Compound, polymerizable compound, thermoplastic resin-containing composition and molded body thereof, composition for thermosetting resin and cured product thereof, optical member, and lens

Abstract

The present invention provides: a compound represented by general formula (1); a polymerizable compound; a thermoplastic resin-containing composition containing the compound, and a molded body of the composition; a composition for a thermosetting resin which contains the compound or the polymerizable compound, and a cured product of the composition; and an optical member and a lens each containing the cured product or the molded body. In the formula, R represents a hydrogen atom, an aliphatic hydrocarbon group, or an aromatic hydrocarbon group, two of R1 to R9 each represent a substituent represented by general formula (2), and the remaining seven each represent a hydrogen atom or a monovalent substituent different from the substituent represented by general formula (2). In the formula, L represents an unsubstituted alkylene group having 2-6 carbon atoms, and * indicates a bond.

Description

Compounds, polymerizable compounds, thermoplastic resin-containing compositions and molded articles thereof, thermosetting resin compositions and cured products thereof, optical members, and lenses

[0001] The present invention relates to a compound, a polymerizable compound, a thermoplastic resin-containing composition and a molded article thereof, a thermosetting resin composition and a cured product thereof, an optical member, and a lens.

[0002] Glass materials have traditionally been used for optical components in imaging modules such as cameras, video cameras, camera-equipped mobile phones, videophones, and camera-equipped door phones. Glass materials have been favorably used because they have a variety of optical properties and excellent environmental resistance, but they have drawbacks such as difficulty in reducing their weight and size, and poor processability and productivity. In contrast, cured resins or molded resins can be mass-produced and have excellent processability, and therefore have recently come to be used for various optical components.

[0003] As imaging modules become smaller, the optical components used in the imaging modules also need to be smaller. However, as optical components become smaller, problems with chromatic aberration arise. Therefore, in optical components using cured resins or molded resins, attempts have been made to correct chromatic aberration by adjusting the dispersion characteristics of the refractive index using monomers or additives that constitute the polymers of the cured resins or molded resins.

[0004] For example, compounds and thermoplastic resins containing polycyclic fused rings containing nitrogen atoms as constituent atoms of the fused rings have a low Abbe number (νd) as a wavelength dispersion characteristic of refractive index, or a high partial dispersion ratio (θg, F) ​​as an anomalous partial dispersion. Therefore, they are being developed as materials for use in optical components used in imaging modules. However, as described in Patent Document 1, when using compounds containing polycyclic fused rings containing nitrogen atoms as constituent atoms of the fused rings, it is known that improvement is required in terms of suppressing a decrease in transmittance due to light irradiation (hereinafter also referred to as "light resistance"). Therefore, the development of new compounds with high anomalous partial dispersion of refractive index is desired. Furthermore, compounds used in optical components are sometimes required to suppress a decrease in transmittance due to heat (hereinafter also referred to as "heat resistance"). Meanwhile, coumarin compounds having a 2H-chromen-2-one main skeleton in which the 3-position of the coumarin skeleton is substituted with an aromatic ring group are known. For example, Patent Document 2 describes a compound having two hydroxy groups directly bonded to a 3-arylcoumarin skeleton as a synthetic intermediate for estrogen receptor modulators. Patent Document 3 describes a polymerizable compound having at least two polymerizable groups bonded to the same ring in a 3-arylcoumarin skeleton as a synthetic intermediate for obtaining a reactive mesogen that exhibits a rapid polymerization reaction and can achieve a high pretilt in PSA (polymer maintained alignment) type displays. Patent Document 4 describes a monofunctional polymerizable compound and its oligomer or polymer as a hydrophilic compound containing a photoactive unit, in which two hydroxyalkoxy groups are bonded to a 3-arylcoumarin skeleton and an olefinically unsaturated group such as a (meth)acryloyloxy group is bonded to the alkylene chain constituting one of the hydroxyalkoxy groups.

[0005] International Publication No. 2022 / 255228 International Publication No. 2004 / 091488 JP 2014-509332 A JP 2018-525444 A

[0006] An object of the present invention is to provide a compound that exhibits reduced coloration, high anomalous partial dispersion, and excellent light resistance and heat resistance. Another object of the present invention is to provide a polymerizable compound obtained by deriving this compound. Another object of the present invention is to provide a thermoplastic resin-containing composition containing this compound and a molded article thereof, and a thermosetting resin composition containing this compound or a polymerizable compound and a cured product thereof. Another object of the present invention is to provide an optical element and a lens containing the cured product or molded article.

[0007] That is, the above-mentioned problems of the present invention have been solved by the following means: <1> A compound represented by the following general formula (1): In the above formula, R represents a hydrogen atom, an aliphatic hydrocarbon group, or an aromatic hydrocarbon group. １ ~R ９ Two of the groups represent a substituent represented by the following general formula (2), and the remaining seven groups represent a hydrogen atom or a monovalent substituent different from the substituent represented by the following general formula (2). In the above formula, L represents an unsubstituted alkylene group having 2 to 6 carbon atoms. * represents a bond. <2> The compound according to <1>, which is represented by the following general formula (1-1) or (1-2): In the above formula, R １ ~R ６ , R ８ and R ９ represents a hydrogen atom or a monovalent substituent different from the substituent represented by the general formula (2), and L １ and L ２ represents an unsubstituted alkylene group having 2 to 6 carbon atoms. R has the same meaning as the above R. <3> The compound according to <1> or <2>, wherein the substituent represented by the above general formula (2) is represented by the following general formula (2-1): In the above formula, L Ａrepresents an unsubstituted alkylene group having 1 to 5 carbon atoms. * represents a bond. <4> The compound according to any one of <1> to <3>, wherein the R represents an aliphatic hydrocarbon group. <5> A polymerizable compound obtained by introducing a polymerizable group represented by any one of the following formulas (Pol-1) to (Pol-6) into the compound according to <1> or <2>, using a hydroxy group in the substituent represented by general formula (2) as a reactive group. In the above formula, * represents a bond to L in the above general formula (2). <6> A thermoplastic resin-containing composition containing the compound according to any one of <1> to <4>. However, the compound according to any one of <1> to <4> is not incorporated as a structural unit of a polymer constituting the thermoplastic resin. <7> A thermosetting resin composition containing the compound according to any one of <1> to <4>. <8> A thermosetting resin composition containing the polymerizable compound according to <5>. <9> A molded product of the thermoplastic resin-containing composition according to <6>. <10> A cured product obtained from the thermosetting resin composition according to <7>. <11> A cured product obtained from the thermosetting resin composition according to <8>. <12> An optical element containing the molded product according to <9> or the cured product according to <10> or <11>. <13> A lens containing the molded product according to <9> or the cured product according to <10> or <11>.

[0008] In the present invention, when there are multiple substituents or linking groups, etc., represented by a specific symbol or formula (hereinafter referred to as substituents, etc.), or when multiple substituents, etc. are specified simultaneously, unless otherwise specified, the respective substituents, etc. may be the same or different from each other (regardless of the presence or absence of the expression "independently," the respective substituents, etc. may be the same or different from each other). This also applies to the specification of the number of substituents, etc. Furthermore, when multiple substituents, etc., are adjacent to each other (especially when they are adjacent), they may be linked to each other to form a ring, unless otherwise specified. Furthermore, unless otherwise specified, rings, such as alicyclic rings, aromatic rings, and heterocyclic rings, may be further condensed to form a fused ring. In the present invention, unless otherwise specified, with respect to double bonds, when E- and Z-configurations exist in a molecule, they may be either one of them, or a mixture thereof. Furthermore, in the present invention, unless otherwise specified, when a compound has one or more asymmetric carbons, the stereochemistry of such asymmetric carbons can each independently be either an (R) or (S) configuration. As a result, the compound may be a mixture of stereoisomers such as optical isomers or diastereoisomers, or may be a racemate. In the present invention, unless otherwise specified, when a compound has a repeating structure, the repeating number of the repeating structure may be the same for all repeating structures, or may be a mixture of compounds with different repeating numbers. Furthermore, in the present invention, the description of a compound includes compounds in which a portion of the structure has been modified, as long as the effects of the present invention are not impaired. Furthermore, for compounds that are not specified as substituted or unsubstituted, it means that the compound may have any substituent, as long as the effects of the present invention are not impaired. Examples of optional substituents that the compound may have include alkyl groups, alkoxy groups, fluoro groups, chloro groups, and cyano groups. Here, the alkyl groups and alkoxy groups may have a substituent, and preferred examples of optional substituents include fluoro groups and chloro groups. In the present invention, for substituents (the same applies to linking groups and rings) that are not specified as substituted or unsubstituted, it means that the group may have any substituent, as long as the desired effects are not impaired.For example, the term "alkyl group" means both an unsubstituted alkyl group and a substituted alkyl group. In the present invention, when the number of carbon atoms of a certain group is specified, this number of carbon atoms means the number of carbon atoms of the entire group unless otherwise specified in the present invention or this specification. In other words, when this group further has a substituent, it means the total number of carbon atoms including the substituent.

[0009] In the present invention, a numerical range expressed using "to" means a range that includes the numerical values ​​before and after "to" as the lower and upper limits. In the thermosetting resin composition of the present invention or the thermoplastic resin-containing composition of the present invention (hereinafter, these are also collectively referred to as "the composition of the present invention"), each component (the compound of the present invention or the polymerizable compound of the present invention, and other components that may be contained as appropriate) may be used alone or in combination of two or more. This also applies to each component in a cured product or molded article obtained from the composition of the present invention, as well as each component in an optical member and a lens. Note that in a cured product, optical member, or lens obtained using a thermosetting resin composition containing the polymerizable compound of the present invention as a raw material monomer for the resin, the structure derived from the polymerizable compound of the present invention in the resin may be one type of structure or two or more types of structures depending on the type of polymerizable compound of the present invention used as a monomer. In describing the content of each component in the composition of the present invention, the solid content in the composition of the present invention refers to the components that remain in the cured product or molded article obtained from the composition of the present invention, in addition to the compound of the present invention or the polymerizable compound of the present invention. Typically, the remainder after removing the solvent is the "solids content."

[0010] In the present invention, "(meth)acrylate" refers to either or both of acrylate and methacrylate, and "(meth)acryloyl" refers to either or both of acryloyl and methacryloyl. The term "monomer" in the present invention is distinguished from oligomers and polymers and refers to a compound having a mass average molecular weight of 1,000 or less.

[0011] In the present invention, the term "aliphatic hydrocarbon group" refers to a chain aliphatic hydrocarbon group or an alicyclic hydrocarbon group. The chain aliphatic hydrocarbon group refers to an alkyl group obtained by removing one arbitrary hydrogen atom from a linear or branched alkane, an alkenyl group obtained by removing one arbitrary hydrogen atom from a linear or branched alkene, or an alkynyl group obtained by removing one arbitrary hydrogen atom from a linear or branched alkyne. In the present invention, the chain aliphatic hydrocarbon group is preferably an alkyl group obtained by removing one arbitrary hydrogen atom from a linear or branched alkane. Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a 1-methylbutyl group, a 3-methylbutyl group, a hexyl group, a 1-methylpentyl group, a 4-methylpentyl group, a heptyl group, a 1-methylhexyl group, a 5-methylhexyl group, a 2-ethylhexyl group, an octyl group, a 1-methylheptyl group, a nonyl group, a 1-methyloctyl group, a decyl group, an undecyl group, a dodecyl group, a tridecyl group, a tetradecyl group, a pentadecyl group, a hexadecyl group, a heptadecyl group, an octadecyl group, a nonadecyl group, and an eicosyl group. In the present invention, the aliphatic hydrocarbon group (unsubstituted) is preferably an alkyl group having 1 to 10 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms, still more preferably an alkyl group having 1 to 4 carbon atoms, particularly preferably a methyl group or an ethyl group, and most preferably a methyl group.

[0012] In the present invention, the term "alkyl group" refers to a linear or branched alkyl group. Examples of the alkyl group include those listed above. Similarly, the alkyl group in a group containing an alkyl group (such as an alkoxy group) also refers to a linear or branched alkyl group, and examples of the alkyl group include those listed above. Furthermore, in the present invention, examples of the alkylene group include groups obtained by removing any one hydrogen atom from the above alkyl groups, and may be either linear or branched.

[0013] The compound of the present invention exhibits reduced coloration, high anomalous partial dispersion, and excellent light resistance and heat resistance. Furthermore, a polymerizable compound obtained by deriving the compound of the present invention, a thermoplastic resin-containing composition containing the compound of the present invention and a molded article thereof, a thermosetting resin composition containing the compound of the present invention or the polymerizable compound of the present invention and a cured product thereof, and an optical member and a lens containing the cured product or molded article can exhibit reduced coloration, high anomalous partial dispersion, and excellent light resistance and heat resistance.

[0014] The compound of the present invention is a compound represented by the general formula (1) shown below, which exhibits reduced coloration, high anomalous partial dispersion, and excellent light resistance and heat resistance. That is, the compound of the present invention has a R １ ~R ９In other words, it has a structure having two hydroxy groups via a specific linking group represented by -OL- (L represents an unsubstituted alkylene group having 2 to 6 carbon atoms). Generally, as the conjugation length increases, the absorption wavelength shifts to the longer wavelength side, increasing anomalous partial dispersibility, but also causing coloration. In the present invention, however, by adjusting the conjugation length by introducing a phenyl group into the 3-position of the coumarin skeleton, it is possible to increase anomalous partial dispersibility with almost no coloration. Furthermore, as described in Macromolecules, 2013, Vol. 46, No. 13, p. In contrast to compounds having a coumarin skeleton with an unsubstituted 3-position, such as those described in US Pat. No. 5,133-, 5,140, ​​which undergo photodimerization and have poor light resistance, the steric effect of the phenyl group at the 3-position suppresses intermolecular photodimerization and thermal decomposition, and the inclusion of a hydroxy group on the 3-phenylcoumarin skeleton via a specific linking group represented by -O-L- (where L is an unsubstituted alkylene group having 2 to 6 carbon atoms) results in increased thermal stability, reduced coloration, high anomalous partial dispersion, and excellent light resistance and heat resistance compared to compounds in which L is a substituted alkylene group having 2 to 6 carbon atoms. Therefore, the compound of the present invention can be suitably used as an additive for resins for optical materials requiring optical transparency, anomalous partial dispersion, light resistance, and heat resistance, or as a raw material monomer for resins. Furthermore, since the compound of the present invention has two substituents represented by general formula (2), it can be used as a bifunctional monomer or a precursor thereof.

[0015] The present invention will be described in detail below. The following description of the components may be based on representative embodiments or specific examples, but the present invention is not limited to such embodiments.

[0016] [Compound] The compound represented by the general formula (1) of the present invention is as follows.

[0017]

[0018] In the above formula, R represents a hydrogen atom, an aliphatic hydrocarbon group, or an aromatic hydrocarbon group. １ ~R ９Two of these represent a substituent represented by the general formula (2) described below, and the remaining seven represent a hydrogen atom or a monovalent substituent different from the substituent represented by the general formula (2) described below.

[0019] The substituents in the general formula (1) will be described in detail below.

[0020] (1) R R represents a hydrogen atom, an aliphatic hydrocarbon group, or an aromatic hydrocarbon group. The aliphatic hydrocarbon group that can be taken as R is preferably a chain aliphatic hydrocarbon group, more preferably an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, or an alkynyl group having 2 to 10 carbon atoms, even more preferably an alkyl group having 1 to 10 carbon atoms, and particularly preferably an alkyl group having 1 to 4 carbon atoms, of which a methyl group or an ethyl group is preferred, and a methyl group is most preferred. The aromatic hydrocarbon group that can be taken as R preferably has 6 to 20 carbon atoms, more preferably 6 to 16 carbon atoms, even more preferably 6 to 12 carbon atoms, and particularly preferably 6 to 8 carbon atoms, and of which a phenyl group is preferred. The aliphatic hydrocarbon group and aromatic hydrocarbon group that can be taken as R can employ any substituent within the range that does not impair the effects of the present invention. Examples include an alkoxy group, an acyl group, a fluoro group, a chloro group, and a bromo group. R is preferably a hydrogen atom or an aliphatic hydrocarbon group, and from the viewpoint of further suppressing coloration, an aliphatic hydrocarbon group is more preferable, and among these, a methyl group is preferable.

[0021] (2) R １ ~R ９ R １ ~R ９ Two of the groups represent a substituent represented by the following general formula (2), and the remaining seven groups represent a hydrogen atom or a monovalent substituent different from the substituent represented by the following general formula (2).

[0022]

[0023] In the above formula, L represents an unsubstituted alkylene group having 2 to 6 carbon atoms. * represents a bond.

[0024] The unsubstituted alkylene group having 2 to 6 carbon atoms represented by L may be either a linear alkylene group or a branched alkylene group. Examples of L include ethylene, 1,2-propylene, 1,3-propylene, 1,2-butylene, 1,3-butylene, 1,4-butylene, 1,2-pentylene, 1,3-pentylene, 1,4-pentylene, 1,5-pentylene, 1,2-hexylene, 1,3-hexylene, 1,4-hexylene, 1,5-hexylene, and 1,6-hexylene. L is preferably an unsubstituted alkylene group having 2 to 4 carbon atoms, more preferably an unsubstituted ethylene group.

[0025] The substituent represented by the above general formula (2) is preferably a substituent represented by the following general formula (2-1), from the viewpoint of further suppressing coloration when the polymerizable compound of the present invention described below is derived.

[0026]

[0027] In the above formula, L Ａ represents an unsubstituted alkylene group having 1 to 5 carbon atoms. * represents a bond.

[0028] L Ａ The unsubstituted alkylene group having 1 to 5 carbon atoms as L may be either a linear alkylene group or a branched alkylene group. Ａ Examples of L include an unsubstituted methylene group, as well as those having 2 to 5 carbon atoms among the specific examples of the unsubstituted alkylene groups having 2 to 6 carbon atoms as L. Ａ is preferably an unsubstituted alkylene group having 1 to 3 carbon atoms, more preferably an unsubstituted methylene group.

[0029] R １ ~R ９ Among these, seven other than the substituent represented by the general formula (2) (in the present invention, they may also be simply referred to as "the remaining seven") represent a hydrogen atom or a monovalent substituent different from the substituent represented by the general formula (2). １ ~R ９The remaining seven monovalent substituents different from the substituent represented by the general formula (2) may be any substituent within the scope of the present invention, as long as the effects of the present invention are not impaired. Examples of such substituents include an alkyl group, an alkoxy group, a fluoro group, a chloro group, and a bromo group. １ ~R ９ Among the remaining seven groups, the number of groups that are monovalent substituents different from the substituent represented by the general formula (2) is preferably 4 or less, more preferably 2 or less, and even more preferably 1 or less. １ ~R ９ It is also preferred that all of the remaining seven are hydrogen atoms.

[0030] The compound represented by the general formula (1) above preferably has no hydroxy group other than the substituent represented by the general formula (2), that is, it is preferably a bifunctional compound (bis(hydroxyalkoxy) compound) having a 3-phenylcoumarin skeleton. The compound represented by the general formula (1) above preferably has a substituent represented by the general formula (2) as R １ ~R ４ One of them and R ５ ~R ９It is preferable that the compound has one of the following. In this case, the polarizability in the direction along the axis connecting the hydroxy groups of the two substituents represented by the general formula (2) is increased, and in a polymer obtained by using the compound represented by the general formula (1) as a monomer, the structural unit derived from the compound represented by the general formula (1) (the structural unit obtained by removing a hydrogen atom from the hydroxy group in the substituent represented by the general formula (2) in the compound represented by the general formula (1)) is oriented in the direction of the polymer main chain, thereby improving the positive birefringence characteristics (Δn properties). In optical thermoplastic polymers (e.g., polycarbonates) used in retardation films and the like, a method of controlling birefringence by copolymerizing a monomer having negative birefringence characteristics (e.g., a diol monomer) with a monomer having positive birefringence characteristics (e.g., a diol monomer) is known, as described in Japanese Patent No. 5079150. Monomers having negative birefringence include diol monomers such as biscresol fluorene and 9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene, and as diol monomers having positive birefringence to be combined with these, it is preferable to use monomers having increased polarizability in the direction along the main chain of the structural unit, from the viewpoint of reducing the birefringence of the thermoplastic polymer at a lower copolymerization ratio. As such monomers having positive birefringence, among the compounds represented by the general formula (1) above, those in which the substituent represented by the general formula (2) is replaced by R １ ~R ４ One of them and R ５ ~R ９ A compound having one of the following properties can be preferably applied.

[0031] The compound represented by the general formula (1) is preferably a compound represented by any one of the following general formulas (1-1) to (1-6), and from the viewpoint of further improving all of the light transmittance, anomalous partial dispersion, light fastness, and heat resistance, it is more preferably a compound represented by the following general formula (1-1) or (1-2), and even more preferably a compound represented by the following general formula (1-1).

[0032]

[0033] In the above formula, R １ ~R ９ represents a hydrogen atom or a monovalent substituent different from the substituent represented by the general formula (2), and L １ and L ２ represents an unsubstituted alkylene group having 2 to 6 carbon atoms. R has the same meaning as R in the above general formula (1).

[0034] R １ ~R ９ The monovalent substituent different from the substituent represented by the general formula (2) that can be adopted by R １ ~R ９ The remaining seven are synonymous with the monovalent substituents different from the substituent represented by the general formula (2). １ ~R ９ is preferably a hydrogen atom.

[0035] L １ and L ２ The unsubstituted alkylene group having 2 to 6 carbon atoms as L has the same meaning as the unsubstituted alkylene group having 2 to 6 carbon atoms as L in the above general formula (2). １ and L ２ is preferably an unsubstituted alkylene group having 2 to 4 carbon atoms, more preferably an unsubstituted ethylene group.

[0036] The compounds represented by any of the above general formulas (1-1) to (1-6) are preferably compounds represented by any of the following general formulas (1-1A) to (1-6A), respectively. Among these compounds represented by any of the general formulas (1-1A) to (1-6A), from the viewpoint of further improving all of the light transmittance, anomalous partial dispersion, light fastness, and heat resistance, compounds represented by the following general formula (1-1A) or (1-2A) are more preferred, and compounds represented by the following general formula (1-1A) are even more preferred.

[0037]

[0038] In the above formula, R represents a hydrogen atom or an aliphatic hydrocarbon group, and R １ ~R ９ represents a hydrogen atom or a monovalent substituent different from the substituent represented by the general formula (2). Ａ１ and LＡ２ represents an unsubstituted alkylene group having 1 to 5 carbon atoms.

[0039] R １ ~R ９ The monovalent substituent different from the substituent represented by the general formula (2) can be １ ~R ９ The remaining seven are synonymous with the monovalent substituents different from the substituent represented by the general formula (2). １ ~R ９ is preferably a hydrogen atom.

[0040] The aliphatic hydrocarbon group that can be taken as R has the same meaning as the aliphatic hydrocarbon group that can be taken as R in the above general formula (1). From the viewpoint of further suppressing coloration, R is more preferably an aliphatic hydrocarbon group, and among these, a methyl group is preferable.

[0041] Specific examples of the compound represented by general formula (1) of the present invention are listed below, but are not limited to these. In the following table, Me represents a methyl group, Et represents an ethyl group, isoPr represents an isopropyl group, n-Pr represents an n-propyl group, OMe represents a methoxy group, Ph represents a phenyl group, H represents a hydrogen atom, F represents a fluoro group, Cl represents a chloro group, Br represents a bromo group, CH2 represents a methylene group, C2H4 represents an ethylene group, C3H6 represents a 1,3-propylene group, C4H8 represents a 1,4-butylene group, and C5H10 represents a 1,5-pentylene group. In the following table, LA1, LA2, and R1 to R9 represent the L groups in the skeleton, respectively. Ａ１ , L Ａ２ and R １ ~R ９ "-" indicates that the corresponding group does not exist.

[0042]

[0043]

[0044]

[0045]

[0046]

[0047]

[0048]

[0049]

[0050]

[0051]

[0052]

[0053]

[0054] In the above skeletons B and D, R in general formula (1) is described as a hydrogen atom.

[0055]

[0056] The molecular weight of the compound of the present invention is not particularly limited, but is preferably, for example, 700 or less.

[0057] The compound represented by general formula (1), i.e., a compound having a 3-phenylcoumarin skeleton, can be synthesized, for example, as shown below, by the Perkin reaction of condensing a 2-hydroxybenzaldehyde compound or a 2-hydroxyphenyl ketone compound (compound (A) shown below) with an α-arylacetic acid compound (compound (B) shown below). For example, the synthesis method described in Asian J. Chem., 2020, volume 32, pp. 2397-2402 can be used as reference.

[0058]

[0059] In the above scheme, R and R １ ~R ９ represents R and R in the general formula (1). １ ~R ９ That is, the compound represented by the general formula (1) is a compound represented by the general formula (1) in which R １ ~R ９The compound (A) can be synthesized by using a compound (raw material) in which two of R have the substituents represented by the above-mentioned general formula (2). When R is a hydrogen atom, the compound (A) becomes a 2-hydroxybenzaldehyde compound, and when R is an aliphatic hydrocarbon group (preferably an alkyl group) or an aromatic hydrocarbon group, the compound (A) becomes a 2-hydroxyphenyl ketone compound. In the above scheme, when R in compounds (A) and (B) １ ~R ９ A precursor compound having a 3-phenylcoumarin skeleton may be synthesized using a compound (raw material) having groups that are precursors of the substituent represented by the aforementioned general formula (2), and then subsequent reactions such as a deprotection reaction and an etherification reaction may be carried out to convert the precursor group of the substituent represented by the general formula (2) into the substituent represented by the general formula (2), thereby synthesizing a compound represented by the general formula (1). For example, an example of a group that is a precursor of the substituent represented by the general formula (2) is a hydroxy group, and a method of converting the hydroxy group into a substituent represented by the general formula (2), such as a 2-hydroxyethyloxy group, by carrying out an etherification reaction using an alkylene carbonate such as ethylene carbonate may be mentioned. The compound represented by the general formula (1) can be produced according to standard methods as described above, with reference to the methods described in the Examples below.

[0060] The Abbe number (νd) and partial dispersion ratio (θg, F) ​​of the compound of the present invention are values ​​measured using an ellipsometer (for example, J.A. Woollam Co., Ltd., trade name: M-2000XI-210). Specifically, based on the description in the evaluation of anomalous partial dispersion in the Examples described below, the refractive index of the compound of the present invention is measured and calculated as an extrapolated value for resin films prepared by changing the content concentration of the compound of the present invention. The Abbe number (νd) and partial dispersion ratio (θg, F) ​​of the compound are calculated by the following formula. In addition, JIS B 7090:1999 Optics and optical instruments - Reference wavelengths (ISO 7944:1998 Optics and optical instruments - Reference wavelengths) can be appropriately referenced. νd=(nd-1) / (nF-nC) θg,F=(ng-nF) / (nF-nC) 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. nF, nC, and ng are all refractive indices (extrapolated values) at the point where the blending ratio of the above compounds is 100%.

[0061] In a graph of Abbe number (νd) on the horizontal axis versus partial dispersion ratio (θg,F) on the vertical axis, the compound of the present invention has a large deviation Δ(θg,F) (i.e., distance from the standard line) of the partial dispersion ratio (θg,F) from a standard line obtained by connecting glass type NSL7 (refractive index at the d-line: 1.51, Abbe number (νd): 60.5, partial dispersion ratio (θg,F): 0.54) which is a standard for normal glass, and glass type PBM2 (refractive index at the d-line: 1.62, Abbe number (νd): 36.3, partial dispersion ratio (θg,F): 0.58), and is located above the standard line, and therefore has a large positive anomalous partial dispersion. The deviation Δ(θg,F) of the partial dispersion ratio (θg,F) of the compound of the present invention is preferably 0.04 or more, more preferably 0.08 or more, even more preferably 0.16 or more, and particularly preferably 0.20 or more. The upper limit of the deviation Δ(θg,F) of the partial dispersion ratio (θg,F) of the compound of the present invention is not particularly limited, but is usually 0.50 or less.

[0062] The Abbe number (νd) of the compound of the present invention is not particularly limited, but is preferably 35 or less, more preferably 30 or less, even more preferably 29 or less, and particularly preferably 28 or less. In addition, the Abbe number (νd) of the compound of the present invention is not particularly limited, but is preferably 1 or more, more preferably 3 or more, even more preferably 5 or more, and particularly preferably 7 or more.

[0063] The partial dispersion ratio (θg, F) ​​of the compound of the present invention is not particularly limited, but is preferably 0.75 or more, more preferably 0.80 or more. The partial dispersion ratio (θg, F) ​​of the compound of the present invention is not particularly limited, but is preferably 2.0 or less, more preferably 1.8 or less, and even more preferably 1.7 or less.

[0064] The compound of the present invention exhibits reduced coloration and excellent light transmittance in the visible light region. The compound of the present invention exhibits substantially no absorption in the long wavelength region of the visible light region, and exhibits a decrease in transmittance toward the shorter wavelength side. Therefore, the transparency of the compound of the present invention can be evaluated by measuring the transmittance at a wavelength of 430 nm. The transmittance of the compound of the present invention at a wavelength of 430 nm is a value measured using an ultraviolet-visible spectrophotometer (e.g., UV-2600 (trade name, manufactured by Shimadzu Corporation)). Specifically, the transmittance at a wavelength of 430 nm is measured, for example, for a THF (tetrahydrofuran) solution in the same manner as in the transmittance measurement described in the Examples below. Furthermore, a light irradiation test for evaluating the light resistance of the compound is performed based on the xenon light irradiation test described in the Examples below, and a heating test for evaluating the heat resistance of the compound is performed based on the heating test described in the Examples below.

[0065] Hereinafter, preferred values ​​for the transmittance at a wavelength of 430 nm of the compound of the present invention measured by the above method will be described. The transmittance of the compound of the present invention, i.e., the transmittance before the light irradiation test, is not particularly limited, but is preferably 94% or more, more preferably 96% or more, and even more preferably 98% or more. Furthermore, the transmittance of the compound of the present invention after the light irradiation test is not particularly limited, but in Evaluation Item 3 (transmittance after 24-hour xenon light irradiation test) described below, it is preferably more than 86%, more preferably more than 89%, and even more preferably more than 93%. The decrease in transmittance of the compound of the present invention before and after the light irradiation test is not particularly limited, but in Evaluation Item 3 (transmittance decrease before and after 24-hour xenon light irradiation test) described below, it is preferably less than 8%, more preferably less than 5%. 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. Furthermore, the transmittance of the compound of the present invention after the heating test is not particularly limited, but in evaluation item 4 described below (transmittance after a heating test at 230°C for 30 minutes), it is preferably more than 86%, more preferably more than 89%, and even more preferably more than 93%. The decrease in transmittance of the compound of the present invention before and after the heating test is not particularly limited, but in evaluation item 4 described below (transmittance decrease before and after a heating test at 230°C for 30 minutes), it is preferably less than 8%, more preferably less than 5%. The decrease in transmittance before and after the heating test is calculated by subtracting the transmittance value after the heating test from the transmittance value before the heating test.

[0066] [Polymerizable Compound] The polymerizable compound of the present invention is a compound obtained by introducing a polymerizable group represented by any one of the following formulae (Pol-1) to (Pol-6) into the compound of the present invention, using the hydroxy group in the substituent represented by the above-mentioned general formula (2) as a reactive group. When the substituent represented by the above-mentioned general formula (2) is a substituent represented by the above-mentioned general formula (2-1), "the hydroxy group in the general formula (2)" is read as "the hydroxy group in the general formula (2-1)", and "L in the general formula (2)" is read as "L in the general formula (2-1)". Ａ -CH ２ " and the above description shall apply. The same applies hereinafter. The polymerizable compound of the present invention is a bifunctional polymerizable compound having two polymerizable groups represented by any one of the following formulae (Pol-1) to (Pol-6) in the compound.

[0067]

[0068] In the above formula, * indicates a bond to L in the above general formula (2).

[0069] The polymerizable group represented by the above formula (Pol-1) or (Pol-2) can be introduced by an ester synthesis reaction, and the polymerizable group represented by any of the above formulas (Pol-3) to (Pol-6) can be introduced by an ether synthesis reaction. For the ester synthesis reaction and the ether synthesis reaction, reactions that are commonly used can be adopted, and the reaction conditions can also be appropriately adjusted.

[0070] The polymerizable compound of the present invention is preferably a compound obtained by introducing a polymerizable group represented by any one of the above formulas (Pol-1) to (Pol-4) into the compound of the present invention, using the hydroxy group in the substituent represented by the above general formula (2) as a reactive group, and more preferably a compound obtained by introducing a polymerizable group represented by the above formula (Pol-1) or (Pol-2). Note that the two polymerizable groups represented by any one of the above formulas (Pol-1) to (Pol-6) possessed by the polymerizable compound of the present invention may be the same or different.

[0071] Specific examples of the polymerizable compound of the present invention include, but are not limited to, compounds in which the hydroxy group in the substituent represented by general formula (2) in the above-mentioned specific examples of the compound represented by general formula (1) of the present invention is replaced with a polymerizable group represented by any of the above formulas (Pol-1) to (Pol-6).

[0072] The polymerizable compound of the present invention has the same structure as the compound of the present invention, except that the hydroxy group in the substituent represented by the aforementioned general formula (2) is converted to a polymerizable group represented by any of the above formulae (Pol-1) to (Pol-6). Therefore, like the compound of the present invention, the polymerizable compound of the present invention exhibits reduced coloration, high anomalous partial dispersion, and excellent light resistance and heat resistance. The above descriptions relating to the compound of the present invention can be used to refer to the deviation Δ(θg,F) of the partial dispersion ratio (θg,F), the Abbe number (νd), the partial dispersion ratio (θg,F), the transmittance at a wavelength of 430 nm, the transmittance after a light irradiation test, and the decrease in transmittance before and after a light irradiation test of the polymerizable compound of the present invention.

[0073] [Composition] The composition of the present invention is a composition containing the compound of the present invention or the polymerizable compound of the present invention, and preferred examples thereof include a composition for a thermosetting resin and a composition containing a thermoplastic resin.

[0074] <Composition for Thermosetting Resin> In the present invention, the term "composition for thermosetting resin" refers to a composition containing the compound of the present invention or the polymerizable compound of the present invention and used to obtain a thermosetting resin. Among the compositions for thermosetting resin of the present invention, those containing the compound of the present invention contain the compound of the present invention as a resin additive and contain a raw material monomer for the thermosetting resin separately from the compound of the present invention. Therefore, the compound of the present invention is present as a resin additive in the thermosetting resin obtained by curing the composition for thermosetting resin of the present invention. Meanwhile, among the compositions for thermosetting resin of the present invention, those containing the polymerizable compound of the present invention contain the polymerizable compound of the present invention as a component constituting the thermosetting resin, i.e., as a raw material monomer for the thermosetting resin. Therefore, the polymerizable compound of the present invention is incorporated as a structural unit of the polymer constituting the thermosetting resin in the thermosetting resin obtained by curing the composition for thermosetting resin of the present invention.

[0075] In the thermosetting resin composition of the present invention, when the compound of the present invention is contained as a resin additive, the composition may further contain additives other than the compound of the present invention. Furthermore, as the raw material monomer for the thermosetting resin, raw material monomers that can constitute thermosetting resins used in optical applications can be used without particular limitation, as long as the effects of the present invention are not impaired. For example, in addition to the (meth)acrylate monomers described below, vinyl monomers, epoxy monomers, and oxetanyl monomers commonly used in optical applications are preferred. In the thermosetting resin composition of the present invention, when the polymerizable compound of the present invention is contained as a raw material monomer for the thermosetting resin, the composition may further contain raw material monomers for the thermosetting resin other than the polymerizable compound of the present invention, and these can be used without particular limitation, as long as the effects of the present invention are not impaired. For example, the (meth)acrylate monomers described below, vinyl monomers, epoxy monomers, and oxetanyl monomers commonly used in optical applications are preferred. In addition, additives used in optical applications can also be contained without particular limitation, as long as the effects of the present invention are not impaired. The additives that may be contained in the thermosetting resin composition of the present invention are the same as those described below for other components. The thermosetting resin composition of the present invention may also be in a form containing both the compound of the present invention and the polymerizable compound of the present invention. The functions of the compound of the present invention and the polymerizable compound of the present invention in this form are as described above.

[0076] <Thermoplastic Resin-Containing Composition> In the present invention, the thermoplastic resin-containing composition refers to a composition containing the compound of the present invention and a thermoplastic resin. However, when the composition of the present invention is a thermoplastic resin-containing composition, the compound of the present invention is not incorporated as a structural unit of the polymer constituting the thermoplastic resin contained in the thermoplastic resin-containing composition of the present invention. In other words, in the thermoplastic resin-containing composition of the present invention, the compound of the present invention is contained as an additive for the resin.

[0077] The thermoplastic resin-containing composition of the present invention may further contain additives other than the compound of the present invention. Furthermore, as the thermoplastic resin, any thermoplastic resin used for optical applications can be used without particular limitation as long as it does not impair the effects of the present invention. Examples of preferred thermoplastic resins include polycarbonate, polyester, (meth)acrylate polymer, and cyclic olefin (co)polymer. The description of other components described below applies to additives that may be contained in the thermoplastic resin-containing composition of the present invention.

[0078] When the compound of the present invention is contained as a resin additive in the thermosetting resin composition or thermoplastic resin-containing composition of the present invention (when contained as a non-monomer component in the thermosetting resin composition), the content of the compound of the present invention in the thermosetting resin composition or thermoplastic resin-containing composition of the present invention is, for example, preferably 1 to 50 mass%, more preferably 3 to 45 mass%, and even more preferably 5 to 40 mass%, of the total solids content of the composition. Note that when two or more types of compounds of the present invention are contained in the thermosetting resin composition or thermoplastic resin-containing composition of the present invention, the total content thereof is preferably within the above range.

[0079] Furthermore, when the polymerizable compound of the present invention is contained in the composition for a thermosetting resin of the present invention as a raw material monomer for the thermosetting resin, the content of the polymerizable compound of the present invention in the composition for a thermosetting resin of the present invention is, for example, preferably 15 to 99 mass %, more preferably 25 to 99 mass %, and even more preferably 35 to 97 mass %, based on the total solid content of the composition. Note that when two or more types of polymerizable compounds of the present invention are contained in the composition for a thermosetting resin of the present invention, the total content thereof is preferably within the above range.

[0080] By setting the content of the compound of the present invention in the composition for thermosetting resins or the composition containing thermoplastic resins of the present invention, and the content of the polymerizable compound of the present invention in the composition for thermosetting resins of the present invention within the above-mentioned ranges, it becomes possible to realize at a higher level the effects of the present invention, such as suppressing coloration, achieving high anomalous partial dispersibility (i.e., achieving a partial dispersion ratio (θg,F) higher than the predicted partial dispersion ratio (θg,F) in a cured product having a predetermined Abbe number (νd)), and also achieving excellent light resistance and heat resistance.

[0081] <Other Components> The composition of the present invention may further contain other components in addition to the compound of the present invention or the polymerizable compound of the present invention. Examples of other components include (meth)acrylate monomers, polymers having a radically polymerizable group in a side chain, and polymerization initiators. The composition may also contain polymers or monomers other than the above-mentioned components, dispersants, plasticizers, heat stabilizers, mold release agents, solvents, etc. As the heat stabilizer, for example, a hindered phenol-based heat stabilizer or a phosphorus-based heat stabilizer described in paragraphs

[0261] and

[0262] of JP 2021-1328 A can be used. As the polymer having a radically polymerizable group in a side chain, for example, a polymer having a radically polymerizable group in a side chain described in paragraphs

[0198] and

[0205] of WO 2022 / 255228 can be used. Note that, since the thermoplastic resin-containing composition of the present invention does not require a further polymerization (curing) reaction, it is preferable that the composition does not contain a polymer or monomer having a polymerizable group or a polymerization initiator.

[0082] ((Meth)acrylate Monomer) The thermosetting resin 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. Specific examples of the (meth)acrylate monomer include Monomers 1 to 6 and M-1 to M-10 shown below. In Monomer 5 shown below, n represents the number of repetitions. Other examples include the (meth)acrylate monomers described in paragraphs 0037 to 0046 of JP 2012-107191 A. The molecular weight of the (meth)acrylate monomer is preferably 100 to 500.

[0083]

[0084]

[0085] There are no particular limitations on how the (meth)acrylate monomer can be obtained, and it may be commercially available or synthesized by a conventional method. When commercially available, for example, Viscoat #192 PEA (monomer 1) (manufactured by Osaka Organic Chemical Industry Co., Ltd.), Viscoat #160 BZA (monomer 2) (manufactured by Osaka Organic Chemical Industry Co., Ltd.), Light Ester Bz (monomer 2) (manufactured by Kyoeisha Chemical Co., Ltd.), A-DCP (monomer 3) (manufactured by Shin-Nakamura Chemical Co., Ltd.), FA-513AS (monomer 4) (manufactured by Hitachi Chemical Co., Ltd.), Oxol EA-0200 (monomer 6) (manufactured by Osaka Gas Chemicals 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 Shin-Nakamura Chemical Co., Ltd.), Preferably usable examples include: Light Ester IB-X (M-4 above) (manufactured by Kyoeisha Chemical Co., Ltd.), FA-513M (M-5 above) (manufactured by Hitachi Chemical Co., Ltd.), Light Ester L (M-6 above) (manufactured by Kyoeisha Chemical Co., Ltd.), 2EHA (M-7 above) (manufactured by Toagosei Co., Ltd.), HEA (M-8 above) (manufactured by Osaka Organic Chemical Industry Co., Ltd.), Light Ester HOP-A(N) (M-9 above) (manufactured by Kyoeisha Chemical Co., Ltd.), and 4-HBA (M-10 above) (manufactured by Osaka Organic Chemical Industry Co., Ltd.).

[0086] When the composition for a thermosetting resin of the present invention contains a (meth)acrylate monomer, the content of the (meth)acrylate monomer in the composition for a thermosetting resin of the present invention is preferably 1 to 85 mass%, more preferably 1 to 75 mass%, and even more preferably 3 to 65 mass%. By adjusting the amount of the (meth)acrylate monomer in the composition for a thermosetting resin of the present invention, it is possible to adjust the function of alleviating stress when the cured product undergoes thermal changes.

[0087] (Polymerization Initiator) The thermosetting resin composition of the present invention preferably contains a polymerization initiator, such as a thermal radical polymerization initiator, a photoradical polymerization initiator, and a photocationic polymerization initiator. The thermosetting resin composition of the present invention can be used to obtain a cured thermosetting resin that does not soften or melt, unlike thermoplastic resins, even when reheated after curing. The method for obtaining the thermosetting resin is not limited, as long as it can produce a cured thermosetting resin that does not soften or melt, as thermoplastic resins do, even when reheated. This method may involve curing the thermosetting resin composition of the present invention by thermal polymerization, photopolymerization by ultraviolet irradiation, or curing without heat using a curing accelerator, or a combination of these methods. Therefore, the thermosetting resin composition of the present invention can contain a polymerization initiator in accordance with the method for obtaining the thermosetting resin. It is more preferable that the thermosetting resin composition of the present invention contains at least one of a thermal radical polymerization initiator and a photoradical polymerization initiator.

[0088] (Thermal radical polymerization initiator) The thermosetting resin composition of the present invention preferably contains a thermal radical polymerization initiator. By thermally polymerizing (curing) the thermosetting resin composition of the present invention due to the action of this thermal radical polymerization initiator, it is possible to obtain a cured product that is suppressed in coloration, has high anomalous partial dispersion, and exhibits excellent light resistance and heat resistance.

[0089] As the thermal radical polymerization initiator, compounds commonly used as thermal radical polymerization initiators can be used as appropriate depending on the conditions of the thermal polymerization (thermal curing) step described below. For example, organic peroxides can be used, and specifically, the following compounds can be used: Examples of peroxyl groups include 1,1-di(t-hexylperoxy)cyclohexane, 1,1-di(t-butylperoxy)cyclohexane, 2,2-di(4,4-di-(t-butylperoxy)cyclohexyl)propane, t-hexylperoxyisopropyl monocarbonate, t-butylperoxy-3,5,5-trimethylhexanoate, t-butylperoxylaurate, dicumyl peroxide, di-t-butyl peroxide, t-butylperoxy-2-ethylhexanoate, di-t-hexyl peroxide, t-hexylperoxy-2-ethylhexanoate, cumene hydroperoxide, t-butyl hydroperoxide, t-butylperoxy-2-ethylhexyl, and 2,3-dimethyl-2,3-diphenylbutane. Note that "t-butyl" means "tert-butyl."

[0090] When a thermal radical polymerization initiator is contained, the content of the thermal radical polymerization initiator in the composition for thermosetting resin of the present invention is preferably 0.01 to 5.0 mass%, more preferably 0.02 to 3.0 mass%, even more preferably 0.03 to 2.0 mass%, and particularly preferably 0.05 to 1.0 mass%.

[0091] (Photoradical Polymerization Initiator) The thermosetting resin composition of the present invention preferably contains a photoradical polymerization initiator. As the photoradical polymerization initiator, a compound typically used as a photoradical polymerization initiator can be used as appropriate depending on the conditions of the photopolymerization (photocuring) step described below. Specifically, the following compounds can be used. For example, 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)-2,4,4-trimethylpentylphosphine oxide, 1-phenyl-2-hydroxy-2-methylpropan-1-one, 1-hydroxycyclohexyl phenyl ketone, 1-(4-isopropylphenyl)-2-hydroxy-2-methylpropan-1-one, 1,2-diphenylethanedione, and methylphenyl glyoxylate. , 1-[4-(2-hydroxyethoxy)-phenyl]-2-hydroxy-2-methyl-1-propan-1-one, 2-hydroxy-1-{4-[4-(2-hydroxy-2-methyl-propionyl)-benzyl]phenyl}-2-methylpropan-1-one, 2,2-dimethoxy-1,2-diphenylethan-1-one, 2-methyl-1-(4-methylthiophenyl)-2-morpholinopropan-1-one, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butanone-1,2,4,6-trimethylbenzoyl-diphenyl-phosphine oxide, bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide, etc. Among the photoradical polymerization initiators listed above, acylphosphine oxide photoradical polymerization initiators are preferred because they can produce cured products with excellent light resistance.

[0092] Among these, in the present invention, 1-hydroxycyclohexyl phenyl ketone, bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide, 2,4,6-trimethylbenzoyl-diphenyl-phosphine oxide, 2,2-dimethoxy-1,2-diphenylethan-1-one, 1-[4-(2-hydroxyethoxy)-phenyl]-2-hydroxy-2-methyl-1-propan-1-one, or 2-methyl-1-(4-methylthiophenyl)-2-morpholinopropan-1-one can be preferably used as the photoradical polymerization initiator.

[0093] When a photoradical polymerization initiator is contained, the content of the photoradical polymerization initiator in the thermosetting resin composition is preferably 0.01 to 5.0 mass%, more preferably 0.05 to 1.0 mass%, and even more preferably 0.05 to 0.5 mass%. The thermosetting resin composition preferably contains both a photoradical polymerization initiator and a thermal radical polymerization initiator, and in this case, the total content of the photoradical polymerization initiator and the thermal radical polymerization initiator is preferably 0.01 to 5.0 mass%, more preferably 0.05 to 1.0 mass%, and even more preferably 0.05 to 0.5 mass%, relative to the total mass of the thermosetting resin composition.

[0094] As the photocationic polymerization initiator, a commonly used photocationic polymerization initiator can be used, and the amount of the initiator to be added can be adjusted appropriately.

[0095] From the viewpoint of improving the handleability when forming a cured product and forming a high-quality cured product, the viscosity of the composition for a thermosetting resin 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.

[0096] [Cured Product or Molded Product] The cured product of the present invention is a cured product obtained from the thermosetting resin composition of the present invention. That is, the cured product of the present invention is obtained by the progression of a polymerization reaction of raw material monomers of the thermosetting resin contained in the thermosetting resin composition of the present invention and curing. The polymerization reaction to obtain the cured product of the present invention includes curing by thermal polymerization, curing by photopolymerization using ultraviolet light, and curing using a curing accelerator without applying heat. Any of these methods may be used, or two or more of these may be used in combination. The cured product of the present invention may contain unreacted monomers (e.g., unreacted polymerizable compound of the present invention), etc. The molded product of the present invention is a molded product obtained from the thermoplastic resin-containing composition of the present invention. That is, the molded product of the present invention is obtained by molding the thermoplastic resin-containing composition of the present invention.

[0097] As described above, the cured product and molded article of the present invention exhibit reduced coloration, high anomalous partial dispersion, and excellent light resistance and heat resistance.

[0098] The Abbe number (νd) and partial dispersion ratio (θg, F) ​​of the cured product and molded product are values ​​measured using an ellipsometer (for example, J.A. Woollam, product name: M-2000XI-210). Specifically, for the cured product, measurements are taken of a cured product having a thickness of approximately 0.1 mm, produced using, for example, a transparent glass mold having a diameter of 20 mm. For the molded product, measurements are taken of, for example, a spin-coated film produced on a quartz substrate. The Abbe number (νd) and partial dispersion ratio (θg, F) ​​of the cured product and molded product are calculated using the following formula. JIS B 7090:1999 Optics and optical instruments - Reference wavelengths (ISO 7944:1998 Optics and optical instruments - Reference wavelengths) can also be referenced as appropriate. νd=(nd-1) / (nF-nC) θg,F=(ng-nF) / (nF-nC) Here, nd is the refractive index at a wavelength of 589 nm, nF is the refractive index at a wavelength of 486 nm, nC is the refractive index at a wavelength of 656 nm, and ng is the refractive index at a wavelength of 436 nm.

[0099] In a graph of Abbe number (νd) on the horizontal axis versus partial dispersion ratio (θg,F) on the vertical axis, the cured product and molded product of the present invention have a large deviation Δ(θg,F) (i.e., distance from the standard line) of the partial dispersion ratio (θg,F) from the standard line obtained by connecting glass type NSL7 (refractive index at d-line: 1.51, Abbe number (νd): 60.5, partial dispersion ratio (θg,F): 0.54), which is a standard for normal glass, with glass type PBM2 (refractive index at d-line: 1.62, Abbe number (νd): 36.3, partial dispersion ratio (θg,F): 0.58), and are located above the standard line, thereby exhibiting large positive anomalous partial dispersion. The deviation Δ(θg,F) of the partial dispersion ratio (θg,F) of the cured product and molded product of the present invention is preferably 0.04 or more, more preferably 0.08 or more, even more preferably 0.16 or more, and particularly preferably 0.20 or more. The upper limit of the deviation Δ(θg,F) of the partial dispersion ratio (θg,F) of the cured product and molded article of the present invention is not particularly limited, but is usually 0.50 or less.

[0100] The Abbe number (νd) 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, even more preferably 29 or less, and particularly preferably 28 or less. In addition, the Abbe number (νd) 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, even more preferably 5 or more, and particularly preferably 7 or more.

[0101] The partial dispersion ratio (θg,F) 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, even more preferably 0.72 or more, and particularly preferably 0.75 or more. The partial dispersion ratio (θg,F) 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 even more preferably 1.7 or less.

[0102] When used as lenses, the cured product and molded article of the present invention are required to have no absorption in the visible light region, i.e., transparency. The cured product and molded article of the present invention have substantially no absorption in the long wavelength region of the visible light region, and exhibit a decrease in transmittance toward the short wavelength side. Therefore, the transparency of the cured product and molded article of the present invention can be evaluated by measuring the transmittance at a wavelength of 430 nm. The transmittance at a wavelength of 430 nm of the cured product and molded article of the present invention is a value measured using an ultraviolet-visible spectrophotometer (e.g., UV-2600 (trade name, manufactured by Shimadzu Corporation)). Specifically, for the cured product, the transmittance at a wavelength of 430 nm is measured for a cured product having a thickness of approximately 0.1 mm, produced, for example, using a transparent glass mold having a diameter of 20 mm. Furthermore, for the molded article, the transmittance at a wavelength of 430 nm is measured for a molded article having a thickness of approximately 0.1 mm, produced, for example, using a spacer having a thickness of 0.1 mm. Furthermore, the light irradiation test for evaluating the light resistance of the cured product and molded product is conducted based on the xenon light irradiation test described in the Examples below, and the heating test for evaluating the heat resistance of the cured product and molded product is conducted based on the heating test described in the Examples below.

[0103] Preferred values ​​for the transmittance at a wavelength of 430 nm of the cured product and molded product of the present invention measured by the above method are described below. The transmittance immediately after preparation of the cured product and molded product 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. Furthermore, the transmittance of the cured product and molded product of the present invention after the light irradiation test is not particularly limited, but in Evaluation Item 3 (transmittance after 24-hour xenon light irradiation test) described below, it is preferably 72% or more, more preferably 75% or more, even more preferably 79% or more, and particularly preferably 81% or more. The decrease in transmittance of the cured product and molded product of the present invention before and after the light irradiation test is not particularly limited, but in Evaluation Item 3 (transmittance decrease before and after 24-hour xenon light irradiation test) described below, it is preferably 15% or less, more preferably 12% or less, even more preferably 8% or less, and particularly preferably 5% or less. The decrease in transmittance before and after the light irradiation test is calculated by subtracting the transmittance after the light irradiation test from the transmittance before the light irradiation test. Furthermore, the transmittance of the cured product and molded product of the present invention after a heating test is not particularly limited, but in evaluation item 4 (transmittance after a 30-minute heating test at 230°C) described below, it is preferably 72% or more, more preferably 75% or more, even more preferably 79% or more, and particularly preferably 81% or more. The decrease in transmittance of the cured product and molded product of the present invention before and after a heating test is not particularly limited, but in evaluation item 4 (transmittance after a 30-minute heating test at 230°C) described below, it is preferably 15% or less, more preferably 12% or less, even more preferably 8% or less, and particularly preferably 5% or less. The decrease in transmittance before and after the heating test is calculated by subtracting the transmittance after the heating test from the transmittance before the heating test.

[0104] In addition, preferred values ​​are described below for the transmittance at a wavelength of 430 nm of a composite lens (hereinafter simply referred to as a "composite lens" in this paragraph) including a lens substrate produced using the cured product or molded article of the present invention. The transmittance of the composite lens, 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. In addition, the transmittance of the composite lens after the light irradiation test is not particularly limited, but is preferably 74% or more, more preferably 75% or more, even more preferably 78% or more, and particularly preferably 79% or more, in evaluation item 3 (transmittance after 24-hour xenon light irradiation test) described below. The decrease in transmittance of the composite lens before and after the light irradiation test is not particularly limited, but in evaluation item 3 (the decrease in transmittance before and after a 24-hour xenon light irradiation test) described below, it is preferably 15% or less, more preferably 12% or less, even more preferably 8% or less, and particularly preferably 5% or less. 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. Furthermore, the transmittance of the composite lens of the present invention after a heating test is not particularly limited, but in evaluation item 4 (the transmittance after a 30-minute heating test at 230°C) described below, it is preferably 74% or more, more preferably 75% or more, even more preferably 78% or more, and particularly preferably 79% or more. The degree of decrease in transmittance of the composite lens before and after the heating test is not particularly limited, but in evaluation item 4 (transmittance after a heating test at 230°C for 30 minutes) described below, it is preferably 15% or less, more preferably 12% or less, even more preferably 8% or less, and particularly preferably 5% or less. The degree of decrease in transmittance before and after the heating test is calculated by subtracting the value of the transmittance after the heating test from the value of the transmittance before the heating test.The transmittance of the composite lens at a wavelength of 430 nm is a value measured using an ultraviolet-visible spectrophotometer (for example, UV-2600 (trade name, manufactured by Shimadzu Corporation)). Specifically, the transmittance at a wavelength of 430 nm is measured for a composite lens prepared in the same manner as in the preparation of the composite lens described in Reference Example 1 of WO 2022 / 255228.

[0105] [Method for producing cured product] The method for producing the cured product of the present invention is not particularly limited as long as it can produce a cured product of a thermosetting resin that does not soften or melt even when reheated, unlike thermoplastic resins, and can be any of curing by thermal polymerization, curing by photopolymerization using ultraviolet light, and curing using a curing accelerator without applying heat, or a combination of these. Among these, it is preferable to produce the cured product by a method including at least one of a step of photocuring the composition for a thermosetting resin of the present invention and a step of heat curing, and more preferably, a step of forming a semi-cured product by irradiating the composition for a thermosetting resin with ultraviolet light or heating the composition for a thermosetting resin with ultraviolet light, and a step of forming a cured product by irradiating the obtained semi-cured product with ultraviolet light or heating the semi-cured product with ultraviolet light.

[0106] Unless otherwise specified, the "step of forming a semi-cured product", the "step of forming a cured product", and the "semi-cured product" refer to the descriptions of "step of forming a semi-cured product", "step of forming a cured product", and "semi-cured product" in paragraphs

[0106] to

[0117] ,

[0118] to

[0124] , and

[0125] of WO 2019 / 044863, respectively, with "curable composition" being read as "composition for thermosetting resins of the present invention". In the present invention, the pressure in the pressurized deformation in the "step of forming a cured product" is preferably 0.098 to 9.8 MPa, more preferably 0.154 to 4.9 MPa, and even more preferably 0.154 to 2.94 MPa.

[0107] [Method for producing molded article] The molded article of the present invention can be produced by molding the thermoplastic resin-containing composition of the present invention. Examples of methods for molding the molded article include hot and pressure molding, such as compression molding, injection molding, extrusion molding, blow molding, and embossing.

[0108] Before performing hot and pressure molding, the thermoplastic resin-containing composition of the present invention may be pelletized. By pelletizing the thermoplastic resin-containing composition of the present invention, the handleability of the resin during hot and pressure molding can be improved. When pelletizing the thermoplastic resin-containing composition of the present invention, for example, a vented single-screw extruder or the like can be used.

[0109] When performing compression molding, a spacer of the desired thickness is used, and the thermoplastic resin-containing composition of the present invention (preferably pellets of the thermoplastic resin-containing composition of the present invention) is sandwiched between resin films such as polyimide films, heated and compressed, and then removed from the resin film along with the spacer, and cooled to room temperature (including by standing to cool). The conditions for performing heat compression are as follows: the heating temperature is preferably 180 to 450°C, more preferably 180 to 390°C; the pressure is preferably 0.098 to 9.8 MPa, more preferably 0.294 to 9.8 MPa, and even more preferably 1.0 to 9.8 MPa; and the pressure time is preferably 30 to 1000 seconds, more preferably 30 to 500 seconds, and even more preferably 60 to 500 seconds.

[0110] When injection molding is performed, an injection molding machine (including an injection compression molding machine) is used. In the injection molding machine, the molten thermoplastic resin-containing composition of the present invention is accumulated at the tip of a cylinder, and then the molten thermoplastic resin-containing composition of the present invention is injected into a mold to form the product. A commonly used injection molding machine can be used. The cylinder is preferably made of a material that exhibits low adhesion to the thermoplastic resin-containing composition of the present invention and is corrosion-resistant and abrasion-resistant. An example of an injection molding machine is the Micro-1 manufactured by Meiho Corporation.

[0111] The cylinder temperature during injection molding is preferably 200 to 450° C., more preferably 250 to 390° C. The mold temperature is preferably 50 to 300° C., more preferably 100 to 250° C.

[0112] [Uses of Cured Product and Molded Product] The cured product and molded product of the present invention are cured products or molded products that exhibit reduced coloration, high anomalous partial dispersion, and excellent light resistance and heat resistance, and therefore can be used in a variety of applications, and are particularly preferably used for optical components.

[0113] <Optical Element> The optical element of the present invention comprises the cured product or molded article of the present invention. The type of optical element is not particularly limited, but any optical element that transmits light (so-called passive optical element) can be suitably used. Examples of optical functional devices equipped with such an optical element include various display devices (liquid crystal displays, plasma displays, etc.), various projector devices (OHPs (overhead projectors), liquid crystal projectors, etc.), optical fiber communication devices (optical waveguides, optical amplifiers, etc.), and photographing devices such as cameras and videos.

[0114] Examples of passive optical components include lenses, prisms, prism sheets, panels (plate-shaped molded products), films, optical waveguides (film-shaped or fiber-shaped, etc.), optical disks, and sealants for LEDs (light-emitting diodes). Passive optical components may be provided with any coating layer or any additional functional layer as needed. For example, passive optical components may be provided with a protective layer that prevents mechanical damage to the coating surface due to friction or abrasion, a light-absorbing layer that absorbs light of undesirable wavelengths that cause deterioration of inorganic particles or substrates, a transmission-shielding layer that suppresses or prevents the transmission of reactive low molecules such as moisture or oxygen gas, an antiglare layer, an antireflection layer, a low-refractive index layer, etc. Specific examples of coating layers include transparent conductive films or gas barrier films made of inorganic oxide or inorganic nitride coating layers, and gas barrier films or hard coat films made of organic coating layers. The coating layer can be formed by a commonly used coating method such as vacuum deposition, CVD (Chemical Vapor Deposition), sputtering, dip coating, or spin coating.

[0115] [Lens Substrate] The optical component may be a lens substrate. That is, the cured product or molded product of the present invention may be used as a lens substrate. In the present invention, "lens substrate" refers to a single component capable of exhibiting lens function. A lens substrate produced using the cured product or molded product of the present invention is almost colorless, has high anomalous partial dispersion, and also exhibits excellent light resistance and heat resistance. Preferably, by appropriately adjusting the type of raw material monomer constituting the thermosetting resin composition of the present invention or the thermoplastic resin contained in the thermoplastic resin-containing composition of the present invention, the refractive index of the lens substrate can be adjusted as desired, and a lens substrate having a high refractive index, a high partial dispersion ratio, and light weight can be obtained.

[0116] A film or member can be provided on or around the surface of the lens substrate depending on the environment or application of the lens. For example, a protective film, anti-reflection film, hard coat film, etc. can be formed on the surface of the lens substrate. Furthermore, a lens substrate manufactured using the cured product or molded article of the present invention can be laminated with one or more other lens substrates selected from glass lens substrates, plastic lens substrates, etc. (hereinafter referred to as "other lens substrates") to form a composite lens. Such a composite lens can be produced, for example, by photocuring the thermosetting resin composition of the present invention on the other lens substrate to form a semi-cured product, and then heating the resulting semi-cured product to form a cured product. The above-mentioned descriptions can be preferably applied to the process of forming the semi-cured product and the process of forming the cured product, respectively. The cured product obtained using the thermosetting resin composition of the present invention is almost colorless, has high anomalous partial dispersion, and also exhibits excellent light resistance and heat resistance, thereby enabling the production of high-quality composite lenses. Furthermore, when the thermoplastic resin-containing composition of the present invention is used, for example, a melt of the pelletized thermoplastic resin-containing composition of the present invention is injected into a molding die using an injection molding machine, a transparent glass lens is placed over the resin so as to cover the entire surface on the side not in contact with the molding die, the lens is spread, and after cooling, the die is removed to obtain a composite lens. The periphery of the lens substrate may be fitted into a substrate-holding frame or the like to fix it. However, these films or frames are members added to the lens substrate and are distinguished from the lens substrate itself as defined in the present invention.

[0117] The lens of the present invention includes the cured product or molded article of the present invention. That is, when using the lens substrate as a lens, the lens substrate itself may be used alone as a lens, or the lens substrate may be used after adding the above-mentioned film or frame, other lens substrates, etc. The type or shape of the lens using the lens substrate is not particularly limited, but 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 lens substrate is preferably circular with a maximum diameter of 1 to 1000 mm. The maximum diameter is more preferably 2 to 200 mm, and even more preferably 2.5 to 100 mm.

[0118] The lens substrate is preferably used for imaging lenses for mobile phones or digital cameras, or imaging lenses for televisions or video cameras, as well as for in-vehicle lenses, endoscope lenses, and the like.

[0119] <Cemented Lens> A cemented lens can be produced by bonding a lens substrate or a lens produced using the composition of the present invention to another lens using a lens adhesive.

[0120] [Other Lenses] The type of other lenses is not particularly limited, and examples thereof include disc-shaped convex lenses, concave lenses, meniscus lenses, aspherical lenses, cylindrical lenses having cylindrical lens surfaces, ball lenses, rod lenses, etc. The material of the other lenses is not particularly limited, and they may be glass lenses, resin lenses, or composite lenses.

[0121] (Glass Lens) As the glass lens, any commonly used glass lens can be used without any restrictions. An example of a commercially available glass lens is BK7 (product name) manufactured by Ohara Corporation. When the composite lens includes a glass lens, a similar glass lens can also be used.

[0122] (Resin lens, composite lens) A resin lens refers to a lens made of a cured resin. In the present invention, the composite lens is preferably a lens including a layer made of glass and a resin layer. The resin layer is a layer made of a cured resin. Each layer included in the composite lens may be a lens (single lens), and in this case, it is preferable that the optical axis of each single lens (the line connecting the centers of curvature of both spherical surfaces) coincides. The composite lens may have a resin layer on its surface or inside.

[0123] [Lens Adhesive] Lens adhesives can be any commonly used lens adhesive without limitation. For example, the description of the compound represented by general formula (1) and its content described in paragraphs

[0241] to

[0268] of WO 2022 / 255228 can be applied to the present invention without particular restrictions. It is preferable to use a lens adhesive containing the compound represented by general formula (1) described in WO 2022 / 255228. Lens adhesives containing the compound represented by general formula (1) described in WO 2022 / 255228 absorb ultraviolet light while exhibiting excellent robustness against ultraviolet irradiation. Therefore, by using this lens adhesive, a cured product with high photostability can be obtained as a cemented lens. Furthermore, adhesive layers formed from lens adhesives containing the compound represented by general formula (1) described in WO 2022 / 255228 have high heat shock resistance.

[0124] (Polymer) The lens adhesive may contain a polymer or oligomer (hereinafter also referred to as "polymer") for the purpose of adjusting the viscosity or the Young's modulus of the cured product. As the polymer, the descriptions regarding the polymer and its content described in paragraphs

[0269] to

[0312] of WO 2022 / 255228 can be applied to the present invention without particular restrictions.

[0125] ((Meth)acrylate Monomer) The lens adhesive may contain a (meth)acrylate monomer. As the (meth)acrylate monomer, the same ones as those listed in the composition of the present invention described above can be used. Furthermore, the description relating to the (meth)acrylate monomer in paragraphs

[0313] to

[0315] of WO 2022 / 255228 can be applied to the present invention without particular limitations. With regard to the content of the (meth)acrylate monomer, the description relating to the content of the (meth)acrylate monomer in paragraph

[0316] of WO 2022 / 255228 can be applied to the present invention without particular limitations.

[0126] (Polymerization initiator) The lens adhesive preferably contains a photoradical polymerization initiator. The photoradical polymerization initiator may be the same as that described above in relation to the photoradical polymerization initiator in the composition of the present invention. The lens adhesive may also contain a thermal radical polymerization initiator in addition to the photoradical polymerization initiator. By further including a thermal radical polymerization initiator, it is possible to promote curing in areas that are not reached by light. The thermal radical polymerization initiator may be the same as that described above in relation to the thermal radical polymerization initiator in the composition of the present invention.

[0127] [Manufacturing of Cemented Lenses] A cemented lens can be obtained by overlapping two lenses with a lens adhesive therebetween and then curing the adhesive to form an adhesive layer. Curing is preferably carried out after the above overlapping and after removing any air bubbles that may have become mixed in the adhesive. The adhesive can be cured by light irradiation and / or heating. Curing is preferably carried out by at least light irradiation. A heating step may also be carried out after light irradiation. There are no particular limitations on the curing of the adhesive by light irradiation and heating, as long as an adhesive layer is formed, and curing can be carried out by a conventional method.

[0128] The thickness of the adhesive layer is preferably 10 to 50 μm, more preferably 20 to 30 μm. A thickness of 10 μm or more can sufficiently achieve the effect of absorbing ultraviolet light. Furthermore, a thickness of 50 μm or less can increase the transmittance in the short wavelength region of visible light (wavelength region of 400 to 430 nm) while exhibiting high adhesiveness.

[0129] 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 be bonded is small. Furthermore, the cutoff wavelength is preferably 380 nm or lower, more preferably 385 nm or lower, and even more preferably 390 nm or lower, for an adhesive layer with a film thickness of 30 μm. Here, the cutoff wavelength is defined as the wavelength at which the transmittance of the adhesive layer first becomes 0.5% or lower when measured from the wavelength side with the highest transmittance. The transmittance of the adhesive layer can be measured using a visible-ultraviolet spectrophotometer (e.g., UV-2550 (trade name) manufactured by Shimadzu Corporation). For example, the refractive index and cutoff wavelength of the adhesive layer can be adjusted within the above ranges by adjusting the amount of the compound represented by general formula (1) described in WO 2022 / 255228 in the lens adhesive.

[0130] The present invention will be described in more detail below based on examples. The materials, amounts used, ratios, treatment details, treatment procedures, etc. shown in the following examples can be changed as appropriate without departing from the spirit of the present invention. Therefore, the scope of the present invention should not be interpreted as being limited by the specific examples shown below. The compounds and polymerizable compounds were stored under yellow light until they were used for light resistance evaluation.

[0131] Examples [Synthesis Examples] Compounds were synthesized as follows: In addition, room temperature means 25°C, and eq. means molar equivalent.

[0132] 1. Synthesis of Intermediate-1 and Compound A-1

[0133] A solution of 2,5-dihydroxyacetophenone (25 g, 1 eq.) and 4-hydroxyphenylacetic acid (28 g, 1.1 eq.) in acetic anhydride (Ac ２ 0, 70 mL, 4.5 eq.) suspension was added at 0° C. to triethylamine (Et ３ N,N-dimethylacetamide (69 mL, 3 eq.) was slowly added. After stirring at 135°C for 2 hours, the mixture was cooled to room temperature, water was added to stop the reaction, and the resulting solid was collected by filtration. Chilled water was used to wash the solid. Methanol (200 mL) and hydrochloric acid (6 mol / L, 200 mL) were added to the resulting solid, and the mixture was stirred under reflux for 4 hours. The mixture was then cooled to room temperature, and the resulting solid was collected by filtration. Chilled water was used to wash the solid. The resulting solid was dried to obtain Intermediate-1 (37 g, yield 85%) as a white solid. To a solution of Intermediate-1 (2.7 g, 1 eq.) and ethylene carbonate (1.9 g, 2.1 eq.) in N,N-dimethylacetamide (DMAc, 10 mL) was added potassium carbonate (0.2 g, 0.2 eq.) at room temperature. After stirring at 130°C for 4 hours, the mixture was cooled to 0°C, water was added to stop the reaction, and the resulting solid was collected by filtration. The solid was washed with chilled water. The resulting solid was purified by recrystallization using ethyl acetate to obtain Compound A-1 (1.7 g, yield 47%) as a white solid. Intermediate-1 １ H-NMR (400MHz, DMSO-d ６ ): δ = 9.70 (brs, 1H), 9.61 (brs, 1H), 7.26 (d, 1H, J = 8.0Hz), 7.12-7.02 (m, 4H), 6.83-6.81 (m, 2H), 2.22 (s, 3H) (several signals overlapped). Compound A-1 １ H-NMR (400MHz, DMSO-d ６ ): δ = 7.37 (d, 1H, J = 8.0Hz), 7.27-7.22 (m, 4H), 7.03-7.00 (m, 2H), 4.93- 4.89 (m, 2H), 4.10-4.03 (m, 4H), 3.77-3.73 (m, 4H), 2.28 (s, 3H) (several signals overlapped).

[0134] 2. Synthesis of Compound B-1

[0135] 2.2 g of Compound B-1 was obtained in the same manner as in the synthesis of Compound A-1, except that 2,5-dihydroxyacetophenone was replaced with 2,5-dihydroxybenzaldehyde. １ H-NMR (400MHz, DMSO-d ６ ): δ = 8.15 (s, 1H), 7.70 (d, 2H, J = 8.0Hz), 7.39-7.31 (m, 2H), 7.20 (dd, 1H, J = 8 .0, 4.0Hz), 7.04-7.02 (m, 2H), 4.05-4.00 (m, 4H), 3.76-3.72 (m, 4H) (several signals overlapped).

[0136] 3. Synthesis of Compound C-1

[0137] 1.1 g of compound C-1 was obtained in the same manner as in the synthesis of compound A-1, except that 2,5-dihydroxyacetophenone was replaced with 2,4-dihydroxyacetophenone. １ H-NMR (400MHz, CDCl ３ ): δ = 7.57 (d, 1H, J = 12.0Hz), 7.27-7.22 (m, 2H), 6.99-6.86 (m, 4H), 4.14-4.07 (m, 4H), 3.82-3.76 (m, 4H), 2.30 (s, 3H) (several signals overlapped).

[0138] 4. Synthesis of Compound D-1

[0139] 2.5 g of Compound D-1 was obtained in the same manner as in the synthesis of Compound A-1, except that 2,5-dihydroxyacetophenone was replaced with 2,4-dihydroxybenzaldehyde. Compound D-1 １ H-NMR (400MHz, CDCl ３ ): δ = 7.72 (s, 1H), 7.67-7.64 (m, 2H), 7.42 (d, 1H, J = 8.0Hz), 6.98-6.86 (m, 4H), 4.11-4.04 (m, 4H), 3.78-3.73 (m, 4H) (several signals overlapped).

[0140] 5. Synthesis of Compound G-1

[0141] 0.9 g of compound G-1 was obtained in the same manner as in the synthesis of compound A-1, except that 4-hydroxyphenylacetic acid was replaced with 3-hydroxyphenylacetic acid. １ H-NMR (400MHz, DMSO-d ６ ): δ=7.35-6.97 (m, 7H), 4.11-4.04 (m, 4H), 3.75-3.71 (m, 4H), 2.27 (s, 3H) (several signals overlapped).

[0142] 6. Synthesis of Compound A-201

[0143] To a solution of intermediate-1 (2.7 g, 1 eq.) and cesium carbonate (6.5 g, 2 eq.) in N,N-dimethylacetamide (DMAc, 20 mL) was added dropwise propylene oxide (1.8 g, 3 eq.) at 0°C. After stirring at 80°C for 8 hours, the mixture was cooled to 0°C, water was added to terminate the reaction, and the resulting solid was collected by filtration. Chilled water was used to wash the solid. The resulting solid was purified by recrystallization using hexane and ethyl acetate to obtain compound A-201 (0.8 g, yield 22%) as a cream-colored solid. Compound A-201 １ H-NMR (400MHz, DMSO-d ６ ): δ = 7.38 (d, 1H, J = 8.0Hz), 7.29-7.25 (m, 4H), 7.04-7.00 (m, 2H), 4.35-3.91 (m, 6H), 2.29 (s, 3H), 1.32-1.28 (m, 6H) (several signals overlapped).

[0144] The transmittance, anomalous partial dispersion, light resistance, and heat resistance of each of the compounds prepared above, as well as the comparative compounds CM-1 and CM-2 described below, were evaluated as follows. The results are shown in Table 1.

[0145] <Evaluation Item 1: Transmittance> Using a Shimadzu ultraviolet-visible spectrophotometer (trade name: UV-2550) manufactured by Shimadzu Corporation, the transmittance of the diluted solution at a wavelength of 430 nm was measured under the following conditions, and evaluated according to the following criteria. A higher transmittance at a wavelength of 430 nm indicates less yellow coloration. (Measurement Conditions) Cell: Square quartz cell (optical path length: 1 cm) Sample: The compound of the present invention or the comparative compound was dissolved in tetrahydrofuran (THF) to a concentration of 50.0 mg / 5 mL. Blank: THF - Evaluation Criteria - A: 98% or more B: 96% or more and less than 98% C: 94% or more and less than 96% D: Less than 94%

[0146] <Evaluation Item 2: Abnormal Partial Dispersibility> (1) Sample Preparation 0.20 g of the compound of the present invention or the comparative compound and 0.80 g of polycarbonate (manufactured by Teijin Limited, trade name: Panlite L-1225Y) were dissolved in 20 mL of cyclohexanone to prepare coating solution 1. Similarly, 0.40 g of the compound of the present invention or the comparative compound and 0.60 g of polycarbonate (manufactured by Teijin Limited, trade name: Panlite L-1225Y) were dissolved in 20 mL of cyclohexanone to prepare coating solution 2. Furthermore, 1.0 g of polycarbonate (manufactured by Teijin Limited, trade name: Panlite L-1225Y) was dissolved in 20 mL of cyclohexanone to prepare coating solution 3. Each coating solution was spin-coated onto a quartz substrate to prepare a spin-coated film consisting of a mixture of polycarbonate (resin) and the compound or a spin-coated film of polycarbonate (resin), which was used as a sample for refractive index measurement. (2) Evaluation of Anomalous Partial Dispersion The refractive indexes of the refractive index measurement samples prepared above were measured at wavelengths of 436 nm, 486 nm, 589 nm, and 656 nm using an ellipsometer (manufactured by J.A. Woollam, trade name: M-2000XI-210). From the refractive index values ​​at each wavelength of the refractive index measurement samples prepared using each of Coating Solutions 1 to 3, the refractive index at the point where the blending ratio of the compound of the present invention or the comparative compound was 100% was calculated for each wavelength as an extrapolated value using the refractive indexes at three points where the blending ratio of the compound of the present invention or the comparative compound was 0%, 20%, and 40%, and the partial dispersion ratios (θg, F) ​​and Abbe numbers (νd) of the refractive indexes of the compound of the present invention and the comparative compound were calculated using the following formulas. νd=(nd-1) / (nF-nC) θg,F=(ng-nF) / (nF-nC) In the above formulas, nd is the refractive index at a wavelength of 589 nm, nF is the refractive index at a wavelength of 486 nm, nC is the refractive index at a wavelength of 656 nm, and ng is the refractive index at a wavelength of 436 nm. nd, nF, nC, and ng are all refractive indices (extrapolated values) at the point where the blending ratio of the above compound or comparative compound is 100%.Next, in a graph of Abbe number (νd) on the horizontal axis versus partial dispersion ratio (θg,F) on the vertical axis, the standard line obtained by connecting glass type NSL7 (refractive index at d-line: 1.51, Abbe number (νd): 60.5, partial dispersion ratio (θg,F): 0.54) serving as a standard for normal glass with glass type PBM2 (refractive index at d-line: 1.62, Abbe number (νd): 36.3, partial dispersion ratio (θg,F): 0.58) was obtained, and the deviation Δ(θg,F) (i.e., the distance from the standard line) of the partial dispersion ratio (θg,F) was determined for each of the compounds of the present invention and the comparative compounds, and evaluated according to the following criteria. In addition, the value of Δ(θg,F) was also determined for a sample prepared from Coating Liquid 3, and this was evaluated as a comparative sample according to the following criteria. Note that both NSL7 and PBM2 are optical glasses manufactured by Ohara Inc. The definitions of nd, vd and θg,F are the same as those in the above formula. Evaluation Criteria A: 0.20 or more B: 0.16 or more and less than 0.20 C: 0.08 or more and less than 0.16 D: 0.04 or more and less than 0.08 E: Less than 0.04.

[0147] <Evaluation Item 3: Lightfastness> (1) Preparation of Lightfastness Evaluation Sample 0.20 g of the compound of the present invention or the comparative compound and 0.80 g of polycarbonate (manufactured by Teijin Limited, trade name: Panlite L-1225Y) were dissolved in 5.0 mL of methylene chloride. 1.5 g of this was weighed out and placed in an aluminum dish with a diameter of 4 cm, and dried at room temperature for 3 days to prepare a film-like sample for lightfastness evaluation with a thickness of approximately 0.1 mm. Additionally, 1.0 g of polycarbonate (manufactured by Teijin Limited, trade name: Panlite L-1225Y) was dissolved in 5.0 mL of methylene chloride and dried on an aluminum dish in the same manner as above to prepare a comparative film with a thickness of approximately 0.1 mm. (2) Evaluation of Lightfastness The lightfastness evaluation sample prepared above was subjected to a xenon light irradiation test under the following conditions, and the decrease in transmittance at a wavelength of 450 nm before and after irradiation with xenon light was determined, and lightfastness was evaluated according to the following criteria. This irradiation test corresponds to an accelerated light resistance test under a sunlight environment. For all of the compounds A-1, B-1, C-1, D-1, A-201, and G-1 of the present invention, the decrease in transmittance at a wavelength of 430 nm itself was not different from the decrease in transmittance at a wavelength of 450 nm, and the evaluation classification was the same. The decrease in transmittance is a value calculated by subtracting the transmittance value after irradiation with xenon light from the transmittance value before irradiation with xenon light. (Xenon Light Irradiation Conditions) Apparatus: Xenon Accelerated Weathering Tester Q-SUN Xe-1 (trade name, manufactured by Q-Lab Corporation) Light Source: Xenon Arc Lamp Optical Filter: Extended UV Q / B (trade name, manufactured by Q-Lab Corporation) Illuminance: 0.43 W / m ２ (340 nm illuminance meter) Black panel temperature: 63°C Test time: 24 hours (Transmittance measurement conditions) Using a Shimadzu ultraviolet-visible spectrophotometer (product name: UV-2550) manufactured by Shimadzu Corporation, the transmittance of the diluted solution was measured at a wavelength of 430 nm or 450 nm under the following conditions. Sample: Lightfastness evaluation sample before or after the xenon light irradiation test (optical path length: approximately 0.1 mm) Blank: Comparative film - Evaluation criteria - A: The transmittance decreased by less than 5% B: The transmittance decreased by 5% or more but less than 8% C: The transmittance decreased by 8% or more but less than 10% D: The transmittance decreased by 10% or more

[0148] <Evaluation Item 4: Heat Resistance> (1) Preparation of Sample for Heat Resistance Evaluation 50 mg of the compound of the present invention or the comparative compound was weighed into an aluminum cup. (2) Evaluation of Heat Resistance A heating test was performed on the heat resistance evaluation sample prepared above under the conditions described below, and then a diluted solution of the test sample was prepared under the conditions described below. The decrease in transmittance at a wavelength of 450 nm before and after the heating test was determined, and the heat resistance was evaluated according to the following criteria. Note that for all of the compounds A-1, B-1, C-1, D-1, A-201, and G-1 of the present invention, the decrease in transmittance at a wavelength of 430 nm itself was not different from the decrease in transmittance at a wavelength of 450 nm, and the evaluation category was the same. The decrease in transmittance is a value calculated by subtracting the transmittance value after the heating test from the transmittance value before the heating test. (Heating test conditions) Apparatus: Inert oven (trade name STPH-101M, manufactured by ESPEC Corporation) Heating temperature: 230°C Atmosphere: Nitrogen atmosphere (oxygen concentration 0.1% or less) Test time: 30 minutes (Transmittance measurement conditions) Using an ultraviolet-visible spectrophotometer (trade name: UV-2550) manufactured by Shimadzu Corporation, the transmittance of the diluted solution was measured at a wavelength of 450 nm under the following conditions. Cell: Square quartz cell (optical path length: 1 cm) Sample: The sample for evaluating heat resistance before or after the heating test was dissolved in tetrahydrofuran (THF) to adjust the concentration to 50.0 mg / 5 mL. Blank: THF - Evaluation criteria - A: The transmittance decreased by less than 5% B: The transmittance decreased by 5% or more but less than 8% C: The transmittance decreased by 8% or more but less than 10% D: The transmittance decreased by 10% or more

[0149]

[0150] Notes for the table: Compounds:

[0151] CM-1 and CM-2: Comparative compounds CM-1 and CM-2, respectively. Comparative compound CM-2 corresponds to compound 3 described in Scheme 2 of Macromolecules, 2013, Vol. 46, No. 13, pp. 5133-5140. The column for comparative sample shows data for polycarbonate (manufactured by Teijin Limited, trade name: Panlite L-1225Y) alone, which does not contain the compound or comparative compound. A "-" in the transmittance and heat resistance indicates that no comparative sample is available.

[0152] The results in Table 1 reveal the following: Comparative compound CM-1 is a compound having the R １ ~R ９and two of the substituents possessed by L in general formula (2) are alkylene groups having a substituent, rather than being unsubstituted. This comparative compound CM-1 exhibited a large decrease in transmittance at a wavelength of 450 nm of 10% or more upon heating at 230°C for 30 minutes, and thus exhibited poor heat resistance. Furthermore, comparative compound CM-2 exhibited a small deviation Δ(θg,F) of the partial dispersion ratio (θg,F) from the standard line of 0.04 or more and less than 0.08, a large decrease in transmittance at a wavelength of 450 nm upon irradiation with xenon light of 8% or more and less than 10%, and a large decrease in transmittance at a wavelength of 450 nm upon heating at 230°C for 30 minutes of 10% or more, and thus exhibited low anomalous partial dispersion and poor light resistance and heat resistance. In contrast, compounds A-1, B-1, C-1, D-1, A-201 and G-1 of the present invention all have a high transmittance at a wavelength of 430 nm of 94% or more, a large deviation Δ(θg,F) of the partial dispersion ratio (θg,F) from the standard line of 0.08 or more, a small decrease in transmittance at a wavelength of 450 nm due to irradiation with xenon light of less than 8%, and a small decrease in transmittance at a wavelength of 450 nm due to heating of less than 5%. Therefore, it was found that coloring was suppressed, abnormal partial dispersion was high, and light resistance and heat resistance were excellent. Among these, when the compound is represented by general formula (1-1) or (1-2), the transmittance, anomalous partial dispersion, and light resistance are all further improved (Compound A-1 compared to Compound G-1), and when R is an aliphatic hydrocarbon group which may have a substituent, the transmittance at a wavelength of 430 nm can be increased to 98% or more, and coloration can be further suppressed (Compound A-1 compared to Compound B-1, Compound C-1 compared to Compound D-1). Thus, the compounds of the present invention suppress coloration and are excellent in anomalous partial dispersion, light resistance, and heat resistance.Therefore, it can be seen that the cured product and molded article of the present invention obtained using the composition for thermosetting resins or the composition containing a thermoplastic resin containing the compound of the present invention, as well as the cured product of the present invention obtained using the polymerizable compound derived from the compound of the present invention and the composition for thermosetting resins containing the same, are excellent in abnormal partial dispersibility, light resistance, and heat resistance, and further, coloration derived from the compound of the present invention or the polymerizable compound of the present invention is suppressed.

[0153] [Reference Example: Esterification reaction using compounds A-1 and A-201 prepared above]

[0154] 1. Synthesis of polymerizable compound A-1M

[0155] A solution of compound A-1 (3.56 g, 1 mol equivalent) and methacrylic acid chloride (2.09 g, 2 mol equivalent) in dichloromethane was added with triethylamine (Et ３ N, 3.03 g, 3 mol equivalents) was added, and the reaction was tracked by HPLC (High Performance Liquid Chromatography). It was confirmed that the raw materials were completely converted into the target product after a reaction time of 60 minutes at room temperature. The mixture was then separated with water and saturated saline, and the organic layer was concentrated to obtain polymerizable compound A-1M with a purity of 98.0%. １ H-NMR (400MHz, DMSO-d ６ ): δ = 7.38 (d, 1H, J = 8.0Hz), 7.29-7.22 (m, 4H), 7.13-7.02 (m, 2H), 6.20-6.15 (m, 2H), 5.71- 5.60 (m, 2H), 4.62-4.38 (m, 4H), 4.33-4.12 (m, 4H), 2.30 (s, 3H), 2.00-1.98 (m, 6H) (several signals overlapped).

[0156] 2. Synthesis of polymerizable compound A-201M

[0157] In the same manner as in the synthesis of compound A-1M, a dichloromethane solution of compound A-201 (3.84 g, 1 mol equivalent) and methacrylic acid chloride (2.09 g, 2 mol equivalent) was dissolved in triethylamine (Et ３N, 3.03 g, 3 mol equivalents) was added, and the reaction was tracked by HPLC. After a reaction time of 60 minutes at room temperature, 30% of the monomethacrylic form remained. Therefore, methacrylic acid chloride (1.04 g, 1 mol equivalent) and triethylamine (1.01 g, 1 mol equivalent) were further added, and the reaction was continued overnight at room temperature, confirming that the raw materials had been completely converted into the target product. A separation operation was performed with water and saturated saline, and the organic layer was concentrated to obtain polymerizable compound A-201M with a purity of 96.7%. Polymerizable compound A-201M １ H-NMR (400MHz, DMSO-d ６ ): δ = 7.39 (d, 1H, J = 8.0Hz), 7.28-7.21 (m, 4H), 7.12-7.00 (m, 2H), 6.22-6.15 (m, 2H), 5.72- 5.60 (m, 2H), 4.88-3.91 (m, 6H), 2.29 (s, 3H), 2.00-1.98 (m, 6H), 1.32-1.28 (m, 6H) (several signals overlapped).

[0158] The coloring quality of the obtained polymerizable compounds A-1M and A-201M was evaluated in the same manner as in the above evaluation item 1: transmittance. The results are summarized in Table 2.

[0159]

[0160] Among the compounds of the present invention, polymerizable compounds A-1M and A-201M, which are obtained by converting a hydroxy group in a substituent represented by general formula (2) to a methacryloyloxy group, both have a high transmittance of 96% or more at a wavelength of 430 nm and are found to be almost free of coloration. In particular, when the substituent represented by general formula (2) is a substituent represented by general formula (2-1), the polymerizable compound obtained by the esterification reaction has a high transmittance of 98% or more, and coloration is further suppressed (polymerizable compound A-1M relative to polymerizable compound A-201M). Furthermore, when polymerizable compounds A-1M and A-201M were evaluated for anomalous partial dispersibility, light fastness, and heat resistance using the same methods as in evaluation items 2 to 4 above, it was confirmed that they exhibited high anomalous partial dispersibility comparable to that of compounds A-1 and A-201, respectively, and excellent light fastness and heat resistance.

[0161] This application claims priority based on Japanese Patent Application No. 2023-222012, filed on December 27, 2023, the contents of which are incorporated herein by reference as part of the present specification.

Claims

1. A compound represented by the following general formula (1). In the above formula, R represents a hydrogen atom, an aliphatic hydrocarbon group, or an aromatic hydrocarbon group. R １ to R ９ Two of them represent a substituent represented by the following general formula (2), and the remaining seven represent a hydrogen atom or a monovalent substituent different from the substituent represented by the following general formula (2). In the above formula, L represents an unsubstituted alkylene group having 2 to 6 carbon atoms. * represents a bond.

2. The compound according to claim 1, which is represented by the following general formula (1-1) or (1-2). In the above formula, R １ ~R ６ , R ８ and R ９ represent a hydrogen atom or a monovalent substituent different from the substituent represented by the general formula (2), and L １ and L ２ represent an unsubstituted alkylene group having 2 to 6 carbon atoms. R has the same meaning as the above R.

3. The compound according to claim 1, wherein the substituent represented by the general formula (2) is represented by the following general formula (2-1). In the above formula, L Ａ represents an unsubstituted alkylene group having 1 to 5 carbon atoms. * represents a bond.

4. The compound according to claim 1, wherein R is an aliphatic hydrocarbon group.

5. A polymerizable compound obtained by introducing a polymerizable group represented by any one of the following formulas (Pol-1) to (Pol-6) using the hydroxy group in the substituent represented by the general formula (2) in the compound according to claim 1 as a reactive group. In the above formula, * indicates a bond to L in the general formula (2).

6. A thermoplastic resin-containing composition comprising the compound according to claim 1, provided that the compound according to claim 1 is not incorporated as a structural unit of the polymer constituting the thermoplastic resin.

7. A composition for a thermosetting resin comprising the compound according to claim 1.

8. A composition for a thermosetting resin comprising the polymerizable compound according to claim 5.

9. A molded article of the thermoplastic resin-containing composition according to claim 6.

10. A cured product obtained from the composition for a thermosetting resin according to claim 7.

11. A cured product obtained from the composition for a thermosetting resin according to claim 8.

12. An optical member comprising the molded article according to claim 9 or the cured product according to claim 10 or 11.

13. A lens comprising the molded article according to claim 9 or the cured product according to claim 10 or 11.

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