OPTICAL COMPOUNDS, SOLIDIFYING PREPARATIONS, OPTICAL INSTRUMENTS, LENSES AND OPTICAL GLASSES

Abstract

The invention relates to an optochromic compound with superior repeatability and superior solubility in a substrate; a curable composition containing an optochromic compound; an optical instrument; a lens; and eyeglasses. The implementation of the invention proposes an optochromic compound whose structure is represented by Formula (1). In Formula (1), M represents C, Si, or Ge. R1 represents a hydrogen atom or substituent. In the case where R1 is a substituent, that substituent is not a halogen atom or a trifluoromethyl group. R2 represents a hydrogen atom or substituent. In the case where R2 is a substituent, that substituent is not a halogen atom. Each R3 and R4 independently represents a straight-chain or branched alkyl group. R3 and R4 have different structures.

Description

Photochromic compound, curable composition, optical article, lens, and eyeglasses

[0001] The present invention relates to a photochromic compound, a curable composition, an optical article, a lens, and eyeglasses.

[0002] A photochromic compound is a compound that can reversibly convert into two isomers with different absorption spectra when irradiated with ultraviolet light, such as sunlight or light from a mercury lamp. Generally, when a colorless, bleached compound is irradiated with ultraviolet light, it quickly changes color and undergoes isomerization (coloring reaction) to a colored state. Photochromic compounds have been researched and developed, for example, as materials for photochromic lenses.

[0003] In such applications of photochromic lenses, the photochromic compound may be required to have the following properties: (I) A small degree of coloration in the visible light region before ultraviolet irradiation (hereinafter referred to as initial coloration); (II) A high speed at which the color density (hereinafter referred to as color density) reaches saturation after ultraviolet irradiation begins (hereinafter also referred to as high color sensitivity); (III) A high speed at which the compound returns to its original state after ultraviolet irradiation is stopped (hereinafter referred to as fading speed); and (IV) A high durability against repeated reversible action.

[0004] Many chromene compounds have been studied as photochromic compounds that satisfy these properties. For example, chromene compounds represented by the following formula (A) (Patent Document 1), chromene compounds represented by the following formula (B) (Patent Document 2), and chromene compounds represented by the following formula (C) (Patent Document 3) are known.

[0005] Photochromic lenses incorporating these photochromic compounds are manufactured by various methods. For example, there is a method of impregnating the lens surface with the photochromic compound. Another method is to use a cured product of a photochromic curable composition as a photochromic lens. Still another method is to obtain a photochromic laminate by laminating a photochromic layer, which is a cured product of the photochromic curable composition, on an optical substrate. Among these methods, the method of laminating a photochromic layer on an optical substrate is an advantageous method because it can be applied to various optical substrates. The photochromic curable composition contains, for example, a matrix material such as (meth)acrylate or isocyanate, and a photochromic compound (see Patent Documents 4, 5, and 6).

[0006]

[0007]

[0008]

[0009] International Publication No. WO 1996 / 014596 International Publication No. WO 2004 / 085568 International Publication No. WO 2011 / 053615 International Publication No. WO 2011 / 125956 International Publication No. WO 2020 / 094772 JP 2021-59681 A JP 2019-182866 A International Publication No. WO 2013 / 042800 International Publication No. WO 2015 / 035325 International Publication No. WO 2018 / 235771 JP 2018-62496 A International Publication No. WO 2021 / 075456 U.S. Patent Application Publication No. WO 2006 / 0022176 Specification WO 2016 / 143910

[0010] An object of the present invention is to provide a photochromic compound that is excellent in repetitive durability and solubility in a matrix material, and a curable composition, optical article, lens, and eyeglasses that contain this photochromic compound.

[0011] According to the present disclosure, there is provided a photochromic compound having a skeleton represented by the following formula (3):

[0012]

[0013] In formula (3), M is C, Si, or Ge. １ is a hydrogen atom or a substituent. １ When R is a substituent, it is not a halogen atom or a trifluoromethyl group. ２ is a hydrogen atom or a substituent. ２ When R is a substituent, it is not a halogen atom. ３ and R ４ are each independently a linear or branched alkyl group. ３ and R ４ have different structures. ５ and R ６ are each independently a hydrogen atom or a substituent. ７ and R ８ are each independently a substituent. b and c are each independently 0 or an integer of 1 to 3.

[0014] According to the present disclosure, there is provided a curable composition, which includes a photochromic compound according to an embodiment and at least one selected from the group consisting of a radical polymerizable monomer, a cationically polymerizable monomer, a compound having a polymerization reactive group, and a (thio)urethane (urea) polymer.

[0015] According to the present disclosure, an optical article is provided. The optical article includes a cured product of the curable composition.

[0016] According to the present disclosure, a lens is provided, the lens including a photochromic compound according to an embodiment.

[0017] According to the present disclosure, eyeglasses are provided, the eyeglasses including lenses according to an embodiment.

[0018] According to the present invention, there are provided a photochromic compound having excellent durability against repeated use and solubility, and a curable composition, optical article, lens, and eyeglasses containing this photochromic compound.

[0019] [Photochromic Compound] In a photochromic laminate, the photochromic layer may be required to be relatively thin in order to take advantage of the properties of the optical substrate. However, reducing the thickness of the photochromic layer may result in a decrease in repeated use durability. Furthermore, in order to achieve sufficient photochromic properties in a thin film, the photochromic compound must be dispersed in the photochromic layer at a high concentration. Therefore, in addition to the above requirements, the photochromic compound may also be required to have high solubility in the matrix material and high dispersibility within the matrix. On the other hand, photochromic compounds that are excessively soluble in the matrix material are difficult to crystallize, making it difficult to remove trace impurities by purification. The influence of these impurities may cause deterioration of the photochromic compound, making it difficult for the isomerization reaction of the photochromic compound to occur, i.e., reducing repeated use durability.

[0020] According to an embodiment, there is provided a photochromic compound having a skeleton represented by the following formula (3):

[0021]

[0022] In formula (3), M is C, Si, or Ge. １ is a hydrogen atom or a substituent. １ When R is a substituent, it will not be a halogen atom or a trifluoromethyl group. ２ is a hydrogen atom or a substituent. ２ When R is a substituent, it is not a halogen atom. ３ and R ４ are each independently a linear or branched alkyl group. ３ and R ４ have different structures. ５ and R ６ are each independently a hydrogen atom or a substituent. ７ and R ８ are each independently a substituent. b and c are each independently 0 or an integer of 1 to 3.

[0023] This photochromic compound has excellent durability against repeated use and solubility. The reason for this is not clear, but the present inventors believe it to be as follows.

[0024] The atom M at the 13th position of the photochromic compound according to the embodiment may be any of the above R ３ and R ４ is bonded. This R ３ and R ４ are alkyl groups, but have different structures. The solubility of a photochromic compound in a matrix material is thought to be affected by both the affinity with the matrix material and the flexibility of the crystalline structure of the photochromic compound. In the photochromic compounds according to the embodiments, the atom M at the 13th position is substituted with alkyl groups having different structures, which is thought to moderately reduce the symmetry of the molecule and weaken the intermolecular interactions of the photochromic compound. As a result, the flexibility of the crystalline structure of the photochromic compound is thought to be increased. Furthermore, since the crystallinity of the photochromic compound is not completely lost, a photochromic compound of high purity can be obtained by techniques such as recrystallization. Therefore, it is thought that the deterioration of the photochromic compound due to the influence of impurities can also be suppressed, thereby suppressing the decrease in repeated durability. Therefore, the photochromic compounds according to the embodiments can achieve high solubility in various matrix materials while exhibiting high durability.

[0025] Furthermore, as a result of intensive research, the present inventors have found that a substituent R ３ and R ４ That is, in the photochromic compound according to the embodiment, an alkyl group is directly bonded to atom M at the 13th position, and no oxygen atom is bonded thereto.

[0026] Therefore, the photochromic compound according to the embodiment has higher durability than a photochromic compound having a group into which a substituent has been introduced via an oxygen atom, such as an alkoxy group.

[0027] From the above, when the photochromic compound according to the embodiment is used, a photochromic curable composition having excellent solubility in the curable composition can be obtained, and a cured product or optical article having excellent durability can be realized.

[0028] The photochromic compound having the skeleton represented by formula (3) will be described in detail below. <M> In formula (3), M is C, Si, or Ge. M is preferably C.

[0029] <R １ > R １ is a hydrogen atom or a substituent. When it is a substituent, it is a halogen atom or a group other than a trifluoromethyl group. In other words, R １ is a substituent other than a halogen atom or a trifluoromethyl group, or a hydrogen atom.

[0030] R １ is a hydrogen atom, a hydroxyl group, a substituted or unsubstituted alkyl 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 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 the following formula (2a), a group represented by the following formula (X), or a group represented by the following formula (X3) is preferred.

[0031] R １is more preferably a hydrogen atom, a substituted or unsubstituted alkyl 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 substituted or unsubstituted alkylthio group, 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 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 the following formula (2a), a group represented by the following formula (X), or a group represented by the following formula (X3).

[0032] The alkyl group is preferably a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, more preferably an unsubstituted alkyl group having 1 to 10 carbon atoms, and even more preferably an unsubstituted alkyl group having 1 to 6 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.

[0033] The cycloalkyl group is preferably a cycloalkyl group having 3 to 8 carbon atoms (a cycloalkyl group having 3 to 8 carbon atoms forming a ring). Examples of cycloalkyl groups having 3 to 8 carbon atoms include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group. The cycloalkyl group may have a substituent, but the number of carbon atoms in the substituent is not included in the number of carbon atoms (3 to 8 carbon atoms).

[0034] The alkoxy group is preferably a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, more preferably an unsubstituted alkoxy group having 1 to 10 carbon atoms, and particularly preferably an alkoxy group having 1 to 6 carbon atoms. Examples of suitable alkoxy groups having 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, and a tert-butoxy group.

[0035] The amino group is a primary amino group (-NH２ ) or a secondary or tertiary amino group in which one or two hydrogen atoms have been substituted. Examples of the substituent on the substituted amino group include an alkyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 7 carbon atoms, an aryl group having 6 to 14 carbon atoms, and a heteroaryl group having 4 to 14 carbon atoms. Examples of suitable amino groups include an amino group, a methylamino group, a dimethylamino group, an ethylamino group, a diethylamino group, a methylphenylamino group, and a diphenylamino group.

[0036] The heterocyclic group is preferably a heterocyclic group having 3 to 10 atoms. The heteroatom of the heterocyclic group is preferably at least one selected from the group consisting of an oxygen atom, a nitrogen atom, a sulfur atom, and a phosphorus atom. The number of heteroatoms is, for example, 1 to 5, preferably 1 or 2. Specific examples include aliphatic heterocyclic groups such as a morpholino group, a piperidino group, a pyrrolidinyl group, a piperazino group, and an N-methylpiperazino group, and aromatic heterocyclic groups such as an indolinyl group. The heterocyclic group may be a 2,6-dimethylmorpholino group, a 2,6-dimethylpiperidino group, or a 2,2,6,6-tetramethylpiperidino group.

[0037] The alkylthio group is preferably an alkylthio group having 1 to 6 carbon atoms. Examples of the alkylthio group having 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, and a t-butylthio group.

[0038] The arylthio group is preferably an arylthio group having 6 to 10 carbon atoms. Examples of the arylthio group having 6 to 10 carbon atoms include a phenylthio group, a 1-naphthylthio group, and a 2-naphthylthio group.

[0039] The alkylcarbonyl group is preferably an alkylcarbonyl group having 2 to 7 carbon atoms. Examples of the alkylcarbonyl group having 2 to 7 carbon atoms include an acetyl group and an ethylcarbonyl group.

[0040] The alkoxycarbonyl group is preferably an alkoxycarbonyl group having 2 to 7 carbon atoms. Examples of the alkoxycarbonyl group having 2 to 7 carbon atoms include a methoxycarbonyl group and an ethoxycarbonyl group.

[0041] The aralkyl group is preferably an aralkyl group having 7 to 11 carbon atoms. Examples of the aralkyl group having 7 to 11 carbon atoms include a benzyl group, a phenylethyl group, a phenylpropyl group, a phenylbutyl group, and a naphthylmethyl group.

[0042] The aralkoxy group is preferably an aralkoxy group having 7 to 11 carbon atoms. Examples of the aralkoxy group having 7 to 11 carbon atoms include a benzyloxy group and a naphthylmethoxy group.

[0043] The aryloxy group is preferably an aryloxy group having 6 to 12 carbon atoms. Examples of the aryloxy group having 6 to 12 carbon atoms include a phenyloxy group and a naphthyloxy group.

[0044] The aryl group is not particularly limited, but is preferably an aryl group having 5 to 12 carbon atoms. Examples of the aryl group having 5 to 12 carbon atoms include a phenyl group, a 1-naphthyl group, and a 2-naphthyl group.

[0045] The heteroaryl group is not particularly limited, but is preferably a heteroaryl group having 3 to 12 carbon atoms. Examples of the heteroatom include at least one selected from the 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 to 3, preferably 1 or 2. The number of carbon atoms in the substituted or unsubstituted heteroaryl group is, for example, 4 to 11, preferably 5 to 9. Examples of heteroaryl groups having 3 to 12 carbon atoms include a thienyl group, a furyl group, a pyrrolinyl group, a pyridyl group, a benzothienyl group, a benzofuranyl group, and a benzopyrrolinyl group.

[0046] The alkoxyalkylthio group is preferably an alkoxyalkylthio group having 2 to 9 carbon atoms. Examples of the alkoxyalkylthio group having 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, and an n-propoxypropylthio group.

[0047] The haloalkylthio group is preferably a haloalkylthio group having 1 to 6 carbon atoms. Examples of the haloalkylthio group having 1 to 6 carbon atoms include a trifluoromethylthio group, a tetrafluoroethylthio group, a chloromethylthio group, a 2-chloroethylthio group, and a bromomethylthio group.

[0048] The cycloalkylthio group is preferably a cycloalkylthio group having 3 to 8 carbon atoms. Examples of the cycloalkylthio group having 3 to 8 carbon atoms include a cyclopropylthio group, a cyclobutylthio group, a cyclopentylthio group, and a cyclohexylthio group. The cycloalkylthio group may have a substituent, but the number of carbon atoms in the substituent is not included in the number of carbon atoms (3 to 8 carbon atoms).

[0049] The silyl group may have a substituent. The substituent of the substituted silyl group is not particularly limited, and examples thereof include an alkyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 7 carbon atoms, an aryl group having 6 to 14 carbon atoms, and a heteroaryl group having 4 to 14 carbon atoms.

[0050] The oxysilyl group may have a substituent. The substituent of the substituted oxysilyl group is not particularly limited, and examples thereof include an alkyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 7 carbon atoms, an aryl group having 6 to 14 carbon atoms, and a heteroaryl group having 4 to 14 carbon atoms.

[0051] (Group represented by formula (2a)) -Q １ -(X １ Q ２ ) a-X ２ Q ３(2a) In formula (2a), Q １ is an alkylene group or a haloalkylene group.

[0052] The number of carbon atoms in the alkylene group is preferably 1 to 20, more preferably 1 to 12, even more preferably 1 to 7, and most preferably 2 to 6. As the halogen atom of the haloalkylene group, at least one selected from the group consisting of I, Cl, Br, and F can be used. The halogen atom is preferably at least one of Cl and F, and more preferably F. In the haloalkylene group, the halogen atom is preferably bonded to the terminal carbon, and the terminal is more preferably a perfluoromethyl group.

[0053] Q ２ is an alkylene group or a haloalkylene group. A preferred embodiment of the alkylene group or the haloalkylene group is １ It is the same as: ２ The number of carbon atoms in the alkylene group or haloalkylene group is １ The number of carbon atoms in the alkylene group or haloalkylene group may be the same as or different from that of the alkylene group or haloalkylene group.

[0054] Q ３ is an alkyl group or a haloalkyl group, which may be linear or branched, but is preferably linear.

[0055] The number of carbon atoms in the alkyl group is preferably 1 to 20, more preferably 1 to 12, and most preferably 1 to 7. The halogen atom in the haloalkyl group can be at least one selected from the group consisting of I, Cl, Br, and F. The halogen atom is preferably at least one of Cl and F, and more preferably F.

[0056] Q ３ is preferably a straight chain alkyl group.

[0057] X １ , and X ２ are each independently O, S, or NR ７００ , P.R. ７０１ , or P(=O). X１ , and X ２ is O, S, or NR ７００ is preferred, and O is most preferred.

[0058] R ７００ and R ７０１ 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.

[0059] R ７００ 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.

[0060] R ７０１ 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.

[0061] a is 0 or an integer of 1 or more and 3 or less.

[0062] Formula (2a) is preferably an alkylenealkoxy group, an alkylenethioalkyl group, or an alkyleneoxyalkylenealkoxy group.

[0063] Specific examples of formula (2a) include -CH ２ OCH ３ , -CH ２ SCH ３ , -CH ２ CH ２ OCH ３ , -CH ２ CH ２ OCH ２ CH ３ , -CH ２ CH ２ SCH ３ , -CH ２ CH ２ CH ２ OCH３ , -CH ２ CH ２ CH ２ SCH ３、 -CH ２ CH ２ OCH ２ CH ２ OCH ３、 and -CH ２ CH ２ OCH ２ CH ２ OCH ２ CH ３ Examples include:

[0064] The group represented by formula (2a) is —CH ２ OCH ３ , -CH ２ CH ２ OCH ３ , -CH ２ CH ２ OCH ２ CH ３ , -CH ２ CH ２ CH ２ OCH ３ , -CH ２ CH ２ OCH ２ CH ２ OCH ３、 Or, -CH ２ CH ２ OCH ２ CH ２ OCH ２ CH ３ is preferred.

[0065] (Group represented by formula (X))

[0066]

[0067] In formula (X), E is an oxygen atom or NR １０１ It is. １０１ is a hydrogen atom or an alkyl group. １０１ and R １０１ is preferably a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.

[0068] F is an oxygen atom or a sulfur atom, and preferably an oxygen atom.

[0069] G is an oxygen atom, a sulfur atom, or NR ２０２ It is. ２０２ is a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a heteroaryl group. G is preferably NH.

[0070] g is 0 or 1.

[0071] R ２０１ 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, R ２０１ is a group other than a hydrogen atom. ２０１ is preferably an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, or an aryl group having 6 to 12 carbon atoms.

[0072] Suitable groups of formula (X) are as follows:

[0073]

[0074] (Group represented by formula (X3)) L １ -R ４００ (X3) In formula (X3), R ４００ is a hydrogen atom, an alkyl group, an aryl group, a polymerizable group, a photochromic group, or a silyl group having an alkyl group, an alkoxy group, or an aryl group as a substituent.

[0075] L １ is a group represented by the following formula (X2).

[0076]

[0077] In formula (X2), R ３０ is a group represented by the following formula (X2a).

[0078]

[0079] In formula (X2) and formula (X2a), J is a divalent group. Each of the plurality of Js independently represents a direct bond, a substituted or unsubstituted methylene group, an oxygen atom, a sulfur atom, or an NR ３０１ It is. ３０１is a hydrogen atom or an alkyl group. ３０１ is preferably an alkyl group having 1 to 20 carbon atoms. This alkyl group preferably has, as a substituent, a silyl group having an alkyl group having 1 to 10 carbon atoms, a polymerizable group, or a photochromic group.

[0080] Examples of the polymerizable group include radically polymerizable groups such as vinyl group, 1-chlorovinyl group, allyl group, styryl group, (meth)acrylic group, 2-(methacryloxy)ethylcarbamyl group, 2-(methacryloxy)ethoxycarbonyl group, and crotyl group. In addition to these, other radically polymerizable groups include epoxy group, episulfide group, thietanyl group, OH group, SH group, and NH ２ Examples of the polymerizable group include a (meth)acrylic group, a 2-(methacryloxy)ethylcarbamyl group, a 2-(methacryloxy)ethoxycarbonyl group, an epoxy group, an OH group, an SH group, an NH ２ At least one selected from the group consisting of a group and a COOH group is preferred.

[0081] The photochromic group is a group containing a photochromic moiety. Representative examples of the photochromic group include naphthopyran, spirooxazine, spiropyran, fulgide, fulgimide, and diarylethene. In terms of being able to exhibit excellent photochromic properties, indenonaphthopyran is preferred, and among these, indeno[2,1-f]naphtho[1,2-b]pyran is particularly preferred.

[0082] The indeno[2,1-f]naphtho[1,2-b]pyran is preferably a group represented by the following formula (X4):

[0083]

[0084] In formula (X4), R ４０１ and R ４０２ is the R ３ and R ４ The group may be the same as the group used in

[0085] R ４０３ and R ４０４ are each independently R３ and R ４ The group may be the same as the group used in

[0086] R ４０５ and R ４０６ are each independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. ４０５ and R ４０６ is R ５ and R ６ The group may be the same as the group used in

[0087] In formula (X4), o is an integer of 0 to 4. n is an integer of 0 to 4. When o is 2 to 4, a plurality of R ４０３ may be the same or different. When n is 2 or more and 4 or less, a plurality of R ４０４ may be the same or different from each other.

[0088] R ４０１ , R ４０２ , R ４０３ , R ４０４ , R ４０５ , and R ４０６ is a group represented by formula (X3), at least one of the substituents on the aryl group or heteroaryl group is L １ and combine.

[0089] Particularly preferred groups of formula (X2) are represented by the following formula:

[0090]

[0091] In formula (X2), L is an oxygen atom or a sulfur atom.

[0092] R ３００ is an alkylene group or a silylene group having an alkyl group or an aryl group as a substituent. ３００ is preferably an alkylene group having 1 to 6 carbon atoms or a silylene group having an alkyl group having 1 to 6 carbon atoms as a substituent.

[0093] R ３０２ , R ３０３ , and R ３０４are each independently an alkylene group. ３０２ is preferably an alkylene group having 1 to 6 carbon atoms. ３０３ is preferably an alkylene group having 1 to 6 carbon atoms. ３０４ is preferably an alkylene group having 1 to 6 carbon atoms.

[0094] h, j, k and l each independently represent 0 or 1.

[0095] "i" is an integer of 0 to 200. The structures of groups to which multiple "i"s are attached may be the same or different. "i" is preferably a number in the range of 5 to 100, more preferably 8 to 75, and most preferably 10 to 70.

[0096] In formula (X2), the dashed line represents R ４００ Represents a bond with.

[0097] <R ２ > R ２ is a hydrogen atom or a substituent. When it is a substituent, it is a group other than a halogen atom. In other words, R ２ is a substituent other than a halogen atom, or a hydrogen atom.

[0098] R ２ Is 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 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 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), a group represented by formula (X), or a group represented by formula (X3) is preferred.

[0099] The haloalkyl group is preferably a haloalkyl group having 1 to 6 carbon atoms. The number of halogen atoms is preferably 1 to 10, and more preferably 2 to 5. The haloalkyl group having 1 to 6 carbon atoms is preferably an alkyl group substituted with a fluorine atom, a chlorine atom, or a bromine atom. The haloalkyl group preferably has a terminal perfluoromethyl group. Examples of suitable haloalkyl groups include a trifluoromethyl group, a trifluoroethyl group, a trifluoropropyl group, a tetrafluoroethyl group, a chloromethyl group, a 2-chloroethyl group, and a bromomethyl group.

[0100] Specific preferred groups as the alkyl group, cycloalkyl group, alkoxy group, amino group, heterocyclic group, alkylthio group, arylthio group, alkylcarbonyl group, alkoxycarbonyl group, aralkyl group, aralkoxy group, aryloxy group, heteroaryl group, silyl group, oxysilyl group, group represented by formula (2a), group represented by formula (X), and group represented by formula (X3) include R １ Examples of the groups include the same as those exemplified in the above.

[0101] <R ３ and R ４ > R ３ and R ４ R are each independently a linear or branched unsubstituted alkyl group and have mutually different structures. ４ The number of carbon atoms in the alkyl group of R ３ The number of carbon atoms in the alkyl group may be equal to or greater than the number of carbon atoms in the alkyl group.

[0102] That is, R ３ When R is a linear alkyl group, ４ is R ３ or a linear alkyl group having a carbon number greater than R ３ The alkyl group is a branched alkyl group having the same or more carbon atoms.

[0103] Also, R ３ When R is a branched alkyl group, ４ is R ３ or a linear alkyl group having the same or more carbon atoms as R ４ is R３ and a branched alkyl group having the same or more carbon atoms as, but different from, the alkyl group.

[0104] Furthermore, R ３ and R ４ When both are branched alkyl groups having 4 or more carbon atoms, R ４ The number of carbon atoms in the alkyl group of R ３ As long as the condition that the number of carbon atoms in the alkyl group R is equal to or greater than the number of carbon atoms in the alkyl group R is satisfied, ３ The number of carbon atoms in the main chain of R ４ The number of carbon atoms in the main chain of R may be larger than that of R. ３ and R ４ and the number of carbon atoms in the alkyl groups are the same, the branched alkyl group having a structure in which the substitution position of the branched alkyl group relative to the main chain is closer to M in formula (3) is selected as R ３ Let's say.

[0105] For example, when the branched alkyl group substituting M is an s-butyl group and an isobutyl group, the s-butyl group is R ３ and the isobutyl group is R ４ This becomes:

[0106] R ３ The number of carbon atoms in R is preferably 1 to 19, more preferably 1 to 10, even more preferably 1 to 9, particularly preferably 1 to 6, and most preferably 1 to 3. When the number of carbon atoms is small, the durability for repeated use tends to be high. When the number of carbon atoms is large, the solubility tends to be high. ３ is preferably a linear alkyl group.

[0107] R ３ When is a branched alkyl group, the number of branches is preferably 5 or less, more preferably 3 or less, and even more preferably 1.

[0108] The number of carbon atoms in the side chain is preferably 5 or less, more preferably 3 or less, more preferably 2 or less, and particularly preferably 1.

[0109] R ４The number of carbon atoms in R is preferably 2 to 20, more preferably 2 to 11, even more preferably 2 to 10, particularly preferably 2 to 7, and most preferably 2 to 4. When the number of carbon atoms is small, the durability for repeated use tends to be high. When the number of carbon atoms is large, the solubility tends to be high. ４ is preferably a linear alkyl group.

[0110] R ４ From the number of carbon atoms in the alkyl group, R ３ The value obtained by subtracting the number of carbon atoms in the alkyl group from the above is preferably 1 or more and 15 or less, more preferably 1 or more and 10 or less, more preferably 1 or more and 9 or less, even more preferably 1 or more and 5 or less, particularly preferably 1 or more and 3 or less, and most preferably 1 or more and 2 or less. When this subtraction value is small, repeated durability tends to be increased. When this subtraction value is large, solubility tends to be increased.

[0111] R ３ and R ４ As a combination of ３ is a linear or branched alkyl group having 1 to 19 carbon atoms, and R ４ is preferably a linear or branched alkyl group having 2 to 20 carbon atoms, and R ３ is a linear alkyl group having 1 to 19 carbon atoms, and R ４ is more preferably a linear or branched alkyl group having 2 to 20 carbon atoms, and R ３ is a linear alkyl group having 1 to 19 carbon atoms, and R ４ is more preferably a linear alkyl group having 2 to 20 carbon atoms, and R ３ is a linear alkyl group having 1 to 9 carbon atoms, and R ４ is more preferably a linear alkyl group having 2 to 10 carbon atoms, and R ３ is a linear alkyl group having 1 to 6 carbon atoms, and R ４ is more preferably a linear alkyl group having 2 to 10 carbon atoms, and R ３ is a linear alkyl group having 1 to 3 carbon atoms, and R ４ is more preferably a linear alkyl group having 2 to 10 carbon atoms, and R３ is a linear alkyl group having 1 to 3 carbon atoms, and R ４ is more preferably a linear alkyl group having 2 to 7 carbon atoms, and R ３ is a linear alkyl group having 1 to 3 carbon atoms, and R ４ is more preferably a linear alkyl group having 2 to 4 carbon atoms, and R ３ and R ４ It is most preferable that either one of the above is an ethyl group.

[0112] <R ７ , and R ８ > R ７ and R ８ are each independently a substituent. b and c are each independently 0 or an integer of 1 to 3. In formula (2), R ７ and R ８ are, for example, each independently 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, an alkylthio group, a substituted or unsubstituted arylthio group, a nitro group, a formyl group, a hydroxycarbonyl group, an alkylcarbonyl group, an 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, an 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), a group represented by formula (X), or a group represented by formula (X3). These groups include R １ ~R ４ The same groups as those exemplified in the above can be used.

[0113] In formula (2), when b is 2 or 3, a plurality of R ７ may be the same or different from each other.

[0114] In formula (2), b is 2 to 3, and adjacent R７ If there is a ７ is R ７ and the carbon atom bonded thereto may form a substituted or unsubstituted aliphatic ring, a substituted or unsubstituted aliphatic heterocycle, a substituted or unsubstituted aromatic ring, a substituted or unsubstituted aromatic heterocycle, or a substituted or unsubstituted fused polycycle in which an aromatic ring or an aromatic heterocycle is fused to any of these rings. ７ The combination of these is at the 7th and 8th positions of the naphthopyran skeleton.

[0115] Furthermore, R １ and adjacent R ７ If there is an adjacent R １ and R ７ may form, together with the carbon atom to which they are bonded, a substituted or unsubstituted aliphatic ring, a substituted or unsubstituted aliphatic heterocycle, a substituted or unsubstituted aromatic ring, a substituted or unsubstituted aromatic heterocycle, or a substituted or unsubstituted fused polycycle in which an aromatic ring or an aromatic heterocycle is fused to any of these rings. １ and R ７ The combinations are the 5th and 6th positions, and the 6th and 7th positions of the naphthopyran skeleton.

[0116] In formula (2), when c is 2 to 3, a plurality of R ８ may be the same or different from each other.

[0117] In formula (2), c is 2 to 3, and adjacent R ８ If there is a ８ is R ８ and the carbon atom bonded thereto may form a substituted or unsubstituted aliphatic ring, a substituted or unsubstituted aliphatic heterocycle, a substituted or unsubstituted aromatic ring, a substituted or unsubstituted aromatic heterocycle, or a substituted or unsubstituted fused polycycle in which an aromatic ring or an aromatic heterocycle is fused to any of these rings. ８ The combination of is at the 11th and 12th positions of the naphthopyran compound.

[0118] Furthermore, R ２ and adjacent R ８ If there is an adjacent R２ and R ８ may form, together with the carbon atom to which they are bonded, a substituted or unsubstituted aliphatic ring, a substituted or unsubstituted aliphatic heterocycle, a substituted or unsubstituted aromatic ring, a substituted or unsubstituted aromatic heterocycle, or a substituted or unsubstituted fused polycycle in which an aromatic ring or an aromatic heterocycle is fused to any of these rings. ２ and R ８ The combinations are the 9th and 10th positions, and the 10th and 11th positions of the naphthopyran skeleton.

[0119] R ７ or R ８ may form a ring having 5 to 8 atoms, including the carbon atom to which it is bonded. The ring may have a substituent, and examples of the substituent include a substituent selected from a hydroxyl group, an alkyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an amino group, a substituted amino group, a heterocyclic group having 3 to 8 atoms, a cyano group, a nitro group, and a halogen atom. Specific examples of these substituents will be described later.

[0120] R ７ or R ８ A preferred ring formed by the formula (X5) is a ring represented by the following formula (X5).

[0121]

[0122] In formula (X5), Q and T each independently represent a sulfur atom, a substituted or unsubstituted methylene group, an oxygen atom, or NR ３０７ R ３０７ represents a hydrogen atom, a hydroxyl 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).

[0123] R ３０５ and R ３０６are 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.

[0124] Also, R ３０５ and R ３０６ may form a substituted or unsubstituted aliphatic ring together with the carbon atom to which they are bonded. Specific examples of the aliphatic ring include a cyclopentane ring and a cyclohexane ring. In addition, in the aliphatic ring, 1 to 8 hydrogen atoms, and particularly preferably 1 to 4 hydrogen atoms, may be substituted with at least one group selected from the 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.

[0125] In formula (X5), m is an integer of 1 or more and 4 or less.

[0126] <R ５ and R ６ > R ５ and R ６ are each independently a hydrogen atom or a substituent. １ In formula (3), the substituents exemplified in ５ and R ６ are, for example, each independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. １ The same groups as those exemplified in the above can be used.

[0127] R ５ and R ６are each independently 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. ５ and R ６ Preferably, at least one of R is a substituted or unsubstituted phenyl group. ５ and R ６ More preferably, both are substituted phenyl groups.

[0128] The substituent on the phenyl group is preferably a group represented by formula (2a), a hydroxyl group, an alkyl group, a haloalkyl group, a substituted or unsubstituted cycloalkyl group, an alkoxy group, an amino group, a substituted amino group, a substituted or unsubstituted heterocyclic group, a cyano group, a halogen atom, an alkylthio group, a substituted or unsubstituted arylthio group, a nitro group, a formyl group, a hydroxycarbonyl group, an alkylcarbonyl group, an 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, an alkoxyalkylthio group, a haloalkylthio group, a substituted or unsubstituted cycloalkylthio group, a substituted or unsubstituted silyl group, a substituted or unsubstituted oxysilyl group, or a group represented by formula (X3).

[0129] The substituent on the phenyl group is more preferably an alkyl group, a haloalkyl group, an alkoxy group, an amino group, a substituted amino group, a substituted or unsubstituted heterocyclic group, a cyano group, a halogen atom, an alkylthio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, an alkoxyalkylthio group, a haloalkylthio group, a substituted or unsubstituted silyl group, a substituted or unsubstituted oxysilyl group, or a group represented by formula (X3).

[0130] <Photochromic Compound Represented by Formula (4)> Suitable photochromic compounds include compounds represented by the following formula (4).

[0131] In formula (4), R １ , R ２ , R ３ , R ４ , R ７ , R ８ , b, c and M each independently have the same meaning as in formula (3).

[0132]

[0133] <R ９ and R １０ > R ９ and R １０ are each independently a hydroxyl group, an alkyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a substituted or unsubstituted amino group, a heterocyclic group, a cyano group, a halogen atom, an alkylthio group having 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), or a group represented by formula (X3).

[0134] d is R ９ and is an integer of 0 to 5. When d is 2 or more, R ９ may be the same or different groups.

[0135] d is 2 or more and 5 or less, and adjacent R ９ If there is a ９ Together they ９ and the carbon atom bonded to the ring may form a substituted or unsubstituted aliphatic ring, a substituted or unsubstituted aliphatic heterocycle, a substituted or unsubstituted aromatic ring, a substituted or unsubstituted aromatic heterocycle, or a substituted or unsubstituted fused polycycle in which an aromatic ring or an aromatic heterocycle is fused to any of these rings.

[0136] e is R １０ and is an integer of 0 to 5. When e is 2 or more, R １０ may be the same or different groups.

[0137] e is 2 or more and 5 or less, and adjacent R １０ If there is a １０ is R １０ and the carbon atom bonded to the ring may form a substituted or unsubstituted aliphatic ring, a substituted or unsubstituted aliphatic heterocycle, a substituted or unsubstituted aromatic ring, a substituted or unsubstituted aromatic heterocycle, or a substituted or unsubstituted fused polycycle in which an aromatic ring or an aromatic heterocycle is fused to any of these rings.

[0138] R ９ and R １０ are each independently, and two adjacent ones can join together to form a cyclic group which may contain at least one atom selected from the group consisting of an oxygen atom, a sulfur atom, a carbon atom, and a nitrogen atom. This cyclic group is not particularly limited, but ９ and R １０ It is preferable that the ring has 5 to 8 atoms, including the carbon atom to which R is bonded. The ring may have a substituent. Examples of the substituent include a substituent selected from a hydroxyl group, an alkyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an amino group, a substituted amino group, a heterocyclic group having 3 to 8 atoms, a cyano group, a nitro group, and a halogen atom. Specific examples of these substituents include R １ ~R ４ The same groups as those exemplified in the group R ９ and R １０ The ring formed by these preferably forms a ring represented by formula (X5) together.

[0139] <Photochromic Compound Represented by Formula (5)> A particularly suitable photochromic compound is a compound represented by the following formula (5). In formula (5), R １ , R ２ , R３ , R ４ , R ７ , R ８ , R ９ , R １０ , d, and e each independently have the same meaning as in formula (4).

[0140]

[0141] <Z １ and Z ２ > Z １ and Z ２ 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 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 (2a), a group represented by formula (X), or a group represented by formula (X3).

[0142] In formula (5), bb is R ７ and is an integer of 0 to 2. When bb is 2, R ７ may be the same or different groups. ８ and is an integer of 0 to 2. When cc is 2, R ８ may be the same or different groups.

[0143] Among the photochromic compounds represented by formula (5), R ２is a hydrogen atom, that is, a structure in which the 10-position is unsubstituted, and ２ is a hydrogen atom, bb is 0, and cc is 0, that is, a structure represented by the following formula (6) is more preferred.

[0144]

[0145] In formula (6), R １ , R ２ , R ３ , R ４ , R ９ , R １０ , Z １ , Z ２ , d and e each independently have the same meaning as in formula (5).

[0146] Z ２ Is 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 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 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), a group represented by formula (X), or a group represented by formula (X3) is preferably a group.

[0147] Z ２represents a hydrogen atom, 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 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 aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted more preferably an alkoxyalkylthio group, a haloalkylthio group, a substituted or unsubstituted silyl group, a group represented by formula (2a), a group represented by formula (X), or a group represented by formula (X3), and even more preferably a hydrogen atom, a substituted or unsubstituted alkyl group, a haloalkyl 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 aryl group, a substituted or unsubstituted heteroaryl group, a haloalkylthio group, a group represented by formula (2a), or a group represented by formula (X3).

[0148] <Detailed Description of Substituents, etc.> The above-mentioned R １ ~R １０ , Z １ and Z ２ Examples of the substituent that the group may have include a hydroxyl 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, an aralkoxy group, an aryloxy group, an aryl group, a heteroaryl group, an alkoxyalkylthio group, a haloalkylthio group, a cycloalkylthio group, a silyl group, or an oxysilyl group. １ ~R ４The same as those detailed in 1. can be used.

[0149] <Specific Examples of Suitable Photochromic Compounds> Specific examples of particularly suitable photochromic compounds include photochromic compounds represented by the following formulas.

[0150]

[0151] [Method for producing photochromic compound] The photochromic compound according to the embodiment may be produced by any synthesis method. A typical example of a method for producing a photochromic compound will be described, but the method is not limited to this method. In the following description, the symbols in each formula have the same meaning as those described for the formula above, unless otherwise specified.

[0152] The photochromic compound can be produced by reacting a naphthol derivative represented by the following formula (7) with a propargyl alcohol compound represented by the following formula (8) in the presence of an acid catalyst.

[0153]

[0154]

[0155] The reaction ratio of the naphthol derivative to the propargyl alcohol compound is preferably selected from the range of 1:10 to 10:1 (molar ratio). Examples of the acid catalyst that can be used include sulfuric acid, benzenesulfonic acid, p-toluenesulfonic acid, and acidic alumina. The acid catalyst is used in an amount of preferably 0.1 to 10 parts by weight per 100 parts by weight of the total of the naphthol derivative and the propargyl alcohol compound. The reaction temperature is preferably 0 to 200°C. The solvent is preferably an aprotic organic solvent, such as N-methylpyrrolidone, dimethylformamide, tetrahydrofuran, benzene, or toluene. The purification method for the product obtained by this reaction is not particularly limited. For example, the product can be purified by silica gel column purification followed by recrystallization.

[0156] <Method for Synthesizing Naphthol Derivatives> Naphthol derivatives can be synthesized by known methods.

[0157] The method for synthesizing the naphthol derivative represented by formula (7) is not particularly limited, but for example, when M is a carbon atom, it can be synthesized as follows: First, a benzene compound represented by formula (9) below is reacted with an acid chloride compound represented by formula (10) below to obtain a benzophenone compound represented by formula (11) below. １ , R ２ , R ７ , R ８ , b and c have the same meanings as in formula (3).

[0158]

[0159]

[0160]

[0161] Depending on the structure and substituents of the photochromic compound to be synthesized, the substituents of the acid chloride compound and the benzene compound may be interchanged.

[0162] Furthermore, the benzophenone compound (11) is subjected to a Stobbe reaction, a cyclization reaction, a hydrolysis reaction using an alkali or an acid, benzyl protection, or debenzylation by hydrolysis reaction using an alkali or an acid to obtain a carboxylic acid represented by the following formula (12) in which the hydroxyl group is protected with benzyl (Bn).

[0163]

[0164] Next, the benzyl-protected carboxylic acid represented by formula (12) is converted to an amine by a method such as Curtius rearrangement, Hofmann rearrangement, or Lossen rearrangement, and a diazonium salt is prepared from the amine. This diazonium salt is then converted to a halide such as a bromide or iodide by a method such as the Sandmeyer reaction, to obtain a halide represented by formula (13) below (wherein Hal represents a halogen).

[0165]

[0166] The obtained halide is reacted with magnesium, lithium, or the like to prepare an organometallic reagent. This organometallic reagent is represented by the following formula (14) (wherein R ３ and R ４ has the same meaning as in formula (3)) in an organic solvent at −100 to 70° C. to obtain a compound represented by the following formula (15).

[0167]

[0168]

[0169] The resulting compound represented by formula (15) is debenzylated, followed by reaction under neutral to acidic conditions at 10 to 120°C for 10 minutes to 2 hours to spirate the alcohol, thereby synthesizing the desired naphthol derivative represented by formula (7). In this reaction, the reaction ratio of the organometallic reagent to the ketone represented by formula (14) can be varied over a wide range, but is preferably selected from a molar ratio of 1:10 to 10:1. The reaction temperature is preferably −100 to 70°C. Preferred solvents include aprotic organic solvents such as diethyl ether, tetrahydrofuran, benzene, and toluene. Spiration of the alcohol under neutral to acidic conditions is preferably carried out in the presence of an acid catalyst. Examples of acid catalysts that can be used include acetic acid, hydrochloric acid, sulfuric acid, benzenesulfonic acid, p-toluenesulfonic acid, and acidic alumina. Such acid catalysts are preferably used in an amount of 0.1 to 10 parts by weight per 100 parts by weight of the alcohol. The spiro reaction is preferably carried out in the presence of a solvent such as tetrahydrofuran, benzene, or toluene.

[0170] <Method for synthesizing naphthol derivatives containing Si or Ge> An example of a method for producing a naphthol derivative in which M in formula (7) is Si or Ge will be described below.

[0171] First, the halide represented by formula (13) is reacted with magnesium, lithium, or the like to prepare an organometallic reagent. This organometallic reagent is then converted into a compound represented by the following formula (16) (wherein R ３ and R ４has the same meaning as in formula (7)) in an organic solvent at −100 to 70° C. to obtain a compound represented by the following formula (17):

[0172]

[0173]

[0174] The resulting compound represented by formula (17) is used to obtain a cyclized product represented by formula (18) below by a known method.

[0175]

[0176] The resulting cyclized product is debenzylated to give the naphthol derivative represented by formula (7).

[0177] <Specific Examples of Naphthol Derivatives> Specific examples of naphthol derivatives include compounds represented by the following formula.

[0178]

[0179] <Identification of Photochromic Compound> The photochromic compound according to the embodiment is, for example, a solid or a viscous liquid at room temperature and normal pressure. From this solid or liquid, the photochromic compound can be isolated by a separation procedure such as thin layer chromatography, silica gel column chromatography, high performance liquid chromatography, or gas chromatography. In addition, it is confirmed that there are no by-products such as raw material compounds and coloring matters other than the photochromic compound.

[0180] The obtained photochromic compound was analyzed by proton nuclear magnetic resonance spectroscopy ( １ By measuring the photochromic compound by H-NMR, peaks due to aromatic protons and alkene protons appear around δ: 5.0 to 9.0 ppm, and peaks due to alkyl and alkylene protons appear around δ: 1.0 to 4.0 ppm. Furthermore, by comparing the respective spectral intensities relatively, the number of protons in each bonding group can be determined. This allows the skeleton and substituents of the photochromic compound to be identified.

[0181] Furthermore, when the photochromic compound is contained in a cured product such as a resin, the photochromic compound can be isolated by dissolving the resin and using the above-mentioned separation means.

[0182] <Photochromic Composition> The photochromic compound according to the embodiment can be dissolved in a common organic solvent such as toluene, chloroform, or tetrahydrofuran. When a photochromic compound having a skeleton represented by formula (3) is dissolved in such a solvent, a colorless, transparent solution is obtained. When this solution is irradiated with sunlight or ultraviolet light, it rapidly develops color, and when the sunlight or the like is blocked, it exhibits good photochromic action, rapidly and reversibly returning to its original colorless state.

[0183] The photochromic compound according to the embodiment can be used in combination with photochromic compounds having other structures depending on the intended application. For example, it can be used in combination with other photochromic compounds to obtain various color tones required for a photochromic lens. Known photochromic compounds can be used without any limitations as the photochromic compound to be combined. Examples include indenonaphthopyran, naphthopyran, spirooxazine, spiropyran, fulgide, fulgimide, and diarylethene. Among these, indenonaphthopyran compounds are particularly preferred because they can maintain a uniform color tone during color development and fading, suppress color shift during color development due to deterioration of photochromic properties, and further reduce initial coloring. It is preferable to use multiple photochromic compounds to adjust the color tone, particularly because they can achieve both high color density and fast fading speed at high temperatures and also have excellent durability.

[0184] When a photochromic composition containing the photochromic compound according to the embodiment and other photochromic compounds is prepared, the blending ratio of each photochromic compound is appropriately determined depending on the desired color tone.

[0185] <Photochromic Curable Composition> The curable composition according to the embodiment includes the photochromic compound according to the embodiment and at least one selected from the group consisting of a radical polymerizable monomer, a cationically polymerizable monomer, a compound having a polymerization reactive group, and a (thio)urethane (urea) polymer. Here, the (thio)urethane (urea) polymer includes at least one selected from the group consisting of a urethane polymer, a thiourethane polymer, a urethane urea polymer, and a thiourethane urea polymer.

[0186] The photochromic compound and photochromic composition according to the embodiment are preferably used in combination with a polymerizable compound as a photochromic curable composition.

[0187] The amount of the photochromic curable composition used depends on the color intensity of the photochromic compound, the selected lens material, and the lens thickness, and cannot be generalized; however, it is preferable to use the photochromic compound (or photochromic composition) in an amount of 0.001 to 10 parts by mass per 100 parts by mass of the polymerizable compound. The optimal amount varies depending on the intended use. For example, the amounts are as follows when the photochromic curable composition is used as a thin-film optical article and when it is used as a thick-film optical article.

[0188] (Use as Thin Film Optical Article) For example, when the photochromic curable composition is made into a thin film (a polymer film obtained by polymerizing the photochromic curable composition) having a thickness of 10 μm or more and less than 1000 μm, for example, about 100 μm, it is preferable to adjust the color tone by blending 0.001 to 10 parts by mass of the photochromic compound (or photochromic composition) of the above embodiment with 100 parts by mass of other polymerizable monomers.

[0189] (Use as a thick-film optical article) In the case of a thick cured body (a polymer molded body obtained by polymerizing the photochromic curable composition), for example, a cured body having a thickness of 1 mm or more, it is preferable to adjust the color tone by blending 0.001 to 1 part by mass of the photochromic compound (or photochromic composition) of the above embodiment with 100 parts by mass of the thick cured body or another polymerizable monomer that gives a thick cured body.

[0190] <Polymerizable Compound> As described above, the photochromic compound is preferably used in combination with a polymerizable compound to form a photochromic curable composition. Examples of the polymerizable compound include urethane or urea-based polymerizable compounds capable of forming a urethane bond, a urea bond, or the like, compounds having a polymerization reactive group, radical polymerizable compounds, and epoxy-based polymerizable compounds. These polymerizable compounds are not particularly limited, but for example, the polymerizable compounds described in Patent Document 10 can be suitably used.

[0191] Among these, the following polymerizable compounds are particularly preferably used.

[0192] <Compound Having a Polymerization Reactive Group> Examples of compounds having a polymerization reactive group include compounds having an iso(thio)cyanate group (iso(thio)cyanate compound). The iso(thio)cyanate compound is a compound having an isocyanate group or an isothiocyanate group, and may contain both an isocyanate group and an isothiocyanate group. This compound is preferably used in combination with a compound containing active hydrogen, which will be described later. Examples of such iso(thio)cyanate compounds include, but are not limited to, the following compounds:

[0193] (Polyiso(thio)cyanate) Polyiso(thio)cyanate is a compound having at least two iso(thio)cyanate groups in one molecule. Examples of polyiso(thio)cyanates include aromatic polyiso(thio)cyanates having an aromatic ring, such as m-xylene diisocyanate and 4,4'-diphenylmethane diisocyanate, and aliphatic polyiso(thio)cyanates, such as norbornane diisocyanate and dicyclohexylmethane-4,4'-diisocyanate.

[0194] (Compound Having Active Hydrogen) The compound having active hydrogen is not limited thereto, but is preferably a compound having a hydroxyl group and / or a thiol group, and particularly preferably a polyfunctional compound having two or more active hydrogens in one molecule. Specific examples of the compound having active hydrogen include polyfunctional thiol compounds such as pentaerythritol tetrakis(3-mercaptopropionate) and 4-mercaptomethyl-3,6-dithia-octanedithiol; and polyfunctional alcohols such as trimethylolpropane and pentaerythritol.

[0195] (Radical Polymerizable Compound) The radical polymerizable compound includes a polyfunctional radical polymerizable compound and a monofunctional radical polymerizable compound. These can be used alone or in combination. The radical polymerizable substituent includes a group having an unsaturated double bond, i.e., a vinyl group (including a styryl group, a (meth)acrylic group, an allyl group, etc.).

[0196] The polyfunctional radical polymerizable compound is a compound having two or more radical polymerizable substituents in the molecule, and includes a first polyfunctional radical polymerizable compound having 2 to 10 radical polymerizable substituents and a second polyfunctional radical polymerizable compound having more than 10 radical polymerizable substituents.

[0197] The first polyfunctional radically polymerizable compound is not particularly limited, but it is more preferable that the number of radically polymerizable substituents is 2 to 6. Specific examples thereof are as follows:

[0198] (Polyfunctional (meth)acrylic acid ester compounds) 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.

[0199] (Polyfunctional allyl compounds) Diallyl phthalate, diallyl terephthalate, diallyl isophthalate, diallyl tartrate, diallyl epoxysuccinate, diallyl fumarate, diallyl chlorendate, diallyl hexaphthalate, diallyl carbonate, allyl diglycol carbonate, trimethylolpropane triallyl carbonate.

[0200] (Polyfunctional thio(meth)acrylic acid ester compounds) 1,2-bis(methacryloylthio)ethane, bis(2-acryloylthioethyl)ether, 1,4-bis(methacryloylthiomethyl)benzene.

[0201] (Radical Polymerizable Compound) Examples of the second polyfunctional radically polymerizable compound having more than 10 radically polymerizable substituents include compounds with relatively large molecular weights, such as silsesquioxane compounds having radically polymerizable substituents and polyrotaxane compounds having radically polymerizable substituents.

[0202] Furthermore, the monofunctional radically polymerizable compound is a compound having one radically polymerizable substituent in the molecule, and specific examples thereof include, but are not limited to, the following compounds.

[0203] (Unsaturated carboxylic acids) acrylic acid, methacrylic acid, maleic anhydride.

[0204] ((Meth)acrylic acid esters) Methyl (meth)acrylate, benzyl methacrylate, phenyl methacrylate.

[0205] (Monofunctional (meth)acrylic acid ester compounds) 2-hydroxyethyl methacrylate, glycidyl (meth)acrylate, β-methylglycidyl (meth)acrylate, bisphenol A monoglycidyl ether methacrylate, 4-glycidyloxy methacrylate, 3-(glycidyl-2-oxyethoxy)-2-hydroxypropyl methacrylate, 3-(glycidyloxy-1-isopropyloxy)-2-hydroxypropyl acrylate, 3-glycidyloxy-2-hydroxypropyloxy)-2-hydroxypropyl acrylate.

[0206] (Fumaric acid esters) Diethyl fumarate, diphenyl fumarate.

[0207] (Thio(meth)acrylic acid) methyl thioacrylate, benzyl thioacrylate, benzyl thiomethacrylate.

[0208] (Vinyl Compounds) Divinylbenzene, styrene, chlorostyrene, methylstyrene, vinylnaphthalene, α-methylstyrene dimer, bromostyrene.

[0209] The radical polymerizable compounds can be used alone or in combination. In this case, the amount of the polyfunctional radical polymerizable compound is preferably 80 to 100 parts by mass and the amount of the monofunctional radical polymerizable compound is preferably 0 to 20 parts by mass, and more preferably 90 to 100 parts by mass of the polyfunctional radical polymerizable compound and 0 to 10 parts by mass of the monofunctional radical polymerizable compound, per 100 parts by mass of the total of the radical polymerizable compounds. Furthermore, the amount of the first polyfunctional radical polymerizable compound is preferably 80 to 100 parts by mass, the amount of the second polyfunctional radical polymerizable compound is 0 to 20 parts by mass, and the amount of the monofunctional radical polymerizable compound is preferably 0 to 20 parts by mass, and more preferably 85 to 100 parts by mass of the first polyfunctional radical polymerizable compound, the amount of the second polyfunctional radical polymerizable compound is 0 to 10 parts by mass, and the amount of the monofunctional radical polymerizable compound is 0 to 10 parts by mass, per 100 parts by mass of the total of the radical polymerizable compounds.

[0210] (Various Compounding Agents) Various known compounding agents can be compounded into the curable composition as long as the effects are not impaired. Examples of compounding agents include various stabilizers such as release agents, ultraviolet absorbers, infrared absorbers, ultraviolet stabilizers, antioxidants, coloring inhibitors, antistatic agents, fluorescent dyes, dyes, pigments, and fragrances. Solvents and leveling agents can also be compounded. Thiols such as t-dodecyl mercaptan can also be compounded as polymerization regulators.

[0211] Among the above-mentioned compounding ingredients, ultraviolet stabilizers are preferred because they can improve the durability of the photochromic moiety. Known examples of such ultraviolet stabilizers include hindered amine light stabilizers, hindered phenol antioxidants, and sulfur-based antioxidants. Particularly preferred ultraviolet stabilizers are as follows:

[0212] Bis(1,2,2,6,6-pentamethyl-4-piperidyl) sebacate, Adeka STAB LA-52, LA-57, LA-62, LA-63, LA-67, LA-77, LA-82, LA-87 manufactured by ADEKA Corporation, 2,6-di-tert-butyl-4-methyl-phenol, ethylene bis(oxyethylene) bis[3-(5-tert-butyl-4-hydroxy-m-tolyl)propionate], IRGANOX 1010, 1035, 1075, 1098, 1135, 1141, 1222, 1330, 1425, 1520, 259, 3114, 3790, 5057, 565 manufactured by BASF Japan Ltd. The amount of such an ultraviolet stabilizer used is not particularly limited as long as the effect is not impaired, but is usually in the range of 0.001 to 10 parts by mass, particularly 0.01 to 1 part by mass, per 100 parts by mass of the photochromic curable composition.

[0213] In addition to the ultraviolet stabilizer, an ultraviolet absorber can also be used. Known ultraviolet absorbers such as benzophenone-based compounds, benzotriazole-based compounds, cyanoacrylate-based compounds, triazine-based compounds, and benzoate-based compounds can be used as the ultraviolet absorber, with cyanoacrylate-based compounds and benzophenone-based compounds being particularly preferred. The ultraviolet stabilizer is preferably used in an amount of 0.001 to 5 parts by mass relative to 100 parts by mass of the photochromic curable composition containing the photochromic compound and the polymerizable compound.

[0214] <Method of using photochromic curable composition; optical article> A photochromic cured product is obtained by curing the photochromic curable composition. Polymerization and curing for producing the photochromic cured product is carried out by radical polymerization, ring-opening polymerization, anionic polymerization, or condensation polymerization using irradiation with active energy rays such as ultraviolet rays, α-rays, β-rays, or γ-rays, heat, or a combination of both. That is, an appropriate polymerization method may be adopted depending on the types of polymerizable compound and polymerization and curing accelerator and the form of the photochromic cured product to be formed.

[0215] When a curable composition containing a polymerizable compound is thermally polymerized, the temperature affects the properties of the resulting photochromic cured product.

[0216] The temperature conditions cannot be unconditionally limited because they are affected by the type and amount of the thermal polymerization initiator and the type of polymerizable compound, but a generally preferred method is to start the polymerization at a relatively low temperature and slowly increase the temperature. Like the temperature, the polymerization time also varies depending on various factors, so it is preferable to determine the optimal time in advance based on these conditions. Generally, however, it is preferable to select conditions so that the polymerization is completed within 2 to 48 hours. When obtaining a photochromic laminate sheet, it is preferable to carry out the polymerization at a temperature at which the reaction between polymerizable functional groups proceeds, and to determine the optimal temperature and time to achieve the desired molecular weight.

[0217] Furthermore, when photopolymerizing a curable composition, among the polymerization conditions, UV intensity in particular affects the properties of the resulting photochromic cured product. The illuminance conditions cannot be generally limited because they are affected by the type and amount of the photopolymerization initiator and the type of polymerizable monomer, but generally range from 50 to 500 mW / cm at a wavelength of 365 nm. ２ It is preferable to select the conditions so that the UV light is irradiated for 0.5 to 5 minutes.

[0218] [Optical Articles] The photochromic compound according to the embodiment can be used in a wide range of applications as a photochromic material, and can be used as various memory materials, such as various memory materials replacing silver halide photosensitive materials, copying materials, printing photoreceptors, memory materials for cathode ray tubes, photosensitive materials for lasers, photosensitive materials for holography, etc. The photochromic material can also be used as a photochromic lens material, optical filter material, display material, actinometer, decoration material, etc.

[0219] The photochromic compound according to the embodiment is particularly suitable for use in photochromic lenses. The photochromic lenses are suitable as lenses for spectacles such as sunglasses. Any known method can be used to manufacture the photochromic lenses, as long as it can provide uniform photochromic performance.

[0220] When photochromic properties are expressed by the kneading method, the above-mentioned curable composition is injected between glass molds held by elastomer gaskets or spacers, and depending on the types of polymerizable compound and polymerization curing accelerator, a photochromic cured product molded into the shape of an optical material such as a lens can be obtained by casting polymerization using heating in an air oven or irradiation with active energy rays such as ultraviolet rays.

[0221] When photochromic properties are expressed by a lamination method, a coating liquid is prepared by dissolving a curable composition in an appropriate organic solvent, and the coating liquid is applied to the surface of an optical substrate such as a lens substrate by spin coating, dipping, or the like, and then dried to remove the organic solvent. Subsequently, polymerization and curing are carried out by UV irradiation or heating in an inert gas such as nitrogen, thereby forming a photochromic layer made of a photochromic cured product on the surface of the optical substrate (coating method).

[0222] Alternatively, a photochromic layer made of a photochromic cured product can be formed on the surface of an optical substrate by cast polymerization using an inner mold in which an optical substrate such as a lens substrate is placed facing a glass mold so that a predetermined gap is formed, a curable composition is injected into this gap, and polymerization and curing are carried out in this state by UV irradiation, heating, etc. (cast polymerization method).

[0223] When a photochromic layer is formed on the surface of an optical substrate by the above-mentioned lamination methods (coating method and cast polymerization method), the adhesion between the photochromic layer and the optical substrate can be improved by previously subjecting the surface of the optical substrate to a chemical treatment using an alkaline solution, an acid solution, etc., or a physical treatment using corona discharge, plasma discharge, polishing, etc. Of course, it is also possible to provide a transparent adhesive resin layer on the surface of the optical substrate.

[0224] Furthermore, when photochromic properties are expressed by a binder method, a photochromic sheet is produced by sheet molding using a curable composition, and this is sandwiched between two transparent sheets (optical sheets), and the aforementioned polymerization and curing is carried out to obtain a photochromic laminate in which the photochromic layer serves as an adhesive layer.

[0225] In this case, the photochromic sheet can also be produced by coating with a coating liquid prepared by dissolving the curable composition in an organic solvent.

[0226] The photochromic laminate produced in this manner is, for example, placed in a mold, and then a thermoplastic resin (e.g., polycarbonate) for optical substrates such as lenses is injection molded to obtain optical substrates such as lenses of a predetermined shape to which photochromic properties have been imparted.

[0227] This photochromic laminate can also be adhered to the surface of an optical substrate with an adhesive or the like, thereby obtaining a photochromic lens.

[0228] When preparing a photochromic laminate as described above, it is preferable to use a urethane or urea-based polymerizable compound, particularly a urethane-based polymerizable compound, as the polymerizable compound, and adjust it so that polyurethane is formed, in order to obtain particularly high adhesion to the optical substrate.

[0229] The above-described curable composition can exhibit photochromic properties with excellent color density at high temperatures.

[0230] Furthermore, the photochromic layer or photochromic cured product formed from the curable composition can be dyed using a dye such as a disperse dye, or a hard coat film can be formed using a hard coat agent whose main component is a sol of a silane coupling agent or silicon, zirconium, antimony, aluminum, tin, tungsten, or the like, depending on the application. ２ , TiO ２ , ZrO ２ It is also possible to carry out post-processing such as forming a thin film by vapor deposition of a metal oxide such as ZnO, applying an organic polymer to form a thin film to prevent reflection, or performing antistatic treatment.

[0231] The present invention will be described in more detail by the following examples, which are merely illustrative of the present invention and are not intended to limit the scope and spirit of the present invention.

[0232] Example 1, Step 1: 200 mL of toluene was added to 9.3 g (20.0 mmol) of a halogenated compound represented by the following formula (1-1), synthesized from 4,4'-dimethylbenzophenone with reference to the method described in Patent Document 11, and the mixture was heated. 50 mL of toluene was distilled off at normal pressure. After distillation, the mixture was cooled to an internal temperature of -20°C, and then 15 mL of n-BuLi (1.6 M hexane solution) was added dropwise while maintaining the temperature at -15°C or below. After confirming the consumption of raw materials, 2.6 g (30.2 mmol) of methyl propyl ketone was added dropwise while maintaining the temperature at -15°C or below. After stirring for 1 hour, the mixture was slowly warmed to room temperature. 150 mL of water was added, and the mixture was separated. Water washing was repeated until the pH of the aqueous layer reached 7. The resulting organic layer was concentrated and then purified by silica gel chromatography to obtain the compound represented by the following formula (1-2) in an 87% yield.

[0233]

[0234]

[0235] Step 2: 7.12 g (17.4 mmol) of the compound represented by formula (1-2) was dissolved in 75 mL of tetrahydrofuran, and 1.4 g of 5% Pd / C (50% water content) was added, followed by a reaction with hydrogen gas under pressure of 0.05 to 0.1 MPa. After confirming the consumption of the raw materials, the Pd / C was filtered off, and the solvent in the resulting organic layer was removed to obtain the compound represented by formula (1-3) below in a 100% yield.

[0236]

[0237] Step 3: 100 mL of toluene was added to 5.0 g (26.1 mmol) of p-toluenesulfonic acid monohydrate, and azeotropic dehydration was performed until the water content in the toluene reached 92 ppm. After azeotropic dehydration, 5.8 g of the compound represented by formula (1-3) was added, and the mixture was heated at 100°C. After the raw materials were consumed, the mixture was cooled to room temperature, 48 g of a 5% aqueous solution of sodium bicarbonate was added, and the mixture was stirred and separated. 100 mL of water was added, and the mixture was separated. Washing with water was repeated until the pH of the aqueous layer reached 7, and the resulting organic layer was concentrated and purified by silica gel chromatography to obtain the compound represented by formula (1-4) in an 82% yield.

[0238]

[0239] Step 4: 3.2 g (10.0 mmol) of the compound represented by formula (1-4) and 3.0 g (12.0 mmol) of the propargyl alcohol represented by the following formula (1-5) were dissolved in 80 mL of toluene, and 0.25 g (1.0 mmol) of pyridinium p-toluenesulfonate was added and stirred at 85°C for 1 hour. After the compound represented by formula (1-4) was consumed, the mixture was cooled to room temperature, and 80 mL of water was added and the layers were separated. The solvent in the resulting organic layer was removed, and the residue was purified by chromatography on silica gel and recrystallized from an ethanol / acetonitrile mixed solvent to obtain a photochromic compound represented by the following formula (1-6) in a yield of 67%.

[0240]

[0241]

[0242] The elemental analysis results of the photochromic compound represented by formula (1-5) were C: 87.24% and H: 6.95%. ４０ H ３８ O ２ The results were in good agreement with the calculated values ​​of C: 87.23% and H: 6.95%.

[0243] Furthermore, when the proton nuclear magnetic resonance spectrum was measured, it showed 19H peaks due to propyl groups and methyl groups around δ0.0 to 3.5 ppm, 3H peaks due to methoxy groups around δ3.5 to 5.0 ppm, and 16H peaks due to aromatic protons and alkene protons around δ5.0 to 9.0 ppm.

[0244] moreover １３ Measurement of the C-nuclear magnetic resonance spectrum showed a peak due to aromatic ring carbon at around δ 110 to 160 ppm, a peak due to alkene carbon at around δ 80 to 140 ppm, and a peak due to alkyl carbon at δ 20 to 60 ppm.

[0245] Example 2 The reaction was carried out in the same manner as in Example 1, except that in the first step, 3-methyl-4-methoxybenzophenone was used instead of 4,4′-dimethylbenzophenone, and 3-heptanone was used instead of methyl propyl ketone, and in the fifth step, the compound represented by the following formula (2-1) was used instead of the compound represented by the formula (1-5), to obtain a photochromic compound represented by the following formula (2-2) in a yield of 71%.

[0246]

[0247]

[0248] The elemental analysis results of the photochromic compound represented by formula (2-2) were C: 82.70% and H: 7.25%. ４４ H ４６ O ４ The results were in good agreement with the calculated values ​​of C: 82.72% and H: 7.26%.

[0249] Furthermore, when the proton nuclear magnetic resonance spectrum was measured, it showed 22H peaks due to methyl groups, ethyl groups, butyl groups, and propoxy groups around δ0.0 to 3.5 ppm, 8H peaks due to methoxy groups and propoxy groups around δ3.5 to 5.0 ppm, and 16H peaks due to aromatic protons and alkene protons around δ5.0 to 9.0 ppm.

[0250] moreover １３ Measurement of the C-nuclear magnetic resonance spectrum showed a peak due to aromatic ring carbon at around δ 110 to 160 ppm, a peak due to alkene carbon at around δ 80 to 140 ppm, and a peak due to alkyl carbon at δ 20 to 60 ppm.

[0251] Example 3 The reaction was carried out in the same manner as in Example 1, except that in the first step, 4,4'-dimethoxybenzophenone was used instead of 4,4'-dimethylbenzophenone, 4-methyl-3-hexanone was used instead of methyl propyl ketone, and in the fifth step, the compound represented by the following formula (3-1) was used instead of the compound represented by the formula (1-5), to obtain a photochromic compound represented by the following formula (3-2) in a yield of 43%.

[0252]

[0253]

[0254] The elemental analysis results of the photochromic compound represented by formula (3-2) were C: 79.28%, H: 6.95%, and N: 2.05%. ４５ H ４７ NO ５ The results were in good agreement with the calculated values ​​of C: 79.27%, H: 6.95%, and N: 2.05%.

[0255] Furthermore, when the proton nuclear magnetic resonance spectrum was measured, 18H peaks due to ethyl groups, 2-butyl groups, and morpholino groups were observed around δ0.0 to 3.5 ppm, 13H peaks due to methoxy groups and morpholino groups were observed around δ3.5 to 5.0 ppm, and 16H peaks due to aromatic protons and alkene protons were observed around δ5.0 to 9.0 ppm.

[0256] moreover １３ Measurement of the C-nuclear magnetic resonance spectrum showed a peak due to aromatic ring carbon at around δ 110 to 160 ppm, a peak due to alkene carbon at around δ 80 to 140 ppm, and a peak due to alkyl carbon at δ 20 to 60 ppm.

[0257] Example 4 First Step With reference to the method described in Patent Document 11, 9.3 g (20.0 mmol) of a carboxylic acid represented by the following formula (4-1) was synthesized from 3-bromo-4-methoxybenzophenone, and with reference to the method described in Patent Document 8, the carboxylic acid compound represented by the following formula (4-2) was obtained in a yield of 92% by reacting the carboxylic acid with 2,6-dimethylbenzenethiol.

[0258]

[0259]

[0260] Step 2 In Step 1 of Example 1, a naphthol compound represented by the following formula (4-4) was synthesized in the same manner as in Step 1 of Example 1, except that, instead of the compound represented by formula (1-1), an iodine compound represented by the following formula (4-3) synthesized from a carboxylic acid compound represented by formula (4-2) was used with reference to the method described in Patent Document 11, and ethyl propyl ketone was used instead of methyl propyl ketone.

[0261]

[0262]

[0263] Step 3: The reaction was carried out in the same manner as in Step 4 of Example 1, except that the compound represented by formula (4-4) was used instead of the compound represented by formula (1-4) and the compound represented by formula (3-1) was used instead of the compound represented by formula (1-5), to obtain a photochromic compound represented by the following formula (4-5) in a yield of 60%.

[0264]

[0265] The elemental analysis results of the photochromic compound represented by formula (4-5) were C: 79.14%, H: 6.65%, N: 1.80%, and S: 4.14%. ５１ H５１ NO ４ The calculated values ​​of S were C: 79.14%, H: 6.64%, N: 1.81%, and S: 4.14%, which were in good agreement.

[0266] Furthermore, when the proton nuclear magnetic resonance spectrum was measured, 22H peaks due to methyl groups, ethyl groups, propyl groups, and morpholino groups were observed around δ0.0 to 3.5 ppm, 10H peaks due to methoxy groups and morpholino groups were observed around δ3.5 to 5.0 ppm, and 19H peaks due to aromatic protons and alkene protons were observed around δ5.0 to 9.0 ppm.

[0267] moreover １３ Measurement of the C-nuclear magnetic resonance spectrum showed a peak due to aromatic ring carbon at around δ 110 to 160 ppm, a peak due to alkene carbon at around δ 80 to 140 ppm, and a peak due to alkyl carbon at δ 20 to 60 ppm.

[0268] Example 5 Step 1 The reaction was carried out in the same manner as in Step 1 of Example 4, except that 4-bromo-3',4'-dimethoxybenzophenone was used instead of 4,4'-dimethylbenzophenone, to obtain a carboxylic acid compound represented by the following formula (5-1).

[0269]

[0270] Step 2: 7.4 g (54.3 mmol) of 4-methylphenylboronic 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 to 24.6 g (49.9 mmol) of the carboxylic acid compound represented by formula (5-1), and the mixture was stirred while bubbling with nitrogen. After continuing bubbling with nitrogen for about 20 minutes, Pd(PPh ３ ) ４142.7 mg (0.1 mmol) of toluene was added and the mixture was reacted at 75°C for 2 hours. After the reaction, the mixture was cooled to room temperature, 650 mL of THF was added, the mixture was cooled to 0-5°C, concentrated hydrochloric acid was added until the pH reached 1, and the layers were separated. The mixture was washed twice with 500 mL of water to remove the solvent. Purification was carried out by reslurrying in 300 mL of methanol, and a carboxylic acid represented by the following formula (5-2) was obtained in a yield of 93%.

[0271]

[0272] Third Step: With reference to the method described in Patent Document 11, an iodine compound represented by the following formula (5-3) was obtained from the compound represented by formula (5-2) in a yield of 76%.

[0273]

[0274] Step 4: The reaction was carried out in the same manner as in Step 1 of Example 1, except that the compound represented by formula (5-3) was used instead of the compound represented by formula (1-1) and methyl butyl ketone was used instead of methyl propyl ketone, to synthesize a naphthol compound represented by the following formula (5-4).

[0275]

[0276] Step 5: The reaction was carried out in the same manner as in Step 4 of Example 1, except that the compound represented by formula (5-4) was used instead of the compound represented by formula (1-4) and the compound represented by formula (5-5) below was used instead of the compound represented by formula (1-5), to obtain a photochromic compound represented by formula (5-6) below in a yield of 63%.

[0277]

[0278]

[0279] The elemental analysis results of the photochromic compound represented by formula (5-6) were C: 82.04% and H: 6.59%. ４８ H ４６ O ５ The results were in good agreement with the calculated values ​​of C: 82.02% and H: 6.60%.

[0280] Furthermore, when the proton nuclear magnetic resonance spectrum was measured, it showed 15H peaks due to methyl groups and butyl groups around δ 0.0 to 3.5 ppm, 12H peaks due to methoxy groups around δ 3.5 to 5.0 ppm, and 19H peaks due to aromatic protons and alkene protons around δ 5.0 to 9.0 ppm.

[0281] moreover １３ Measurement of the C-nuclear magnetic resonance spectrum showed a peak due to aromatic ring carbon at around δ 110 to 160 ppm, a peak due to alkene carbon at around δ 80 to 140 ppm, and a peak due to alkyl carbon at δ 20 to 60 ppm.

[0282] Example 6 First Step: 6.9 g (15.0 mmol) of the carboxylic acid represented by formula (4-1), 1.6 g (18.0 mmol) of morpholine, 140 mL of toluene, and 5.0 g (45.0 mmol) of potassium tert-butoxide were added, and the mixture was stirred under reduced pressure to remove dissolved oxygen. ２ 13.7 mg (0.015 mmol) of (dba)3 and 28.6 mg (0.06 mmol) of X-phos were added and heated to 85°C. Heating was continued until the raw materials were consumed. After the reaction was completed, the mixture was cooled to room temperature and then filtered. 150 mL of tetrahydrofuran and 10% hydrochloric acid were added to the obtained filtrate, neutralized, and then the layers were separated. The obtained organic layer was concentrated and purified by reslurrying in 70 mL of 2-propanol, yielding the carboxylic acid represented by the following formula (6-1) in a yield of 92%.

[0283]

[0284] Step 2: The reaction was carried out in the same manner as in Example 5, except that in Step 3, the compound represented by formula (6-1) was used instead of the compound represented by formula (5-2), and in Step 4, 4-octanone was used instead of methyl butyl ketone, to obtain a photochromic compound represented by the following formula (6-2) in a yield of 61%.

[0285]

[0286] The elemental analysis results of the photochromic compound represented by formula (6-2) were C: 79.40%, H: 7.10%, and N: 2.00%. ４６ H ４９ NO ５ The results were in good agreement with the calculated values ​​of C: 79.39%, H: 7.10%, and N: 2.01%.

[0287] Furthermore, when the proton nuclear magnetic resonance spectrum was measured, 20H peaks due to propyl groups, butyl groups, and morpholino groups were observed around δ0.0 to 3.5 ppm, 13H peaks due to methoxy groups and morpholino groups were observed around δ3.5 to 5.0 ppm, and 16H peaks due to aromatic protons and alkene protons were observed around δ5.0 to 9.0 ppm.

[0288] moreover １３ Measurement of the C-nuclear magnetic resonance spectrum showed a peak due to aromatic ring carbon at around δ 110 to 160 ppm, a peak due to alkene carbon at around δ 80 to 140 ppm, and a peak due to alkyl carbon at δ 20 to 60 ppm.

[0289] Example 7 Step 1: 2.75 g (10.0 mmol) of 4-bromo-4'-methylbenzophenone, 1.50 g (14.0 mmol) of N-methylaniline, and 0.29 g (30.0 mol) of sodium tert-butoxide were added to 50 mL of toluene, and nitrogen bubbling was performed for 20 minutes. 46 mg (0.05 mmol) of tris(dibenzylideneacetone)dipalladium(0) and 95 mg (0.20 mmol) of 2-dicyclohexylphosphino-triisopropylbiphenyl were added thereto, and the mixture was reacted at 80°C for 3 hours. After the reaction was completed, the mixture was cooled to room temperature, and then 30 mL of THF was added and filtered. The mixture was cooled to 0-5°C, and 10% hydrochloric acid was added until the pH reached 6-7. The mixture was separated and washed three times with 100 mL of water. The solvent in the resulting organic layer was removed, and the residue was purified by chromatography on silica gel to obtain benzophenone represented by the following formula (7-1) in a yield of 92%.

[0290]

[0291] Second Step: The reaction was carried out with reference to the method described in Patent Document 12, to obtain propargyl alcohol represented by the following formula (7-2) in a yield of 86%.

[0292]

[0293] Step 3: The naphthol compound represented by the following formula (7-3) was synthesized in the same manner as in Step 1 of Example 1, except that 4-methoxybenzophenone was used instead of 4,4'-dimethylbenzophenone and 2-octanone was used instead of methyl propyl ketone. 2.5 g (6.7 mmol) of the obtained naphthol compound, 5.0 g of Wakogel C300, and 80 mL of toluene were added and heated to 100°C. 2.85 g (8.7 mmmol) of propargyl alcohol represented by formula (7-2) dissolved in 20 mL of toluene was added thereto and heated at 100°C. After the raw naphthol derivative was consumed, the mixture was cooled to room temperature and filtered. The solvent in the resulting organic layer was removed, and the resulting product was purified by chromatography on silica gel and recrystallized from an ethanol / acetonitrile mixed solvent to obtain the photochromic compound represented by the following formula (7-4) in a 58% yield.

[0294]

[0295]

[0296] The elemental analysis results of the photochromic compound represented by formula (7-4) were C: 86.05%, H: 7.21%, and N: 2.06%. ４９ H ４９ NO ２ The results were in good agreement with the calculated values ​​of C: 86.05%, H: 7.22%, and N: 2.05%.

[0297] Furthermore, when the proton nuclear magnetic resonance spectrum was measured, 24H peaks due to methyl groups, ethyl groups, and hexyl groups were observed around δ0.0 to 3.5 ppm, a 3H peak due to methoxy groups was observed around δ3.5 to 5.0 ppm, and a 22H peak due to aromatic protons and alkene protons was observed around δ5.0 to 9.0 ppm.

[0298] moreover １３Measurement of the C-nuclear magnetic resonance spectrum showed a peak due to aromatic ring carbon at around δ 110 to 160 ppm, a peak due to alkene carbon at around δ 80 to 140 ppm, and a peak due to alkyl carbon at δ 20 to 60 ppm.

[0299] Example 8 Step 1 The reaction was carried out in the same manner as in Step 1 of Example 5, except that 4-bromo-4'-methoxybenzophenone was used instead of 4-bromo-3',4'-dimethoxybenzophenone, to obtain a carboxylic acid compound represented by the following formula (8-1).

[0300]

[0301] Step 2: The reaction was carried out in the same manner as in Step 1 of Example 7, except that the compound represented by formula (7-1) was used instead of 4-bromo-4'-methylbenzophenone and diphenylamine was used instead of N-methylaniline, to synthesize the carboxylic acid represented by the following formula (8-2) in a yield of 91%.

[0302]

[0303] Third Step: The reaction was carried out in the same manner as in Example 5, except that in Step 3, the compound represented by formula (7-2) was used instead of the compound represented by formula (5-2), and in Step 4, 4-nonanone was used instead of methyl butyl ketone, to obtain a photochromic compound represented by the following formula (7-3) in a yield of 57%.

[0304]

[0305] The elemental analysis results of the photochromic compound represented by formula (8-3) were C: 83.42%, H: 6.76%, and N: 1.78%. ５５ H ５３ NO ４ The results were in good agreement with the calculated values ​​of C: 83.41%, H: 6.74%, and N: 1.77%.

[0306] Furthermore, when the proton nuclear magnetic resonance spectrum was measured, it showed 18H peaks due to propyl groups and pentyl groups around δ0.0 to 3.5 ppm, 9H peaks due to methoxy groups around δ3.5 to 5.0 ppm, and 26H peaks due to aromatic protons and alkene protons around δ5.0 to 9.0 ppm.

[0307] moreover １３ Measurement of the C-nuclear magnetic resonance spectrum showed a peak due to aromatic ring carbon at around δ 110 to 160 ppm, a peak due to alkene carbon at around δ 80 to 140 ppm, and a peak due to alkyl carbon at δ 20 to 60 ppm.

[0308] Example 9 The reaction was carried out in the same manner as in Example 6, except that N-methylaniline was used instead of morpholine in the first step and methyl ethyl ketone was used instead of 4-octanone in the second step, to obtain a photochromic compound represented by the following formula (9-1) in a yield of 66%.

[0309]

[0310] The elemental analysis results of the photochromic compound represented by formula (9-1) were C: 81.92%, H: 6.26%, and N: 2.11%. ４５ H ５１ NO ４ The results were in good agreement with the calculated values ​​of C: 81.91%, H: 6.26%, and N: 2.12%.

[0311] Furthermore, when the proton nuclear magnetic resonance spectrum was measured, it showed 11H peaks due to methyl groups and ethyl groups around δ 0.0 to 3.5 ppm, 9H peaks due to methoxy groups around δ 3.5 to 5.0 ppm, and 21H peaks due to aromatic protons and alkene protons around δ 5.0 to 9.0 ppm.

[0312] moreover １３ Measurement of the C-nuclear magnetic resonance spectrum showed a peak due to aromatic ring carbon at around δ 110 to 160 ppm, a peak due to alkene carbon at around δ 80 to 140 ppm, and a peak due to alkyl carbon at δ 20 to 60 ppm.

[0313] Example 10 The reaction was carried out in the same manner as in Example 5, except that in the first step, 3-bromo-4-methoxy-4'-methylbenzophenone was used instead of 4-bromo-3',4'-dimethoxybenzophenone, in the second step, 4-morpholinophenylboronic acid was used instead of 4-methylphenylboronic acid, in the fourth step, 4-octanone was used instead of methyl butyl ketone, and in the fifth step, the compound represented by formula (3-1) was used instead of the compound represented by formula (5-5), to obtain a photochromic compound represented by the following formula (10-1) in a yield of 56%.

[0314]

[0315] The elemental analysis results of the photochromic compound represented by formula (10-1) were C: 79.99%, H: 7.17%, and N: 3.34%. ５６ H ６０ N ２ O ５ The results were in good agreement with the calculated values ​​of C: 79.97%, H: 7.19%, and N: 3.33%.

[0316] Furthermore, when the proton nuclear magnetic resonance spectrum was measured, 27H peaks due to methyl groups, propyl groups, butyl groups, and morpholino groups were observed around δ0.0 to 3.5 ppm, 14H peaks due to methoxy groups and morpholino groups were observed around δ3.5 to 5.0 ppm, and 19H peaks due to aromatic protons and alkene protons were observed around δ5.0 to 9.0 ppm.

[0317] moreover １３ Measurement of the C-nuclear magnetic resonance spectrum showed a peak due to aromatic ring carbon at around δ 110 to 160 ppm, a peak due to alkene carbon at around δ 80 to 140 ppm, and a peak due to alkyl carbon at δ 20 to 60 ppm.

[0318] Example 11 The reaction was carried out in the same manner as in Example 10, except that 3-bromo-4-methoxy-4'-bromobenzophenone was used instead of 3-bromo-4-methoxy-4'-methylbenzophenone, an excess amount of 4-isopropoxyphenylboronic acid was used instead of 4-morpholinophenylboronic acid, 3-nonanone was used instead of 4-octanone, and the compound represented by formula (2-1) was used instead of the compound represented by formula (3-1), to obtain a photochromic compound represented by the following formula (11-1) in a yield of 54%.

[0319]

[0320] The elemental analysis results of the photochromic compound represented by formula (11-1) were C: 82.16%, H: 7.43%, and N: 3.34%. ５６ H ６０ N ２ O ５ The results were in good agreement with the calculated values ​​of C: 82.14% and H: 7.44%.

[0321] Furthermore, when the proton nuclear magnetic resonance spectrum was measured, 35H peaks due to ethyl groups, hexyl groups, isopropoxy groups, and propoxy groups were observed around δ0.0 to 3.5 ppm, 10H peaks due to methoxy groups, isopropoxy groups, and propoxy groups were observed around δ3.5 to 5.0 ppm, and 23H peaks due to aromatic protons and alkene protons were observed around δ5.0 to 9.0 ppm.

[0322] moreover １３ Measurement of the C-nuclear magnetic resonance spectrum showed a peak due to aromatic ring carbon at around δ 110 to 160 ppm, a peak due to alkene carbon at around δ 80 to 140 ppm, and a peak due to alkyl carbon at δ 20 to 60 ppm.

[0323] Example 12 Step 1 The reaction was carried out in the same manner as in Step 1 of Example 7, except that 4-bromo-4'-methoxybenzophenone was used instead of 4-bromo-4'-methylbenzophenone and diphenylamine was used instead of N-methylaniline, to synthesize propargyl alcohol represented by the following formula (12-1).

[0324]

[0325] Second Step: The reaction was carried out in the same manner as in Example 10, except that 3-bromo-4,4'-dimethylbenzophenone was used instead of 3-bromo-4-methoxy-4'-methylbenzophenone, 4-methoxyphenylboronic acid was used instead of 4-morpholinophenylboronic acid, ethyl propyl ketone was used instead of 4-octanone, and the compound represented by formula (12-1) was used instead of the compound represented by formula (3-1), to obtain a photochromic compound represented by the following formula (12-2) in a yield of 62%.

[0326]

[0327] The elemental analysis results of the photochromic compound represented by formula (12-2) were C: 86.01%, H: 6.46%, and N: 1.71%. ５８ H ５１ NO ３ The results were in good agreement with the calculated values ​​of C: 85.99%, H: 6.48%, and N: 1.70%.

[0328] Furthermore, when the proton nuclear magnetic resonance spectrum was measured, 18H peaks due to methyl groups, ethyl groups, and propyl groups were observed around δ0.0 to 3.5 ppm, 6H peaks due to methoxy groups and morpholino groups were observed around δ3.5 to 5.0 ppm, and 29H peaks due to aromatic protons and alkene protons were observed around δ5.0 to 9.0 ppm.

[0329] moreover １３ Measurement of the C-nuclear magnetic resonance spectrum showed a peak due to aromatic ring carbon at around δ 110 to 160 ppm, a peak due to alkene carbon at around δ 80 to 140 ppm, and a peak due to alkyl carbon at δ 20 to 60 ppm.

[0330] Example 13 First Step The reaction was carried out in the same manner as in Step 1 of Example 12, except that N-methylaniline was used instead of diphenylamine, to synthesize propargyl alcohol represented by the following formula (13-1).

[0331]

[0332] Second Step: The reaction was carried out in the same manner as in Example 10, except that 3-bromo-4-methoxybenzophenone was used instead of 3-bromo-4-methoxy-4'-methylbenzophenone, 2,4-dimethoxyphenylboronic acid was used instead of 4-morpholinophenylboronic acid, methyl ethyl ketone was used instead of 4-octanone, and the compound represented by formula (13-1) was used instead of the compound represented by formula (3-1), to obtain a photochromic compound represented by the following formula (13-2) in a yield of 56%.

[0333]

[0334] The elemental analysis results of the photochromic compound represented by formula (13-2) were C: 81.56%, H: 6.17%, and N: 1.82%. ５２ H ４７ NO ５ The results were in good agreement with the calculated values ​​of C: 81.54%, H: 6.19%, and N: 1.83%.

[0335] Furthermore, when the proton nuclear magnetic resonance spectrum was measured, it showed 11H peaks due to methyl groups and ethyl groups around δ 0.0 to 3.5 ppm, 12H peaks due to methoxy groups around δ 3.5 to 5.0 ppm, and 24H peaks due to aromatic protons and alkene protons around δ 5.0 to 9.0 ppm.

[0336] moreover １３ Measurement of the C-nuclear magnetic resonance spectrum showed a peak due to aromatic ring carbon at around δ 110 to 160 ppm, a peak due to alkene carbon at around δ 80 to 140 ppm, and a peak due to alkyl carbon at δ 20 to 60 ppm.

[0337] Example 14 The reaction was carried out in the same manner as in Example 6, except that ethyl propyl ketone was used instead of 4-octanone in the second step, to obtain a photochromic compound represented by the following formula (14-1) in a yield of 64%.

[0338]

[0339] The elemental analysis results of the photochromic compound represented by formula (14-1) were C: 79.12%, H: 6.77%, and N: 2.11%. ４４ H ４５ NO ５ The results were in good agreement with the calculated values ​​of C: 79.13%, H: 6.79%, and N: 2.10%.

[0340] Furthermore, when the proton nuclear magnetic resonance spectrum was measured, 16H peaks due to ethyl groups, propyl groups, and morpholino groups were observed around δ0.0 to 3.5 ppm, 13H peaks due to methoxy groups and morpholino groups were observed around δ3.5 to 5.0 ppm, and 16H peaks due to aromatic protons and alkene protons were observed around δ5.0 to 9.0 ppm.

[0341] moreover １３ Measurement of the C-nuclear magnetic resonance spectrum showed a peak due to aromatic ring carbon at around δ 110 to 160 ppm, a peak due to alkene carbon at around δ 80 to 140 ppm, and a peak due to alkyl carbon at δ 20 to 60 ppm.

[0342] Example 15 The reaction was carried out in the same manner as in Example 1, except that in the first step, 4,4'-dimethylbenzophenone was replaced with 4-methoxy-4'-trifluoromethoxybenzophenone, and 3-octanone was replaced with methyl propyl ketone, and in the fourth step, the compound represented by formula (5-5) was replaced with the compound represented by formula (1-5), to obtain a photochromic compound represented by the following formula (15-1) in a yield of 65%.

[0343]

[0344] The elemental analysis results of the photochromic compound represented by formula (15-1) were C: 74.31% and H: 5.93%. ４３ H ４１ F ３ O ５ The results were in good agreement with the calculated values ​​of C: 74.33% and H: 5.95%.

[0345] Furthermore, when the proton nuclear magnetic resonance spectrum was measured, it showed 16H peaks due to ethyl groups and pentyl groups around δ0.0 to 3.5 ppm, a 9H peak due to methoxy groups around δ3.5 to 5.0 ppm, and 16H peaks due to aromatic protons and alkene protons around δ5.0 to 9.0 ppm.

[0346] moreover １３ Measurement of the C-nuclear magnetic resonance spectrum showed a peak due to aromatic ring carbon at around δ 110 to 160 ppm, a peak due to alkene carbon at around δ 80 to 140 ppm, and a peak due to alkyl carbon at δ 20 to 60 ppm.

[0347] Example 16 The reaction was carried out in the same manner as in Example 6, except that 1,2,3,4-tetrahydroquinoline was used instead of morpholine in the first step, 5-decanone was used instead of 4-octanone in the second step, and the compound represented by formula (2-1) was used instead of the compound represented by formula (1-5), to obtain a photochromic compound represented by the following formula (16-1) in a yield of 61%.

[0348]

[0349] The elemental analysis results of the photochromic compound represented by formula (16-1) were C: 82.79%, H: 7.44%, and N: 1.76%. ５５ H ５９ NO ４ The results were in good agreement with the calculated values ​​of C: 82.77%, H: 7.45%, and N: 1.76%.

[0350] Furthermore, when the proton nuclear magnetic resonance spectrum was measured, it showed 31H peaks due to butyl groups, pentyl groups, propoxy groups, and 1,2,3,4-tetrahydroquinoline ring groups around δ0.0 to 3.5 ppm, 8H peaks due to methoxy groups and propoxy groups around δ3.5 to 5.0 ppm, and 20H peaks due to aromatic protons and alkene protons around δ5.0 to 9.0 ppm.

[0351] moreover １３Measurement of the C-nuclear magnetic resonance spectrum showed a peak due to aromatic ring carbon at around δ 110 to 160 ppm, a peak due to alkene carbon at around δ 80 to 140 ppm, and a peak due to alkyl carbon at δ 20 to 60 ppm.

[0352] Example 17 First Step: Referring to the method described in Patent Document 8, 3-bromoanisole was reacted with 4'-(1,1-dimethylethyl)[1,1'-biphenyl]-4-carbonyl chloride to obtain benzophenone represented by the following formula (17-1) in a yield of 88%.

[0353]

[0354] Second Step: The reaction was carried out in the same manner as in Example 6, except that benzophenone represented by formula (17-1) was used instead of 3-bromo-4-methoxybenzophenone, piperidine was used instead of morpholine, and 3-heptanone was used instead of 4-octanone, to obtain a photochromic compound represented by the following formula (17-2) in a yield of 53%.

[0355]

[0356] The elemental analysis results of the photochromic compound represented by formula (17-2) were C: 82.80%, H: 7.58%, and N: 1.72%. ５６ H ６１ NO ４ The results were in good agreement with the calculated values ​​of C: 82.82%, H: 7.57%, and N: 1.72%.

[0357] Furthermore, when the proton nuclear magnetic resonance spectrum was measured, it showed 33H peaks due to ethyl groups, butyl groups, tertiary butyl groups, and piperidino groups around δ 0.0 to 3.5 ppm, 9H peaks due to methoxy groups around δ 3.5 to 5.0 ppm, and 19H peaks due to aromatic protons and alkene protons around δ 5.0 to 9.0 ppm.

[0358] moreover １３Measurement of the C-nuclear magnetic resonance spectrum showed a peak due to aromatic ring carbon at around δ 110 to 160 ppm, a peak due to alkene carbon at around δ 80 to 140 ppm, and a peak due to alkyl carbon at δ 20 to 60 ppm.

[0359] Example 18 The reaction was carried out in the same manner as in the second step of Example 6, except that 3-nonanone was used instead of 4-octanone, to obtain a photochromic compound represented by the following formula (18-1) in a yield of 58%.

[0360]

[0361] The elemental analysis results of the photochromic compound represented by formula (18-1) were C: 79.50%, H: 7.23%, and N: 1.98%. ４７ H ５１ NO ５ The results were in good agreement with the calculated values ​​of C: 79.52%, H: 7.24%, and N: 1.97%.

[0362] Furthermore, when the proton nuclear magnetic resonance spectrum was measured, 22H peaks due to ethyl groups, hexyl groups, and morpholino groups were observed around δ0.0 to 3.5 ppm, 13H peaks due to methoxy groups and morpholino groups were observed around δ3.5 to 5.0 ppm, and 16H peaks due to aromatic protons and alkene protons were observed around δ5.0 to 9.0 ppm.

[0363] moreover １３ Measurement of the C-nuclear magnetic resonance spectrum showed a peak due to aromatic ring carbon at around δ 110 to 160 ppm, a peak due to alkene carbon at around δ 80 to 140 ppm, and a peak due to alkyl carbon at δ 20 to 60 ppm.

[0364] Example 19 The reaction was carried out in the same manner as in the second step of Example 6, except that 2-tridecanone was used instead of 4-octanone, to obtain a photochromic compound represented by the following formula (19-1) in a yield of 49%.

[0365]

[0366] The elemental analysis results of the photochromic compound represented by formula (19-1) were C: 79.99%, H: 7.74%, and N: 1.84%. ５１ H ５９ NO ５ The results were in good agreement with the calculated values ​​of C: 79.96%, H: 7.76%, and N: 1.83%.

[0367] Furthermore, when the proton nuclear magnetic resonance spectrum was measured, 30H peaks due to methyl groups, undecyl groups, and morpholino groups were observed around δ0.0 to 3.5 ppm, 13H peaks due to methoxy groups and morpholino groups were observed around δ3.5 to 5.0 ppm, and 16H peaks due to aromatic protons and alkene protons were observed around δ5.0 to 9.0 ppm.

[0368] moreover １３ Measurement of the C-nuclear magnetic resonance spectrum showed a peak due to aromatic ring carbon at around δ 110 to 160 ppm, a peak due to alkene carbon at around δ 80 to 140 ppm, and a peak due to alkyl carbon at δ 20 to 60 ppm.

[0369] Example 20 The reaction was carried out in the same manner as in Example 6, except that 3-methyl-4-octanone was used instead of 4-octanone in the second step, to obtain a photochromic compound represented by the following formula (20-1) in a yield of 51%.

[0370]

[0371] The elemental analysis results of the photochromic compound represented by formula (20-1) were C: 79.54%, H: 7.24%, and N: 1.96%. ４７ H ５１ NO ５ The results were in good agreement with the calculated values ​​of C: 79.52%, H: 7.24%, and N: 1.97%.

[0372] Furthermore, when the proton nuclear magnetic resonance spectrum was measured, 22H peaks due to 2-methylpropyl groups, butyl groups, and morpholino groups were observed around δ0.0 to 3.5 ppm, 13H peaks due to methoxy groups and morpholino groups were observed around δ3.5 to 5.0 ppm, and 16H peaks due to aromatic protons and alkene protons were observed around δ5.0 to 9.0 ppm.

[0373] moreover １３ Measurement of the C-nuclear magnetic resonance spectrum showed a peak due to aromatic ring carbon at around δ 110 to 160 ppm, a peak due to alkene carbon at around δ 80 to 140 ppm, and a peak due to alkyl carbon at δ 20 to 60 ppm.

[0374] (Evaluation of physical properties of photochromic plastic lens produced by coating method) (Example 21) (Preparation of curable composition) First, the photochromic compound obtained in Example 1 above, a photopolymerization initiator, and a polymerizable compound were mixed to obtain a curable composition.

[0375] As the polymerizable compound, a mixture of the following radical polymerizable monomers was used.

[0376] Polyethylene glycol dimethacrylate (average molecular weight 736): 42 parts by weight Polyethylene glycol dimethacrylate (average molecular weight 536): 12 parts by weight Trimethylolpropane trimethacrylate: 38 parts by weight γ-methacryloyloxypropyltrimethoxysilane: 2 parts by weight Glycidyl methacrylate: 1 part by weight

[0377] In the curable composition, the photochromic compound was added in an amount of 0.25 mmol when the total amount of the radical polymerizable monomers was 100 g.

[0378] The following additives were used:

[0379] Phenylbis(2,4,6-trimethylbenzoyl)phosphine oxide (photopolymerization initiator: Omnirad 819): 0.3 parts by mass Ethylenebis(oxyethylene)bis[3-(5-tert-butyl-4-hydroxy-m-tolyl)propionate] (stabilizer, Irganox 245): 1 part by mass Bis(1,2,2,6,6-pentamethyl-4-piperidyl)sebacate: 3 parts by mass DuPont Toray Specialty Materials Co., Ltd. leveling agent (L-7001): 0.1 parts by mass

[0380] The additives are blended in proportions based on 100 parts by mass of the total amount of radical polymerizable monomers.

[0381] (Production of Optical Article) Using this curable composition, a photochromic laminate was obtained by a lamination method through polymerization as follows.

[0382] First, a thiourethane-based plastic lens with a center thickness of 2 mm and a refractive index of 1.60 was prepared as an optical substrate. This thiourethane-based plastic lens was previously subjected to alkaline etching using a 10% aqueous solution of sodium hydroxide at 50°C for 5 minutes, and then thoroughly washed with distilled water.

[0383] Using a spin coater (1H-DX2, manufactured by MIKASA), the surface of the above plastic lens was coated with a moisture-curable primer (product name: TR-SC-P, manufactured by Tokuyama Corporation) at a rotation speed of 70 rpm for 15 seconds, followed by 1000 rpm for 10 seconds. Thereafter, approximately 2 g of the above obtained photochromic curable composition was spin coated at a rotation speed of 60 rpm for 40 seconds, followed by 600 rpm for 10 to 20 seconds, so as to form a photochromic coating layer with a thickness of 40 μm.

[0384] The lens having the photochromic curable composition (photochromic coating layer) applied to its surface was heated in a nitrogen gas atmosphere at an output of 200 mW / cm ２ The coating was cured by irradiating it with light for 90 seconds using a metal halide lamp, and then heated at 110°C for 1 hour to prepare a photochromic laminate having a photochromic layer.

[0385] Examples 22 to 40 In the same manner as in Example 21, photochromic laminates were prepared using the photochromic compounds obtained in Examples 2 to 20.

[0386] Comparative Examples 1 to 4 Photochromic laminates were obtained in the same manner as in Example 21 using photochromic compounds represented by the following formulas (A) to (D).

[0387]

[0388]

[0389]

[0390]

[0391] (Synthesis of Compound A) Compound (A) was synthesized in the same manner as in the second step of Example 6, except that acetone was used instead of 4-octanone.

[0392] (Synthesis of Compound C) A compound represented by the following formula (C-1), which was synthesized with reference to the method described in Patent Document 13, was reacted with tris(trimethylsiloxy)silylethylchlorosilane with reference to the method described in Patent Document 3 to synthesize compound (C).

[0393]

[0394] (Synthesis of Compound D) Compound (D) was synthesized by carrying out the reaction in the same manner as in the second step of Example 6, except that cyclooctanone was used instead of 4-octanone.

[0395] <Evaluation Method> The obtained photochromic laminate was evaluated by the following method. (1) Photochromic Properties [1] Maximum absorption wavelength (λmax): This is the maximum absorption wavelength after color development measured using a spectrophotometer (instant multichannel photodetector MCPD3000) manufactured by Otsuka Electronics Co., Ltd., and was used as an index of the color tone during color development. [2] Color density at 23°C (A ２３) is the difference between the absorbance {ε(240)} at the maximum absorption wavelength after 240 seconds of light irradiation at 23°C and the absorbance ε(0) without light irradiation, and is used as an index of color density. The higher this value, the better the photochromic properties. [3] 23°C fading half-life [τ1 / 2 (sec.)] is the time required for the absorbance at the maximum absorption wavelength of the sample to decrease to 1 / 2 of {ε(240) - ε(0)} when the light irradiation is stopped after 240 seconds of light irradiation at 23°C, and is used as an index of the fading speed. The shorter this time, the faster the fading speed. [4] Retention rate (A ９６ / A ０ × 100): The obtained photochromic plastic lens was subjected to accelerated deterioration for 96 hours using a Xenon Weather Meter X25 manufactured by Suga Test Instruments Co., Ltd. After that, the color density was evaluated before and after the test, and the color density before the test (A ０ ) and color density after the test (A ９６ ) and measure the ratio (A ９６ / A ０ The higher the retention rate, the higher the color durability.

[0396] The results of Examples 26, 34, 38 to 40 and Comparative Examples 1 to 4 are summarized in Table 1, and the results of Examples 21 to 25, 27 to 33, 35 to 37 are summarized in Table 2.

[0397]

[0398]

[0399] <Evaluation of physical properties of photochromic layer prepared by binder method> (Example 41) A binder sheet was prepared by the following method. The binder sheet was prepared by laminating a first optical sheet, a first adhesive layer, a photochromic layer, a second adhesive layer, and a second optical sheet in this order. Polycarbonate sheets with a thickness of 400 μm were used as the first optical sheet and the second optical sheet.

[0400] (Preparation of Photochromic Layer-Forming Composition) A 2 L four-neck flask equipped with a stirring blade, a cooling tube, a thermometer, and a nitrogen gas inlet tube was charged with 315 parts by mass of polycarbonate diol having a number average molecular weight of 1,000, 100 parts by mass of isophorone diisocyanate, and 72 parts by mass of toluene, and the mixture was allowed to react at 100°C for 7 hours under a nitrogen atmosphere to synthesize a urethane prepolymer having an isocyanate group at its terminal. After completion of the urethane prepolymer reaction, the reaction solution was cooled to around 0°C and dissolved in 205 parts by mass of tertiary butyl alcohol and 382 parts by mass of diethyl ketone, and the liquid temperature was maintained at 0°C. Next, a mixed solution of 21.3 parts by mass of bis-(4-aminocyclohexyl)methane and 20 parts by mass of diethyl ketone, which served as a chain extender, was added dropwise within 30 minutes, and the mixture was allowed to react at 0°C for 1 hour. Thereafter, 8.1 parts by mass of 1,2,2,6,6-pentamethyl-4-aminopiperidine was further added dropwise, and the mixture was allowed to react at 0° C. for 1 hour to obtain a diethyl ketone solution of a terminally unreactive urethane urea resin.

[0401] 100 parts by mass of the obtained terminally non-reactive urethane urea resin solution, 6.3 parts by mass of Example 1 (photochromic compound represented by formula (1-7), a mixture of isomers of 4,4'-methylenebis(cyclohexyl isocyanate) (polyisocyanate compound)), 0.4 parts by mass of ethylenebis(oxyethylene)bis[3-(5-tert-butyl-4-hydroxy-m-tolyl)propionate] as an antioxidant, and 0.06 parts by mass of L-7001 manufactured by DuPont-Toray Specialty Materials Co., Ltd. as a surfactant were added, and the mixture was stirred and mixed at room temperature to obtain a composition for forming a photochromic layer.

[0402] The photochromic compound was added in an amount of 0.25 mmol per 100 parts by mass of the terminally non-reactive urethane urea resin.

[0403] (Preparation of Adhesive Layer Composition) A 5 L separable flask (four necks) equipped with a stirring blade, a cooling tube, a thermometer, and a nitrogen gas inlet tube was prepared. 400 parts by mass of polycarbonate diol having a number average molecular weight of 1000, 175 parts by mass of isophorone diisocyanate, and 120 parts by mass of toluene were charged into this container and reacted for 7 hours at 110°C under a nitrogen atmosphere to synthesize a urethane prepolymer having an isocyanate group at the end. After completion of the urethane prepolymer reaction, the reaction solution was cooled to around 20°C and dissolved in 2500 parts by mass of propylene glycol-monomethyl ether, and the liquid temperature was maintained at 20°C. Next, 60 parts by mass of isophorone diamine, a chain extender, was added dropwise, and the mixture was allowed to react for 1 hour at 20°C. Thereafter, 3 parts by mass of n-butylamine was added dropwise, and the mixture was allowed to react for 1 hour at 20°C to obtain a propylene glycol-monomethyl ether solution of a terminally non-reactive urethane urea resin.

[0404] To 500 parts by mass of the obtained terminally non-reactive urethane urea resin solution, 0.2 parts by mass of L-7001 manufactured by DuPont Toray Specialty Materials Co., Ltd. was added as a surfactant, and the mixture was stirred and mixed at room temperature to obtain a composition for adhesive layer.

[0405] (Production of binder sheet) Using a coater (manufactured by Tester Sangyo Co., Ltd.), the adhesive layer composition was applied to one main surface of the first optical sheet at a coating speed of 0.5 m / min, and the resulting sheet was dried for 3 minutes at a drying temperature of 110° C., thereby obtaining a first optical sheet having a first coating film with a thickness of 5 μm. In the same manner, the adhesive layer composition was applied to one main surface of the second optical sheet, thereby obtaining a second optical sheet having a second coating film.

[0406] Next, using a coater (manufactured by Tester Sangyo Co., Ltd.), the photochromic layer-forming composition was applied to a 50 μm-thick OPP film (stretched polypropylene film) at a coating speed of 0.3 m / min and dried at a drying temperature of 100°C for 5 minutes. This resulted in a third coating film. The third coating film was then bonded to a first optical sheet so that the third coating film and the first coating film were in contact with each other. The OPP film was peeled off from this structure, and the second optical sheet was bonded to the third coating film so that the other main surface of the exposed third coating film was in contact with the second coating film. The resulting laminate was then left to stand at 40°C under vacuum for 24 hours, then heat-treated at 110°C for 60 minutes, then humidified at 60°C and 100% RH for 24 hours, and finally left to stand at 40°C under vacuum for 24 hours to obtain a binder sheet. The resulting binder sheet was evaluated in the same manner as in Example 21. The results are shown in Table 3.

[0407] Examples 42 to 53, Comparative Examples 5 and 6 Binder sheets were prepared in the same manner as in Example 41 using the photochromic compounds shown in Table 3.

[0408]

[0409] Evaluation of Physical Properties of Photochromic Cured Material Prepared by Kneading Method Example 54 Preparation of Curable Composition First, the photochromic compound obtained in Example 1, additives, and polymerizable compound were mixed to obtain a curable composition. The polymerizable compound used was a combination of the following polymerizable monomers: 1,3-bis(isocyanatomethyl)cyclohexane: 36.7 parts by mass Pentaerythritol tetrakis(3-mercaptopropionate): 39.4 parts by mass Polyoxyethylene polyoxypropylene lauryl ether (Wondersurf 140 manufactured by Aoki Oil & Fats Industries Co., Ltd.): 17.4 parts by mass 1-Decanethiol: 2.8 parts by mass RX-1 prepared by the method described in Patent Document 14: 3.8 parts by mass In the curable composition, the photochromic compound was added so that the amount was 0.106 mmol per 100 g of the total amount of polymerizable monomers.

[0410] The following additives were used: Dimethyltin dichloride: 0.05 parts by mass Irganox 245: 0.1 parts by mass 2-ethylhexyl 4-methoxycinnamate: 0.6 parts by mass

[0411] (Production of Cured Product) After thoroughly degassing the prepared curable composition, it was poured into a glass mold with a 1 mm gap, and the curable composition was polymerized by cast polymerization. The polymerization was carried out using an air oven, gradually raising the temperature from 27°C to 120°C over 18 hours. After polymerization, the cured product was removed from the glass mold, yielding a photochromic cured product with a thickness of 1 mm. The obtained photochromic cured product was evaluated in the same manner as in Example 23. The results are shown in Table 4.

[0412] (Examples 55 to 66, Comparative Examples 7 and 8) Photochromic cured products were prepared using the photochromic compounds shown in Table 4 in the same manner as in Example 50. The results are summarized in Table 4.

[0413]

[0414] <Evaluation of Solubility of Photochromic Compound> Using the photochromic compounds according to the Examples and Comparative Examples shown in Table 5, the solubility in polymerizable compounds was evaluated.

[0415] Specifically, a sample was prepared by adding a photochromic compound to a composition consisting only of a radical polymerizable compound among the curable compositions used in Example 21. The concentration of the photochromic compound was 35 μmol / g.

[0416] The test was carried out using a "Yokaikun USS-1" manufactured by Nippon Seiki Seisakusho Co., Ltd. under the following conditions: Dissolution temperature: 65-70°C, Stirring conditions: Stirring dial 5, Ultrasonic irradiation conditions: Irradiation interval 3 seconds.

[0417] The dissolution was confirmed every 15 minutes up to one hour, and the degree of dissolution was visually confirmed by transmitting light through the sample, and evaluated according to the following four-level evaluation criteria.

[0418] (Evaluation criteria) 1: No turbidity is observed even when light is transmitted through the solution, and the solution is completely dissolved. 2: Very slight turbidity is observed when light is transmitted through the solution. 3: Slight turbidity is observed when light is transmitted through the solution. 4: The solution is so turbid that it can be seen even without light being transmitted through the solution.

[0419] A shorter time required for the evaluation result to reach 1 indicates higher solubility. The evaluation results of solubility are shown in Table 5.

[0420]

[0421] Example 72, First Step: 27.4 g (211.7 mmol) of N-ethyldiisopropylamine and 360 mL of toluene were added to 36.0 g (73.0 mmol) of the carboxylic acid represented by formula (5-1), and the mixture was stirred under reduced pressure to remove dissolved oxygen. ２ 4.5 g (4.9 mmol) of (dba)3 and 5.7 g (9.8 mmol) of 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene were added, and the mixture was stirred at room temperature for 30 minutes and then heated to an internal temperature of 70°C. 25.1 g (141.1 mmol) of 3-trifluoromethylbenzenethiol was slowly added dropwise thereto, and after the dropwise addition, the mixture was heated to reflux. Heating was continued until the raw materials were consumed. After the reaction was completed, the mixture was cooled to room temperature and then 540 mL of tetrahydrofuran was added. 360 mL of water was added thereto and the mixture was separated; this process was repeated three times. The solvent from the organic layer was removed, and the residue was purified by silica gel chromatography to obtain the carboxylic acid represented by the following formula (72-1) in a 56% yield.

[0422]

[0423] Step 2: The reaction was carried out in the same manner as in Example 5, except that in Step 3, the carboxylic acid represented by formula (72-1) was used instead of the carboxylic acid represented by formula (5-2), and in Step 4, ethyl propyl ketone was used instead of methyl butyl ketone, to synthesize a naphthol compound represented by the following formula (72-2).

[0424]

[0425] Step 3: The reaction was carried out in the same manner as in Step 4 of Example 1, except that the compound represented by formula (72-2) was used instead of the compound represented by formula (1-4) and the compound represented by formula (2-1) was used instead of the compound represented by formula (1-5), to obtain a photochromic compound represented by the following formula (72-3) in a yield of 63%.

[0426]

[0427] The elemental analysis results of the photochromic compound represented by formula (72-3) were C: 73.50%, H: 5.78%, and S: 3.91%. ５０ H ４７ F ３ O ５ These were in good agreement with the calculated values ​​of C: 73.51%, H: 5.80%, and S: 3.92%. Furthermore, when the proton nuclear magnetic resonance spectrum was measured, it showed 17H peaks due to ethyl groups, propyl groups, and propyloxy groups around δ 0.0 to 3.5 ppm, 11H peaks due to methoxy groups and propyloxy groups around δ 3.5 to 5.0 ppm, and 19H peaks due to aromatic protons and alkene protons around δ 5.0 to 9.0 ppm. １３ Measurement of the C-nuclear magnetic resonance spectrum showed a peak due to aromatic ring carbon at around δ 110 to 160 ppm, a peak due to alkene carbon at around δ 80 to 140 ppm, and a peak due to alkyl carbon at δ 20 to 60 ppm.

[0428] Example 73: First Step The same reaction as in Example 8 was carried out except that in Step 2, a carboxylic acid represented by formula (72-1) was used instead of the carboxylic acid represented by formula (8-1), N-methylaniline was used instead of diphenylamine, and in Step 3, methyl butyl ketone was used instead of 4-nonanone, to synthesize a naphthol compound represented by the following formula (73-1).

[0429]

[0430] Step 2: The reaction was carried out in the same manner as in Step 4 of Example 1, except that the compound represented by formula (73-1) was used instead of the compound represented by formula (1-4) and the compound represented by formula (2-1) was used instead of the compound represented by formula (1-5), to obtain a photochromic compound represented by the following formula (73-2) in a yield of 68%.

[0431]

[0432] The elemental analysis results of the photochromic compound represented by formula (73-2) were C: 80.51%, H: 6.91%, and N: 1.90%. ５０ H ５１ N.O. ５ The results were in good agreement with the calculated values ​​of C: 80.51%, H: 6.89%, and N: 1.88%. Furthermore, when the proton nuclear magnetic resonance spectrum was measured, 20H peaks due to methyl groups, butyl groups, and propyloxy groups were observed around δ 0.0 to 3.5 ppm, 11H peaks due to methoxy groups and propyloxy groups were observed around δ 3.5 to 5.0 ppm, and 20H peaks due to aromatic protons and alkene protons were observed around δ 5.0 to 9.0 ppm. １３ Measurement of the C-nuclear magnetic resonance spectrum showed a peak due to aromatic ring carbon at around δ 110 to 160 ppm, a peak due to alkene carbon at around δ 80 to 140 ppm, and a peak due to alkyl carbon at δ 20 to 60 ppm.

[0433] Example 74, Step 1 The reaction was carried out in the same manner as in Example 4, except that in Step 1, 3-bromo-4-methoxybenzophenone was replaced with 3-bromo-4,4'-dimethoxybenzophenone, and in Step 2, methyl ethyl ketone was replaced with ethyl propyl ketone, to synthesize a naphthol compound represented by the following formula (74-1).

[0434]

[0435] Step 2 The reaction was carried out in the same manner as in Step 4 of Example 1, except that the compound represented by formula (74-1) was used instead of the compound represented by formula (1-4) and the compound represented by formula (3-1) was used instead of the compound represented by formula (1-5), to obtain a photochromic compound represented by the following formula (74-2) in a yield of 68%.

[0436]

[0437] The elemental analysis results of the photochromic compound represented by formula (74-2) were C: 77.40%, H: 6.36%, N: 1.82%, and S: 4.11%. ５０ H ４９ NO ５ These were in good agreement with the calculated values ​​of C: 77.39%, H: 6.36%, N: 1.81%, and S: 4.13%. Furthermore, when the proton nuclear magnetic resonance spectrum was measured, it showed 18H peaks due to methyl groups, ethyl groups, and morpholino groups around δ 0.0 to 3.5 ppm, 13H peaks due to methoxy groups and morpholino groups around δ 3.5 to 5.0 ppm, and 18H peaks due to aromatic protons and alkene protons around δ 5.0 to 9.0 ppm. １３ Measurement of the C-nuclear magnetic resonance spectrum showed a peak due to aromatic ring carbon at around δ 110 to 160 ppm, a peak due to alkene carbon at around δ 80 to 140 ppm, and a peak due to alkyl carbon at δ 20 to 60 ppm.

[0438] Example 75, Step 1 The naphthol compound represented by the following formula (75-1) was synthesized in the same manner as in Example 8, except that in Step 1, 4-bromo-4'-methoxybenzophenone was used instead of 4-bromo-3-methyl-4'-methoxybenzophenone, in Step 2, benzmorpholine was used instead of diphenylamine, and in Step 3, methyl ethyl ketone was used instead of 4-nonanone.

[0439]

[0440] Step 2 The reaction was carried out in the same manner as in Step 4 of Example 1, except that the compound represented by formula (75-1) was used instead of the compound represented by formula (1-4) and the compound represented by formula (2-1) was used instead of the compound represented by formula (1-5), to obtain a photochromic compound represented by the following formula (75-2) in a yield of 67%.

[0441]

[0442] The elemental analysis results of the photochromic compound represented by formula (75-2) were C: 80.63%, H: 6.51%, and N: 1.91%. ４９ H ４７ N.O. ５ These values ​​were in good agreement with the calculated values ​​of C: 80.63%, H: 6.49%, and N: 1.92%. Furthermore, when the proton nuclear magnetic resonance spectrum was measured, 18H peaks due to methyl groups, ethyl groups, benzmorpholino groups, and propyloxy groups were observed around δ 0.0 to 3.5 ppm, 10H peaks due to methoxy groups and benzmorpholino groups were observed around δ 3.5 to 5.0 ppm, and 19H peaks due to aromatic protons and alkene protons were observed around δ 5.0 to 9.0 ppm. １３ Measurement of the C-nuclear magnetic resonance spectrum showed a peak due to aromatic ring carbon at around δ 110 to 160 ppm, a peak due to alkene carbon at around δ 80 to 140 ppm, and a peak due to alkyl carbon at δ 20 to 60 ppm.

[0443] Example 76, Step 1 The compound represented by the following formula (76-1) was synthesized in the same manner as in Step 1 of Example 10, except that 3-bromo-4-methoxybenzophenone was used instead of 3-bromo-4-methoxy-4'-methylbenzophenone, 4-chlorophenylboronic acid was used instead of 4-morpholinophenylboronic acid, and ethyl butyl ketone was used instead of 4-octanone.

[0444]

[0445] Step 2: The reaction was carried out in the same manner as in Step 1 of Example 6, except that the compound represented by formula (76-1) was used instead of the carboxylic acid represented by formula (4-1) and diphenylamine was used instead of morpholine. After completion of the reaction, water was added, the mixture was separated, and washing with water was repeated until the pH of the aqueous layer reached 7. The resulting organic layer was concentrated and purified by silica gel chromatography to obtain the compound represented by the following formula (76-2) in a yield of 94%.

[0446]

[0447] Step 3 The naphthol compound represented by the following formula (76-3) was synthesized in the same manner as in Step 2 of Example 1, except that the compound represented by formula (76-2) was used instead of the compound represented by formula (1-2).

[0448]

[0449] Step 4: The reaction was carried out in the same manner as in Step 1 of Example 17, except that 3-fluoro-4-propoxybenzene was used instead of 3-bromoanisole and 4-bromobenzoyl chloride was used instead of 4'-(1,1-dimethylethyl)[1,1'-biphenyl]-4-carbonyl chloride, to synthesize benzophenone represented by the following formula (76-4).

[0450]

[0451] Step 5: The reaction was carried out in the same manner as in Step 1 of Example 12, except that benzophenone represented by formula (76-4) was used instead of 4-bromo-4'-methoxybenzophenone and N-methylaniline was used instead of diphenylamine, to synthesize propargyl alcohol represented by the following formula (76-5).

[0452]

[0453] Step 6 The reaction was carried out in the same manner as in Step 4 of Example 1, except that the compound represented by formula (76-3) was used instead of the compound represented by formula (1-4) and the compound represented by formula (76-5) was used instead of the compound represented by formula (1-5), to obtain a photochromic compound represented by the following formula (76-6) in a yield of 64%.

[0454]

[0455] The elemental analysis results of the photochromic compound represented by formula (76-6) were C: 83.69%, H: 6.41%, and N: 2.91%. ６７ H ６１ FN ２ O ３ The results were in good agreement with the calculated values ​​of C: 83.72%, H: 6.40%, and N: 2.91%. Furthermore, when the proton nuclear magnetic resonance spectrum was measured, it showed 22H peaks due to methyl groups, ethyl groups, butyl groups, and propyloxy groups around δ 0.0 to 3.5 ppm, 5H peaks due to methoxy groups and propyloxy groups around δ 3.5 to 5.0 ppm, and 34H peaks due to aromatic protons and alkene protons around δ 5.0 to 9.0 ppm. １３ Measurement of the C-nuclear magnetic resonance spectrum showed a peak due to aromatic ring carbon at around δ 110 to 160 ppm, a peak due to alkene carbon at around δ 80 to 140 ppm, and a peak due to alkyl carbon at δ 20 to 60 ppm.

[0456] Example 77, Step 1 The reaction was carried out in the same manner as in Step 1 of Example 74, except that ethyl butyl ketone was used instead of methyl ethyl ketone, to obtain a photochromic compound represented by the following formula (77-1) in a yield of 60%.

[0457]

[0458] The elemental analysis results of the photochromic compound represented by formula (77-1) were C: 83.69%, H: 6.41%, N: 2.91%, and S: 3.92%. ５３ H ５５ NO ５These were in good agreement with the calculated values ​​of C: 77.81%, H: 6.78%, N: 1.71%, and S: 3.92%. Furthermore, when the proton nuclear magnetic resonance spectrum was measured, 24H peaks due to methyl groups, ethyl groups, butyl groups, and morpholino groups were observed around δ 0.0 to 3.5 ppm, 13H peaks due to methoxy groups and morpholino groups were observed around δ 3.5 to 5.0 ppm, and 18H peaks due to aromatic protons and alkene protons were observed around δ 5.0 to 9.0 ppm. １３ Measurement of the C-nuclear magnetic resonance spectrum showed a peak due to aromatic ring carbon at around δ 110 to 160 ppm, a peak due to alkene carbon at around δ 80 to 140 ppm, and a peak due to alkyl carbon at δ 20 to 60 ppm.

[0459] Example 78, Step 1 The reaction was carried out in the same manner as in Step 2 of Example 13, except that 2,4,6-trimethoxyphenylboronic acid was used instead of 2,4-dimethoxyphenylboronic acid and ethyl propyl ketone was used instead of methyl ethyl ketone, to synthesize a naphthol compound represented by the following formula (78-1).

[0460]

[0461] Step 2 The reaction was carried out in the same manner as in Step 4 of Example 1, except that the compound represented by formula (78-1) was used instead of the compound represented by formula (1-4) and the compound represented by formula (12-1) was used instead of the compound represented by formula (1-5), to obtain a photochromic compound represented by the following formula (78-2) in a yield of 68%.

[0462]

[0463] The elemental analysis results of the photochromic compound represented by formula (78-2) were C: 81.35%, H: 6.25%, and N: 1.56%. ６０ H ５５ NO ６The results were in good agreement with the calculated values ​​of C: 81.33%, H: 6.26%, and N: 1.58%. Furthermore, when the proton nuclear magnetic resonance spectrum was measured, it showed 12H peaks due to ethyl groups and propyl groups around δ 0.0 to 3.5 ppm, 15H peaks due to methoxy groups around δ 3.5 to 5.0 ppm, and 28H peaks due to aromatic protons and alkene protons around δ 5.0 to 9.0 ppm. １３ Measurement of the C-nuclear magnetic resonance spectrum showed a peak due to aromatic ring carbon at around δ 110 to 160 ppm, a peak due to alkene carbon at around δ 80 to 140 ppm, and a peak due to alkyl carbon at δ 20 to 60 ppm.

[0464] Example 79 First Step The reaction was carried out in the same manner as in Example 10, except that ethyl propyl ketone was used instead of 4-octanone, to synthesize a naphthol compound represented by the following formula (79-1).

[0465]

[0466] Step 2 The reaction was carried out in the same manner as in Step 4 of Example 1, except that the compound represented by formula (79-1) was used instead of the compound represented by formula (1-4) and the compound represented by formula (3-1) was used instead of the compound represented by formula (1-5), to obtain a photochromic compound represented by the following formula (79-2) in a yield of 60%.

[0467]

[0468] The elemental analysis results of the photochromic compound represented by formula (79-2) were C: 79.79%, H: 6.93%, and N: 3.48%. ５４ H ５６ N ２ O ５The results were in good agreement with the calculated values ​​of C: 79.77%, H: 6.94%, and N: 3.45%. Furthermore, when the proton nuclear magnetic resonance spectrum was measured, 23H peaks due to methyl groups, ethyl groups, propyl groups, and morpholino groups were observed around δ 0.0 to 3.5 ppm, 14H peaks due to methoxy groups and morpholino groups were observed around δ 3.5 to 5.0 ppm, and 19H peaks due to aromatic protons and alkene protons were observed around δ 5.0 to 9.0 ppm. １３ Measurement of the C-nuclear magnetic resonance spectrum showed a peak due to aromatic ring carbon at around δ 110 to 160 ppm, a peak due to alkene carbon at around δ 80 to 140 ppm, and a peak due to alkyl carbon at δ 20 to 60 ppm.

[0469] Example 80 First Step The reaction was carried out in the same manner as in Example 9, except that ethyl butyl ketone was used instead of methyl ethyl ketone, to synthesize a naphthol compound represented by the following formula (80-1).

[0470]

[0471] Step 2 The reaction was carried out in the same manner as in Step 4 of Example 1, except that the compound represented by formula (80-1) was used instead of the compound represented by formula (1-4) and the compound represented by formula (5-5) was used instead of the compound represented by formula (1-5), to obtain a photochromic compound represented by the following formula (80-2) in a yield of 60%.

[0472]

[0473] The elemental analysis results of the photochromic compound represented by formula (80-2) were C: 82.15%, H: 6.77%, and N: 1.99%. ４８ H ４７ NO ４The results were in good agreement with the calculated values ​​of C: 82.14%, H: 6.75%, and N: 2.00%. Furthermore, when the proton nuclear magnetic resonance spectrum was measured, it showed 17H peaks due to methyl groups, ethyl groups, and butyl groups around δ 0.0 to 3.5 ppm, a 9H peak due to methoxy groups around δ 3.5 to 5.0 ppm, and a 21H peak due to aromatic protons and alkene protons around δ 5.0 to 9.0 ppm. １３ Measurement of the C-nuclear magnetic resonance spectrum showed a peak due to aromatic ring carbon at around δ 110 to 160 ppm, a peak due to alkene carbon at around δ 80 to 140 ppm, and a peak due to alkyl carbon at δ 20 to 60 ppm.

[0474] Example 81, Step 1 The reaction was carried out in the same manner as in Example 76, except that in Step 1, 4-chlorophenylboronic acid was replaced with 2-chlorophenylboronic acid, and in Step 2, morpholine was used instead of diphenylamine, to synthesize a naphthol compound represented by the following formula (81-1).

[0475]

[0476] Step 2 The reaction was carried out in the same manner as in Step 4 of Example 1, except that the compound represented by formula (81-1) was used instead of the compound represented by formula (1-4) and the compound represented by formula (5-5) was used instead of the compound represented by formula (1-5), to obtain a photochromic compound represented by the following formula (81-2) in a yield of 68%.

[0477]

[0478] The elemental analysis results of the photochromic compound represented by formula (81-2) were C: 80.83%, H: 6.77%, and N: 1.85%. ５１ H ５１ NO ５The results were in good agreement with the calculated values ​​of C: 80.82%, H: 6.78%, and N: 1.85%. Furthermore, when the proton nuclear magnetic resonance spectrum was measured, it showed 18H peaks due to ethyl groups, butyl groups, and morpholino groups around δ 0.0 to 3.5 ppm, 13H peaks due to methoxy groups and morpholino groups around δ 3.5 to 5.0 ppm, and 20H peaks due to aromatic protons and alkene protons around δ 5.0 to 9.0 ppm. １３ Measurement of the C-nuclear magnetic resonance spectrum showed a peak due to aromatic ring carbon at around δ 110 to 160 ppm, a peak due to alkene carbon at around δ 80 to 140 ppm, and a peak due to alkyl carbon at δ 20 to 60 ppm.

[0479] Example 82, First Step: The reaction was carried out in the same manner as in Example 73, First Step, except that ethyl butyl ketone was used instead of methyl butyl ketone, to obtain a photochromic compound represented by the following formula (82-1) in a yield of 71%.

[0480]

[0481] The elemental analysis results of the photochromic compound represented by formula (82-1) were C: 80.63%, H: 7.01%, and N: 1.85%. ５１ H ５３ NO ５ The results were in good agreement with the calculated values ​​of C: 80.60%, H: 7.03%, and N: 1.84%. Furthermore, when the proton nuclear magnetic resonance spectrum was measured, it showed 22H peaks due to methyl groups, ethyl groups, butyl groups, and propyloxy groups around δ 0.0 to 3.5 ppm, 11H peaks due to methoxy groups and propyloxy groups around δ 3.5 to 5.0 ppm, and 20H peaks due to aromatic protons and alkene protons around δ 5.0 to 9.0 ppm. １３ Measurement of the C-nuclear magnetic resonance spectrum showed a peak due to aromatic ring carbon at around δ 110 to 160 ppm, a peak due to alkene carbon at around δ 80 to 140 ppm, and a peak due to alkyl carbon at δ 20 to 60 ppm.

[0482] Example 83 First Step The reaction was carried out in the same manner as in Example 9, except that ethyl propyl ketone was used instead of methyl ethyl ketone, to synthesize a naphthol compound represented by the following formula (83-1).

[0483]

[0484] Step 2 The reaction was carried out in the same manner as in Step 4 of Example 1, except that the compound represented by formula (83-1) was used instead of the compound represented by formula (1-4) and the compound represented by formula (12-1) was used instead of the compound represented by formula (1-5), to obtain a photochromic compound represented by the following formula (83-2) in a yield of 68%.

[0485]

[0486] The elemental analysis results of the photochromic compound represented by formula (83-2) were C: 84.43%, H: 6.33%, and N: 3.39%. ５８ H ５２ N ２ O ３ The results were in good agreement with the calculated values ​​of C: 84.43%, H: 6.35%, and N: 3.40%. Furthermore, when the proton nuclear magnetic resonance spectrum was measured, it showed 15H peaks due to methyl groups, ethyl groups, and propyl groups around δ 0.0 to 3.5 ppm, a 6H peak due to methoxy groups around δ 3.5 to 5.0 ppm, and a 31H peak due to aromatic protons and alkene protons around δ 5.0 to 9.0 ppm. １３ Measurement of the C-nuclear magnetic resonance spectrum showed a peak due to aromatic ring carbon at around δ 110 to 160 ppm, a peak due to alkene carbon at around δ 80 to 140 ppm, and a peak due to alkyl carbon at δ 20 to 60 ppm.

[0487] Example 84 The reaction was carried out in the same manner as in Example 1, except that in step 4, the compound represented by formula (79-1) was used instead of the compound represented by formula (1-4) and the compound represented by formula (7-2) was used instead of the compound represented by formula (1-5), to obtain a photochromic compound represented by the following formula (84-1) in a yield of 56%.

[0488]

[0489] The elemental analysis results of the photochromic compound represented by formula (84-1) were C: 83.79%, H: 6.93%, and N: 3.44%. ５７ H ５６ N ２ O ３ The results were in good agreement with the calculated values ​​of C: 83.79%, H: 6.91%, and N: 3.43%. Furthermore, when the proton nuclear magnetic resonance spectrum was measured, 25H peaks due to methyl groups, ethyl groups, propyl groups, and morpholino groups were observed around δ 0.0 to 3.5 ppm, 7H peaks due to methoxy groups and morpholino groups were observed around δ 3.5 to 5.0 ppm, and 24H peaks due to aromatic protons and alkene protons were observed around δ 5.0 to 9.0 ppm. １３ Measurement of the C-nuclear magnetic resonance spectrum showed a peak due to aromatic ring carbon at around δ 110 to 160 ppm, a peak due to alkene carbon at around δ 80 to 140 ppm, and a peak due to alkyl carbon at δ 20 to 60 ppm.

[0490] Example 85 The reaction was carried out in the same manner as in Example 74, except that butylhexyl ketone was used instead of methyl ethyl ketone in the first step, to obtain a photochromic compound represented by the following formula (85-1) in a yield of 55%.

[0491]

[0492] The elemental analysis results of the photochromic compound represented by formula (85-1) were C: 78.30%, H: 7.28%, N: 1.59%, and S: 3.66%. ５７ H ６３ NO ５These were in good agreement with the calculated values ​​of C: 78.31%, H: 7.26%, N: 1.60%, and S: 3.67%. Furthermore, when the proton nuclear magnetic resonance spectrum was measured, it showed 32H peaks due to methyl groups, butyl groups, hexyl groups, and morpholino groups around δ 0.0 to 3.5 ppm, 13H peaks due to methoxy groups and morpholino groups around δ 3.5 to 5.0 ppm, and 18H peaks due to aromatic protons and alkene protons around δ 5.0 to 9.0 ppm. １３ Measurement of the C-nuclear magnetic resonance spectrum showed a peak due to aromatic ring carbon at around δ 110 to 160 ppm, a peak due to alkene carbon at around δ 80 to 140 ppm, and a peak due to alkyl carbon at δ 20 to 60 ppm.

[0493] Example 86 The reaction was carried out in the same manner as in Example 13, except that the compound represented by formula (76-5) was used instead of the compound represented by formula (13-1) in the second step, to obtain a photochromic compound represented by the following formula (86-1) in a yield of 63%.

[0494]

[0495] The elemental analysis results of the photochromic compound represented by formula (86-1) were C: 79.86%, H: 6.20%, and N: 1.72%. ５４ H ５０ FNO ５ The results were in good agreement with the calculated values ​​of C: 79.88%, H: 6.21%, and N: 1.73%. Furthermore, when the proton nuclear magnetic resonance spectrum was measured, it showed 16H peaks due to methyl groups, ethyl groups, and propyloxy groups around δ 0.0 to 3.5 ppm, 11H peaks due to methoxy groups and propyloxy groups around δ 3.5 to 5.0 ppm, and 23H peaks due to aromatic protons and alkene protons around δ 5.0 to 9.0 ppm. １３ Measurement of the C-nuclear magnetic resonance spectrum showed a peak due to aromatic ring carbon at around δ 110 to 160 ppm, a peak due to alkene carbon at around δ 80 to 140 ppm, and a peak due to alkyl carbon at δ 20 to 60 ppm.

[0496] Example 87, First Step: The reaction was carried out in the same manner as in Example 73, First Step, except that ethyl propyl ketone was used instead of methyl butyl ketone, to obtain a photochromic compound represented by the following formula (87-1) in a yield of 72%.

[0497]

[0498] The elemental analysis results of the photochromic compound represented by formula (87-1) were C: 80.53%, H: 6.89%, and N: 1.88%. ５０ H ５１ NO ５ The results were in good agreement with the calculated values ​​of C: 80.51%, H: 6.89%, and N: 1.88%. Furthermore, when the proton nuclear magnetic resonance spectrum was measured, 20H peaks due to methyl groups, ethyl groups, propyl groups, and propyloxy groups were observed around δ 0.0 to 3.5 ppm, 11H peaks due to methoxy groups and propyloxy groups were observed around δ 3.5 to 5.0 ppm, and 20H peaks due to aromatic protons and alkene protons were observed around δ 5.0 to 9.0 ppm. １３ Measurement of the C-nuclear magnetic resonance spectrum showed a peak due to aromatic ring carbon at around δ 110 to 160 ppm, a peak due to alkene carbon at around δ 80 to 140 ppm, and a peak due to alkyl carbon at δ 20 to 60 ppm.

[0499] Example 88, Step 1 A naphthol compound represented by the following formula (88-1) was synthesized in the same manner as in Step 1 of Example 4, except that a carboxylic acid compound represented by formula (8-1) was used instead of the carboxylic acid represented by formula (4-1).

[0500]

[0501] Step 2 The reaction was carried out in the same manner as in Step 4 of Example 1, except that the compound represented by formula (88-1) was used instead of the compound represented by formula (1-4) and the compound represented by formula (13-1) was used instead of the compound represented by formula (1-5), to obtain a photochromic compound represented by the following formula (88-2) in a yield of 61%.

[0502]

[0503] The elemental analysis results of the photochromic compound represented by formula (88-2) were C: 81.69%, H: 6.45%, N: 1.77%, and S: 4.02%. ５４ H ５１ NO ３ The calculated values ​​of C: 81.68%, H: 6.47%, N: 1.76%, and S: 4.04% were in good agreement with the calculated values ​​of S. Furthermore, when the proton nuclear magnetic resonance spectrum was measured, 21H peaks due to methyl groups, ethyl groups, and propyl groups were observed around δ 0.0 to 3.5 ppm, a 6H peak due to methoxy groups was observed around δ 3.5 to 5.0 ppm, and a 24H peak due to aromatic protons and alkene protons was observed around δ 5.0 to 9.0 ppm. １３ Measurement of the C-nuclear magnetic resonance spectrum showed a peak due to aromatic ring carbon at around δ 110 to 160 ppm, a peak due to alkene carbon at around δ 80 to 140 ppm, and a peak due to alkyl carbon at δ 20 to 60 ppm.

[0504] Example 89 The reaction was carried out in the same manner as in Example 78, except that methyl propyl ketone was used instead of ethyl propyl ketone in the first step, to obtain a photochromic compound represented by the following formula (89-1) in a yield of 63%.

[0505]

[0506] The elemental analysis results of the photochromic compound represented by formula (89-1) were C: 81.24%, H: 6.16%, and N: 1.60%. ５９ H ５３ NO ６ The results were in good agreement with the calculated values ​​of C: 81.26%, H: 6.13%, and N: 1.61%. Furthermore, when the proton nuclear magnetic resonance spectrum was measured, it showed 10H peaks due to methyl groups and propyl groups around δ 0.0 to 3.5 ppm, 15H peaks due to methoxy groups around δ 3.5 to 5.0 ppm, and 28H peaks due to aromatic protons and alkene protons around δ 5.0 to 9.0 ppm. １３Measurement of the C-nuclear magnetic resonance spectrum showed a peak due to aromatic ring carbon at around δ 110 to 160 ppm, a peak due to alkene carbon at around δ 80 to 140 ppm, and a peak due to alkyl carbon at δ 20 to 60 ppm.

[0507] Example 90 The reaction was carried out in the same manner as in Example 15, except that 2-heptanone was used instead of 3-octanone, to obtain a photochromic compound represented by the following formula (90-1) in a yield of 62%.

[0508]

[0509] The elemental analysis results of the photochromic compound represented by formula (90-1) were C: 74.30% and H: 5.93%. ４３ H ４１ F ３ O ５ The results were in good agreement with the calculated values ​​of C: 74.33% and H: 5.95%. Furthermore, when the proton nuclear magnetic resonance spectrum was measured, it showed 16H peaks due to methyl groups and hexyl groups around δ 0.0 to 3.5 ppm, 9H peaks due to methoxy groups around δ 3.5 to 5.0 ppm, and 16H peaks due to aromatic protons and alkene protons around δ 5.0 to 9.0 ppm. １３ Measurement of the C-nuclear magnetic resonance spectrum showed a peak due to aromatic ring carbon at around δ 110 to 160 ppm, a peak due to alkene carbon at around δ 80 to 140 ppm, and a peak due to alkyl carbon at δ 20 to 60 ppm.

[0510] Example 91 The reaction was carried out in the same manner as in Example 3, except that ethyl propyl ketone was used instead of 4-methyl-3-hexanone, to obtain a photochromic compound represented by the following formula (91-1) in a yield of 67%.

[0511]

[0512] The elemental analysis results of the photochromic compound represented by formula (91-1) were C: 79.14%, H: 6.81%, and N: 2.09%. ４４ H ４５ NO ５The results were in good agreement with the calculated values ​​of C: 79.13%, H: 6.79%, and N: 2.10%. Furthermore, when the proton nuclear magnetic resonance spectrum was measured, it showed 16H peaks due to ethyl groups, propyl groups, and morpholino groups around δ 0.0 to 3.5 ppm, 13H peaks due to methoxy groups and morpholino groups around δ 3.5 to 5.0 ppm, and 16H peaks due to aromatic protons and alkene protons around δ 5.0 to 9.0 ppm. １３ Measurement of the C-nuclear magnetic resonance spectrum showed a peak due to aromatic ring carbon at around δ 110 to 160 ppm, a peak due to alkene carbon at around δ 80 to 140 ppm, and a peak due to alkyl carbon at δ 20 to 60 ppm.

[0513] Examples 92 to 111 Photochromic laminates were prepared using the photochromic compounds obtained in Examples 72 to 91 in the same manner as in Example 21. The evaluation results are summarized in Tables 6 and 7.

[0514]

[0515]

[0516] (Examples 112 to 127, Comparative Examples 13 to 20) The solubility in polymerizable compounds was evaluated using the photochromic compounds according to the Examples and Comparative Examples shown in Tables 8 to 14 in the same manner as in Example 67. In Comparative Examples 13 to 20, the solubility in polymerizable compounds was evaluated using the photochromic compounds represented by the following formulas (E) to (L).

[0517] (Synthesis of Compound Represented by Formula (E)) The compound represented by the following formula (E) was synthesized by carrying out the reaction in the same manner as in Example 3, except that 3,3,5,5-tetramethylcyclohexanone was used instead of 4-methyl-3-hexanone.

[0518]

[0519] (Synthesis of Compound Represented by Formula (F)) The following compound represented by formula (F) was synthesized by carrying out the reaction in the same manner as in Example 9, except that diethyl ketone was used instead of methyl ethyl ketone.

[0520]

[0521] (Synthesis of Compound Represented by Formula (G)) The reaction was carried out in the same manner as in Example 9, except that acetone was used instead of 4-octanone, to synthesize the compound represented by the following formula (G).

[0522]

[0523] (Synthesis of Compound Represented by Formula (H)) The reaction was carried out in the same manner as in Example 15, except that acetone was used instead of 3-octanone, to synthesize the compound represented by the following formula (H).

[0524]

[0525] (Synthesis of Compound Represented by Formula (I)) The following compound represented by formula (I) was synthesized by carrying out the reaction in the same manner as in Example 73, except that acetone was used instead of methyl butyl ketone.

[0526]

[0527] (Synthesis of Compound Represented by Formula (J)) The compound represented by the following formula (J) was synthesized by carrying out the reaction in the same manner as in Example 74, except that 4,4-diethylcyclohexanone was used instead of methyl ethyl ketone.

[0528]

[0529] (Synthesis of Compound Represented by Formula (K)) The following compound represented by formula (K) was synthesized by carrying out the reaction in the same manner as in Example 74, except that acetone was used instead of methyl ethyl ketone.

[0530]

[0531] (Synthesis of Compound Represented by Formula (L)) The reaction was carried out in the same manner as in Example 78, except that acetone was used instead of ethyl propyl ketone, to synthesize the compound represented by the following formula (L).

[0532]

[0533]

[0534]

[0535]

[0536]

[0537]

[0538]

[0539]

[0540] Preferred embodiments of the present disclosure are listed below.

[0541] [1] A photochromic compound having a skeleton represented by the following formula (3):

[0542]

[0543] In the formula (1), M is C, Si, or Ge, and R １ is a hydrogen atom or a substituent, and when it is a substituent, it is not a halogen atom or a trifluoromethyl group, ２ is a hydrogen atom or a substituent, and when it is a substituent, it is not a halogen atom, ３ and R ４ are each independently a linear or branched alkyl group and have mutually different structures; ５ and R ６ are each independently a hydrogen atom or a substituent, R ７ and R ８ are each independently a substituent, and b and c are each independently 0 or an integer of 1 to 3.

[0544] [2] In the formula (3), R ３ is a linear or branched alkyl group having 1 to 19 carbon atoms, and R ４ is a linear or branched alkyl group having 2 to 20 carbon atoms, and R ４ From the number of carbon atoms in the alkyl group, R ３The photochromic compound according to [1], wherein the value obtained by subtracting the number of carbon atoms of the alkyl group from the above is 1 or more and 10 or less.

[0545] [3] In the formula (3), R ３ is a linear alkyl group having 1 to 10 carbon atoms.

[0546] [4] In the formula (3), R ３ is a linear alkyl group having 1 to 9 carbon atoms, and R ４ is a linear alkyl group having 2 to 10 carbon atoms, and R ４ From the number of carbon atoms in the alkyl group, R ３ The photochromic compound according to any one of [1] to [3], wherein the value obtained by subtracting the number of carbon atoms of the alkyl group from the above is 1 or more and 9 or less.

[0547] [5] In the formula (3), R ３ [5] The photochromic compound according to any one of [1] to [4], wherein is any one of a methyl group, an ethyl group, and a propyl group.

[0548] [6] In the formula (3), R ３ and R ４ [6] The photochromic compound according to any one of [1] to [5], wherein either one of

[0549] [7] In the formula (3), R ７ , and R ８each independently represents 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 hydroxycarbonyl group, a substituted or unsubstituted alkylcarbonyl group, a substituted or unsubstituted alkoxycarbonyl group, a substituted or unsubstituted aralkyl group, a substituted or an 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 the following formula (2a), a group represented by the following formula (X), or a group represented by the following formula (X3), wherein in formula (3), when b is 2 or 3, a plurality of R ７ may be the same or different, and when c is 2 or 3, a plurality of R ８ may be the same or different, b is 2 to 3, and adjacent R ７ If there is a ７ is R ７ and a carbon atom bonded to the R may form a substituted or unsubstituted aliphatic ring, a substituted or unsubstituted aliphatic heterocycle, a substituted or unsubstituted aromatic ring, a substituted or unsubstituted aromatic heterocycle, or a substituted or unsubstituted fused polycycle in which an aromatic ring or an aromatic heterocycle is fused to any of these rings, ８ If there is a ８ is R ８and -Q may together with the carbon atom bonded to form a substituted or unsubstituted aliphatic ring, a substituted or unsubstituted aliphatic heterocycle, a substituted or unsubstituted aromatic ring, a substituted or unsubstituted aromatic heterocycle, or a substituted or unsubstituted fused polycycle in which an aromatic ring or an aromatic heterocycle is fused to any of these rings, １ -(X １ Q ２ ) a-X ２ Q ３ (2a) In the formula (2a), Q １ is an alkylene group or a haloalkylene group, ２ is an alkylene group or a haloalkylene group, ３ is an alkyl group or a haloalkyl group, １ , and X ２ are each independently O, S, or NR ７００ , P.R. ７０１ , or P(=O), R ７００ , and R ７０１ 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 0 or an integer of 1 to 3; L １ -R ４００ (X3) In the formula (X3), R ４００ is a hydrogen atom, an alkyl group, an aryl group, a polymerizable group, a photochromic group, or a silyl group having an alkyl group, an alkoxy group, or an aryl group as a substituent; L １ is a group represented by the following formula (X2):

[0550]

[0551] In the formula (X2), R ３０ is a group represented by the following formula (X2a):

[0552]

[0553] In the formula (X2) and the formula (X2a), J represents a divalent group, each of which independently represents a direct bond, a substituted or unsubstituted methylene group, an oxygen atom, a sulfur atom, or NR ３０１ and R ３０１ is a hydrogen atom or an alkyl group, L is an oxygen atom or a sulfur atom, R ３００ is an alkylene group or a silylene group having an alkyl group or an aryl group as a substituent, and R ３０２ , R ３０３ , and R ３０４ are each independently an alkylene group; h, j, k, and l are each independently 0 or 1; i is an integer of 0 to 200, and when i is 2 or greater, a plurality of R ３０ may be the same or different, and the dashed line represents R ４００ represents a bond with

[0554]

[0555] In the formula (X), E is an oxygen atom or NR １０１ and R １０１ 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 NR ２０２ and R ２０２ is a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a heteroaryl group; g is 0 or 1; R ２０１ is a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a heteroaryl group, and when G is an oxygen atom or a sulfur atom, R ２０１ is a group other than a hydrogen atom.

[0556] [8] In the formula (3), R ５ and R ６ are each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[0557] [9] A photochromic compound according to any one of [1] to [8], represented by the following formula (4):

[0558]

[0559] In the formula (4), R １ , R ２ , R ３ , R ４ , R ７ , R ８ , b, c, and M each independently have the same meaning as in the formula (3), ９ and R １０ are each independently a hydroxyl group, an alkyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, an alkoxy group having 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 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), or a group represented by formula (X3), d is an integer of 0 to 5, and when d is 2 to 5, a plurality of R ９ may be the same or different groups, and adjacent R ９ If there is a ９ is R ９ may form, together with the carbon atom bonded to R, a substituted or unsubstituted aliphatic ring, a substituted or unsubstituted aliphatic heterocycle, a substituted or unsubstituted aromatic ring, a substituted or unsubstituted aromatic heterocycle, or a substituted or unsubstituted fused polycycle in which an aromatic ring or an aromatic heterocycle is fused to any of these rings, e is an integer of 0 to 5, and when e is 2 to 5, a plurality of R １０ may be the same or different groups, and adjacent R １０ If there is a １０ is R １０and the carbon atom bonded to the ring may form a substituted or unsubstituted aliphatic ring, a substituted or unsubstituted aliphatic heterocycle, a substituted or unsubstituted aromatic ring, a substituted or unsubstituted aromatic heterocycle, or a substituted or unsubstituted fused polycycle in which an aromatic ring or an aromatic heterocycle is fused to any of these rings.

[0560]

[10] In the formula (3), R １ is a hydrogen atom, a hydroxyl group, a substituted or unsubstituted alkyl 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 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 (2a), a group represented by formula (X), or a group represented by formula (X3), R ２is 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 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 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 the formula (2a), a group represented by the formula (X), or a group represented by the formula (X3). [1] to [9] The photochromic compound according to any one of the above.

[0561]

[11] In the formula (3), R １ is a hydrogen atom, a substituted or unsubstituted alkyl 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 substituted or unsubstituted alkylthio group, 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 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 the formula (2a), a group represented by the formula (X), or a group represented by the formula (X3). [1] The photochromic compound according to any one of [1] to

[10] .

[0562]

[12] A photochromic compound according to any one of [1] to

[11] , represented by the following formula (5):

[0563]

[0564] In the formula (5), R １ , R ２ , R ３ , R ４ , R ７ , R ８ , R ９ , R １０ , d, and e each independently have the same meaning as in the formula (4), １ and Z ２ 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 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 the formula (2a), a group represented by the formula (X), or a group represented by the formula (X3), bb is an integer of 0 to 2, and cc is an integer of 0 to 2, and when bb is 2, a plurality of R ７ may be the same or different, and when cc is 2, a plurality of R ８ may be the same or different from each other.

[0565]

[13] In the formula (5), R ２ is a hydrogen atom, bb is 0, and cc is 0. The photochromic compound according to

[12] .

[0566]

[14] In the formula (5), Z ２is 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 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 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 the formula (2a), a group represented by the formula (X), or a group represented by the formula (X3). The photochromic compound according to

[12] or

[13] .

[0567]

[15] A curable composition comprising the photochromic compound according to any one of [1] to

[14] and at least one selected from the group consisting of radically polymerizable monomers, cationically polymerizable monomers, compounds having a polymerization reactive group, and (thio)urethane (urea) polymers.

[16] A cured product of the curable composition according to

[15] .

[17] An optical article comprising the cured product according to

[16] .

[18] A lens comprising the photochromic compound according to any one of [1] to

[14] .

[19] Eyeglasses comprising the lens according to

[18] .

Claims

1. A photochromic compound represented by the following formula (3): In the formula (3), M is C, Si, or Ge; R １ is a hydrogen atom or a substituent, and when it is a substituent, it is not a halogen atom or a trifluoromethyl group; R ２ is a hydrogen atom or a substituent, and when it is a substituent, it is not a halogen atom; R ３ and R ４ are each independently a linear or branched alkyl group and have different structures; R ５ and R ６ are each independently a hydrogen atom or a substituent; R ７ and R ８ each independently represents a substituent; and b and c each independently represent 0 or an integer of 1 to 3.

2. In the formula (3), R ３ is a linear or branched alkyl group having 1 to 19 carbon atoms; R ４ is a linear or branched alkyl group having 2 to 20 carbon atoms; R ４ From the number of carbon atoms of the alkyl group, R ３ 2. The photochromic compound according to claim 1, wherein the value obtained by subtracting the number of carbon atoms of the alkyl group from the above is 1 or more and 10 or less.

3. In the formula (3), R ３ The photochromic compound according to claim 1, wherein is a linear alkyl group having 1 to 10 carbon atoms.

4. In the formula (3), R ３ is a linear alkyl group having 1 to 9 carbon atoms; R ４ is a linear alkyl group having 2 to 10 carbon atoms; R ４ From the number of carbon atoms of the alkyl group, R ３ 2. The photochromic compound according to claim 1, wherein the value obtained by subtracting the number of carbon atoms of the alkyl group from the above is 1 or more and 9 or less.

5. In the formula (3), R ３ 2. The photochromic compound according to claim 1, wherein is any one of a methyl group, an ethyl group, and a propyl group.

6. In the formula (3), R ３ and R ４ 2. The photochromic compound according to claim 1, wherein either one of the above is an ethyl group.

7. In the formula (3), R ７ , and R ８ each independently represents 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 hydroxycarbonyl group, a substituted or unsubstituted alkylcarbonyl group, a substituted or unsubstituted alkoxycarbonyl group, a substituted or unsubstituted aralkyl group, 2. The photochromic compound according to claim 1, wherein the R is a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl 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 the following formula (2a), a group represented by the following formula (X), or a group represented by the following formula (X3): ７ may be the same or different, and when c is 2 to 3, a plurality of R ８ may be the same or different, b is 2 to 3, and adjacent R ７ If there is a pair of adjacent R ７ is R ７ and may form, together with the carbon atom bonded to the ring, a substituted or unsubstituted aliphatic ring, a substituted or unsubstituted aliphatic heterocycle, a substituted or unsubstituted aromatic ring, a substituted or unsubstituted aromatic heterocycle, or a substituted or unsubstituted condensed polycycle in which an aromatic ring or an aromatic heterocycle is condensed to any of these rings, ８ If there is a pair of adjacent R ８ is R ８ and, together with the carbon atom bonded to -Q, a substituted or unsubstituted aliphatic ring, a substituted or unsubstituted aliphatic heterocycle, a substituted or unsubstituted aromatic ring, a substituted or unsubstituted aromatic heterocycle, or a substituted or unsubstituted condensed polycycle in which an aromatic ring or an aromatic heterocycle is condensed to any of these rings, １ - (X １ Q ２ ) a-X ２ Q ３ (2a) In the formula (2a), Q １ is an alkylene group or a haloalkylene group; Q ２ is an alkylene group or a haloalkylene group; Q ３ is an alkyl group or a haloalkyl group; X １ , and X ２ are each independently O, S, or NR ７００ , P.R. ７０１ or P(=O), R ７００ , and R ７０１ each independently represents 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 represents 0 or an integer of 1 to 3; １ -R ４００ (X3) In the formula (X3), R ４００ is a hydrogen atom, an alkyl group, an aryl group, a polymerizable group, a photochromic group, or a silyl group having an alkyl group, an alkoxy group, or an aryl group as a substituent; L １ is a group represented by the following formula (X2): In the formula (X2), R ３０ is a group represented by the following formula (X2a): In the formula (X2) and the formula (X2a), J is a divalent group, each of which independently represents a direct bond, a substituted or unsubstituted methylene group, an oxygen atom, a sulfur atom, or NR ３０１ and R ３０１ is a hydrogen atom or an alkyl group, L is an oxygen atom or a sulfur atom, R ３００ is an alkylene group or a silylene group having an alkyl group or an aryl group as a substituent, R ３０２ , R ３０３ , and R ３０４ are each independently an alkylene group; h, j, k, and l are each independently 0 or 1; i is an integer of 0 to 200, and when i is 2 or more, a plurality of R ３０ may be the same or different, and the dashed line represents R ４００ represents a bond with In the formula (X), E is an oxygen atom or NR １０１ and R １０１ 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 NR ２０２ and R ２０２ is a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a heteroaryl group; g is 0 or 1; R ２０１ 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, R ２０１ is a group other than a hydrogen atom.

8. In the formula (3), R ５ and R ６ The photochromic compound according to claim 1 , wherein each of the groups independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

9. The photochromic compound according to claim 7, represented by the following formula (4): In the formula (4), R １ , R ２ , R ３ , R ４ , R ７ , R ８ , b, c and M each independently have the same meaning as in formula (3); ９ and R １０ are each independently a hydroxyl group, an alkyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, an alkoxy group having 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 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, d is an integer of 0 to 5, and when d is 2 to 5, a plurality of R ９ may be the same or different groups, and adjacent R ９ If there is a pair of adjacent R ９ is R ９ and a carbon atom bonded to the ring may form a substituted or unsubstituted aliphatic ring, a substituted or unsubstituted aliphatic heterocycle, a substituted or unsubstituted aromatic ring, a substituted or unsubstituted aromatic heterocycle, or a substituted or unsubstituted condensed polycycle in which an aromatic ring or an aromatic heterocycle is condensed to the ring, e is an integer of 0 to 5, and when e is 2 to 5, a plurality of R １０ may be the same or different groups, and adjacent R １０ If there is a pair of adjacent R １０ is R １０ and the carbon atom bonded to the ring may form a substituted or unsubstituted aliphatic ring, a substituted or unsubstituted aliphatic heterocycle, a substituted or unsubstituted aromatic ring, a substituted or unsubstituted aromatic heterocycle, or a substituted or unsubstituted condensed polycycle in which an aromatic ring or an aromatic heterocycle is condensed to these rings.

10. In the formula (3), R １ is a hydrogen atom, a hydroxyl group, a substituted or unsubstituted alkyl 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 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 the formula (2a), a group represented by the formula (X), or a group represented by the formula (X3); ２ is 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 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 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 the formula (2a), a group represented by the formula (X), or a group represented by the formula (X3). The photochromic compound according to claim 7.

11. In the formula (3), R １ is a hydrogen atom, a substituted or unsubstituted alkyl 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 substituted or unsubstituted alkylthio group, 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 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 the formula (2a), a group represented by the formula (X), or a group represented by the formula (X3). The photochromic compound according to claim 7.

12. The photochromic compound according to claim 9, represented by the following formula (5): In the formula (5), R １ , R ２ , R ３ , R ４ , R ７ , R ８ , R ９ , R １０ , d and e each independently have the same meaning as in formula (4); １ and Z ２ 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 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 the formula (2a), a group represented by the formula (X), or a group represented by the formula (X3); bb is an integer of 0 to 2, cc is an integer of 0 to 2, and when bb is 2, a plurality of R ７ may be the same or different, and when cc is 2, a plurality of R ８ may be the same or different from each other.

13. In the formula (5), R ２ The photochromic compound according to claim 12 , wherein is a hydrogen atom, bb is 0, and cc is 0.

14. In the formula (5), Z ２ is 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 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 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 the formula (2a), a group represented by the formula (X), or a group represented by the formula (X3). The photochromic compound according to claim 12.

15. A curable composition comprising the photochromic compound according to claim 1 and at least one member selected from the group consisting of radically polymerizable monomers, cationic polymerizable monomers, compounds having a polymerization reactive group, and (thio)urethane (urea) polymers.

16. A cured product of the curable composition according to claim 15.

17. An optical article comprising the cured product according to claim 16.

18. A lens comprising the photochromic compound of claim 1.

19. Eyeglasses comprising the lens of claim 18.