of two or more elements can be exemplified by -C(=O)O- and -NR. γ1 C(=O)-, -SC(=O)-, -OC(=O)O- or -NR γ1 C(=O)O-, preferably -C(=O)O- or -NR γ1 C(=O)- or -SC(=O)-, more preferably -C(=O)O-.

[0280] The above-O-, -S-, >C (=O) and >NR γ1 The group formed by the linkage of two or more chains in a Sp group, either alone or together with at least one of the linear alkylene, cycloalkylene, arylene, or heteroarylene groups, constitutes a divalent linking group. a and Sp b Preferably, it can be combined with at least one of linear alkylene, cycloalkylene, arylene, or heteroarylene to form a Sp group as a divalent linking group. a and Spb More preferably, it forms a Sp group as a divalent linking group together with at least one of a straight-chain alkylene or a cycloalkylene group. a and Sp b .

[0281] In addition, the above-mentioned -C(=O)O- and -NR γ1 C(=O)-、-NR γ1 C(=O)O- or -SC(=O-) can also be configured so that either the left or right connector is located at L. 1 Side or L 2 side.

[0282] To further increase the amount of cyclopentadiene skeleton in the compound and Ar 1 and Ar 2 From the perspective of the ratio of the fused structural parts, Sp a and Sp b The connection L in the middle 1 With Pol 1 、 or L 2 With Pol 2 The number of connecting atoms in the shortest molecular chain is preferably 1 to 14, more preferably 1 to 10, and even more preferably 1 to 8.

[0283] As Sp a and Sp b Preferably, it is a single bond or a divalent linker formed by one or more groups selected from linear alkylene, -O- and >C (=O), more preferably a divalent linker formed by one or more groups selected from linear alkylene, -O- and >C (=O).

[0284] Sp a With Sp b They can be the same or different, but the same is preferred.

[0285] (3)Sp c and Sp d

[0286] Sp c and Sp d This indicates a single bond or a divalent linker.

[0287] As a sp c or Sp d The divalent linking group used can be selected from linear alkylene, cycloalkylene, aryl, heteroaryl, -O-, -S-, >C(=O) and >NR. γ2 A divalent linker formed by the bonding of one or more groups in the group.

[0288] The above R γ2It represents an alkyl group having 1 to 3 hydrogen atoms or carbon atoms.

[0289] Able to act as Sp c and Sp d The linear alkylene groups used preferably have 1 to 8 carbon atoms, more preferably 1 to 6, even more preferably 1 to 4, and particularly preferably 1 or 2.

[0290] Able to act as Sp c and Sp d The number of carbon atoms in the cycloalkyl group used is preferably 3 to 6.

[0291] Able to act as Sp c and Sp d The number of carbon atoms in the arylene group used is preferably 6 to 10, more preferably 6.

[0292] Able to act as Sp c and Sp d The number of cyclic atoms in the heteroarylene group used is preferably 5 to 10, more preferably 5 to 7.

[0293] The number of carbon atoms in the aforementioned "straight-chain alkylene" refers to the number of carbon atoms in the unsubstituent state. When the "straight-chain alkylene" has substituents, the alkyl group can also be used as the substituent. In this case, it is considered as a branched alkylene as a whole, but Sp c and Sp d The connection between CR 3 With Pol 1 , or CR 3 With Pol 2 The number of connecting atoms in the part corresponding to the shortest molecular chain corresponds to the "straight-chain alkylene" mentioned above.

[0294] The number of carbon atoms in "cycloalkylene" and "arylene" refers to the number of carbon atoms in the state after removing the substituents.

[0295] As mentioned above Sp c and Sp d The straight-chain alkylene, cycloalkylene, arylene or heteroarylene groups may have substituents, such as alkyl, cycloalkyl, alkoxy, acyl, acyloxy, alkoxycarbonyl, carbamoyl, amide, amino, halogen, nitro and cyano, preferably alkyl, more preferably alkyl with 1 to 3 carbon atoms, and even more preferably methyl.

[0296] The number of substituents is not particularly limited; for example, it can have 1 to 4 substituents.

[0297] Sp, which constitutes a divalent linker c and Sp dThe above-mentioned straight-chain alkylene, cycloalkylene, arylene, heteroarylene, -O-, -S-, >C(=O) and >NR γ2 The types are not particularly limited, but 1 to 5 types are preferred, and 1 to 3 types are more preferred. Furthermore, even in the presence of multiple groups classified as linear alkylene groups, as constituents of Sp... c and Sp d The type of group is also calculated as a straight-chain alkylene group. For cycloalkylene, aryl, heteroaryl, or >NR groups... γ2 The same applies.

[0298] Sp, as a divalent linker c and Sp d In this context, - is composed of O-, -S-, >C (=O), and >NR. γ2 Groups formed by the connection of two or more elements can be exemplified by -C(=O)O- and -NR. γ2 C(=O)-, -SC(=O)-, -OC(=O)O- or -NR γ2 C(=O)O-, preferably -C(=O)O- or -NR γ2 C(=O)- or -SC(=O)-, more preferably -C(=O)O-.

[0299] The above consists of -O-, -S-, >C (=O) and >NR γ2 The group formed by the linkage of two or more chains in a Sp group, either alone or together with at least one of the linear alkylene, cycloalkylene, arylene, or heteroarylene groups, constitutes a divalent linking group. c and Sp d Preferably, it can be combined with at least one of linear alkylene, cycloalkylene, arylene, or heteroarylene to form a Sp group as a divalent linking group. c and Sp d More preferably, it forms a Sp group as a divalent linking group together with at least one of a straight-chain alkylene or a cycloalkylene group. c and Sp d .

[0300] In addition, the above-mentioned -C(=O)O- and -NR γ2 C(=O)-、-NR γ2 C(=O)O- or -SC(=O-) can also be configured so that either the left or right connection key is located in CR. 3 side.

[0301] To further increase the amount of cyclopentadiene skeleton in the compound and Ar 1 and Ar 2 From the perspective of the ratio of the fused structural parts, Sp c and Sp dThe connection of CR in the middle 3 With Pol 1 , or CR 3 With Pol 2 The number of connecting atoms in the shortest molecular chain is preferably 1 to 14, more preferably 1 to 10, even more preferably 1 to 8, and particularly preferably 1 to 6.

[0302] As Sp a and Sp b Preferably, it is a single bond or a divalent linker formed by bonding one or more groups selected from linear alkylene groups, -O- and >C (=O).

[0303] Sp c With Sp d They can be the same or different, but different is preferred.

[0304] As Sp c and Sp d , preferred Sp c and Sp d One of them is -alkylene-C(=O)O-alkylene-, and the other is -C(=O)O-alkylene-.

[0305] (4)R 3 and R 4

[0306] R 3 and R 4 It represents a hydrogen atom or a monovalent substituent.

[0307] As can be R 3 and R 4 Examples of monovalent substituents used include alkyl, cycloalkyl, alkoxy, acyl, acyloxy, alkoxycarbonyl, carbamoyl, amide, amino, halogen, nitro, and cyano, with alkyl being preferred.

[0308] Able to serve as R 3 and R 4 The alkyl group used preferably has 1 to 6 carbon atoms, more preferably 1 to 4, and even more preferably 1 or 2.

[0309] As R 3 and R 4 Hydrogen atoms are preferred.

[0310] (5)Pol 1 and Pol 2

[0311] Pol 1 and Pol 2 It represents a hydrogen atom or a polymeric group. Among them, Pol... 1 and Pol 2At least one of them is a polymeric group.

[0312] As a Pol 1 and Pol 2 The polymerizable groups used are applicable to the aforementioned general formula (A0) and can be used as Pol and Pol 3 The description of the polymeric groups used.

[0313] Pol 1 and Pol 2 Either of them is preferably (meth)acryloyloxy, more preferably both of them are (meth)acryloyloxy.

[0314] Pol 1 and Pol 2 They can be the same or different, but the same is preferred.

[0315] (6) Ring Ar 1 and the ring Ar 2

[0316] Ring Ar 1 Ar represents an aromatic ring represented by the following formula (AR1), or a fused ring containing the aromatic ring as a constituent ring of a fused ring. 2 This represents an aromatic ring represented by the following formula (AR2), or a fused ring containing the aromatic ring as a constituent ring of a fused ring. Wherein, ring Ar 1 and the ring Ar 2 At least one of them is the aforementioned nitrogen-containing fused aromatic ring.

[0317] In the ring of Ar 1 and the ring Ar 2 In the case of a fused ring, the number of ring elements in each ring constituting the fused ring is preferably 5 to 7, more preferably 5 or 6, and even more preferably 6. Specifically, in the ring Ar... 1 or ring Ar 2 In the case of the nitrogen-containing fused aromatic ring described above, the number of ring elements in each ring constituting the fused ring is 6.

[0318] Furthermore, in the ring of Ar 1 and the ring Ar 2 In the case of a fused ring, the number of rings constituting the fused ring is preferably 2 or 3, more preferably 2. Preferred ring Ar 1 and the ring Ar 2 One of them is a monocyclic ring represented by the following formula (AR1) or (AR2), and the other is a fused ring. The number of rings constituting the fused ring is preferably 2.

[0319] The cyclic atoms that constitute the fused ring, other than the ring represented by the following formula (AR1) or (AR2), are preferably carbon atoms, oxygen atoms, sulfur atoms or nitrogen atoms, more preferably carbon atoms or nitrogen atoms, and even more preferably carbon atoms.

[0320] The ring that constitutes the fused ring is other than the ring represented by the following formula (AR1) or (AR2), such as a benzene ring or a pyridine ring.

[0321] [Chemical Formula 14]

[0322]

[0323] In the above formula, X 11 Y 11 X 12 and Y 12 It represents an oxygen atom, a sulfur atom, a nitrogen atom, or a carbon atom.

[0324] Z 11 Indicates -X 11 -C=CY 11 -Together they form a 5- to 7-membered aromatic ring and are composed of atoms selected from oxygen, sulfur, nitrogen and carbon atoms.

[0325] Z 12 Indicates -X 12 -C=CY 12 -Together they form a 5- to 7-membered aromatic ring and are composed of atoms selected from oxygen, sulfur, nitrogen and carbon atoms.

[0326] * Equivalent to the double bond of the cyclopentadiene ring in general formulas (A1) to (A4). That is, the cyclopentadiene ring and the cycloAr ring... 1 and the ring Ar 2 They are densely connected by sharing the edges represented by *.

[0327] (X 11 Y 11 X 12 and Y 12 )

[0328] The above X 11 Y 11 X 12 and Y 12 It represents an oxygen atom, a sulfur atom, a nitrogen atom, or a carbon atom, preferably a nitrogen atom or a carbon atom.

[0329] Among them, in the ring Ar described later 1 In the case of a single ring, X 11 and Y 11 Preferably, all are carbon atoms, in the Ar ring described later. 1 In the case of a fused ring, X 11 and Y 11 Preferably, at least one is a nitrogen atom, and more preferably, all of them are nitrogen atoms.

[0330] Similarly, in the ring Ar described later2 In the case of a single ring, X 12 and Y 12 Preferably, all are carbon atoms, in the Ar ring described later. 2 In the case of a fused ring, X 12 and Y 12 Preferably, at least one is a nitrogen atom, and more preferably, all of them are nitrogen atoms.

[0331] (Z 11 and Z 12 )

[0332] Z 11 Is with -X 11 -C=CY 11 - A group of atoms that together form a 5- to 7-membered aromatic ring, preferably a group of atoms that form a 5- or 6-membered aromatic ring, more preferably a group of atoms that form a 6-membered aromatic ring.

[0333] Z 12 Is with -X 12 -C=CY 12 - A group of atoms that together form a 5- to 7-membered aromatic ring, preferably a group of atoms that form a 5- or 6-membered aromatic ring, more preferably a group of atoms that form a 6-membered aromatic ring.

[0334] Z 11 and Z 12 It is an atomic group composed of atoms selected from oxygen, sulfur, nitrogen, and carbon atoms. 11 and Z 12 Preferably, it is an atomic group composed of atoms selected from oxygen atoms, sulfur atoms, nitrogen atoms and carbon atoms, and containing at least carbon atoms; more preferably, it is an atomic group composed of atoms selected from nitrogen atoms and carbon atoms, and containing at least carbon atoms; and even more preferably, it is an atomic group composed of carbon atoms.

[0335] (7)R 1 and R 2

[0336] R 1 Indicates ring Ar 1 The substituents present in the cyclic atoms, R 2 Indicates ring Ar 2 The substituents present in the cyclic atoms. In R 1 and R 2 They are respectively in the ring of Ar 1 or ring Ar 2 Substituents that a nitrogen or carbon atom, expressed by NH or CH, may have in the unsubstituted cyclic atom.

[0337] As can be R 1 and R 2The substituents used are not particularly limited, and examples include halogen atoms, alkyl groups, acyl groups, hydroxyl groups, alkoxy groups, aromatic hydrocarbon cyclogroups, or cyano groups.

[0338] Ring Ar 1 R in 1 Replacement position and ring Ar 2 R in 2 The replacement position is not particularly restricted.

[0339] Able to serve as R 1 and R 2 The alkyl group used preferably has 1 to 5 carbon atoms, more preferably 1 to 3, and even more preferably 1.

[0340] Able to serve as R 1 and R 2 The number of carbon atoms in the alkoxy group used is preferably 1 to 5, more preferably 1 to 3, and even more preferably 1.

[0341] Able to serve as R 1 and R 2 The aromatic hydrocarbon cyclic group used preferably has 6 to 14 carbon atoms, more preferably 6 to 10.

[0342] As can be R 1 and R 2 The halogen atom used is preferably a fluorine atom, a chlorine atom, or a bromine atom, with a chlorine atom being more preferred.

[0343] R 1 and R 2 The preferred radicals are halogen atoms, alkyl groups, alkoxy groups, aromatic hydrocarbon groups or cyano groups, more preferably halogen atoms, alkyl groups with 1 to 5 carbon atoms or alkoxy groups with 1 to 5 carbon atoms, and even more preferably halogen atoms, methyl groups or methoxy groups.

[0344] (8) v and w

[0345] v is an integer greater than or equal to 0. The largest number of v is the ring Ar. 1 The maximum number of substituents that a cyclic atom can have.

[0346] w is an integer greater than or equal to 0. The largest number of w is the ring Ar. 2 The maximum number of substituents that a cyclic atom can have.

[0347] v and w are preferably integers from 0 to 4, and more preferably integers from 0 to 2.

[0348] The sum of v and w is preferably an integer from 0 to 4, and more preferably an integer from 0 to 2.

[0349] The preferred compound containing the nitrogen-containing fused aromatic ring is a compound represented by the above general formula (A1), and more preferably a compound represented by the following general formula (A11).

[0350] [Chemical Formula 15]

[0351]

[0352] In the above formula, X a and X b This represents a nitrogen atom or CH, where the CH at the # position can be replaced by a nitrogen atom. Where X... a X b At least one of the CH atoms at the # position is a nitrogen atom.

[0353] R 11 and R 21 Represents substituents, where v1 and w1 are integers from 0 to 4. R 101 and R 102 It represents a hydrogen atom or a methyl group.

[0354] L 1 L 2 Sp a and Sp b The meanings are respectively the same as L in the above general formula (A1) 1 L 2 Sp a and Sp b The meanings are the same.

[0355] v1 and w1 are preferably integers from 0 to 2.

[0356] As can be R 11 and R 21 The substituents used are suitable for use as R 1 and R 2 The substituents used are described.

[0357] Additionally, R 21 It is X a and X b The carbon atoms in CH and the carbon atoms in CH at the # position can have substituents.

[0358] As having R 11 Or R 21 R at that time 11 Or R 21 The replacement position is not particularly limited, but it is preferably located in the position indicated by the following structure.

[0359] [Chemical Formula 16]

[0360]

[0361] X a and X b Preferably, at least one is a nitrogen atom, and more preferably, all of them are nitrogen atoms.

[0362] Furthermore, preferably, none of the CH atoms at the # position are replaced by nitrogen atoms, or one of them is replaced by a nitrogen atom; more preferably, none of them are replaced by nitrogen atoms.

[0363] Among them, X, as a compound represented by the general formula (A11), a X b At least one of CH at the # position is a nitrogen atom, preferably X. a and X b At least one of them is a nitrogen atom.

[0364] That is, the compound represented by the above general formula (A11) is more preferably a compound represented by the following general formula (A11a) or (A11b), and even more preferably a compound represented by the following general formula (A11b).

[0365] [Chemical Formula 17]

[0366]

[0367] In the above formula, R 11 R 21 R 101 R 102 L 1 L 2 Sp a Sp b The meanings of v1 and w1 are respectively the same as R in the above general formula (A11). 11 R 21 R 101 R 102 L 1 L 2 Sp a Sp b v1 and w1 have the same meaning.

[0368] One of the CH atoms at position # is replaced by a nitrogen atom.

[0369] As for compounds containing the aforementioned nitrogen-fused aromatic rings, from the viewpoint of further improving lightfastness, compounds represented by the aforementioned general formula (A1) or (A2) are more preferred, and compounds represented by the aforementioned general formula (A1) are even more preferred.

[0370] The method for obtaining the compound containing a nitrogen-containing fused aromatic ring, which is component A, is not particularly limited; commercially available products or compounds obtained through synthesis may be used. In the case of obtaining it through synthesis, the method for manufacturing the compound containing the aforementioned nitrogen-containing fused aromatic ring is not particularly limited; it can be manufactured according to conventional methods, referring to the methods described in the examples below.

[0371] [Polymers having structural units containing nitrogen-containing fused aromatic rings]

[0372] (Polymers having structural units represented by general formula (A3) or (A4))

[0373] As a polymer having a structural unit comprising the above-mentioned nitrogen-containing fused aromatic ring, a polymer having a structural unit represented by the following general formula (A3) or (A4) is preferably mentioned.

[0374] [Chemical Formula 18]

[0375]

[0376] In the above formula, R 1 ~R 4 L 1 L 2 Sp a ~Sp d , Ring Ar 1 , Ring Ar 2 The meanings of , v and w are respectively the same as R in the above general formulas (A1) and (A2). 1 ~R 4 L 1 L 2 Sp a ~Sp d , Ring Ar 1 , Ring Ar 2 The meanings of , v, and w are the same.

[0377] LL represents a single bond or a divalent linker, and X represents an oxygen atom (-O-), a carbonyl group (>C=O), or an amino group (>NR). γ4 R γ4 (This represents a hydrogen atom or a substituent.) or a group consisting of two of them.

[0378] n is an integer from 0 to 5.

[0379] Examples of divalent linking groups that can be used as LL include those selected from alkylene, cycloalkylene, arylene, heteroarylene, -O-, -S-, >C(=O), and >NR. γ3 A divalent linker formed by the bonding of one or more of the following.

[0380] The above R γ3 It represents an alkyl group having 1 to 3 hydrogen atoms or carbon atoms.

[0381] The number of carbon atoms in the alkylene group that can be used as LL is preferably 1 to 8, more preferably 1 to 6, even more preferably 1 to 4, and particularly preferably 1 or 2.

[0382] The number of carbon atoms in the cycloalkyl group that can be used as LL is preferably 3 to 6.

[0383] The number of carbon atoms in the arylene group that can be used as LL is preferably 6 to 10, more preferably 6.

[0384] The number of cyclic atoms of the heteroarylene group that can be used as LL is preferably 5 to 10, more preferably 5 to 7.

[0385] As a substituent that can be present as the alkylene, cycloalkylene, arylene, or heteroarylene groups in the aforementioned LL, examples can be given of substituents that can be present as the aforementioned L 1 and L 2 The group used may have substituents or be able to act as the aforementioned Sp. a and Sp b The group used may have substituents, preferably alkyl, more preferably alkyl with 1 to 3 carbon atoms, and even more preferably methyl.

[0386] In amino groups that can be used as X (>NR) γ4 In ), R γ4 It represents a hydrogen atom or a substituent, preferably a hydrogen atom or an alkyl group.

[0387] X is preferred as -O-, >C=O or -C(=O)O-.

[0388] n is preferably an integer from 0 to 2, and more preferably an integer of 0 or 1.

[0389] In the structural unit represented by the above general formula (A3) or (A4), when n = 0, it becomes a structural unit represented by the following general formula (A3a) or (A4a).

[0390] [Chemical Formula 19]

[0391]

[0392] In the above formula, R 1 ~R 4 L 1 L 2 Sp a ~Sp d , Ring Ar 1 , Ring Ar 2 The meanings of , v and w are respectively the same as R in the above general formulas (A1) and (A2). 1~R 4 L 1 L 2 Sp a ~Sp d , Ring Ar 1 , Ring Ar 2 The meanings of v and w are the same, and the meaning of X is the same as that of X in the above general formulas (A3) and (A4).

[0393] The following are specific examples of structural units represented by general formulas (A3a) or (A4a), but are not limited to the following structural units.

[0394] [Chemical Formula 20]

[0395]

[0396] The method for obtaining the structural unit represented by the above general formula (A3a) or (A4a) is not particularly limited; the precursor compound can be obtained commercially or synthesized. Furthermore, the above-mentioned compound containing a nitrogen-containing fused aromatic ring can be used as the precursor compound.

[0397] In the structural unit represented by the above general formula (A3) or (A4), when n is an integer from 1 to 5, it is preferable to take the structural unit represented by the following general formula (A3b) or (A4b).

[0398] [Chemical Formula 21]

[0399]

[0400] In the above formula, R 1 ~R 4 L 1 L 2 Sp a ~Sp d , Ring Ar 1 , Ring Ar 2 The meanings of , n, v and w are respectively the same as R in the above general formulas (A1) and (A2). 1 ~R 4 L 1 L 2 Sp a ~Sp d , Ring Ar 1 , Ring Ar 2 The meanings of , n, v and w are the same, and the meaning of X is the same as that of X in the above general formulas (A3) and (A4).

[0401] LL 1 Indicates a single bond or an alkylene group.

[0402] As a being able to serve as LL 1 The alkylene compounds used can be those described as being suitable for use in the above-mentioned LL.

[0403] The method for obtaining the structural unit represented by the above general formula (A3b) or (A4b) is not particularly limited. The precursor compound can be obtained by commercial means or it can be manufactured by synthesis. For example, according to the synthesis method described in Japanese Patent Application Publication No. 2021-1328, it can be manufactured by conventional methods with reference to the methods described in the examples described later.

[0404] Polymers having structural units comprising the aforementioned nitrogen-containing fused aromatic rings preferably also contain structural units other than those represented by the above general formulas (A3) or (A4) (hereinafter also referred to as "other structural units").

[0405] As other structural units, structural units represented by the following general formula (11) can be preferred.

[0406] [Chemical Formula 22]

[0407]

[0408] In general formula (11), R 11 It is a group comprising at least one selected from alkylene groups having 2 to 8 carbon atoms, cycloalkylene groups having 5 to 20 carbon atoms, aryl groups having 6 to 40 carbon atoms, and heteroaryl groups having 6 to 40 carbon atoms. Preferably, the alkylene, cycloalkylene, aryl, and heteroaryl groups have substituents, and the carbon atoms of the alkylene and cycloalkylene groups can be replaced by oxygen or sulfur atoms.

[0409] R 11 Any linking group containing the above-mentioned groups is acceptable. It can be a linking group composed of the above-mentioned groups, or a linking group having a structure formed by combining two or more of the above-mentioned groups. Furthermore, R... 11 Alternatively, a linking group selected from at least one of ether bonds and thioether bonds may be included between the aforementioned groups. In this case, at least one of the ether bonds and thioether bonds may exist between groups of the same kind or between groups of different kinds.

[0410] Among them, R 11 It does not contain a group containing -OC(=O)-O-.

[0411] Among them, R 11 Preferably, it is a cycloalkylene group having 5 to 20 carbon atoms, and more preferably, it is a cycloalkylene group having 5 to 15 carbon atoms.

[0412] The following are specific examples of structural units represented by general formula (11), but are not limited to the structures described below. In addition, in the following specific examples, * indicates the connection points with other structural units.

[0413] [Chemical Formula 23]

[0414]

[0415] [Chemical Formula 24]

[0416]

[0417] In addition to the structural unit represented by the general formula (11) above, polymers having structural units containing the nitrogen-containing fused aromatic rings as described above also preferably contain structural units represented by the following formula (s) as other structural units.

[0418] [Chemical Formula 25]

[0419]

[0420] The introduction (synthesis) of other structural units into polymers having structural units containing the above-mentioned nitrogen-containing fused aromatic rings is not particularly limited and can be carried out by conventional methods, such as the method described in Japanese Patent Application Publication No. 2021-1328.

[0421] In a polymer having a structural unit comprising the above-described nitrogen-containing fused aromatic ring, the structural unit occupying the polymer may be a structural unit represented by the above-described general formula (A3) or (A4), or may further comprise the above-described other structural units.

[0422] When a polymer having a structural unit containing the above-mentioned nitrogen-containing fused aromatic ring contains the above-mentioned other structural units, the proportion of the structural unit represented by the above-mentioned general formula (A3) or (A4) in the polymer having a structural unit containing the above-mentioned nitrogen-containing fused aromatic ring is preferably 10 to 95% by mass, more preferably 10 to 90% by mass, and even more preferably 15 to 85% by mass.

[0423] In the case of having a structural unit represented by the above general formula (11), the proportion of the structural unit represented by the above general formula (11) in the polymer having a structural unit containing the above nitrogen-containing fused aromatic ring is preferably 5 to 90% by mass, more preferably 10 to 80% by mass, and even more preferably 15 to 75% by mass.

[0424] In the case of having a structural unit represented by the above formula (s), the proportion of the structural unit represented by the above formula (s) in the polymer having a structural unit containing the above nitrogen-containing fused aromatic ring is preferably 1 to 20% by mass, more preferably 2 to 15% by mass, and even more preferably 3 to 10% by mass.

[0425] The weight-average molecular weight (Mw) of the polymer having structural units comprising the aforementioned nitrogen-containing fused aromatic rings is preferably 5,000 or more, more preferably 10,000 or more, and even more preferably 13,000 or more. Furthermore, the upper limit of the weight-average molecular weight is preferably 200,000 or less, more preferably 150,000 or less, and even more preferably 100,000 or less.

[0426] In this invention, as described in polymer B of the lens adhesive described later, the mass-average molecular weight is a value determined by conversion using GPC as a standard polystyrene.

[0427] From the viewpoint of further improving lightfastness, component A is preferably a compound represented by the above general formula (A1) or (A2) or a polymer having a structural unit represented by the above general formula (A3) or (A4), and more preferably a compound represented by the above general formula (A1).

[0428] Component A is preferably a non-liquid crystal compound. That is, from the viewpoint of use as a lens material, it is a polymeric compound represented by any one of the above general formulas (A0) to (A2) and a polymer having a structural unit represented by the above general formula (A3) or (A4). 1 L 2 LL, Sp α Sp a ~Sp d Preferably, all are linking groups without ring structures.

[0429] The following are specific examples of component A preferably used in the compositions of the present invention, but are not limited to the following polymeric compounds or polymers. Additionally, in the following structural formulas, Me represents methyl, Et represents ethyl, iPr represents isopropyl, nPr represents n-propyl, nBu represents n-butyl, and tBu represents tert-butyl.

[0430] Furthermore, in polymers (P-3) and (P-4), -[XY]- represents the structural unit that can be used as "X" and the structural unit that can be used as "Y," respectively. The presence of multiple structural units represented by -[XY]- in the polymer is possible, provided that either X or Y is used. This also applies to polymers (P-3) and (P-4) that have structural units represented by -[XY]-.

[0431] [Chemical Formula 26]

[0432]

[0433] [Chemical Formula 27]

[0434]

[0435] [Chemical Formula 28]

[0436]

[0437] [Chemical Formula 29]

[0438]

[0439] [Chemical Formula 30]

[0440]

[0441] [Chemical Formula 31]

[0442]

[0443] [Chemical Formula 32]

[0444]

[0445] [Chemical Formula 33]

[0446]

[0447] [Chemical Formula 34]

[0448]

[0449] [Chemical Formula 35]

[0450]

[0451] [Chemical Formula 36]

[0452]

[0453] The content of component A in the composition of the present invention is preferably 30 to 99% by mass in the total solids content of the composition, more preferably 35 to 99% by mass, and even more preferably 40 to 99% by mass. By keeping the content of component A within the above range, a partial dispersion ratio (θg, F value) higher than the predicted partial dispersion ratio (θg, F value) can be easily achieved in the cured product having a specified Abbe number.

[0454] When the composition of the present invention contains two or more components A, it is preferable that their total content is within the above-mentioned range.

[0455] [Component B: A compound represented by any one of the following general formulas (B1) to (B5)]

[0456] The composition of the present invention contains component A, which is a compound having a nitrogen-containing fused aromatic ring as part of its structure, and component B, which is a compound represented by any one of the following general formulas (B1) to (B5). As mentioned above, component B acts as a quencher and is a compound that is not prone to undergoing [2+2] photocycloaddition reaction, and therefore exhibits excellent lightfastness.

[0457] [Chemical Formula 37]

[0458]

[0459] In the above formula, Ar 101 ~Ar 104 X represents aryl or heteroaryl. 1 Y represents a monovalent substituent. 1 This indicates a hydrogen atom or a monovalent substituent. Ar 101 ~Ar 104 X 1 and Y 1 Two adjacent elements in the loop can bond together to form a ring. Among them, the element that can serve as X... 1 Or Y 1 The monovalent substituents used are not aryl or heteroaryl.

[0460] For those who can serve as Ar 101 ~Ar 104 Unless otherwise specified, the aryl group used may preferably be a monovalent aromatic hydrocarbon group at the beginning of the label.

[0461] More preferably, the number of carbon atoms is 6 to 10, and more preferably, the ring constituting the aryl group is a monocyclic ring.

[0462] As an ability to serve as Ar 101 ~Ar 104 The aryl group used is more preferably phenyl, 1-naphthyl or 2-naphthyl, and even more preferably phenyl.

[0463] For those who can serve as Ar 101 ~Ar 104 Unless otherwise specified, the heteroaryl group used may preferably be a monovalent aromatic heterocyclic group at the beginning of the label.

[0464] Preferably, the aromatic heterocyclic group has carbon and nitrogen or sulfur atoms as cyclic atoms, more preferably an aromatic heterocyclic group has carbon and nitrogen atoms as cyclic atoms. The number of cyclic atoms is preferably 5 to 10, more preferably 5 or 6 (that is, the ring constituting the heteroaryl group is preferably a monocyclic ring).

[0465] As an ability to serve as Ar 101 ~Ar 104The heteroaryl group used is more preferably pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl or thiopheneyl, further preferably pyridyl, pyrazinyl, pyrimidinyl or pyridazinyl, and particularly preferably pyridyl.

[0466] Able to serve as Ar 101 ~Ar 104 The aryl and heteroaryl groups used can be unsubstituted or have substituents.

[0467] As an ability to serve as Ar 101 ~Ar 104 Examples of substituents that the aryl or heteroaryl group may have include alkyl groups with 1 to 6 carbon atoms, alkenyl groups with 2 to 6 carbon atoms, alkoxy groups with 1 to 6 carbon atoms, alkenyloxy groups with 2 to 6 carbon atoms, alkoxycarbonyl groups with 2 to 6 carbon atoms, acyl groups with 2 to 6 carbon atoms, alkylcarbonyloxy groups with 2 to 6 carbon atoms, halogen atoms (fluorine atoms, chlorine atoms, bromine atoms, etc.), hydroxyl groups, cyano groups, nitro groups, nitroso groups, or carboxyl groups. Among these, alkyl groups with 1 to 6 carbon atoms, alkoxy groups with 1 to 6 carbon atoms, halogen atoms, or hydroxyl groups are preferred, and alkoxy groups with 1 to 6 carbon atoms, halogen atoms, or hydroxyl groups are more preferred.

[0468] For those who can serve as Ar 101 ~Ar 104 The aryl or heteroaryl groups used may have the above-mentioned substituents, and unless otherwise specified, the corresponding groups at the beginning are preferably applicable.

[0469] Furthermore, as an entity capable of serving as Ar 101 ~Ar 104 The aryl or heteroaryl groups used may have the aforementioned substituents, and preferably have a partial structure represented by any one of the formulas (Pol-1) to (Pol-6) described below. As specific examples, alkoxy groups having a partial structure represented by any one of the formulas (Pol-1) to (Pol-6) described below, and alkoxycarbonyl groups having a partial structure represented by any one of the formulas (Pol-1) to (Pol-6) described below are preferred.

[0470] As Ar 101 ~Ar 104 More preferably, the ring constituting the aryl or heteroaryl group is a monocyclic aryl or heteroaryl group.

[0471] As can be X 1 Examples of monovalent substituents used include alkyl, alkenyl, cycloalkyl, cycloalkenyl, alkoxy, alkenyloxy, alkoxycarbonyl, cyano, or formyl.

[0472] For those who can be X 1Unless otherwise specified, the alkyl, alkenyl, cycloalkyl, cycloalkenyl, alkoxy, alkenyloxy, and alkoxycarbonyl groups used are preferably those beginning with alkyl, alkenyl, cycloalkyl, cycloalkenyl, alkoxy, alkenyloxy, and alkoxycarbonyl.

[0473] Able to serve as X 1 The alkyl group used preferably has 1 to 10 carbon atoms, more preferably 1 to 8. In addition, if it does not have a partial structure represented by any of the formulas (Pol-1) to (Pol-6) described later, it is further preferred to have 1 to 6, particularly preferred to have 1 to 4, and most preferably 1 or 2.

[0474] Able to serve as X 1 The number of carbon atoms in the alkenyl group used is preferably 2 to 6, more preferably 2 to 4, and even more preferably 2.

[0475] Able to serve as X 1 The cycloalkyl group used preferably has 3 to 15 carbon atoms, more preferably 5 to 12, and even more preferably 6 to 10.

[0476] Able to serve as X 1 The cycloalkenyl group used preferably has 4 to 15 carbon atoms, more preferably 5 to 12, and even more preferably 6 to 10.

[0477] For those who can be X 1 The number of carbon atoms in the alkyl portion of the alkoxy and alkoxycarbonyl groups used, and the number of carbon atoms that can be used as X above. 1 The recorded number of carbon atoms in the alkyl group has the same meaning.

[0478] For those who can be X 1 The number of carbon atoms in the alkenyl moiety of the alkene oxide used is related to the number of carbon atoms that can be used as X. 1 The recorded number of carbon atoms in the alkenyl group has the same meaning.

[0479] In being able to serve as X 1 In the above examples of substituents used, as examples of substituents that each substituent may have, it is possible to apply substituents that can be used as the above Ar 101 ~Ar 104 Examples of substituents that the aryl or heteroaryl groups used can have. [These can be] used as X. 1 The substituents used preferably have a partial structure represented by any one of the formulas (Pol-1) to (Pol-6) described later. As a specific example, an alkoxycarbonyl group having a partial structure represented by any one of the formulas (Pol-1) to (Pol-6) described later is preferably provided.

[0480] As X 1Preferably, it is alkyl, alkoxycarbonyl, cyano, formyl, alkoxy or alkylcarbonyloxy, more preferably alkyl, alkoxycarbonyl, cyano or formyl, and even more preferably alkoxycarbonyl, cyano or formyl.

[0481] As can be Y 1 The monovalent substituent used is suitable for use as the aforementioned X 1 The record of the monovalent substituent used.

[0482] Y 1 The term represents a hydrogen atom or a monovalent substituent, preferably a hydrogen atom, alkyl, alkoxycarbonyl, cyano, formyl, alkoxy, or alkylcarbonyloxy, more preferably a hydrogen atom, alkyl, alkoxycarbonyl, cyano, or formyl, and even more preferably a hydrogen atom, alkoxycarbonyl, cyano, or formyl.

[0483] Ar 101 ~Ar 104 X 1 and Y 1 Two adjacent elements in a loop can bond together to form a ring, for example, Ar. 101 ~Ar 104 The two adjacent ones in the middle are bonded to each other, and Ar 101 ~Ar 104 The preferred way for two adjacent atoms in Ar to form a fluorene ring is... 101 and Ar 102 bonded together, with Ar 101 and Ar 102 The way they form fluorene rings together.

[0484] Furthermore, in this invention, Ar is preferred. 101 ~Ar 104 X 1 and Y 1 Two adjacent elements in the array are not bonded to each other.

[0485] Furthermore, in this invention, component B preferably does not have a siloxane structure.

[0486] From the viewpoint of further improving lightfastness, the above-mentioned component B is preferably a compound represented by any one of the following general formulas (B11), (B41) or (B51).

[0487] [Chemical Formula 38]

[0488]

[0489] In the above formula, R 201 ~R 204 Represents substituents, where n1 to n4 are integers from 0 to 5, and X 2 Y represents a monovalent substituent. 2and Y 3 This represents a hydrogen atom or a monovalent substituent. Among them, those that can act as X... 2 Y 2 Or Y 3 The monovalent substituents used are not aryl or heteroaryl.

[0490] As can be R 201 ~R 204 The substituents used are suitable for use as the aforementioned Ar 101 ~Ar 104 The aryl or heteroaryl groups used may have substituents as described.

[0491] As can be X 2 The monovalent substituent used is suitable for use as the aforementioned X 1 The record of the monovalent substituent used.

[0492] As can be Y 2 and Y 3 The monovalent substituent used is suitable for use as the aforementioned Y 1 The record of the monovalent substituent used.

[0493] As Y 2 Preferably, a monovalent substituent is used; more preferably, an alkyl, alkoxycarbonyl, cyano, formyl, alkoxy, or alkylcarbonyloxy group is used; even more preferably, an alkyl, alkoxycarbonyl, cyano, or formyl group is used; and particularly preferably, an alkoxycarbonyl, cyano, or formyl group is used.

[0494] As Y 3 It is possible to preferentially apply the above-mentioned Y 1 The records.

[0495] n1 to n4 are preferably integers from 0 to 2, more preferably integers of 0 or 1, and even more preferably 0.

[0496] Furthermore, in this invention, R is preferred. 201 ~R 204 Two adjacent elements in the array are not bonded to each other.

[0497] From the viewpoint of further improving lightfastness, component B is more preferably Y in the compound represented by the above general formula (B11). 2 Compounds with a monovalent substituent or compounds represented by the above general formula (B41).

[0498] Furthermore, from the viewpoint of obtaining a cured or molded article exhibiting excellent lightfastness, and consequently, optical components containing such a cured or molded article exhibiting excellent durability (excellent durability against thermal stresses such as thermal shock), the aforementioned component B is preferably a compound represented by any one of the above general formulas (B11), (B41), or (B51), and is R in the above general formula (B11). 201 R 202 X 2 and Y 2 At least one of them, R in the above general formula (B41) 201 ~R 203 and Y 3 At least one of them, R in the above general formula (B51) 201 ~R 204 At least one of the compounds having a partial structure represented by any one of the following general formulas (Pol-1) to (Pol-6).

[0499] [Chemical Formula 39]

[0500]

[0501] * indicates the bonding location.

[0502] Compounds represented by any one of the above general formulas (B11), (B41) or (B51) preferably have a partial structure represented by any one of the above general formulas (Pol-1) to (Pol-6) as -L in the following general formula (B12). a -Sp g -Pol 7 The substituents are indicated.

[0503] The number of partial structures represented by any one of the above general formulas (B11), (B41) or (B51) in a compound is not particularly limited as long as the excellent lightfastness and excellent durability described above can be obtained, but is preferably one or two, more preferably one.

[0504] In the above general formula (B11), X is more preferred. 2 and Y 2 At least one of them has a partial structure represented by any one of the above general formulas (Pol-1) to (Pol-6), and in the above general formula (B41), R is more preferred. 201 ~R 203 At least one of them has a partial structure represented by any one of the above general formulas (Pol-1) to (Pol-6), and in the above general formula (B51), R is more preferred. 201 ~R 204At least one of them has a partial structure represented by any one of the above general formulas (Pol-1) to (Pol-6).

[0505] Wherein, component B is a compound represented by the above general formula (B11), more preferably X. 2 and Y 2 At least one of the compounds having a partial structure represented by any one of the above general formulas (Pol-1) to (Pol-6), and more preferably a compound represented by the following general formula (B12).

[0506] [Chemical Formula 40]

[0507]

[0508] In the above formula, L a Represents single bonds, -O-, -C(=O)-, -C(=O)O-, alkylene groups, and -CR. β1 =CR β2 - Cycloalkyl or cycloalkylene groups. The right side of the above -C(=O)O- is related to Sp g Bonding. The right side of -C(=O)O- refers to the ether bonding side.

[0509] R β1 and R β2 It represents a hydrogen atom or a monovalent substituent.

[0510] Sp g Indicates a single bond or a divalent linker, Pol 7 It is a group represented by any one of the above general formulas (Pol-1) to (Pol-6).

[0511] Among them, in L a In the case of a single key, Sp g It is a single key.

[0512] R 201 R 202 n1, n2 and Y 2 The meanings are respectively the same as R in the above general formula (B11). 201 R 202 n1, n2 and Y 2 The meanings are the same.

[0513] Regarding the ability to serve as L a The number of carbon atoms in the cycloalkyl and cycloalkenyl groups used is sufficient to make them suitable as X 1 The number of carbon atoms of the cycloalkyl and cycloalkenyl groups used is recorded.

[0514] L a The preferred choice is -C(=O)- or -C(=O)O-.

[0515] As can be R β1 and R β2 The monovalent substituent used is suitable for use as the aforementioned Ar 101 ~Ar 104 The aryl or heteroaryl groups used may have substituents as described.

[0516] As R β1 and R β2 Preferably, hydrogen atoms or alkyl groups are used.

[0517] As a sp g The divalent linking group used is not particularly limited; for example, alkylene groups can be used, preferably alkylene groups with 1 to 6 carbon atoms, and more preferably alkylene groups with 1 to 4 carbon atoms.

[0518] As Sp g Preferably, it is a single bond or an alkylene group, more preferably a single bond or an alkylene group having 1 to 6 carbon atoms, and even more preferably a single bond or an alkylene group having 1 to 4 carbon atoms.

[0519] -L a -Sp g - Preferably, -C(=O)- or -C(=O)O-alkylene-, more preferably -C(=O)- or -C(=O)O-alkylene- with 1 to 6 carbon atoms, and even more preferably -C(=O)- or -C(=O)O-alkylene- with 1 to 4 carbon atoms.

[0520] Preferred Pol 7 It is (meth)acryloyloxy, represented by the above formula (Pol-1) or formula (Pol-2).

[0521] Hereinafter, specific examples of compounds represented by any one of general formulas (B1) to (B5) that are preferably used in the compositions of the present invention are given, but are not limited to the following compounds.

[0522] [Chemical Formula 41]

[0523]

[0524] [Chemical Formula 42]

[0525]

[0526] [Chemical Formula 43]

[0527]

[0528] From the viewpoint of further improving lightfastness, the content of component B in the composition of the present invention is preferably 1% by mass or more, more preferably 3% by mass or more, and even more preferably 5% by mass or more in the total solids content of the composition. Furthermore, from the viewpoint of further improving durability against thermal stresses such as thermal shock, it is preferably 50% by mass or less, more preferably 45% by mass or less, and even more preferably 40% by mass or less. By keeping the content of component B within the above-mentioned preferred range, the cured product or molded article obtained from the composition of the present invention can possess both excellent lightfastness and optical properties (low Abbe number and high partial dispersion ratio), and optical components using the cured product or molded article can express excellent durability against thermal stresses such as thermal shock. For example, a preferred example is that the content of component B in the composition of the present invention is 1 to 30% by mass in the total solids content of the composition.

[0529] Furthermore, in the composition of the present invention, the content of component B is preferably 2 to 80 parts by mass relative to 100 parts by mass of component A, more preferably 5 to 70 parts by mass, and even more preferably 10 to 60 parts by mass.

[0530] <Other Ingredients>

[0531] In addition to components A and B described above, the compositions of the present invention may also contain other components. Examples of other components include (meth)acrylate monomers, polymers having free radical polymerizable groups on their side chains, and polymerization initiators. Furthermore, they may also contain polymers or monomers other than those described above, dispersants, plasticizers, heat stabilizers, release agents, solvents, etc. As heat stabilizers, for example, hindered phenolic heat stabilizers or phosphorus-based heat stabilizers described in paragraphs

[0261] and

[0262] of Japanese Patent Application Publication No. 2021-1328 can be used. Furthermore, since no further polymerization (curing) reaction is required in the resin compositions of the present invention, it is preferable that they do not contain polymers or monomers having polymerizable groups.

[0532] ((meth)acrylate monomer)

[0533] When the composition of the present invention is a curable composition, the curable composition of the present invention may contain a (meth)acrylate monomer. The (meth)acrylate monomer may be a polyfunctional (meth)acrylate monomer having two or more (meth)acryloyl groups in the molecule, or a monofunctional (meth)acrylate monomer having one (meth)acryloyl group in the molecule.

[0534] Specific examples of (meth)acrylate monomers include monomers 1 to 5 and M-1 to M-10 as described below. In monomer 5, n refers to the number of repetitions. Furthermore, examples include (meth)acrylate monomers described in paragraphs 0037 to 0046 of Japanese Patent Application Publication No. 2012-107191.

[0535] The molecular weight of the (meth)acrylate monomer is preferably 100 to 500.

[0536] [Chemical Formula 44]

[0537]

[0538] [Chemical Formula 45]

[0539]

[0540] There are no particular restrictions on the methods for obtaining (meth)acrylate monomers; they can be obtained commercially or synthesized using conventional methods.

[0541] When obtained through commercial means, the following are preferred options: Viscort#192PEA (monomer 1) (manufactured by OSAKA ORGANIC CHEMICAL IND.LTD.), Viscort#160BZA (monomer 2) (manufactured by OSAKA ORGANIC CHEMICAL IND.LTD.), LIGHT ESTER Bz (monomer 2) (manufactured by Kyoishachemical Co., Ltd.), A-DCP (monomer 3) (manufactured by Shin-Nakamura Chemical Co., Ltd.), FA-513AS (monomer 4) (manufactured by Hitachi Chemical Co., Ltd.), A-HD-N (M-1) (manufactured by Shin-Nakamura Chemical Co., Ltd.), HD-N (M-2) (manufactured by Shin-Nakamura Chemical Co., Ltd.), FA-BZA (M-3) (manufactured by Hitachi Chemical Co., Ltd.), and LIGHT ESTER. IB-X (M-4 above) (manufactured by Kyoisha Chemical Co., Ltd.), FA-513M (M-5 above) (manufactured by Hitachi Chemical Co., Ltd.), LIGHT ESTER L (M-6 above) (manufactured by Kyoisha Chemical Co., Ltd.), 2EHA (M-7 above) (manufactured by TOAGOSEI CO., LTD.), HEA (M-8 above) (manufactured by OSAKA ORGANIC CHEMICAL IND. LTD.), LIGHT ESTER HOP-A(N) (M-9 above) (manufactured by Kyoisha Chemical Co., Ltd.), 4-HBA (M-10 above) (manufactured by OSAKA ORGANIC CHEMICAL IND. LTD.).

[0542] When the curable composition of the present invention contains (meth)acrylate monomers, the content of (meth)acrylate monomers in the curable composition is preferably 1 to 60% by mass, more preferably 2 to 45% by mass, even more preferably 3 to 35% by mass, and particularly preferably 5 to 30% by mass. Furthermore, it is also preferably 7 to 25% by mass. By adjusting the amount of (meth)acrylate monomers in the curable composition of the present invention, the function of mitigating stress during thermal changes in the cured product can be adjusted.

[0543] (Polymers with free radical polymerizable groups on their side chains)

[0544] In addition to the compounds described above, the curable compositions of the present invention may also contain polymers with free radical polymerizable groups on their side chains. Since polymers with free radical polymerizable groups on their side chains increase the viscosity of the curable composition, they can also be referred to as thickeners or thickening polymers. Polymers with free radical polymerizable groups on their side chains can be added to adjust the viscosity of the curable composition.

[0545] Polymers with free radical polymerizable groups on their side chains can be homopolymers or copolymers. Preferably, polymers with free radical polymerizable groups on their side chains are copolymers. When the polymer with free radical polymerizable groups on its side chains is a copolymer, it is sufficient that at least one copolymer component has a free radical polymerizable group. Furthermore, when the polymer with free radical polymerizable groups on its side chains is a copolymer, it is more preferably a copolymer containing monomer units with free radical polymerizable groups on their side chains and monomer units with aromatic hydrocarbon groups on their side chains.

[0546] The copolymers mentioned above can also be copolymers of any form, such as random and block copolymers.

[0547] Examples of free radical polymerizable groups include (meth)acrylate, vinyl, styrene, and allyl groups. In polymers with free radical polymerizable groups on their side chains, it is preferable to include 5 to 100% by mass of structural units with free radical polymerizable groups, more preferably 10 to 90% by mass, and even more preferably 20 to 80% by mass.

[0548] The following are specific examples of polymers having free radical polymerizable groups on their side chains, which are preferred for use in this invention. However, polymers having free radical polymerizable groups on their side chains are not limited to the following structures. The specific examples shown below are all copolymers, each containing two or three adjacent structural units. For example, a specific example described at the top left end is a copolymer of allyl methacrylate and benzyl methacrylate.

[0549] In the following structural formula, Ra and Rb independently represent hydrogen atoms or methyl groups, respectively. Furthermore, the multiple Ra atoms in a polymer can be the same or different. And n represents 0 to 10, preferably 0 to 2, more preferably 0 or 1. The ratio of each structural unit in the copolymer is not particularly limited, and the above description is preferably applicable as the content of structural units with free radical polymerizable groups in the copolymer.

[0550] [Chemical Formula 46]

[0551]

[0552] [Chemical Formula 47]

[0553]

[0554] The molecular weight (weight-average molecular weight) of the polymer having free radical polymerizable groups on its side chains is preferably 1,000 to 10,000,000, more preferably 5,000 to 300,000, and even more preferably 10,000 to 200,000. The dispersion (Mw / Mn) of the polymer having free radical polymerizable groups on its side chains is preferably 1.1 to 10.0, more preferably 1.3 to 8.0, and even more preferably 1.5 to 6.0. The dispersion is calculated by dividing the weight-average molecular weight (Mw) by the number-average molecular weight (Mn).

[0555] As described in polymer B of the lens adhesive described later, the weight-average molecular weight and dispersion of the polymer having free radical polymerizable groups on the side chain are values ​​determined by conversion using GPC as a standard polystyrene.

[0556] Furthermore, the glass transition temperature of the polymer having free radical polymerizable groups on the side chain is preferably 50 to 400°C, more preferably 70 to 350°C, and even more preferably 100 to 300°C.

[0557] The content of polymers having free radical polymerizable groups on their side chains in the curable composition of the present invention is preferably 40% by mass or less, more preferably 30% by mass or less, further preferably 25% by mass or less, and particularly preferably 15% by mass or less. Alternatively, the content of polymers having free radical polymerizable groups on their side chains may be 0% by mass, and it is also preferable not to add polymers having free radical polymerizable groups on their side chains.

[0558] (Polymerization initiator)

[0559] The curable composition of the present invention preferably contains at least one of a thermal free radical polymerization initiator and a photofree radical polymerization initiator as a polymerization initiator.

[0560] (Thermal free radical polymerization initiator)

[0561] The curable composition of the present invention preferably contains a thermal free radical polymerization initiator (hereinafter also referred to as a "thermal polymerization initiator"). Through the action of this thermal polymerization initiator, the curable composition of the present invention is thermally polymerized, thereby exhibiting a low Abbe number and a high partial dispersion ratio, resulting in a cured product exhibiting excellent lightfastness.

[0562] As a thermal free radical polymerization initiator, compounds commonly used as thermal free radical polymerization initiators can be appropriately used depending on the conditions of the thermal polymerization (thermal curing) process described later. For example, organic peroxides can be mentioned, and specifically, the following compounds can be used.

[0563] Examples include 1,1-di(tert-hexylperoxy)cyclohexane, 1,1-di(tert-butylperoxy)cyclohexane, 2,2-di(4,4-di-(tert-butylperoxy)cyclohexyl)propane, tert-hexylperoxyisopropyl monocarbonate, tert-butylperoxy-3,5,5-trimethylhexanoate, tert-butylperoxylaurate, dicumyl peroxide, di-tert-butyl peroxide, ethyl tert-butylperoxy-2-hexanoate, di-tert-hexyl peroxide, ethyl tert-hexylperoxy-2-hexanoate, cumene hydroperoxide, tert-butyl hydroperoxide, tert-butylperoxy-2-ethylhexyl, and 2,3-dimethyl-2,3-diphenylbutane. Additionally, "tert-butyl" refers to "tert-butyl".

[0564] When a thermal free radical polymerization initiator is included, the content of the thermal free radical polymerization initiator in the curable composition of the present invention is preferably 0.01 to 5.0% by mass, more preferably 0.02 to 3.0% by mass, even more preferably 0.03 to 2.0% by mass, and particularly preferably 0.05 to 1.0% by mass.

[0565] (Photoradical polymerization initiator)

[0566] The curable composition of the present invention preferably contains a photoradical polymerization initiator (hereinafter also referred to as a "photopolymerization initiator"). As a photoradical polymerization initiator, a compound commonly used as a photoradical polymerization initiator can be appropriately used depending on the conditions of the photopolymerization (photocuring) process described later. Specifically, the following compounds can be used.

[0567] Examples include bis(2,6-dimethoxybenzoyl)-2,4,4-trimethylpentylphosphine oxide, bis(2,6-dimethylbenzoyl)-2,4,4-trimethylpentylphosphine oxide, bis(2,4,6-trimethylbenzoyl)-2,4,4-trimethylpentylphosphine oxide, bis(2,6-dichlorobenzoyl chloride)-2,4,4-trimethylpentylphosphine oxide, 1-phenyl-2-hydroxy-2-methylpropane-1-one, 1-hydroxycyclohexylphenyl ketone, 1-(4-isopropylphenyl)-2-hydroxy-2-methylpropane-1-one, 1,2-diphenylethanedione, methyl phenylglyoxylate, 1- [4-(2-hydroxyethoxy)-phenyl]-2-hydroxy-2-methyl-1-propane-1-one, 2-hydroxy-1-{4-[4-(2-hydroxy-2-methyl-propanoyl)-benzyl]phenyl}-2-methyl-propane-1-one, 2,2-dimethoxy-1,2-diphenylethane-1-one, 2-methyl-1-(4-methylthiophenyl)-2-morpholinylpropane-1-one, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butanone-1, 2,4,6-trimethylbenzoyl-diphenylphosphine oxide, bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide, etc.

[0568] Furthermore, among the photoradical polymerization initiators mentioned above, from the viewpoint of obtaining a cured product with excellent light resistance, an acylphosphine oxide photopolymerization initiator is preferred.

[0569] In this invention, the photoradical polymerization initiator preferably used is 1-hydroxycyclohexylphenyl ketone (available from BASF as Irgacure 184), bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide (available from BASF as Irgacure 819), 2,4,6-trimethylbenzoyl-diphenylphosphine oxide (available from BASF as Irgacure TPO), 2,2-dimethoxy-1,2-diphenylethane-1-one (available from BASF as Irgacure 651), 1-[4-(2-hydroxyethoxy)-phenyl]-2-hydroxy-2-methyl-1-propane-1-one or 2-methyl-1-(4-methylthiophenyl)-2-morpholinylpropane-1-one.

[0570] When a photoradical polymerization initiator is included, the content of the photoradical polymerization initiator in the above-mentioned curable composition is preferably 0.01 to 5.0% by mass, more preferably 0.05 to 1.0% by mass, and even more preferably 0.05 to 0.5% by mass.

[0571] Furthermore, the curable composition preferably contains both a photoradical polymerization initiator and a thermal radical polymerization initiator. In this case, the total content of the photoradical polymerization initiator and the thermal radical polymerization initiator relative to the total mass of the curable composition is preferably 0.01 to 5.0% by mass, more preferably 0.05 to 1.0% by mass, and even more preferably 0.05 to 0.5% by mass.

[0572] From the viewpoint of improving the operability of the cured material during molding and forming a high-quality cured material, the viscosity of the curable composition of the present invention is preferably 1,000 to 30,000 mPa·s, more preferably 3,000 to 20,000 mPa·s, and even more preferably 5,000 to 15,000 mPa·s.

[0573] <Cure or molded product>

[0574] The cured product of the present invention is a cured product of the curable composition of the present invention containing a polymeric compound comprising a nitrogen-containing fused aromatic ring as component A and component B.

[0575] The cured product of the present invention is obtained by polymerization of a monomer containing a polymerizable compound comprising a nitrogen-fused aromatic ring as component A, followed by curing. The cured product of the present invention may contain unreacted monomers (e.g., component A).

[0576] The molded article of the present invention is a molded article containing a polymer comprising a nitrogen-containing fused aromatic ring as component A and a resin composition of the present invention as component B.

[0577] The molded article of the present invention is obtained by molding a resin composition containing a polymer comprising a nitrogen-fused aromatic ring as component A.

[0578] In this invention, the cured product obtained from the curable composition of the present invention and the molded body obtained from the resin composition of the present invention are also referred to as "the cured product and the molded body of the present invention".

[0579] As mentioned above, the cured products and molded articles of the present invention have low Abbe number (νD), high partial dispersion ratio, and also exhibit excellent lightfastness.

[0580] The Abbe number (νD) and partial dispersion ratio (θg, F value) of the cured and molded products were measured using an Abbe refractometer (ATAGO CO., LTD, manufactured, trade name: DR-M4). Specifically, the measurements were performed according to the description in the <Optical Property Measurement> section of the examples described later.

[0581] The Abbe number (νD) and partial dispersion ratio (θg, F-value) of the cured product and molded body are calculated using the following formula. Furthermore, when molding the cured product, it is sufficient to use the photocured sample preparation method described in Example 1 below. A heating process can be used instead of the ultraviolet irradiation process, or both heating and ultraviolet irradiation processes can be used. Additionally, JIS B 7090:1999 Optics and optical instruments—Reference wavelengths (ISO 7944:1998 Optics and optical instruments—Reference wavelengths) can be appropriately referenced.

[0582] νD=(nD-1) / (nF-nC)

[0583] θg, F=(ng-nF) / (nF-nC)

[0584] Here, nD represents the refractive index at a wavelength of 589 nm, nF represents the refractive index at a wavelength of 486 nm, nC represents the refractive index at a wavelength of 656 nm, and ng represents the refractive index at a wavelength of 436 nm.

[0585] In addition, when the d line (587.56 nm) is used as the reference instead of the D line, it is labeled as the Abbe number (νd). However, when using compounds with nitrogen-containing fused aromatic rings, the Abbe number (νD) and the Abbe number (νd) usually show the same value.

[0586] The Abbe number of the cured product and molded article of the present invention is not particularly limited, but is preferably 35 or less, more preferably 30 or less, further preferably 29 or less, and particularly preferably 28 or less. Furthermore, the Abbe number of the cured product and molded article of the present invention is not particularly limited, but is preferably 1 or more, more preferably 3 or more, further preferably 5 or more, and particularly preferably 7 or more.

[0587] The partial dispersion ratio (θg, F value) of the cured product and molded article of the present invention is not particularly limited, but is preferably 0.65 or more, more preferably 0.70 or more, further preferably 0.72 or more, and particularly preferably 0.75 or more. Furthermore, the partial dispersion ratio (θg, F value) of the cured product and molded article of the present invention is not particularly limited, but is preferably 2 or less, more preferably 1.8 or less, and further preferably 1.7 or less.

[0588] When the cured and molded products of the present invention are used as lenses, they are required to be transparent and not absorb light in the visible light region.

[0589] The cured and molded products of the present invention exhibit substantially no absorption in the long wavelength region of the visible light spectrum, and their visible transmittance decreases as the wavelength decreases. Therefore, the transparency of the cured and molded products of the present invention can be evaluated by measuring the transmittance at a wavelength of 430 nm.

[0590] The transmittance of the cured product and molded body of the present invention at a wavelength of 430 nm was measured using a UV-Vis spectrophotometer (e.g., UV-2600 (trade name, manufactured by Shimadzu Corporation)). Specifically, the transmittance at a wavelength of 430 nm was measured for a cured product with a thickness of approximately 500 μm, for example, made using a transparent glass mold with a diameter of 20 mm and a thickness of 500 μm, in the same manner as the photocurable sample described in Example 1 below. Furthermore, the transmittance at a wavelength of 430 nm was measured for a molded body with a thickness of approximately 500 μm, for example, made using a spacer with a thickness of 500 mm, in the same manner as the evaluation sample described in Example 2 below.

[0591] Furthermore, the light irradiation test used to evaluate the light resistance of the cured product and the molded body was performed according to the xenon light irradiation test described in the examples described later.

[0592] Hereinafter, preferred values ​​are recorded for the transmittance of the cured material and molded body at a wavelength of 430 nm as measured by the above method.

[0593] The transmittance of the cured product and the molded body of the present invention after fabrication, i.e., the transmittance before light irradiation test, is not particularly limited, but is preferably 80% or more, more preferably 82% or more, further preferably 83% or more, and particularly preferably 85% or more.

[0594] Furthermore, the transmittance of the cured product and the molded article of the present invention after light irradiation test is not particularly limited, but in the evaluation 2 (transmittance after xenon light irradiation test for 48 hours) described later, it is preferably 72% or more, more preferably 75% or more, further preferably 79% or more, and particularly preferably 81% or more.

[0595] The decrease in transmittance of the cured product and molded article of the present invention before and after the light irradiation test is not particularly limited, but in the evaluation 3 (the decrease in transmittance before and after the xenon light irradiation test 48 hours later) described later, it is preferably 15% or less, more preferably 12% or less, further preferably 8% or less, and particularly preferably 5% or less.

[0596] The decrease in transmittance before and after the light irradiation test is calculated by subtracting the transmittance value after the light irradiation test from the transmittance value before the light irradiation test.

[0597] Furthermore, preferred values ​​are described for the transmittance at a wavelength of 430 nm for the composite lens containing a lens substrate manufactured using the cured or molded body of the present invention, as described later.

[0598] The transmittance of the composite lens of the present invention, i.e. the transmittance before the light irradiation test, is not particularly limited, but is preferably 80% or more, more preferably 82% or more, even more preferably 83% or more, and particularly preferably 85% or more.

[0599] Furthermore, the transmittance of the composite lens of the present invention after the light irradiation test is not particularly limited, but in the evaluation 5 (transmittance after irradiation with xenon light for 240 hours) described later, it is preferably 74% or more, more preferably 75% or more, further preferably 78% or more, and particularly preferably 79% or more.

[0600] The decrease in transmittance of the composite lens of the present invention before and after the light irradiation test is not particularly limited, but in the evaluation 6 (decrease before and after the xenon light irradiation 240-hour test) described later, it is preferably 15% or less, more preferably 12% or less, further preferably 8% or less, and particularly preferably 5% or less.

[0601] The decrease in transmittance before and after the light irradiation test is calculated by subtracting the transmittance value after the light irradiation test from the transmittance value before the light irradiation test.

[0602] The transmittance of the composite lens of the present invention at a wavelength of 430 nm is a value measured using a UV-Vis spectrophotometer (e.g., UV-2600 (trade name, manufactured by Shimadzu Corporation)). Specifically, the transmittance at a wavelength of 430 nm is measured for a composite lens manufactured in the same manner as the composite lens described in Reference Example 1 below.

[0603] [Method for manufacturing cured products]

[0604] The cured product of the present invention can be manufactured by a method including at least one of a step of photocuring the curable composition of the present invention and a step of heat curing. Preferably, the method for manufacturing the cured product includes a step of forming a semi-cured product by irradiating or heating the curable composition with light and a step of forming a cured product by irradiating or heating the obtained semi-cured product with light or a semi-cured product.

[0605] Unless otherwise specified, the terms "process for forming a semi-cured product", "process for forming a cured product" and "semi-cured product" can be replaced with "curable composition of the present invention" and the descriptions of "process for forming a semi-cured product", "process for forming a cured product" and "semi-cured product" in International Publication No. 2019 / 044863

[0106] to

[0117] ,

[0118] to

[0124] and

[0125] can be applied as is.

[0606] Furthermore, in this invention, the pressure during the pressure deformation in the "process of forming a solidified product" is preferably 0.098 MPa to 9.8 MPa, more preferably 0.154 MPa to 4.9 MPa, and even more preferably 0.154 MPa to 2.94 MPa.

[0607] [Manufacturing method of molded body]

[0608] The molded article of the present invention can be manufactured by molding the resin composition of the present invention. Examples of molding methods for the molded article include heat-pressurization molding, compression molding, injection molding, extrusion molding, blow molding, embossing, etc.

[0609] The resin composition of the present invention can also be granulated before heat-press molding. By granulating the resin composition of the present invention, the workability of the resin during heat-press molding can be improved. When granulating the resin composition of the present invention, for example, a vented single-screw extruder can be used.

[0610] In the case of compression molding, the resin composition of the present invention (preferably particles of the resin composition of the present invention) can be sandwiched between the top and bottom of a resin film such as a polyimide film by using spacers of desired thickness, heated and compressed, and then removed from the resin film along with the spacers and cooled (including natural cooling) to room temperature to form the product.

[0611] As for the conditions for performing heating and compression, the heating temperature is preferably 180 to 450°C, more preferably 180 to 390°C, the pressure is preferably 0.098 MPa to 9.8 MPa, more preferably 0.294 MPa to 9.8 MPa, and even more preferably 1.0 MPa to 9.8 MPa, and the pressurization time is preferably 30 to 1000 seconds, more preferably 30 to 500 seconds, and even more preferably 60 to 500 seconds.

[0612] In the case of injection molding, an injection molding machine (including an injection compression molding machine) is used. In the injection molding machine, the molten resin composition of the present invention is stored at the front end of the barrel, and then the molten resin composition of the present invention is injected into the mold for molding. As the injection molding machine, a conventionally used injection molding machine can be used. The barrel is preferably made of a material that exhibits low adhesion to the resin composition of the present invention and displays corrosion resistance and abrasion resistance. For example, the Micro-1 manufactured by MEIHO CO., LTD. can be cited as an example of an injection molding machine.

[0613] The barrel temperature during injection molding is preferably 200–450°C, more preferably 250–390°C. Furthermore, the mold temperature is preferably 50–300°C, more preferably 100–250°C.

[0614] [Applications of cured products and molded articles]

[0615] The cured products and molded articles of the present invention exhibit low Abbe number (νD) or high partial dispersion ratio and excellent lightfastness, and are therefore suitable for a variety of applications, particularly optical components.

[0616] <Optical Components>

[0617] The type of optical component is not particularly limited; in particular, any optical component that transmits light (so-called passive optical component) can be preferably used. Examples of optical functional devices equipped with such optical components include various display devices (liquid crystal displays or plasma displays, etc.), various projection devices (OHP (overhead projector), liquid crystal projectors, etc.), fiber optic communication devices (optical waveguides, optical amplifiers, etc.), and photographic devices such as cameras or video cameras.

[0618] Examples of passive optical components include lenses, prisms, prism sheets, panels (plate-shaped molded bodies), thin films, optical waveguides (thin film or fiber optic, etc.), optical discs, and sealants for LEDs (Light Emitting Diodes). Passive optical components can incorporate any coating layer or any additional functional layer as needed. For example, passive optical components may include protective layers to prevent mechanical damage to the coated surface due to friction or wear; light-absorbing layers to absorb unwanted wavelengths of light that contribute to the degradation of inorganic particles or substrates; transmission-shielding layers to suppress or prevent the transmission of reactive low-molecular-weight substances such as moisture or oxygen; anti-glare layers; anti-reflection layers; and low-refractive-index layers. Specific examples of coating layers include transparent conductive films or gas-barrier films formed from inorganic oxide or inorganic nitride coatings, and gas-barrier films or hard coatings formed from organic coatings. As a coating method for forming a coating, known coating methods such as vacuum evaporation, CVD (Chemical Vapor Deposition), sputtering, dip coating, and spin coating can be used.

[0619] [Lens substrate]

[0620] Optical components can be lens substrates. That is, the cured or molded articles of the present invention can also be used as lens substrates. In this specification, "lens substrate" refers to a single component capable of performing the function of a lens. Lens substrates manufactured using the cured or molded articles of the present invention exhibit low Abbe numbers, high partial dispersion ratios, and excellent lightfastness. Furthermore, it is preferable that by appropriately adjusting the types of monomers constituting the curable composition of the present invention or the monomer components constituting the polymer contained as component A in the resin composition of the present invention, the refractive index of the lens substrate can be arbitrarily adjusted, and lens substrates possessing high refractive index, high partial dispersion ratios, and lightweight properties can also be manufactured.

[0621] Depending on the environment or application of the lens, a film or component can be provided on or around the lens substrate. For example, a protective film, an anti-reflective film, a hard coating film, etc., can be formed on the surface of the lens substrate. Furthermore, it is possible to manufacture a composite lens by laminating a lens substrate manufactured using the cured or molded body of the present invention with one or more other lens substrates selected from glass lens substrates and plastic lens substrates (hereinafter referred to as "other lens substrates").

[0622] For example, a composite lens can be manufactured by photocuring the curable composition of the present invention onto other lens substrates to form a semi-cured product, and then heating the obtained semi-cured product to form a cured product. The semi-curing process and the process of forming the cured product are preferably applied as described above. The curable composition of the present invention has excellent photocuring sensitivity, thus enabling the production of composite lenses of excellent quality. In the present invention, excellent photocuring sensitivity means that a gel-like or rubber-like semi-cured product can be obtained from the liquid curable composition through a photocuring reaction.

[0623] Furthermore, when using the resin composition of the present invention, for example using an injection molding machine, a granulated melt of the resin composition of the present invention is injected into a molding die to cover the transparent glass lens on the entire surface of the side of the resin that is not in contact with the molding die, and the lens is unfolded. After cooling, the mold is separated, thereby obtaining a composite lens.

[0624] The lens substrate can be embedded and fixed in a substrate holding frame or the like. However, these films or frames are components attached to the lens substrate and are distinct from the lens substrate itself as referred to in this specification.

[0625] When using a lens substrate as a lens, the lens substrate itself can be used as a lens alone, or it can be used as a lens by attaching the aforementioned film or frame, other lens substrates, etc. The type or shape of the lens using the lens substrate is not particularly limited, and the maximum thickness is preferably 0.1 to 10 mm. The maximum thickness is more preferably 0.1 to 5 mm, and even more preferably 0.15 to 3 mm. Furthermore, the maximum diameter of the lens substrate is preferably a circular shape of 1 to 1000 mm. The maximum diameter is more preferably 2 to 200 mm, and even more preferably 2.5 to 100 mm.

[0626] The lens substrate is preferably used for camera lenses such as those for mobile phones or digital cameras, photographic lenses for televisions and camcorders, as well as automotive lenses and endoscope lenses.

[0627] <Joint Lens>

[0628] By using other lenses and lens adhesives to bond the lens substrate or lens manufactured using the composition of the present invention, it is possible to manufacture a bonded lens.

[0629] [Other Lenses]

[0630] Other types of lenses are not particularly limited, and examples include disc-shaped convex lenses, concave lenses, meniscus lenses, aspherical lenses, cylindrical lenses with cylindrical lens surfaces, spherical lenses, and rod lenses. Furthermore, the materials of other lenses are not particularly limited; any glass lens, resin lens, or composite lens is acceptable.

[0631] (Glass lens)

[0632] As a glass lens, known lenses can be used without restriction. For example, the BK7 (trade name) manufactured by OHARA INC. is a commercially available glass lens.

[0633] The same glass lens can also be used when the compound lens includes a glass lens.

[0634] (Resin lenses, composite lenses)

[0635] Resin lenses are lenses made of cured resin.

[0636] In this specification, a composite lens refers to a lens comprising a glass layer and a resin layer. The resin layer is a layer composed of cured resin. Each layer in a composite lens can be a lens (a single lens), in which case it is preferable that the optical axes (lines connecting the centers of curvature of two spherical surfaces) of each single lens are aligned. A composite lens may have a resin layer on its surface or internally.

[0637] [Adhesive for Lenses]

[0638] As an adhesive for lenses, it allows for the use of common adhesives without restriction.

[0639] As a lens adhesive, a lens adhesive containing a compound represented by general formula (1) is particularly preferred. The lens adhesive containing the compound represented by general formula (1) absorbs ultraviolet light and exhibits excellent adhesion to ultraviolet radiation; therefore, by using this lens adhesive, a cured product with high light stability for bonding lenses can be obtained. Furthermore, the adhesive layer formed from the lens adhesive containing the compound represented by general formula (1) has high resistance to thermal shock.

[0640] (Compounds represented by general formula (1))

[0641] [Chemical Formula 48]

[0642] Pol 1 -Sp e -L 1 -Ar 21 -L 2 -Sp f -Pol 2 General formula (1)

[0643] In the above formula, Ar 21 It is an aromatic cyclic group represented by any one of the following general formulas (21-1) to (21-4).

[0644] [Chemical Formula 49]

[0645]

[0646] In the above formula, Q 1 Indicates -S-, -O-, or NR 11 -, R 11 It represents an alkyl group having 1 to 6 hydrogen atoms or carbon atoms.

[0647] Y 1 It represents an alkyl group with 1 to 6 carbon atoms, an aromatic hydrocarbon group with 6 to 12 carbon atoms, or an aromatic heterocyclic group with 3 to 12 carbon atoms.

[0648] Z 1 Z 2 and Z 3 Represents hydrogen atoms, aliphatic hydrocarbon groups with 1 to 20 carbon atoms, alkoxy groups with 1 to 20 carbon atoms, alicyclic hydrocarbon groups with 3 to 20 carbon atoms, aromatic hydrocarbon groups with 6 to 20 monovalent carbon atoms, halogen atoms, cyano groups, nitro groups, and -NR groups. 12 R 13 or -SR 12 Z 1 With Z 2 They can bond with each other to form aromatic hydrocarbon rings or aromatic heterocycles, R 12 and R 13 It represents an alkyl group having 1 to 6 hydrogen atoms or carbon atoms.

[0649] A 1 and A 2 Represent the selection of -O- and -NR independently, respectively. 21 -(R 21 It represents a hydrogen atom or a substituent. It is a group in the group consisting of -S- and -C(=O)-, where X represents O (oxygen atom), S (sulfur atom), C (carbon atom) bonded with a hydrogen atom or a substituent, or N (nitrogen atom) bonded with a hydrogen atom or a substituent.

[0650] Ax represents an organic group having 1 to 30 carbon atoms of at least one aromatic ring selected from the group consisting of aromatic hydrocarbon rings and aromatic heterocycles. Ay represents an organic group having 1 to 30 carbon atoms of a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or an organic group having 1 to 30 carbon atoms of at least one aromatic ring selected from the group consisting of aromatic hydrocarbon rings and aromatic heterocycles. The aromatic rings of Ax and Ay may have substituents, and Ax and Ay may bond to each other to form a ring.

[0651] Q 2 It represents an alkyl group having 1 to 6 hydrogen atoms or carbon atoms.

[0652] Additionally, * indicates the relationship with L. 1 or L 2 The bonding positions.

[0653] Regarding the definitions and preferred ranges of each substituent in general formulas (21-1) to (21-4), it is possible to compare the information concerning compound (A) and Y described in Japanese Patent Application Publication No. 2012-21068 with that of Y. 1 Q 1 and Q 2 The relevant records shall be applied to Y as is. 1 Z 1 Z 2 The descriptions of compounds represented by general formula (I) relating to A1, A2, and X in Japanese Patent Application Publication No. 2008-107767 can be applied exactly as described in A. 1 A 2 And X, capable of relating the compounds represented by general formula (I) as described in WO2013 / 018526 to A x A y and Q 1 The relevant records are applied as is to Ax, Ay, and Q in general formula (21-3). 2 It is able to connect the compounds represented by general formula (II) described in WO2013 / 018526 with A a A b and Q 11 The relevant records are applied as is to Ax, Ay, and Q in general formula (21-4). 2 Regarding Z 2 It is applicable as is to the contents of Japanese Patent Application Publication No. 2012-21068 concerning compound (A) and Q. 1 Relevant records.

[0654] In general formula (21-2), X is preferably a carbon atom bonded with two substituents, and A 1 A 2 Preferably, all are -S-. In general formula (21-3), the ring formed when Ax and Ay are bonded together is preferably an alicyclic hydrocarbon ring, an aromatic hydrocarbon ring, or an aromatic heterocycle, more preferably an aromatic heterocycle. In general formula (21-4), the ring formed when Ax and Ay are bonded together is preferably an unsaturated hydrocarbon ring.

[0655] Ar in general formula (1) 21 Preferably, it is an aromatic cyclic group represented by general formula (21-2).

[0656] As an aromatic ring group represented by general formula (21-2), it is preferred to be an aromatic ring group represented by the following general formula (21-2-1).

[0657] [Chemical Formula 50]

[0658]

[0659] In the formula, Rz represents a substituent, and Z 1 and Z 2 The meanings are respectively the same as Z in the above general formula (21-2). 1 and Z 2 The meanings are the same.

[0660] As an example of the substituents represented by Rz, Sp, which will be discussed later, can be cited. e and Sp f The straight-chain alkylene group may have substituents, preferably alkyl, alkoxy, alkoxycarbonyl, halogen, and cyano groups. The two Rz groups may be the same or different.

[0661] Furthermore, the two Rz atoms can also bond together to form a ring. The resulting ring is preferably a 5-membered or 6-membered ring, more preferably a 5-membered or 6-membered ring containing a nitrogen atom or an oxygen atom as a constituent atom. The ring formed by the bonding of the two Rz atoms is further preferably a ring represented by any of the following structures.

[0662] [Chemical Formula 51]

[0663]

[0664] In the above formulas, * denotes the positions of the carbon atoms bonded by the two Rz atoms in general formula (21-2-1). Furthermore, the ring represented by any of the above formulas may have substituents in the nitrogen atom or carbon atom. As substituents in this case, alkyl groups having 1 to 6 carbon atoms are preferred, and linear alkyl groups having 1 to 4 carbon atoms are more preferred.

[0665] As an aromatic cyclic group represented by the general formula (21-2-1), it is preferred to be an aromatic cyclic group in which at least one Rz is a cyano group or an aromatic cyclic group in which two Rz are bonded together to form a ring, and more preferably an aromatic cyclic group in which both Rz are cyano groups.

[0666] This is because in lens adhesives containing such compounds represented by general formula (1) with aromatic ring groups, it is possible to more significantly achieve the effect of maintaining high transmittance in the visible light region and improving absorption in the ultraviolet region.

[0667] In general formula (1), L 1 and L 2 The meaning of L is the same as that of L in the above general formula (A0), and the preferred range is also the same.

[0668] In general formula (1), Sp e and Sp f The meaning of Sp is the same as that of Sp in the above general formula (A0), and the preferred range is also the same.

[0669] In general formula (1), Pol 1 and Pol2 The meaning of is the same as that of Pol in the above general formula (A0), and the preferred range is also the same.

[0670] As Pol 1 -Sp e -L 1 -or Pol 2 -Sp f -L 2 Specific examples of the structure of - can be given as the same examples given for Pol-Sp-L- in the above general formula (A0).

[0671] Hereinafter, specific examples of compounds represented by general formula (1) preferably used in the above-described lens adhesives are given, but the use of these compounds is not limited to them. Furthermore, in the following structural formulas, Me represents methyl, Et represents ethyl, nPr represents n-propyl, iPr represents isopropyl, nBu represents n-butyl, and tBu represents tert-butyl. Moreover, the compounds used in the examples described later are also preferred.

[0672] [Chemical Formula 52]

[0673]

[0674] [Chemical Formula 53]

[0675]

[0676] [Chemical Formula 54]

[0677]

[0678] [Chemical Formula 55]

[0679]

[0680] [Chemical Formula 56]

[0681]

[0682] [Chemical Formula 57]

[0683]

[0684] [Chemical Formula 58]

[0685]

[0686] [Chemical Formula 59]

[0687]

[0688] [Chemical Formula 60]

[0689]

[0690] [Chemical Formula 61]

[0691]

[0692] The content of the compound represented by general formula (1) in the lens adhesive is preferably 10 to 90% by mass, more preferably 15 to 85% by mass, and even more preferably 20 to 80% by mass, relative to the total mass of the lens adhesive. By setting it to 90% by mass or less, the viscosity can be kept within the preferred range.

[0693] The adhesive for lenses may contain two or more compounds represented by general formula (1). When it contains two or more compounds represented by general formula (1), it is preferable that the total content is within the range described above.

[0694] (polymer)

[0695] Lens adhesives may contain polymers or oligomers (hereinafter also referred to as "polymers") for the purpose of adjusting viscosity or Young's modulus of the cured product. As a polymer, there are no particular limitations, but polymers having olefin unsaturated groups are preferred. The olefin unsaturated groups may be contained within the polymer backbone, at the backbone end, or in the side chain. As an olefin unsaturated group, there are no particular limitations, but olefin unsaturated bonds or (meth)acryloyl groups derived from butadiene or isoprene are preferred.

[0696] The polymer contained in the lens adhesive is preferably a polymer selected from the group consisting of conjugated diene polymers and polyurethane resins having olefinic unsaturated groups, and more preferably a polymer selected from the group consisting of polymers having a polybutadiene structure, polymers having a polyisoprene structure, and urethane (meth)acrylates.

[0697] As a polymer with a polybutadiene structure, commercially available products include, for example, the NIPOL BR series (manufactured by Zeon Corporation), UBEPOL BR series (manufactured by Ube Industries, Ltd.), NISSO-PB series (manufactured by Nippon Soda Co., Ltd.), Claprene LBR series, and Claprene L-SBR series (manufactured by KURARAY CO., LTD.).

[0698] As a polymer with a polyisoprene structure, commercially available products include, for example, the NIPOL IR series (manufactured by Zeon Corporation), the Claprene LIR series, and the Claprene UC series (manufactured by KURARAY CO., LTD).

[0699] As urethane (meth)acrylates, commercially available products include, for example, the following products from the Ziguang (registered trademark) series: UV-3200, UV-3000B, UV-3700B, UV-3210EA, UV-2000B, UV-3630 (and above, manufactured by The Nippon Synthetic Chemical Industry Co., Ltd.), EBECRYL230, EBECRYL9227EA (and above, manufactured by Daicel SciTech Co., Ltd.), and the HI-CORP AU (registered trademark) series: AU-3040, AU-3050, AU-3090, AU-3110, AU-3120 (and above, manufactured by TOKUSHIKI Co., Ltd.).

[0700] As a polymer that can be contained in the lens adhesive, a preferred example is a polymer comprising a structural unit (b1) having an aromatic ring and a structural unit (b2) having a hydrogen-bonding group, wherein the proportion of the aforementioned structural unit (b1) in all structural units constituting the polymer is 10% by mass or more, and the proportion of the aforementioned structural unit (b2) is 3% by mass or more (hereinafter, simply referred to as "Polymer B").

[0701] In this invention, among the structural units contained in the polymer B described above, those structural units having hydrogen-bonding groups are necessarily classified as structural unit (b2). That is, structural units that do not have hydrogen-bonding groups but have both aromatic rings and hydrogen-bonding groups are classified as structural unit (b2).

[0702] Polymer B is not particularly limited in type as long as it is a polymer having a structural unit containing an aromatic ring (b1) and a structural unit containing a hydrogen-bonded group (b2). It can be a vinyl polymer such as acrylic polymer, an addition polymer such as polyurethane, a fused polymer such as polyester and polycarbonate, or a ring-opening metathesis polymer using cyclic olefin monomers, etc. From the viewpoint of further improving adhesion and damp heat durability, vinyl polymers are preferred.

[0703] (b1) Structural units with aromatic rings

[0704] Polymer B contains a structural unit (b1) with an aromatic ring.

[0705] Examples of aromatic rings that can be found in the above-mentioned structural unit (b1) include aromatic hydrocarbon rings such as benzene ring, naphthalene ring, anthracene ring, or phenanthrene ring, or aromatic heterocycles such as furan ring, pyrrole ring, thiophene ring, pyridine ring, thiazole ring, benzothiazole ring, or phenanthrene-roline ring.

[0706] The aromatic ring of the above structural unit (b1) is preferably a benzene ring, a naphthalene ring, or a pyridine ring, and from the viewpoint of further improving the tightness, a benzene ring is more preferred.

[0707] The polymer B described above preferably has a structural unit (b1) represented by the following general formula (p1).

[0708] [Chemical Formula 62]

[0709]

[0710] In the above formula, R P1 L represents a hydrogen atom or a methyl group. P1 Ar represents a single bond or a divalent linker. P This indicates an aromatic hydrocarbon group that may have substituents or an aromatic heterocyclic group that may have substituents.

[0711] In this case, the structural unit represented by the general formula (p1) does not have hydrogen-bonded groups. That is, L P1 It does not have hydrogen-bonding groups, and Ar P It also does not have hydrogen-bonding groups.

[0712] * indicates a bonding site used for binding into the polymer.

[0713] Additionally, under -L P1 -Ar P Among the groups represented, the longest bonded chain is selected from R. P1 The number of carbon atoms bonded at the end of the aromatic hydrocarbon ring or aromatic heterocycle is interpreted as Ar. P The remaining part is interpreted as L P1 .

[0714] That is, as Ar P The aromatic hydrocarbon ring in the aromatic hydrocarbon group that may have substituents and the aromatic heterocyclic ring in the aromatic heterocyclic group that may have substituents can be described as aromatic hydrocarbon rings and aromatic heterocyclic rings that are the aromatic rings of the above-mentioned structural unit (b1).

[0715] As Ar P The aromatic hydrocarbon cyclic group and aromatic heterocyclic group in the compound can have substituents, such as alkyl, alkoxy, alkoxysilyl, and acyloxy.

[0716] LP1 This indicates a single bond or a divalent linker.

[0717] As L P1 Examples of divalent linking groups that can be used include alkylene groups, divalent aromatic hydrocarbon groups (e.g., 1,4-phenylene, hereinafter referred to as "arylene"), divalent aromatic heterocyclic groups (hereinafter referred to as "heteroarylene"), and groups selected from -O-, >C (=O), and >NR. b The groups in the group and the linking groups consisting of two or more of these groups.

[0718] R b It is an alkyl, monovalent aliphatic or aromatic heterocyclic group or a monovalent aromatic hydrocarbon cyclic group.

[0719] As selected from -O-, >C (=O) and >NR above b Linking groups consisting of two or more groups, such as -OC(=O)-, -C(=O)O-, -OC(=O)O-, and -NR. b C(=O)-、-C(=O)NR b -、-OC(=O)NR b -or-NR b C(=O)O-, preferably -OC(=O-), -C(=O)O-, -NR b C(=O)-or-C(=O)NR b - Additionally, in the description of the linking group mentioned above, the left side is connected to R. P1 The bonded carbon atoms are bonded, with Ar on the right side. P Bonding. The same meaning applies below. For example, if we take the linking group -OC (=O)- as an example, the left side refers to the ether bond side, and the right side refers to the carbonyl bond side.

[0720] Furthermore, preferably, at least one group selected from alkylene, arylene, and heteroarylene, and a group selected from -O-, >C (=O), and >NR are also included. b The group consists of at least one of the groups in the -C(=O)O-alkylene group or a combination of two or more of these groups forming a linking group. For example, -C(=O)O-alkylene group can be cited. Furthermore, it is also preferred to cite groups further combined with -O-, arylene-O-, -O-arylene, heteroarylene-O-, or -O-heteroarylene groups on the alkylene group in the -C(=O)O-alkylene group.

[0721] As L P1Preferably, it is a single bond, -C(=O)O-alkylene, or a group further combined with -O-, arylene-O-, -O-arylene, heteroarylene-O- or -O-heteroarylene on the alkylene of -C(=O)O-alkylene, more preferably -C(=O)O-alkylene or a group further combined with -O-, arylene-O- or -O-arylene on the alkylene of -C(=O)O-alkylene, and even more preferably -C(=O)O-alkylene or -C(=O)O-alkylene-O-.

[0722] As a structural unit represented by the above general formula (p1), the following structural units can be cited as examples. However, it is not limited to these structural units.

[0723] In addition, in the following chemical structural formula, Me represents methyl and t-Bu represents tert-butyl.

[0724] [Chemical Formula 63]

[0725]

[0726] The proportion of aromatic ring-containing structural units (b1) in all structural units constituting polymer B is preferably 10 to 97% by mass, more preferably 20 to 96% by mass, and particularly preferably 30 to 95% by mass from the viewpoint of further improving transmittance.

[0727] When polymer B has other structural units besides structural units (b1) and (b2), the proportion of structural unit (b1) containing an aromatic ring among all structural units constituting polymer B is preferably 10 to 80% by mass, more preferably 20 to 80% by mass, and even more preferably 30 to 75% by mass.

[0728] Furthermore, regarding the proportions of aromatic ring-containing structural units (b1) and hydrogen-bonded structural units (b2) in all structural units constituting polymer B, it is possible to determine the proportions of aromatic ring-containing structural units (b1) in the remaining monomer components after determining the proportions of hydrogen-bonded structural units (b2) in the monomer components used to obtain the polymer, based on the mass ratio of these proportions. For example, in the case of a polyurethane synthesized by addition polymerization of a difunctional isocyanate compound (A1) having an aromatic ring and a diol compound (B1), the proportion of isocyanate compound (A1) in the monomer components becomes the proportion of the aforementioned structural units (b1), and the proportion of diol compound (B1) in the monomer components becomes the proportion of the aforementioned structural units (b2). Furthermore, in the case of polymers obtained during synthesis accompanied by elimination reactions, for example, in the case of polyamides obtained by the fusion polymerization of a difunctional acyl chloride compound (A2) having an aromatic ring and a compound (B2) having two primary amino groups, the structural unit that eliminates two chlorine atoms from the acyl chloride compound (A2) corresponds to the aforementioned structural unit (b1), and the structural unit that eliminates two hydrogen atoms from the compound (B2) (i.e., eliminating hydrogen atoms one by one from the two primary amino groups) corresponds to the aforementioned structural unit (b2). Therefore, based on the mass ratio of these compounds (A2) to (B2), the content ratio of the aforementioned structural units (b1) and (b2) can be determined.

[0729] (b2) Structural units with hydrogen-bonded groups

[0730] The polymer B mentioned above contains a structural unit (b2) with hydrogen-bonded groups.

[0731] The hydrogen-bonding groups in the above structural unit (b2) refer to groups with hydrogen atoms that can form hydrogen bonds, such as hydroxyl, carboxyl, sulfonyl, phosphate, phosphonic acid, amino, thioalkyl, amide, carbamate, urea, thiocarbamate, thiourea, or sulfonamide.

[0732] In the above, hydroxyl, carboxyl, sulfonyl (sulfonic acid group, -S(=O)2(OH)), phosphate group (-OP(=O)(OH)2), phosphonic acid group (-P(=O)(OH)2) and thioalkyl are monovalent groups.

[0733] In the above, amino, amide, and sulfonamide groups refer to monovalent groups or divalent groups of hydrogen atoms with hydrogen bonding. These monovalent groups refer to amino (-NH2), amide (-CONH2), and sulfonamide (-SO2NH2), respectively, and these divalent groups of hydrogen atoms with hydrogen bonding refer to amino (>NH), amide (-CONH-), and sulfonamide (-SO2NH-), respectively.

[0734] In the above, urethane group (-NHC(=O)O-) and urea group (-NR) a C(=O)NH-), thiocarbamate group (-NHC(=O)S- or -NHC(=S)O-) and thiourea group (-NR) a C(=S)NH-) is a divalent group of hydrogen atoms that has hydrogen bonding.

[0735] The above R a It is a hydrogen atom, an alkyl group, a monovalent aliphatic or aromatic heterocyclic group or a monovalent aromatic hydrocarbon cyclic group, preferably a hydrogen atom.

[0736] The hydrogen-bonding group of the above-mentioned structural unit (b2) is preferably at least one of hydroxyl, carboxyl, sulfonyl, phosphate, phosphonic acid, amino, thioalkyl, amide, carbamate, urea, thiocarbamate, thiourea and sulfonamide. From the viewpoint of further improving the tightness, it is more preferably at least one of hydroxyl, amide, carbamate and urea.

[0737] A structural unit may contain one or more hydrogen-bonding groups. If it contains more than two hydrogen-bonding groups, these hydrogen-bonding groups may be some or all the same, or they may be different hydrogen-bonding groups.

[0738] The polymer B described above preferably has a structural unit (b2) represented by the following general formula (p2).

[0739] [Chemical Formula 64]

[0740]

[0741] In the above formula, R P2 L represents a hydrogen atom or a methyl group. P2 R represents a single bond or a divalent linker. P3 This indicates a monovalent substituent. Where L... P2 and R P3 At least one of them contains at least one group selected from hydroxyl, carboxyl, sulfonyl, phosphate, phosphonic acid, amino, thioalkyl, amide, carbamate, urea, thiocarbamate, thiourea, and sulfonamide.

[0742] * indicates a bonding site used for binding into the polymer.

[0743] L P2 and R P3The description of at least one of the hydroxyl, carboxyl, sulfonyl, phosphoric acid, phosphonic acid, amino, thioalkyl, amide, carbamate, urea, thiocarbamate, thiourea, and sulfonamide groups as hydrogen-bonding groups of the above-mentioned structural unit (b2) is applicable.

[0744] Additionally, regarding -L P2 -R P3 The indicated groups are interpreted according to the following rules (i) to (iii). Rule (i) has the highest priority, followed by rule (ii), and finally rule (iii).

[0745] In the case of (i)-L P2 -R P3 Among the groups represented, the longest bonded chain starts from R. P2 When the number of bonded carbon atoms in the structure located at the very end (hereinafter referred to as the "terminal structure") corresponds to the monovalent group in the aforementioned hydrogen-bonded groups, R... P3 Interpreted as the monovalent group among the aforementioned hydrogen-bonded groups, and the remaining part interpreted as L... P2 .

[0746] (ii) In the case where the atom that does not belong to (i) above and is located on the last structural side of the above-mentioned structure, and constitutes the longest connecting chain, is a ring-forming atom, R P3 Interpreted as a monovalent cyclic group composed of a ring structure containing the cyclic atom, the remaining part is interpreted as L P2 Come,.

[0747] (iii) In cases not falling under (i) or (ii) above, the number of atoms constituting the longest bonded chain from the end of the aforementioned structure is counted up to R. P2 The bonded carbon atom side. The site where the atom forming the bond chain first becomes an oxygen, sulfur, nitrogen, or a carbon atom greater than C (=O) or greater than C (=S) is considered the site constituting the L. P2 In the atoms of R P3 To explain L using bonded atoms P2 and R P3 .

[0748] L P2 This indicates a single bond or a divalent linker.

[0749] As L P2 The divalent linking groups that can be used include alkylene, arylene, and those selected from -O-, -S-, >C(=O), >C(=S), and >NR. aThe groups in the group and the linking groups consisting of two or more of these groups.

[0750] R a The description of the hydrogen-bonding groups present in the above structural unit (b2) is applicable to R. a The records.

[0751] Able to form L P2 The alkylene and arylene groups can have substituents. As a group capable of forming L... P2 The alkylene and arylene groups may have substituents, for example, alkyl, cycloalkyl, alkoxy, acyl, acyloxy, alkoxycarbonyl, hydroxyl, carboxyl, sulfonyl, phosphate, phosphonic acid, amino (-N(R) X )2) Thioalkyl, amide (-CON(R) X )2 or -NR X COR Z ), sulfonamide group (-SO2N(R) X )2 or -NR X SO2R Z ), preferably hydroxyl groups. Additionally, R X It can be a hydrogen atom, an alkyl group, a monovalent aliphatic or aromatic heterocyclic group, or a monovalent aromatic hydrocarbon cyclic group, preferably a hydrogen atom. R Z It is a hydroxyl, alkyl, monovalent aliphatic or aromatic heterocyclic group or a monovalent aromatic hydrocarbon cyclic group, preferably a hydroxyl group.

[0752] The number of substituents is not particularly limited; for example, it can have 1 to 4 substituents.

[0753] As selected from -O-, -S-, >C (=O), >C (=S) and >NR above a Linking groups consisting of two or more groups, such as -OC(=O)-, -C(=O)O-, -OC(=O)O-, and -NR. a C(=O)-、-C(=O)NR a -、-OC(=O)NR a -、-NR a C(=O)O-, -SC(=O)-, -C(=O)S-, -OC(=S)O-, -SC(=O)O-, -OC(=O)S-, -NR a C(=S)-、-C(=S)NR a -、-SC(=O)NR a -、-OC(=S)NR a -、-NR a C(=S)O- or -NR aC(=O)S-, preferably -OC(=O)-, -C(=O)O-, -OC(=O)O-, -NR a C(=O)-、-C(=O)NR a -、-OC(=O)NR a -or-NR a C(=O)O-. Additionally, in the description of the linking group above, the left side is connected to R... P2 The bonded carbon atoms are bonded, with the right side connected to R. P3 Bonding. For example, if we take the linking group -OC (=O)- as an example, the left side refers to the ether bond side, and the right side refers to the carbonyl bond side. The same meaning applies below.

[0754] Furthermore, examples of compounds composed of alkylene or arylene groups and those selected from -O-, -S-, >C(=O), >C(=S), and >NR are also preferred. a The group consists of at least one of the following groups: a group consisting of a group consisting of a group consisting of two or more of these groups, or a linking group consisting of a combination of these groups. Examples include -C(=O)NH-alkylene, -C(=O)O-alkylene, -C(=O)NH-arylene, or -C(=O)O-arylene. Furthermore, it is also preferred to include groups further comprising -OC(=O)-, -C(=O)O-, or -NR groups on the alkylene group of -C(=O)NH-alkylene or -C(=O)O-alkylene, or the arylene group of -C(=O)NH-arylene or -C(=O)O-arylene. a C(=O)-、-C(=O)NR a -、-OC(=O)NR a -、-NR a C(=O)O-, -SC(=O)-, -C(=O)S-, -NR a C(=S)-、-C(=S)NR a -、-SC(=O)NR a -、-OC(=S)NR a -、-NR a C(=S)O- or -NR a The group C(=O)S-.

[0755] As L P2 Preferably, the single bond, -C(=O)NH-alkylene, -C(=O)O-alkylene, -C(=O)NH-arylene, -C(=O)O-arylene, or alkylene in -C(=O)NH-alkylene or -C(=O)O-alkylene, or arylene in -C(=O)NH-arylene or -C(=O)O-arylene further combined with -OC(=O)-, -C(=O)O-, -NR a C(=O)-、-C(=O)NRa -、-OC(=O)NR a -、-NR a C(=O)O-, -SC(=O)-, -C(=O)S-, -NR a C(=S)-、-C(=S)NR a -、-SC(=O)NR a -、-OC(=S)NR a -、-NR a C(=S)O- or -NR a The group C(=O)S-, more preferably a single bond, -C(=O)NH-alkylene, -C(=O)O-alkylene, -C(=O)NH-arylene, -C(=O)O-arylene, or an alkylene group in -C(=O)NH-alkylene or -C(=O)O-alkylene, or further combined with -OC(=O)-, -C(=O)O-, or -NR on the arylene group in -C(=O)NH-arylene or -C(=O)O-arylene. a C(=O)-、-C(=O)NR a -、-OC(=O)NR a -or-NR a The group C(=O)O-.

[0756] In addition, among the groups in the above combinations, the terminal groups -OC(=O)-, -C(=O)O-, and -NR a C(=O)-、-C(=O)NR a -、-OC(=O)NR a -、-NR a C(=O)O-, -SC(=O)-, -C(=O)S-, -NR a C(=S)-、-C(=S)NR a -、-SC(=O)NR a -、-OC(=S)NR a -、-NR a C(=S)O- or -NR a C(=O)S- can also be further combined with alkylene or arylene groups.

[0757] R P3 This indicates a monovalent substituent.

[0758] As R P3 The monovalent substituents are preferably alkyl, alkenyl, monovalent aliphatic or aromatic heterocyclic, aryl, hydroxyl, carboxyl, sulfonyl, phosphoric acid, phosphonic acid, thioalkyl, -NH2, -CONH2 and -SO2NH2.

[0759] As RP3 Preferably, the compounds are alkyl, alkenyl, aryl, hydroxyl, carboxyl, sulfonyl, phosphoric acid, phosphonic acid, thioalkyl, -NH2, -CONH2 or -SO2NH2, and more preferably alkyl, alkenyl, aryl or -CONH2.

[0760] As a structural unit represented by the above general formula (p2), the following structural units can be cited as examples. However, it is not limited to these structural units.

[0761] In addition, in the following chemical structural formulas, R represents a hydrogen atom or a methyl group.

[0762] [Chemical Formula 65]

[0763]

[0764] The proportion of structural units (b2) containing hydrogen-bonded groups in all structural units constituting polymer B is preferably 3 to 90% by mass, more preferably 4 to 80% by mass from the viewpoint of further improving adhesion, and more preferably 5 to 70% by mass from the viewpoint of further improving transmittance.

[0765] When polymer B has other structural units besides structural units (b1) and (b2), the proportion of structural unit (b2) containing hydrogen-bonded groups among all structural units constituting polymer B is preferably 3 to 30% by mass, more preferably 4 to 25% by mass, and even more preferably 5 to 20% by mass.

[0766] From the viewpoint of further improving the sealing performance and damp heat durability, polymer B is preferably a vinyl polymer, and more preferably a vinyl polymer having structural units (b1) represented by the aforementioned general formula (p1) and structural units (b2) represented by the aforementioned general formula (p2).

[0767] (b3) Other structural units

[0768] Polymer B may contain other structural units (hereinafter also referred to as "other structural units") besides the structural units (b1) and (b2) mentioned above.

[0769] As for the other structural units mentioned above, there are no particular limitations as long as they do not possess aromatic rings and the aforementioned hydrogen-bonding groups. Examples include structural units derived from commonly used monomers such as (meth)acrylate compounds, vinyl ester compounds, (meth)acrylonitrile compounds, and maleic anhydride compounds. By incorporating these structural units, it is possible to further improve transmittance and damp heat durability.

[0770] Among these, monomers selected from (meth)acrylate compounds and (meth)acrylonitrile compounds are preferred as monomers for deriving other structural units, and (meth)acrylate compounds are more preferred.

[0771] Specifically, examples include acrylate compounds such as alkyl acrylates (preferably with 1 to 20 carbon atoms in the alkyl group) (specifically, for example, methyl acrylate, ethyl acrylate, propyl acrylate, butyl acrylate, pentyl acrylate, ethylhexyl acrylate, octyl acrylate, tert-octyl acrylate, chloroethyl acrylate, glycidyl acrylate, methoxybenzyl acrylate, tetrahydrofurfuryl acrylate, etc.), methacrylate compounds such as alkyl methacrylates (preferably with 1 to 20 carbon atoms in the alkyl group) (for example, methyl methacrylate, ethyl methacrylate, propyl methacrylate, isopropyl methacrylate, pentyl methacrylate, hexyl methacrylate, cyclohexyl methacrylate, chlorobenzyl methacrylate, octyl methacrylate, glycidyl methacrylate, tetrahydrofurfuryl methacrylate, etc.), acrylonitrile, methacrylonitrile, etc.

[0772] From the viewpoint of further improving transmittance, alkyl (meth)acrylate compounds with alkyl groups having 4 to 20 carbon atoms are particularly preferred among the aforementioned monomers. By using polymer B containing structural units derived from such monomers as other structural units, the compatibility between the compound represented by general formula (1) in the aforementioned lens adhesive and polymer B can be improved, and the compatibility of other components can be improved, thereby obtaining a cured product with high transparency.

[0773] Furthermore, from the viewpoint of improving the adhesion to glass, polymer B is preferably composed of structural units derived from monomers (compounds) having alkoxysilyl groups as other structural units.

[0774] As a monomer having an alkoxysilyl group, it is not particularly limited as long as it is a compound having at least one alkoxy group directly bonded to a silicon atom and having a polymerizable group (preferably a free radical polymerizable group), but it is preferred to be a monomer having a dialkoxysilyl group and / or a trialkoxysilyl group and a polymerizable group, and more preferably a monomer having a trialkoxysilyl group and a polymerizable group.

[0775] Specifically, examples include γ-methacryloxypropyltrialkoxysilane, γ-methacryloxypropyldialkoxysilane, or vinyltrialkoxysilane. Among these, γ-methacryloxypropyltrialkoxysilane or γ-acryloxypropyltrialkoxysilane is more preferred.

[0776] These can be used individually or in combination of two or more.

[0777] When polymer B has other structural units, the proportion of other structural units in all structural units constituting the polymer is preferably 2 to 65% by mass, more preferably 3 to 45% by mass, and even more preferably 5 to 40% by mass.

[0778] (Molecular weight of polymer B)

[0779] The mass-average molecular weight (Mw) of polymer B is preferably 1,000 or more, more preferably 3,000 or more, and even more preferably 5,000 or more. Furthermore, the upper limit of the mass-average molecular weight is preferably 500,000 or less, more preferably 300,000 or less, and even more preferably 200,000 or less.

[0780] In this invention, the weight-average molecular weight is the weight-average molecular weight of polystyrene converted using GPC (Gel Permeation Chromatography), and is the value determined under the following test conditions. A suitable eluent can be appropriately selected based on the sample being tested.

[0781] (Measurement conditions)

[0782] Measuring instrument: HLC-8320GPC (trade name, manufactured by Tosoh Corporation)

[0783] Columns: Connected to TOSOH TSKgel HZM-H (trade name, manufactured by Tosoh Corporation), TOSOH TSKgel HZ4000 (trade name, manufactured by Tosoh Corporation), and TOSOH TSKgel HZ2000 (trade name, manufactured by Tosoh Corporation).

[0784] Carrier: THF

[0785] Measurement temperature: 40℃

[0786] Carrier flow rate: 0.35 mL / min

[0787] Sample concentration: 0.1% by mass

[0788] Detector: RI (Refractive Index) Detector

[0789] The following examples of polymer B are shown, but polymer B is not limited to these in this invention. Furthermore, in the following structural formulas, () refer to structural units, and the numbers recorded on the right side of each structural unit indicate the mass content ratio of that structural unit.

[0790] [Chemical Formula 66]

[0791]

[0792] [Chemical Formula 67]

[0793]

[0794] The content of polymer B in the above-mentioned lens adhesive is preferably 60% by mass or less, more preferably 50% by mass or less, and even more preferably 40% by mass or less. The lower limit is preferably 3% by mass or more, more preferably 5% by mass or more, and even more preferably 10% by mass or more.

[0795] ((meth)acrylate monomer)

[0796] The adhesive for the lens may also contain (meth)acrylate monomers. As the (meth)acrylate monomer, the same monomers mentioned in relation to the curable compositions of the present invention can be used.

[0797] Examples of preferred (meth)acrylate monomers contained in lens adhesives include monofunctional (meth)acrylate monomers with aromatic rings such as phenoxyethyl acrylate (monomer 1 above) or benzyl acrylate; (meth)acrylate monomers with aliphatic groups such as monomer a (2-ethylhexyl acrylate), monomer b (1,6-hexanediol diacrylate), and monomer c (1,6-hexanediol dimethacrylate); and (meth)acrylate monomers with hydroxyl groups such as monomer d (2-hydroxyethyl acrylate), monomer e (hydroxypropyl acrylate), or monomer f (4-hydroxybutyl acrylate).

[0798] [Chemical Formula 68]

[0799]

[0800] There are no particular restrictions on the methods for obtaining (meth)acrylate monomers; they can be obtained commercially or synthesized. When obtained through commercial means, Viscort#192PEA (phenoxyethyl acrylate) (manufactured by OSAKA ORGANIC CHEMICAL IND.LTD.), Viscort#160BZA (benzyl acrylate) (manufactured by OSAKA ORGANIC CHEMICAL IND.LTD.), 2EHA (monomer a) (manufactured by TOAGOSEI CO.,LTD.), A-HD-N (monomer b) (manufactured by Shin-Nakamura Chemical Co.,Ltd.), HD-N (monomer c) (manufactured by Shin-Nakamura Chemical Co.,Ltd.), HEA (monomer d) (manufactured by OSAKA ORGANIC CHEMICAL IND.LTD.), LIGHT ESTER HOP-A(N) (monomer e) (manufactured by Kyoishachemical Co.,Ltd.), and 4-HBA (monomer f) (manufactured by OSAKA ORGANIC CHEMICAL IND.LTD.) are preferred.

[0801] When the lens adhesive contains (meth)acrylate monomers, the content of (meth)acrylate monomers relative to the total mass of the lens adhesive is preferably 5 to 90% by mass, more preferably 10 to 85% by mass, and even more preferably 20 to 80% by mass. By adjusting the amount of (meth)acrylate monomers in the lens adhesive, the function of mitigating stress caused by heat deformation of the cured product can be adjusted.

[0802] (Polymerization initiator)

[0803] The adhesive for the lens preferably contains a photoradical polymerization initiator. As the photoradical polymerization initiator, the description of the photoradical polymerization initiator described in the compositions of the present invention is applicable.

[0804] Furthermore, in addition to the photoradical polymerization initiator, the adhesive for the lens may also contain a thermal radical polymerization initiator. By further containing a thermal radical polymerization initiator, curing of areas that cannot be reached by light can be promoted. As the thermal radical polymerization initiator, the thermal radical polymerization initiator described in the compositions of the present invention described above can be used.

[0805] [Manufacturing of the joint lens]

[0806] A bonded lens can be obtained by stacking two lenses together using a lens adhesive, followed by curing the adhesive to form an adhesive layer. Preferably, after stacking, air bubbles mixed into the adhesive are removed before curing.

[0807] The adhesive can be cured by light irradiation or heating. Curing is preferably carried out by at least light irradiation. Furthermore, a heating step can be performed after light irradiation. Regarding the curing of adhesives by light irradiation and heating, there are no particular limitations as long as an adhesive layer is formed, and curing can be carried out by conventional methods.

[0808] The thickness of the adhesive layer is preferably 10–50 μm, more preferably 20–30 μm. By setting the thickness to 10 μm or more, sufficient absorption of ultraviolet light can be achieved. Furthermore, by setting the thickness to 50 μm or less, high adhesion can be maintained while improving transmittance in the short wavelength region of visible light (400–430 nm).

[0809] The refractive index of the adhesive layer at a wavelength of 587 nm is preferably 1.51 or higher, more preferably 1.53 or higher, and even more preferably 1.55 or higher. This is because the difference in refractive index between the adhesive layer and the lens to which it is bonded is reduced.

[0810] Furthermore, in the adhesive layer with a film thickness of 30 μm, the cutoff wavelength is preferably 380 nm or less, more preferably 385 nm or less, and even more preferably 390 nm or less. Additionally, the wavelength at which the transmittance of the adhesive layer is 0.5% or less is defined as the cutoff wavelength. The transmittance of the adhesive layer can be measured using a spectrophotometer (e.g., the UV-2550 (trade name) manufactured by Shimadzu Corporation).

[0811] By adjusting the amount of the compound represented by general formula (1) in the lens adhesive, the refractive index and cutoff wavelength of the adhesive layer can be adjusted within the above range.

[0812] Example

[0813] The present invention will now be described in further detail with reference to embodiments. The materials, amounts, proportions, processing contents, and processing steps shown in the following embodiments can be appropriately modified without departing from the spirit of the invention. Therefore, the scope of the present invention should not be limited by the specific examples shown below.

[0814] In addition, the preparation process of the curing composition and the storage process of the prepared curing composition until the production of the cured product were carried out in an environment using yellow light as illumination.

[0815] [Synthesis example]

[0816] Component A was synthesized as follows.

[0817] Additionally, the abbreviations used for the synthesis of each compound shown below are for the following compounds. Furthermore, w / v% refers to the percentage of mass relative to volume, and room temperature refers to 25°C.

[0818] EDAC: 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride

[0819] MEK: Methyl Ethyl Ketone

[0820] THF: Tetrahydrofuran

[0821] Et: Ethyl

[0822] In addition, HPLC and transmittance measurements were performed according to the methods shown below.

[0823] (HPLC determination)

[0824] The purity of the compound was determined using a high-performance liquid chromatography (HPLC) instrument manufactured by Shimadzu Corporation (trade name: SPD-10AV VP) under the following conditions. Furthermore, the HPLC purity was calculated by subtracting the peaks originating from the solvent when the compound was solvated.

[0825] Column: TSKgel ODS-100Z 5μm (4.6mmφ×150mm) (manufactured by Tosoh Corporation)

[0826] Column temperature: 40℃

[0827] Eluent: Acetonitrile: Pure water: Phosphoric acid (volume ratio) = 700:300:1

[0828] Flow rate: 1.0 mL / min

[0829] Detection wavelength: 254nm

[0830] Injection volume: 10μL

[0831] Sample: Dissolve the compound in the eluent to achieve a concentration of 5 mg / 50 ml.

[0832] (Transmittance Measurement)

[0833] The transmittance of the compound at a wavelength of 420 nm was measured using a spectrophotometer (trade name: UV-2550) manufactured by Shimadzu Corporation under the following conditions. Higher transmittance at 420 nm indicates less coloration.

[0834] Cell: Square quartz cell (optical path length: 1cm)

[0835] Sample: Dissolve the compound in THF to achieve a concentration of 50 mg / 5 mL.

[0836] Blank culture medium: THF (solvent)

[0837] [1. Synthesis of starting material compounds (A4) and (A5)]

[0838] Following the synthesis of compounds (SA-4) and (SA-5), starting compounds (A4) and (A5) were synthesized as follows.

[0839] <Synthesis of Compound (SA-4)>

[0840] [Chemical Formula 69]

[0841]

[0842] 9.9 g of compound (SM-4) and 40 mL of dichloromethane were added to a 500 mL three-necked flask. While cooling in an ice bath, 40 mL of trifluoroacetic acid and 15.2 g of triethylsilane were added. Then, 12.4 g of boron trifluoride-diethyl ether complex was added dropwise over 30 minutes, and the mixture was allowed to react at 40 °C for 3 hours. After cooling to room temperature, 180 mL of cyclopentyl methyl ether was added, and the mixture was stirred further for 2 hours. The precipitated solid was recovered by filtration and dried under vacuum in a reduced-pressure oven to obtain 6.2 g of compound (SA-4) (yield 66.0%).

[0843] <Synthesis of Compound (SA-5)>

[0844] Compound (SM-4) was replaced with compound (SM-5), and 8.2 g of compound (SA-5) (yield 86.5%) was obtained in the same manner as the synthesis of compound (SA-4) described above.

[0845] [Chemical Formula 70]

[0846]

[0847] [Synthetic Example 1-1: Synthesis of Compound (A4)]

[0848] [Chemical Formula 71]

[0849]

[0850] 5.0 g of compound (SA-4), 6.9 g of ethyl acrylate, and 50 mL of N,N-dimethylacetamide were added to a 200 mL three-necked flask and stirred at room temperature for 10 minutes. Then, 2.9 g of a 40% by weight methanol solution of benzyltrimethylammonium hydroxide was added, and the mixture was reacted at 80 °C for 1 hour. After confirming the disappearance of the starting compound (SA-4) by TLC, 7.5 mL of water and 7.5 mL of a 50 w / v% sodium hydroxide aqueous solution were added, and the mixture was stirred at 80 °C for 1 hour to hydrolyze the ethyl acrylate. After cooling to room temperature, the mixture was neutralized with hydrochloric acid of a specified concentration (6%), and ethyl acetate was added, followed by separation. The organic layer was washed with hydrochloric acid of a specified concentration and saturated brine, and then dried with magnesium sulfate. After removing the magnesium sulfate by filtration, the solvent was concentrated, and the precipitated solid was dispersed and washed with a mixed solvent of ethyl acetate and hexane to obtain 6.2 g of compound (A4) (78% yield). The area percentage of compound (A4), determined by HPLC, was 97.6%, while the content of the starting compound (SA-4) was less than 0.1%. Furthermore, compound (A4) had a transmittance of 98.9% at 420 nm.

[0851] Compound (A4) 1 H-NMR data (400MHz, DMSO-d6): δ1.50-1.75ppm (m, 4H), 2.35-2.55ppm (m, 10H), 7.55ppm (t, 1H ), 7.62ppm (t, 1H), 7.76ppm (d, 1H), 7.90-7.95ppm (m, 2H), 8.10ppm (d, 1H), 12.0ppm (s, 2H)

[0852] [Synthetic Examples 1-2: Synthesis of Compound (A5)]

[0853] [Chemical Formula 72]

[0854]

[0855] Compound (SA-4) was replaced with compound (SA-5), and otherwise, 6.7 g of compound (A5) (yield 89%) was obtained in the same manner as in Synthesis Example 1-1. The area % of compound (A5) determined by HPLC was 95.9%, and the content of compound (SA-5) as the starting material was less than 0.1%. Furthermore, the transmittance of compound (A5) at 420 nm was 98.7%.

[0856] Compound (A5) 1H-NMR data (400MHz, DMSO-d6): δ1.55-1.80ppm (m, 4H), 2.35-2.55ppm (m, 4H), 7.60ppm (t, 1H ), 7.75ppm (t, 1H), 7.80ppm (d, 1H), 8.12ppm (d, 1H), 8.40-8.50ppm (m, 2H), 12.0ppm (s, 2H)

[0857] [Synthetic Example 2-1: Synthesis of Compound (A4-1)]

[0858] [Chemical Formula 73]

[0859]

[0860] A mixture of 4.0 g of compound (A4), 20 mL of dichloromethane, 3.3 g of 2-hydroxyethyl methacrylate, 0.1 g of N,N-dimethylaminopyridine, and 4.9 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride was prepared. After stirring at 40 °C for 2 hours, 1 N hydrochloric acid was added for washing and separation. Then, 5% sodium bicarbonate aqueous solution was added for washing and separation. After dehydration with magnesium sulfate, filtration, and concentration, the mixture was purified by column chromatography (eluent: a mixture of chloroform and methanol) to obtain 4.4 g of compound (A4-1) (yield 70%).

[0861] Compound (A4-1) 1 H-NMR (400MHz, CDCl3): δ=1.65-1.85ppm (m, 4H), 1.89ppm (s, 6H), 2.35-2.45ppm (m, 2H), 2.50ppm (s, 3H), 2.52ppm (s, 3H), 2.65-2.75ppm (m, 2H), 4.15-4.25ppm (m, 8H), 5.55ppm (s, 2H), 6.05ppm (s, 2H), 7.55-7.65ppm (m, 3H), 7.88ppm (s, 1H), 7.92ppm (s, 1H), 8.20ppm (d, 2H)

[0862] For compound (A4-1), the absorption spectrum (absorbance) was determined by the following steps.

[0863] Accurately weigh 50 mg of the compound, dilute it with tetrahydrofuran (THF) in a 5 mL volumetric flask, and then further dilute it with THF to a concentration of 1 / 500 to prepare the assay solution. The assay was performed using a UV-2550 (trade name) manufactured by Shimadzu Corporation.

[0864] First, square quartz cells (10 mm in length) containing the control sample (THF) were placed in both the sample optical path and the control optical path, and the absorbance in the wavelength range of 250–800 nm was adjusted to zero. Next, the sample in the cell of the sample optical path was replaced with the assay solution of the compound prepared above, and the absorption spectrum in the range of 250–800 nm was measured.

[0865] The wavelength λmax of the maximum peak located on the longest wavelength side in the range of 300-400 nm, obtained from the measurement results, is 369 nm.

[0866] [Synthetic Example 2-2: Synthesis of Compound (A5-1)]

[0867] [Chemical Formula 74]

[0868]

[0869] Compound (A4) was replaced with compound (A5), and otherwise, 5.1 g of compound (A5-1) (yield 84%) was obtained in the same manner as in Synthesis Example 2-1.

[0870] Compound (A5-1) 1 H-NMR (400MHz, CDCl3): δ=1.65-1.85ppm (m, 4H), 1.89ppm (s, 6H), 2.35-2.45ppm (m, 2H), 2.65-2.75ppm (m, 2H), 4.15-4. 25ppm (m, 8H), 5.55ppm (s, 2H), 6.05ppm (s, 2H), 7.55-7.65ppm (m, 3H), 8.16ppm (d, 1H), 8.24ppm (s, 1H), 8.28ppm (s, 1H)

[0871] The wavelength λmax of the maximum peak located on the longest wavelength side in the 300–400 nm range of compound (A5-1) was measured in the same manner as compound (A4-1), and was 372 nm.

[0872] [Synthetic Example 3: Synthesis of Polymer (P-4)]

[0873] According to Example 1 of paragraph

[0331] of Japanese Patent Application Publication No. 2021-1328, particles of the polymer (P-4) were synthesized and used as resin composition No. c14. Furthermore, the polymer (P-4) has a mass-average molecular weight of 29,000.

[0874] Furthermore, following Example 1 of Japanese Patent Application Publication No. 2021-1328, paragraph

[0331] , a two-stage reaction was carried out. After the reaction was stopped by pressurizing the gas to atmospheric pressure with nitrogen to synthesize the polymer (P-4), compound (B-9) (octocrylene, manufactured by Tokyo Chemical Industry Co., Ltd.) or methyl cinnamate was added and compounded to achieve the formulation ratio described in the table below. The obtained compound was extruded into water, and resin particle samples (resin compositions No. 105, c15, and c16) were prepared by cutting the filament.

[0875] [Chemical Formula 75]

[0876]

[0877] <Example 1: Curable Composition and Cured Product>

[0878] (1) Preparation of curable compositions (compositions No. 101-104, 106-116, c11-c13)

[0879] The components were mixed to form the composition described in the table below, and stirred until homogeneous, thereby preparing a curable composition.

[0880] (2) Preparation of photocurable samples

[0881] The prepared composition was injected into a 20 mm diameter circular transparent glass mold (made of borosilicate glass with a hydrophobic surface treated with dichlorodimethylsilane) to achieve a cured product thickness of 500 μm. Using an Execure3000 (trade name, manufactured by HOYA Corporation) as the light source, and with a short-wavelength cutoff filter LU0422 (trade name, manufactured by Asahi Spectra Co., Ltd.) placed between the light source and the transparent glass mold, the mixture was irradiated from above at 1000 mJ / cm² in an atmosphere where nitrogen substitution was performed to reduce the oxygen concentration to below 1%. 2 Ultraviolet light was used to prepare photocured samples. Then, under an atmosphere where nitrogen substitution was performed to reduce the oxygen concentration to below 1%, the samples were heated at 200°C for 30 minutes and then cooled to room temperature to serve as evaluation samples.

[0882] The curing reaction is completed through the above-mentioned ultraviolet irradiation process, and all cured products are obtained as fully cured products.

[0883] <Example 2: Resin composition (Composition No. 105, c14-c16) and its molded article>

[0884] Using a spacer with a thickness of 500 μm, a polyimide film was coated on the top and bottom of the resin particle sample prepared above. The sample was preheated at a temperature of 200–230 °C for 3 minutes, pressurized at a pressure of 7 MPa for 5 minutes, and then removed together with the spacer. The sample was then cooled to room temperature and used as an evaluation sample.

[0885] In addition, compositions No. 101 to 116 are compositions of the present invention, and compositions No. c11 to c16 are comparative compositions.

[0886] [Evaluation 1: Transmittance before irradiation test]

[0887] The UV-Vis transmittance of the center portion (5 mm in diameter) of the obtained evaluation sample was measured using a UV-2600 UV-Vis spectrophotometer (trade name, manufactured by Shimadzu Corporation), and the transmittance at a wavelength of 430 nm (before the irradiation test) was determined.

[0888] [Evaluation 2: Transmittance after 48 hours of xenon light irradiation]

[0889] Evaluation samples prepared using compositions No. 101-116 and No. c11-c16 were subjected to xenon irradiation tests under the following conditions. This irradiation test is equivalent to an accelerated lightfastness test under sunlight.

[0890] For the evaluation samples after the xenon irradiation test, the transmittance at a wavelength of 430 nm (after the irradiation test) was determined by the method described in Evaluation 1: Transmittance before the irradiation test.

[0891] (Xenon light irradiation conditions)

[0892] Apparatus: Q-SUN Xe-1 Xenon-Accelerated Weathering Tester (trade name, manufactured by Q-Lab Corporation)

[0893] Light source: Xenon arc lamp

[0894] Filter: Extended UV Q / B (trade name, manufactured by Q-Lab Corporation)

[0895] Illuminance: 0.43 W / m 2 (340nm illuminance meter)

[0896] Black panel temperature: 63℃

[0897] Test duration: 48 hours

[0898] [Evaluation 3: The decrease in xenon light intensity before and after 48 hours of irradiation]

[0899] The difference between the transmittance at a wavelength of 430 nm obtained in Evaluation 1 above (before the irradiation test) and the transmittance at a wavelength of 430 nm obtained in Evaluation 2 above (after the irradiation test) is taken as the decrease in transmittance before and after the irradiation test.

[0900] <Optical Property Measurement>

[0901] For the cured products of the curable composition obtained in Example 1 and the molded articles of the resin composition obtained in Example 2, the refractive index (nD), Abbe number (νD), and partial dispersion ratio (θg, F value) were measured using an Abbe refractometer (ATAGO CO., LTD, manufactured, trade name: DR-M4). Each sample was measured three times at 25°C, and the average value was taken as the result.

[0902] "Refractive index (nD)" is the refractive index at a wavelength of 587.56 nm. Furthermore, "Abbe number (νd)" and "partial dispersion ratio (θg, F value)" are values ​​calculated from the refractive index measurements at different wavelengths using the following formulas.

[0903] νD=(nD-1) / (nF-nC)

[0904] θg, F=(ng-nF) / (nF-nC)

[0905] Here, nD represents the refractive index at a wavelength of 589 nm, nF represents the refractive index at a wavelength of 486 nm, nC represents the refractive index at a wavelength of 656 nm, and ng represents the refractive index at a wavelength of 436 nm.

[0906] The cured products obtained from curable compositions No. 101–104, 106–116 and the molded articles obtained from resin composition No. 105 have Abbe numbers as low as 26–20 and partial dispersion ratios as high as 0.72–0.86, which meet the abnormal dispersion of refractive index required by chromatic aberration correction lenses.

[0907]

[0908]

[0909]

[0910] The ingredients in the table are as follows. Additionally, the proportions of each ingredient are based on mass; a "-" indicates that the ingredient is not present.

[0911] (ingredient A)

[0912] [Chemical Formula 76]

[0913]

[0914] In addition, compound (A-35) was synthesized according to synthesis example 9 [synthesis of A-35] described in paragraph

[0256] of International Publication No. 2020 / 009053.

[0915] Compound (VI-2) was synthesized according to the [synthesis of compound (VI-2)] described in paragraph

[0233] of International Publication No. 2020 / 009053.

[0916] Compound (A-28) was synthesized according to the synthetic method of compound (27) described in paragraph

[0139] of International Publication No. 2017 / 115649.

[0917] (Other monomers)

[0918] [Chemical Formula 77]

[0919]

[0920] (Ingredient B)

[0921] [Chemical Formula 78]

[0922]

[0923] In addition, compound (B-50) was synthesized with reference to Example 3 of U.S. Patent No. 4,218,392.

[0924] Compound (B-56) was synthesized with reference to Example 5 of U.S. Patent No. 4,218,392.

[0925] (Comparison using compounds)

[0926] [Chemical Formula 79]

[0927]

[0928] (Photopolymerization initiator)

[0929] Irg819: Irgacure 819 (product name, manufactured by BASF Japan Ltd.)

[0930] (Thermal polymerization initiator)

[0931] PERBUTYL D: Trade name, manufactured by NOF CORPORATION, di-tert-hexyl peroxide

[0932] The following information can be obtained from the results in Table 1.

[0933] Comparative composition No. C11 does not contain component B specified in this invention and is therefore not a composition specified in this invention. The transmittance of the cured product obtained from comparative composition No. C11 decreased significantly to 45% before and after the light irradiation test, indicating poor lightfastness. Furthermore, comparative compositions No. C12 and C13 are not compositions specified in this invention as they use methyl cinnamate instead of component B specified in this invention. The transmittance of the cured products obtained from these comparative compositions No. C12 and C13 decreased by 17% before and after the light irradiation test, indicating poor lightfastness. In particular, in comparative composition No. C13, although twice the amount of methyl cinnamate compared to comparative composition No. C12 was used, there was no difference in the decrease in transmittance before and after the light irradiation test, suggesting that further reduction in transmittance cannot be achieved when using methyl cinnamate.

[0934] In contrast, the cured products obtained from the curable compositions No. 101-104, 106-116 of the present invention exhibit excellent transmittance before the light irradiation test, and also show excellent transmittance after the light irradiation test, indicating that the decrease in transmittance can be suppressed.

[0935] Furthermore, comparative composition No. c14 does not contain component B specified in this invention and is therefore not a composition specified in this invention. The transmittance of the molded body obtained from comparative composition No. c14 decreased significantly to 49% before and after the light irradiation test, indicating poor lightfastness. Furthermore, comparative compositions No. c15 and c16 are not compositions specified in this invention as they use methyl cinnamate to replace component B specified in this invention. The transmittance of the molded bodies obtained from these comparative compositions No. c15 and c16 decreased by 23% before and after the light irradiation test, indicating poor lightfastness. In particular, in comparative composition No. c16, although twice the amount of methyl cinnamate compared to comparative composition No. c15 was used, there was no difference in the decrease in transmittance before and after the light irradiation test, suggesting that no further reduction in transmittance can be achieved when using methyl cinnamate.

[0936] In contrast, the molded article obtained from the resin composition No. 105 of the present invention exhibits excellent transmittance before the light irradiation test and also shows excellent transmittance after the light irradiation test, indicating that the decrease in transmittance can be suppressed.

[0937] Thus, since the cured products obtained from the curable composition of the present invention and the molded articles obtained from the resin composition of the present invention have excellent light resistance, even when optical components and lenses containing these cured products or molded articles as constituent parts are used in outdoor light irradiation environments for a long time, coloring can be suppressed.

[0938] <Reference Example 1 (Fabrication of a Composite Lens Using the Composition of the Invention)>

[0939] (1) Preparation of curable compositions (compositions No. 117-125)

[0940] The components were mixed to form the composition described in the table below, and stirred until homogeneous, thereby preparing a curable composition (compositions No. 117-125).

[0941] (2) Fabrication of compound lenses

[0942] A composite lens was fabricated under an atmosphere where nitrogen substitution was performed to reduce the oxygen concentration to below 1%. Specifically, 50 mg of the curing composition was injected into a biconcave glass lens A (glass material: BK7, outer diameter 10 mm, radius of curvature of the surface in contact with the curing composition 12 mm, radius of curvature of the other surface 10 mm), and a chromium nitride-treated molding die was placed over it and unfolded to make the diameter of the curing composition 10 mm. At this point, the film thickness of the curing composition layer in the center was approximately 600 μm. After setting it to this state, an Execure3000 (trade name, manufactured by HOYACorporation) was used as the light source, and a short-wavelength cutoff filter LU0422 (trade name, manufactured by Asahi Spectra Co., Ltd.) was placed between the light source and the glass lens A, and 300 mJ / cm² light was irradiated from above the glass lens A. 2 Ultraviolet rays.

[0943] Next, while maintaining the mixture between the molding die and glass lens A, a pressure of 0.196 MPa (2 kgf / cm²) is applied to the curable composition. 2 The pressure was applied while the temperature was raised to 200°C. Then, a composite lens was produced by separating the cured product of the curable composition from the molding die at a speed of 0.05 mm / sec.

[0944] [Evaluation 4: Transmittance before irradiation test]

[0945] The UV-Vis transmittance of the central portion (5 mm in diameter) of the obtained composite lens was measured using a UV-2600 UV-Vis spectrophotometer (trade name, manufactured by Shimadzu Corporation), and the transmittance at a wavelength of 430 nm (before the irradiation test) was determined.

[0946] [Evaluation 5: Transmittance after 240 hours of xenon light irradiation]

[0947] For composite lenses made using compositions No. 117-125, xenon irradiation tests were conducted under the following conditions. This irradiation test is equivalent to an accelerated lightfastness test under sunlight.

[0948] For the composite lens after the xenon irradiation test, the transmittance at a wavelength of 430 nm (after the irradiation test) was determined using the method described in Evaluation 4: Transmittance before the irradiation test.

[0949] (Xenon light irradiation conditions)

[0950] Apparatus: Q-SUN Xe-1 Xenon-Accelerated Weathering Tester (trade name, manufactured by Q-Lab Corporation)

[0951] Light source: Xenon arc lamp

[0952] Filter: Extended UV Q / B (trade name, manufactured by Q-Lab Corporation)

[0953] Illuminance: 0.43 W / m 2 (340nm illuminance meter)

[0954] Black panel temperature: 63℃

[0955] Test duration: 240 hours

[0956] [Evaluation 6: The decrease in xenon light intensity before and after 240 hours of irradiation]

[0957] The difference between the transmittance at a wavelength of 430 nm obtained in Evaluation 4 above (before the irradiation test) and the transmittance at a wavelength of 430 nm obtained in Evaluation 5 above (after the irradiation test) is taken as the decrease in transmittance before and after the irradiation test.

[0958] [Evaluation 7: Thermal Shock Resistance of Composite Lenses]

[0959] Thirty composite lenses using compositions No. 117 to 125 were manufactured following the same procedures as those used in the fabrication of the aforementioned composite lenses. To confirm the thermal shock resistance of the obtained composite lenses, they were heated at 100°C for 48 hours, then allowed to cool naturally to room temperature, and further cooled to -40°C. After 48 hours, they were placed in a room temperature environment to allow them to return to room temperature. Each composite lens was visually evaluated and inspected for cracks or peeling using a microscope (trade name: VHX-1000, manufactured by KEYENCE CORPORATION, magnification: 200x). Lenses showing no observed changes before and after the test were classified as good products. The percentage of good products out of the 30 was used as the yield rate, and the thermal shock resistance was evaluated according to the following criteria.

[0960] -Evaluation Criteria-

[0961] A: The yield rate is over 90%.

[0962] B: The yield rate is above 80% but less than 90%.

[0963] C: The yield rate is above 70% but less than 80%.

[0964] D: The yield rate is less than 70%.

[0965]

[0966]

[0967] The components listed in the table are as described in Table 1 above. Furthermore, the proportions of each component are based on mass; a "-" indicates that the component is not present.

[0968] Based on the results in Table 2, the following information can be obtained.

[0969] Composite lenses made using the curable compositions No. 117 to 125 of the present invention exhibit excellent transmittance before the light irradiation test of the cured material, and also show excellent transmittance after 240 hours of xenon light irradiation. This indicates that the decrease in transmittance can be suppressed and that they have excellent light resistance.

[0970] Furthermore, it is known that composite lenses made using the curable compositions No. 117 to 125 of the present invention exhibit suppressed appearance changes such as cracks or peeling after thermal shock testing, and also demonstrate excellent thermal shock resistance.

[0971] Thus, the composite lens made using the composition of the present invention has excellent light resistance that is no less than that of the cured product made using the curable composition of the present invention or the molded article made using the resin composition of the present invention, and also has excellent thermal shock resistance.

[0972] <Reference Example 2 (Fabrication of a bonded lens using the composition of the present invention and a UV-blocking adhesive)>

[0973] Synthesis of monomer I-6 for adhesives

[0974] [Chemical Formula 80]

[0975]

[0976] Synthesis of Compound (I-6A0)

[0977] The synthesis was carried out using the same synthetic method as that described in Bulletin of the Chemical Society of Japan, 81, 1518, for ethyl 11-bromoundecanoate (compound (I-6A0)). The yield was 90%.

[0978] <Synthesis of Compound (I-6A)>

[0979] While mixing 36.9 g (125.8 mmol) of compound (I-6A0), 15 g (57.2 mmol) of compound (I-1D), 17.4 g (125.8 mmol) of potassium carbonate, 60 mL of THF, and 90 mL of N,N-dimethylacetamide, the mixture was heated to an internal temperature (liquid temperature) of 80 °C. After stirring at 80 °C for 3 hours, 150 mL of ethyl acetate, 180 mL of water, and 30 mL of concentrated hydrochloric acid were added and stirred, followed by washing and separation. Next, 150 mL of 5% sodium bicarbonate aqueous solution was added and stirred, followed by washing and separation. Then, 230 mL of methanol was added to the organic layer, and the precipitated crystals were filtered to obtain compound (I-6A). The yield was 65%.

[0980] <Synthesis of Compound (I-6B)>

[0981] 20 g (30.6 mmol) of compound (I-6A), 20 mL of concentrated hydrochloric acid, 240 mL of acetic acid, and 80 mL of water were mixed and stirred at 80 °C for 1 hour. The mixture was then cooled to 25 °C, 200 mL of water was added, and the precipitated solid was filtered off. The mixture was then washed with methanol and water and dried at 50 °C to obtain compound (I-6B). The yield was 90%.

[0982] <Synthesis of Compound (I-6) (Monomer I-6 for Adhesives)>

[0983] 18 g (28.5 mmol) of carboxylic acid compound (I-6B), 45 mL of ethyl acetate, 9.1 g (62.8 mmol) of hydroxypropyl methacrylate, 0.4 g (2.9 mmol) of N,N-dimethylaminopyridine, and 12 g (62.8 mmol, abbreviation: EDAC) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride were mixed. After stirring at 40 °C for 2 hours, 300 mL of 1N hydrochloric acid was added for washing and separation. Then, 5% sodium bicarbonate aqueous solution was added for washing and separation. The mixture was dehydrated with magnesium sulfate, filtered, and concentrated to obtain an oily composition. This oily composition was then purified by column chromatography to obtain compound (I-6). The yield was 70%.

[0984] 1H-NMR (300MHz, CDCl3): δ (ppm) 1.25-1.50 (m, 30H), 1.50-1.70 (m, 8H), 1.95 (s, 6H), 2.20-2.40 (m, 7H) ,3.85(t,2H),4.0(t,2H),4.10-4.30(m,4H),5.10-5.30(m,2H),5.60(s,2H),6.10(s,2H),6.70(s,1H)

[0985] Synthesis of polymer P10 for adhesives

[0986] [Chemical Formula 81]

[0987]

[0988] 20.0 g of benzyl methacrylate (manufactured by FUJIFILM Wako Pure Chemical Corporation), 18.0 g of tert-butyl methacrylate (manufactured by FUJIFILM Wako Pure Chemical Corporation), and 2.0 g of 2-hydroxyethyl methacrylate (manufactured by Tokyo Chemical Industry Co., Ltd.) were dissolved in 50 mL of cyclohexanone, and the solution was heated to 80 °C under a nitrogen atmosphere. A solution containing 1.0 g of polymerization initiator (manufactured by FUJIFILM Wako Pure Chemical Corporation, trade name: V-601) was added dropwise to this solution over 30 minutes, and the mixture was allowed to react at 80 °C for 6 hours. After stopping the nitrogen flow and setting the reaction solution temperature to 70°C, 0.12 g of 2-tert-butyl-1,4-benzoquinone (manufactured by Tokyo Chemical Industry Co., Ltd.), 0.14 g of bismuth tris(2-ethylhexanoate) (manufactured by NITTO KASEI CO., LTD., trade name: NEOSTANN U-600), and 4.4 g of ethyl isocyanate acrylate (manufactured by SHOWA DENKO KK, trade name: Karenz AOI) were added, and the reaction was allowed to proceed at 70°C for 8 hours. After naturally cooling the reaction solution, it was added dropwise to a mixture of 200 mL of water and 1800 mL of methanol, and the precipitated powder was obtained by filtration and dried, thus yielding 30 g of polymer P10. The mass-average molecular weight (Mw) of the obtained polymer P10 was 19,000.

[0989] (1) Preparation of adhesive composition 1

[0990] 3.0 g of adhesive was mixed with monomer I-6, 3.0 g of polymer P10, 2.0 g of dodecyl acrylate, 2.0 g of 4-hydroxybutyl acrylate, and 40 mg of Irgacure 819 (trade name, manufactured by BASF Japan Ltd.) as a photopolymerization initiator, and stirred until homogeneous, thereby preparing adhesive composition 1.

[0991] (2) Fabrication of compound lenses

[0992] A composite lens was fabricated under an atmosphere where nitrogen substitution was performed to reduce the oxygen concentration to below 1%. Specifically, 50 mg of curing composition No. 101 was injected into a biconcave glass lens A (glass material: BK7, outer diameter 10 mm, radius of curvature of the surface in contact with curing composition No. 101 is 12 mm, and the radius of curvature of the other surface is 10 mm). A molding die with a chromium nitride treatment was then placed over the lens and expanded to make the diameter of curing composition No. 101 10 mm. At this point, the film thickness of the curing composition No. 101 layer in the center was approximately 600 μm. After setting this state, an Execure3000 (trade name, manufactured by HOYA Corporation) was used as the light source, and a short-wavelength cutoff filter LU0422 (trade name, manufactured by Asahi Spectra Co., Ltd.) was placed between the light source and the glass lens A. The lens was then irradiated from above with 300 mJ / cm² light. 2 Ultraviolet rays.

[0993] Next, while maintaining the mixture between the molding die and glass lens A, a pressure of 0.196 MPa (2 kgf / cm²) is applied to the curable composition No. 101. 2 The pressure was applied while the temperature was raised to 200°C. Then, by separating the cured product of curable composition No. 101 from the molding die at a speed of 0.05 mm / sec, a composite lens 1 formed of biconcave glass lens A and the cured product of curable composition No. 101 was produced.

[0994] (3) Fabrication of the joint lens

[0995] Inside the nitrogen substitution chamber, the composite lens 1 prepared above was placed horizontally, and the adhesive composition 1 prepared above was applied to the cured surface of curable composition No. 101. Next, a biconvex glass lens B (glass material: BK7, outer diameter 10 mm, with a radius of curvature of 12 mm on the surface where it intersects with the biconcave glass lens A, and a radius of curvature of 10 mm on the other side) was stacked on top of the applied adhesive composition 1 and spread out to prevent air bubbles from entering. At this time, the coating amount was adjusted so that the film thickness of the adhesive composition 1 layer in the center was 20 μm. Then, under an atmosphere with an oxygen concentration of less than 1%, 300 mJ / cm² was irradiated from the biconvex glass lens B side using an Execure3000 (trade name, manufactured by HOYA Corporation). 2 Ultraviolet light is used to cure the adhesive composition 1 to produce a bonded lens 1 having a structure consisting of a cured biconcave glass lens A, a cured curable composition No. 101, a cured adhesive composition 1, and a biconvex glass lens B stacked sequentially.

[0996] For the obtained bonding lens 1, the transmittance before and after 48 hours of xenon light irradiation was measured in the same manner as in the aforementioned evaluations 1 to 3, and the decrease in transmittance before and after the irradiation test was calculated. In addition, during xenon light irradiation, the bonding lens 1 was configured such that light entered from the biconvex glass lens B side of the bonding lens 1.

[0997] The transmittance before xenon light irradiation at 430 nm was 77%, while the transmittance after xenon light irradiation at 430 nm was 72%, showing a decrease in transmittance of 5%, indicating excellent lightfastness. This means that the bonding lens made using the curable composition No. 101 of the present invention has excellent lightfastness comparable to that of a circular cured object made using the curable composition No. 101 of the present invention. Furthermore, it is indicated that the bonding lenses made using the curable compositions No. 102-104, 106-116 of the present invention or the resin composition No. 105 of the present invention also have excellent lightfastness comparable to that of a circular cured object made using the corresponding curable composition in Example 1.

[0998] Thus, the bonding lens made using the composition of the present invention has excellent lightfastness that is no less than that of a cured product made using the curable composition of the present invention or a molded article made using the resin composition of the present invention.

[0999] The invention has been described together with its embodiments, but we believe that, unless otherwise specified, any details described are not intended to limit our invention, but should be interpreted broadly without departing from the spirit and scope of the invention as set forth in the appended claims.

[1000] This application claims priority based on Japanese Patent Application No. 2021-091394, filed in Japan on May 31, 2021, and Japanese Patent Application No. 2022-070906, filed in Japan on April 22, 2022, the contents of which are incorporated herein by reference and are part of the description herein.

Claims

1. A composition comprising component A and component B: Component A: A compound containing a nitrogen-fused aromatic ring as part of its structure; Component B: A compound represented by any one of the following general formulas (B1) to (B5), [Chemical Formula 1] In the above formula, Ar 101 ~Ar 104 X represents aryl or heteroaryl. 1 Y represents a monovalent substituent. 1 Ar represents a hydrogen atom or a monovalent substituent. 101 ~Ar 104 X 1 and Y 1 Two adjacent elements in the loop can bond together to form a ring, wherein... as X 1 or Y 1 none of the monovalent substituents employed are aryl or heteroaryl groups, Component A is a compound represented by the following general formula (A1) or (A2) or a polymer having structural units represented by the following general formula (A3) or (A4). [Chemical Formula 2] In the above formula, R 3 and R 4 represent a hydrogen atom or a monovalent substituent, L 1 and L 2 represent an alkylene group having 1 to 6 carbon atoms, an arylene group having 6 to 10 carbon atoms, or a heteroarylene group having 5 to 10 ring-forming atoms, LL represents a single bond or a divalent linking group, Sp a to Sp d represent a single bond or a divalent linking group, Pol 1 and Pol 2 Represents a hydrogen atom or a polymeric group, where Pol 1 and Pol 2 At least one of them is a polymeric group. Ring Ar 1 Ar represents an aromatic ring represented by the following formula (AR1), or a fused ring containing such an aromatic ring as a constituent ring of a fused ring. 2 This represents an aromatic ring represented by the following formula (AR2), or a fused ring containing the aromatic ring as a constituent ring, wherein ring Ar 1 and the ring Ar 2 One of them is the nitrogen-containing fused aromatic ring, and the other is a 6-membered aromatic monocyclic ring. The number of rings constituting the nitrogen-containing fused aromatic ring is 2. The ring other than the ring represented by the following formula (AR1) or (AR2) constituting the nitrogen-containing fused aromatic ring is a benzene ring or a pyridine ring. R 1 Indicates ring Ar 1 The substituents present in the cyclic atoms, R 2 Indicates ring Ar 2 The substituents present in the cyclic atoms, v is an integer greater than or equal to 0. The largest number of v is the ring Ar. 1 The maximum number of substituents that a cyclic atom can have. w is an integer greater than or equal to 0. The largest number of w is the ring Ar. 2 The maximum number of substituents that a cyclic atom can have. n is an integer from 0 to 5, and X represents an oxygen atom, a carbonyl group, or an amino group, or a group composed of two of them. [Chemical Formula 3] In the above formula, X 11 Y 11 X 12 and Y 12 Represents a nitrogen atom or a carbon atom. Z 11 Indicates -X 11 -C=CY 11 -Together they form a 6-membered aromatic ring and a group of atoms composed of carbon atoms. Z 12 Indicates -X 12 -C=CY 12 -Together they form a 6-membered aromatic ring and a group of atoms composed of carbon atoms. It is equivalent to the double bond of the cyclopentadiene ring in general formulas (A1) to (A4).

2. The composition according to claim 1, wherein, Component A is a compound represented by the general formula (A1).

3. The composition according to claim 2, wherein, Component A is a compound represented by the following general formula (A11). [Chemical Formula 4] In the above formula, X a and X b This represents a nitrogen atom or CH, where the CH at the # position can be replaced by a nitrogen atom, where X a X b At least one of the CH atoms at the # position is a nitrogen atom. R 11 and R 21 Represents substituents, v1 and w1 are integers from 0 to 4, R 101 and R 102 Indicates a hydrogen atom or a methyl group. L 1 L 2 Sp a and Sp b The meanings are respectively related to L in the general formula (A1) 1 L 2 Sp a and Sp b The meanings are the same.

4. The composition according to claim 1, wherein, Component B is a compound represented by any one of the following general formulas (B11), (B41), or (B51). [Chemical Formula 5] In the above formula, R 201 ~R 204 Represents substituents, where n1 to n4 are integers from 0 to 5, and X 2 Y represents a monovalent substituent. 2 and Y 3 Represents a hydrogen atom or a monovalent substituent, wherein the substituent can act as X. 2 Y 2 Or Y 3 The monovalent substituents used are not aryl or heteroaryl.

5. The composition according to claim 4, wherein, R in the general formula (B11) 201 R 202 X 2 and Y 2 At least one of them, R in the general formula (B41) 201 ~R 203 and Y 3 At least one of them and R in the general formula (B51) 201 ~R 204 At least one of them has a partial structure represented by any one of the following equations (Pol-1) to (Pol-6). [Chemical Formula 6] 。 6. The composition according to claim 4, wherein, Component B is a compound represented by the general formula (B11) or (B41). Wherein, the Y 2 It is a monovalent substituent.

7. The composition according to claim 5, wherein, Component B is a compound represented by the following general formula (B12). [Chemical Formula 7] In the above formula, L a Represents single bonds, -O-, -C(=O)-, -C(=O)O-, alkylene groups, and -CR. β1 =CR β2 - Cycloalkyl or cycloalkylene, wherein the right side of -C(=O)O- is associated with Sp g bonding, R β1 and R β2 Indicates a hydrogen atom or a monovalent substituent. Sp g Indicates a single bond or a divalent linker, Pol 7 It is a group represented by any one of the formulas (Pol-1) to (Pol-6). Among them, in L a In the case of a single key, Sp g It's a single key. R 201 R 202 n1, n2 and Y 2 The meaning of R as described in claim 4 or 5 201 R 202 n1, n2 and Y 2 The meanings are the same.

8. A cured or molded product of the composition according to any one of claims 1 to 7.

9. An optical component comprising the cured material or molded body as described in claim 8.

10. A lens comprising the cured material or molded body as described in claim 8.

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