Photochromic compound, propargyl alcohol compound, curing composition, optical item, lens and glasses

Description

Photochromic compound, propargyl alcohol compound, curable composition, optical article, lens and eyeglasses TECHNICAL FIELD

[001] The present invention relates to a photochromic compound, a propargyl alcohol compound, a curable composition, an optical article, a lens and eyeglasses. PRECEDENT TECHNIQUE

[002] Photochromic compounds refer to compounds that can reversibly become two types of isomers with different absorption spectra upon irradiation with light, including ultraviolet rays, such as sunlight or the light from a mercury lamp. Generally, when a colorless compound in a colorless state is irradiated with ultraviolet rays, it rapidly changes color and isomerizes to a colored state (chromogenic reaction). Photochromic compounds have been researched and developed as materials for photochromic lenses.

[003] In applications for such photochromic lenses, the photochromic compounds require the following properties in some cases. (I) Low degree of coloration in the visible light region prior to UV irradiation (hereinafter referred to as initial coloration). (II) High rate at which the optical color density reaches saturation after the start of UV irradiation (hereinafter referred to as optical color density). (III) High rate at which the optical density of the color reaches saturation after the start of UV irradiation (hereinafter also referred to as high chromogenic sensitivity). (IV) High rate at which the compound returns to its original state after the interruption of UV irradiation (hereinafter referred to as the color fading rate). Petition 870250084631, dated 09 / 19 / 2025, page 6 / 223 2 / 180 (V) High durability against the aforementioned repeated reversible actions. (VI) High solubility in the lens matrix material and high dispersibility in a cured product.

[004] As photochromic compounds that can satisfy the above properties, several types of chromene compounds have been studied. For example, a chromene compound represented by formula (A) below (Patent Document 1), a chromene compound represented by formula (B) below (Patent Document 2) and a chromene compound represented by formula (C) below (Patent Document 3) are known. Chemical Formula 1 Chemical Formula 2 Petition 870250084631, dated 09 / 19 / 2025, page 7 / 223 3 / 180 Chemical Formula 3 (W) List of citations Patent Documents

[005] Patent document 1: International publication PCT no. WO 1996 / 014596

[006] Patent document WO 2004 / 085568 2: International publication PCT no.

[007] Patent document WO 2001 / 060811 3: International publication PCT no.

[008] Patent document WO 2015 / 035325 4: International publication PCT no.

[009] Patent document WO 2007 / 078529 5: International publication PCT no.

[0010] Patent document WO 2021 / 075456 6: International publication PCT no.

[0011] Patent document WO 2018 / 235771 7: International publication PCT no.

[0012] Patent document WO 2012 / 105410 patent 8: International Publication PCT No.

[0013] WO Document 2011 / 053615 patent 9: International Publication PCT No.

[0014] Patent Document 10: WO 2013 / 042800: International Publication PCT No. Petition 870250084631, dated 09 / 19 / 2025, page 8 / 223 4 / 180

[0015] Patent document 11: International publication PCT no. WO 2019 / 228604

[0016] Patent document 12: International publication PCT No. WO 2019 / 013249

[0017] Patent document 13: International publication PCT No. WO 2016 / 143910 Non-patent documents

[0018] Non-patent document 1: Journal of Organic Chemistry, 69(10), pp. 3282-3293; 2004

[0019] Non-patent document 2: Synthetic communications, 23(16), pp. 2241-2249 (1993)

[0020] Non-patent document 3: J. Am. Chem. Soc., 132(41), pp. 14324-14326 (2010)

[0021] Non-patent document 4: Org. Lett., 16, pp. 6492-6495 (2014) DISCLOSURE OF THE INVENTION Problems to be solved by the invention

[0022] An object of the present invention is to provide a photochromic compound with excellent color fading rate and durability, a propargyl alcohol compound that can serve as an intermediate for this photochromic compound, as well as a curable composition, an optical article, a lens and eyeglasses including this photochromic compound. Ways to solve the problems

[0023] This disclosure refers to a photochromic compound having a skeleton represented by formula (1) below. Petition 870250084631, dated 09 / 19 / 2025, page 9 / 223 5 / 180 Chemical Formula 4

[0024] In formula (1) above, M is C, Si or Ge.

[0025] R3 is an aryl group or a heteroaryl group replaced by a group represented by formula (1a) below. Chemical Formula 5 (1a)

[0026] In formula (1a) above, R1 is a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted fused polycyclic ring in which an aromatic ring or an aromatic heterocyclic ring is fused with such substituents. R2 is a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted haloalkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted aralkyl group, or a group represented by formula (2a) below. -Q1-(X1Q2)a-X2Q3(2a)

[0027] In formula (2a) above, Q1 is an alkylene group or a haloalkylene group. Q2 is an alkylene group or a haloalkylene group. Petition 870250084631, dated 09 / 19 / 2025, p. 10 / 223 6 / 180 Q3 is an alkyl group or a haloalkyl group. X1 and X2 are each independently O, S, NR700, PR701, or P(=O). R700 and R701 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[0028] a is an integer of 0, or 1 or more and 3 or less.

[0029] R4 is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group.

[0030] Ring A and ring B are each independently a substituted or unsubstituted aromatic ring, a substituted or unsubstituted aromatic heterocyclic ring, or a substituted or unsubstituted fused polycyclic ring in which an aromatic ring or an aromatic heterocyclic ring is fused with these rings.

[0031] In addition, the present disclosure relates to a curable composition. The curable composition includes the photochromic compound described above and at least one compound selected from a group consisting of a radical polymerizable monomer, a cationic polymerizable monomer, a compound with a polymerizable group and a (thio)urethane(urea) polymer.

[0032] In addition, this disclosure relates to an optical article. The optical article includes the cured product of the curable composition described above.

[0033] In addition, the present disclosure refers to a lens. The lens includes the photochromic compound described above.

[0034] In addition, this disclosure refers to eyeglasses. The eyeglasses include the lenses described above.

[0035] In addition, the present disclosure relates to a propargyl alcohol compound. The propargyl alcohol compound has a skeleton represented by formula (9) below. Petition 870250084631, dated 09 / 19 / 2025, p. 11 / 223 7 / 180 Chemical Formula 6 k <9>

[0036] In formula (9), R3 and R4 are each independently the same as those in formula (1) above. Effects of the invention

[0037] The present invention provides a photochromic compound with excellent color fading rate and durability, a propargyl alcohol compound that can serve as an intermediate for this photochromic compound, as well as a curable composition, an optical article, a lens and eyeglasses including this photochromic compound. PREFERRED METHOD FOR CARRYING OUT THE INVENTION Photochromic Compound

[0038] According to the embodiment, a photochromic compound is provided having a skeleton represented by formula (1) below. Chemical Formula 7

[0039] In formula (1), M is C, Si or Ge.

[0040] R3 is an aryl group or heteroaryl group substituted by a group represented by formula (1a) below. R4 is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. Rings A and B are each independently a substituted or unsubstituted aromatic ring, a substituted or unsubstituted aromatic heterocyclic ring, or a substituted or unsubstituted fused polycyclic ring in which an aromatic ring or a ring Petition 870250084631, dated 09 / 19 / 2025, p. 12 / 223 The 8 / 180 aromatic heterocyclic compound is fused with these rings. Chemical Formula 8 p1 „ 'N'' (1a)

[0041] In formula (1a) above, R1 is a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted fused polycyclic ring in which an aromatic ring or an aromatic heterocyclic ring is fused with these substituents.

[0042] R2 is a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted haloalkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted aralkyl group or a group represented by formula (2a) below. -Q1-(X1Q2)a-X2Q3 (2a)

[0043] In formula (2a) above, Q1 is an alkylene group or a haloalkylene group, Q2 is an alkylene group or a haloalkylene group, Q3 is an alkyl group or a haloalkyl group, X1 and X2 are each independently O, S, NR700, PR701 or P(=O), R700 and R701 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. Petition 870250084631, dated 09 / 19 / 2025, page 13 / 223 9 / 180 tuído, a is an integer of 0, or 1 or more and 3 or less,

[0044] This photochromic compound exhibits excellent fade rate and durability. Although the reason for this is not yet clear, the inventors consider the reason to be as follows:

[0045] First, in the photochromic compound with the skeleton represented by formula (1), R3 is a substituted aryl or a substituted heteroaryl. The inventors found that this substituent significantly affects the color fading rate. This means that the stronger the electron donation of R3, the lower the thermal stability of the color development structure when the photochromic compound is photoisomerized by light, and therefore the photochromic compound will be subject to fading, resulting in a high color fading rate. However, organic compounds with electron-donating substituents generally tend to be susceptible to oxidation due to the abundance of electrons in their molecules. In particular, photochromic compounds have a tendency for repeat durability to decrease due to oxidation.For example, photochromic compounds with a substituent with high electron-donating properties, such as substituted amino groups or nitrogen-containing heterocyclic rings, exhibit excellent color fading rates but have low repeatability, and therefore it has been difficult for photochromic compounds to achieve both color fading rate and repeatability in many cases.

[0046] The R3 substituent of the photochromic compound, according to the embodiment, has the substituent represented by formula (1a) above. Formula (1a) above has a substituted amino group structure, with an aryl or heteroaryl group directly attached to one of the bonding ends of a nitrogen atom, and with a group other than aryl or heteroaryl groups, or a hi atom Petition 870250084631, dated 09 / 19 / 2025, page 14 / 223 drogen 10 / 180, attached to the other bonding end. Since an aryl or heteroaryl group is directly attached to one of the bonding ends of a nitrogen atom, formula (1a) is considered to be conjugated with the aryl or heteroaryl group substituted via a p orbital on a nitrogen atom. Compounds with such a structure are considered to have extended conjugation compared to compounds without an amino group with substituted aryl or heteroaryl groups. It is considered that, as this extension displaces electrons in a color developer due to a resonance structure, oxidation is hardly caused and repeat durability can be improved. Furthermore, such a compound is expected to be excellent in both color fading rate and repeat durability because its conjugation is not excessively extended compared to a case where R3 has, as a substituent, an amino group with a diaryl group.

[0047] Based on the description above, the use of the photochromic compound, according to the modality, makes it possible to obtain a cured product with an excellent color fading rate and, in addition, repeat durability. Thus, such a photochromic compound is suitable for optical articles, such as photochromic glasses, which are used for a long period.

[0048] The photochromic compound whose skeleton is represented by formula (1) will be explained in detail below. Chemical Formula 9 Petition 870250084631, dated 09 / 19 / 2025, page 15 / 223 11 / 180 <m>

[0049] In formula (1), M is C, Si or Ge. Preferably, M is C. Ring A and Ring B

[0050] In formula (1), ring A and ring B are each independently a substituted or unsubstituted aromatic ring, a substituted or unsubstituted aromatic heterocyclic ring, or a substituted or unsubstituted fused polycyclic ring in which an aromatic ring or an aromatic heterocyclic ring is fused with these rings.

[0051] Examples of aromatic hydrocarbon rings include a benzene ring, a cyclotetradecaheptaene ring, and the like.

[0052] Examples of aromatic heterocyclic rings include a furan ring, a thiophene ring, a pyridine ring, and the like.

[0053] Examples of the fused polycyclic ring include a naphthalene ring, a fluorene ring, an anthracene ring, a phenanthrene ring, a tetracene ring, a pentacene ring, a benzopyrene ring, a chrysene ring, a pyrene ring, a triphenylene ring, a perylene ring, a benzofuran ring, a benzothiophene ring, a quinoline ring, an isoquinoline ring, an indole ring, a pyrimidine ring, a quinazoline ring, a pyridazine ring, a cinoline ring, a phthalazine ring, a 1,2,3-, 1,2,4- or 1,3,5-triazine ring, a carbazole ring, a benzoxazole ring, an isothiazole ring and the like.

[0054] Above all, a benzene ring, a naphthalene ring, a fluorene ring, a phenanthrene ring, a pyrene ring, a furan ring, a thiophene ring or a pyridine ring are preferred, a benzene ring, a naphthalene ring, a fluorene ring or a phenanthrene ring are most preferred, and a benzene ring is the most preferred. <r3>

[0055] In formula (1), R3 is an aryl or heteroaryl group replaced by a group represented by formula (1a) below. The dashed line Petition 870250084631, dated 09 / 19 / 2025, p. 16 / 223 12 / 180 jada indicates a hand attached to a carbon atom of the aryl or heteroaryl group. R3 is preferably an aryl group substituted by a group represented by formula (1a) below, more preferably a phenyl group substituted by a group represented by formula (1a) below. Chemical Formula 10 p1x'N'' (1a) I (R)

[0056] R1 is a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted fused polycyclic ring in which an aromatic ring or an aromatic heterocyclic ring is fused with these substituents. The substituent that may be included in a group that may be R1 will be described later.

[0057] The number of carbon atoms in the substituted or unsubstituted aryl group is, for example, 5 or more and 12 or less, and preferably 6 or more and 10 or less. The heteroatom of the substituted or unsubstituted heteroaryl group is at least one selected from a group consisting of an oxygen atom, a sulfur atom, a nitrogen atom, and a phosphorus atom. The number of heteroatoms in the substituted or unsubstituted heteroaryl group is, for example, 1 or more and 3 or less, and preferably 1 or 2. The number of carbon atoms in the substituted or unsubstituted heteroaryl group is, for example, 4 or more and 11 or less, and preferably 5 or more and 9 or less.

[0058] R1 is preferably a substituted or unsubstituted phenyl group, a substituted or unsubstituted 1-naphthyl group, a substituted or unsubstituted 2-naphthyl group, a substituted tienyl group Petition 870250084631, dated 09 / 19 / 2025, p. 17 / 223 13 / 180 or unsubstituted, a substituted or unsubstituted furyl group, a substituted or unsubstituted pyrrolinyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted benzofuranyl group or a substituted or unsubstituted benzopyrrolinyl group, more preferably a substituted or unsubstituted phenyl group, a substituted or unsubstituted 1-naphthyl group or a substituted or unsubstituted 2-naphthyl group, particularly preferably, in terms of ease of production, a substituted or unsubstituted phenyl group.

[0059] The substituent that can be included in group R1 will be described in detail later. The substituent that can be included in group R1 is preferably at least one selected from a group consisting of a linear or branched alkyl group with 1 or more and 6 or fewer carbon atoms, a linear or branched haloalkyl group with 1 or more and 6 or fewer carbon atoms, a linear or branched alkoxy group with 1 or more and 6 or fewer carbon atoms and a halogen atom. The number of substituents is, for example, 1 or more and 3 or fewer. (R2)

[0060] R2 is a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted haloalkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted aralkyl group or a group represented by formula (2a) below.

[0061] R2 is preferably a halogen atom, a group Petition 870250084631, dated 09 / 19 / 2025, p. 18 / 223 14 / 180 substituted or unsubstituted alkyl, a substituted or unsubstituted haloalkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted aryloxyl group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted aralkyl group or a group represented by formula (2a) below.

[0062] From the point of view of increasing the color fading rate, R2 is more preferably a substituted or unsubstituted alkyl group, a substituted or unsubstituted haloalkyl group, a substituted or unsubstituted cycloalkyl group or a group represented by formula (2a) below.

[0063] The halogen atom is preferably a fluorine atom or a chlorine atom.

[0064] The alkyl group is preferably an unsubstituted alkyl group with 1 to 20 carbon atoms, more preferably an unsubstituted alkyl group with 1 to 10 carbon atoms. Specific examples of the alkyl group include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, and a hexyl group.

[0065] Preferably, the haloalkyl group has from 1 to 20 carbon atoms. The number of halogen atoms is preferably from 1 to 20, more preferably from 2 to 10. The haloalkyl group with 1 to 20 carbon atoms is preferably an alkyl group substituted with a fluorine atom, a chlorine atom, or a bromine atom. Preferably, the haloalkyl group has a perfluoromethyl group at its terminal end. Examples of a suitable haloalkyl group include a trifluoromethyl group, a trifluoroethyl group, a trifluoropropyl group, a tetrafluoroethyl group, a chloromethyl group, a 2-chloroethyl group, a bromomethyl group, and similar groups. Petition 870250084631, dated 09 / 19 / 2025, page 19 / 223 15 / 180 households.

[0066] The cycloalkyl group is preferably a cycloalkyl group with 3 to 10 carbon atoms (cycloalkyl group with 3 to 8 carbon atoms forming a ring). Examples of cycloalkyl groups with 3 to 10 carbon atoms include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and the like. Note that although the cycloalkyl group may have substituents, the number of carbon atoms (3 to 10 carbon atoms) does not include the number of carbon atoms in the substituents.

[0067] The alkoxy group is preferably an alkoxy group with 1 to 6 carbon atoms. Examples of a suitable alkoxy group with 1 to 6 carbon atoms include a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, a sec-butoxy group, a tert-butoxy group, and the like.

[0068] Preferably, the aryloxy group has 6 to 12 carbon atoms. Examples of aryloxy groups with 6 to 12 carbon atoms include a phenyloxy group, a naphthyloxy group, and the like.

[0069] Preferably, the alkylthio group has from 1 to 6 carbon atoms. Examples of alkylthio groups with 1 to 6 carbon atoms include a methylthio group, an ethylthio group, an n-propylthio group, an isopropylthio group, an n-butylthio group, a sec-butylthio group, a t-butylthio group, and the like.

[0070] Preferably, the arylthio group has 6 to 10 carbon atoms. Examples of arylthio groups with 6 to 10 carbon atoms include a phenylthio group, a 1-naphthylthio group, a 2-naphthylthio group, and the like.

[0071] Preferably, the aralkyl group has from 7 to 11 carbon atoms. Examples of aralkyl groups with 7 to 11 carbon atoms include a benzyl group, a phenylethyl group, a phenylpropyl group, a phenylbutyl group, a naphthylmethyl group, and the like. Petition 870250084631, dated 09 / 19 / 2025, p. 20 / 223 16 / 180

[0072] The substituent that can be included in group R2 will be described in detail later. The substituent that can be included in group R2 is preferably at least one selected from a group consisting of a linear or branched alkyl group with 1 or more and 6 or fewer carbon atoms, a linear or branched haloalkyl group with 1 or more and 6 or fewer carbon atoms, a linear or branched alkoxy group with 1 or more and 6 or fewer carbon atoms, a cycloalkyl group with 4 or more and 8 or fewer carbon atoms and a halogen atom. The number of substituents is, for example, 1 or more and 3 or fewer.

[0073] R2 is preferably an alkyl group with 1 to 20 carbon atoms, a haloalkyl group with 1 to 20 carbon atoms, an alkoxy group with 1 to 10 carbon atoms, an alkoxyalkyl group with 1 to 10 carbon atoms, a cycloalkyl group with 3 to 10 carbon atoms or a fluorine atom, more preferably an alkyl group with 1 to 10 carbon atoms, a haloalkyl group with 1 to 10 carbon atoms or a cycloalkyl group with 5 to 8 carbon atoms. The haloalkyl group with 1 to 10 carbon atoms is preferably a fluoroalkyl group, particularly preferably a fluoroalkyl group with a perfluoromethyl group at its terminal end. (Group represented by formula (2a)) -Q1-(X1Q2)a-X2Q3(2a)

[0074] In formula (2a), Q1 is an alkylene group or a haloalkylene group.

[0075] The number of carbon atoms in the alkylene group is preferably 1 or more and 20 or less, more preferably 1 or more and 12 or less, even more preferably 1 or more and 7 or less, and even more preferably 2 or more and 6 or less. As a halogen atom in the haloalkylene group, it can be used by Petition 870250084631, dated 09 / 19 / 2025, p. 21 / 223 17 / 180 minus one selected from a group consisting of I, Cl, Br, and F. The halogen atom is preferably at least one of Cl and F, more preferably F. In the haloalkylene group, it is preferable that the halogen atom be bonded to the terminal carbon atom, and it is even more preferable that the terminal group be a perfluoromethyl group.

[0076] Q2 is an alkylene group or a haloalkylene group. The preferred aspect of the alkylene group or haloalkylene group is the same as described for Q1. The number of carbon atoms in the alkylene group or haloalkylene group of Q2 may be the same as or different from that in the alkylene group or haloalkylene group of Q1.

[0077] Q3 is an alkyl group or a haloalkyl group, which may be linear or branched, but is preferably linear.

[0078] The number of carbons in the alkyl group is preferably 1 or more and 20 or less, more preferably 1 or more and 12 or less, and even more preferably 1 or more and 7 or less. As a halogen atom of the haloalkyl group, at least one can be selected from a group consisting of I, Cl, Br, and F. The halogen atom is preferably at least one of Cl and F, more preferably F.

[0079] Q3 is preferably a linear alkyl group.

[0080] X1 and X2 are each independently O, S, NR700, PR701 or P(=O). X1 and X2 are preferably O, S or NR700, most preferably O.

[0081] R700e R701 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[0082] R700 is preferably a hydrogen atom, a group Petition 870250084631, dated 09 / 19 / 2025, p. 22 / 223 18 / 180 substituted or unsubstituted alkyl, or a substituted or unsubstituted aryl group. The alkyl group is preferably a methyl group, an ethyl group, a propyl group, a butyl group or a pentyl group. The aryl group is preferably a phenyl group or a naphthyl group.

[0083] R701 is preferably a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. The alkyl group is preferably a methyl group, an ethyl group, a propyl group, a butyl group or a pentyl group. The aryl group is preferably a phenyl group or a naphthyl group.

[0084] a is an integer of 0, or 1 or more and 3 or less.

[0085] Formula (2a) is preferably an alkylene alkoxy group, an alkylene thioalkyl group or an alkylene oxyalkylene alkoxy group.

[0086] Specific examples of formula (2a) include -CH2OCH3, -ch2sch3, -CH2CH2OCH3, -CH2CH2OCH2CH3, -CH2CH2SCH3, -CH2CH2CH2OCH3, -CH2CH2CH2SCH3, -CH2CH2OCH2CH2OCH3, and-CH2CH2OCH2CH2OCH2CH3.

[0087] The group represented by formula (2a) is preferably -CH2OCH3,-CH2CH2OCH3,-CH2CH2OCH2CH3,-CH2CH2CH2OCH3, -CH2CH2OCH2CH2OCH3, or -CH2CH2OCH2CH2OCH2CH3. Specific example of formula (1a)

[0088] Examples of suitable formula (1a) are as follows. Chemical Formula 11 Petition 870250084631, dated 09 / 19 / 2025, page 23 / 223 19 / 180 <r4>

[0089] In formula (1), R4 is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group.

[0090] The number of carbon atoms in the substituted or unsubstituted aryl group is, for example, 5 or more and 12 or less, and preferably 6 or more and 10 or less. The heteroatom of the substituted or unsubstituted heteroaryl group is at least one selected from a group consisting of an oxygen atom, a sulfur atom, a nitrogen atom, and a phosphorus atom. The number of heteroatoms in the substituted or unsubstituted heteroaryl group is, for example, 1 or more and 3 or less, and preferably 1 or 2. The number of carbon atoms in the substituted or unsubstituted heteroaryl group is, for example, 4 or more and 11 or less, and preferably 5 or more and 9 or less.

[0091] R4 is preferably a substituted or unsubstituted phenyl group, a substituted or unsubstituted 1-naphthyl group, a substituted or unsubstituted 2-naphthyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted furyl group, a substituted or unsubstituted pyrrolinyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted benzofuranyl group, or a substituted or unsubstituted benzopyrrolinyl group, more preferably a substituted or unsubstituted phenyl group, a group Petition 870250084631, dated 09 / 19 / 2025, p. 24 / 223 20 / 180 1-naphthyl substituted or unsubstituted or a 2-naphthyl substituted or unsubstituted group, particularly preferably a substituted phenyl group. Skeleton represented by formula (2)

[0092] Preferably, the photochromic compound according to the embodiment has a naphthopyran skeleton represented by formula (2) below. In formula (2) below, M, R3, and R4 are each the same as those in formula (1). Chemical Formula 12 (2) Skeleton represented by formula (3)

[0093] Preferably, the photochromic compound according to the modality has a skeleton represented by formula (3) below. In formula (3) below, M, R3 and R4 are each the same as those in formula (1). Chemical Formula 13 (3)<R5e R6>

[0094] R5 and R6 are each independently a hydrogen atom, a hydroxyl group, a substituted or unsubstituted alkyl group Petition 870250084631, dated 09 / 19 / 2025, page 25 / 223 21 / 180 tuído, a haloalkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted heterocyclic group, a cyano group, a halogen atom, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a nitro group, a formyl group, a hydroxycarbonyl group, a substituted or unsubstituted alkylcarbonyl group, a substituted or unsubstituted alkoxycarbonyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aralkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a thiol group, a substituted or unsubstituted alkoxyalkylthio group, a haloalkylthio group, a substituted or unsubstituted cycloalkylthio group,a substituted or unsubstituted silyl group, a substituted or unsubstituted oxysyl group, a group represented by formula (2a) above, a group represented by formula (X) below, or a group represented by formula (X3) below.

[0095] The same groups listed for R1 or R2 as examples can be used as the substituted or unsubstituted alkyl group, the haloalkyl group, the group represented by formula (2a), the substituted or unsubstituted cycloalkyl group, the substituted or unsubstituted alkoxy group, the halogen atom, the substituted or unsubstituted alkylthio group, the substituted or unsubstituted aryloxy group, the substituted or unsubstituted arylthio group, the substituted or unsubstituted aralkyl group, the substituted or unsubstituted aryl group and the substituted or unsubstituted heteroaryl group.

[0096] The amino group can be a primary amino group (-NH2) or a secondary or tertiary amino group with substituents that have been replaced by one or two hydrogen atoms. The amino group Petition 870250084631, dated 09 / 19 / 2025, p. 26 / 223 22 / 180 may be the group represented by formula (1a) above. Examples of substituents on the substituted amino group include an alkyl group with 1 to 6 carbon atoms, a haloalkyl group with 1 to 6 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, a cycloalkyl group with 3 to 7 carbon atoms, an aryl group with 6 to 14 carbon atoms, a heteroaryl group with 4 to 14 carbon atoms, and the like. Examples of a suitable amino group include an amino group, a methylamino group, a dimethylamino group, an ethylamino group, a diethylamino group, a methylphenylamino group, a diphenylamino group, and the like.

[0097] Preferably, the heterocyclic group consists of 3 to 10 atoms. The heteroatom of the heterocyclic group is preferably at least one selected from a group consisting of an oxygen atom, a nitrogen atom, a sulfur atom, and a phosphorus atom. The number of heteroatoms is, for example, 1 or more and 5 or less, and preferably 1 or 2. Specific examples of the heterocyclic group include an aliphatic heterocyclic group, such as a morpholino group, a piperidine group, a pyrrolidinyl group, a piperazine group, and an N-methylpiperazine group, and an aromatic heterocyclic group, such as an indolinyl group. The heterocyclic group may also be a 2,6-dimethylmorpholino group, a 2,6-dimethylpiperidine group, and a 2,2,6,6-tetramethylpiperidine group.

[0098] Preferably, the alkylcarbonyl group has from 2 to 7 carbon atoms. Examples of alkylcarbonyl groups with 2 to 7 carbon atoms include an acetyl group and an ethylcarbonyl group.

[0099] Preferably, the alkoxycarbonyl group has from 2 to 7 carbon atoms. Examples of alkoxycarbonyl groups with 2 to 7 carbon atoms include a methoxycarbonyl group and an ethoxycarbonyl group.

[00100] Preferably, the aralkoxy group has 7 to 11 atoms Petition 870250084631, dated 09 / 19 / 2025, p. 27 / 223 23 / 180 carbon. Examples of the aralkoxy group with 7 to 11 carbon atoms include a benzyloxy group, a naphthylmethoxy group, and the like.

[00101] Preferably, the alkoxyalkylthio group has from 2 to 9 carbon atoms. Examples of the alkoxyalkylthio group with 2 to 9 carbon atoms include a methoxymethylthio group, a methoxyethylthio group, a methoxy-n-propylthio group, a methoxy-n-butylthio group, an ethoxyethylthio group, an n-propoxypropylthio group, and the like.

[00102] Preferably, the haloalkylthio group has from 1 to 6 carbon atoms. Examples of haloalkylthio groups with 1 to 6 carbon atoms include a trifluoromethylthio group, a tetrafluoroethylthio group, a chloromethylthio group, a 2-chloroethylthio group, a bromomethylthio group, and the like.

[00103] Preferably, the cycloalkyl group has from 3 to 8 carbon atoms. Examples of cycloalkylthio groups with 3 to 8 carbon atoms include a cyclopropylthio group, a cyclobutylthio group, a cyclopentylthio group, a cyclohexylthio group, and the like. Note that although the cycloalkyl group may have substituents, the number of carbon atoms (3 to 8 carbon atoms) does not include the number of carbon atoms in the substituents.

[00104] The silyl group may have substituents. Examples of substituents for the substituted silyl group include, but are not particularly limited to, an alkyl group with 1 to 6 carbon atoms, a haloalkyl group with 1 to 6 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, a cycloalkyl group with 3 to 7 carbon atoms, an aryl group with 6 to 14 carbon atoms, a heteroaryl group with 4 to 14 carbon atoms, and the like.

[00105] The oxysyl group may have substituents. Examples of substituents for the substituted oxysyl group include, but are not particularly limited to, an alkyl group with 1 to 6 carbon atoms, a haloalkyl group with 1 to 6 carbon atoms, an alkoxy group Petition 870250084631, dated 09 / 19 / 2025, p. 28 / 223 24 / 180 with 1 to 6 carbon atoms, a cycloalkyl group with 3 to 7 carbon atoms, an aryl group with 6 to 14 carbon atoms, a heteroaryl group with 4 to 14 carbon atoms, and the like.

[00106] The cycloalkyl group, the arylthio group, the aralkyl group, the aralkoxy group, the aryloxy group, the aryl group, the heteroaryl group, and the cycloalkylthio group may be unsubstituted. However, when these groups have substituents, it is preferable that 1 to 8 hydrogen atoms, particularly preferably 1 to 4 hydrogen atoms in the ring-forming groups, be substituted by substituents selected from a hydroxy group, an alkyl group with 1 to 6 carbon atoms, a haloalkyl group with 1 to 6 carbon atoms, a cycloalkyl group with 3 to 8 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, an amino group, a substituted amino group, a heterocyclic group consisting of 3 to 8 atoms, a cyano group, a nitro group, and a halogen atom.

[00107] R5 and R6 may be a hydrogen atom, a substituted or unsubstituted alkyl group, a haloalkyl group, a group represented by formula (2a), a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a hydroxycarbonyl group, a substituted or unsubstituted alkylcarbonyl group, a substituted or unsubstituted alkoxycarbonyl group, a halogen atom, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aralkoxy group, a substituted or unsubstituted aryl oxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group or formula (X3) below.

[00108] R5 and R6, together with M, may collectively constitute a substituted or unsubstituted aliphatic ring with 3 to 20 carbon atoms, a substituted or unsubstituted fused polycyclic ring in which an aromatic hydrocarbon ring or a heterocyclic ring Petition 870250084631, dated 09 / 19 / 2025, page 29 / 223 25 / 180 aromatic is fused with an aliphatic ring, a substituted or unsubstituted heterocyclic ring with 3 to 20 atoms, or a substituted or unsubstituted fused polycyclic ring. ringin in which an aromatic ring or an aromatic heterocyclic ring is fused with a heterocyclic ring.

[00109] R5 and R6 preferably constitute a substituted or unsubstituted aliphatic ring having from 3 to 20 carbon atoms in its members, a substituted or unsubstituted fused polycyclic ring in which an aromatic hydrocarbon ring or an aromatic heterocyclic ring is fused with an aliphatic ring, a substituted or unsubstituted heterocyclic ring having from 3 to 20 atoms in its members, more preferably constitute, together with M, a ring selected from a cyclopentane ring, a cyclohexane ring, a cycloheptane ring, a cyclooctane ring, a cyclononane ring, a cyclodecane ring, a cycloundecane ring, a cyclododecane ring and a spirocyclohydrocyclohexane ring. The ring may have from 1 to 10 alkyl groups with 1 to 5 carbon atoms or cycloalkyl groups with 5 to 7 carbon atoms as substituents, and a cycloalkyl group with 5 to 7 carbon atoms may be fused.Specifically, it is preferable that rings represented by the formulas below be formed. Chemical Formula 14

[00110] Substituents that can be included in the R5e groups Petition 870250084631, dated 09 / 19 / 2025, page 30 / 223 26 / 180 R6s will be described in detail later. A substituent that can be included in this group is preferably a linear or branched alkyl group with 1 or more and 6 or fewer carbon atoms. Group Represented by Formula (X) Chemical Formula 15 g

[00111] In formula (X), E is an oxygen atom or NR101. R101 is a hydrogen atom or an alkyl group. E is NR101, and R101 is preferably a hydrogen atom or an alkyl group with 1 to 6 carbon atoms.

[00112] F is either an oxygen atom or a sulfur atom. F is preferably an oxygen atom.

[00113] G is an oxygen atom, a sulfur atom or NR2O2. R2O2 is a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a heteroaryl group. G is preferably NH.

[00114] géOoul.

[00115] R201 is a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a heteroaryl group. When G is an oxygen atom or a sulfur atom, R201 is a group other than a hydrogen atom. R201 is preferably an alkyl group with 1 to 6 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, or an aryl group with 6 to 12 carbon atoms.

[00116] The appropriate groups represented by formula (X) are as follows. Chemical Formula 16 Petition 870250084631, dated 09 / 19 / 2025, p. 31 / 223 27 / 180 Group represented by the formula (X3)

[00117] L1-R400(X3)

[00118] In formula (X3), R400 is a hydrogen atom, an alkyl group, an aryl group, a polymerizable group, a photochromic group, or a silyl group having, as a substituent, an alkyl group, an alkoxy group, or an aryl group.

[00119] L1 is a group represented by the formula (X2) below. Chemical Formula 17

[00120] In formula (X2), R30 is a group represented by formula (X2a) below. Chemical Formula 18

[00121] In formula (X2) and in formula (X2a), J represents a divalent group. A plurality of J groups is, each independent. Petition 870250084631, dated 19 / 09 / 2025, p. 32 / 223 28 / 180 naturally, directly linked to a substituted or unsubstituted methylene group, to an oxygen atom, to a sulfur atom or to a hydrogen atom or an alkyl group. NR301· R301 is preferably an alkyl group with 1 to 20 carbon atoms. Preferably, this alkyl group has, as a substituent, a silyl group with an alkyl group with 1 to 10 carbon atoms, a polymerizable group or a photochromic group.

[00122] Examples of the polymerizable group include radically polymerizable groups, such as a vinyl group, a 1-chlorovinyl group, an allyl group, a styryl group, a (meth)acrylic group, a 2-(methacryloxy)ethylcarbamyl group, a 2-(methacryloxy)ethoxycarbonyl group, and a crotyl group. Other examples include an epoxy group, an episulfide group, a thietanyl group, an OH group, an SH group, an NH2 group, a COOH group, an NCO group, an NCS group, or similar groups. The polymerizable group is preferably at least one selected from a group consisting of a (meth)acrylic group, a 2-(methacryloxy)ethylcarbamyl group, a 2-(methacryloxy)ethoxycarbonyl group, an epoxy group, an OH group, an SH group, an NH2 group, and a COOH group.

[00123] The photochromic group includes a photochromic site. Representative examples of the photochromic group include naphthopyran, spirooxazine, spiropyran, fulgide, fulgimide, and diaryletene. As a photochromic group, indenonaphthopyran is preferable because it can express excellent photochromic properties, and above all, indeno[2,1-f]naphtho[1,2-b]pyran is particularly preferable.

[00124] Indeno [2,1-f] naphtho [1,2-b]pyran is preferably a group represented by formula (X4) below. Petition 870250084631, dated 09 / 19 / 2025, page 33 / 223 29 / 180 Chemical Formula 19

[00125] In formula (X4), R401 and R402 can be the same groups used for R5 and R6 described above.

[00126] R403 and R404 can each independently be the same groups used for R5 and R6 described above.

[00127] R405 and R406 are each independently either a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. R405 and R406 may be the same groups used for R4 described above.

[00128] In formula (X4), o is an integer from 0 to 4.

[00129] n is an integer from 0 to 4. When it is from 2 to 4, a plurality of groups R403 can be the same or different from each other. When n is from 2 to 4, a plurality of groups R404 can be the same or different from each other.

[00130] At least one of the substituents on the aryl or heteroaryl group of R401, R402, R403, R404 and R405 is linked to L1.

[00131] A particularly suitable group represented by formula (X2) is represented by the formulas below. Petition 870250084631, dated 09 / 19 / 2025, p. 34 / 223 30 / 180 Chemical Formula 20

[00132] In formula (X2) and formula (X2a), L is an oxygen atom or a sulfur atom.

[00133] R300 is an alkylene group or a silylene group with an alkyl group or an aryl group as a substituent. R300 is preferably a silylene group with an alkylene group with 1 to 6 carbon atoms, or a silylene group with an alkyl group with 1 to 6 carbon atoms as a substituent.

[00134] R302, R303 and R304 are each independently an alkylene group. R302 is preferably an alkylene group with 1 to 6 carbon atoms. R303 is preferably an alkylene group with 1 to 6 carbon atoms. R304 is preferably an alkylene group with 1 to 6 carbon atoms.

[00135] h, j, k and I are each independently an integer of 0 or 1.

[00136] In the formula (X2a), i is an integer from 1 to 200. When Petition 870250084631, dated 09 / 19 / 2025, p. 35 / 223 31 / 180 i is 2 or more, the structures of a plurality of R30 can be the same or different from each other.

[00137] i is preferably a numeric number within a range of 5 to 100, more preferably from 8 to 75, most preferably from 10 to 70.

[00138] Dashed lines indicate titles with R400. Photochromic compound represented by formula (4)

[00139] The photochromic compound according to the modality is preferably a compound represented by formula (4) below. Chemical Formula 21

[00140] In formula (4), R3, R4, R5, R6 and M are each the same as those in formula (3). <R7e R8>

[00141] R7 and R8 are each independently a hydroxy group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted haloalkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted haloalkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted heterocyclic group, a cyano group, a halogen atom, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a nitro group, a formyl group, a hydroxycarbonyl group, a substituted or unsubstituted alkylcarbonyl group, a group Petition 870250084631, dated 09 / 19 / 2025, page 36 / 223 32 / 180 substituted or unsubstituted alkoxycarbonyl, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aralkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a thiol group, a substituted or unsubstituted alkoxyalkylthio group, a haloalkylthio group, a substituted or unsubstituted cycloalkylthio group, a substituted or unsubstituted silyl group, a substituted or unsubstituted oxysilyl group, a group represented by formula (2a) above, a group represented by formula (X) above or a group represented by formula (X3) above. As groups, the same groups listed for R1a R6 can be used as examples.

[00142] b is an integer from 0 to 4 and c is an integer from 0 to 4, when b is from 2 to 4, a plurality of R7 groups may be the same or different from each other, when c is from 2 to 4, a plurality of R8 groups may be the same or different from each other, when b is from 2 to 4 and there are R7 groups adjacent to each other, the two adjacent R7 groups, together with carbon atoms to which the R7 groups are attached, may collectively constitute a substituted or unsubstituted aliphatic ring, a substituted or unsubstituted aliphatic heterocyclic ring, a substituted or unsubstituted aromatic ring, a substituted or unsubstituted aromatic heterocyclic ring, or a substituted or unsubstituted fused polycyclic ring. ringin in which an aromatic ring or an aromatic heterocyclic ring is fused with these rings. The adjacent R7 groups combined are located at positions 5 and 6, 6 and 7, or 7 and 8 of the chromene compound.

[00143] When c varies from 2 to 4, a plurality of R8 groups may be the same or different from each other. When c varies from 2 to 4 and there are adjacent R8 groups, the two adjacent R8 groups, together with the atoms Petition 870250084631, dated 09 / 19 / 2025, p. 37 / 223 33 / 180 carbon atoms to which the R8 groups are attached may collectively constitute a substituted or unsubstituted aliphatic ring, a substituted or unsubstituted aliphatic heterocyclic ring, a substituted or unsubstituted aromatic ring, a substituted or unsubstituted aromatic heterocyclic ring, or a substituted or unsubstituted fused polycyclic ring. Ringine in which an aromatic ring or an aromatic heterocyclic ring is fused with these rings. The adjacent combined R8 groups are located at positions 9 and 10, 10 and 11, or 11 and 12 of the chromene compound.

[00144] R7 or R8 may form a ring made of 5 to 8 atoms, including carbon atoms to which R7 or R8 are attached. The ring may also have a substituent. The substituent includes a substituent selected from a hydroxyl group, an alkyl group with 1 to 6 carbon atoms, a haloalkyl group with 1 to 6 carbon atoms, a cycloalkyl group with 3 to 8 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, an amino group, a substituted amino group, a heterocyclic group with 3 to 8 atoms, a cyano group, a nitro group, and a halogen atom. Specific examples of these substituents will be described later.

[00145] A suitable ring is exemplified by a ring represented by formula (X5) below. Chemical Formula 22

[00146] In formula (X5), Q and T are each independently a sulfur atom, a substituted or unsubstituted methylene group, an oxygen atom, or a group represented by NR307.R307é Petition 870250084631, dated 09 / 19 / 2025, p. 38 / 223 34 / 180 a hydrogen atom, a hydroxy group, an alkyl group, a haloalkyl group, a cycloalkyl group, an alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group or a group represented by formula (2a).

[00147] Preferably, R305 and R306 are each independently a hydroxy group, an alkyl group, a haloalkyl group, a cycloalkyl group, an alkoxy group, an amino group, a substituted amino group, a substituted or unsubstituted heterocyclic group, a cyano group, a nitro group, a formyl group, a hydroxycarbonyl group, an alkylcarbonyl group, an alkoxycarbonyl group, a halogen atom, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aralkoxy group, a substituted or unsubstituted aryl group, a thiol group, an alkylthio group, an alkoxyalkylthio group, a haloalkylthio group, a cycloalkylthio group or a substituted or unsubstituted arylthio group.

[00148] R305 and R306 can form a substituted or unsubstituted aliphatic ring, together with carbon atoms to which R305 and R306 are attached. Specific examples of the aliphatic ring include a cyclopentane ring, a cyclohexane ring, and the like. In the aliphatic ring, 1 to 8 hydrogen atoms, particularly preferably 1 to 4 hydrogen atoms, can be substituted by at least one group selected from a group consisting of a hydroxyl group, an alkyl group, a haloalkyl group, a cycloalkyl group, an alkoxy group, an amino group, a substituted amino group, a heterocyclic group, a cyano group, a nitro group, and a halogen atom. Specific examples of these substituents will be described later.

[00149] In formula (X5), m is an integer from 1 to 4. Photochromic compound represented by formula (5)

[00150] A suitable chromene compound is exemplified by Petition 870250084631, dated 09 / 19 / 2025, page 39 / 223 35 / 180 a compound represented by formula (5) below. Chemical Formula 23 R3, R4, R5, R6, R7, R8, b and c are each independently the same as those in formula (4). Photochromic compound represented by formula (6)

[00152] A more preferable photochromic compound is exemplified by a compound represented by formula (6) below. Chemical Formula 24 exactly the same as those in formula (5). <r9a>

[00154] R9a is a group represented by formula (1a) above, a hydrogen atom, a hydroxyl group, an alkyl group having from 1 to 6 carbon atoms, a haloalkyl group having from 1 to 6 carbon atoms, a cycloalkyl group having from 3 to 8 carbon atoms, a Petition 870250084631, dated 09 / 19 / 2025, page 40 / 223 36 / 180 alkoxy group having from 1 to 6 carbon atoms, a substituted or unsubstituted amino group, a substituted or unsubstituted heterocyclic group, a cyano group, a halogen atom, an alkylthio group having from 1 to 6 carbon atoms, a substituted or unsubstituted arylthio group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted oxysilyl group, a group represented by formula (2a) above, or a group represented by formula (X3) above. As groups, the same groups listed for R1a R8 can be used as examples.

[00155] d1 represents the number of R9ae and is an integer from 1 to 5.

[00156] When d1 is 1, R9a is a group represented by formula (1a) above.

[00157] When d1 is from 2 to 5, at least one of a plurality of groups R9a is a group represented by formula (1a) above, and a plurality of groups R9a may be the same or different from each other.

[00158] When there are R9a groups adjacent to each other, except for the group represented by formula (1a) above, the two adjacent R9a groups, together with carbon atoms to which the R9a groups attach, may collectively constitute a substituted or unsubstituted aliphatic ring, a substituted or unsubstituted aliphatic heterocyclic ring, a substituted or unsubstituted aromatic ring, a substituted or unsubstituted aromatic heterocyclic ring, or a substituted or unsubstituted fused polycyclic ring. ringin in which an aromatic ring or an aromatic heterocyclic ring is fused with these rings. Two R9a groups adjacent to each other may collectively constitute a ring group that may include at least one selected from a group consisting of an oxygen atom, an en atom Petition 870250084631, dated 09 / 19 / 2025, p. 41 / 223 37 / 180 sulfur, a carbon atom, and a nitrogen atom. This ring group is preferably, but not particularly limited to, a ring consisting of 5 to 8 atoms, including carbon atoms to which the R9 groups are attached. The ring may also have a substituent. Examples of the substituent include substituents selected from a hydroxyl group, an alkyl group with 1 to 6 carbon atoms, a haloalkyl group with 1 to 6 carbon atoms, a cycloalkyl group with 3 to 8 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, an amino group, a substituted amino group, a heterocyclic group consisting of 3 to 8 atoms, a cyano group, a nitro group, and a halogen atom. Specific examples of these substituents are the same as described above. As for the ring, it is preferable that the R9 groups collectively constitute a ring represented by formula (X5).However, as described above, the group represented by formula (1a) does not constitute the ring described above, even if there are other adjacent R9a groups. <r10a>

[00159] R10a is a hydroxy group, an alkyl group with 1 to 6 carbon atoms, a haloalkyl group with 1 to 6 carbon atoms, a cycloalkyl group with 3 to 8 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, a substituted or unsubstituted amino group, a substituted or unsubstituted heterocyclic group, a cyano group, a halogen atom, an alkylthio group with 1 to 6 carbon atoms, a substituted or unsubstituted arylthio group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted oxysilyl group, a group represented by formula (2a) above, or a group represented by formula (X3) above. As groups, the same groups listed may be used Petition 870250084631, dated 09 / 19 / 2025, p. 42 / 223 38 / 180 for R1 to R8 as examples.

[00160] el represents the number of R10ae and is an integer from 0 to 5.

[00161] When e1 is 2 or greater, a plurality of groups R10a can be the same or different from each other.

[00162] When e1 is from 2 to 5 and there are R10a groups adjacent to each other, the two adjacent R10a groups, together with carbon atoms to which the R10a groups attach, can collectively constitute a substituted or unsubstituted aliphatic ring, a substituted or unsubstituted aliphatic heterocyclic ring, a substituted or unsubstituted aromatic ring, a substituted or unsubstituted aromatic heterocyclic ring, or a substituted or unsubstituted fused polycyclic ring. ringin in which an aromatic ring or an aromatic heterocyclic ring is fused with these rings.

[00163] Adjacent R10s may collectively constitute a ring group that may include at least one selected from a group consisting of an oxygen atom, a sulfur atom, a carbon atom, and a nitrogen atom. This ring group is preferably, but not particularly limited to, a ring consisting of 5 to 8 atoms, including carbon atoms to which the R10s groups attach. The ring may also have a substituent. Examples of the substituent include substituents selected from a hydroxy group, an alkyl group with 1 to 6 carbon atoms, a haloalkyl group with 1 to 6 carbon atoms, a cycloalkyl group with 3 to 8 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, an amino group, a substituted amino group, a heterocyclic group consisting of 3 to 8 atoms, a cyano group, a nitro group, and a halogen atom. Specific examples of these substituents are the same as described above.Regarding the ring, it is preferable that the R10 groups collectively constitute a ring represented by the formula (X5). Petition 870250084631, dated 09 / 19 / 2025, p. 43 / 223 39 / 180 Photochromic compound represented by formula (7)

[00164] A photochromic compound with superior color fade rate and repeat durability is exemplified by a compound represented by formula (7) below. Chemical Formula 25

[00165] In formula (7), R5, R6, R7, R8, R10a, b, c and e1 are each the same as those in formula (6), and R9 is a group represented by formula (1a) above. <r9b>

[00166] R9bé a hydroxy group, an alkyl group with 1 to 6 carbon atoms, a haloalkyl group with 1 to 6 carbon atoms, a cycloalkyl group with 3 to 8 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, a substituted or unsubstituted amino group, a substituted or unsubstituted heterocyclic group, a cyano group, a halogen atom, an alkylthio group with 1 to 6 carbon atoms, a substituted or unsubstituted arylthio group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted oxysilyl group, a group represented by formula (2a) above, or a group represented by formula (X3) above. As with these groups, the same list groups may be used Petition 870250084631, dated 09 / 19 / 2025, p. 44 / 223 40 / 180 of the values ​​for R1 to R8 as examples.

[00167] d2 represents the number of R9be and is an integer from 0 to 4.

[00168] When d2 is 2 or greater, a plurality of R9b groups can be the same or different from each other.

[00169] When d2 is from 2 to 4 and there are adjacent R9 groups, the two adjacent R9 groups, together with carbon atoms to which the R9 groups are attached, can collectively constitute a substituted or unsubstituted aliphatic ring, a substituted or unsubstituted aliphatic heterocyclic ring, a substituted or unsubstituted aromatic ring, a substituted or unsubstituted aromatic heterocyclic ring, or a fused polycyclic ring in which an aromatic ring or an aromatic heterocyclic ring is fused with these rings.

[00170] Two R9 groups adjacent to each other may collectively constitute a ring group which may include at least one selected from a group consisting of an oxygen atom, a sulfur atom, a carbon atom, and a nitrogen atom. This ring group is preferably, but not particularly limited to, a ring consisting of 5 to 8 atoms, including carbon atoms to which the R9 groups are attached. The ring may also have a substituent. Examples of the substituent include substituents selected from a hydroxy group, an alkyl group with 1 to 6 carbon atoms, a haloalkyl group with 1 to 6 carbon atoms, a cycloalkyl group with 3 to 8 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, an amino group, a substituted amino group, a heterocyclic group consisting of 3 to 8 atoms, a cyano group, a nitro group, and a halogen atom. Specific examples of these substituents are the same as described above.Regarding the ring, it is preferable that the R9b groups collectively constitute a ring represented by... Petition 870250084631, dated 09 / 19 / 2025, p. 45 / 223 41 / 180 formula (X5). Photochromic compound represented by formula (8)

[00171] A photochromic compound with a particularly excellent color fade rate and repeat durability is exemplified by a compound represented by formula (8) below. Chemical Formula 26 one the same as those in formula (7). <r10>

[00173] R10 is an alkyl group with 1 to 6 carbon atoms, a haloalkyl group with 1 to 6 carbon atoms, a cycloalkyl group with 3 to 8 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, a substituted or unsubstituted amino group, a substituted or unsubstituted heterocyclic group, a halogen atom, an alkylthio group with 1 to 6 carbon atoms, a substituted or unsubstituted arylthio group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted oxysilyl group, a group represented by formula (2a) above or a group represented by formula (X3) above. As groups, the same groups listed for R1a R8 can be used as examples. Petition 870250084631, dated 09 / 19 / 2025, p. 46 / 223 42 / 180 <r10b>

[00174] R10bé is a hydroxy group, an alkyl group with 1 to 6 carbon atoms, a haloalkyl group with 1 to 6 carbon atoms, a cycloalkyl group with 3 to 8 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, a substituted or unsubstituted amino group, a substituted or unsubstituted heterocyclic group, a cyano group, a halogen atom, an alkylthio group with 1 to 6 carbon atoms, a substituted or unsubstituted arylthio group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted oxysilyl group, a group represented by formula (2a) above, or a group represented by formula (X3) above. As groups, the same groups listed for R1a R8 can be used as examples.

[00175] e2 represents the number of R10be and is an integer from 0 to 4.

[00176] When e2 is 2 or greater, a plurality of R10b groups can be the same or different from each other.

[00177] When e2 is from 2 to 4 and there are adjacent R10 groups, the two adjacent R10 groups, together with carbon atoms to which the R10b groups are attached, can collectively constitute a substituted or unsubstituted aliphatic ring, a substituted or unsubstituted aliphatic heterocyclic ring, a substituted or unsubstituted aromatic ring, a substituted or unsubstituted aromatic heterocyclic ring, or a substituted or unsubstituted fused polycyclic ring in which an aromatic ring or an aromatic heterocyclic ring is fused with these rings.

[00178] Two R10 groups adjacent to each other may collectively constitute a ring group that may include at least one select Petition 870250084631, dated 09 / 19 / 2025, p. 47 / 223 43 / 180 consisting of a group consisting of an oxygen atom, a sulfur atom, a carbon atom, and a nitrogen atom. This ring group is preferably, but not particularly limited to, a ring consisting of 5 to 8 atoms, including carbon atoms to which the R10bse groups are attached. The ring may also have a substituent. Examples of the substituent include substituents selected from a hydroxyl group, an alkyl group with 1 to 6 carbon atoms, a haloalkyl group with 1 to 6 carbon atoms, a cycloalkyl group with 3 to 8 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, an amino group, a substituted amino group, a heterocyclic group consisting of 3 to 8 atoms, a cyano group, a nitro group, and a halogen atom. Specific examples of these substituents are the same as described above. As for the ring, it is preferable that the R10bse groups collectively constitute a ring represented by formula (X5). Detailed description of the substitutes, etc.

[00179] Examples of substituents that can be included in the R1a R10b groups described above include a hydroxy group, a cyano group, a halogen atom, a nitro group, a formyl group, a hydroxycarbonyl group, a thiol group, a group represented by formula (2a), a group represented by formula (X), a group represented by formula (X3), an alkyl group, a haloalkyl group, a cycloalkyl group, an alkoxy group, an amino group, a substituted amino group, a heterocyclic group, a halogen atom, an alkylthio group, an arylthio group, an alkylcarbonyl group, an alkoxycarbonyl group, an aralkyl group, an aralkoxy group, an aryloxy group, an aryl group, a heteroaryl group, an alkoxyalkylthio group, a haloalkylthio group, a cycloalkylthio group, a silyl group and an oxysilyl group. Like these groups, the same groups described in detail for R1 to R8 can be used. Petition 870250084631, dated 09 / 19 / 2025, page 48 / 223 44 / 180 Specific examples of suitable photochromic compounds

[00180] A particularly suitable photochromic compound is specifically exemplified by photochromic compounds represented by the following formulas. Chemical Formula 27 MeO OMe OMe F OMe OMe OMe THE OMe OMe OMe OMe MeO OMe CF3 OMe OMe OMe OMe OMe OMe OMe OMe Propargyl alcohol compound

[00181] The propargyl alcohol compound, according to the embodiment, has a skeleton represented by formula (9) below. This propargyl alcohol compound can be used as an intermediate to synthesize the photochromic compounds with the skeleton represented by formulas (1), (2), (3), (4) and (5) above. Petition 870250084631, dated 09 / 19 / 2025, page 49 / 223 45 / 180 Chemical Formula 28

[00182] In formula (9), R3 and R4 are each independently the same as those in formula (1) above.

[00183] Propargyl alcohol compound represented by formula (10)

[00184] The propargyl alcohol compound represented by formula (10) can be used as an intermediate to synthesize the photochromic compound represented by formula (6) above. Chemical Formula 29 (10)

[00185] In formula (10), R9a, R10a, d1 and e1 are each independently the same as those in formula (6) above. The propargyl alcohol compound represented by formula (11)

[00186] The propargyl alcohol compound represented by formula (11) can be used as an intermediate to synthesize the photochromic compound represented by formula (7) above. Chemical Formula 30 (11) r9

[00187] In formula (10), R10a, R9, R9b, e1 and d2 are each independently the same as those in formula (7) above. Propargyl alcohol compound represented by formula (12) Petition 870250084631, dated 09 / 19 / 2025, page 50 / 223 46 / 180

[00188] The propargyl alcohol compound represented by formula (12) can be used as an intermediate to synthesize the photochromic compound represented by formula (8) above. Chemical Formula 31

[00189] In formula (10), R9, R9b, R10, R10b, d2 and e2 are each independently the same as those in formula (8) above. Specific examples of naphthol derivatives

[00190] Specific examples of naphthol derivatives according to the embodiment include compounds represented by the following formulas. Chemical Formula 32 OMe Petition 870250084631, dated 09 / 19 / 2025, p. 51 / 223 47 / 180 Method for Producing Photochromic Compound

[00191] The photochromic compound, according to the embodiment, can be produced by any synthetic method. A representative example of the method for producing the photochromic compound will be explained, but the present invention is not limited to this method. Note that, in the following description, unless otherwise specified, the symbols in each formula have the same meanings explained for the formulas described above.

[00192] The photochromic compound can be produced by a reaction method of a naphthol derivative represented by formula (13) below with a propargyl alcohol compound represented by formula (9) below in the presence of an acid catalyst. Chemical Formula 33 OH (13) Chemical Formula 34

[00193] The reaction ratio of the naphthol compound and the propargyl alcohol compound is preferably selected in a range of 1:10 to 10:1 (molar ratio). For example, sulfuric acid, benzenesulfonic acid, ptoluenesulfonic acid, acid alumina, and similar substances are used as acid catalysts. The acid catalyst is preferably used in a range of 0.1 to 10 parts by weight per 100 parts by weight of the sum of the naphthol compound and the propargyl alcohol compound. Petition 870250084631, dated 09 / 19 / 2025, page 52 / 223 48 / 180 propargyl alcohol. The reaction temperature is preferably from 0 to 200°C. As a solvent, it is preferable to use an aprotic organic solvent, such as N-methylpyrrolidone, dimethylformamide, tetrahydrofuran, benzene, and toluene. A method for purifying a product obtained by this reaction is not particularly limited. For example, the product can be purified by a silica gel column followed by recrystallization. Method for synthesizing naphthol derivative

[00194] The naphthol derivative can be synthesized, for example, based on the reaction methods described in Non-Patented Document 1, Non-Patented Document 2, Patent Document 3 and other articles. As an example, a method for synthesizing a naphthol derivative represented by formula (14) below is not particularly limited, but, for example, when M is a carbon atom, the naphthol derivative can be synthesized as follows. Note that, in formula (14), R5, R6, R7, R8, b and c are the same as in formula (4) above. Chemical Formula 35

[00195] First, a benzophenone compound represented by formula (15) below is synthesized by the reaction of a benzene compound with an acid chloride using the Friedel-Crafts reaction. Petition 870250084631, dated 09 / 19 / 2025, p. 53 / 223 49 / 180 Chemical Formula 36

[00196] Note that, in formula (15), R7, R8, b and c are the same as in formula (4). Furthermore, the benzophenone compound represented by formula (15) undergoes a Stobbe reaction, a cyclization reaction, a hydrolysis reaction using an alkali or acid, protection with benzyl or a debenzylation by a hydrolysis reaction using an alkali or acid to obtain a carboxylic acid with a hydroxyl group protected by benzyl (Bn), represented by formula (16) below. Chemical Formula 37 (16)

[00197] Subsequently, the benzyl-protected carboxylic acid represented by formula (16) is converted into an amine by Curtius rearrangement, Hofmann rearrangement, Lossen rearrangement or similar, to prepare a diazonium salt from this amine. This diazonium salt is converted into a halide, such as a bromide or an iodide, by a Sandmeyer reaction or similar, to obtain a halide represented by formula (17) below (in the formula, Hal represents a halo). Petition 870250084631, dated 09 / 19 / 2025, page 54 / 223 50 / 180 genius). Chemical Formula 38 to prepare an organometallic reagent. This organometallic reagent reacts with a ketone represented by formula (18) below (in the formula, R5 and R6 are the same as in formula (4)) in an organic solvent at -100 to 70°C to obtain a compound represented by formula (19) below. Chemical Formula 39 reacted under neutral to acidic conditions, from 10 to 120°C, for 10 minutes to 2 hours, for the spironodilation of the alcohol, so that a derivative Petition 870250084631, dated 09 / 19 / 2025, p. 55 / 223 51 / 180 desired naphthol, represented by formula (14), can be synthesized. In this reaction, the reaction ratio between the organometallic reagent and the ketone, represented by formula (19), can be adopted from a wide range, but is preferably selected from 1:10 to 10:1 (molar ratio). The reaction temperature is preferably from -100 to 70°C. As a solvent, an aprotic organic solvent is preferably used, such as diethyl ether, tetrahydrofuran, benzene and toluene. The spiroannulation of the alcohol under neutral to acidic conditions is preferably carried out in the presence of an acid catalyst. As an acid catalyst, for example, acetic acid, hydrochloric acid, sulfuric acid, benzenesulfonic acid, ptoluenesulfonic acid and acidic alumina are used. Appropriately, this acid catalyst is used in a range of 0.1 to 10 parts by weight per 100 parts by weight of alcohol.Preferably, spiroannulation is carried out in the presence of a solvent such as tetrahydrofuran, benzene, or toluene. Method for synthesizing naphthol derivatives including Si and Ge

[00200] An example of a method for producing the naphthol derivative represented by formula (14) with M being Si or Ge will be explained below.

[00201] First, the halide represented by formula (17) reacts with magnesium, lithium or similar to prepare an organometallic reagent. This organometallic reagent reacts with a monohalide represented by formula (20) below (in the formula, R5 and R6 are the same as in formula (4)) at -100 to 70°C in an organic solvent to obtain a compound represented by formula (21) below. Petition 870250084631, dated 09 / 19 / 2025, page 56 / 223 52 / 180 Chemical Formula 41 by way of reference to the reaction methods described in Non-Patented Document 3, Non-Patented Document 4, Patented Document 4 and the like, to obtain a cyclized group represented by formula (22) below. Chemical Formula 43 OBn

[00203] The resulting cyclized group can be debenzylated to obtain the naphthol derivative represented by formula (14) above. Method for synthesizing propargyl alcohol compound

[00204] The propargyl alcohol compound can be synthesized by Petition 870250084631, dated 09 / 19 / 2025, page 57 / 223 53 / 180 example, based on the reaction methods described in Patent Document 5 and Patent Document 6. As an example, the propargyl alcohol compound represented by formula (11) above can be synthesized as follows: first, a benzene compound represented by formula (23) below reacts with an acid chloride compound represented by formula (24) below to obtain a benzophenone compound represented by formula (25) below (in the formula, R9 is the same as that of formula (1a) above). Chemical Formula 44 R9(25)

[00205] The benzophenone compound represented by formula (25) above can be synthesized by another method in which a benzophenone substituted with a halogen atom, as shown in formula (26) below (in the formula, Hal represents a halogen atom), is synthesized and then the halogen atom is substituted with an amino compound represented by formula (27) below. Petition 870250084631, dated 09 / 19 / 2025, page 58 / 223 54 / 180 Chemical Formula 47 (R10a)e1 Chemical Formula 48 R1'NH (27) I R2

[00206] The benzophenone compound obtained can be reacted with a metallic acetylene, such as sodium acetylide and lithium acetylide, or an acetylene derivative, such as Grignard acetylene, to synthesize the propargyl alcohol compound represented by formula (11) above.

[00207] Furthermore, the photochromic compound according to the present invention can be obtained by another method in which a propargyl alcohol represented by formula (28) below synthesized from the benzophenone compound represented by formula (26) above is reacted with the naphthol derivative represented by formula (14) above to synthesize a photochromic compound having a halogen atom represented by formula (29) below, and then the halogen atom is replaced by the amino compound represented by formula (27) above. Chemical Formula 49 (28) Petition 870250084631, dated 09 / 19 / 2025, page 59 / 223 55 / 180 Chemical Formula 50 Photochromic Compound Identification

[00208] The photochromic compound, according to the embodiment, is, for example, a viscous solid or liquid at room temperature and atmospheric pressure. From this solid or liquid, a photochromic compound can be isolated by a separation operation such as thin-layer chromatography, silica-gel column chromatography, high-performance liquid chromatography, and gas chromatography. Furthermore, it can be confirmed that the isolate does not include byproducts other than the photochromic compound, such as raw material compounds and dye components.

[00209] In a proton nuclear magnetic resonance (1H-NMR) spectroscopy, the obtained photochromic compound showed peaks attributed to aromatic protons and alkene protons around δ: 5.0 to 9.0 ppm, and peaks attributed to alkyl and alkylene protons around δ: 1.0 to 4.0 ppm. When the intensities of each spectrum are compared, the number of protons corresponding to each bonding group can be determined. This allows the identification of the skeleton, substituents, and similar components of the photochromic compound.

[00210] When the photochromic compound is contained in a cured product, such as a resin, this resin is dissolved and subjected to Petition 870250084631, dated 09 / 19 / 2025, page 60 / 223 56 / 180 separation methods described above to isolate the photochromic compound. Photochromic Composition

[00211] The photochromic compound, according to the embodiment, is soluble in general organic solvents such as toluene, chloroform, and tetrahydrofuran. The photochromic compound with the skeleton represented by formula (1) is dissolved in such a solvent to obtain a colorless and transparent solution. When this solution is exposed to sunlight or ultraviolet rays, it rapidly develops color and, when blocked from sunlight or similar light, reversibly and rapidly returns to its original colorless state and exhibits good photochromic function.

[00212] Furthermore, the photochromic compound, according to the embodiment, can be used in combination with other photochromic compounds with different structures, depending on the intended purpose. For example, the photochromic compound can be used in combination with other photochromic compounds to obtain the various color tones needed for photochromic lenses. The photochromic compounds to be used in combination can be any known compounds, without limitation. Examples of photochromic compounds to be used in combination include indenonaphthopyran, naphthopyran, spirooxazine, spiropyran, fulgide, fulgimide, diarylethane and the like. Above all, an indenonaphthopyran compound is particularly preferable because it can maintain uniform color tones during color development / fading, suppress the color change during color development that accompanies the degradation of photochromic properties, and further reduce initial tinting.It is preferable to adjust the color tone using various types of photochromic compounds in combination, because the combination can achieve both a high optical color density and a high color fading rate, especially at high temperatures, and also has excellent... Petition 870250084631, dated 09 / 19 / 2025, page 61 / 223 57 / 180 durability.

[00213] When the photochromic composition includes the photochromic compound according to the modality and other photochromic compounds, the composition proportions of each photochromic compound are determined as appropriate, depending on the desired color tone. Photochromic curable composition

[00214] The photochromic curable composition, like the curable composition according to the embodiment, contains the photochromic compound according to the embodiment and at least one selected from a group consisting of a radical polymerizable monomer, a cationic polymerizable monomer, a compound with a polymerizable group, and a (thio)urethane(urea) polymer. In this case, the (thio)urethane(urea) polymer includes at least one selected from a group consisting of a urethane polymer, a thiourethane polymer, a urethaneurea polymer, and a thiourethaneurea polymer.

[00215] Preferably, the photochromic compound and the photochromic composition according to the embodiment are used as a photochromic curable composition in combination with a polymerizable compound.

[00216] The curable photochromic composition depends on the intensity of color development of the photochromic compound, the materials selected for the lenses, and the lens thickness. Therefore, it is preferable, although not always the case, that the photochromic compound (or photochromic composition) be used in an amount of 0.001 to 10 parts by mass, based on 100 parts by mass of the polymerizable compound. The ideal composition ratio of this photochromic compound varies according to the intended purpose. For example, there is a difference, as described below, between the case where the curable photochromic composition is used as an optical article... Petition 870250084631, dated 09 / 19 / 2025, page 62 / 223 58 / 180 co thin film and the case where the photochromic curable composition is used as a thick film optical article. Use as thin film optical article

[00217] For example, when the photochromic curable composition is formed into a thin film with a thickness of 10 μm or more and less than 1000 μm, for example, about 100 μm (polymer film with the polymerized photochromic curable composition), it is preferable that the color tone be adjusted by mixing the photochromic compound (or photochromic composition) in an amount of 0.001 to 10 parts by mass based on 100 parts by mass of other polymerizable monomers. Use as a thick-film optical article

[00218] When the photochromic curable composition is formed into a thick cured product (product formed by polymer with the polymerized photochromic curable composition) having a thickness of, for example, 1 mm or more, it is preferable that the color tone be adjusted by mixing the photochromic compound (or photochromic composition) according to the present invention in an amount of 0.001 to 1 part by mass based on 100 parts by mass of the thick cured product or other polymerizable monomers capable of providing a thick cured product. Polymerizable Compound

[00219] As described above, the photochromic compound is preferably used in combination with a polymerizable compound, as a photochromic curable composition. Examples of the polymerizable compound include a urethane- or urea-based polymerizable compound capable of forming a urethane bond, a urea bond or similar, a compound with a polymerizable group, a free-radical polymerizable compound, an epoxy-based polymerizable compound, and the like. These polymerizable compounds are not Petition 870250084631, dated 09 / 19 / 2025, p. 63 / 223 59 / 180 particularly limited, but, for example, the polymerizable compound described in Patent Document 7 can be used appropriately.

[00220] Above all, the following polymerizable compounds are particularly suitable for use. Compound with a polymerizable group

[00221] The compound with a polymerizable group is exemplified by a compound with an iso(thio)cyanate group. The iso(thio)cyanate compound is a compound with either an isocyanate group or an isothiocyanate group, and may have either the isocyanate group or the isothiocyanate group. Appropriately, this compound is used in combination with a compound including active hydrogen, described later. Examples of such an iso(thio)cyanate compound include, among others, the following compounds. Polyiso(thio)cyanate

[00222] Polyiso(thio)cyanates are compounds that have at least two or more iso(thio)cyanate groups in a molecule. Examples of polyiso(thio)cyanates include an aromatic polyiso(thio)cyanate with an aromatic ring, such as m-xylene diisocyanate and 4,4'-diphenylmethane diisocyanate, and an aliphatic polyiso(thio)cyanate, such as norbornane diisocyanate and cyclohexylmethane-4,4'-diisocyanate diisocyanate. Compound with active hydrogen

[00223] The compound containing active hydrogen is preferably, but not limited to, a compound with a hydroxyl group and / or a thiol group, particularly preferably a polyfunctional compound with two or more active hydrogen atoms in a molecule. Specific examples of the compound with active hydrogen include: a polyfunctional thiol compound, such as pentaerythritol tetrakis(3-mercaptopropionate) and 4-mercaptomethyl-3,6-dithia-octanedithiol, and an alPetição 870250084631, dated 19 / 09 / 2025, page 64 / 223 60 / 180 polyfunctional alcohol, such as trimethylolpropane and pentaerythritol. Radical-Polymerizable Compound

[00224] Radical polymerizable compounds include polyfunctional radical polymerizable compounds and monofunctional radical polymerizable compounds. These compounds can be used alone or in combination with others. Examples of radical polymerizable substituents include a group with an unsaturated double bond, i.e., a vinyl group (including a styryl group, a (meth)acrylic group, an allyl group, and the like).

[00225] A radically polymerizable polyfunctional compound has two or more radically polymerizable substituents in one molecule. This radically polymerizable polyfunctional compound includes a first radically polymerizable polyfunctional compound with 2 to 10 radically polymerizable substituents and a second radically polymerizable polyfunctional compound with more than 10 radically polymerizable substituents.

[00226] The first radically polymerizable polyfunctional compound is not particularly limited, but more preferably has 2 to 6 radically polymerizable substituents. Specific examples are as follows. Polyfunctional (meth)acrylic acid ester compound

[00227] Ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, tetraethylene glycol di(meth)acrylate, ethylene glycol bisglycidyl (meth)acrylate, bisphenol A di(meth)acrylate, 2,2-bis(4-(meth)acryloyloxyethoxyphenyl)propane, 2,2-bis(3,5-dibromo-4(meth)acryloyloxyethoxyphenyl)propane. Polyfunctional Allyl Compound

[00228] Diallyl phthalate, diallyl terephthalate, diallyl isophthalate, diallyl tartrate, diallyl epoxy succinate, diallyl fumarate, diallyl chlorendate, diallyl hexaphthalate, diallyl carbonate, carbo Petition 870250084631, dated 09 / 19 / 2025, page 65 / 223 61 / 180 allyl diglycol nate, trimethylol propane triallyl carbonate. Polyfunctional thio(meth)acrylic acid ester compound

[00229] 1,2-bis(methacryloylthio)ethane, bis(2-acryloylthioethyl)ether, 1,4-bis(methacryloylthiomethyl)benzene. Vinyl compound Divinylbenzene.

[00230] Examples of the second radically polymerizable polyfunctional compound having more than 10 radically polymerizable substituents include relatively high molecular weight compounds, such as a silsesquioxane compound having one radically polymerizable substituent and a polyrhotaxane compound having one radically polymerizable substituent.

[00231] A monofunctional radical polymerizable compound has a radical polymerizable substituent in its molecule, and specific examples of it include, but are not limited to, the following compounds.

[00232] Unsaturated Carboxylic Acid

[00233] Acrylic acid, methacrylic acid, maleic anhydride.

[00234] (Meth)acrylic acid ester

[00235] Methyl methacrylate, benzyl methacrylate, phenyl methacrylate.

[00236] 2-hydroxyethyl methacrylate, glycidyl (meth) acrylate, β-methylglycidyl (meth) acrylate, bisphenol A-monoglycidyl ether methacrylate, 4-glycidyl oxymethacrylate, 3-(glycidyl-2-oxyethoxy)-2-hydroxy, propyl methacrylate, 3(glycidyloxy-1-isopropyloxy)-2-hydroxypropylacrylate, 3-(glycidyloxy-2hydroxypropyloxy)-2-hydroxypropylacrylate.

[00237] Fumaric acid ester

[00238] Diethyl fumarate, diphenyl fumarate.

[00239] Thio(meth)acrylic acid

[00240] Methyl thioacrylate, benzyl thioacrylate, thiomethacrylate Petition 870250084631, dated 09 / 19 / 2025, page 66 / 223 62 / 180 benzyl. Vinyl compound

[00241] Styrene, chlorostyrene, tylestyrene, vinyl naphthalene, α-methylstyrene dimer, bromostyrene.

[00242] The radical polymerizable compound may be used alone or in combination with two or more types. In this case, based on 100 parts by mass of the total quantity of radical polymerizable compounds, the quantities of the polyfunctional radical polymerizable compound and the monofunctional radical polymerizable compound are preferably 80 to 100 parts by mass and 0 to 20 parts by mass, respectively, more preferably 90 to 100 parts by mass and 0 to 10 parts by mass, respectively.Furthermore, based on 100 parts by mass of the total amount of the radical polymerizable compound, the amounts of the first polyfunctional radical polymerizable compound, the second polyfunctional radical polymerizable compound, and the monofunctional radical polymerizable compound are preferably 80 to 100 parts by mass, 0 to 20 parts by mass, and 0 to 20 parts by mass, respectively, or more preferably 85 to 100 parts by mass, 0 to 10 parts by mass, and 0 to 10 parts by mass, respectively. Several compound agents

[00243] The curable composition may contain various known compounding agents, unless the effects of the composition are impaired. Examples of compositional agents include various stabilizers such as release agents, ultraviolet absorbers, infrared absorbers, ultraviolet stabilizers, antioxidants, color inhibitors, antistatic agents, fluorescent dyes, colorants, pigments, and fragrances. In addition, solvents and leveling agents may be mixed in. Thiols, such as todecyl mercaptan, may be mixed in as powder modifiers. Petition 870250084631, dated 09 / 19 / 2025, page 67 / 223 63 / 180 limerization.

[00244] Among the above compositional agents, ultraviolet stabilizers are suitable as they can improve the durability of the photochromic site. Such are known ultraviolet stabilizers, hindered amine light stabilizers, hindered phenolic antioxidants, sulfur-based antioxidants and the like. Particularly suitable ultraviolet stabilizers are the following.

[00245] Bis(1,2,2,6,6-pentamethyl-4-piperidyl) sebacate; ADK STAB LA-52, LA-57, LA-62, LA-63, LA-67, LA-77, LA-82, LA-87 from ADEKA Corporation; 2,6-di-tert-butyl-4-methylphenol, ethylene bis(oxyethylene) bis[3(5-tert-butyl-4-hydroxy-m-tolyl) propionate]; IRGANOX1010, 1035, 1075, 1098, 1135, 1141, 1222, 1330, 1425, 1520, 259, 3114, 3790, 5057, 565 from BASF Japan. The amount of this ultraviolet stabilizer used is not particularly limited, unless the effects of the stabilizer are impaired, but is typically in the range of 0.001 to 10 parts by mass, particularly 0.01 to 1 part by mass based on 100 parts by mass of the photochromic curable composition.

[00246] In addition to the ultraviolet stabilizer, an ultraviolet absorber may also be used. As an ultraviolet absorber, a known ultraviolet absorber may be used, such as a benzophenone compound, a benzotriazole compound, a cyanoacrylate compound, a triazine compound, and a benzoate compound. Above all, a cyanoacrylate compound and a benzophenone compound are preferable. Preferably, the above ultraviolet stabilizer is used in a range of 0.001 to 5 parts by mass, based on 100 parts by mass of the photochromic curable composition containing a photochromic compound and a polymerizable compound. Method for use of curable photochromic composition; Optical article

[00247] A cured photochromic product is obtained by curing the com Petition 870250084631, dated 09 / 19 / 2025, page 68 / 223 64 / 180 curable photochromic position. Polymerization curing for the preparation of the cured photochromic product is carried out by irradiation with active energy rays, such as ultraviolet rays, α rays, β rays and γ rays, heating or a combination thereof, by means of radical polymerization, ring-opening polymerization, anionic polymerization or condensation polymerization. This means that an appropriate polymerization medium must be adopted depending on the types of polymerizable compound or polymerization cure promoter and the shape of the cured photochromic product to be formed.

[00248] When thermally polymerizing a curable composition containing a polymerizable compound, the temperature affects the properties of the resulting cured photochromic product.

[00249] This temperature condition is affected by the type and quantity of the thermal polymerization initiator and the type of polymerizable compound and, therefore, although it cannot be generally limited, it is generally preferable to initiate polymerization at a relatively low temperature and gradually increase it. As the polymerization time also varies depending on several factors, such as temperature, it is preferable to determine the ideal time beforehand according to these conditions. However, it is generally desirable to select a polymerization condition such that polymerization is completed within 2 to 48 hours. When obtaining a photochromic laminated sheet, it is preferable that polymerization be carried out at a temperature at which the reaction between the polymerizable functional groups proceeds and, at that point, the ideal temperature and time are determined so that the molecular weight is as desired.

[00250] Furthermore, when photopolymerizing the curable composition, the UV intensity between polymerization conditions particularly affects the properties of the resulting photochromic cured product. This illuminance condition is affected by the type and quantity of the photoinitiator. Petition 870250084631, dated 09 / 19 / 2025, page 69 / 223 65 / 180 pain and by the type of polymerizable monomer and, therefore, although it cannot be limited in general, it is generally preferable to select a condition such that UV light at a wavelength of 365 nm, with an intensity of 50 to 500 mW / cm2, is emitted for 0.5 to 5 minutes. Optical Article

[00251] The photochromic compound, according to the embodiment, can be widely used as a photochromic material, for example, as various memory materials that are alternatives to silver halide photosensitive materials, copy materials, printing photoreceptors, cathode ray tube memory materials, laser photosensitive materials, and various memory materials such as photosensitive materials for holography. Photochromic materials can also be used as photochromic lens materials, optical filter materials, display materials, as well as materials for actinometers, decoration, fabrics, ropes, and the like.

[00252] The photochromic compound, according to the embodiment, is particularly suitable for applications in photochromic lenses. Photochromic lenses are suitable for spectacle lenses, such as sunglasses lenses. Any known method can be adopted as a method of producing the photochromic lens, provided that it is possible to obtain uniform darkening performance.

[00253] When photochromic properties are exhibited by a kneading method, the curable composition described above is injected between glass molds held together by an elastomer gasket or spacer and then polymerized by melting by heating in an air furnace or irradiation with an active energy beam, such as ultraviolet radiation, depending on the types of polymerizable compound and polymerization cure promoter, resulting in a photochromic cured product formed in an optical material, such as a lens. Petition 870250084631, dated 09 / 19 / 2025, page 70 / 223 66 / 180

[00254] When exhibiting photochromic properties by a lamination method, the curable composition is dissolved in an appropriate organic solvent to prepare a coating liquid, which is then applied to the surface of an optical substrate, such as a lens substrate, by centrifugation, immersion or similar. The coating liquid is dried to remove the organic solvent and then cured by polymerization with UV irradiation, heating or similar in an inert gas, such as nitrogen, to form a photochromic layer composed of the cured photochromic product on the surface of the optical substrate (coating method).

[00255] Alternatively, an optical substrate, such as a lens substrate, is arranged so as to face a glass mold, so that predetermined voids are formed, and a curable composition is injected into these voids. In this state, a photochromic layer, consisting of a cured photochromic product, can be formed on the surface of the optical substrate also by fusion polymerization using an internal mold in which the polymerization curing is carried out by UV irradiation, heating or similar (fusion polymerization method).

[00256] When forming a photochromic layer on the surface of an optical substrate using the lamination method described above (coating method and casting polymerization method), the adhesion between the photochromic layer and the optical substrate can be improved by first subjecting the surface of the optical substrate to a chemical treatment using an alkaline solution, an acidic solution or similar, or to a physical treatment using corona discharge, plasma discharge, polishing or similar. Obviously, it is also possible to provide a layer of transparent adhesive resin on the surface of the optical substrate.

[00257] In addition, by acquiring photochromic properties Petition 870250084631, dated 09 / 19 / 2025, page 71 / 223 67 / 180 a binder method, a photochromic sheet is prepared by sheet forming using a curable composition, this sheet is inserted between two transparent sheets (optical sheets) and then cured by polymerization as described above, to obtain a photochromic binder sheet having a photochromic layer as an adhesive layer.

[00258] In this case, for the preparation of the photochromic sheet, it is also possible to adopt a method in which a curable composition is dissolved in an organic solvent to prepare a coating liquid, and this coating liquid is used for coating. An adhesive layer can be provided between the photochromic sheet and the optical sheet.

[00259] For example, the binder sheet prepared in this way is placed in a mold, in which a thermoplastic resin (e.g., polycarbonate) for an optical substrate, such as a lens, is formed by injection, to obtain an optical substrate, such as a lens, in a predetermined shape with photochromic properties.

[00260] In addition, this binder sheet can be bonded to the surface of the optical substrate using an adhesive or similar to obtain a photochromic lens.

[00261] In addition, the photochromic layer or the cured photochromic product prepared from the curable composition can be subjected to post-processing, for example, dyeing using dyes as dispersing dyes, forming a rigid coating film using a silane coupling agent or a rigid coating agent containing predominantly a silicon, zirconium, antimony, aluminum, tin, tungsten, etc. sol, forming a thin film by vapor deposition of metal oxides such as SiO2, TiO2 and ZrO2, anti-reflective treatment using a thin film formed by the application of organic polymers, antistatic treatment Petition 870250084631, dated 09 / 19 / 2025, page 72 / 223 68 / 180 co and protective coating treatment with a urethane resin or similar. EXAMPLES

[00262] The present invention will be explained in more detail with reference to the Examples below. These Examples are intended only to explain the present invention, and the spirit and scope of the present invention are not limited to these Examples. Example 1 First stage

[00263] 95.4 g (500 mmol) of p-toluenesulfonic acid monohydrate and 1000 mL of toluene were mixed, the mixture was subjected to azeotropic dehydration and it was confirmed that the water content was 202 ppm.

[00264] Using the method described in Patent Document 8, 37.3 g (100.0 mmol) of a carboxylic acid compound represented by formula (30) below, synthesized from 3-bromo-4-methoxybenzophenone, were added to the mixture, which reacted during azeotropic dehydration. After confirmation of the consumption of the raw materials, the mixture was cooled to room temperature and then the resulting solid was filtered to obtain a carbonyl compound represented by formula (31) below, with a yield of 90%. Chemical Formula 51 Petition 870250084631, dated 09 / 19 / 2025, page 73 / 223 69 / 180 Chemical Formula 52 Second Stage

[00265] Referring to the method described in Patent Document 9, a reaction was carried out using the carbonyl compound represented by formula (31) above to obtain a naphthol derivative represented by formula (32) below with a yield of 83%. Chemical Formula 53 Third Stage

[00266] 17.1 g (49.9 mmol) of the naphthol derivative represented by formula (32) above, 11.2 g (54.3 mmol) of 4-morpholinophenylboronic acid, 11.5 g (108.7 mmol) of sodium carbonate, 103.5 mL of water, 121.5 mL of 1,2-dimethoxyethane and 12.2 mL of ethanol were added and stirred while nitrogen bubbling was carried out. Nitrogen bubbling continued for about 20 minutes and then 142.7 mg (0.1 mmol) of Pd(PPh3)4 were added to the mixture, which reacted at 75°C for 2 hours. After the reaction, the mixture was cooled to room temperature, to which 650 mL of THF were added. The mixture was cooled to 0–5°C, then adjusted to pH 1 by adding concentrated hydrochloric acid and submerging it. Petition 870250084631, dated 09 / 19 / 2025, page 74 / 223 70 / 180 subjected to liquid separation. The mixture was washed twice with 500 mL of water to remove the solvent. The mixture was purified by resuspension with 300 mL of methanol to obtain a naphthol derivative represented by formula (33) below, with a yield of 96%. Chemical Formula 54 Fourth Stage (33)

[00267] To 50 mL of toluene, 2.91 g (10.0 mmol) of 4-bromo-4'-methoxybenzophenone, 1.50 g (14.0 mmol) of N-methylaniline and 0.29 g (30.0 mmol) of sodium t-butoxide were added, and the mixture was bubbled with nitrogen for 20 minutes. To this mixture, 46 mg (0.05 mmol) of tris(dibenzylideneacetone)dipalladium(0) and 95 mg (0.20 mmol) of 2-cyclohexylphosphinotriisopropylbiphenyl were added, and the mixture was reacted at 80°C for 3 hours. After the reaction was complete, the mixture was cooled to room temperature and then 30 mL of THF were added to the mixture, which was filtered. The mixture was cooled to 0-5°C and 10% hydrochloric acid was added until the pH reached 6-7. The mixture was then subjected to liquid separation and washed three times with 100 mL of water.The solvent was removed from the organic layer obtained and the organic layer was purified by silica gel chromatography to obtain a benzophenone represented by formula (34) below, with a yield of 92%. Petition 870250084631, dated 09 / 19 / 2025, page 75 / 223 71 / 180 Chemical Formula 55 (34)

[00268] Referring to the method described in the Patent Document 6, the benzophenone obtained was used to obtain a propargyl alcohol represented by formula (35) below with a yield of 86%. Fifth Stage

[00269] First, 2.80 g (6.6 mol) of the naphthol derivative represented by formula (33) above, 5.60 g of WAKOGEL C300 and 80 mL of toluene were mixed and heated to 100°C. To this mixture, 2.71 g (7.9 mmol) of propargyl alcohol represented by formula (35) above, dissolved in 20 mL of toluene, were added and heated to 100°C. After consumption of the naphthol derivative as raw material, the mixture was cooled to room temperature and 40 mL of water were added to the mixture, which was subjected to liquid separation. The solvent was removed from the obtained organic layer and the organic layer was purified by silica gel chromatography to obtain a photochromic compound represented by formula (36) below, with a yield of 87%. Petition 870250084631, dated 09 / 19 / 2025, page 76 / 223 72 / 180 Chemical Formula 57 Sixth Stage

[00270] 4.1 g (5.5 mmol) of the photochromic compound represented by formula (36) above, 3.9 g (27.5 mmol) of iodomethane and 60 mL of THF were mixed and cooled with ice. To the mixture, 1.8 g (16.5 mmol) of tBuOK was added in four batches, maintaining the temperature between 0 and 5°C. After confirmation of the consumption of the raw materials, the mixture was neutralized with 10% hydrochloric acid, to which 30 mL of toluene were added, and the mixture was subjected to liquid separation. The solvent was removed from the obtained organic layer and then the organic layer was purified by silica gel chromatography to obtain a photochromic compound represented by formula (37) below, with a yield of 89%. Chemical Formula 58

[00271] The photochromic compound represented by formula (37) above had elemental analysis values ​​of C: 81.93%, H: 6.21% and N: Petition 870250084631, dated 09 / 19 / 2025, page 77 / 223 73 / 180 3.62%, which were considerably consistent with the calculated values ​​of C53H48N2O4 of C: 81.93%, H: 6.23% and N: 3.61%.

[00272] In a proton nuclear magnetic resonance spectroscopy, the photochromic compound represented by formula (37) showed 13H peaks attributed to a methyl group and a morpholino group around δ0.5 to 3.0 ppm, 10H peaks attributed to a methoxy group and a morpholino group around δ3.0 to 5.0 ppm and 25H peaks attributed to aromatic protons and alkene protons around δ5.0 to 9.0 ppm.

[00273] Furthermore, in a 13C nuclear magnetic resonance spectroscopy, the photochromic compound represented by formula (37) showed a peak attributed to the carbon of an aromatic ring around δ110 at 160 ppm, a peak attributed to the carbon of an alkene around δ80 at 140 ppm and a peak attributed to the carbon of an alkyl at δ20 at 60 ppm. Example 2 First Stage

[00274] With reference to the method described in Patent Document 8, 31.8 g (68.6 mmol) of the compound represented by formula (38) below synthesized from the carboxylic acid compound represented by formula (30) above, 550 mL of toluene, 14.79 g (87.4 mmol) of diphenylamine and 30.8 g (274.6 mmol) of sodium t-butoxy were mixed and stirred under reduced pressure, from which dissolved oxygen was removed. Subsequently, 0.57 g (0.6 mmol) of Pd2(dba)3 and 1.19 g (2.5 mmol) of X-fos were added to the reaction liquid, which was heated to 80°C. Heating was continued until the raw materials became invisible and, after completion of the reaction, the reaction liquid was cooled to room temperature and then filtered. To the resulting filtrate, 500 mL of tetrahydrofuran and 10% hydrochloric acid were added, which was neutralized and, in Petition 870250084631, dated 09 / 19 / 2025, page 78 / 223 74 / 180 then subjected to liquid separation. The resulting organic layer was concentrated and then purified by resuspending with 200 mL of methanol to obtain a carboxylic acid compound represented by formula (39) below, with a yield of 87%. Chemical Formula 59 Second Stage

[00275] Referring to the method described in Patent Document 8, except that the carboxylic acid compound obtained in the first step was used, an iodine compound represented by formula (40) below was obtained with a yield of 75%. Chemical Formula 61 (40) Third Stage

[00276] 28.4 g (44.8 mmol) of the compound represented by the formula Petition 870250084631, dated 09 / 19 / 2025, page 79 / 223 75 / 180 mule (40) above, obtained in the second stage, 400 mL of toluene were added, which was subjected to azeotropic dehydration until the water content in the toluene decreased to a maximum of 100 ppm. After azeotropic dehydration, the mixture was slowly cooled to -20°C, at which point 33.6 mL of n-BuLi (1.6 mol / L hexane solution) were slowly added dropwise, maintaining the temperature between -15 and -20°C. After confirming the consumption of the raw materials, 8.64 g (56.0 mmol) of 4,4-diethylcyclohexanone were slowly added dropwise to the mixture, maintaining the temperature between -5 and -20°C. After the dropwise addition, the temperature was slowly raised to room temperature. After increasing the temperature, 200 mL of water were added to the mixture, which was then subjected to liquid separation. The mixture was repeatedly washed with water until the pH of the aqueous layer reached 7 to 8.From the organic layer obtained, the solvent was removed and the organic layer was purified by silica gel chromatography to obtain a compound represented by formula (41) below with a yield of 86%. Chemical Formula 62 Fourth Stage

[00277] To 25.5 g (38.5 mmol) of the compound represented by formula (41) above, 500 mL of THF were added and dissolved, followed by 7.6 g of 5% Pd / C (water content: 50%), which was reacted Petition 870250084631, dated 09 / 19 / 2025, page 80 / 223 76 / 180 in hydrogen gas under a pressure of 0.05 to 0.1 MPa. After confirmation of the consumption of the raw materials, the Pd / C was filtered and, from the organic layer obtained, the solvent was removed to obtain a compound represented by formula (42) below, with a yield of 100%. Chemical Formula 63 (42) Fifth Stage

[00278] To 14.7 g (77.0 mmol) of hydrate, 750 mL of p-toluenesulfonic acid monoid toluene was added, which was subjected to azeotropic dehydration until the water content in the toluene decreased to a maximum of 150 ppm. Then, 100 mL of a toluene solution containing 22.0 g (38.5 mmol) of the compound represented by formula (42) above was slowly added to this mixture, maintaining the temperature between 85 and 100°C. After dropwise addition, the mixture was refluxed. After confirming the consumption of the raw materials, the mixture was cooled to room temperature, to which 500 mL of water was added, which was subjected to liquid separation. This operation was repeated three times, the solvent was removed from the organic layer obtained and the organic layer was purified by silica gel chromatography to obtain a naphthol derivative represented by formula (43) below, with a yield of 83%. Petition 870250084631, dated 09 / 19 / 2025, page 81 / 223 77 / 180 Chemical Formula 64 (43) Fifth Stage

[00279] The same reaction as in the fourth step of Example 1 was carried out, except that 4-bromo-4'-methylbenzophenone was used instead of 4-bromo-4'-methoxybenzophenone and 4-(methylamino)toluene was used instead of N-methylaniline, to obtain a propargyl alcohol represented by formula (44) below with a yield of 89%. Chemical Formula 65 (44) Sixth Stage

[00280] 3.05 g (5.5 mmol) of the naphthol derivative represented by formula (43) above, 6.00 g of WAKOGEL C300 and 60 mL of toluene were mixed and heated to 100°C. To this mixture, 10 mL of toluene solution containing 2.26 g (6.6 mmol) of the propargyl alcohol represented by formula (44) above were added dropwise, so that the internal temperature was maintained between 95 and 100°C. After confirming the consumption of the raw materials, the mixture was filtered and, from the organic layer obtained, the solvent was removed, and the organic layer was purified by silica gel chromatography to obtain a photochromic compound represented by formula (45) below. Petition 870250084631, dated 09 / 19 / 2025, page 82 / 223 78 / 180 with a yield of 77%. Chemical Formula 66 (45)

[00281] The photochromic compound represented by formula (45) above had elemental analysis values ​​of C: 86.29%, H: 6.87% and N: 3.21%, which were considerably consistent with the calculated values ​​of C63H60N2O2 of C: 86.26%, H: 6.89% and N: 3.19%.

[00282] In a proton nuclear magnetic resonance spectroscopy, the photochromic compound represented by formula (45) showed 27H peaks attributed to a methyl group and a 4,4-diethylcyclohexyl ring group around δ0.5 to 3.0 ppm, a 3H peak attributed to a methoxy group around δ3.0 to 5.0 ppm and 30H peaks attributed to aromatic protons and alkene protons around δ5.0 to 9.0 ppm.

[00283] Furthermore, in a 13C nuclear magnetic resonance spectroscopy, the photochromic compound represented by formula (45) showed a peak attributed to the carbon of an aromatic ring around δ110 at 160 ppm, a peak attributed to the carbon of an alkene around δ80 at 140 ppm and a peak attributed to the carbon of an alkyl at δ20 at 60 ppm. Example 3

[00284] The same reaction from the first step of Example 1 was carried out, except that 4,4'-dimethoxybenzophenone was used instead of 3 Petition 870250084631, dated 09 / 19 / 2025, page 83 / 223 79 / 180 bromo-4-methoxybenzophenone, and the same reaction as in the sixth step of Example 1 was carried out, except that iodopropane was used instead of iodomethane, to obtain a photochromic compound represented by formula (46) below with a yield of 82%. Chemical Formula 67 MeO 7

[00285] The photochromic compound represented by formula (46) above had elemental analysis values ​​of C: 82.11%, H: 6.76% and N: 2.01%, which were considerably consistent with the calculated values ​​of C48H47NO4 of C: 82.14%, H: 6.75% and N: 2.00%.

[00286] In a proton nuclear magnetic resonance spectroscopy, the photochromic compound represented by formula (46) showed 17H peaks assigned to a methyl group and a propyl group around δ0.5 to 3.0 ppm, a 9H peak assigned to a methoxy group around δ3.0 to 5.0 ppm and 21H peaks assigned to aromatic protons and alkene protons around δ5.0 to 9.0 ppm.

[00287] Furthermore, in a 13C nuclear magnetic resonance spectroscopy, the photochromic compound represented by formula (46) showed a peak attributed to the carbon of an aromatic ring around δ110 at 160 ppm, a peak attributed to the carbon of an alkene around δ80 at 140 ppm and a peak attributed to the carbon of an alkyl at δ20 at 60 ppm. Example 4 Petition 870250084631, dated 09 / 19 / 2025, page 84 / 223 80 / 180 First Stage

[00288] The same reaction as in the fourth step of Example 1 was carried out, except that 4-bromo-4'-fluorobenzophenone was used instead of 4-bromo-4'-methoxybenzophenone and N-ethylaniline was used instead of N-methylaniline, to obtain a propargyl alcohol represented by formula (47) below with a yield of 91%. (47) Second Stage

[00289] The same reaction as in the first step of Example 1 was carried out, except that 4-methoxybenzophenone was used instead of 3-bromo4-methoxybenzophenone, and the same reaction as in the sixth step of Example 1 was carried out, except that iodohexane was used instead of iodomethane, to obtain a photochromic compound represented by formula (48) below with a yield of 79%. Chemical Formula 69 (48)

[00290] The photochromic compound represented by formula (48) above had elemental analysis values ​​of C: 83.96%, H: 7.43% and N: Petition 870250084631, dated 09 / 19 / 2025, page 85 / 223 81 / 180 1.84%, which were considerably consistent with the calculated values ​​of C53H56FNO4 of C: 83.98%, H: 7.45% and N: 1.85%.

[00291] In a proton nuclear magnetic resonance spectroscopy, the photochromic compound represented by formula (48) showed 31H peaks attributed to an ethyl group and a hexyl group around δ0.5 to 3.0 ppm, a 3H peak attributed to a methoxy group around δ3.0 to 5.0 ppm and 22H peaks attributed to aromatic protons and alkene protons around δ5.0 to 9.0 ppm.

[00292] Furthermore, in a 13C nuclear magnetic resonance spectroscopy, the photochromic compound represented by formula (48) showed a peak attributed to the carbon of an aromatic ring around δ110 at 160 ppm, a peak attributed to the carbon of an alkene around δ80 at 140 ppm and a peak attributed to the carbon of an alkyl at δ20 at 60 ppm. Example 5 First Stage

[00293] The same reaction as in the fourth step of Example 1 was carried out, except that 4-bromo-4'-propylbenzophenone was used instead of 4-bromo-4'-methoxylbenzophenone, to obtain a propargyl alcohol represented by formula (49) below with a yield of 92%. Chemical Formula 70 Second Stage

[00294] The same reaction as in the fifth step of Example 2 was carried out, except that a naphthol derivative represented by formula (50) below synthesized by reference to the method described in Patent Document 10 was used instead of the naphthol derivative represented by Petition 870250084631, dated 09 / 19 / 2025, page 86 / 223 82 / 180 formula (43) above and propargyl alcohol represented by formula (49) above was used instead of propargyl alcohol represented by formula (44) above, to obtain a photochromic compound represented by formula (51) below with a yield of 82%. Chemical Formula 71

[00295] The photochromic compound represented by formula (51) above had elemental analysis values ​​of C: 83.77%, H: 7.15%, N: 1.64% and S: 3.75%, which were considerably consistent with the calculated values ​​of C60H61NO2S of C: 83.78%, H: 7.15%, N: 1.63% and S: 3.73%.

[00296] In a proton nuclear magnetic resonance spectroscopy, the photochromic compound represented by formula (51) showed 34H peaks attributed to a methyl group, a propyl group and a 3,3,5,5-tetramethylcyclohexyl ring group around δ0.5 to 3.0 ppm, a 3H peak attributed to a methoxy group around δ3.0 Petition 870250084631, dated 09 / 19 / 2025, p. 87 / 223 83 / 180 at 5.0 ppm and 24H peaks attributed to aromatic protons and alkene protons around δ5.0 to 9.0 ppm.

[00297] Furthermore, in a 13C nuclear magnetic resonance spectroscopy, the photochromic compound represented by formula (51) showed a peak attributed to the carbon of an aromatic ring around δ110 at 160 ppm, a peak attributed to the carbon of an alkene around δ80 at 140 ppm and a peak attributed to the carbon of an alkyl at δ20 at 60 ppm. Example 6 First Stage

[00298] The same reaction as in the fourth step of Example 1 was carried out, except that N-cyclohexylaniline was used instead of N-methylaniline, to obtain a propargyl alcohol represented by formula (52) below with a yield of 89%. Chemical Formula 73 (52) Second Stage

[00299] The same reaction as the first step of Example 2, except that 3,4-dimethoxybenzophenone was used in bromo-4-methoxybenzophenone, the same reaction as the fifth step was performed instead of the 3rd step of Example 1 was carried out, except that propargyl alcohol represented by formula (52) above was used instead of propargyl alcohol represented by formula (35) above, and the same reaction of the sixth step of Example 1 was carried out, except that 1-bromo-4-fluorobutane was used instead of iodomethane, to obtain a photochromic compound represented by formula (53) below with a yield of 69%. Petition 870250084631, dated 09 / 19 / 2025, page 88 / 223 84 / 180 [Chemical Formula 74]

[00300] The photochromic compound represented by formula (53) above had elemental analysis values ​​of C: 79.18%, H: 6.88% and N: 1.66%, which were considerably consistent with the calculated values ​​of C55 H57F2NO4 of C: 79.20%, H: 6.89% and N: 1.68%.

[00301] In a proton nuclear magnetic resonance spectroscopy, the photochromic compound represented by formula (53) showed 27H peaks attributed to a cyclohexyl group and a 4-fluorobutyl group around δ0.5 to 3.0 ppm, a 9H peak attributed to a methoxy group around δ3.0 to 5.0 ppm and 21H peaks attributed to aromatic protons and alkene protons around δ5.0 to 9.0 ppm.

[00302] Furthermore, in a 13C nuclear magnetic resonance spectroscopy, the photochromic compound represented by formula (53) showed a peak attributed to the carbon of an aromatic ring around δ110 at 160 ppm, a peak attributed to the carbon of an alkene around δ80 at 140 ppm and a peak attributed to the carbon of an alkyl at δ20 at 60 ppm. Example 7 First Stage

[00303] The same reaction from the fourth step of Example 1 was carried out, except that 4-bromo-3'-fluoro-4'-methoxybenzophenone was used in Petition 870250084631, dated 09 / 19 / 2025, page 89 / 223 85 / 180 times 4-bromo-4'-methoxybenzophenone, to obtain a propargyl alcohol represented by formula (54) below with a yield of 91%. (54) Second Stage

[00304] The same reaction as in the third step of Example 1 was carried out, except that 2,4-dimethoxyphenylboronic acid was used instead of 4-morpholinophenylboronic acid, the same reaction as in the fifth step of Example 1 was carried out, except that propargyl alcohol represented by formula (54) above was used instead of propargyl alcohol represented by formula (35) above, and the same reaction as in the sixth step of Example 1 was carried out, except that iodopropane was used instead of iodomethane, to obtain a photochromic compound represented by formula (55) below with a yield of 73%. Chemical Formula 76 (55)

[00305] The photochromic compound represented by formula (55) above had elemental analysis values ​​of C: 79.95%, H: 6.34% and N: 1.69%, which were considerably consistent with the values ​​of Petition 870250084631, dated 09 / 19 / 2025, pp. 90-223 86 / 180 cells of C 55 H 52 FNO 5 of C: 79.97%, H: 6.35% and N: 1.70%.

[00306] In a proton nuclear magnetic resonance spectroscopy, the photochromic compound represented by formula (55) showed 17H peaks assigned to a methyl group and a propyl group around δ0.5 to 3.0 ppm, a 12H peak assigned to a methoxy group around δ3.0 to 5.0 ppm and 23H peaks assigned to aromatic protons and alkene protons around δ5.0 to 9.0 ppm.

[00307] Furthermore, in a 13C nuclear magnetic resonance spectroscopy, the photochromic compound represented by formula (55) showed a peak attributed to the carbon of an aromatic ring around δ110 at 160 ppm, a peak attributed to the carbon of an alkene around δ80 at 140 ppm and a peak attributed to the carbon of an alkyl at δ20 at 60 ppm. Example 8 First Stage

[00308] The same reaction from the fourth step of Example 1 was carried out, except that 4-bromo-3',4'-dimethoxybenzophenone was used instead. 4-bromo-4'-methoxybenzophenone and 4-fluoro-N-methylaniline were used instead of N-methylaniline, to obtain a propargyl alcohol represented by formula (56) below with a yield of 91%. Chemical Formula 77 (56) Second Stage

[00309] The same reaction from the first step of Example 1 was carried out, except that 4,4'-dimethylbenzophenone was used instead of 3-bromo-4-methoxybenzophenone, the same reaction as in the fifth step of Petition 870250084631, dated 09 / 19 / 2025, pp. 91 / 223 87 / 180 Example 1 was carried out, except that propargyl alcohol represented by formula (56) above was used instead of propargyl alcohol represented by formula (35) above, and the same reaction of the sixth step of Example 1 was carried out, except that 1-bromo-2-(2-methoxyethoxy)ethane was used instead of iodomethane, to obtain a photochromic compound represented by formula (57) below with a yield of 68%. Chemical Formula 78

[00310] The photochromic compound represented by formula (57) above had elemental analysis values ​​of C: 75.95%, H: 6.74% and N: 1.69%, which were considerably consistent with the calculated values ​​of C53H56FNO7 of C: 75.96%, H: 6.74% and N: 1.67%.

[00311] In a proton nuclear magnetic resonance spectroscopy, the photochromic compound represented by formula (57) showed 13H peaks attributed to a methyl group and a 2(2-methoxyethoxy)ethyl group around δ0.5 to 3.0 ppm, a 24H peak attributed to a methoxy group around δ3.0 to 5.0 ppm and 19H peaks attributed to aromatic protons and alkene protons around δ5.0 to 9.0 ppm.

[00312] Furthermore, in a 13C nuclear magnetic resonance spectroscopy, the photochromic compound represented by formula (57) showed a peak attributed to the carbon of an aromatic ring Petition 870250084631, dated 09 / 19 / 2025, pp. 92-223 88 / 180 around δ110 to 160 ppm, a peak attributed to the carbon of an alkene around δ80 to 140 ppm, and a peak attributed to the carbon of an alkyl at δ20 to 60 ppm. Example 9 First Stage

[00313] The same reaction as in the fourth step of Example 1 was carried out, except that 4-bromo-4'-propoxybenzophenone was used instead of 4-bromo-4'-methoxybenzophenone and N-(2,2,2-trifluoroethyl)aniline was used instead of N-methylaniline, to obtain a propargyl alcohol represented by formula (58) below with a yield of 87%. Chemical Formula 79 (58)

[00314] The same reaction as in the fifth step of Example 2 was carried out, except that a naphthol derivative represented by formula (59) below was used instead of the naphthol derivative represented by formula (43) above and propargyl alcohol represented by formula (58) above was used instead of propargyl alcohol represented by formula (44) above, to obtain a photochromic compound represented by formula (60) below with a yield of 74%. (59) Petition 870250084631, dated 09 / 19 / 2025, pp. 93 / 223 89 / 180 Chemical Formula 81

[00315] The photochromic compound represented by formula (60) above had elemental analysis values ​​of C: 80.09%, H: 6.16% and N: 1.85%, which were considerably consistent with the calculated values ​​of C50H46F3NO2 of C: 80.08%, H: 6.18% and N: 1.87%.

[00316] In a proton nuclear magnetic resonance spectroscopy, the photochromic compound represented by formula (60) showed 21H peaks attributed to a cyclooctane ring group, a (2,2,2-trifluoroethyl) group and a propyloxy group around δ0.5 to 3.0 ppm, a 2H peak attributed to a propyloxy group around δ3.0 to 5.0 ppm and 23H peaks attributed to aromatic protons and alkene protons around δ5.0 to 9.0 ppm.

[00317] Furthermore, in a 13C nuclear magnetic resonance spectroscopy, the photochromic compound represented by formula (60) showed a peak attributed to the carbon of an aromatic ring around δ110 at 160 ppm, a peak attributed to the carbon of an alkene around δ80 at 140 ppm and a peak attributed to the carbon of an alkyl at δ20 at 60 ppm. Example 10 First Stage

[00318] The same reaction from the fifth step of Example 2 was carried out, except that N-butylaniline was used instead of 4-(methylamino)toluene, to obtain a propargyl alcohol represented Petition 870250084631, dated 09 / 19 / 2025, pp. 94 / 223 90 / 180 by formula (61) below with a yield of 91%. Chemical Formula 82 (61) Second Stage

[00319] The same reaction as in the first step of Example 2 was carried out, except that morpholine was used instead of diphenylamine, the same reaction as in the third step of Example 2 was carried out, except that diethyl ketone was used instead of 4,4-diethylcyclohexanone, and the same reaction as in the fifth step of Example 2 was carried out, except that propargyl alcohol represented by formula (61) above was used instead of propargyl alcohol represented by formula (44) above, to obtain a photochromic compound represented by formula (62) below with a yield of 77%. Chemical Formula 83 (62)

[00320] The photochromic compound represented by formula (62) above had elemental analysis values ​​of C: 82.74%, H: 7.19% and N: 3.72%, which were considerably consistent with the calculated values ​​of C52H54N2O3 of C: 82.72%, H: 7.21% and N: 3.71%. Petition 870250084631, dated 09 / 19 / 2025, pp. 95 / 223 91 / 180

[00321] In a proton nuclear magnetic resonance spectroscopy, the photochromic compound represented by formula (62) showed 26H peaks attributed to a methyl group, an ethyl group, a butyl group and a morpholino group around δ0.5 to 3.0 ppm, 7H peaks attributed to a methoxy group and a morpholino group around δ3.0 to 5.0 ppm and 21H peaks attributed to aromatic protons and alkene protons around δ5.0 to 9.0 ppm.

[00322] Furthermore, in a 13C nuclear magnetic resonance spectroscopy, the photochromic compound represented by formula (62) showed a peak attributed to the carbon of an aromatic ring around δ110 at 160 ppm, a peak attributed to the carbon of an alkene around δ80 at 140 ppm and a peak attributed to the carbon of an alkyl at δ20 at 60 ppm. Example 11 First Stage

[00323] The same reaction as in the fourth step of Example 1 was carried out, except that 4-methoxy-N-methylaniline was used instead of N-methylaniline, to obtain a propargyl alcohol represented by formula (63) below with a yield of 93%. Chemical Formula 84 Second Stage

[00324] The same reaction as in the first step of Example 1 was carried out, except that 4-bromo-4'-methoxybenzophenone was used instead of 3-bromo-4-methoxybenzophenone, the same reaction as in the fifth step of Example 1 was carried out, except that the propargyl alcohol represented by formula (63) above was used instead of the propargyl alcohol represented by Petition 870250084631, dated 19 / 09 / 2025, page 96 / 223 92 / 180 represented by formula (35) above, and the same reaction as the sixth step of Example 1 was carried out, except that 1-bromo-4-methoxybutane was used instead of iodomethane, to synthesize a photochromic compound represented by formula (64) below. Chemical Formula 85 Third Stage

[00325] Referring to the method described in Patent Document 10, the photochromic compound represented by formula (64) above was reacted with 2,6-dimethylbenzenethiol to obtain a photochromic compound represented by formula (65) below with a yield of 86%. Chemical Formula 86 OMe

[00326] The photochromic compound represented by formula (65) Petition 870250084631, dated 09 / 19 / 2025, page 97 / 223 93 / 180 above had elemental analysis values ​​of C: 77.83%, H: 6.86%, N: 1.50%, and S: 3.44%, which were considerably consistent with the calculated values ​​of C 60 H 63 NO 6 S of C: 77.81%, H: 6.86%, N: 1.51%, and S: 3.46%.

[00327] In a proton nuclear magnetic resonance spectroscopy, the photochromic compound represented by formula (65) showed 21H peaks attributed to a methyl group and a 4-methoxybutyl group around δ0.5 to 3.0 ppm, 19H peaks attributed to a methoxy group and a 4-methoxybutyl group around δ3.0 to 5.0 ppm and 23H peaks attributed to aromatic protons and alkene protons around δ5.0 to 9.0 ppm.

[00328] Furthermore, in a 13C nuclear magnetic resonance spectroscopy, the photochromic compound represented by formula (65) showed a peak attributed to the carbon of an aromatic ring around δ110 at 160 ppm, a peak attributed to the carbon of an alkene around δ80 at 140 ppm and a peak attributed to the carbon of an alkyl at δ20 at 60 ppm. Example 12 First Stage

[00329] The same reaction as in the first step of Example 1 was carried out, except that 3-bromo-4-methoxy-4'-methylbenzophenone was used instead of 3-bromo-4-methoxybenzophenone, the same reaction as in the third step of Example 1 was carried out, except that 2,4,6-trimethoxyphenylboronic acid was used instead of 4-morpholinophenylboronic acid, and the same reaction as in the sixth step of Example 1 was carried out, except that 1-bromo-3-methylthiopropane was used instead of iodomethane, to obtain a photochromic compound represented by formula (66) below with a yield of 74%. Petition 870250084631, dated 09 / 19 / 2025, pp. 98 / 223 94 / 180 Chemical Formula 87 (66)

[00330] The photochromic compound represented by formula (66) above had elemental analysis values ​​of C: 75.07%, H: 6.50%, N: 1.48% and S: 6.80%, which were considerably consistent with the calculated values ​​of C59H61NO6S2 of C: 75.05%, H: 6.51%, N: 1.48% and S: 6.79%.

[00331] In a proton nuclear magnetic resonance spectroscopy, the photochromic compound represented by formula (66) showed 24H peaks attributed to a methyl group and a 3-methylthiopropyl group around δ0.5 to 3.0 ppm, a 15H peak attributed to a methoxy group around δ3.0 to 5.0 ppm and 22H peaks attributed to aromatic protons and alkene protons around δ5.0 to 9.0 ppm.

[00332] Furthermore, in a 13C nuclear magnetic resonance spectroscopy, the photochromic compound represented by formula (66) showed a peak attributed to the carbon of an aromatic ring around δ110 at 160 ppm, a peak attributed to the carbon of an alkene around δ80 at 140 ppm and a peak attributed to the carbon of an alkyl at δ20 at 60 ppm. Example 13 First Stage

[00333] The same reaction from the fourth step of Example 1 was performed Petition 870250084631, dated 09 / 19 / 2025, pp. 99 / 223 95 / 180 da, except that 4-bromo-4'-phenoxybenzophenone was used instead of 4-bromo-4'-methoxybenzophenone, to obtain a propargyl alcohol represented by formula (67) below with a yield of 86%. Chemical Formula 88 Second Stage

[00334] The same reaction as the second step of Example 6 was carried out, except that 4-bromo-3',4'-dimethoxybenzophenone was used instead of 3,4-dimethoxybenzophenone, 1,1,1-trifluoro-4-iodobutane was used instead of 1-bromo-4-fluorobutane, and the propargyl alcohol represented by formula (67) above was used instead of the propargyl alcohol represented by formula (52) above, to obtain a photochromic compound represented by formula (68) below with a yield of 82%. Chemical Formula 89 Third Stage

[00335] The same reaction from the third step of Example 1 was performed, except that the photochromic compound represented by the formula Petition 870250084631, dated 09 / 19 / 2025, pp. 100 / 223 96 / 180 (68) above was used instead of the naphthol derivative represented by formula (32) above and 4-trifluoromethylphenylboronic acid was used instead of 4-morpholinophenylboronic acid, to obtain a photochromic compound represented by formula (69) below with a yield of 89%. Chemical Formula 90 F

[00336] The photochromic compound represented by formula (69) above had elemental analysis values ​​of C: 71.30%, H: 4.80% and N: 1.32%, which were considerably consistent with the calculated values ​​of C62H50F9NO4 of C: 71.32%, H: 4.83% and N: 1.34%.

[00337] In a proton nuclear magnetic resonance spectroscopy, the photochromic compound represented by formula (69) showed 15H peaks attributed to a methyl group and a 1,1,1-trifluorobutyl group around δ0.5 to 3.0 ppm, a 6H peak attributed to a methoxy group around δ3.0 to 5.0 ppm and 29H peaks attributed to aromatic protons and alkene protons around δ5.0 to 9.0 ppm.

[00338] Furthermore, in a 13C nuclear magnetic resonance spectroscopy, the photochromic compound represented by formula (69) showed a peak attributed to the carbon of an aromatic ring around δ110 at 160 ppm, a peak attributed to the carbon of an al Petition 870250084631, dated 09 / 19 / 2025, pp. 101 / 223 97 / 180 cene around δ80 to 140 ppm and a peak attributed to the carbon of an alkyl group at δ20 to 60 ppm. Example 14 First Stage

[00339] The same reaction as in the fourth step of Example 1 was carried out, except that 4-bromo-3',4'-ethylenedioxybenzophenone was used instead of 4-bromo-4'-methoxybenzophenone and N-(2-methoxyethyl)aniline was used instead of N-methylaniline, to obtain a propargyl alcohol represented by formula (70) below with a yield of 86%. Chemical Formula 91 Second Stage

[00340] The same reaction as in the fifth step of Example 1 was carried out, except that a naphthol derivative represented by formula (71) below was used instead of the naphthol derivative represented by formula (33) above and propargyl alcohol represented by formula (70) above was used instead of propargyl alcohol represented by formula (35) above, to obtain a photochromic compound represented by formula (72) below with a yield of 84%. Chemical Formula 92 THE S OH (71) Petition 870250084631, dated 09 / 19 / 2025, pp. 102 / 223 98 / 180 Chemical Formula 93

[00341] The photochromic compound represented by formula (72) above had elemental analysis values ​​of C: 78.77%, H: 6.48%, N: 1.63% and S: 3.76, which were considerably consistent with the calculated values ​​of C56H55NO5S of C: 78.75%, H: 6.49%, N: 1.64% and S: 3.75%.

[00342] In a proton nuclear magnetic resonance spectroscopy, the photochromic compound represented by formula (72) showed 26H peaks attributed to a methyl group, a 2-methoxyethyl group and a spiro[5,5]undecane ring group around δ0.5 to 3.0 ppm, 9H peaks attributed to a 2-methoxyethyl group and an ethylenedioxy group around δ3.0 to 5.0 ppm and 20H peaks attributed to aromatic protons and alkene protons around δ5.0 to 9.0 ppm.

[00343] Furthermore, in a 13C nuclear magnetic resonance spectroscopy, the photochromic compound represented by formula (72) showed a peak attributed to the carbon of an aromatic ring around δ110 at 160 ppm, a peak attributed to the carbon of an alkene around δ80 at 140 ppm and a peak attributed to the carbon of an alkyl at δ20 at 60 ppm. Example 15 First Stage

[00344] The same reaction from the fifth step of Example 2 was performed Petition 870250084631, dated 09 / 19 / 2025, pp. 103 / 223 99 / 180 of, except that N-methylaniline was used instead of 4(methylamino)toluene, to obtain a propargyl alcohol represented by formula (73) below with a yield of 90%. Chemical Formula 94 OH (73) Second Stage

[00345] The same reaction as the second step of Example 6 was carried out, except that 4-bromo-3'-methyl-4'-methoxybenzophenone was used instead of 3,4-dimethoxybenzophenone, iodobutane was used instead of 1-bromo-4-fluorobutane and the propargyl alcohol represented by formula (73) above was used instead of the propargyl alcohol represented by formula (52) above, to obtain a photochromic compound represented by formula (74) below with a yield of 76%. Chemical Formula 95 Third Stage

[00346] In 35 mL of THF, 3.34 g (4.3 mmol) of the compound represented by formula (74) above were dissolved and the internal temperature was cooled to -78°C. 3.3 mL of n-BuLi (1.6 mol / L hexane solution) were slowly added to the mixture, maintaining the temperature Petition 870250084631, dated 09 / 19 / 2025, pp. 104 / 223 100 / 180 temperature at -70°C or less. After confirmation of raw material consumption, 1.5 g (6.5 mmol) of diphenylmethylchlorosilane dissolved in 10 mL of THF was slowly added to the mixture, maintaining the temperature at -70°C or less. After dropwise addition, the mixture was slowly warmed to room temperature. The mixture was stirred at room temperature for 2 hours, and then 50 mL of water and 50 mL of toluene were added to the mixture, which was subjected to liquid separation. The mixture was repeatedly washed with water until the pH of the aqueous layer reached 7 to 8. From the organic layer obtained, the solvent was removed and the organic layer was purified by silica gel chromatography to obtain a photochromic compound represented by formula (75) below with a yield of 48%. Chemical Formula 96

[00347] The photochromic compound represented by formula (75) above had elemental analysis values ​​of C: 84.59%, H: 7.11% and N: 1.55%, which were considerably consistent with the calculated CeaHeaNOzSi values ​​of C: 84.61%, H: 7.10% and N: 1.57%.

[00348] In a proton nuclear magnetic resonance spectroscopy, the photochromic compound represented by formula (75) showed 30H peaks attributed to a methyl group and a butyl group around δ0.5 to 3.0 ppm, a 3H peak attributed to a group Petition 870250084631, dated 09 / 19 / 2025, pp. 105 / 223 101 / 180 methoxy around δ3.0 to 5.0 ppm and 30H peaks attributed to aromatic protons and alkene protons around δ5.0 to 9.0 ppm.

[00349] Furthermore, in a 13C nuclear magnetic resonance spectroscopy, the photochromic compound represented by formula (75) showed a peak attributed to the carbon of an aromatic ring around δ110 at 160 ppm, a peak attributed to the carbon of an alkene around δ80 at 140 ppm and a peak attributed to the carbon of an alkyl at δ20 at 60 ppm. Example 16 First Stage

[00350] The same reaction as in the fourth step of Example 1 was carried out, except that 4-bromo-3'-methyl-4'-methoxybenzophenone was used instead of 4-bromo-4'-methoxybenzophenone, to obtain a propargyl alcohol represented by formula (76) below with a yield of 88%. Chemical Formula 97 (76) Second Stage

[00351] The same reaction as in the first step of Example 2 was carried out, except that (4-methoxyphenyl)[(4-trifluoromethoxy)phenyl] methanone was used instead of 4-bromo-4'-methoxybenzophenone, and the same reaction as in the fifth step of Example 2 was carried out, except that propargyl alcohol represented by formula (76) above was used instead of propargyl alcohol represented by formula (44) above, to obtain a photochromic compound represented by formula (77) below with a yield of 78%. Petition 870250084631, dated 09 / 19 / 2025, pp. 106 / 223 102 / 180 Chemical Formula 98

[00352] The photochromic compound represented by formula (77) above had elemental analysis values ​​of C: 77.08%, H: 6.21% and N: 1.71%, which were considerably consistent with the calculated values ​​of C52H50F3NO4 of C: 77.11%, H: 6.22% and N: 1.73%.

[00353] In a proton nuclear magnetic resonance spectroscopy, the photochromic compound represented by formula (77) showed 24H peaks attributed to a methyl group and a 4,4-diethylcyclohexyl group around δ0.5 to 3.0 ppm, a 6H peak attributed to a methoxy group around δ3.0 to 5.0 ppm and 20H peaks attributed to aromatic protons and alkene protons around δ5.0 to 9.0 ppm.

[00354] Furthermore, in a 13C nuclear magnetic resonance spectroscopy, the photochromic compound represented by formula (77) showed a peak attributed to the carbon of an aromatic ring around δ110 at 160 ppm, a peak attributed to the carbon of an alkene around δ80 at 140 ppm and a peak attributed to the carbon of an alkyl at δ20 at 60 ppm. Example 17 First Stage

[00355] The same reaction from the first step of Example 1 was performed Petition 870250084631, dated 09 / 19 / 2025, pp. 107 / 223 103 / 180, except that 3-bromo-4-methyl-4'-methylbenzophenone was used instead of 3-bromo-4-methoxybenzophenone, the same reaction as the third step of Example 1 was carried out, except that 4-methoxyphenylboronic acid was used instead of 4-morpholinophenylboronic acid, the same reaction as the fifth step of Example 1 was carried out, except that propargyl alcohol represented by formula (58) above was used instead of propargyl alcohol represented by formula (35) above, and the same reaction as the sixth step of Example 1 was carried out, except that iodoethane was used instead of iodomethane, to obtain a photochromic compound represented by formula (78) below with a yield of 70%. Chemical Formula 99

[00356] The photochromic compound represented by formula (78) above had elemental analysis values ​​of C: 79.66%, H: 6.20% and N: 1.66%, which were considerably consistent with the calculated values ​​of C56H52F3NO3 of C: 79.69%, H: 6.21% and N: 1.66%.

[00357] In a proton nuclear magnetic resonance spectroscopy, the photochromic compound represented by formula (78) showed 23H peaks attributed to a methyl group, an ethyl group, a 1,1,1-trifluoroethyl group and a propyloxy group around δ0.5 to 3.0 ppm, 5H peaks attributed to a methoxy group and a propyloxy group around δ3.0 to 5.0 ppm and 24H peaks attributed to aromatic protons and alkene protons around δ5.0 to 9.0 ppm. Petition 870250084631, dated 09 / 19 / 2025, pp. 108 / 223 104 / 180

[00358] Furthermore, in a 13C nuclear magnetic resonance spectroscopy, the photochromic compound represented by formula (78) showed a peak attributed to the carbon of an aromatic ring around δ110 at 160 ppm, a peak attributed to the carbon of an alkene around δ80 at 140 ppm and a peak attributed to the carbon of an alkyl at δ20 at 60 ppm. Example 18 First Stage

[00359] The same reaction as the first step of Example 1 was carried out, except that 3-bromo-4-methylbenzophenone was used instead of 3-bromo-4-methoxybenzophenone, the same reaction as the third step of Example 1 was carried out, except that 4-methylphenylboronic acid was used instead of 4-morpholinophenylboronic acid, the same reaction as the fifth step of Example 1 was carried out, except that propargyl alcohol represented by formula (49) above was used instead of propargyl alcohol represented by formula (35) above, and the same reaction as the sixth step of Example 1 was carried out, except that 1-iodo-2-methoxyethane was used instead of iodomethane, to obtain a photochromic compound represented by formula (79) below with a yield of 76%. Chemical Formula 100

[00360] The photochromic compound represented by formula (79) Petition 870250084631, dated 09 / 19 / 2025, pp. 109 / 223 105 / 180 above had elemental analysis values ​​of C: 85.12%, H: 7.04%, and N: 1.77%, which were considerably consistent with the calculated values ​​of C56H55NO3 of C: 85.13%, H: 7.02%, and N: 1.77%.

[00361] In a proton nuclear magnetic resonance spectroscopy, the photochromic compound represented by formula (79) showed 20H peaks attributed to a methyl group, a propyl group and a 2-methoxyethyl group around δ0.5 to 3.0 ppm, a 10H peak attributed to a 2-methoxyethyl group around δ3.0 to 5.0 ppm and 25H peaks attributed to aromatic protons and alkene protons around δ5.0 to 9.0 ppm.

[00362] Furthermore, in a 13C nuclear magnetic resonance spectroscopy, the photochromic compound represented by formula (79) showed a peak attributed to the carbon of an aromatic ring around δ110 at 160 ppm, a peak attributed to the carbon of an alkene around δ80 at 140 ppm and a peak attributed to the carbon of an alkyl at δ20 at 60 ppm. Example 19

[00363] The same reaction as in the third step of Example 1 was carried out, except that 2,4-dimethoxyphenylboronic acid was used instead of 4-morpholinophenylboronic acid, the same reaction as in the fifth step of Example 1 was carried out, except that propargyl alcohol represented by formula (73) above was used instead of propargyl alcohol represented by formula (35) above, and the same reaction as in the sixth step of Example 1 was carried out, except that iodopropane was used instead of iodomethane, to obtain a photochromic compound represented by formula (80) below with a yield of 72%. Petition 870250084631, dated 09 / 19 / 2025, pp. 110 / 223 106 / 180 Chemical Formula 101

[00364] The photochromic compound represented by formula (80) above had elemental analysis values ​​of C: 83.39%, H: 6.75% and N: 1.78%, which were considerably consistent with the calculated values ​​of C55H53NO4 of C: 83.41%, H: 6.74% and N: 1.77%.

[00365] In a proton nuclear magnetic resonance spectroscopy, the photochromic compound represented by formula (80) showed 20H peaks attributed to a methyl group and a propyl group around δ0.5 to 3.0 ppm, a 9H peak attributed to a methoxy group around δ3.0 to 5.0 ppm and 24H peaks attributed to aromatic protons and alkene protons around δ5.0 to 9.0 ppm.

[00366] Furthermore, in a 13C nuclear magnetic resonance spectroscopy, the photochromic compound represented by formula (80) showed a peak attributed to the carbon of an aromatic ring around δ110 at 160 ppm, a peak attributed to the carbon of an alkene around δ80 at 140 ppm and a peak attributed to the carbon of an alkyl at δ20 at 60 ppm. Example 20

[00367] The same reaction as in the second step of Example 13 was carried out, except that 1-iodo-3-methoxypropane was used instead of 1,1,1-trifluoro-4-iodobutane and the propargyl alcohol represented by formula (70) above was used instead of the propargyl alcohol represented by Petition 870250084631, dated 09 / 19 / 2025, pp. 111 / 223 107 / 180 formula (67) above, and the same reaction as the third step of Example 13 was carried out, except that 4-t-butylphenylboronic acid was used instead of 4-trifluoromethylphenylboronic acid, to obtain a photochromic compound represented by formula (81) below with a yield of 75%. Chemical Formula 102

[00368] The photochromic compound represented by formula (81) above had elemental analysis values ​​of C: 78.32%, H: 7.00% and N: 1.44%, which were considerably consistent with the calculated CeaHeyNOs values ​​of C: 78.31%, H: 6.99% and N: 1.45%.

[00369] In a proton nuclear magnetic resonance spectroscopy, the photochromic compound represented by formula (81) showed 19H peaks attributed to a t-butyl group, a 3-methoxypropyl group and a 2-methoxyethyl group around δ0.5 to 3.0 ppm, 25H peaks attributed to a methoxy group, a 3-methoxypropyl group, a 2-methoxyethyl group and an ethylenedioxy group around δ3.0 to 5.0 ppm, and 23H peaks attributed to aromatic protons and alkene protons around δ5.0 to 9.0 ppm.

[00370] Furthermore, in a 13C nuclear magnetic resonance spectroscopy, the photochromic compound represented by the formula Petition 870250084631, dated 09 / 19 / 2025, pp. 112 / 223 108 / 180 mula (81) showed a peak attributed to the carbon of an aromatic ring around δ110 at 160 ppm, a peak attributed to the carbon of an alkene around δ80 at 140 ppm and a peak attributed to the carbon of an alkyl at δ20 at 60 ppm. Example 21 First Stage

[00371] The same reaction as in the second step of Example 11 was carried out, except that propargyl alcohol represented by formula (54) above was used instead of propargyl alcohol represented by formula (63) above and iodobutane was used instead of 1-bromo-4-methoxybutane, to synthesize a photochromic compound represented by formula (82) below. Chemical Formula 103 Br / — Second Stage

[00372] The same reaction as in the third step of Example 1 was carried out, except that the photochromic compound represented by formula (82) above was used instead of the naphthol derivative represented by formula (32) above and 4-isopropoxyphenylboronic acid was used instead of 4-morpholinophenylboronic acid, to obtain a photochromic compound represented by formula (83) below with a yield of 89%. Petition 870250084631, dated 09 / 19 / 2025, pp. 113 / 223 109 / 180 Chemical Formula 104

[00373] The photochromic compound represented by formula (83) above had elemental analysis values ​​of C: 81.77%, H: 6.85% and N: 1.64%, which were considerably consistent with the calculated values ​​of C58H58FNO4 of C: 81.75%, H: 6.86% and N: 1.64%.

[00374] In a proton nuclear magnetic resonance spectroscopy, the photochromic compound represented by formula (83) showed 27H peaks attributed to a butyl group, a methyl group and an isopropoxy group around δ0.5 to 3.0 ppm, 7H peaks attributed to a methoxy group and an isopropoxy group around δ3.0 to 5.0 ppm and 24H peaks attributed to aromatic protons and alkene protons around δ5.0 to 9.0 ppm.

[00375] Furthermore, in a 13C nuclear magnetic resonance spectroscopy, the photochromic compound represented by formula (83) showed a peak attributed to the carbon of an aromatic ring around δ110 at 160 ppm, a peak attributed to the carbon of an alkene around δ80 at 140 ppm and a peak attributed to the carbon of an alkyl at δ20 at 60 ppm. Example 22 First Stage Petition 870250084631, dated 09 / 19 / 2025, pp. 114 / 223 110 / 180

[00376] The same reaction as in the third step of Example 2 was carried out, except that 4-heptanone was used instead of 4,4-diethylcyclohexanone, and the same reaction as in the sixth step of Example 2 was carried out, except that propargyl alcohol represented by formula (73) above was used instead of propargyl alcohol represented by formula (44) above, to obtain a photochromic compound represented by formula (84) below with a yield of 86%. Chemical Formula 105

[00377] The photochromic compound represented by formula (84) above had elemental analysis values ​​of C: 86.08%, H: 6.61% and N: 3.41%, which were considerably consistent with the calculated values ​​of C59H54N2O2 of C: 86.10%, H: 6.61% and N: 3.40%.

[00378] In a proton nuclear magnetic resonance spectroscopy, the photochromic compound represented by formula (84) showed 20H peaks attributed to a methyl group and a propyl group around δ0.5 to 3.0 ppm, a 3H peak attributed to a methoxy group around δ3.0 to 5.0 ppm and 31H peaks attributed to aromatic protons and alkene protons around δ5.0 to 9.0 ppm.

[00379] Furthermore, in a 13C nuclear magnetic resonance spectroscopy, the photochromic compound represented by formula (84) showed a peak attributed to the carbon of an aromatic ring around δ110 at 160 ppm, a peak attributed to the carbon of an al Petition 870250084631, dated 09 / 19 / 2025, pp. 115 / 223 111 / 180 cene around δ80 to 140 ppm and a peak attributed to the carbon of an alkyl group at δ20 to 60 ppm. Example 23

[00380] The same reaction as in the third step of Example 1 was carried out, except that 4-diphenylaminophenylboronic acid was used instead of 4-morpholinophenylboronic acid, the same reaction as in the fifth step of Example 1 was carried out, except that propargyl alcohol represented by formula (67) above was used instead of propargyl alcohol represented by formula (35) above, and the same reaction as in the sixth step of Example 1 was carried out, except that 1-iodo-2-methoxyethane was used instead of iodomethane, to obtain a photochromic compound represented by formula (85) below with a yield of 71%. Chemical Formula 106

[00381] The photochromic compound represented by formula (85) above had elemental analysis values ​​of C: 83.33%, H: 5.98% and N: 2.76%, which were considerably consistent with the calculated values ​​of C70H60N2O5 of C: 83.31%, H: 5.99% and N: 2.78%.

[00382] In a proton nuclear magnetic resonance spectroscopy, the photochromic compound represented by formula (85) showed 7H peaks attributed to a methyl group and a 2-methoxyethyl group around δ0.5 to 3.0 ppm, 13H peaks attributed to a methoxy group and a 2-methoxyethyl group around δ3.0 to 5.0 ppm and Petition 870250084631, dated 09 / 19 / 2025, pp. 116 / 223 112 / 180 peaks of 40H attributed to aromatic protons and alkene protons around δ5.0 to 9.0 ppm.

[00383] Furthermore, in a 13C nuclear magnetic resonance spectroscopy, the photochromic compound represented by formula (85) showed a peak attributed to the carbon of an aromatic ring around δ110 at 160 ppm, a peak attributed to the carbon of an alkene around δ80 at 140 ppm and a peak attributed to the carbon of an alkyl at δ20 at 60 ppm. Example 24

[00384] The same reaction as in the third step of Example 1 was carried out, except that 4-methylphenylaminophenylboronic acid was used instead of 4-morpholinophenylboronic acid, the same reaction as in the fifth step of Example 1 was carried out, except that propargyl alcohol represented by formula (73) above was used instead of propargyl alcohol represented by formula (35) above, and the same reaction as in the sixth step of Example 1 was carried out, except that iodopropane was used instead of iodomethane, to obtain a photochromic compound represented by formula (86) below with a yield of 77%. Chemical Formula 107

[00385] The photochromic compound represented by formula (86) above had elemental analysis values ​​of C: 86.09%, H: 6.75% and N: 3.33%, which were considerably consistent with the values ​​of Petition 870250084631, dated 09 / 19 / 2025, pp. 117 / 223 113 / 180 cells of C60H56N2O2 of C: 89.09%, H: 6.74% and N: 3.35%.

[00386] In a proton nuclear magnetic resonance spectroscopy, the photochromic compound represented by formula (86) showed 23H peaks attributed to a methyl group and a propyl group around δ0.5 to 3.0 ppm, a 3H peak attributed to a methoxy group around δ3.0 to 5.0 ppm and 30H peaks attributed to aromatic protons and alkene protons around δ5.0 to 9.0 ppm.

[00387] Furthermore, in a 13C nuclear magnetic resonance spectroscopy, the photochromic compound represented by formula (86) showed a peak attributed to the carbon of an aromatic ring around δ110 at 160 ppm, a peak attributed to the carbon of an alkene around δ80 at 140 ppm and a peak attributed to the carbon of an alkyl at δ20 at 60 ppm. Example 25 First Stage

[00388] The same reaction as in the fourth step of Example 1 was carried out, except that N-ethyl-4-methoxyaniline was used instead of N-methylaniline, to obtain a propargyl alcohol represented by formula (87) below with a yield of 89%. Chemical Formula 108 Second Stage

[00389] The same reaction as in the fifth step of Example 1 was carried out, except that propargyl alcohol represented by formula (87) above was used instead of propargyl alcohol represented by formula (35) above, to obtain a photochromic compound represented by formula (88) below with a yield of 81%. Petition 870250084631, dated 09 / 19 / 2025, pp. 118 / 223 114 / 180 Chemical Formula 109

[00390] The photochromic compound represented by formula (88) above had elemental analysis values ​​of C: 80.44%, H: 6.38% and N: 3.42%, which were considerably consistent with the calculated values ​​of C55H52N2O5 of C: 80.46%, H: 6.38% and N: 3.41%.

[00391] In a proton nuclear magnetic resonance spectroscopy, the photochromic compound represented by formula (88) showed 15H peaks attributed to a methyl group, an ethyl group and a morpholino group around δ0.5 to 3.0 ppm, 13H peaks attributed to a methoxy group and a morpholino group around δ3.0 to 5.0 ppm and 24H peaks attributed to aromatic protons and alkene protons around δ5.0 to 9.0 ppm.

[00392] Furthermore, in a 13C nuclear magnetic resonance spectroscopy, the photochromic compound represented by formula (88) showed a peak attributed to the carbon of an aromatic ring around δ110 at 160 ppm, a peak attributed to the carbon of an alkene around δ80 at 140 ppm and a peak attributed to the carbon of an alkyl at δ20 at 60 ppm. Evaluation of Physical Properties of Photochromic Plastic Lenses Prepared by the Coating Method Example 26 Preparation of the Curable Composition

[00393] First, the photochromic compound obtained in Example 1, a Petition 870250084631, dated 09 / 19 / 2025, pp. 119 / 223 115 / 180 photoinitiator and a polymerizable compound were mixed to obtain a curable composition.

[00394] As a polymerizable compound, a combination of the following radically polymerizable monomers was used.

[00395] Polyethylene glycol dimethacrylate (average molecular weight: 736): 42 parts by mass

[00396] Polyethylene glycol dimethacrylate (average molecular weight: 536): 12 parts by mass

[00397] Trimethylolpropane trimethacrylate: 38 parts by mass

[00398] γ-Methacryloyloxypropyl trimethoxysilane: 2 parts by mass

[00399] Glycidyl methacrylate: 1 part by mass

[00400] Note that the photochromic compound was added to the curable composition such that the amount of photochromic compound was 0.25 mmol based on 100 g of the total amount of polymerizable monomers per radical.

[00401] The following additives were used.

[00402] Phenylbis (2,4,6-trimethylbenzoyl)phosphine (photoinitiator: Omnirad 819): 0.3 parts by mass

[00403] Ethylene bis(oxyethylene) bis[3-(5-tert-butyl-4-hydroxy-methyltolyl)propionate] (stabilizer, Irganox 245): 1 part by mass

[00404] Bis(1,2,2,6,6-pentamethyl-4-piperidyl) sebacate: 3 parts by mass

[00405] Leveling agent (L7001) manufactured by Dow Corning Toray Co., Ltd.: 0.1 part by mass

[00406] Note that each composition ratio of the additives above is based on 100 parts by mass of the total amount of polymerizable monomers per radical. Production of Optical Articles

[00407] This curable composition was subjected to a lamination method using polymerization to obtain a photo laminate. Petition 870250084631, dated 09 / 19 / 2025, pages 120 / 223 116 / 180 chromic, as described below.

[00408] First, a thiourethane-based plastic lens, with a central thickness of 2 mm and a refractive index of 1.60, was prepared as an optical substrate. Note that this thiourethane-based plastic lens was pre-treated by alkaline chemical etching with a 10% aqueous sodium hydroxide solution at 50°C for 5 minutes, followed by sufficient washing with distilled water.

[00409] A plastic lens surface described above was coated with a moisture-curable primer (product name: TR-SCP, manufactured by Tokuyama Corporation) at a rotational frequency of 70 rpm for 15 seconds, followed by 1000 rpm for 10 seconds, using a centrifugal coating machine (1H-DX2, manufactured by MIKASA CO., LTD).

[00410] Subsequently, approximately 2 g of the curable photochromic composition obtained above was coated by centrifugation at a rotation frequency of 60 rpm for 40 seconds, followed by 600 rpm for 10 to 20 seconds, to form a photochromic coating layer with a film thickness of 40 μm.

[00411] The lens with the surface coated with the curable photochromic composition (photochromic coating layer) was irradiated with light using a metal halide lamp with an output power of 200 mW / cm2 in a nitrogen gas atmosphere for 90 seconds to cure the coating film. Subsequently, the lens was heated again to 110°C for 1 hour to prepare a photochromic laminate with a photochromic layer. Examples 27 to 50

[00412] As in Example 26, photochromic laminates were prepared using the photochromic compounds obtained in Examples 2 to 25. Comparative examples 1 to 8 Petition 870250084631, dated 09 / 19 / 2025, pp. 121 / 223 117 / 180

[00413] In the same way as in Example 26, each photochromic laminate was obtained using each of the photochromic compounds represented by formulas (A) to (H) below. Chemical Formula 110 OMe V 0 1 Chemical Formula 111 JCJ ° / - J OMe V 1 Jl on Q- Chemical Formula 112 OMe γ G α ^\>3Me ) (A) ^\>3Me j] (B) ^X)Me j] (C) c Petition 870250084631, dated 09 / 19 / 2025, pp. 122 / 223 118 / 180 Chemical Formula 113 (D) Chemical Formula 114 (F) Petition 870250084631, dated 09 / 19 / 2025, pp. 123 / 223 119 / 180 Chemical Formula 117 Synthesis of Compound A

[00414] The same reaction as in Example 1 was carried out, except that 4-dimethylamino-4'-methoxybenzophenone was used instead of benzophenone represented by formula (34) above. Synthesis of Compound B

[00415] The same reaction as in Example 1 was carried out, except that 4-diphenylamino-4'-methoxybenzophenone was used instead of benzophenone represented by formula (34) above. Synthesis of Compound C

[00416] The same reaction as in Example 1 was carried out, except that [4(9H-carbazol-9-yl)phenyl]-(4-methoxyphenyl) methanone was used instead of benzophenone represented by formula (34) above. Synthesis of Compound D

[00417] The same reaction as in Example 1 was carried out, except that 4-phenoxy-4'-methoxybenzophenone was used instead of benzophenone represented by formula (34) above. Petition 870250084631, dated 09 / 19 / 2025, pp. 124 / 223 120 / 180 Synthesis of Compound E

[00418] The same reaction as in Example 1 was carried out, except that (4-methoxyphenyl)-(4-phenylsulfanylphenyl) methanone was used instead of benzophenone represented by formula (34) above. Synthesis of Compound F

[00419] The same reaction as in Example 1 was carried out, except that 4-methoxyphenyl)-[(4-morpholin-1-yl)phenyl] methanone was used instead of benzophenone represented by formula (34) above. Synthesis of Compound G

[00420] The same reaction as in Example 1 was carried out, except that (4-methoxyphenyl)-[(4-piperidine-1-yl)phenyl] methanone was used instead of benzophenone represented by formula (34) above. Synthesis of Compound H

[00421] The same reaction as in Example 1 was carried out, except that 4-methoxy-4'-methylbenzophenone was used instead of benzophenone represented by formula (34) above. Evaluation Method

[00422] The photochromic slides obtained were evaluated using the method described below. (1) Photochromic properties

[00423] [1] Wavelength of maximum absorption (Àmax):

[00424] The maximum absorption wavelength after color development, measured using a spectrophotometer (MCPD3000 instant multichannel photodetector) manufactured by Otsuka Electronics Co., Ltd., was used as an indicator of color tone during color development.

[00425] [2] Optical color density 23°C (A23):

[00426] The difference between the absorbance measured after light irradiation at 23°C for 300 seconds {ε(300)} and the absorbance without light irradiation ε(0) at the maximum absorption wavelength was Petition 870250084631, dated 09 / 19 / 2025, pages 125 / 223 121 / 180 is used as an indicator of the optical density of color. It is considered that the higher this value, the superior the photochromic property.

[00427] [3] Color fading half-life at 23°C [τ1 / 2 (sec.)]:

[00428] The time required for the sample absorbance at the maximum absorption wavelength to decrease to 1 / 2 of {ε(300)-ε(0)} when light irradiation was stopped after 300 seconds at 23°C was used as an indicator of the color fading rate. The shorter this time, the greater the color fading rate.

[00429] [4] Residual Rate (A120 / A0 χ100): The obtained photochromic plastic lens was subjected to accelerated deterioration using an X25 xenon time meter manufactured by Suga Test Instruments Co., Ltd. for 120 hours. Subsequently, the optical color density was evaluated before and after the test, then an optical color density before the test (A0) and an optical color density after the test (A120) were measured, and a ratio (A120 / A0) was defined as a residual rate. The residual rate was used as an indicator for color development durability. The higher the residual rate, the greater the color development durability. The results of Examples 26, 50 and Comparative Examples 1 to 8 are summarized in Table 1, and the results of Examples 27 to 49 are summarized in Tables 2 and 3. Table 1 Compound No. Wavelength of maximum absorption (nm) A23 (-) Color fading half-life at 23°C (sec) Residual rate (%) Example 26 Example 1 502 1.09 76 65% Formula (37) 601 1.09 77 65% Example 50 Example 25 505 0.84 68 63% Formula (88) 605 0.94 68 63% Petition 870250084631, dated 09 / 19 / 2025, pp. 126 / 223 122 / 180 Compound No. Maximum Absorption Wavelength (nm) A23 (-) Color Fading Half-Life at 23°C (sec) Residual Rate (%) Ex. Comparative Formula(A) 503 0.89 57 43% Ex. Comparative Formula(B) 504 1.29 189 56% Ex. Comparative Formula(C) 475 1.61 393 33% Ex. Comparative Formula(D) 468 1.36 174 59% Ex. Comparative Formula(E) 558 0.97 178 59% Ex. Comparative Formula(E) 479 1.28 187 55% 560 0.92 188 54% Ex. Comparative Formula(F) 490 1.10 89 54% Ex. Comparative Formula(G) 500 1.02 74 48% Ex. Comparative Formula(H) 7 595 1.05 75 48% Ex. Comparative Formula(H) 471 1.34 202 57% 8 554 0.94 204 57% Table 2 Compound No. Wavelength of maximum absorption (nm) A23 (-) Color fading half-life at 23°C (sec) Residual rate (%) Example 27 Example 2 Formula (45) 522 1.36 73 67% Example 28 Example 3 Formula (46) 470 612 0.57 1.14 71 71 55% 55% Example 29 Example 4 Formula (48) 489 601 0.59 1.05 90 88 57% 57% Petition 870250084631, dated 09 / 19 / 2025, pages 127 / 223 123 / 180 Compound No. Wavelength of maximum absorption (nm) A23 (-) Color fading half-life at 23°C (sec) Residual rate (%) Example 30 Example 5 509 0.54 48 68% 68% Formula (51) 591 0.66 47 Example 31 Example 6 481 0.69 59 70% 63% Formula (53) 593 0.72 60 Example 32 Example 7 496 0.72 70 61% 61% Formula (55) 603 0.96 70 Example 33 Example 8 474 0.49 74 60% 60% Formula (57) 597 1.19 74 Example 34 Example 9 Formula (60) 578 0.94 36 62% Example 35 Example 10 512 1.35 117 60% 64% Formula (62) 598 1.08 115 Example 36 Example 11 477 0.48 38 60% 60% Formula (65) 614 0.95 38 Example 37 Example 12 478 0.80 78 65% 65% Formula (66) 614 1.07 78 Example 38 Example 13 489 0.86 62 65% 60% Formula (69) 605 0.94 63 Table 3 Compound No. Wavelength of maximum absorption (nm) A23 (-) Color fading half-life at 23°C (sec) Residual rate (%) Example 39 Example 14 492 056 52 63% Formula (72) 586 0.64 52 63% Example 40 Example 15 487 0.89 113 58% Formula (75) 602 1.25 112 58% Petition 870250084631, dated 09 / 19 / 2025, pp. 128 / 223 124 / 180 Compound No. Wavelength of maximum absorption (nm) A23 (-) Color fading half-life at 23°C (sec) Residual rate (%) Example 41 Example 16 472 0.44 48 57% Formula (77) 584 0.85 48 57% Example 42 Example 17 484 0.54 48 56% Formula (78) 592 1.05 49 56% Example 43 Example 18 Formula (79) 587 1.12 48 60% 60% Example 44 Example 19 494 0.84 93 64% Formula (80) 604 1.12 93 64% Example 45 Example 20 486 0.75 77 67% Formula (81) 608 0.85 76 63% Example 46 Example 21 489 0.57 72 60% Formula (83) 609 1.21 71 60% Example 47 Example 22 Formula (84) 530 1.51 75 68% Example 48 Example 23 506 0.99 48 60% Formula (85) 609 1.04 48 60% Example 49 Example 24 Formula (86) 504 599 1.27 1.27 89 90 62% 62% Example 51 First Stage

[00430] The same reaction as in the first step of Example 1 was carried out, except that (3,4-dimethoxyphenyl)-[4-(trifluoromethyl)phenyl] methanone was used instead of 3-bromo-4-methoxybenzophenone, and the same reaction as in the sixth step of Example 1 was carried out, except that 13-bromo2,5,8,11-tetraoxatridecane was used instead of iodomethane, to obtain a photochromic compound represented by formula (89) below with a yield of 61%. Petition 870250084631, dated 09 / 19 / 2025, pp. 129 / 223 125 / 180 Chemical Formula 118 (89)

[00431] The photochromic compound represented by formula (89) above had elemental analysis values ​​of C: 68.70%, H: 6.61% and N: 1.31%, which were considerably consistent with the calculated values ​​of C61H70F3NO12 of C: 68.72%, H: 6.62% and N: 1.31%. In a proton nuclear magnetic resonance spectroscopy, the photochromic compound represented by formula (89) showed 7H peaks attributed to a methyl group and a 2,5,8,11-tetraoxatridecane group around δ0.5 to 3.0 ppm, 43H peaks attributed to a methoxy group and a 2,5,8,11-tetraoxatridecane group around δ3.0 to 5.0 ppm and 20H peaks attributed to aromatic protons and alkene protons around δ5.0 to 9.0 ppm.Furthermore, in a 13C nuclear magnetic resonance spectroscopy, the photochromic compound represented by formula (89) showed a peak attributed to the carbon of an aromatic ring around δ110 at 160 ppm, a peak attributed to the carbon of an alkene around δ80 at 140 ppm and a peak attributed to the carbon of an alkyl at δ20 at 60 ppm. Example 52 First Stage

[00432] Referring to the method described in the Patent Document Petition 870250084631, dated 09 / 19 / 2025, pp. 130 / 223 126 / 180 8, the same reaction as in Example 2 was carried out, except that a benzophenone represented by formula (90) below obtained by the reaction of 4-bromobenzoyl chloride with 2,2-dimethyl-1,3-benzothiol was used to synthesize a carboxylic acid compound represented by formula (91) below. Chemical Formula 119 (90) Second Stage (91)

[00433] The same reaction as in the third step of Example 1 was carried out, except that the compound represented by formula (91) above was used instead of the compound represented by formula (32) above and (2,3,4-trifluorophenyl)boronic acid was used instead of 4-morpholinophenylboronic acid, to synthesize a carboxylic acid compound represented by formula (92) below with a yield of 91%. Petition 870250084631, dated 09 / 19 / 2025, pp. 131 / 223 127 / 180 Third Stage

[00434] The same reaction as the second step of Example 2 was carried out, except that the compound represented by formula (92) above was used instead of the compound represented by formula (39) above, the same reaction as the third step of Example 2 was carried out, except that cyclododecanone was used instead of 4,4-diethylcyclohexanone, and the same reaction as the fifth step of Example 2 was carried out, except that propargyl alcohol represented by formula (35) above was used instead of propargyl alcohol represented by formula (44) above, to obtain a photochromic compound represented by formula (93) below with a yield of 56%. Chemical Formula 122

[00435] The photochromic compound represented by formula (93) Petition 870250084631, dated 09 / 19 / 2025, pp. 132 / 223 128 / 180 above had elemental analysis values ​​of C: 76.30%, H: 5.96%, N: 1.47%, and S: 6.80%, which were considerably consistent with the calculated values ​​of C60H56F3NO2S2 of C: 76.32%, H: 5.98%, N: 1.48%, and S: 6.79%. In a proton nuclear magnetic resonance spectroscopy, the photochromic compound represented by formula (93) showed 31H peaks attributed to a methyl group and a cyclododecanone ring group around δ0.5 to 3.0 ppm, a 3H peak attributed to a methoxy group around δ3.0 to 5.0 ppm and 22H peaks attributed to aromatic protons and alkene protons around δ5.0 to 9.0 ppm. Furthermore, in a 13C nuclear magnetic resonance spectroscopy, the photochromic compound represented by formula (93) showed a peak attributed to the carbon of an aromatic ring around δ110 at 160 ppm, a peak attributed to the carbon of an alkene around δ80 at 140 ppm and a peak attributed to the carbon of an alkyl at δ20 at 60 ppm. Example 53 First Stage

[00436] The same reaction as in the fifth step of Example 1 was carried out, except that the naphthol compound represented by formula (32) above was used instead of the naphthol compound represented by formula (33) above and the propargyl alcohol represented by formula (54) above was used instead of the propargyl alcohol represented by formula (35) above, and the same reaction as in the sixth step of Example 1 was carried out, except that 1-(2-iodoetoxic)butane was used instead of iodomethane, to obtain a photochromic compound represented by formula (94) below with a yield of 64%. Chemical Formula 123 Petition 870250084631, dated 09 / 19 / 2025, pp. 133 / 223 129 / 180 Second Stage

[00437] Using the method described in Patent Document 11, the photochromic compound represented by formula (94) above was reacted with benzamide. After the reaction, the reagent was purified by silica gel chromatography to obtain a photochromic compound represented by formula (95) below, with a yield of 64%. Chemical Formula 124

[00438] The photochromic compound represented by formula (95) above showed elemental analysis values ​​of C: 77.88%, H: 6.65% and N: 3.02%, which were considerably consistent with the calculated values ​​of C60H61FN2O6 of C: 77.90%, H: 6.65% and N: 3.03%. In a proton nuclear magnetic resonance spectroscopy, the photochromic compound represented by formula (95) showed 21H peaks attributed to a methyl group and an ethylbutoxy group around δ0.5 to 3.0 ppm, 15H peaks attributed to a methoxy group, Petition 870250084631, dated 09 / 19 / 2025, pp. 134 / 223 130 / 180 an ethylbutoxy group and an amide group around δ3.0 to 5.0 ppm, and 25H peaks attributed to aromatic protons and alkene protons around δ5.0 to 9.0 ppm. Furthermore, in a 13C nuclear magnetic resonance spectroscopy, the photochromic compound represented by formula (95) showed a peak attributed to the carbon of an aromatic ring around δ110 to 160 ppm, a peak attributed to the carbon of an alkene around δ80 to 140 ppm and a peak attributed to the carbon of an alkyl at δ20 to 60 ppm. Example 54 First Stage

[00439] The same reaction as in the first step of Example 12 was carried out, except that 3-bromo-4-methoxy-4'-methoxybenzophenone was used instead of 3-bromo-4-methoxy-4'-methylbenzophenone, 4-thiomorpholinophenylboronic acid was used instead of 2,4,6-trimethoxyphenylboronic acid and 1,1,1-trifluoro-3-iodopropane was used instead of 1-bromo-3-methylthiopropane, to obtain a photochromic compound represented by formula (96) below with a yield of 55%. Chemical Formula 125

[00440] The photochromic compound represented by formula (96) above had elemental analysis values ​​of C: 70.55%, H: 5.30%, N: 2.85% and S: 3.24%, which were considerably consistent with the calculated values ​​of C58H52F6N2O4 S of C: 70.57%, H: 5.31%, N: 2.84% and S: 3.25%. In a magnetic resonance spectroscopy Petition 870250084631, dated 09 / 19 / 2025, pages 135 / 223 131 / 180 nuclear protons, the photochromic compound represented by formula (96) showed 19H peaks attributed to a methyl group, a 1,1,1-trifluoropropyl group and a thiomorpholino group around δ0.5 to 3.0 ppm, a 9H peak attributed to a methoxy group around δ3.0 to 5.0 ppm and 24H peaks attributed to aromatic protons and alkene protons around δ5.0 to 9.0 ppm. Furthermore, in a 13C nuclear magnetic resonance spectroscopy, the photochromic compound represented by formula (96) showed a peak attributed to the carbon of an aromatic ring around δ110 at 160 ppm, a peak attributed to the carbon of an alkene around δ80 at 140 ppm and a peak attributed to the carbon of an alkyl at δ20 at 60 ppm. Example 55 First Stage

[00441] In 200 mL of dimethylformamide, 27.7 g (100.1 mmol) of (4-chlorophenyl)[4-(2-hydroxyethoxy)phenyl] methanone and 15.0 g (220.2 mmol) of imidazole were dissolved, and the internal temperature was cooled to 2°C. 80 mL of dimethylformamide containing 16.6 g (110.1 mmol) of tert-butyldimethylchlorosilane were added to the mixture, maintaining the internal temperature at 5°C or less. The mixture was stirred at 5°C or less until the raw materials were consumed, and then 300 mL of toluene and 150 mL of water were added to the mixture, which was subjected to liquid separation. To the mixture, 300 mL of water were added, and liquid separation was repeated twice. The organic layer obtained was concentrated and then purified by silica gel chromatography to obtain a benzophenone compound represented by formula (97) below with a yield of 94%. Chemical Formula 126 Petition 870250084631, dated 09 / 19 / 2025, pp. 136 / 223 132 / 180 Second Stage

[00442] The same reaction as in the fourth step of Example 1 was carried out, except that the compound represented by formula (97) above was used instead of 4-bromo-4'-methoxybenzophenone, to obtain a propargyl alcohol represented by formula (98) below with a yield of 80%. Chemical Formula 127 (98) Third Stage

[00443] The same reaction as in the first step of Example 2 was carried out, except that 3-bromo-4-methoxy-4'-methylbenzophenone was used instead of 3-bromo-4-methoxybenzophenone and benzomorpholine was used instead of diphenylamine, the same reaction as in the third step of Example 2 was carried out, except that diethyl ketone was used instead of diethylcyclohexanone, and the same reaction as in the fifth step of Example 2 was carried out, except that the propargyl alcohol represented by formula (98) above was used instead of the propargyl alcohol represented by formula (44) above, to obtain a compound represented by formula (99) below with a yield of 58%. Chemical Formula 128 (99) Fourth Stage Petition 870250084631, dated 09 / 19 / 2025, pp. 137 / 223 133 / 180

[00444] In 25 mL of THF, 4.88 g (5.3 mmol) of the compound represented by formula (99) above were dissolved and the internal temperature was cooled to 3°C. 6 mL of tetrabutylammonium fluoride (1.0 mol / L THF solution) were added to the mixture. The mixture was stirred at an internal temperature of 5°C or less and, after confirmation of the consumption of the raw materials, 20 mL of water and 20 mL of toluene were added to the mixture, which was subjected to liquid separation. Liquid separation was repeated until the pH of the aqueous layer reached approximately 7. The organic layer obtained was concentrated and then purified by silica gel chromatography to obtain a compound represented by formula (100) below, with a yield of 97%. Chemical Formula 129 Fifth Stage

[00445] Referring to the method described in Patent Document 12, a compound represented by formula (101) below synthesized from polytramethylene glycol with a number average molecular weight of 1000 was reacted with the compound represented by formula (100) above to obtain the photochromic compound represented by formula (102) below with a yield of 79%. Chemical Formula 130 oO ClX^^ / Yl·^ ^\ / Ol(101) Or^^ OO Petition 870250084631, dated 09 / 19 / 2025, pp. 138 / 223 134 / 180 Chemical Formula 131

[00446] In a proton nuclear magnetic resonance spectroscopy, the photochromic compound represented by formula (102) above showed peaks of about 100H attributed to a methyl group, an ethyl group, a benzmorpholine group, a succinic acid group and a polytramethylene glycol chain group around δ0.5 to 3.0 ppm, peaks of about 74H attributed to a methoxy group, an ethylene glycol group, a polytramethylene glycol chain group and a benzmorpholine group around δ3.0 to 5.0 ppm and peaks of 48H attributed to aromatic protons and alkene protons around δ5.0 to 9.0 ppm. Example 56 First Stage

[00447] The same reaction as in the first step of Example 55 was carried out, except that (4-chlorophenyl)[4-(2-hydroxyethyl)phenyl] methanone was used instead of (4-chlorophenyl)[4-(2-hydroxyethoxy)phenyl] methanone, and the same reaction as in the second step of Example 55 was carried out, except that 4-methoxy-N-methylaniline was used instead of N-methylaniline, to obtain a propargyl alcohol represented by formula (103) below. Chemical Formula 132 Second Stage

[00448] The same reaction as in Example 3 was performed, except that (4-methoxyphenyl)(4-phenoxyphenyl) methanone was used instead of 4,4' Petition 870250084631, dated 09 / 19 / 2025, pp. 139 / 223 135 / 180 dimethoxybenzophonene, 1-iodo-3-methoxypropane was used instead of iodopropane, and propargyl alcohol represented by formula (103) above was used instead of propargyl alcohol represented by formula (35) above, to obtain a compound represented by formula (104) below with a yield of 75%. Chemical Formula 133 (104)

[00449] The same reaction as in the fourth step of Example 55 was carried out, except that the compound represented by formula (104) above was used instead of the compound represented by formula (99) above, and the same reaction as in the fifth step of Example 55 was carried out, except that polypropylene glycol monobutyl ether with a number average molecular weight of 1250 was used instead of polytramethylene glycol with a number average molecular weight of 1000, to obtain a photochromic compound represented by formula (105) below with a yield of 81%. Petition 870250084631, dated 09 / 19 / 2025, pp. 140 / 223 136 / 180 Chemical Formula 134

[00450] In a proton nuclear magnetic resonance spectroscopy, the photochromic compound represented by formula (105) above showed peaks of about 84H attributed to a methyl group, a 3-methoxypropyl group, an ethyl group, a succinic acid group, a polypropylene glycol chain group and a butyl group around δ0.5 to 3.0 ppm, peaks of about 80H attributed to a methoxy group, a 3-methoxypropyl group, an ethyloxy group, a polypropylene glycol chain group and a butyloxy group around δ3.0 to 5.0 ppm, and peaks of 25H attributed to aromatic protons and alkene protons around δ5.0 to 9.0 ppm. Example 57 First Stage

[00451] Referring to the method described in Patent Document 8, the same reaction as in Example 1 was carried out, except that a compound represented by formula (106) below obtained by the reaction of 2-bromoanisole with 4-trifluoromethoxybenzoyl chloride was used to synthesize a naphthol derivative represented by formula (107) below. Petition 870250084631, dated 09 / 19 / 2025, pp. 141 / 223 137 / 180

[00452] The same reaction as in the fifth step of Example 1 was carried out, except that the compound represented by formula (107) above was used instead of the compound represented by formula (33) above and a propargyl alcohol represented by formula (108) below was used instead of the propargyl alcohol represented by formula (35) above, and the same reaction as in the sixth step of Example 1 was carried out, except that iodopropane was used instead of iodomethane, to obtain a compound represented by formula (109) below with a yield of 54%. Chemical Formula 137 Petition 870250084631, dated 09 / 19 / 2025, pp. 142 / 223 138 / 180 Chemical Formula 138 Third Stage

[00453] Referring to the method described in Patent Document 10, the compound represented by formula (109) above was reacted with 2,6-dimethylbenzenethiol to obtain a compound represented by formula (110) below with a yield of 88%. Chemical Formula 139

[00454] The photochromic compound represented by formula (110) above showed elemental analysis values ​​of C: 74.25%, H: 5.88%, N: 1.51% and S: 3.46%, which were considerably consistent with the calculated values ​​of C57H54F3NO5S of C: 74.24%, H: 5.90%, N: 1.52% and S: 3.48%. In a proton nuclear magnetic resonance spectroscopy, the photochromic compound represented by formula (110) showed 23H peaks attributed to a me group. Petition 870250084631, dated 09 / 19 / 2025, pp. 143 / 223 139 / 180 ethyl and a propyl group around δ0.5 to 3.0 ppm, a 9H peak attributed to a methoxy group around δ3.0 to 5.0 ppm, and 22H peaks attributed to aromatic protons and alkene protons around δ5.0 to 9.0 ppm. Furthermore, in a 13C nuclear magnetic resonance spectroscopy, the photochromic compound represented by formula (110) showed a peak attributed to the carbon of an aromatic ring around δ110 to 160 ppm, a peak attributed to the carbon of an alkene around δ80 to 140 ppm, and a peak attributed to the carbon of an alkyl group at δ20 to 60 ppm. Example 58 First Step

[00455] The same reaction as in the first step of Example 57 was carried out, except that 4-phenylbenzoyl chloride was used instead of 4-trifluoromethoxybenzoyl chloride, to synthesize a naphthol derivative represented by formula (111) below. Chemical Formula 140 Second Stage

[00456] The same reaction as in the fourth step of Example 1 was carried out, except that a propargyl alcohol represented by formula (112) below was synthesized using (4-bromophenyl)[4-[2-(2-methoxyethoxy)ethoxy]phenyl] methanone instead of 4-bromo-4'-methoxybenzophenone was used instead of the propargyl alcohol represented by formula (108) above and 1-bromo-4-methoxybutane was used instead of iodopropane, to obtain a compound represented by formula (113) below with a yield of 59%. Petition 870250084631, dated 09 / 19 / 2025, pp. 144 / 223 140 / 180 Chemical Formula 141 (112) Chemical Formula 142 (113) Third Stage

[00457] The same reaction as in the first step of Example 2 was carried out, except that the compound represented by formula (113) above was used instead of the compound represented by formula (38) above and thiomorpholine-1,1-dioxide was used instead of diphenylamine, to obtain a photochromic compound represented by formula (114) below with a yield of 72%. Chemical Formula 143 (114) Petition 870250084631, dated 09 / 19 / 2025, pages 145 / 223 141 / 180

[00458] The photochromic compound represented by formula (114) above had elemental analysis values ​​of C: 73.85%, H: 6.84%, N: 2.66% and S: 3.01%, which were considerably consistent with the calculated values ​​of C65H72N2O9S of C: 73.84%, H: 6.86%, N: 2.65% and S: 3.03%. In a proton nuclear magnetic resonance spectroscopy, the photochromic compound represented by formula (114) showed 19H peaks attributed to a methyl group, a 4-methoxybutyl group and a thiomorpholine-1,1-dioxide group around δ0.5 to 3.0 ppm, 28H peaks attributed to a methoxy group, a 4-methoxybutyl group, a thiomorpholine-1,1-dioxide group and a 2-(2-methoxyethoxy)ethoxy group around δ3.0 to 5.0 ppm and 25H peaks attributed to aromatic protons and alkene protons around δ5.0 to 9.0 ppm.Furthermore, in a 13C nuclear magnetic resonance spectroscopy, the photochromic compound represented by formula (114) showed a peak attributed to the carbon of an aromatic ring around δ110 at 160 ppm, a peak attributed to the carbon of an alkene around δ80 at 140 ppm and a peak attributed to the carbon of an alkyl at δ20 at 60 ppm. Example 59 First Stage

[00459] The same reaction as the second step of Example 57 was carried out, except that propargyl alcohol represented by formula (98) above was used instead of propargyl alcohol represented by formula (108) above and 1,1,1-trifluoro-3-iodopropane was used instead of iodopropane, to obtain a compound represented by formula (115) below with a yield of 63%. Petition 870250084631, dated 09 / 19 / 2025, pp. 146 / 223 142 / 180 Chemical Formula 144 Yes Br (115) OMe Second Stage

[00460] The same reaction as in the third step of Example 1 was carried out, except that the compound represented by formula (115) above was used instead of the compound represented by formula (32) above and 2,4-dimethoxyphenylboronic acid was used instead of 4-morpholinophenylboronic acid, to obtain a compound represented by formula (116) below with a yield of 91%. Chemical Formula 145 f F Third Stage

[00461] The same reaction from the fourth step of Example 55 was carried out, except that the compound represented by formula (116) above was used instead of the compound represented by formula (99) above, and the same reaction from the fifth step of Example 55 was carried out, except Petition 870250084631, dated 09 / 19 / 2025, pp. 147 / 223 143 / 180 that sebacoyl chloride was used instead of the compound represented by formula (101) above, to obtain a photochromic compound represented by formula (117) below with a yield of 89%. Chemical Formula 146

[00462] The photochromic compound represented by formula (117) above had elemental analysis values ​​of C: 66.88%, H: 4.69% and N: 1.25%, which were considerably consistent with the calculated values ​​of C124H110F18N2O16 of C: 66.90%, H: 4.98% and N: 1.26%. In a proton nuclear magnetic resonance spectroscopy, the photochromic compound represented by formula (117) showed 38H peaks attributed to a methyl group, a 1,1,1trifluoropropyl group and a sebacic acid group around δ0.5 to 3.0 ppm, 26H peaks attributed to a methoxy group and an ethylene glycol group around δ3.0 to 5.0 ppm and 46H peaks attributed to aromatic protons and alkene protons around δ5.0 to 9.0 ppm.Furthermore, in a 13C nuclear magnetic resonance spectroscopy, the photochromic compound represented by formula (117) showed a peak attributed to the carbon of an aromatic ring around δ110 at 160 ppm, a peak attributed to the carbon of an alkene around δ80 at 140 ppm and a peak attributed to the carbon of an alkyl at δ20 at 60 ppm. Example 60 First Stage

[00463] The same reaction as in the first step of Example 57 was realized in Petition 870250084631, dated 09 / 19 / 2025, page 148 / 223 144 / 180, except that 4-trifluoromethylbenzoyl chloride was used instead of 4-trifluoromethoxybenzoyl chloride, to synthesize a compound represented by formula (118) below with a yield of 86%. Chemical Formula 147 OMe <118) Second Stage

[00464] The same reaction as in the first step of Example 2 was carried out, except that the compound represented by formula (118) above was used instead of 3-bromo-4-methoxybenzophenone and N-methylaniline was used instead of diphenylamine, and the same reaction as in the third step of Example 2 was carried out, except that 4,4-dimethylcyclohexanone was used instead of 4,4-diethylcyclohexanone and the propargyl alcohol represented by formula (103) above was used instead of the propargyl alcohol represented by formula (44) above, represented by formula (119) below. Chemical Formula 148 to synthesize a compound Si (119)

[00465] The same reaction from the fourth step of Example 55 was carried out, except that the compound represented by formula (119) above was used instead of the compound represented by formula (99) above, Petition 870250084631, dated 09 / 19 / 2025, pp. 149 / 223 145 / 180 to synthesize a compound represented by formula (120) below with a yield of 92%. (120)

[00466] The same reaction as in the first step of Example 55 was carried out, except that the compound represented by formula (120) above was used instead of (4-chlorophenyl)[4-(2-hydroxyethoxy)phenyl] methanone and [tris(trimethylsiloxy)silylethyl] dimethylchlorosilane was used instead of t-butyldimethylchlorosilane, to obtain a photochromic compound represented by formula (121) below with a yield of 92%. Chemical Formula 150 (121)

[00467] The photochromic compound represented by formula (121) above had elemental analysis values ​​of C: 66.50%, H: 7.17% and N: 2.22%, which were considerably consistent with the calculated values ​​of C71H91F3N2O7Si5 of C: 66.52%, H: 7.16% and N: 2.19%. In a proton nuclear magnetic resonance spectroscopy, the photochromic compound represented by formula (121) showed pi Petition 870250084631, dated 09 / 19 / 2025, pages 150 / 223 146 / 180 cos 59H peaks assigned to a methyl group, a [tris(trimethylsiloxy)silylethyl]silyl group and a 4,4-dimethylcyclohexyl group around δ0.5 to 3.0 ppm, 8H peaks assigned to a methoxy group and an ethyloxysilyl group around δ3.0 to 5.0 ppm and 24H peaks assigned to aromatic protons and alkene protons around δ5.0 to 9.0 ppm. Furthermore, in a 13C nuclear magnetic resonance spectroscopy, the photochromic compound represented by formula (121) showed a peak attributed to the carbon of an aromatic ring around δ110 at 160 ppm, a peak attributed to the carbon of an alkene around δ80 at 140 ppm and a peak attributed to the carbon of an alkyl at δ20 at 60 ppm. Example 61

[00468] The same reaction as in the first step of Example 2 was carried out, except that 3-methoxybenzophenone was used instead of 3-bromo4-methoxybenzophenone, the same reaction as in the third step of Example 2 was carried out, except that 3,3,5,5-tetramethylcyclohexanone was used instead of 4,4-diethylcyclohexanone, and the same reaction as in the fifth step of Example 2 was carried out, except that propargyl alcohol represented by formula (49) above was used instead of propargyl alcohol represented by formula (44) above, to obtain a photochromic compound represented by formula (122) below with a yield of 67%. Chemical Formula 151 (122) Petition 870250084631, dated 09 / 19 / 2025, pages 151 / 223 147 / 180

[00469] The photochromic compound represented by formula (122) above presented elemental analysis values ​​of C: 86.27%, H: 7.08% and N: 2.03%, which were considerably consistent with the calculated values ​​of C50H49NO2 of C: 86.29%, H: 7.10% and N: 2.01%. In a proton nuclear magnetic resonance spectroscopy, the photochromic compound represented by formula (122) showed 24H peaks attributed to a methyl group, a propyl group and a cyclo-octyl group around δ0.5 to 3.0 ppm, a 3H peak attributed to a methoxy group around δ3.0 to 5.0 ppm and 22H peaks attributed to aromatic protons and alkene protons around δ5.0 to 9.0 ppm.Furthermore, in a 13C nuclear magnetic resonance spectroscopy, the photochromic compound represented by formula (122) showed a peak attributed to the carbon of an aromatic ring around δ110 at 160 ppm, a peak attributed to the carbon of an alkene around δ80 at 140 ppm and a peak attributed to the carbon of an alkyl at δ20 at 60 ppm. Example 62 First Stage

[00470] The same reaction as in the fourth step of Example 1 was carried out, except that (4-bromophenyl)(2,3-dihydro-5-benzofuranyl) methanone was used instead of 4-bromo-4'-methoxybenzophenone, to obtain a propargyl alcohol represented by formula (123) below with a yield of 79%. Chemical Formula 152 Second Stage

[00471] The same reaction from the first step of Example 1 was carried out, except that 4-bromo-3-methoxybenzophenone was used instead of Petition 870250084631, dated 09 / 19 / 2025, pp. 152 / 223 148 / 180 3-bromo-4-methoxybenzophenone, the same reaction as in the third step of Example 1 was carried out, except that 2,4-dimethoxyphenylboronic acid was used instead of 4-morpholinophenylboronic acid, the same reaction as in the fifth step of Example 1 was carried out, except that propargyl alcohol represented by formula (123) above was used instead of propargyl alcohol represented by formula (35) above, and the same reaction as in the sixth step of Example 1 was carried out, except that 1-bromo-4-methoxybutane was used instead of iodomethane, to obtain a photochromic compound represented by formula (124) below with a yield of 52%. Chemical Formula 153 (124)

[00472] The photochromic compound represented by formula (124) above had elemental analysis values ​​of C: 79.36%, H: 6.77% and N: 1.52%, which were considerably consistent with the calculated values ​​of C60H61NO7 of C: 79.35%, H: 6.77%, and N: 1.54%. In a proton nuclear magnetic resonance spectroscopy, the photochromic compound represented by formula (124) showed 17H peaks attributed to a methyl group, a 4-methoxybutyl group, and a dihydrobenzofuran group around δ0.5 to 3.0 ppm, 21H peaks attributed to a methoxy group, a 4-methoxybutyl group, and a dihydrobenzofuran group around δ3.0 to 5.0 ppm, and 23H peaks attributed Petition 870250084631, dated 09 / 19 / 2025, pp. 153 / 223 149 / 180 of the aromatic protons and alkene protons around δ5.0 to 9.0 ppm. Furthermore, in a 13C nuclear magnetic resonance spectroscopy, the photochromic compound represented by formula (124) showed a peak attributed to the carbon of an aromatic ring around δ110 to 160 ppm, a peak attributed to the carbon of an alkene around δ80 to 140 ppm and a peak attributed to the carbon of an alkyl at δ20 to 60 ppm. Examples 63 to 74 Evaluation of physical properties of photochromic plastic lenses prepared by the coating method.

[00473] Similarly to Example 26, the photochromic laminates of Examples 63 to 74 were prepared using the photochromic compounds obtained in Examples 51 to 62. Note that, in Examples 67 and 71, using the compound of Example 55 (compound represented by formula (101) above) and the compound of Example 59 (compound represented by formula (117) above), respectively, the amount of photochromic compound added was 0.125 mmol based on 100 g of the total amount of free-radical polymerizable monomers. The results are presented in Table 4. Table 4 Compound No. Wavelength of maximum absorption (nm) A23 (-) Color fading half-life at 23°C (sec) Residual rate (%) Example Example 51 482 0.44 20 60% 63 Formula (89) 603 0.43 20 60% Example Example 52 488 0.60 45 58% 64 Formula (93) 604 0.67 45 56% Example Example 53 500 0.73 56 58% 65 Formula (95) 605 0.91 56 60% Example Example 54 501 0.72 37 67% 66 Formula (96) 628 1.03 38 67% Petition 870250084631, dated 09 / 19 / 2025, pp. 154 / 223 150 / 180 Compound No. Wavelength of maximum absorption (nm) A23 (-) Color fading half-life at 23°C (sec) Residual rate (%) Example 67 Example 55 Formula (101) 545 1.18 41 62% Example Example 56 469 0.75 96 60% 68 Formula (105) 592 1.47 95 58% Example Example 57 493 0.82 54 65% 69 Formula (110) 615 0.85 55 65% Example Example 58 498 1.12 52 60% 70 Formula (114) 617 1.12 53 60% Example Example 59 491 0.47 14 63% 71 Formula (117) 600 0.68 13 63% Example Example 60 523 0.79 40 62% 72 Formula (121) 582 0.84 42 64% Example Example 61 487 1.18 156 59% 73 Formula (122) 564 1.87 154 57% Example Example 62 477 0.97 87 61% 74 Formula (124) 587 1.08 88 61% Evaluation of Physical Properties for Photochromic Layer Prepared by the Binder Method Example 75

[00474] A binder sheet was prepared using the following method. The binder sheet consisted of a first optical sheet, a first adhesive layer, a photochromic layer, a second adhesive layer, and a second optical sheet, which are laminated in this order. The first optical sheet and the second optical sheet were made of a polycarbonate sheet with a thickness of 400 μm. Preparation of Photochromic Layer-Forming Composition

[00475] A 2 L four-necked flask fitted with stirring blades, a cooling tube, a thermometer and a tube of Petition 870250084631, dated 09 / 19 / 2025, pages 155 / 223 A 151 / 180 nitrogen gaseous introduction was loaded with 315 parts by mass of polycarbonate diol with a number-average molecular weight of 1000, 100 parts by mass of isophorone diisocyanate, and 72 parts by mass of toluene. The mixture was reacted under a nitrogen atmosphere at 100°C for 7 hours to synthesize a urethane prepolymer with an isocyanate group at its terminal end. After completion of the urethane prepolymer reaction, the reaction liquid was cooled to approximately 0°C and then dissolved in 205 parts by mass of t-butyl alcohol and 382 parts by mass of diethyl ketone, maintaining the liquid temperature at 0°C. Subsequently, a mixture of 21.3 parts by mass of bis-(4-aminocyclohexyl)methane as a chain extender and 20 parts by mass of diethyl ketone was added to this reaction liquid by dropwise addition over 30 minutes, and the mixture was reacted at 0°C for 1 hour.Next, 8.1 parts by mass of 1,2,2,6,6-pentamethyl-4-aminopiperidine were added to the mixture, and the mixture was reacted at 0°C for 1 hour, obtaining a diethyl ketone solution of a non-reactive terminal urethaneurea resin.

[00476] To 100 parts by mass of the terminal non-reactive urethaneurea resin solution obtained, the photochromic compound in Example 1 (represented by formula (28) above), 6.3 parts by mass of the mixture of 4,4'-methylenebis(cyclohexyl isocyanate) isomers (polyisocyanate compound), in addition, 0.4 parts by mass of ethylene bis(oxyethylene)bis[3-(5-tert-butyl-4-hydroxy-m-tolyl)propionate] as an antioxidant and 0.06 parts by mass of DOW CORNING TORAY L7001 as a surfactant were added, and the mixture was stirred and mixed at room temperature to obtain a photochromic layer-forming composition.

[00477] Note that the amount of photochromic compound added was 0.25 mmol based on 100 parts by mass of the residue. Petition 870250084631, dated 09 / 19 / 2025, pages 156 / 223 152 / 180 in terminal non-reactive urea urethane. Preparation of the Adhesive Layer Composition

[00478] A 5 L separable flask (four necks) equipped with stirring blades, a cooling tube, a thermometer, and a nitrogen gas introduction tube was charged with 400 parts by mass of polycarbonate diol with a number-average molecular weight of 1000, 175 parts by mass of isophorone diisocyanate, and 120 parts by mass of toluene. The mixture was reacted under a nitrogen atmosphere at 110°C for 7 hours to synthesize a urethane prepolymer with an isocyanate group at its terminal end. After completion of the urethane prepolymer reaction, the reaction liquid was cooled to approximately 20°C and then dissolved in 2500 parts by mass of propylene glycol monomethyl ether, maintaining the liquid temperature at 20°C. Subsequently, 60 parts by mass of isophorone diamine as a chain extender were added to this reaction liquid, and the mixture was reacted at 20°C for 1 hour.Next, 3 parts by mass of n-butylamine were added to this mixture, and the mixture was reacted at 20°C for 1 hour, obtaining a solution of propylene glycol-monomethyl ether of a non-reactive terminal urethaneurea resin.

[00479] To 500 parts by mass of the terminal non-reactive urethaneurea resin solution obtained, 0.2 parts by mass of DOW CORNING TORAY L-7001 were added as a surfactant, and the mixture was stirred and mixed at room temperature to obtain an adhesive layer composition. Binder Sheet Production

[00480] Using a coating agent (manufactured by TESTER SANGYO CO., LTD.), the adhesive layer composition was applied to a leading face of the first optical sheet at a coating speed of 0.5 m / min and dried at a drying temperature of 110°C for 3 Petition 870250084631, dated 09 / 19 / 2025, pp. 157 / 223 153 / 180 minutes to obtain a first optical sheet with a first coating film of 5 μm thickness. Similarly to above, the adhesive layer composition was applied to a leading face of the second optical sheet to obtain a second optical sheet with a second coating film.

[00481] Next, using a coating agent (manufactured by TESTER SANGYO CO., LTD.), a layer-forming photochromic composition was applied to a 50 μm thick OPP (stretched polypropylene) film at a coating speed of 0.3 m / min and dried at a drying temperature of 100°C for 5 minutes. Thus, a third coating film was obtained. Then, the third coating film and the first optical sheet were bonded together so that the third coating film was in contact with the first coating film. From this structure, the OPP film was removed and the second optical sheet and the third coating film were bonded together so that the other exposed main face of the third coating film was in contact with the second coating film.Subsequently, the resulting laminate was left to stand under vacuum at 40°C for 24 hours, then heated to 110°C for 60 minutes, humidified at 60°C and 100% RH for 24 hours, and finally left to stand under vacuum at 40°C for 24 hours to obtain a binder sheet. The binder sheet obtained was evaluated in the same way as in Example 26. The results are presented in Table 4. Examples 76 to 83 and Comparative Examples 9 to 13

[00482] The binder sheets were prepared in the same manner as in Example 50, using the photochromic compounds presented in Table 5. Petition 870250084631, dated 09 / 19 / 2025, pp. 158 / 223 154 / 180 Table 5 Compound No. Wavelength of maximum absorption (nm) A23 (-) Color fading half-life at 23°C (sec) Residual rate (%) Example 75 Example 1 502 0.97 90 89% Formula (37) 603 1.06 91 90% Example 76 Example 25 505 0.88 76 87% Formula (88) 606 0.97 77 87% Example Formula (A) 503 0.89 68 63% Comparative 9 599 0.88 69 63% Ex. Comparative Formula(B) 503 1.31 220 79% 10 588 1.28 222 79% Ex. Comparative 11 Formula(C) 475 1.6 447 56% Ex. Comparative Formula(F) 490 1.12 105 77% 12 585 1.04 106 76% Ex.Comparative Formula(G) 500 1.05 86 71% 13 594 1.08 87 71% Example 77 Example 10 516 1.35 129 91% Formula (62) 594 1.12 128 91% Example 78 Example 11 479 0.51 43 90% Formula (65) 612 0.97 43 89% Example 79 Example 19 492 0.88 100 91% Formula (80) 604 1.14 99 91% Example 80 Example 23 506 1.02 52 89% Formula (85) 609 1.06 52 89% Example 81 Example 53 502 0.75 60 87% Formula (95) 607 0.96 60 89% Example 82 Example 57 493 0.85 61 91% Formula (110) 618 0.87 61 90% Example 83 Example 60 524 0.84 42 88% Formula (121) 582 0.87 43 89%. Petition 870250084631, dated 09 / 19 / 2025, pp. 159 / 223 155 / 180 Evaluation of physical properties for photochromic cured product prepared by the kneading method. Example 84 Preparation of the Curable Composition

[00483] First, the photochromic compound obtained in Example 1, additives, and a polymerizable compound were mixed to obtain a curable composition.

[00484] As a polymerizable compound, a combination of the following polymerizable monomers was used.

[00485] 1,3-bis(isocyanatomethyl)cyclohexane: 36.7 parts by mass

[00486] Pentaerythritol tetrakis(3-mercaptopropionate): 39.4 parts by mass

[00487] Polyoxyethylene lauryl ether of polyoxypropylene (Wonder Surf 140 manufactured by Aoki Oil Industrial Co., Ltd.): 17.4 parts by mass

[00488] 1-decanethiol: 2.8 parts by mass

[00489] RX-1 adjusted according to the method described in Patent Document 13: 3.8 parts by mass

[00490] Note that the photochromic compound was added to the curable composition such that the amount of photochromic compound was 0.106 mmol based on 100 g of the total amount of polymerizable monomer. The following additives were used:

[00491] Dimethyltin dichloride

[00492] : 0.05 parts by mass

[00493] Irganox 245: 0.1 part by mass

[00494] 2-ethylhexyl 4-methoxycinnamate: 0.6 parts by mass Production of Cured Product

[00495] The prepared curable composition was completely defoamed, injected into a glass mold with a 1 mm opening, and polymerized by casting polymerization. The polymerization was carried out... Petition 870250084631, dated 19 / 09 / 2025, page 160 / 223 156 / 180 was placed in an air furnace, gradually increasing the temperature from 27°C to 120°C over 18 hours. After polymerization, the cured product was removed from the glass mold to obtain a photochromic product with a thickness of 1 mm. The cured photochromic product obtained was evaluated in the same way as in Example 26. The results are presented in Table 6. Examples 85 to 99 and Comparative Example 14 to 18

[00496] Photochromic cured products were prepared using photochromic compounds presented in Tables 6 and 7 in the same manner as in Example 84. The results of Examples 84 and 85 and Comparative Examples 14 to 18 are summarized in Table 6, and the results of Examples 86 to 99 are summarized in Table 7. Table 6 Compound No. Wavelength of maximum absorption (nm) A23 (-) Color fading half-life at 23°C (sec) Residual rate (%) Example 84 Example 1 503 0.96 112 72% Formula (37) 610 1.06 112 72% Example 85 Example 25 505 0.88 96 68% Formula (88) 613 0.96 95 68% Comparative Ex. Formula(A) 503 0.92 81 50% 14 607 0.89 81 50% Comparative Ex. Formula(B) 506 1.33 268 61% 15 593 1.27 267 61% Comparative Ex. 16 Formula(C) 475 1.68 561 39% Ex. Comparative Formula(F) 493 1.14 129 58% 17 591 1.05 129 59% Ex. Comparative Formula(G) 502 1.05 107 54% 18 602 1.07 108 54% Petition 870250084631, dated 09 / 19 / 2025, pp. 161 / 223 157 / 180 Table 7 Compound No. Wavelength of maximum absorption (nm) A23 (-) Color fading half-life at 23°C (sec) Residual rate (%) Example 86 Example 2 Formula (45) 526 1.41 105 72% Example 87 Example 3 472 0.59 99 61% Formula (46) 619 1.16 99 61% Example 88 Example 5 511 0.56 68 75% Formula (51) 598 0.69 67 75% Example 89 Example 7 499 0.75 99 68% Formula (55) 610 0.99 100 68% Example 90 Example 8 476 0.51 105 68% Formula (57) 604 1.24 105 68% Example 91 Example 10 519 1.41 165 68% Formula (62) 600 1.09 163 70% Example 92 Example 14 496 0.59 72 71% Formula (71) 590 0.65 72 70% Example 93 Example 16 475 0.47 68 64% Formula (77) 593 0.86 68 64% Example 94 Example 19 496 0.87 130 73% Formula (80) 610 1.15 131 73% Example 95 Example 21 490 0.62 102 68% Formula (83) 616 1.25 103 68% Example 96 Example 24 505 1.32 124 65% Formula (86) 607 1.31 125 65% Example 97 Example 51 486 0.46 30 68% Formula (89) 612 0.45 30 68% Example 98 Example 57 496 0.86 74 72% Formula (110) 625 0.88 74 72% Example 99 Example 62 479 1.02 125 67% Formula (124) 594 1.11 126 67%, Petition 870250084631, dated 09 / 19 / 2025, pp. 162 / 223 158 / 180

[00497] Preferred aspects of the present invention will be described below.

[00498] A photochromic compound with a skeleton represented by formula (1) below: R3 is an aryl group or heteroaryl group substituted by a group represented by formula (1a) below, Chemical Formula 155 R2 in formula (1a) above, R1 is a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted fused polycyclic ring in which an aromatic ring or an aromatic heterocyclic ring is fused with these substituents. R2 is a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted haloalkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkoxy group, or a substituted or unsubstituted aryloxy group. Petition 870250084631, dated 09 / 19 / 2025, pp. 163 / 223 159 / 180 do, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted aralkyl group or a group represented by formula (2a) below, -Q1-(X1Q2)a-X2Q3 (2a) in formula (2a) above, Q1 is an alkylene group or a haloalkylene group. Q2 is an alkylene group or a haloalkylene group, Q3 is an alkyl group or a haloalkyl group. X1 and X2 are each independently O, S, NR700, PR701 or P(=O), R700 and R701 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, where a is an integer from 0, or 1 or more and 3 or less. R4 is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group, and ring A and ring B are each independently a substituted or unsubstituted aromatic ring, a substituted or unsubstituted aromatic heterocyclic ring, or a substituted or unsubstituted fused polycyclic ring in which an aromatic ring or an aromatic heterocyclic ring is fused with these rings. [2]

[00499] The photochromic compound as described in [1], where the photochromic compound has a skeleton represented by formula (2) below: Petition 870250084631, dated 09 / 19 / 2025, pp. 164 / 223 160 / 180 Chemical Formula 156 (2) wherein, in formula (2) above, M, R3 and R4 are each the same as those in formula (1) above. [31

[00500] The photochromic compound as described in [1] or [2], wherein the photochromic compound has a skeleton represented by formula (3) below: Chemical Formula 157 (3) wherein, in formula (3) above, M, R3 and R4 are each the same as those in formula (1) above, R5 and R6 are each independently a hydrogen atom, a hydroxyl group, a substituted or unsubstituted alkyl group, a haloalkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted heterocyclic group, a cyano group, a halogen atom, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a nitro group, a formyl group, a hi group Petition 870250084631, dated 09 / 19 / 2025, pp. 165 / 223 161 / 180 hydroxycarbonyl, a substituted or unsubstituted alkylcarbonyl group, a substituted or unsubstituted alkoxycarbonyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aralkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a thiol group, a substituted or unsubstituted alkoxyalkylthio group, a haloalkylthio group, a substituted or unsubstituted cycloalkylthio group, a substituted or unsubstituted silyl group, a substituted or unsubstituted oxysilyl group, a group represented by formula (2a) above, a group represented by formula (X) below, or a group represented by formula (X3) below, Chemical Formula 158 in formula (X), E is an oxygen atom or NR101, and R101 is a hydrogen atom or an alkyl group. F is either an oxygen atom or a sulfur atom. G is an oxygen atom, a sulfur atom, or NR2O2, R2O2 is a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a heteroaryl group, g is 0 or 1, R201 is a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a heteroaryl group; when G is an oxygen atom or a sulfur atom, R201 is a group other than a hydrogen atom. L1-R400(X3) in formula (X3) above, Petition 870250084631, dated 09 / 19 / 2025, pp. 166 / 223 162 / 180 R400 is a hydrogen atom, an alkyl group, an aryl group, a polymerizable group, a photochromic group, or a silyl group having, as a substituent, an alkyl group, an alkoxy group, or an aryl group. L1 is a group represented by formula (X2) below, Chemical Formula 159 in formula (X2) above, R30 is a group represented by formula (X2a) below, Chemical formula 160 in formulas (X2) and (X2a) above, J represents a divalent group, each independently directly bonded, a substituted or unsubstituted methylene group, an oxygen atom, a sulfur atom, or NR3O1, and R3O1 is a hydrogen atom or an alkyl group. L is either an oxygen atom or a sulfur atom. R300 is an alkylene group or a silylene group having an alkyl or aryl group as a substituent; r302, r303, and r304 are each independently an alkylene group; h, j, and kel are each independently an integer from 0 or 1; i is an integer from 1 to 200; and when i is 2 or more, a plurality of R30 groups may be the same or different from one another. Petition 870250084631, dated 09 / 19 / 2025, pp. 167 / 223 163 / 180 others, the dashed lines indicate connections with R400, and R5 and R6, together with M, can constitute a substituted or unsubstituted aliphatic ring having from 3 to 20 carbon atoms in the ring, a substituted or unsubstituted fused polycyclic ring in which an aromatic hydrocarbon ring or an aromatic heterocyclic ring is fused with the aliphatic ring, a substituted or unsubstituted heterocyclic ring having from 3 to 20 atoms in the ring, or a substituted or unsubstituted fused polycyclic ring in which an aromatic ring or an aromatic heterocyclic ring is fused with the heterocyclic ring. [4]

[00501] The photochromic compound as described in [3], wherein R5 and R6 are each independently a hydrogen atom, a hydroxy group, a substituted or unsubstituted alkyl group, a haloalkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted heterocyclic group, a cyano group, a halogen atom, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a nitro group, a formyl group, a hydroxycarbonyl group, a substituted or unsubstituted alkylcarbonyl group, a substituted or unsubstituted alkoxycarbonyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aralkoxyl group, a substituted or unsubstituted aryloxyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a thiol group,a substituted or unsubstituted alkoxyalkylthio group, a haloalkylthio group, a substituted or unsubstituted cycloalkylthio group, a substituted or unsubstituted silyl group, a substituted or unsubstituted oxysilyl group, a group represented by formula (X) above, or a group represented by, Petition 870250084631, dated 09 / 19 / 2025, pp. 168 / 223 164 / 180 formula (X3) above. [5]

[00502] The photochromic compound as described in [3], where the photochromic compound is represented by formula (4) below: Chemical Formula 161 where, in formula (4) above, R3, R4, R5, R6 and M are each the same as those in formula (3) above, R7 and R8 are each independently a hydroxy group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted haloalkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted haloalkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted heterocyclic group, a cyano group, a halogen atom, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a nitro group, a formyl group, a hydroxycarbonyl group, a substituted or unsubstituted alkylcarbonyl group, a substituted or unsubstituted alkoxycarbonyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aralkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryl group,a substituted or unsubstituted heteroaryl group, a thiol group, a substituted or unsubstituted alkoxyalkylthio group, a Petition 870250084631, dated 09 / 19 / 2025, pp. 169 / 223 165 / 180 haloalkylthio group, a substituted or unsubstituted cycloalkylthio group, a substituted or unsubstituted silyl group, a substituted or unsubstituted oxysilyl group, a group represented by formula (2a) above, a group represented by formula (X) above, or a group represented by formula (X3) above, b is an integer from 0 to 4 and c is an integer from 0 to 4, when b is from 2 to 4, a plurality of R7 groups may be the same or different from each other, when c is from 2 to 4, a plurality of R8 groups may be the same or different from each other, when b is from 2 to 4 and there are R7 groups adjacent to each other, the two adjacent R7 groups, together with carbon atoms to which the R7 groups are attached, may constitute a substituted or unsubstituted aliphatic ring, a substituted or unsubstituted aliphatic heterocyclic ring, a substituted or unsubstituted aromatic ring,A substituted or unsubstituted aromatic heterocyclic ring or a substituted or unsubstituted fused polycyclic ring in which an aromatic ring or an aromatic heterocyclic ring is fused with these rings, and when c is from 2 to 4 and there are R8 groups adjacent to each other, the two adjacent R8 groups, together with carbon atoms to which the R8 groups are attached, may collectively constitute a substituted or unsubstituted aliphatic ring, a substituted or unsubstituted aliphatic heterocyclic ring, a substituted or unsubstituted aromatic ring, a substituted or unsubstituted aromatic heterocyclic ring, or a substituted or unsubstituted fused polycyclic ring in which an aromatic ring or an aromatic heterocyclic ring is fused with these rings. Petition 870250084631, dated 09 / 19 / 2025, pp. 170 / 223 166 / 180 [6]

[00503] The photochromic compound as described in [5], wherein the photochromic compound is represented by formula (5) below: Chemical Formula 162 wherein, in formula (5) above, R3, R4, R5, R6, R7, R8, b and c are each the same as those in formula (4) above. [7]

[00504] The photochromic compound as described in [6], wherein the photochromic compound is represented by formula (6) below: Chemical Formula 163 wherein, in formula (6) above, R5, R6, R7, R8, b and c are each the same as those in formula (5) above, R9a is a group represented by formula (1a) above, a hydrogen atom, a hydroxyl group, an alkyl group with 1 to 6 carbon atoms, a haloalkyl group with 1 to 6 carbon atoms, a cycloalkyl group with 3 to 8 carbon atoms, a group Petition 870250084631, dated 09 / 19 / 2025, pp. 171 / 223 167 / 180 alkoxy with 1 to 6 carbon atoms, a substituted or unsubstituted amino group, a substituted or unsubstituted heterocyclic group, a cyano group, a halogen atom, an alkylthio group with 1 to 6 carbon atoms, a substituted or unsubstituted arylthio group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted oxysilyl group, a group represented by formula (2a) above, or a group represented by formula (X3) above, d1 is an integer from 1 to 5, when d1 is 1, R9a is a group represented by formula (1a) above, when d1 is 2 to 5, at least one of a plurality of groups R9a is a group represented by formula (1a) above, the plurality of groups R9a may be equal or different from each other, when there are groups R9aadjacent to each other,Except for the group represented by formula (1a) above, the two adjacent R9a groups, together with carbon atoms to which the R9ase groups attach, may constitute a substituted or unsubstituted aliphatic ring, a substituted or unsubstituted aliphatic heterocyclic ring, a substituted or unsubstituted aromatic ring, a substituted or unsubstituted aromatic heterocyclic ring, or a substituted or unsubstituted fused polycyclic ring in which an aromatic ring or an aromatic heterocyclic ring is fused with these rings. R10a is a hydroxyl group, an alkyl group with 1 to 6 carbon atoms, a haloalkyl group with 1 to 6 carbon atoms, a cycloalkyl group with 3 to 8 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, a substituted or unsubstituted amino group, a substituted or unsubstituted heterocyclic group, a cyano group, a halogen atom, an alkylthio group with 1 to 6 carbon atoms. Petition 870250084631, dated 09 / 19 / 2025, pp. 172 / 223 168 / 180 carbon, a substituted or unsubstituted arylthio group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted oxysilyl group, a group represented by formula (2a) above, or a group represented by formula (X3) above, e1 is an integer from 0 to 5, when e1 is from 2 to 5, the plurality of R10a may be the same or different from each other, and when there are adjacent R10a groups, the two adjacent R10a groups, together with carbon atoms to which the R10a groups attach, may constitute a substituted or unsubstituted aliphatic ring, a substituted or unsubstituted aliphatic heterocyclic ring, a substituted or unsubstituted aromatic ring, a substituted or unsubstituted aromatic heterocyclic ring,or a substituted or unsubstituted fused polycyclic ring in which an aromatic ring or an aromatic heterocyclic ring is fused with these rings. 181

[00505] The photochromic compound as described in [7], wherein the photochromic compound is represented by formula (7) below: Chemical Formula 164 Petition 870250084631, dated 09 / 19 / 2025, pp. 173 / 223 169 / 180 where, in formula (7) above, R5, R6, R7, R8, R10a, b, c and e1 are each the same as those in formula (6) above, R9 is a group represented by formula (1a) above, R9bé is a hydroxyl group, an alkyl group with 1 to 6 carbon atoms, a haloalkyl group with 1 to 6 carbon atoms, a cycloalkyl group with 3 to 8 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, a substituted or unsubstituted amino group, a substituted or unsubstituted heterocyclic group, a cyano group, a halogen atom, an alkylthio group with 1 to 6 carbon atoms, a substituted or unsubstituted arylthio group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted oxysilyl group, a group represented by formula (2a) above, or a group represented by formula (X3) above, d2 is an integer from 0 to 4, when d2 is from 2 to 4, a plurality of R9b groups may be equal or different from each other, and when there are R9 groups adjacent to each other,the two adjacent R9b groups, together with carbon atoms to which the R9b groups are attached, can constitute a substituted or unsubstituted aliphatic ring, a substituted or unsubstituted aliphatic heterocyclic ring, a substituted or unsubstituted aromatic ring, a substituted or unsubstituted aromatic heterocyclic ring, or a substituted or unsubstituted fused polycyclic ring in which an aromatic ring or an aromatic heterocyclic ring is fused with these rings. [9]

[00506] The photochromic compound as described in [8], wherein the photochromic compound is represented by formula (8) below: Petition 870250084631, dated 09 / 19 / 2025, pp. 174 / 223 170 / 180 Chemical Formula 165 where, in formula (8) above, R5, R6, R7, R8, R9, R9b, b, c and d2 are each the same as those in formula (7) above, R10 is an alkyl group with 1 to 6 carbon atoms, a haloalkyl group with 1 to 6 carbon atoms, a cycloalkyl group with 3 to 8 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, a substituted or unsubstituted amino group, a substituted or unsubstituted heterocyclic group, a halogen atom, an alkylthio group with 1 to 6 carbon atoms, a substituted or unsubstituted arylthio group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted oxysilyl group, a group represented by formula (2a) above, or a group represented by formula (X3) above, R10bé is a hydroxyl group, an alkyl group with 1 to 6 carbon atoms, a haloalkyl group with 1 to 6 carbon atoms, a cycloalkyl group with 3 to 8 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, a substituted or unsubstituted amino group, a substituted or unsubstituted heterocyclic group, a cyano group, a halogen atom, an alkylthio group with 1 to 6 carbon atoms, a substituted or unsubstituted arylthio group, an ari group Petition 870250084631, dated 09 / 19 / 2025, pp. 175 / 223 171 / 180 substituted or unsubstituted oxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted oxysilyl group, a group represented by formula (2a) above, or a group represented by formula (X3) above, e2 is an integer from 0 to 4, when e2 is from 2 to 4, a plurality of R10b groups may be the same or different from each other, and when there are adjacent R10b groups, the two adjacent R10b groups, together with carbon atoms to which the R10b groups are attached, may constitute a substituted or unsubstituted aliphatic ring, a substituted or unsubstituted aliphatic heterocyclic ring, a substituted or unsubstituted aromatic ring, a substituted or unsubstituted aromatic heterocyclic ring,or a substituted or unsubstituted fused polycyclic ring in which an aromatic ring or an aromatic heterocyclic ring is fused with these rings.

[10]

[00507] The photochromic compound as described in any one of [1] to [9], where R1 is a substituted or unsubstituted phenyl group.

[11]

[00508] The photochromic compound as described in any one of [1] to

[10] , wherein R2 is a substituted or unsubstituted alkyl group having 1 or more and 10 or fewer carbon atoms, a substituted or unsubstituted cycloalkyl group having 5 or more and 10 or fewer carbon atoms, a substituted or unsubstituted haloalkyl group having 1 or more and 10 or fewer carbon atoms, or a group represented by formula (2a) above.

[12] Petition 870250084631, dated 09 / 19 / 2025, pp. 176 / 223 172 / 180

[00509] A curable composition including the photochromic compound as described in any one of [1] to

[11] , and at least one selected from a group consisting of a radically polymerizable monomer, a cationic polymerizable monomer, a compound having a polymerizable group and a (thio)urethane(urea) polymer.

[13]

[00510] A cured product of the curable composition as described in

[12] .

[14]

[00511] An optical article including the cured product as described in

[13] .

[15]

[00512] A lens including the photochromic compound as described in any one of [1] to

[11] .

[16]

[00513] Glasses including the lens as described in

[15] .

[17]

[00514] A propargyl alcohol compound represented by formula (9) below; Chemical Formula 166 ^4 (9) where, in formula (9) above, R3 is an aryl group or a heteroaryl group substituted by a group represented by formula (1a) below, Chemical Formula 167 (1a) Petition 870250084631, dated 09 / 19 / 2025, pp. 177 / 223 173 / 180 in formula (1a) above, R1 is a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted fused polycyclic ring in which an aromatic ring or an aromatic heterocyclic ring is fused with these substituents. R2 is a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted haloalkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted aralkyl group, or a group represented by formula (2a) below, -Q1-(X1Q2)a-X2Q3(2a) in formula (2a) above, Q1 is an alkylene group or a haloalkylene group. Q2 is an alkylene group or a haloalkylene group. Q3 is an alkyl group or a haloalkyl group. X1 and X2 are each independently O, S, NR700, PR701 or P(=O), R700 and R701 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, where a is an integer from 0, or 1 or more and 3 or less, and R4 is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. Petition 870250084631, dated 09 / 19 / 2025, pp. 178 / 223 174 / 180

[18]

[00515] The propargyl alcohol compound as described in

[17] , wherein the propargyl alcohol compound is represented by formula (10) below: Chemical Formula 168 (R1°V I '1 ,r^9a, I —(R )di (10) in formula (10) above, R9a is a group represented by formula (1a) above, a hydrogen atom, a hydroxy group, an alkyl group with 1 to 6 carbon atoms, a haloalkyl group with 1 to 6 carbon atoms, a cycloalkyl group with 3 to 8 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, a substituted or unsubstituted amino group, a substituted or unsubstituted heterocyclic group, a cyano group, a halogen atom, an alkylthio group with 1 to 6 carbon atoms, a substituted or unsubstituted arylthio group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted oxysilyl group, a group represented by formula (2a) above, or a group represented by formula (X3) above, L1-R400(X3) in formula (X3) above, R400 is a hydrogen atom, an alkyl group, an aryl group, a polymerizable group, a photochromic group, or a silyl group having, as a substituent, an alkyl group, an alkoxy group, or an aryl group. L1 is a group represented by the formula (X2) below, Petition 870250084631, dated 09 / 19 / 2025, pp. 179 / 223 175 / 180 Chemical formula 169 in formula (X2) above, R30 is a group represented by formula (X2a) below, Chemical formula 170 in formulas (X2) and (X2a) above, J represents a divalent group, each independently directly bonded, a substituted or unsubstituted methylene group, an oxygen atom, a sulfur atom, or NR3O1, and R3O1 is a hydrogen atom or an alkyl group. L is either an oxygen atom or a sulfur atom. R300 is an alkylene group or a silylene group having an alkyl group or an aryl group as a substituent, r302, r303 and r304 are each independently an alkylene group, h, j, kel are each independently an integer from 0 or 1, i is an integer from 1 to 200, when i is 2 or more, the structures of a plurality of R30 groups may be the same or different from each other, and the dashed lines indicate linkages with R400, d1 is an integer from 1 to 5, when d1 is 1, R9a is a group represented by formula (1a) above, when d1 is from 2 to 5, at least one of a plurality Petition 870250084631, dated 09 / 19 / 2025, pp. 180 / 223 176 / 180 of R9a groups is a group represented by formula (1a) above, and the plurality of R9a groups may be equal or different from each other, when there are adjacent R9a groups, except for the group represented by formula (1a) above, the two adjacent R9a groups, together with carbon atoms to which the R9a groups are attached, may constitute a substituted or unsubstituted aliphatic ring, a substituted or unsubstituted aliphatic heterocyclic ring, a substituted or unsubstituted aromatic ring, a substituted or unsubstituted aromatic heterocyclic ring, or a substituted or unsubstituted fused polycyclic ring in which an aromatic ring or an aromatic heterocyclic ring is fused with these rings, R10a is a hydroxy group, an alkyl group with 1 to 6 carbon atoms, a haloalkyl group with 1 to 6 carbon atoms, a cycloalkyl group with 3 to 8 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, a substituted or unsubstituted amino group, a substituted or unsubstituted heterocyclic group, a cyano group, a halogen atom, an alkylthio group with 1 to 6 carbon atoms, a substituted or unsubstituted arylthio group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted oxysilyl group, a group represented by formula (2a) above, or a group represented by formula (X3) above, e1 is an integer from 0 to 5, when e1 is from 2 to 5, the plurality of R10a can be equal or different from each other, and when there are R10a groups adjacent to each other,The two adjacent R10a groups, together with carbon atoms to which the R10ase groups are attached, can form a substituted aliphatic ring. Petition 870250084631, dated 09 / 19 / 2025, pp. 181 / 223 177 / 180 or unsubstituted, a substituted or unsubstituted aliphatic heterocyclic ring, a substituted or unsubstituted aromatic ring, a substituted or unsubstituted aromatic heterocyclic ring, or a substituted or unsubstituted fused polycyclic ring in which an aromatic ring or an aromatic heterocyclic ring is fused with these rings.

[19]

[00516] The propargyl alcohol compound as described in

[18] , wherein the propargyl alcohol compound is represented by formula (11) below: Chemical Formula 171 In formula (11) above, R10ae e1 are the same as those in formula (10) above, R9 is a group represented by formula (1a) above, R9bé is a hydroxyl group, an alkyl group with 1 to 6 carbon atoms, a haloalkyl group with 1 to 6 carbon atoms, a cycloalkyl group with 3 to 8 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, a substituted or unsubstituted amino group, a substituted or unsubstituted heterocyclic group, a cyano group, a halogen atom, an alkylthio group with 1 to 6 carbon atoms, a substituted or unsubstituted arylthio group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted oxysilyl group, a group represented by formula (2a) above, or a group represented by formula (X3) above, d2 is an integer from 0 to 4, and Petition 870250084631, dated 09 / 19 / 2025, pp. 182 / 223 178 / 180 when d2 is from 2 to 4, a plurality of R9b groups may be the same or different from each other, and when there are adjacent R9b groups, the two adjacent R9b groups, together with carbon atoms to which the R9b groups are attached, may constitute a substituted or unsubstituted aliphatic ring, a substituted or unsubstituted aliphatic heterocyclic ring, a substituted or unsubstituted aromatic ring, a substituted or unsubstituted aromatic heterocyclic ring, or a substituted or unsubstituted fused polycyclic ring in which an aromatic ring or an aromatic heterocyclic ring is fused with these rings.

[20]

[00517] The propargyl alcohol compound as described in

[19] , wherein the propargyl alcohol compound is represented by formula (12) below: Chemical Formula 172 In formula (12) above, R9, R9be d2 are the same as those in formula (11) above. R10 is an alkyl group with 1 to 6 carbon atoms, a haloalkyl group with 1 to 6 carbon atoms, a cycloalkyl group with 3 to 8 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, a substituted or unsubstituted amino group, a substituted or unsubstituted heterocyclic group, a halogen atom, an alkylthio group with 1 to 6 carbon atoms, a substituted or unsubstituted arylthio group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted silyl group Petition 870250084631, dated 09 / 19 / 2025, pp. 183 / 223 179 / 180 substituted, a substituted or unsubstituted oxysyl group, a group represented by formula (2a) above, or a group represented by formula (X3) above, R10bé is a hydroxyl group, an alkyl group with 1 to 6 carbon atoms, a haloalkyl group with 1 to 6 carbon atoms, a cycloalkyl group with 3 to 8 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, a substituted or unsubstituted amino group, a substituted or unsubstituted heterocyclic group, a cyano group, a halogen atom, an alkylthio group with 1 to 6 carbon atoms, a substituted or unsubstituted arylthio group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted oxysilyl group, a group represented by formula (2a) above, or a group represented by formula (X3) above, e2 is an integer from 0 to 4, when e2 is from 2 to 4, a plurality of R10b groups may be identical or different from each other, and when there are R10 groups adjacent to each other,the two adjacent R10b groups, together with carbon atoms to which the R10b groups are attached, can constitute a substituted or unsubstituted aliphatic ring, a substituted or unsubstituted aliphatic heterocyclic ring, a substituted or unsubstituted aromatic ring, a substituted or unsubstituted aromatic heterocyclic ring, or a substituted or unsubstituted fused polycyclic ring in which an aromatic ring or an aromatic heterocyclic ring is fused with these rings.

[21]

[00518] The propargyl alcohol compound as described in any one of

[17] to

[21] , where R1 is a substituted phenyl group or Petition 870250084631, dated 09 / 19 / 2025, pp. 184 / 223 180 / 180 unsubstituted, R2 is a substituted or unsubstituted alkyl group having 1 or more and 10 or fewer carbon atoms, a substituted or unsubstituted cycloalkyl group having 5 or more and 10 or fewer carbon atoms, a substituted or unsubstituted haloalkyl group having 1 or more and 10 or fewer carbon atoms, or a group represented by formula (2a) above. < / m>

Claims

1. Photochromic compound with a skeleton represented by formula (1) below: Chemical Formula 1 (1) characterized in that, in formula (1) above, M is C, Si or Ge, R3 is an aryl group or a heteroaryl group substituted by a group represented by formula (1a) below, Chemical Formula 2 N' R2 in formula (1a) above, R1 is a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted fused polycyclic ring in which an aromatic ring or an aromatic heterocyclic ring is fused with these substituents, R2 is a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted haloalkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group,a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted aralkyl group Petition 870250084631, dated 19 / 09 / 2025, p. 186 / 223 2 / 22 substituted or a group represented by formula (2a) below, -Q1-(X1 Q2)a-X2 Q3 (2a) in formula (2a) above, Q1 is an alkylene group or a haloalkylene group, Q2 is an alkylene group or a haloalkylene group, Q3 is an alkyl group or a haloalkyl group, X1 and X2 are each independently O, S, NR700, PR701 or P(=O), R700 and R701 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, a is an integer of 0, or 1 or more and 3 or less, R4 is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group,and ring A and ring B are each independently a substituted or unsubstituted aromatic ring, a substituted or unsubstituted aromatic heterocyclic ring, or a substituted or unsubstituted fused polycyclic ring in which an aromatic ring or an aromatic heterocyclic ring is fused with these rings.

2. Photochromic compound according to claim 1, characterized in that the photochromic compound has a skeleton represented by formula (2) below: Chemical Formula 3, (2) Petition 870250084631, dated 09 / 19 / 2025, p. 187 / 223 3 / 22 where, in formula (2) above, M, R3 and R4 are each the same as those in formula (1) above.

3. Photochromic compound, according to claim 1 or 2, characterized in that the photochromic compound has a skeleton represented by formula (3) below: Chemical Formula 4 wherein, in formula (3) above, M, R3 and R4 are each the same as those in formula (1) above, R5 and R6 are each independently a hydrogen atom, a hydroxy group, a substituted or unsubstituted alkyl group, a haloalkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted heterocyclic group, a cyano group, a halogen atom, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a nitro group, a formyl group, a hydroxycarbonyl group,a substituted or unsubstituted alkylcarbonyl group, a substituted or unsubstituted alkoxycarbonyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aralkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a thiol group, a substituted or unsubstituted alkoxyalkylthio group, a haloalkylthio group, a substituted or unsubstituted cycloalkylthio group, a substituted or unsubstituted silyl group. Petition 870250084631, dated 19 / 09 / 2025, p. 188 / 223 4 / 22 substituted, a substituted or unsubstituted oxysyl group, a group represented by formula (2a) above, a group represented by formula (X) below, or a group represented by formula (X3) below, Chemical Formula 5 in formula (X), E is an oxygen atom or NR101, and R101 is a hydrogen atom or an alkyl group, F is an oxygen atom or a sulfur atom,G is an oxygen atom, a sulfur atom or NR202, R202 is a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a heteroaryl group, g is 0 or 1, R201 is a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a heteroaryl group, when G is an oxygen atom or a sulfur atom, R201 is a group other than a hydrogen atom, L1-R400 (X3) in formula (X3) above, R400 is a hydrogen atom, an alkyl group, an aryl group, a polymerizable group, a photochromic group or a silyl group having, as a substituent, an alkyl group, an alkoxy group or an aryl group, L1 is a group represented by formula (X2) below, Petition 870250084631, dated 19 / 09 / 2025, page. 189 / 223 5 / 22 Chemical Formula 6 in formula (X2) above, R30 is a group represented by formula (X2a) below, Chemical Formula 7 in formulas (X2) and (X2a) above, J represents a divalent group, each independently directly bonded,a substituted or unsubstituted methylene group, an oxygen atom, a sulfur atom, or NR301, and R301 is a hydrogen atom or an alkyl group, L is an oxygen atom or a sulfur atom, R300 is an alkylene group or a silylene group having an alkyl or aryl group as a substituent, R302, r303 and r304 are each independently an alkylene group, h, j, kel are each independently an integer from 0 or 1, i is an integer from 1 to 200, and when i is 2 or more, the plurality of R30 groups may be equal or different from each other, and the dashed lines indicate linkages with R400, and R5 and R6, together with M, may constitute a substituted or unsubstituted aliphatic ring having from 3 to 20 carbon atoms in the ring, a substituted or unsubstituted fused polycyclic ring in which a hydrocarbon ring aromatic or a heterocyclic ring Petition 870250084631, dated 19 / 09 / 2025, p. 190 / 223 6 / 22 aromatic is fused with the aliphatic ring,A substituted or unsubstituted heterocyclic ring having from 3 to 20 ring atoms, or a substituted or unsubstituted fused polycyclic ring in which an aromatic ring or an aromatic heterocyclic ring is fused with the heterocyclic ring.

4. Photochromic compound, according to claim 3, characterized in that R5 and R6 are each independently a hydrogen atom, a hydroxy group, a substituted or unsubstituted alkyl group, a haloalkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted heterocyclic group, a cyano group, a halogen atom, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a nitro group, a formyl group, a hydroxycarbonyl group, a substituted or unsubstituted alkylcarbonyl group,a substituted or unsubstituted alkoxycarbonyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aralkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a thiol group, a substituted or unsubstituted alkoxyalkylthio group, a haloalkylthio group, a substituted or unsubstituted cycloalkylthio group, a substituted or unsubstituted silyl group, a substituted or unsubstituted oxysilyl group, a group represented by formula (X) above, or a group represented by formula (X3) above.

5. Photochromic compound, according to claim 3, characterized in that the photochromic compound is represented by formula (4) below: Petition 870250084631, dated 19 / 09 / 2025, p. 191 / 223 7 / 22 Chemical Formula 8 where, in formula (4) above, R3, R4, R5, R6 and M are each the same as those in formula (3) above,R7 and R8 are each independently a hydroxy group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted haloalkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted haloalkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted heterocyclic group, a cyano group, a halogen atom, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a nitro group, a formyl group, a hydroxycarbonyl group, a substituted or unsubstituted alkylcarbonyl group, a substituted or unsubstituted alkoxycarbonyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aralkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryl group,a substituted or unsubstituted heteroaryl group, a thiol group, a substituted or unsubstituted alkoxyalkylthio group, a haloalkylthio group, a substituted or unsubstituted cycloalkylthio group, a substituted or unsubstituted silyl group, a substituted or unsubstituted oxysilyl group, a group represented by formula (2a) above, a group represented by formula (X) above, or a Petition 870250084631, dated 19 / 09 / 2025, page. 192 / 223 8 / 22 group represented by formula (X3) above, b is an integer from 0 to 4, c is an integer from 0 to 4, when b is from 2 to 4, a plurality of R7 groups may be the same or different from each other, when c is from 2 to 4, a plurality of R8 groups may be the same or different from each other, when b is 2 to 4 and there are R7 groups adjacent to each other, the two adjacent R7 groups, together with carbon atoms to which the R7 groups are attached, may constitute a substituted or unsubstituted aliphatic ring,a substituted or unsubstituted aliphatic heterocyclic ring, a substituted or unsubstituted aromatic ring, a substituted or unsubstituted aromatic heterocyclic ring, or a substituted or unsubstituted fused polycyclic ring in which an aromatic ring or an aromatic heterocyclic ring is fused with these rings, and when c is from 2 to 4 and there are R8 groups adjacent to each other, the two adjacent R8 groups, together with carbon atoms to which the R8 groups are attached, may collectively constitute a substituted or unsubstituted aliphatic ring, a substituted or unsubstituted aliphatic heterocyclic ring, a substituted or unsubstituted aromatic ring, a substituted or unsubstituted aromatic heterocyclic ring, or a substituted or unsubstituted fused polycyclic ring in which an aromatic ring or an aromatic heterocyclic ring is fused with these rings.

6. Photochromic compound, according to claim 5,characterized by the fact that the photochromic compound is represented by formula (5) below: Petition 870250084631, dated 09 / 19 / 2025, page 193 / 223 9 / 22 one the same as those in formula (4) above.

7. Photochromic compound, according to claim 6, characterized in that the photochromic compound is represented by formula (6) below: Chemical Formula 10 in formula (6) above, R5, R6, R7, R8, b and c are each the same as those in formula (5) above, R9a is a group represented by formula (1a) above, a hydrogen atom, a hydroxyl group, an alkyl group with 1 to 6 carbon atoms, a haloalkyl group with 1 to 6 carbon atoms, a cycloalkyl group with 3 to 8 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, a substituted or unsubstituted amino group, a substituted or unsubstituted heterocyclic group, a cyano group, a halogen atom, an alkylthio group with 1 to 6 carbon atoms. Petition 870250084631, dated 19 / 09 / 2025, page. 194 / 223 10 / 22 carbon atoms,a substituted or unsubstituted arylthio group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted oxysilyl group, a group represented by formula (2a) above, or a group represented by formula (X3) above, d1 is an integer from 1 to 5, when d1 is 1, R9a is a group represented by formula (1a) above, when d1 is from 2 to 5, at least one of a plurality of R9a groups is a group represented by formula (1a) above, and the plurality of R9a groups may be equal or different from each other, when there are adjacent R9a groups, except for the group represented by formula (1a) above, the two adjacent R9a groups, together with carbon atoms to which the R9a groups are attached, may constitute a substituted or unsubstituted aliphatic ring,a substituted or unsubstituted aliphatic heterocyclic ring, a substituted or unsubstituted aromatic ring, a substituted or unsubstituted aromatic heterocyclic ring, or a substituted or unsubstituted fused polycyclic ring in which an aromatic ring or an aromatic heterocyclic ring is fused with these rings, R10a is a hydroxy group, an alkyl group with 1 to 6 carbon atoms, a haloalkyl group with 1 to 6 carbon atoms, a cycloalkyl group with 3 to 8 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, a substituted or unsubstituted amino group, a substituted or unsubstituted heterocyclic group, a cyano group, a halogen atom, an alkylthio group with 1 to 6 carbon atoms, a substituted or unsubstituted arylthio group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryl group Petition 870250084631, of 19 / 09 / 2025, page 195 / 223 11 / 22 replaced, a replaced or unreplaced heteroaryl group,a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted oxysilyl group, a group represented by formula (2a) above, or a group represented by formula (X3) above, e1 is an integer from 0 to 5, when e1 is from 2 to 5, the plurality of R10a may be the same or different from each other, and when there are adjacent R10a groups, the two adjacent R10a groups, together with carbon atoms to which the R10a groups are attached, they may constitute a substituted or unsubstituted aliphatic ring, a substituted or unsubstituted aliphatic heterocyclic ring, a substituted or unsubstituted aromatic ring, a substituted or unsubstituted aromatic heterocyclic ring, or a substituted or unsubstituted fused polycyclic ring in which an aromatic ring or an aromatic heterocyclic ring is fused with these rings.

8. Photochromic compound according to claim 7,characterized by the fact that the photochromic compound is represented by formula (7) below: Chemical Formula 11 in formula (7) above, R5, R6, R7, R8, R10a, b, c and e1 are each the same as those in formula (6) above, Petition 870250084631, dated 19 / 09 / 2025, page. 196 / 223 12 / 22 R9 is a group represented by formula (1a) above, R9b is a hydroxy group, an alkyl group with 1 to 6 carbon atoms, a haloalkyl group with 1 to 6 carbon atoms, a cycloalkyl group with 3 to 8 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, a substituted or unsubstituted amino group, a substituted or unsubstituted heterocyclic group, a cyano group, a halogen atom, an alkylthio group with 1 to 6 carbon atoms, a substituted or unsubstituted arylthio group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a nitro group, a substituted or unsubstituted silyl group,a substituted or unsubstituted oxysyl group, a group represented by formula (2a) above, or a group represented by formula (X3) above, d2 is an integer from 0 to 4, when d2 is from 2 to 4, a plurality of R9b groups may be the same or different from each other, and when there are R9b groups adjacent to each other, the two adjacent R9b groups, together with carbon atoms to which the R9b groups are attached, may constitute a substituted or unsubstituted aliphatic ring, a substituted or unsubstituted aliphatic heterocyclic ring, a substituted or unsubstituted aromatic ring, a substituted or unsubstituted aromatic heterocyclic ring, or a substituted or unsubstituted fused polycyclic ring in which an aromatic ring or an aromatic heterocyclic ring is fused with these rings.

9. Photochromic compound according to claim 8, characterized in that the photochromic compound is represented by formula (8) below: Petition 870250084631,from 19 / 09 / 2025, page. 197 / 223 13 / 22 Chemical Formula 12 (8) In formula (8) above, R5, R6, R7, R8, R9, R9b, b, c and d2 are each the same as those in formula (7) above, R10 is an alkyl group with 1 to 6 carbon atoms, a haloalkyl group with 1 to 6 carbon atoms, a cycloalkyl group with 3 to 8 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, a substituted or unsubstituted amino group, a substituted or unsubstituted heterocyclic group, a halogen atom, an alkylthio group with 1 to 6 carbon atoms, a substituted or unsubstituted arylthio group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted oxysilyl group, a group represented by the formula (2a) above, or a group represented by formula (X3) above, R10b is a hydroxyl group,an alkyl group with 1 to 6 carbon atoms, a haloalkyl group with 1 to 6 carbon atoms, a cycloalkyl group with 3 to 8 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, a substituted or unsubstituted amino group, a substituted or unsubstituted heterocyclic group, a cyano group, a halogen atom, an alkylthio group with 1 to 6 carbon atoms, a substituted or unsubstituted arylthio group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a Petition 870250084631, dated 19 / 09 / 2025, p. 198 / 223 14 / 22 nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted oxysilyl group, a group represented by formula (2a) above, or a group represented by formula (X3) above, e2 is an integer from 0 to 4, when e2 is from 2 to 4, the plurality of R10b groups may be equal or different from each other,And when there are adjacent R10b groups, the two adjacent R10b groups, together with carbon atoms to which the R10b groups are attached, can constitute a substituted or unsubstituted aliphatic ring, a substituted or unsubstituted aliphatic heterocyclic ring, a substituted or unsubstituted aromatic ring, a substituted or unsubstituted aromatic heterocyclic ring, or a substituted or unsubstituted fused polycyclic ring in which an aromatic ring or an aromatic heterocyclic ring is fused with these rings.

10. Photochromic compound, according to claim 1, characterized in that R1 is a substituted or unsubstituted phenyl group.

11. Photochromic compound, according to claim 1, characterized in that R2 is a substituted or unsubstituted alkyl group having 1 or more and 10 or fewer carbon atoms, a substituted or unsubstituted cycloalkyl group having 5 or more and 10 or fewer carbon atoms,a substituted or unsubstituted haloalkyl group having 1 or more and 10 or fewer atoms, or a group represented by formula (2a) above.

12. Curable composition, characterized in that it comprises the photochromic compound, as defined in claim 1, and at least one selected from a group consisting of a radical polymerizable monomer, a cationic polymerizable monomer, a compound having a polymerizable group and a polymer of Petition 870250084631, dated 19 / 09 / 2025, page 199 / 223 15 / 22 (thio)urethane(urea).

13. Cured product, characterized in that the curable composition is as defined in claim 12.

14. Optical article, characterized in that it comprises the cured product as defined in claim 13.

15. Lens, characterized in that it comprises the photochromic compound, as defined in claim 1.

16. Eyeglasses, characterized in that it comprises the lens as defined in claim 15.

17. Propargyl alcohol compound,characterized by the fact that it is represented by the formula (9) below; Chemical Formula 13 <9> where, in formula (9) above, R3 is an aryl group or heteroaryl group substituted by a group represented by formula (1a) below, Chemical Formula 14 RÍ !Λ XN (1a) I R2 in formula (1a) above, R1 is a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted fused polycyclic ring in which an aromatic ring or an aromatic heterocyclic ring is fused with these substituents, R2 is a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted haloalkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkoxy group,a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted aralkyl group, or a group represented by formula (2a) below, -Q1 -(X1 Q2)a-X2 Q3 (2a) in formula (2a) above, Q1 is an alkylene group or a haloalkylene group, Q2 is an alkylene group or a haloalkylene group, Q3 is an alkyl group or a haloalkyl group, X1 and X2 are each independently O, S, NR700, PR701 or P(=O), R700 and R701 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, a is an integer of 0, or 1 or more and 3 or less, and R4 is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group.

18. Propargyl alcohol compound,according to claim 17, characterized in that the propargyl alcohol compound is represented by formula (10) below: Chemical Formula 15 in formula (10) above, Petition 870250084631, dated 09 / 19 / 2025, p. 201 / 223 17 / 22 R9a is a group represented by formula (1a) above, a hydrogen atom, a hydroxy group, an alkyl group with 1 to 6 carbon atoms, a haloalkyl group with 1 to 6 carbon atoms, a cycloalkyl group with 3 to 8 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, a substituted or unsubstituted amino group, a substituted or unsubstituted heterocyclic group, a cyano group, a halogen atom, an alkylthio group with 1 to 6 carbon atoms, a substituted or unsubstituted arylthio group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a nitro group, a substituted or unsubstituted silyl group,a substituted or unsubstituted oxysyl group, a group represented by formula (2a) above, or a group represented by formula (X3) above, L1-R 400 (X3) in formula (X3) above, R400 is a hydrogen atom, an alkyl group, an aryl group, a polymerizable group, a photochromic group or a silyl group having, as a substituent, an alkyl group, an alkoxy group or an aryl group, L1 is a group represented by formula (X2) below, Chemical Formula 16 in formula (X2) above, R30 is a group represented by formula (X2a) below, Petition 870250084631, dated 09 / 19 / 2025, page. 202 / 223 18 / 22 Chemical Formula 17 in formulas (X2) and (X2a) above, J represents a divalent group, each independently directly bonded, a substituted or unsubstituted methylene group, an oxygen atom, a sulfur atom or NR301, and R301 is a hydrogen atom or an alkyl group, L is an oxygen atom or a sulfur atom,R300 is an alkylene group or a silylene group having an alkyl group or an aryl group as a substituent, R302, r303 and r304 are each independently an alkylene group, h, j, kel are each independently an integer from 0 or 1, i is an integer from 1 to 200, when i is 2 or more, the structures of a plurality of R30 groups may be the same or different from each other, and the dashed lines indicate linkages with R400, d1 is an integer from 1 to 5, when d1 is 1, R9a is a group represented by formula (1a) above, when d1 is from 2 to 5, at least one of the plurality of R9a groups is a group represented by formula (1a) above, and the plurality of R9a groups may be the same or different from each other, when there are adjacent R9a groups, except for the group represented by formula (1a) above, the two adjacent R9a groups, together with carbon atoms to which the R9a groups are attached,They may constitute a substituted or non-substituted aliphatic ring. Petition 870250084631, dated 09 / 19 / 2025, p. 203 / 223 19 / 22 tuído, a substituted or unsubstituted aliphatic heterocyclic ring, a substituted or unsubstituted aromatic ring, a substituted or unsubstituted aromatic heterocyclic ring, or a substituted or unsubstituted fused polycyclic ring in which an aromatic ring or an aromatic heterocyclic ring is fused with these rings, R10a is a hydroxy group, an alkyl group with 1 to 6 carbon atoms, a haloalkyl group with 1 to 6 carbon atoms, a cycloalkyl group with 3 to 8 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, a substituted or unsubstituted amino group, a substituted or unsubstituted heterocyclic group, a cyano group, a halogen atom, an alkylthio group with 1 to 6 carbon atoms, a substituted or unsubstituted arylthio group, a substituted or unsubstituted aryloxy group,a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted oxysyl group, a group represented by formula (2a) above, or a group represented by formula (X3) above, e1 is an integer from 0 to 5, when e1 is from 2 to 5, the plurality of R10a may be equal or different from each other, and when there are R10a groups adjacent to each other, the two adjacent R10a groups, together with carbon atoms to which the R10a groups are attached, may constitute a substituted or unsubstituted aliphatic ring, a substituted or unsubstituted aliphatic heterocyclic ring, a substituted or unsubstituted aromatic ring, a substituted or unsubstituted aromatic heterocyclic ring,or a substituted or unsubstituted fused polycyclic ring in which an aromatic ring or an aromatic heterocyclic ring is fused with these rings.

19. Propargyl alcohol compound, as per Petition 870250084631, dated 09 / 19 / 2025, p. 204 / 223 20 / 22 claim 18, characterized in that the propargyl alcohol compound is represented by formula (11) below: Chemical Formula 18 in formula (11) above, R10a and e1 are the same as those in formula (10) above, R9 is a group represented by formula (1a) above, R9b is a hydroxy group, an alkyl group with 1 to 6 carbon atoms, a haloalkyl group with 1 to 6 carbon atoms, a cycloalkyl group with 3 to 8 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, a substituted or unsubstituted amino group, a substituted or unsubstituted heterocyclic group, a cyano group, a halogen atom, an alkylthio group with 1 to 6 carbon atoms, a substituted or unsubstituted arylthio group,a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted oxysilyl group, a group represented by formula (2a) above, or a group represented by formula (X3) above, d2 is an integer from 0 to 4, when d2 is from 2 to 4, the R9b groups may be the same or different from each other, and when there are R9b groups adjacent to each other, the two adjacent R9b groups, together with carbon atoms to which the R9b groups are attached, may constitute a substituted or unsubstituted aliphatic ring, a substituted or unsubstituted aliphatic heterocyclic ring Petition 870250084631, dated 19 / 09 / 2025, p. 205 / 223 21 / 22 substituted, a substituted or unsubstituted aromatic ring, a substituted or unsubstituted aromatic heterocyclic ring,or a substituted or unsubstituted fused polycyclic ring in which an aromatic ring or an aromatic heterocyclic ring is fused with these rings.

20. Propargyl alcohol compound according to claim 19, characterized in that the propargyl alcohol compound is represented by formula (12) below: Chemical Formula 19 (12) In formula (12) above, R9, R9b and d2 are the same as those in formula (11) above, R10 is an alkyl group with 1 to 6 carbon atoms, a haloalkyl group with 1 to 6 carbon atoms, a cycloalkyl group with 3 to 8 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, a substituted or unsubstituted amino group, a substituted or unsubstituted heterocyclic group, a halogen atom, an alkylthio group with 1 to 6 carbon atoms, a substituted or unsubstituted arylthio group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryl group,a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted oxysilyl group, a group represented by formula (2a) above, or a group represented by formula (X3) above, R10b is a hydroxyl group, an alkyl group with 1 to 6 carbon atoms, a haloalkyl group with 1 to 6 carbon atoms, a cycloalkyl group with 3 to 8 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, a substituted or unsubstituted amino group Petition 870250084631, dated 19 / 09 / 2025, p. 206 / 223 22 / 22 substituted, a substituted or unsubstituted heterocyclic group, a cyano group, a halogen atom, an alkylthio group with 1 to 6 carbon atoms, a substituted or unsubstituted arylthio group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a nitro group, a substituted or unsubstituted silyl group,a substituted or unsubstituted oxysyl group, a group represented by formula (2a) above, or a group represented by formula (X3) above, e2 is an integer from 0 to 4, when e2 is from 2 to 4, a plurality of R10b groups may be the same or different from each other, and when there are R10b groups adjacent to each other, the two adjacent R10b groups, together with carbon atoms to which the R10b groups are attached, may constitute a substituted or unsubstituted aliphatic ring, a substituted or unsubstituted aliphatic heterocyclic ring, a substituted or unsubstituted aromatic ring, a substituted or unsubstituted aromatic heterocyclic ring, or a substituted or unsubstituted fused polycyclic ring in which an aromatic ring or an aromatic heterocyclic ring is fused with these rings.

21. Propargyl alcohol compound according to claim 17, characterized in that R1 is a substituted or unsubstituted phenyl group,and R2 is a substituted or unsubstituted alkyl group having 1 or more and 10 or fewer carbon atoms, a substituted or unsubstituted cycloalkyl group having 5 or more and 10 or fewer carbon atoms, a substituted or unsubstituted haloalkyl group having 1 or more and 10 or fewer carbon atoms, or a group represented by formula (2a) above.