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

Abstract

Provided is a photochromic composition containing one or more first photochromic compounds represented by formula (1) and one or more second photochromic compounds represented by formula (2). The photochromic composition may further contain a third photochromic compound represented by formula (9) and / or a fourth photochromic compound represented by formula (11). Also provided are a curable composition, an optical article, a lens, and eyeglasses, which all contain the photochromic composition.

Description

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

[0001] The present invention relates to photochromic compositions, curable compositions, optical articles, lenses, 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, and chromene compounds in particular have been extensively studied. Furthermore, many photochromic compositions containing a mixture of multiple photochromic compounds have also been investigated to achieve desired photochromic properties.

[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 irradiation with ultraviolet light (hereinafter referred to as "initial coloration"); (II) A high rate at which the color density reaches saturation after ultraviolet light irradiation begins (hereinafter also referred to as "high color development sensitivity"); (III) A high rate at which the original state is restored after ultraviolet light irradiation is stopped (hereinafter referred to as "fading rate"); and (IV) A high durability against repeated reversible action.

[0004] In recent years, the properties required of photochromic compounds have become more sophisticated, and there is an increasing demand for the compounds to exhibit photochromic properties even in an environment such as the inside of an automobile, where ultraviolet light of short wavelengths, for example, 380 nm or less, is blocked by a windshield or the like, thereby reducing the energy required for the photochromic compound to change to a color-developing state.

[0005] In order to meet such demands, various studies have been conducted, and for example, chromene compounds represented by the following formula (A) (see Patent Document 1), chromene compounds represented by the following formula (B) (see Patent Document 2), chromene compounds represented by the following formula (C) (see Patent Document 3), and the like have been proposed.

[0006]

[0007]

[0008]

[0009] International Publication No. WO 2006 / 110221, International Publication No. WO 2013 / 052338, International Publication No. WO 2018 / 054507, International Publication No. WO 2012 / 030518, International Publication No. WO 2018 / 235771, International Publication No. WO 2012 / 102410, International Publication No. WO 2013 / 042800, International Publication No. WO 2023 / 136213

[0010] An object of the present disclosure is to provide a photochromic composition that develops a deep color even in an environment where ultraviolet light is blocked, such as the interior of an automobile, has excellent durability, and is less prone to yellowing, and to provide a curable composition, optical article, lens, and eyeglasses that contain this photochromic composition.

[0011] According to the present disclosure, there is provided a photochromic composition, which includes a first photochromic compound represented by the following formula (1) and a second photochromic compound represented by the following formula (2):

[0012]

[0013] In the above formula (1), M is C, Si, or Ge.

[0014] Ring A is a substituted or unsubstituted aromatic hydrocarbon 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 the above ring. １ is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. １ R is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a group represented by the following formula (2a): ２ is a substituted or unsubstituted alkyl group having 2 to 20 carbon atoms, or a group represented by the following formula (2a):

[0015] -Q １ -(X １ Q２ ) a-X ２ Q ３ (2a) In the above 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). 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 an integer of 0 to 10.

[0016] R ３ is a substituent. b is an integer of 0 to 3. ５ and R ６ are each independently a hydrogen atom or a substituent.

[0017]

[0018] In the above formula (2), M ２ is C, Si, or Ge.

[0019] Z ２ and Z ３are each independently a hydrogen atom, a hydroxy group, a substituted or unsubstituted alkyl group, a haloalkyl group, a substituted or unsubstituted alkoxy group, a haloalkoxy group, a substituted or unsubstituted cycloalkyl 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 the above formula (2a), a group represented by the following formula (X), or a group represented by the following formula (X3).

[0020] Z ４ is a hydrogen atom, a hydroxy group, a substituted or unsubstituted alkyl group, a haloalkyl group, a substituted or unsubstituted alkoxy group, a haloalkoxy group, a substituted or unsubstituted cycloalkyl 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 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 the above formula (2a), a group represented by the following formula (X), or a group represented by the following formula (X3).

[0021]

[0022] In the above 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 ２０２and 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.

[0023] L １ -R ４００ (X3) In the above formula (X3), R ４００ L 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. １ is a group represented by the following formula (X2).

[0024]

[0025] In the above formula (X2), R ３０ is a group represented by the following formula (X2a):

[0026]

[0027] In the formula (X2) and the formula (X2a), J is a divalent group, and each J independently represents a direct bond, a substituted or unsubstituted methylene group, an oxygen atom, a sulfur atom, or an 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. 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, multiple R ３０ may be the same or different. The dashed line indicates R ４００ Represents a bond with

[0028] R １２ and R ２２are each independently a hydrogen atom or a substituent. ３２ and R ４２ are each independently a substituent. b2 is an integer of 0 or more and 2 or less, and c2 is an integer of 0 or more and 3 or less. R ５２ and R ６２ are each independently a hydrogen atom or a substituent.

[0029] According to the present disclosure, there is provided a curable composition, which includes the photochromic composition of the present disclosure 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.

[0030] According to the present disclosure, an optical article is provided. The optical article comprises a cured product of the curable composition of the present disclosure.

[0031] According to the present disclosure, a lens is provided, the lens comprising the photochromic composition of the present disclosure.

[0032] According to the present disclosure, eyeglasses are provided, the eyeglasses including lenses of the present disclosure.

[0033] According to the present disclosure, there are provided a photochromic composition that can develop a deep color even in an environment where ultraviolet rays are blocked, such as the interior of an automobile, and that has excellent durability and little yellowing, as well as a curable composition, optical article, lens, and eyeglasses that contain this photochromic composition.

[0034] In photochromic laminates, the photochromic layer may be required to be relatively thin to take advantage of the properties of the optical substrate. However, reducing the thickness of the photochromic layer may result in reduced durability during repeated use. Furthermore, in order to achieve sufficient photochromic properties in a thin film, a photochromic compound must be dispersed in the photochromic layer at a high concentration. In particular, to achieve deep color development even in environments with low UV radiation, such as the interior of an automobile, a photochromic compound with a molecular design that strongly absorbs visible light with wavelengths of 420 nm or more must be dispersed at a high concentration, as described in Patent Documents 1 to 4. However, such photochromic compounds may exhibit a yellow coloration in their pre-color development state, which is originally colorless. Furthermore, presumably due to their molecular design that strongly absorbs visible light with wavelengths of 420 nm or more, such photochromic compounds also exhibit a strong increase in yellowness (yellowing) upon degradation, and the pre-color development yellow coloration may further increase as the photochromic compound deteriorates.

[0035] The photochromic composition of the present disclosure contains one or more first photochromic compounds represented by the following formula (1) and one or more second photochromic compounds represented by the following formula (2).

[0036]

[0037] In the above formula (1), M is C, Si, or Ge. Ring A is a substituted or unsubstituted aromatic hydrocarbon 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 the above ring. Z １ is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. １ is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a group represented by formula (2a). ２ is a substituted or unsubstituted alkyl group having 2 to 20 carbon atoms, or a group represented by formula (2a). ３ is a substituent. b is an integer of 0 to 3. ５ and R ６are each independently a hydrogen atom or a substituent.

[0038]

[0039] In the above formula (2), M ２ is C, Si, or Ge. ２ and Z ３ are each independently a hydrogen atom, a hydroxy group, a substituted or unsubstituted alkyl group, a haloalkyl group, a substituted or unsubstituted alkoxy group, a haloalkoxy group, a substituted or unsubstituted cycloalkyl 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). Z ４ is a hydrogen atom, a hydroxy group, a substituted or unsubstituted alkyl group, a haloalkyl group, a substituted or unsubstituted alkoxy group, a haloalkoxy group, a substituted or unsubstituted cycloalkyl 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 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). １２ and R ２２ are each independently a hydrogen atom or a substituent.３２ and R ４２ are each independently a substituent. b2 is an integer of 0 or more and 2 or less, and c2 is an integer of 0 or more and 3 or less. R ５２ and R ６２ are each independently a hydrogen atom or a substituent.

[0040] This photochromic composition has excellent responsiveness in an environment where ultraviolet light is blocked, such as the interior of an automobile, and also has improved durability, and is particularly able to suppress yellowing that occurs during degradation. Although the reasons for this are not clear, the inventors believe that the following is true.

[0041] The first photochromic compound is Z １ The compound is characterized in that it has a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group as the substituent. By substituting with this substituent, the skeleton shown in the above formula (1) and the substituent Z １ It is believed that compounds having such a structure can be conjugated with the substituent Z １ It is believed that the conjugation is extended compared to compounds not substituted with , and this extension increases the amount of absorption of visible light, particularly at wavelengths of 410 nm or more and 450 nm or less, and is thought to improve the responsiveness in environments where ultraviolet light is blocked, such as the interior of a car. However, presumably due to the increased amount of absorption of visible light, the yellow coloring in the state before color development becomes stronger, and the yellow coloring of the deteriorated product produced when the photochromic compound deteriorates tends to become stronger.

[0042] The second photochromic compound is Z ２ and Z ３ It is a photochromic compound having a specific substituent at Z. ４ does not have a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group, and therefore does not obtain the effect of conjugation as in the first photochromic compound, and therefore tends to have lower responsiveness than the first photochromic compound in an environment where ultraviolet light is blocked, such as the inside of a car.

[0043] The photochromic composition of the present disclosure is used by mixing one or more first photochromic compounds represented by the above formula (1) with one or more second photochromic compounds represented by the above formula (2).

[0044] By using a mixture of the first photochromic compound and the second photochromic compound, the durability can be improved compared to when only the first photochromic compound is used, and yellowing upon deterioration can be particularly suppressed, presumably because the second photochromic compound acts as a stabilizer. Furthermore, because the first photochromic compound has a high absorption of visible light, it is thought that even when the first photochromic compound and the second photochromic compound are used in combination, a deep color can be developed in an environment where ultraviolet light is blocked.

[0045] Therefore, the photochromic composition of the present disclosure has reduced yellow coloration before color development, can develop a deep color even in an environment where ultraviolet light is blocked, exhibits high durability, and undergoes little yellowing upon degradation.

[0046] From the above, by using the photochromic composition of the present disclosure, it is possible to realize a cured product or optical article that reduces yellow coloration before color development, develops a deep color in an environment where ultraviolet light is blocked, has excellent durability, and is inhibited from yellowing during deterioration.

[0047] The photochromic composition of the present disclosure will be described in detail below.

[0048] Photochromic Composition The photochromic composition of the present disclosure includes a first photochromic compound and a second photochromic compound, and may be a mixture of the first photochromic compound and the second photochromic compound.

[0049] <First Photochromic Compound> The first photochromic compound is represented by the following formula (1): The first photochromic compound may be used alone or in combination of two or more types.

[0050]

[0051] (M) In the above formula (1), M is C, Si, or Ge. M is preferably C.

[0052] (Ring A) In the above formula (1), ring A is a substituted or unsubstituted aromatic hydrocarbon 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 the above ring. Examples of the substituent that ring A has include R ３ The same can be used.

[0053] Examples of the aromatic hydrocarbon ring include a benzene ring and a cyclotetradecaheptaene ring.

[0054] Examples of the aromatic heterocycle include a furan ring, a thiophene ring, and a pyridine ring.

[0055] Examples of the fused polycyclic ring include a naphthalene ring, a fluorene ring, an anthracene ring, a phenanthrene ring, a tetracene ring, a pentacene ring, a benzopyrene ring, a chrysene ring, a pyrene ring, a triphenylene ring, a perylene ring, a benzofuran ring, a benzothiophene ring, a quinoline ring, an isoquinoline ring, an indole ring, a pyrimidine ring, a quinazoline ring, a pyridazine ring, a cinnoline ring, a phthalazine ring, a 1,2,3-, 1,2,4-, or 1,3,5-triazine ring, a carbazole ring, a benzoxazole ring, and an isothiazole ring.

[0056] Among these, a benzene ring, a naphthalene ring, a fluorene ring, a phenanthrene ring, a pyrene ring, a furan ring, a thiophene ring, and a pyridine ring are preferred, a benzene ring, a naphthalene ring, a fluorene ring, and a phenanthrene ring are more preferred, and a benzene ring is even more preferred.

[0057] (R １ In the above formula (1), R １ is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a group represented by the following formula (2a). The substituent is, for example, a halogen atom. The halogen atom is, for example, at least one selected from the group consisting of a fluorine atom, a bromine atom, a chlorine atom, and an iodine atom, and is preferably a fluorine atom.

[0058] R１ The number of carbon atoms in the group is preferably 1 to 20, more preferably 1 to 14, even more preferably 1 to 9, particularly preferably 1 to 6, and most preferably 1 to 3.

[0059] R １ is preferably a linear or branched alkyl group having 1 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms substituted with a halogen atom, or a group represented by formula (2b) described below, more preferably a linear or branched alkyl group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms substituted with a halogen atom, or a group represented by formula (2b), still more preferably a linear alkyl group having 1 to 7 carbon atoms, an alkyl group having 1 to 7 carbon atoms substituted with a halogen atom, or a group represented by formula (2b), and particularly preferably a linear alkyl group having 1 to 4 carbon atoms, an alkyl group having 1 to 4 carbon atoms substituted with a halogen atom, or a group represented by formula (2b).

[0060] (R ２ In the above formula (1), R ２ is a substituted or unsubstituted alkyl group having 2 to 20 carbon atoms, or a group represented by the following formula (2a). The substituent is, for example, a halogen atom. The halogen atom is, for example, at least one selected from the group consisting of a fluorine atom, a bromine atom, a chlorine atom, and an iodine atom, and is preferably a fluorine atom.

[0061] R ２ The number of carbon atoms in the alkyl group is preferably 2 to 20, more preferably 2 to 14, even more preferably 2 to 10, particularly preferably 2 to 7, and most preferably 2 to 4.

[0062] R ２is preferably a linear or branched alkyl group having 2 to 20 carbon atoms, an alkyl group having 2 to 20 carbon atoms substituted with a halogen atom, or a group represented by formula (2b) described below, more preferably a linear or branched alkyl group having 2 to 10 carbon atoms, an alkyl group having 2 to 10 carbon atoms substituted with a halogen atom, or a group represented by formula (2b), still more preferably a linear alkyl group having 2 to 7 carbon atoms, an alkyl group having 2 to 7 carbon atoms substituted with a halogen atom, or a group represented by formula (2b), and particularly preferably a linear alkyl group having 2 to 4 carbon atoms, an alkyl group having 2 to 4 carbon atoms substituted with a halogen atom, or a group represented by formula (2b).

[0063] When the number of carbon atoms is 2 or more, R １ and R ２ may have the same structure or different structures, but from the viewpoint of the solubility of the photochromic composition, R １ and R ２ It is preferable that the structures of the groups are different from each other.

[0064] (Group represented by formula (2a)) -Q １ -(X １ Q ２ ) a-X ２ Q ３ (2a)

[0065] Q １ is an alkylene group or a haloalkylene group, and is a group bonded to atom M at the 13-position in the above formula (1).

[0066] Q １ may be a linear alkylene group or a branched alkylene group. １ is preferably a linear alkylene group.

[0067] Q １ The alkylene group preferably has 1 to 20 carbon atoms, more preferably 1 to 15 carbon atoms, even more preferably 1 to 9 carbon atoms, and particularly preferably 2 to 6 carbon atoms.

[0068] Q １When represents a haloalkylene group, the halogen atom 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 C1 and F, and more preferably F.

[0069] Q ２ is an alkylene group or a haloalkylene group, and the preferred embodiment of the number of carbon atoms and halogen atoms in the alkylene group is １ It is the same as: ２ The number of carbon atoms in the alkylene group is １ The number of carbon atoms in the alkylene group may be the same as or different from that of the alkylene group in the alkylene group.

[0070] Q ３ is an alkyl group or a haloalkyl group, and the number of carbon atoms in the alkyl group is preferably 1 to 20, more preferably 1 to 12, even more preferably 1 to 7, and particularly preferably 1 to 3. ３ may be a linear alkyl group or a branched alkyl group. ３ is preferably a linear alkyl group.

[0071] Q ３ When represents a haloalkyl group, the halogen atom may be at least one selected from the group consisting of I, Cl, Br, and F. The halogen atom is preferably at least one of C1 and F, and more preferably F.

[0072] X １ and X ２ are each independently O, S, or NR ７００ , P.R. ７０１ , or P(=O). X １ and X ２ is O, S, or NR ７００ is preferred, O or S is more preferred, and O is even more preferred.

[0073] R ７００ is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, an aryl group having 5 to 12 carbon atoms, or a heteroaryl group having 3 to 12 carbon atoms. ７００is preferably a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 5 to 12 carbon atoms. Preferred alkyl groups are methyl, ethyl, propyl, butyl, and pentyl groups. Preferred aryl groups are phenyl and naphthyl groups.

[0074] R ７０１ is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, an aryl group having 5 to 12 carbon atoms, or a heteroaryl group having 3 to 12 carbon atoms. ７０１ is preferably a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 5 to 12 carbon atoms. Preferred alkyl groups are methyl, ethyl, propyl, butyl, and pentyl groups. Preferred aryl groups are phenyl and naphthyl groups.

[0075] a is an integer of 0 or more and 10 or less, preferably an integer of 0 or more and 5 or less, more preferably an integer of 0 or more and 3 or less, and particularly preferably an integer of 0 or more and 2 or less.

[0076] The group represented by the formula (2a) can be formed by adding X １ and X ２ is preferably an oxygen atom. １ -(OQ ２ ) a-OQ ３ (2b)

[0077] Specific examples of the group represented by the 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 OCH ３ , -CH ２ CH２ CH ２ SCH ３、 -CH ２ CH ２ OCH ２ CH ２ OCH ３ , -CH ２ CH ２ OCH ２ CH ２ OCH ２ CH ３ , -CH ２ CH ２ OCH ２ CH ２ OCH ２ CH ２ OCH ３ , and -CH ２ CH ２ OCH ２ CH ２ OCH ２ CH ２ OCH ２ CH ２ OCH ３ Examples include:

[0078] (Z １ ) Z １ represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group, and is preferably a substituted or unsubstituted aryl group.

[0079] The aryl group is preferably an aryl group having 5 to 12 carbon atoms. As the aryl group having 5 to 12 carbon atoms, a phenyl group, a 1-naphthyl group, and a 2-naphthyl group are preferred, and a phenyl group is more preferred.

[0080] The substituent of the aryl group is preferably an alkyl group, a haloalkyl group, an alkoxy group, a haloalkoxy group, a substituted amino group, a substituted or unsubstituted heterocyclic group, a halogen atom, a substituted or unsubstituted arylthio group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, more preferably an alkyl group, a haloalkyl group, an alkoxy group, a haloalkoxy group, a substituted amino group, a substituted or unsubstituted heterocyclic group, a halogen atom, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, and even more preferably an alkyl group, a haloalkyl group, a haloalkoxy group, an alkoxy group, a substituted amino group, or a substituted or unsubstituted heterocyclic group. Specific examples of these groups are described below in R ３ The same groups as those exemplified in the above can be used.

[0081] Z １ is preferably a phenyl group having, as a substituent, at least one functional group selected from the group consisting of an alkyl group, a haloalkyl group, an alkoxy group, a haloalkoxy group, a substituted amino group, a substituted or unsubstituted heterocyclic group, a halogen atom, a substituted or unsubstituted arylthio group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group, and more preferably a phenyl group having, as a substituent, at least one functional group selected from the group consisting of an alkyl group, a haloalkyl group, an alkoxy group, a haloalkoxy group, a substituted amino group, and a substituted or unsubstituted heterocyclic group.

[0082] The number of substituents that the aryl group has is preferably 0 or more and 5 or less, more preferably 0 or more and 4 or less, and even more preferably 0 or more and 3 or less.

[0083] Particularly preferred Z １ Examples of the group represented by formula (1) include groups represented by the following formula: In the formula, the carbon atom marked with * represents the carbon atom bonded to the photochromic compound represented by formula (1). In the formula, Me represents a methyl group.

[0084]

[0085] (R ３ ) R ３ is a substituent. ３ is, for example, a hydroxy group, a substituted or unsubstituted alkyl group, a haloalkyl group, a substituted or unsubstituted alkoxy group, a haloalkoxy group, a substituted or unsubstituted cycloalkyl 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 the above formula (2a), a group represented by formula (X) described later, or a group represented by formula (X3) described later.

[0086] b is an integer of 0 or more and 3 or less.

[0087] b is 2 and R ３ When R are bonded to the 5- and 6-positions of the naphthopyran skeleton, the two adjacent R ３ Together they ３ 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. Examples of the substituents on the ring include a hydroxy group, 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 haloalkoxy group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 8 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 groups include R ３ The same groups as those exemplified in the above can be used.

[0088] Suitable rings include rings represented by the following formula (X5).

[0089]

[0090] In the formula (X5), Q and T each independently represent a sulfur atom, a methylene group which may be substituted with an alkyl group having 1 to 10 carbon atoms, an oxygen atom, or NR ３０７ R is a group represented by the formula: ３０７ is a hydrogen atom, a hydroxy group, an alkyl group, a haloalkyl group, an alkoxy group, a haloalkoxy group, a cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a group represented by the above formula (2a). ３ The same groups as those exemplified in the above can be used.

[0091] R ３０５ and R ３０６ are each independently a hydroxy group, an alkyl group, a haloalkyl group, a cycloalkyl group, an alkoxy group, an amino group, a substituted amino group, a substituted or unsubstituted heterocyclic group, a cyano group, a nitro group, a formyl group, a hydroxycarbonyl group, an alkylcarbonyl group, an alkoxycarbonyl group, a halogen atom, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aralkoxy group, a substituted or unsubstituted aryl group, a thiol group, an alkylthio group, an alkoxyalkylthio group, a haloalkylthio group, a cycloalkylthio group, or a substituted or unsubstituted arylthio group. ３ The same groups as those exemplified in the above can be used.

[0092] Also, R ３０５ and R ３０６may 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, particularly preferably 1 to 4 hydrogen atoms, may be substituted with at least one group selected from the group consisting of a hydroxy 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. These specific groups are represented by R ３ In the formula, m is an integer of 1 to 4.

[0093] (Group represented by formula (X))

[0094]

[0095] In the above 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.

[0096] F is an oxygen atom or a sulfur atom, and preferably an oxygen atom.

[0097] G is an oxygen atom, a sulfur atom, or NR ２０２ It is. ２０２ is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, an aryl group having 5 to 12 carbon atoms, or a heteroaryl group having 3 to 12 carbon atoms. G is preferably NH.

[0098] g is 0 or 1.

[0099] R ２０１ is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, an aryl group having 5 to 12 carbon atoms, or a heteroaryl group having 3 to 12 carbon atoms. When G is an oxygen atom or a sulfur atom, R ２０１ is a group other than a hydrogen atom. ２０１is 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.

[0100] Suitable groups of formula (X) are as follows:

[0101]

[0102] (Group represented by formula (X3)) L １ -R ４００ (X3)

[0103] In the above formula (X3), R ４００ is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 5 to 12 carbon atoms, a polymerizable group, a photochromic group, or a silyl group having, as a substituent, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, or an aryl group having 5 to 12 carbon atoms.

[0104] L １ is a group represented by the following formula (X2).

[0105]

[0106] In the above formula (X2), R ３０ is a group represented by the following formula (X2a):

[0107]

[0108] In the formula (X2) and the 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. ３０１ is 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.

[0109] 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 of the group consisting of a COOH group and a COOH group is preferred.

[0110] 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.

[0111] The indeno[2,1-f]naphtho[1,2-b]pyran is preferably a group represented by the following formula (X4):

[0112]

[0113] In the above formula (X4), R ４０１ and R ４０２ is the above-mentioned R ３ The group may be the same as the group used in

[0114] R ４０３ and R ４０４ are each independently the above-mentioned R ３ The group may be the same as the group used in

[0115] R ４０５ and R ４０６ are each independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. ４０５ and R ４０６is R ５ and R ６ The group may be the same as the group used in

[0116] o is an integer of 0 to 4. n is an integer of 0 to 4. When o is an integer of 2 to 4, a plurality of R ４０３ may be the same or different. When n is an integer of 2 or more and 4 or less, a plurality of R ４０４ may be the same or different from each other.

[0117] R ４０１ , R ４０２ , R ４０３ , R ４０４ , and R ４０５ At least one of the substituents on the aryl or heteroaryl group of L １ and combine.

[0118] L is an oxygen atom or a sulfur atom.

[0119] 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.

[0120] R ３０２ , R ３０３ , and R ３０４ are 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.

[0121] h, j, k, and l each independently represent 0 or 1.

[0122] i is an integer of 0 to 200. The structures of groups to which multiple i's are added may be the same or different. i is preferably an integer of 5 to 100, more preferably an integer of 8 to 75, and even more preferably an integer of 10 to 70.

[0123] The dashed line is R４００ Represents a bond with

[0124] Particularly preferred groups represented by the above formula (X2) are represented by the following formula:

[0125]

[0126] (R ３ 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.

[0127] 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.

[0128] The haloalkoxy group is preferably a haloalkoxy group having 1 to 6 carbon atoms. The number of halogen atoms is preferably 1 to 10, and more preferably 2 to 5. The haloalkoxy group having 1 to 6 carbon atoms is preferably an alkoxy group substituted with a fluorine atom, a chlorine atom, or a bromine atom. The haloalkoxy group preferably has a perfluoromethyl group at the terminal. Examples of suitable haloalkoxy groups include a trifluoromethoxy group, a trifluoroethoxy group, a pentafluoroethoxy group, a trifluoropropoxy group, and a heptafluoropropoxy group.

[0129] 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). Examples of substituents that the cycloalkyl group may have 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.

[0130] 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 even more 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.

[0131] The amino group is a primary amino group (-NH ２ ) 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.

[0132] 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, a benzomorpholino group, a benzothiomorpholino group, and a 1,2,3,4-tetrahydroisoquinolino group. The heterocyclic group may have a substituent such as a 2,6-dimethylmorpholino group, a 2,6-dimethylpiperidino group, or a 2,2,6,6-tetramethylpiperidino group. Note that the heterocyclic group may have a substituent, but the number of atoms (3 to 10 atoms) does not include the number of atoms of the substituent. Examples of the substituent 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.

[0133] Examples of halogen atoms include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.

[0134] 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.

[0135] 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. The arylthio group may have a substituent, but the number of carbon atoms in the substituent is not included in the number of carbon atoms (6 to 10 carbon atoms). Examples of the substituent 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.

[0136] 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.

[0137] 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.

[0138] The aralkyl group is preferably an aralkyl group having 7 to 11 carbon atoms. Examples of aralkyl groups having 7 to 11 carbon atoms include a benzyl group, a phenylethyl group, a phenylpropyl group, a phenylbutyl group, and a naphthylmethyl group. The aralkyl group may have a substituent, but the number of carbon atoms (7 to 11 carbon atoms) does not include the number of carbon atoms of the substituent. Examples of the substituent 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.

[0139] The aralkoxy group is preferably an aralkoxy group having 7 to 11 carbon atoms. Examples of aralkoxy groups having 7 to 11 carbon atoms include a benzyloxy group and a naphthylmethoxy group. The aralkoxy group may have a substituent, but the number of carbon atoms (7 to 11 carbon atoms) does not include the number of carbon atoms of the substituent. Examples of the substituent 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.

[0140] The aryloxy group is preferably an aryloxy group having 6 to 12 carbon atoms. Examples of aryloxy groups having 6 to 12 carbon atoms include a phenyloxy group and a naphthyloxy group. The aryloxy group may have a substituent, but the number of carbon atoms (6 to 12 carbon atoms) does not include the number of carbon atoms of the substituent. Examples of the substituent 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.

[0141] The aryl group is not particularly limited, but an aryl group having 5 to 12 carbon atoms is preferred. Examples of the aryl group having 5 to 12 carbon atoms include a phenyl group, a 1-naphthyl group, and a 2-naphthyl group. The aryl group may have a substituent, but the number of carbon atoms (5 to 12 carbon atoms) does not include the number of carbon atoms of the substituent. Examples of the substituent 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.

[0142] The heteroaryl group is not particularly limited, but is preferably a heteroaryl group having 3 to 12 carbon atoms. Examples of heteroatoms include at least one selected from the group consisting of oxygen, sulfur, nitrogen, and phosphorus atoms. The number of heteroatoms in the heteroaryl group is, for example, 1 to 3, preferably 1 or 2. The number of carbon atoms in the 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. The heteroaryl group may have a substituent, but the number of carbon atoms in the substituent (3 to 12 carbon atoms) does not include the number of carbon atoms in the substituent. Examples of the substituent 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.

[0143] 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.

[0144] 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.

[0145] The cycloalkylthio group is preferably a cycloalkylthio group having 3 to 8 carbon atoms. Examples of cycloalkylthio groups 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 (3 to 8 carbon atoms) does not include the number of carbon atoms of the substituent. Examples of the substituent 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.

[0146] 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.

[0147] 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.

[0148] (R ５ and R６ ) R ５ and R ６ are each independently a hydrogen atom or a substituent. ５ and R ６ are preferably each independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group.

[0149] R ５ and R ６ are 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.

[0150] The substituent of the substituted aryl group or the substituted heteroaryl group is preferably a group represented by the above formula (2a), a hydroxy group, an alkyl group, a haloalkyl group, an alkoxy group, a haloalkoxy group, a substituted or unsubstituted cycloalkyl 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 the above formula (X3). The substituent is more preferably an alkyl group, a haloalkyl group, an alkoxy group, a haloalkoxy 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 the above formula (X3).

[0151] These specific groups are R ３ The same groups as those exemplified in the above can be used.

[0152] <Suitable First Photochromic Compound> The first photochromic compound is preferably a photochromic compound represented by the following formula (4): In formula (4), R １ , R ２ , R ３ , R ５ , R ６ , Z １ , M, and b are each defined as in the above formula (1).

[0153]

[0154] (R ４ ) R ４ is a substituent. ４ As for R ３ The same groups as those described in the above can be used.

[0155] c is an integer of 0 to 4. c is preferably 0. When c is an integer of 2 to 4, adjacent R ４ If there is a ４ Together they ４ 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. ４ The combinations are the 9th and 10th positions, the 10th and 11th positions, or the 11th and 12th positions of the naphthopyran skeleton.

[0156] <More Suitable First Photochromic Compound> The first photochromic compound is more preferably a photochromic compound represented by the following formula (5): １ , R ２ , R ３ , R ４ , b, c, and Z １ are the same as those in the above formula (4).

[0157]

[0158] (R ７ and R ８ ) R ７ and R ８are each independently a hydroxy group, a substituted or unsubstituted alkyl group, a haloalkyl group, a substituted or unsubstituted alkoxy group, a haloalkoxy group, a substituted or unsubstituted cycloalkyl 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 the above formula (2a), a group represented by the above formula (X), or a group represented by the above formula (X3). Examples of these specific groups include R ３ and R ４ The same groups as those exemplified in the above can be used.

[0159] d is R ７ and is an integer of 0 to 5. When d is 2 or more, R ７ may be the same or different groups.

[0160] d is an integer of 2 or more and 5 or less, and adjacent R ７ If there is a ７ Together they ７and the carbon atom bonded thereto may form a ring containing at least one atom selected from the group consisting of oxygen atoms, sulfur atoms, carbon atoms, and nitrogen atoms, and the ring may further have a substituent. The ring may simultaneously contain two or more atoms selected from the group consisting of oxygen atoms, sulfur atoms, carbon atoms, and nitrogen atoms. The ring preferably forms a ring represented by the above formula (X5) together with the carbon atom bonded thereto. Examples of the substituent on the ring include a substituent selected from a hydroxy 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.

[0161] e is R ８ and is an integer of 0 to 5. When e is 2 or more, R ８ may be the same or different groups.

[0162] e is an integer of 2 or more and 5 or less, and adjacent R ８ If there is a ８ Together they ８ and the carbon atom bonded thereto may form a ring containing at least one atom selected from the group consisting of oxygen atoms, sulfur atoms, carbon atoms, and nitrogen atoms, and the ring may further have a substituent. The ring may also contain two or more atoms selected from the group consisting of oxygen atoms, sulfur atoms, carbon atoms, and nitrogen atoms simultaneously. The ring preferably forms a ring represented by the above formula (X5) together with the carbon atom bonded thereto. Examples of the substituent on the ring include a substituent selected from a hydroxy 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.

[0163] Specific examples of the first photochromic compound include the following structures: In the formula, Me represents a methyl group.

[0164]

[0165] The first photochromic compound can be synthesized by a known method.

[0166] <Second Photochromic Compound> A suitable photochromic compound to be combined with the first photochromic compound is a second photochromic compound represented by the following formula (2): The second photochromic compound may be used alone or in combination of two or more types.

[0167]

[0168] (M ２ ) M ２ is C, Si, or Ge, with C being preferred.

[0169] (Z ２ and Z ３ ) Z ２ and Z ３ are each independently a hydrogen atom, a hydroxy group, a substituted or unsubstituted alkyl group, a haloalkyl group, a substituted or unsubstituted alkoxy group, a haloalkoxy group, a substituted or unsubstituted cycloalkyl 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 the above formula (2a), a group represented by the above formula (X), or a group represented by the above formula (X3).

[0170] Z ２is preferably a hydrogen atom, a substituted or unsubstituted alkyl group, a haloalkyl group, a substituted or unsubstituted alkoxy group, a haloalkoxy group, a substituted or unsubstituted cycloalkyl 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 cycloalkylthio group, a substituted or unsubstituted silyl group, a substituted or unsubstituted oxysilyl group, a group represented by the above formula (2a), a group represented by the above formula (X), or a group represented by the above formula (X3), and is preferably a hydrogen atom, a substituted or unsubstituted alkyl group, a haloalkyl group, a substituted or unsubstituted is more preferably an unsubstituted alkoxy group, a haloalkoxy 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 silyl group, a substituted or unsubstituted oxysilyl group, a group represented by the above formula (2a), a group represented by the above formula (X), or a group represented by the above 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 haloalkoxy group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryl group, a group represented by the above formula (2a), or a group represented by the above formula (X3).

[0171] Z ３is preferably a hydrogen atom, a substituted or unsubstituted alkyl group, a haloalkyl group, a substituted or unsubstituted alkoxy group, a haloalkoxy group, a substituted or unsubstituted cycloalkyl 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 cycloalkylthio group, a substituted or unsubstituted silyl group, a substituted or unsubstituted oxysilyl group, a group represented by the above formula (2a), a group represented by the above formula (X), or a group represented by the above formula (X3), Z is more preferably an alkyl group, a haloalkyl group, a substituted or unsubstituted alkoxy group, a haloalkoxy 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 silyl group, a substituted or unsubstituted oxysilyl group, a group represented by the above formula (2a), a group represented by the above formula (X), or a group represented by the above formula (X3), and even more preferably a hydrogen atom, a substituted or unsubstituted alkyl group, a haloalkyl group, a haloalkoxy group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted aryl group, a group represented by the above formula (2a), or a group represented by the above formula (X3). ２ and Z ３ Suitable groups of R ３ The same groups as those exemplified in the above can be used.

[0172] (Z ４ ) Z ４is a hydrogen atom, a hydroxy group, a substituted or unsubstituted alkyl group, a haloalkyl group, a substituted or unsubstituted alkoxy group, a haloalkoxy group, a substituted or unsubstituted cycloalkyl 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 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 the above formula (2a), a group represented by the above formula (X), or a group represented by the above formula (X3). Z ４ is R ３ The same groups as those exemplified in the above can be used.

[0173] Z ４is preferably a hydrogen atom, a hydroxy group, a substituted or unsubstituted alkyl group, a haloalkyl group, a substituted or unsubstituted alkoxy group, a haloalkoxy group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted heterocyclic group, a halogen atom, an alkylthio group, a substituted or unsubstituted arylthio 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 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 the above formula (2a), a group represented by the above formula (X), or a group represented by the above formula (X3), A substituted or unsubstituted alkyl group, a haloalkyl group, a substituted or unsubstituted alkoxy group, a haloalkoxy group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted heterocyclic group, a halogen atom, a substituted or unsubstituted arylthio group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted silyl group, a group represented by the above formula (2a), a group represented by the above formula (X), or a group represented by the above formula (X3) is more preferable, a hydrogen atom, a substituted or unsubstituted alkyl group, a haloalkyl group, a substituted or unsubstituted alkoxy group, a haloalkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted aryloxy group, a group represented by the above formula (2a), or a group represented by the above formula (X) is even more preferable.

[0174] (R １２ and R ２２ ) R １２ and R ２２ are each independently a hydrogen atom or a substituent. １２ and R ２２ are preferably each independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a group represented by the above formula (2a).

[0175] R １２and R ２２ The number of carbon atoms in each of the groups is preferably 1 to 20, more preferably 1 to 14, even more preferably 1 to 9, particularly preferably 1 to 6, and extremely preferably 1 to 3.

[0176] R １２ and R ２２ are each independently preferably a linear or branched alkyl group having 1 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms substituted with a halogen atom, or a group represented by the above formula (2b), more preferably a linear or branched alkyl group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms substituted with a halogen atom, or a group represented by the above formula (2b), still more preferably a linear alkyl group having 1 to 7 carbon atoms, an alkyl group having 1 to 7 carbon atoms substituted with a halogen atom, or a group represented by the above formula (2b), and extremely preferably a linear alkyl group having 1 to 4 carbon atoms, an alkyl group having 1 to 4 carbon atoms substituted with a halogen atom, or a group represented by the above formula (2b).

[0177] R １２ and R ２２ may have the same structure or different structures, but from the viewpoint of the solubility of the photochromic composition, it is preferable that they have different structures.

[0178] Also, R １２ and R ２２ may together with the carbon atom to which they are bonded form a substituted or unsubstituted aliphatic ring having 3 to 20 ring carbon atoms, a substituted or unsubstituted fused polycyclic ring in which an aromatic hydrocarbon ring or an aromatic heterocycle is fused to the aliphatic ring, a substituted or unsubstituted heterocycle having 3 to 20 ring atoms, or a substituted or unsubstituted fused polycyclic ring in which an aromatic ring or an aromatic heterocycle is fused to the heterocycle.

[0179] R １２ and R ２２The number of ring carbon atoms in the aliphatic ring formed by these together is preferably 4 to 18, more preferably 5 to 16, and even more preferably 6 to 10. Specific examples of the aliphatic ring include a cyclopentane ring, a cyclohexane ring, a cyclooctane ring, a cycloheptane ring, a norbornane ring, a bicyclononane ring, an adamantane ring, and a spirodicyclohexane ring. The aliphatic ring is preferably a cyclopentane ring, a cyclohexane ring, a cycloheptane ring, a cyclooctane ring, a cyclononane ring, a cyclodecane ring, a cycloundecane ring, a cyclododecane ring, or a spirodicyclohexane ring.

[0180] The number of ring carbon atoms in the fused polycyclic ring is preferably 3 to 20, and more preferably 5 to 10. A specific example of the fused polycyclic ring is a phenanthrene ring.

[0181] The number of ring atoms in the heterocycle is preferably 3 to 20. Specific examples of the heterocycle include a thiophene ring, a furan ring, and a pyridine ring.

[0182] The number of ring atoms in the heterocyclic aromatic ring is preferably 5 to 16. Specific examples of the heterocyclic aromatic ring include a phenylfuran ring and a biphenylthiophene ring.

[0183] These aliphatic rings, fused polycyclic rings, heterocyclic rings, or heteroaromatic rings may have a substituent. Examples of the substituent include at least one substituent selected from the group consisting of 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 haloalkoxy group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, an amino group, an amino group substituted with an alkyl group having 1 to 6 carbon atoms or an aryl group having 5 to 12 carbon atoms, and a halogen atom. The substituent is preferably at least one substituent selected from the group consisting of an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, and a haloalkoxy group having 1 to 6 carbon atoms. The number of substituents is, for example, 0 to 10, preferably 2 to 4.

[0184] The ring may be condensed with a cycloalkyl group having 5 to 7 carbon atoms. Specifically, it is more preferable that the ring shown below is formed.

[0185] R １２ and R ２２ Specifically, the ring formed by combining these rings is more preferably a ring selected from a cyclopentane ring, a cyclohexane ring, a cycloheptane ring, a cyclooctane ring, a cyclononane ring, a cyclodecane ring, a cycloundecane ring, a cyclododecane ring, and a spirodicyclohexane ring. More preferred examples of the group include groups represented by the following formulas. Note that the carbon atom marked with * in the formula is a ring selected from the group consisting of R １２ and R ２２ represents the carbon atom to which the atom is bonded.

[0186]

[0187] (R ３２ and R ４２ ) R ３２ and R ４２ are each independently a substituent. ３２ and R ４２ are each independently, for example, a hydroxy group, a substituted or unsubstituted alkyl group, a haloalkyl group, a substituted or unsubstituted alkoxy group, a haloalkoxy group, a substituted or unsubstituted cycloalkyl 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 the above formula (2a), a group represented by the above formula (X), or a group represented by the above formula (X3). Suitable R ３２ and R ４２ Examples of ３is the same as the group exemplified above.

[0188] b2 is an integer of 0 to 2. When b2 is 2, a plurality of R ３２ may be the same or different from each other.

[0189] c2 is an integer of 0 to 3. When c2 is 2 or 3, a plurality of R ４２ may be the same or different from each other. ４２ If there is a ４２ Together they ４２ 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. ４２ The combination of these is at the 9th and 10th positions of the naphthopyran skeleton.

[0190] R ４２ may form a ring having 5 to 8 atoms, including the carbon atom to which is bonded. Suitable rings include the rings represented by the above formula (X5).

[0191] (R ５２ and R ６２ ) R ５２ and R ６２ are each independently a hydrogen atom or a substituent. ５２ and R ６２ are each preferably independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. ５ and R ６ is the same as the group exemplified above.

[0192] <Suitable Second Photochromic Compound> As the second photochromic compound, a photochromic compound represented by the following formula (6) is preferred.

[0193]

[0194] In the above formula (6), R１２ , R ２２ , R ３２ , R ４２ , R ５２ , R ６２ , Z ２ , Z ３ , Z ４ , c2, and b2 have the same meanings as in the above formula (2).

[0195] <More Suitable Second Photochromic Compound> The second photochromic compound is more preferably a photochromic compound represented by the following formula (7): １２ , R ２２ , R ３２ , R ４２ , b2, c2, Z ２ , Z ３ , and Z ４ are the same as those in the above formula (6).

[0196]

[0197] (R ７２ and R ８２ ) R ７２ and R ８２ are each independently a hydroxy group, a substituted or unsubstituted alkyl group, a haloalkyl group, a substituted or unsubstituted alkoxy group, a haloalkoxy group, a substituted or unsubstituted cycloalkyl 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 the above formula (2a), a group represented by the above formula (X), or a group represented by the above formula (X3). ７２ and R ８２ As for R３ The same groups as those exemplified in the above can be used.

[0198] d2 is R ７２ and is an integer of 0 to 5. When d2 is 2 or more, R ７２ may be the same or different groups.

[0199] d2 is an integer of 2 or more and 5 or less, and adjacent R ７２ If there is a ７２ Together they ７２ and the carbon atom bonded thereto may form a ring containing at least one atom selected from the group consisting of oxygen atoms, sulfur atoms, carbon atoms, and nitrogen atoms, and the ring may further have a substituent. The ring may simultaneously contain two or more atoms selected from the group consisting of oxygen atoms, sulfur atoms, carbon atoms, and nitrogen atoms. The ring preferably forms a ring represented by the above formula (X5) together with the carbon atom bonded thereto. Examples of the substituent on the ring include a substituent selected from a hydroxy 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.

[0200] e2 is R ８２ and is an integer of 0 to 5. When e2 is 2 or more, R ８２ may be the same or different groups.

[0201] e2 is an integer of 2 or more and 5 or less, and adjacent R ８２ If there is a ８２ Together they ８２and the carbon atom bonded thereto may form a ring containing at least one atom selected from the group consisting of oxygen atoms, sulfur atoms, carbon atoms, and nitrogen atoms, and the ring may further have a substituent. The ring may simultaneously contain two or more atoms selected from the group consisting of oxygen atoms, sulfur atoms, carbon atoms, and nitrogen atoms. The ring preferably forms a ring represented by the above formula (X5) together with the carbon atom bonded thereto. Examples of the substituent on the ring include a substituent selected from a hydroxy 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.

[0202] <Particularly Preferred Second Photochromic Compound> From the viewpoint that the yellow coloration of the first photochromic compound before color development can be reduced by the coloration due to thermochromism of the second photochromic compound, and yellowing of the obtained photochromic composition can be further suppressed, the second photochromic compound is particularly preferably represented by the following formula (8): １２ , R ２２ , R ８２ , and e2 have the same meanings as in the above formula (7).

[0203]

[0204] (Z ２Ａ and Z ３Ａ ) Z ２Ａ and Z ３Ａare each independently a hydrogen atom, a substituted or unsubstituted alkyl group, a haloalkyl group, a substituted or unsubstituted alkoxy group, a haloalkoxy group, a substituted or unsubstituted cycloalkyl 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 cycloalkylthio group, a substituted or unsubstituted silyl group, a substituted or unsubstituted oxysilyl group, a group represented by the above formula (2a), a group represented by the above formula (X), or a group represented by the above formula (X3).

[0205] Z ２Ａ is preferably a hydrogen atom, a substituted or unsubstituted alkyl group, a haloalkyl group, a substituted or unsubstituted alkoxy group, a haloalkoxy group, a halogen atom, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryl group, a group represented by the above formula (2a), a group represented by the above formula (X), or a group represented by the above formula (X3).

[0206] Z ３Ａ is preferably a hydrogen atom, a substituted or unsubstituted alkyl group, a haloalkyl group, a substituted or unsubstituted alkoxy group, a haloalkoxy group, a halogen atom, a substituted or unsubstituted arylthio group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted oxysilyl group, a group represented by the above formula (2a), or a group represented by the above formula (X3).

[0207] Z ２Ａ and Z ３Ａ As for R ３ The same groups as those exemplified in the above can be used.

[0208] (Z ４Ａ ) Z ４Ａis a hydrogen atom, a hydroxy group, a substituted or unsubstituted alkyl group, a haloalkyl group, a substituted or unsubstituted alkoxy group, a haloalkoxy group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted heterocyclic group, a halogen atom, an alkylthio group, a substituted or unsubstituted arylthio 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 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 the above formula (2a), a group represented by the above formula (X), or a group represented by the above formula (X3).

[0209] Z ４Ａ is preferably a hydrogen atom, a substituted or unsubstituted alkyl group, a haloalkyl group, a substituted or unsubstituted alkoxy group, a haloalkoxy group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted heterocyclic group, a halogen atom, a substituted or unsubstituted arylthio group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted silyl group, a group represented by the above formula (2a), a group represented by the above formula (X), or a group represented by the above formula (X3), and more preferably a hydrogen atom, a substituted or unsubstituted alkyl group, a haloalkyl group, a substituted or unsubstituted alkoxy group, a haloalkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted aryloxy group, a group represented by the above formula (2a), or a group represented by the above formula (X).

[0210] Z ４Ａ As for R ３ The same groups as those exemplified in the above can be used.

[0211] (R １０２ ) R １０２is a substituted or unsubstituted alkyl group, a haloalkyl group, a substituted or unsubstituted alkoxy group, a haloalkoxy group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted heterocyclic group, a halogen atom, 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 silyl group, a substituted or unsubstituted oxysilyl group, a group represented by the above formula (2a), or a group represented by the above formula (X3).

[0212] R １０２ is preferably a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a haloalkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted heterocyclic group, a halogen atom, a substituted or unsubstituted arylthio group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryl group, or a group represented by the above formula (2a), and more preferably a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryl group, or a group represented by the above formula (2a).

[0213] R １０２ As for R ３ The same groups as those exemplified in the above can be used.

[0214] (R ７２Ａ ) R ７２Ａis a hydroxy group, a substituted or unsubstituted alkyl group, a haloalkyl group, a substituted or unsubstituted alkoxy group, a haloalkoxy group, a substituted or unsubstituted cycloalkyl group, 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 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 the above formula (2a), a group represented by the above formula (X), or a group represented by the above formula (X3). ７２Ａ As for R ３ The same groups as those exemplified in the above can be used.

[0215] d2A is R ７２Ａ and is an integer of 0 to 4. When d2A is 2 or more, R ７２Ａ may be the same or different groups.

[0216] d2A is an integer of 2 or more and 4 or less, and adjacent R ７２Ａ If there is a ７２Ａ Together they ７２Ａand the carbon atom bonded thereto may form a ring containing at least one atom selected from the group consisting of oxygen atoms, sulfur atoms, carbon atoms, and nitrogen atoms, and the ring may further have a substituent. The ring may simultaneously contain two or more atoms selected from the group consisting of oxygen atoms, sulfur atoms, carbon atoms, and nitrogen atoms. The ring preferably forms a ring represented by the above formula (X5) together with the carbon atom bonded thereto. Examples of the substituent on the ring include a substituent selected from a hydroxy 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.

[0217] Specific examples of the second photochromic compound include the following structures: In the formula, Me represents a methyl group.

[0218]

[0219] The second photochromic compound can be synthesized by a known method.

[0220] <Mixing ratio of first photochromic compound to second photochromic compound> The proportion of the first photochromic compound in the total of the first photochromic compound and the second photochromic compound is preferably 10% by mass or more and 95% by mass or less. This proportion is more preferably 15% by mass or more and 90% by mass or less, even more preferably 20% by mass or more and 90% by mass or less, particularly preferably 25% by mass or more and 85% by mass or less, and extremely preferably 30% by mass or more and 80% by mass or less. From the viewpoint of developing a deep color even in an environment where ultraviolet rays are blocked, the proportion of the first photochromic compound is preferably 60% by mass or more, more preferably 70% by mass or more, and even more preferably 80% by mass or more. From the viewpoint of reducing yellow coloration before color development and suppressing yellowing during deterioration, the proportion of the second photochromic compound is preferably 10% by mass or more, more preferably 20% by mass or more, and even more preferably 30% by mass or more.

[0221] <Other Photochromic Compounds> The photochromic composition of the present disclosure may contain other photochromic compounds in addition to the first photochromic compound and the second photochromic compound. The other photochromic compounds include photochromic compounds having structures other than those of the first photochromic compound and the second photochromic compound. Examples of other photochromic compounds include naphthopyran compounds, spirooxazine compounds, benzopyran compounds, spiropyran compounds, fulgide compounds, and diarylethene compounds other than the first photochromic compound and the second photochromic compound. If the photochromic composition contains photochromic compounds other than the first photochromic compound and the second photochromic compound, there is a risk of reduced responsiveness in environments where ultraviolet light is blocked, increased yellowing before color development, and reduced durability. Therefore, it is preferable that the photochromic composition consists only of the first photochromic compound and the second photochromic compound.

[0222] In the photochromic composition of the present disclosure, the content of other photochromic compounds is preferably 35% by mass or less, more preferably 30% by mass or less, even more preferably 20% by mass or less, particularly preferably 10% by mass or less, and extremely preferably 5% by mass or less, the lower limit of which is 0% by mass.

[0223] Among other photochromic compounds, it is preferable to use a chromene compound having an indeno[2,1-f]naphtho[1,2-b]pyran skeleton from the viewpoint of photochromic properties such as color density, initial coloring, durability, and fading rate. In particular, from the viewpoint of obtaining a cured product that is excellent in durability while reducing yellow coloration before color development, the compound may contain one or more third photochromic compounds represented by formula (9) described below, and from the viewpoint of obtaining a cured product that is excellent in responsiveness in an environment where ultraviolet light is blocked and also excellent in fading rate, the compound may contain one or more fourth photochromic compounds represented by formula (11) described below.

[0224] <Third Photochromic Compound> The third photochromic compound is represented by the following formula (9): The third photochromic compound may be used alone or in combination of two or more types.

[0225]

[0226] (R １３ and R ２３ ) R １３ and R ２３ are each independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a group represented by the above formula (2a).

[0227] R １３ and R ２３ The number of carbon atoms in each of the groups is preferably 1 to 20, more preferably 1 to 14, even more preferably 1 to 9, particularly preferably 1 to 6, and extremely preferably 1 to 3.

[0228] R １３ and R ２３ are each independently preferably a linear or branched alkyl group having 1 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms substituted with a halogen atom, or a group represented by the above formula (2b), more preferably a linear or branched alkyl group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms substituted with a halogen atom, or a group represented by the above formula (2b), still more preferably a linear alkyl group having 1 to 7 carbon atoms, an alkyl group having 1 to 7 carbon atoms substituted with a halogen atom, or a group represented by the above formula (2b), and particularly preferably a linear alkyl group having 1 to 4 carbon atoms, an alkyl group having 1 to 4 carbon atoms substituted with a halogen atom, or a group represented by the above formula (2b).

[0229] Also, R １３ and R ２３may together with the carbon atom to which they are bonded form a substituted or unsubstituted aliphatic ring having 3 to 20 ring carbon atoms, a substituted or unsubstituted fused polycyclic ring in which an aromatic hydrocarbon ring or an aromatic heterocycle is fused to the aliphatic ring, a substituted or unsubstituted heterocycle having 3 to 20 ring atoms, or a substituted or unsubstituted fused polycyclic ring in which an aromatic ring or an aromatic heterocycle is fused to the heterocycle.

[0230] R １３ and R ２３ The number of ring carbon atoms in the aliphatic ring formed by these together is preferably 4 to 18, more preferably 5 to 16, and even more preferably 6 to 10. The number of ring carbon atoms in the condensed polycycle is preferably 3 to 20, and more preferably 5 to 10. The number of ring atoms in the heterocycle is preferably 3 to 20. The number of ring atoms in the heterocyclic aromatic ring is preferably 5 to 16.

[0231] R １３ and R ２３ As for R １２ and R ２３ The same groups as those exemplified in the above can be used.

[0232] (Y １ , Y ２ , and Y ３ ) Y １ , Y ２ , and Y ３ are each independently a sulfur atom, a substituted or unsubstituted methylene group, an oxygen atom, or NR ３３ The substituents on the substituted methylene group are preferably halogen atoms, haloalkyl groups having 1 to 3 carbon atoms, or alkyl groups having 1 to 3 carbon atoms, and more preferably fluorine atoms or methyl groups. The number of substituents is preferably 1 or 2.

[0233] R ３３represents a hydrogen atom, a hydroxy group, a substituted or unsubstituted alkyl group, a haloalkyl group, a substituted or unsubstituted alkoxy group, a haloalkoxy group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a group represented by the above formula (2a), and is preferably a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, or a substituted or unsubstituted aryl group.

[0234] b3 is Y ２ and is an integer of 1 to 6, preferably an integer of 1 to 3. When b3 is 2 or more, Y ２ may be the same or different groups.

[0235] (R ４３ ) R ４３ is a hydroxy group, a substituted or unsubstituted alkyl group, a haloalkyl group, a substituted or unsubstituted alkoxy group, a haloalkoxy group, a substituted or unsubstituted cycloalkyl 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 the above formula (2a), a group represented by the above formula (X), or a group represented by the above formula (X3). ４３ As for R ３ The same groups as those exemplified in the above can be used.

[0236] c3 is an integer of 0 to 4. When c3 is an integer of 2 to 4, a plurality of R ４３ may be the same or different from each other. c3 is an integer of 2 or more and 4 or less, and adjacent R ４３If there is a ４３ Together they ４３ 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. It is preferable that these rings together form a ring represented by the above formula (X5). Examples of substituents on the ring include a hydroxy 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. The adjacent R ４３ The combinations are the 9th and 10th positions, the 10th and 11th positions, or the 11th and 12th positions of the naphthopyran skeleton.

[0237] (R ５３ and R ６３ ) R ５３ and R ６３ are each independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. ５ and R ６ The same groups as those exemplified in the above can be used.

[0238] <Suitable Third Photochromic Compound> As the third photochromic compound, a photochromic compound represented by the following formula (10) is preferred. In formula (10), R １３ , R ２３ , R ４３ , Y １ , Y ２ , Y ３ , b3, and c3 have the same meanings as in the above formula (9).

[0239]

[0240] (R ７３ and R ８３ ) R ７３ and R ８３are each independently a hydroxy group, a substituted or unsubstituted alkyl group, a haloalkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted heterocyclic group, a cyano group, a halogen atom, 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 the above formula (2a), a group represented by the above formula (X), or a group represented by the above formula (X3). ７３ and R ８３ As for R ３ The same groups as those exemplified in the above can be used.

[0241] d3 is R ７３ and is an integer of 0 to 5. When d3 is 2 or more, R ７３ may be the same or different groups.

[0242] d3 is an integer of 2 or more and 5 or less, and adjacent R ７３ If there is a ７３ Together they ７３and the carbon atom bonded thereto may form a ring containing at least one atom selected from the group consisting of oxygen atoms, sulfur atoms, carbon atoms, and nitrogen atoms, and the ring may further have a substituent. The ring may simultaneously contain two or more atoms selected from the group consisting of oxygen atoms, sulfur atoms, carbon atoms, and nitrogen atoms. The ring preferably forms a ring represented by the above formula (X5) together with the carbon atom bonded thereto. Examples of the substituent on the ring include a substituent selected from a hydroxy 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.

[0243] e3 is R ８３ and is an integer of 0 to 5. When e3 is 2 or more, R ８３ may be the same or different groups.

[0244] e3 is an integer of 2 or more and 5 or less, and adjacent R ８３ If there is a ８３ Together they ８３ and the carbon atom bonded thereto may form a ring containing at least one atom selected from the group consisting of oxygen atoms, sulfur atoms, carbon atoms, and nitrogen atoms, and the ring may further have a substituent. The ring may simultaneously contain two or more atoms selected from the group consisting of oxygen atoms, sulfur atoms, carbon atoms, and nitrogen atoms. The ring preferably forms a ring represented by the above formula (X5) together with the carbon atom bonded thereto. Examples of the substituent on the ring include a substituent selected from a hydroxy 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.

[0245] Specific examples of the third photochromic compound include the following structures: In the formula, Me represents a methyl group, and Pr represents a propyl group.

[0246]

[0247] The third photochromic compound can be synthesized by a known method.

[0248] The total content of the first photochromic compound, the second photochromic compound, and the third photochromic compound may be 80% by mass or more and 100% by mass or less.

[0249] In a photochromic composition consisting only of the first photochromic compound, the second photochromic compound, and the third photochromic compound, the total content of the first photochromic compound and the second photochromic compound may be 70% by mass or more and 99% by mass or less, and the content of the third photochromic compound may be 1% by mass or more and 30% by mass or less. From the viewpoint of improving durability, the proportion of the third photochromic compound is preferably 10% by mass or more, and more preferably 20% by mass or more, of the total content of the photochromic composition consisting only of the first photochromic compound, the second photochromic compound, and the third photochromic compound.

[0250] <Fourth Photochromic Compound> The fourth photochromic compound is represented by the following formula (11): The fourth photochromic compound may be used alone or in combination of two or more types.

[0251]

[0252] (R １４ and R ２４ ) R １４ and R ２４ together with the carbon atom to which they are bonded, form a substituted or unsubstituted aliphatic ring having 3 to 20 ring carbon atoms, a substituted or unsubstituted fused polycyclic ring in which an aromatic hydrocarbon ring or an aromatic heterocycle is fused to the aliphatic ring, a substituted or unsubstituted heterocycle having 3 to 20 ring atoms, or a substituted or unsubstituted fused polycyclic ring in which an aromatic ring or an aromatic heterocycle is fused to the heterocycle.

[0253] R １４ and R ２４The number of ring carbon atoms in the aliphatic ring formed by these together is preferably 4 to 18, more preferably 5 to 16, and even more preferably 6 to 10. The number of ring carbon atoms in the condensed polycycle is preferably 3 to 20, and more preferably 5 to 10. The number of ring atoms in the heterocycle is preferably 3 to 20. The number of ring atoms in the heterocyclic aromatic ring is preferably 5 to 16.

[0254] R １４ and R ２４ As for R １２ and R ２２ The same groups as those exemplified in the above can be used.

[0255] (R ３４ and R ４４ ) R ３４ and R ４４ are each independently a hydroxy group, a substituted or unsubstituted alkyl group, a haloalkyl group, a substituted or unsubstituted alkoxy group, a haloalkoxy group, a substituted or unsubstituted cycloalkyl 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 the above formula (2a), a group represented by the above formula (X), or a group represented by the above formula (X3). ３４ and R ４４ As for R ３ The same groups as those exemplified in the above can be used.

[0256] b4 is an integer of 0 to 3. When b4 is 2 or 3, a plurality of R ３４ may be the same or different. When b4 is 2, R ３４If there is a ３４ Together they ３４ and the carbon atom to which they are bonded may form a substituted or unsubstituted aliphatic ring, substituted or unsubstituted aliphatic heterocycle, substituted or unsubstituted aromatic ring, or substituted or unsubstituted aromatic heterocycle having 5 to 8 ring atoms. Examples of the substituent on the ring include a substituent selected from a hydroxy 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. Suitable examples of the ring include the ring represented by formula (X5) above.

[0257] c4 is an integer of 0 to 4. When c4 is an integer of 2 to 4, a plurality of R ４４ may be the same or different from each other. c4 is an integer of 2 or more and 4 or less, and adjacent R ４４ If there is a ４４ Together they ４４ 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, or a substituted or unsubstituted aromatic heterocycle having 5 to 8 ring atoms. Suitable rings include the ring represented by the above formula (X5). Examples of substituents on the ring include substituents selected from a hydroxy 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. ４４ The combinations are the 9th and 10th positions, the 10th and 11th positions, or the 11th and 12th positions of the naphthopyran skeleton.

[0258] (R ５４ and R ６４ ) R ５４ and R ６４ are each independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group.５ and R ６ The same groups as those exemplified in the above can be used.

[0259] (Z ５ ) Z ５ is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. ５ As for Z, １ The same groups as those exemplified in the above can be used.

[0260] <Suitable Fourth Photochromic Compound> As the fourth photochromic compound, a photochromic compound represented by the following formula (12) is preferred. In formula (12), R １４ , R ２４ , R ３４ , R ４４ , Z ５ , b4, and c4 have the same meanings as in the above formula (11).

[0261]

[0262] (R ７４ and R ８４ ) R ７４ and R ８４ are each independently a hydroxy group, a substituted or unsubstituted alkyl group, a haloalkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted heterocyclic group, a cyano group, a halogen atom, 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 the above formula (2a), a group represented by the above formula (X), or a group represented by the above formula (X3). ７４ and R ８４ As for R３ The same groups as those exemplified in the above can be used.

[0263] d4 is R ７４ and is an integer of 0 to 5. When d4 is 2 or more, R ７４ may be the same or different groups.

[0264] d4 is an integer of 2 or more and 5 or less, and adjacent R ７４ If there is a ７４ Together they ７４ and a carbon atom bonded to the ring may form a ring containing at least one atom selected from the group consisting of oxygen, sulfur, carbon, and nitrogen atoms, and the ring may have a substituent. The ring may simultaneously contain two or more atoms selected from the group consisting of oxygen, sulfur, carbon, and nitrogen atoms.

[0265] e4 is R ８４ and is an integer of 0 to 5. When e4 is 2 or more, R ８４ may be the same or different groups.

[0266] e4 is an integer of 2 or more and 5 or less, and adjacent R ８４ If there is a ８４ Together they ８４ and a carbon atom bonded to the ring may form a ring containing at least one atom selected from the group consisting of oxygen, sulfur, carbon, and nitrogen atoms, and the ring may have a substituent. The ring may simultaneously contain two or more atoms selected from the group consisting of oxygen, sulfur, carbon, and nitrogen atoms.

[0267] R ７４ and R ８４ 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 ７４ and R ８４Preferably, the ring has 5 to 8 ring atoms, including the carbon atom to which R is bonded, and preferably forms a ring represented by the above formula (X5). The ring may have a substituent. Examples of the substituent include a hydroxy 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 ３ Examples of the groups include the same groups as those exemplified in

[0268] Specific examples of the fourth photochromic compound include the following structures: In the formula, Me represents a methyl group, and Pr represents a propyl group.

[0269]

[0270] The fourth photochromic compound can be synthesized by a known method.

[0271] The total content of the first photochromic compound, the second photochromic compound, and the fourth photochromic compound may be 80% by mass or more and 100% by mass or less.

[0272] In a photochromic composition consisting only of the first photochromic compound, the second photochromic compound, and the fourth photochromic compound, the total content of the first photochromic compound and the second photochromic compound may be 70% by mass or more and 99% by mass or less, and the content of the fourth photochromic compound may be 1% by mass or more and 30% by mass or less. From the viewpoint of obtaining a cured product that is excellent in responsiveness in an environment where ultraviolet light is blocked and also excellent in fading rate, the proportion of the fourth photochromic compound relative to the total content of the photochromic composition consisting only of the first photochromic compound, the second photochromic compound, and the fourth photochromic compound is preferably 10% by mass or more, and more preferably 20% by mass or more.

[0273] The total content of the first photochromic compound, the second photochromic compound, the third photochromic compound, and the fourth photochromic compound may be 95% by mass or more and 100% by mass or less.

[0274] In a photochromic composition consisting only of a first photochromic compound, a second photochromic compound, a third photochromic compound, and a fourth photochromic compound, the total content of the first photochromic compound and the second photochromic compound may be 65% by mass or more and 98% by mass or less, the content of the third photochromic compound may be 1% by mass or more and 30% by mass or less, and the content of the fourth photochromic compound may be 1% by mass or more and 30% by mass or less.

[0275] The mixing ratio of these photochromic compounds can be analyzed, for example, by the following method. First, the photochromic composition is purified by an isolation procedure such as silica gel column chromatography, and the isolated photochromic compound is subjected to proton resonance nuclear magnetic resonance ( １ By performing H-NMR analysis and liquid chromatography mass spectrometry (LC-MS) analysis, the structure of each photochromic compound can be identified, the content can be calculated, and the content ratio of each photochromic compound can be determined.

[0276] When a photochromic composition is contained in a cured product, it can be analyzed, for example, by the following method. First, the cured product is impregnated with an organic solvent to extract the photochromic composition. The extracted photochromic composition is purified by an isolation procedure such as silica gel columnography to isolate two or more photochromic compounds. For each of the isolated photochromic compounds, １ By carrying out H-NMR analysis and LC-MS analysis, the structure of each photochromic compound can be identified, the content can be calculated, and the content ratio of each photochromic compound can be determined.

[0277] <Other Additives> The photochromic composition of the present disclosure may contain other additives as needed, such as organic solvents and polymerizable monomers.

[0278] The organic solvent is not particularly limited as long as it dissolves the photochromic compound, and examples of the organic solvent include acetone, methyl ethyl ketone, methyl isobutyl ketone, diethyl ketone, cyclohexanone, dioxane, toluene, N-methylpyrrolidone, hexane, heptane, ethyl acetate, butyl acetate, dimethylformamide (DMF), dimethyl sulfoxide (DMSO), and tetrahydrofuran (THF).

[0279] As the polymerizable monomer, those described later in relation to the curable composition can be used.

[0280] The curable composition of the present disclosure includes the photochromic composition of the present disclosure and at least one selected from the group consisting of a radically 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 an urea urea polymer.

[0281] The photochromic composition of the present disclosure is preferably used as a photochromic curable composition in combination with a polymerizable compound.

[0282] 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 composition in an amount of 0.001 to 20 parts by mass per 100 parts by mass of the polymerizable compound. The amount of the photochromic composition is more preferably 1 to 10 parts by mass. The optimal amount varies depending on the intended use. For example, the following applies when the photochromic curable composition is used as a thin-film optical article and when it is used as a thick-film optical article.

[0283] (Use as Thin Film Optical Article) For example, when the photochromic curable composition is used to form 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 blend 0.001 parts by mass or more and 20 parts by mass or less of the photochromic composition with respect to 100 parts by mass of the polymerizable monomer.

[0284] (Use as a thick-film optical article) When the photochromic curable composition is used to form a cured body having a thickness of, for example, 1 mm or more, it is preferable to blend 0.001 parts by mass or more and 5 parts by mass or less of the photochromic composition with respect to 100 parts by mass of the polymerizable monomer.

[0285] <Polymerizable Compound> As described above, the photochromic composition is preferably used as a photochromic curable composition in combination with a polymerizable compound. Examples of the polymerizable compound include urethane or urea-based polymerizable compounds capable of forming a urethane bond, a urea bond, etc., compounds having a polymerization reactive group, radical polymerizable compounds, and epoxy-based polymerizable compounds. Among these, the following polymerizable compounds are particularly preferably used.

[0286] <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:

[0287] (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.

[0288] (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; polyfunctional alcohols such as trimethylolpropane and pentaerythritol; and the like.

[0289] (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.).

[0290] 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.

[0291] 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:

[0292] (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, polyethylene glycol di(meth)acrylate, polypropylene glycol di(meth)acrylate, polytetramethylene glycol di(meth)acrylate, polyalkylene glycol di(meth)acrylate, di(meth)acrylates consisting of a random or block structure of multiple polyalkylene glycols, ethylene glycol bisglycidyl (meth)acrylate, neopentyl glycol di(meth)acrylate, bisphenol A di(meth)acrylate, 2,2-bis(4-(meth)acryloyloxyethoxyphenyl)propane, 2,2-bis(3,5-dibromo-4-(meth)acryloyloxyethoxyphenyl)propane, trimethylsilyl acrylate, methyl ... polyfunctional (meth)acrylic acid ester compounds such as trimethylolpropane tri(meth)acrylate, tetramethylolmethane tri(meth)acrylate, tetramethylolmethane tetra(meth)acrylate, trimethylolpropane triethylene glycol tri(meth)acrylate, ditrimethylolpropane tetra(meth)acrylate, and glycerin tri(meth)acrylate; compounds in which the terminals of polyalkylene compounds are modified with (meth)acrylate groups; compounds in which the terminals of polycarbonate compounds are modified with (meth)acrylate groups; compounds in which the terminals of polyester compounds are modified with (meth)acrylate groups; and polyfunctional (meth)acrylate compounds having a urethane bond, such as the reaction product of a polyisocyanate compound having two or more isocyanate groups in the molecule, a polyol compound having two or more hydroxyl groups in the molecule, and a hydroxyl group-containing (meth)acrylate.

[0293] (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.

[0294] (Polyfunctional thio(meth)acrylic acid ester compounds) 1,2-bis(methacryloylthio)ethane, bis(2-acryloylthioethyl)ether, 1,4-bis(methacryloylthiomethyl)benzene.

[0295] (Second Polyfunctional Radically 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.

[0296] 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.

[0297] (Unsaturated carboxylic acids) acrylic acid, methacrylic acid, maleic anhydride.

[0298] ((Meth)acrylic acid esters) Methyl (meth)acrylate, benzyl methacrylate, phenyl methacrylate.

[0299] (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.

[0300] (Fumaric acid esters) Diethyl fumarate, diphenyl fumarate.

[0301] (Thio(meth)acrylic acid) methyl thioacrylate, benzyl thioacrylate, benzyl thiomethacrylate.

[0302] (Vinyl Compounds) Divinylbenzene, styrene, chlorostyrene, methylstyrene, vinylnaphthalene, α-methylstyrene dimer, bromostyrene.

[0303] 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, per 100 parts by mass of the total of the radical polymerizable compounds. More preferably, the amount of the polyfunctional radical polymerizable compound is 90 to 100 parts by mass, and the amount of the monofunctional radical polymerizable compound is 0 to 10 parts by mass. 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 0 to 20 parts by mass, per 100 parts by mass of the total of the radical polymerizable compounds. More preferably, the amount of the first polyfunctional radical polymerizable compound is 85 to 100 parts by mass, 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.

[0304] (Epoxy-based polymerizable compounds) Epoxy-based polymerizable compounds are broadly classified into aliphatic epoxy compounds, alicyclic epoxy compounds, and aromatic epoxy compounds. These may be used alone or in combination.

[0305] (Aliphatic Epoxy Compounds) Examples of the aliphatic epoxy compound include ethylene oxide, 2-ethyloxirane, butyl glycidyl ether, phenyl glycidyl ether, 2,2'-methylenebisoxirane, 1,6-hexanediol diglycidyl ether, ethylene glycol diglycidyl ether, diethylene glycol diglycidyl ether, triethylene glycol diglycidyl ether, tetraethylene glycol diglycidyl ether, nonaethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, dipropylene glycol diglycidyl ether, tripropylene glycol diglycidyl ether, tetrapropylene glycol diglycidyl ether, nonapropylene glycol diglycidyl ether, neopentyl glycol diglycidyl ether, trimethylolpropane triglycidyl ether, glycerol triglycidyl ether, diglycerol tetraglycidyl ether, pentaerythritol tetraglycidyl ether, diglycidyl ether of tris(2-hydroxyethyl)isocyanurate, and triglycidyl ether of tris(2-hydroxyethyl)isocyanurate.

[0306] (Alicyclic Epoxy Compounds) Examples thereof include isophoronediol diglycidyl ether and bis-2,2-hydroxycyclohexylpropane diglycidyl ether.

[0307] (Aromatic Epoxy Compounds) Examples thereof include resorcinol diglycidyl ether, bisphenol A diglycidyl ether, bisphenol F diglycidyl ether, bisphenol S diglycidyl ether, orthophthalic acid diglycidyl ester, phenol novolac polyglycidyl ether, and cresol novolac polyglycidyl ether.

[0308] In addition to the above, epoxy polymerizable compounds having a sulfur atom in the molecule as well as an epoxy group can also be used. Such sulfur atom-containing epoxy polymerizable compounds particularly contribute to improving the refractive index, and include linear aliphatic and cyclic aliphatic compounds, specific examples of which are as follows:

[0309] (Linear aliphatic sulfur atom-containing epoxy polymerizable compounds) bis(2,3-epoxypropyl) sulfide, bis(2,3-epoxypropyl) disulfide, bis(2,3-epoxypropylthio)methane, 1,2-bis(2,3-epoxypropylthio)ethane, 1,2-bis(2,3-epoxypropylthio)propane, 1,3-bis(2,3-epoxypropylthio)propane, 1,3-bis(2,3-epoxypropylthio)-2-methylpropane, 1,4-bis(2,3-epoxypropylthio)butane, 1,4-bis(2,3-epoxypropylthio)-2-methylbutane, 1,3-bis(2,3-epoxypropylthio)butane, 1,5-bis(2,3-epoxypropylthio)pentane, 1,5-bis(2,3-epoxypropylthio)-2-methylpentane, 1,5-bis(2,3-epoxypropylthio)-3-thiapentane, 1,6-bis(2,3-epoxypropylthio)hexane, 1,6-bis(2,3-epoxypropylthio)-2-methylhexane, 3,8-bis(2,3-epoxypropylthio)-3,6-dithiaoctane, 1,2,3-tris(2,3-epoxypropylthio)propane, 2,2-bis(2,3-epoxypropylthio)-1,3-bis(2,3-epoxypropylthiomethyl)propane, 2,2-bis(2,3-epoxypropylthiomethyl)-1-(2,3-epoxypropylthio)butane.

[0310] (Aliphatic sulfur atom-containing epoxy polymerizable compounds) 1,3-bis(2,3-epoxypropylthio)cyclohexane, 1,4-bis(2,3-epoxypropylthio)cyclohexane, 1,3-bis(2,3-epoxypropylthiomethyl)cyclohexane, 1,4-bis(2,3-epoxypropylthiomethyl)cyclohexane, 2,5-bis(2,3-epoxypropylthiomethyl)-1,4-dithiane, 2,5-bis[<2-(2,3-epoxypropylthio)ethyl>thiomethyl]-1,4-dithiane, 2,5-bis(2,3-epoxypropylthiomethyl)-2,5-dimethyl-1,4-dithiane.

[0311] (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 be compounded as polymerization regulators.

[0312] Among the above-mentioned compounding ingredients, ultraviolet stabilizers are preferred because they can improve the durability of the photochromic compound. 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:

[0313] 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. 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.

[0314] In addition to the ultraviolet stabilizer, an ultraviolet absorber can also be used. Examples of the ultraviolet absorber that can be used include known ultraviolet absorbers such as benzophenone-based compounds, benzotriazole-based compounds, cyanoacrylate-based compounds, triazine-based compounds, and benzoate-based compounds, 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.

[0315] <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.

[0316] When a curable composition containing a polymerizable compound is thermally polymerized, the temperature affects the properties of the resulting photochromic cured product.

[0317] 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.

[0318] Furthermore, when photopolymerizing a curable composition, among the polymerization conditions, UV intensity in particular affects the properties of the resulting photochromic cured product. In particular, since the curable composition of the present disclosure contains a first photochromic compound capable of absorbing visible light, it is also affected by the wavelength of the light source used for photopolymerization. The illuminance conditions cannot be generally limited because they are affected by the type and amount of photopolymerization initiator and the type of polymerizable monomer, but the lamp's emission peak wavelength is preferably 365 nm or more, more preferably 385 nm or more, and even more preferably 405 nm or more. The irradiation intensity of the light source lamp is not particularly limited, but is preferably 50 to 1000 mW / cm. ２ It is preferable to select the conditions so that the UV light is irradiated for 20 seconds to 5 minutes.

[0319] [Optical Articles] The photochromic composition of the present disclosure 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.

[0320] The photochromic composition of the present disclosure 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 photochromic lenses, as long as it can provide uniform photochromic performance.

[0321] 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.

[0322] 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).

[0323] 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).

[0324] 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.

[0325] 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.

[0326] 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.

[0327] 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.

[0328] 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.

[0329] 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 view of particularly high adhesion to the optical substrate.

[0330] 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 perform post-processing such as forming a thin film by vapor deposition of a metal oxide such as ZnO, or applying an organic polymer to form a thin film to provide anti-reflection, anti-static treatment, or anti-scratch treatment.

[0331] The present invention will be described in detail using examples and comparative examples, but the present invention is not limited to these examples.

[0332] Examples 1 to 11 and Comparative Examples 1 to 4 First, the photochromic compounds shown in Table 1 were mixed with the following radical polymerizable composition to obtain photochromic curable compositions.

[0333] In Table 1, the amount (parts by mass) of each photochromic compound (chromene compound) blended when the total mass of the radical polymerizable compounds (total mass of the polymerizable composition) is taken as 100 parts by mass is shown by the numerical value in parentheses.

[0334] <Radical Polymerizable Composition> (Polymerizable Compounds) Polyethylene glycol dimethacrylate (average molecular weight 736): 50 parts by mass Diacrylate of polycarbonatediol obtained by phosgenation of pentamethylene glycol and hexamethylene glycol (average molecular weight 620): 15 parts by mass Trimethylolpropane trimethacrylate: 15 parts by mass Dipentaerythritol tetramethacrylate: 15 parts by mass γ-methacryloyloxypropyltrimethoxysilane: 4 parts by mass Glycidyl methacrylate: 1 part by mass (Other Components) Phenylbis(2,4,6-trimethylbenzoyl)phosphine oxide: 0.3 parts by mass Ethylenebis(oxyethylene)bis[3-(5-tert-butyl-4-hydroxy-m-tolyl)propionate]: 1 part by mass Bis(1,2,2,6,6-pentamethyl-4-piperidyl)sebacate: 3 parts by mass

[0335] <Photochromic Compound> (First Photochromic Compound) PC1-1

[0336]

[0337] PC1-2

[0338]

[0339] PC1-3

[0340]

[0341] PC1-4

[0342]

[0343] PC1-5

[0344]

[0345] PC1-6

[0346]

[0347] PC1-7

[0348]

[0349] (Second Photochromic Compound) PC2-1

[0350]

[0351] PC2-2

[0352]

[0353] PC2-3

[0354]

[0355] PC2-4

[0356]

[0357] (Third Photochromic Compound) PC3-1

[0358]

[0359] (Fourth Photochromic Compound) PC4-1

[0360]

[0361] PC4-2

[0362]

[0363] <Synthesis Method> [Synthesis of PC1-1] (Step 1) 23.1 g (50.0 mmol) of a carboxylic acid compound represented by the following formula (1-1-1) synthesized from 3-bromo-4-methoxybenzophenone with reference to the method described in Patent Document 6, 8.6 g (55.0 mmol) of 4-chlorophenylboronic acid, 230 mL of 1,2-dimethoxyethane, 23 mL of ethanol, 11.7 g (110.0 mmol) of sodium carbonate, and 111 mL of water were added and stirred. The mixture was purged with nitrogen under reduced pressure to remove dissolved oxygen, and then 28 mg of tetrakis(triphenylphosphine)palladium(0) was added and the temperature was raised to reflux.

[0364] The reaction was carried out under reflux, and after confirming the consumption of the raw materials, the mixture was cooled to room temperature, and hydrochloric acid was added until the pH of the aqueous layer reached 1. 300 mL of THF and 500 mL of toluene were added, and the mixture was separated. 300 mL of water was added, and washing with water to separate the mixture was repeated three times, after which the solvent was removed from the resulting organic layer. Purification was carried out by reslurrying in 300 mL of methanol, and a carboxylic acid represented by the following formula (1-1-2) was obtained in a yield of 92%.

[0365]

[0366]

[0367] (Step 2) With reference to the method described in Patent Document 7, a compound represented by the following formula (1-1-3) was synthesized from the compound represented by the above formula (1-1-2) in a yield of 75%. To 20.1 g (34.9 mmol) of the obtained compound represented by the following formula (1-1-3) was added 400 mL of toluene, and azeotropic dehydration was carried out until the water content in the toluene reached 126 ppm. After azeotropic dehydration, the mixture was cooled to -20°C, and 26.2 mL of n-BuLi (1.6 M hexane solution) was slowly added while maintaining the temperature at -15°C. After confirming the consumption of the raw materials, 5.2 g (45.0 mmol) of 4-heptanone was slowly added while maintaining the temperature at -10°C or below. The mixture was stirred at -20 to -10°C for 1 hour, and then slowly heated to room temperature. After heating, 400 mL of water was added, and the mixture was separated. Washing with water was repeated until the pH of the aqueous layer reached 7. The solvent in the resulting organic layer was removed, and the residue was purified by silica gel chromatography to obtain a compound represented by the following formula (1-1-4) in a yield of 83%.

[0368]

[0369]

[0370] (Step 3) 16.1 g (28.6 mmol) of the compound represented by the formula (1-1-4), 160 mL of toluene, 3.5 g (40.0 mmol) of morpholine, and 11.0 g (114.4 mmol) of sodium tert-butoxide were added, and the mixture was stirred under reduced pressure to remove dissolved oxygen. ２ (dba) ３0.27 g (0.29 mmol) of methyl methylpropanol and 0.54 g (1.1 mmol) of X-phos were added and heated to 80°C. After the raw materials were consumed, the mixture was cooled to room temperature and filtered. 160 mL of tetrahydrofuran and 10% hydrochloric acid were added to the obtained filtrate, neutralized, and then the layers were separated. The solvent was removed from the obtained organic layer. 300 mL of tetrahydrofuran was dissolved therein, and 5 g of 5% Pd / C (50% water content) was added thereto. The mixture was slightly pressurized with hydrogen gas and reacted for 12 hours. After the reaction, the Pd / C was removed by filtration, and the solvent was removed from the obtained organic layer. The resulting mixture was purified by chromatography on silica gel to obtain a compound represented by the following formula (1-1-5) in a yield of 93%.

[0371]

[0372] (Step 4) To 28.4 g (150.0 mmol) of p-toluenesulfonic acid monohydrate, 750 mL of toluene was added, and azeotropic dehydration was carried out until the water content in the toluene was 300 ppm or less. Thereafter, a toluene solution prepared by dissolving 14.0 g (26.6 mmol) of the compound represented by formula (1-1-5) in 100 mL of toluene was slowly added while maintaining the temperature at 85 to 100°C, and after dropwise addition, the mixture was refluxed.

[0373] After the raw materials were consumed, the mixture was cooled to room temperature, neutralized by adding a 10% aqueous solution of sodium bicarbonate, and then separated. The solvent in the resulting organic layer was removed, and the residue was purified by silica gel chromatography to obtain a compound represented by the following formula (1-1-6) in a yield of 86%.

[0374]

[0375] (Step 5) 2.54 g (5.0 mmol) of the naphthol derivative represented by the above formula (1-1-6) and 2.3 g (6.0 mmol) of propargyl alcohol represented by the following formula (1-1-7) were dissolved in 100 mL of toluene, and 5.0 g of Wakogel C300 was added and stirred for 1 hour 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 residue was purified by silica gel chromatography to obtain PC1-1 in a yield of 73%.

[0376]

[0377] [Synthesis of PC1-2] (Step 1) A compound represented by the following formula (1-2-1) was synthesized by carrying out the same reaction as in the synthesis of PC1-1, except that in Step 2, 1,8-dimethoxy-4-octanone was used instead of 4-heptanone, and in Step 3, benzomorpholine was used instead of morpholine.

[0378]

[0379] (Step 2) 3.15 g (5.0 mmol) of the compound represented by the above formula (1-2-1) and 2.0 g (6.0 mmol) of propargyl alcohol represented by the following formula (1-2-2) were dissolved in 50 mL of toluene, and 0.12 g (0.5 mmol) of pyridinium p-toluenesulfonate was added and stirred at 85°C for 1 hour. After the raw material naphthol derivative was consumed, the mixture was cooled to room temperature, and 40 mL of water was added and the layers were separated. The solvent was removed from the resulting organic layer, and the residue was purified by silica gel chromatography to synthesize PC1-2 in a 76% yield.

[0380]

[0381] [Synthesis of PC1-3] The same reactions as in the synthesis of PC1-1 were carried out except that 3-heptanone was used instead of 4-heptanone in the second step, diphenylamine was used instead of morpholine in the third step, and the compound represented by the following formula (1-3-1) was used instead of the compound represented by the above formula (1-1-7) in the fifth step, to obtain PC1-3 in a yield of 75%.

[0382]

[0383] [Synthesis of PC1-4] PC1-4 was obtained in a yield of 67% by carrying out the same reaction as in the synthesis of PC1-2, except that in the first step of the synthesis of PC1-1, 3-bromo-4-methoxybenzophenone was used instead of 3-bromo-4,4′-dimethoxybenzophenone, and 2-methyl-4-methoxyphenylboronic acid was used instead of 4-chlorophenylboronic acid, in the second step, 8-methoxy-4-octanone was used instead of 4-heptanone, and in the second step of the synthesis of PC1-2, the compound represented by the following formula (1-4-1) was used instead of the compound represented by the above formula (1-2-2).

[0384]

[0385] [Synthesis of PC1-5] The same reactions as in the synthesis of PC1-1 were carried out except that 3-bromo-4-methoxy-4'-methylbenzophenone was used instead of 3-bromo-4-methoxybenzophenone in the first step, 8-fluoro-4-octanone was used instead of 4-heptanone in the second step, and the compound represented by the following formula (1-5-1) was used instead of the compound represented by the above formula (1-1-7) in the fifth step, to obtain PC1-5 in a yield of 66%.

[0386]

[0387] [Synthesis of PC1-6] The same reactions as in the synthesis of PC1-1 were carried out except that diethyl ketone was used instead of 4-heptanone in the second step, N-methylphenylamine was used instead of morpholine in the third step, and the compound represented by the following formula (1-6-1) was used instead of the compound represented by the above formula (1-1-7) in the fifth step, to obtain PC1-6 in a yield of 75%.

[0388]

[0389] [Synthesis of PC1-7] The reactions were carried out in the same manner as in the synthesis of PC1-1, except that in the first step, 3-bromo-4-methoxybenzophenone was replaced with 3-bromo-4-methyl-4'-methoxybenzophenone, and 4-isopropoxyphenylboronic acid was replaced with 4-chlorophenylboronic acid, in the second step, 1,1,1-trifluoro-5-nonanone was replaced with 4-heptanone, and in the fifth step, the compound represented by the following formula (1-7-1) was replaced with the compound represented by the above formula (1-1-7), to obtain PC1-7 in a 70% yield.

[0390]

[0391] [Synthesis of PC2-1] (First Step) In the second step of the synthesis of PC1-1, a compound represented by the following formula (2-1-1), which was synthesized with reference to the method described in Patent Document 7, was used instead of the compound represented by the above formula (1-1-3), and 2-heptanone was used instead of 4-heptanone, to synthesize a compound represented by the following formula (2-1-2).

[0392]

[0393]

[0394] (Second Step) The reaction was carried out in the same manner as in the second step of the synthesis of PC1-2, to obtain PC2-1 in a yield of 67%.

[0395] [Synthesis of PC2-2] (Step 1) The reaction was carried out in the same manner as in the synthesis of PC1-1, except that 4-phenoxy-4'-methoxybenzophenone was used instead of 3-bromo-4-methoxybenzophenone in Step 1 and dibutyl ketone was used instead of 4-heptanone in Step 2, to synthesize a compound represented by the following formula (2-2-1).

[0396]

[0397] (Second Step) In the second synthesis step of PC1-2, the reaction was carried out in the same manner as above, except that the compound represented by the following formula (2-2-2) was used instead of the compound represented by the above formula (1-2-2), to obtain PC2-2 in a yield of 65%.

[0398]

[0399] [Synthesis of PC2-3] A compound represented by the following formula (2-3-1), which was synthesized with reference to the method described in Patent Document 8, was used to carry out a reaction in the same manner as in the fifth step of the synthesis of PC1-1, except that a compound represented by the following formula (2-3-2) was used instead of the compound represented by the above formula (1-1-7), to obtain PC2-3 in a yield of 57%.

[0400]

[0401]

[0402]

[0403] <Evaluation Test> Photochromic laminates were produced using the photochromic curable compositions according to the Examples and Comparative Examples, and their photochromic performance was evaluated.

[0404] (Preparation of Photochromic Laminate) 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 sodium hydroxide solution at 50°C for 5 minutes, and then thoroughly washed with distilled water.

[0405] Using a spin coater (1H-DX2, manufactured by Mikasa Co., Ltd.), 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 that the photochromic coating layer had a thickness of 40 μm.

[0406] 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 ２The 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.

[0407] The obtained photochromic laminate was heated in an oven at 70°C for 15 minutes to return it to a decolorized state, and after cooling to room temperature, it was left under fluorescent light for 1 hour and then shielded from light at 23°C for at least half a day to prepare a pre-coloring sample.

[0408] The photochromic laminate thus obtained was used as a sample to evaluate the photochromic performance and yellowness. The photochromic performance was evaluated by irradiating the sample with a xenon lamp L-2480 (300 W) SHL-100 (beam intensity at the sample lens surface: 365 nm = 2.4 mW / cm) manufactured by Hamamatsu Photonics K.K. ２ , 245nm=24μW / cm ２ The photochromic properties were evaluated by irradiating the sample with a fluorine-containing solution at 23° C. for 300 seconds to develop color.

[0409] (1) Photochromic Performance Evaluation [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 is used as an index of the color tone during color development. [2] Color density at 23°C (A Ｎｏｒｍａｌ

[0033]

[0034] : The difference between the absorbance {ε(300)} after 300 seconds of light irradiation at 23°C and the absorbance ε(0) before light irradiation at the maximum absorption wavelength, and is used as an index of color density. The higher this value, the better the photochromic properties. [3] Color density under UV protection (A ＵＶｃｕｔ[4] 23°C Fading Half-Life [τ1 / 2 (sec.)]: This is the difference between the absorbance {ε(300)} at the maximum absorption wavelength after 300 seconds of light irradiation at 23°C and the absorbance ε(0) without light irradiation. During light irradiation, color development was carried out through a UV cut filter (a laminated glass manufactured by ING Corporation; glass / HP R film / glass was used, capable of blocking 99.8% of light with wavelengths of 380 nm or less). The higher this value, the better the photochromic properties under conditions where UV rays are blocked. [5] 23°C Fading Half-Life [τ1 / 2 (sec.)]: This is the time required for the absorbance at the maximum absorption wavelength of the sample to decrease to half of {ε(300)-ε(0)} when the light irradiation is stopped after 300 seconds of light irradiation at 23°C, and is used as an index of the fading rate. The shorter this time, the faster the fading rate. [6] 23°C Fading Half-Life [τ1 / 2 (sec.)]: This is the time required for the absorbance at the maximum absorption wavelength of the sample to decrease to half of {ε(300)-ε(0)} when the light irradiation is stopped after 300 seconds of light irradiation at 23°C. This is used as an index of the fading rate. The shorter this time, the faster the fading rate. [7] 23°C Fading Half-Life [τ1 / 2 (sec.)]: This is the time required for the absorbance at the maximum absorption wavelength of the sample to decrease to half of {ε(300)-ε(0)} when the light irradiation is stopped. ９０ / A ０ ×100): The obtained photochromic plastic lens was subjected to accelerated deterioration for 90 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 ９０ ) and measure the ratio (A ９０ / A ０ The higher the residual rate, the higher the color durability.

[0410] (2) Yellowness Evaluation [6] Initial Yellowness (YI ０ Initial yellowness (YI): The yellowness of the photochromic laminate before color development was measured using an SM color computer (SM-T) manufactured by Suga Test Instruments Co., Ltd. ０ The smaller the YI (YI) is, the less yellow the photochromic laminate has before color development. [7] Yellowing Degree The YI (YI) of the photochromic plastic lens after 90 hours of accelerated deterioration, obtained in the above [5] Residual Rate, is ９０ ) was measured. Furthermore, the difference (YI ９０ -YI ０ The yellowing index ΔYI was calculated from the above data and the yellowing was evaluated. ９０ -YI ０ ) is smaller, the degree of yellowing of the lens after deterioration is less, and the lens has excellent yellowing resistance.

[0411] The results are shown in Table 2.

[0412]

[0413] Preferred embodiments are described below. [1] A photochromic composition comprising one or more first photochromic compounds represented by the following formula (1) and one or more second photochromic compounds represented by the following formula (2): In the formula (1), M is C, Si, or Ge, ring A is a substituted or unsubstituted aromatic hydrocarbon 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 the ring, and Z １ is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group, R １ is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms or a group represented by the following formula (2a), ２ is a substituted or unsubstituted alkyl group having 2 to 20 carbon atoms, or a group represented by the following formula (2a), 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, and Q ２ is an alkylene group or a haloalkylene group, and Q ３ is an alkyl group or a haloalkyl group, and X 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 an integer of 0 to 10, R ３is a substituent, b is an integer of 0 to 3, R ５ and R ６ are each independently a hydrogen atom or a substituent, In the formula (2), M ２ is C, Si, or Ge, Z ２ and Z ３ are each independently a hydrogen atom, a hydroxy group, a substituted or unsubstituted alkyl group, a haloalkyl group, a substituted or unsubstituted alkoxy group, a haloalkoxy group, a substituted or unsubstituted cycloalkyl 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 the formula (2a) above, a group represented by the following formula (X), or a group represented by the following formula (X3), ４ is a hydrogen atom, a hydroxy group, a substituted or unsubstituted alkyl group, a haloalkyl group, a substituted or unsubstituted alkoxy group, a haloalkoxy group, a substituted or unsubstituted cycloalkyl 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 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 the formula (2a), a group represented by the following formula (X), or a group represented by the following formula (X3), In the formula (X), E is an oxygen atom or NR１０１ 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, and 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): In the formula (X2), R ３０ is a group represented by the following formula (X2a): In the formula (X2) and the formula (X2a), J represents a divalent group, and each J independently represents a direct bond, a substituted or unsubstituted methylene group, an oxygen atom, a sulfur atom, or an 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 １２ and R ２２ are each independently a hydrogen atom or a substituent, R ３２ and R４２ are each independently a substituent, b2 is an integer of 0 or more and 2 or less, c2 is an integer of 0 or more and 3 or less, R ５２ and R ６２ are each independently a hydrogen atom or a substituent.

[0414] [2] In the formula (1), R １ is a linear or branched alkyl group having 1 to 20 carbon atoms, a halogen-substituted alkyl group having 1 to 20 carbon atoms, or a group represented by the following formula (2b): ２ is a linear or branched alkyl group having 2 to 20 carbon atoms, a halogen atom-substituted alkyl group having 2 to 20 carbon atoms, or a group represented by the following formula (2b): １ -(OQ ２ ) a-OQ ３ (2b) In the formula (2b), Q １ , Q ２ , Q ３ and a have the same meanings as in the formula (2a).

[0415] [3] The photochromic composition according to [1] or [2], wherein the first photochromic compound contains a compound represented by the following formula (4): In the formula (4), R １ , R ２ , Z １ , M., R. ５ , and R ６ are the same as those in the formula (1), ３ and R ４each independently represents a hydroxy group, a substituted or unsubstituted alkyl group, a haloalkyl group, a substituted or unsubstituted alkoxy group, a haloalkoxy group, a substituted or unsubstituted cycloalkyl 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), b is an integer of 0 to 3, and c is an integer of 0 to 4, When b is 2 or 3, multiple R ３ may be the same or different, and when c is an integer of 2 or more and 4 or less, a plurality of R ４ may be the same or different, b is 2 or 3, and adjacent R ３ If there is a ３ Together they ３ and a carbon atom bonded to the adjacent 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 the above ring, ４ If there is a ４ Together they ４ 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.

[0416] [4] The photochromic composition according to [3], wherein the first photochromic compound includes a compound represented by the following formula (5): In the formula (5), R １ , R ２ , R ３ , R ４ , b, c, and Z １ are the same as those in the formula (4), ７ and R ８ each independently represents a hydroxy group, a substituted or unsubstituted alkyl group, a haloalkyl group, a substituted or unsubstituted alkoxy group, a haloalkoxy group, a substituted or unsubstituted cycloalkyl 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), d is an integer of 0 or more and 5 or less, and e is an integer of 0 or more and 5 or less, When d is an integer of 2 or more and 5 or less, a plurality of R ７ may be the same or different, and when e is an integer of 2 or more and 5 or less, a plurality of R ８ may be the same or different, d is an integer of 2 or more and 5 or less, and adjacent R ７ If there is a ７ Together they ７and a carbon atom bonded to the adjacent 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 Together they ８ 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.

[0417] [5] In the formula (1), Z １ [5] The photochromic composition according to any one of [1] to [4], wherein is a substituted or unsubstituted phenyl group.

[0418] [6] In the formula (1), Z １ is a phenyl group having, as a substituent, at least one functional group selected from the group consisting of an alkyl group, a haloalkyl group, an alkoxy group, a haloalkoxy group, a substituted amino group, a substituted or unsubstituted heterocyclic group, a halogen atom, a substituted or unsubstituted arylthio group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group.

[0419] [7] The photochromic composition according to any one of [1] to [6], wherein the second photochromic compound includes a compound represented by the following formula (6): In the formula (6), Z ２ , Z ３ , and Z ４ are the same as those in the formula (2), １２ and R ２２ are each independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms or a group represented by the formula (2a), １２and R ２２ may together with the carbon atom to which they are bonded form a substituted or unsubstituted aliphatic ring having 3 to 20 ring carbon atoms, a substituted or unsubstituted fused polycyclic ring in which an aromatic hydrocarbon ring or an aromatic heterocycle is fused to the aliphatic ring, a substituted or unsubstituted heterocycle having 3 to 20 ring atoms, or a substituted or unsubstituted fused polycyclic ring in which an aromatic ring or an aromatic heterocycle is fused to the heterocycle, ３２ and R ４２ each independently represents a hydroxy group, a substituted or unsubstituted alkyl group, a haloalkyl group, a substituted or unsubstituted alkoxy group, a haloalkoxy group, a substituted or unsubstituted cycloalkyl 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), b2 is an integer of 0 or more and 2 or less, and c2 is an integer of 0 or more and 3 or less, When b2 is 2, a plurality of R ３２ may be the same or different from each other, and when c2 is 2 or 3, a plurality of R ４２ may be the same or different, and adjacent R ４２ If there is a ４２ Together they ４２ and R 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, ５２ and R ６２are each independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group.

[0420] [8] The photochromic composition according to [7], wherein the second photochromic compound includes a compound represented by the following formula (7): In the formula (7), R １２ , R ２２ , R ３２ , R ４２ , b2, c2, Z ２ , Z ３ , and Z ４ are the same as those in the formula (6), ７２ and R ８２ each independently represents a hydroxy group, a substituted or unsubstituted alkyl group, a haloalkyl group, a substituted or unsubstituted alkoxy group, a haloalkoxy group, a substituted or unsubstituted cycloalkyl 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), d2 is an integer of 0 or more and 5 or less, and e2 is an integer of 0 or more and 5 or less, When d2 is an integer of 2 or more and 5 or less, a plurality of R ７２ may be the same or different, and when e2 is an integer of 2 or more and 5 or less, a plurality of R ８２ may be the same or different, d2 is an integer of 2 or more and 5 or less, and adjacent R ７２ If there is a ７２ Together they ７２and may form, together with the carbon atom bonded to it, 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, and e2 is an integer of 2 or more and 5 or less, and ８２ If there is a ８２ Together they ８２ 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.

[0421] [9] In the formula (2), Z ２ and Z ３ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group, a haloalkyl group, a substituted or unsubstituted alkoxy group, a haloalkoxy group, a substituted or unsubstituted cycloalkyl 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 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). The photochromic composition according to any one of [1] to [8].

[0422]

[10] The photochromic composition according to [8], wherein the second photochromic compound includes a compound represented by the following formula (8): In the formula (8), R １２ , R ２２ , R ８２ and e2 are the same as those in the formula (7), ２Ａ and Z ３Ａeach independently represents a hydrogen atom, a substituted or unsubstituted alkyl group, a haloalkyl group, a substituted or unsubstituted alkoxy group, a haloalkoxy group, a substituted or unsubstituted cycloalkyl 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 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), Z ４Ａ is a hydrogen atom, a hydroxy group, a substituted or unsubstituted alkyl group, a haloalkyl group, a substituted or unsubstituted alkoxy group, a haloalkoxy group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted heterocyclic group, a halogen atom, an alkylthio group, a substituted or unsubstituted arylthio 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 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), R １０２ is a substituted or unsubstituted alkyl group, a haloalkyl group, a substituted or unsubstituted alkoxy group, a haloalkoxy group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted heterocyclic group, a halogen atom, 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 silyl group, a substituted or unsubstituted oxysilyl group, a group represented by formula (2a) or a group represented by formula (X3), R ７２Ａis a hydroxy group, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, a haloalkoxy group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 8 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 nitro group, a formyl group, a hydroxycarbonyl group, an alkylcarbonyl group, an alkoxy group, a hydroxy ...hydroxy group, a haloalkoxy group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 8 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 nitro group, a formyl group, a hydroxycarbonyl group, an alkylcarbonyl group, an alkoxy group, a hydroxy group, a haloalkoxy group, a hydroxy group, a haloalkoxy group, a haloalkoxy group having 1 to 6 carbon atoms, a haloalkoxy group having 1 to 6 carbon atoms, a haloalkoxy group having 1 to 6 carbon a substituted or unsubstituted cycloalkyl 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 the formula (2a), a group represented by the formula (X), or a group represented by the formula (X3), ７２Ａ may be the same or different groups, and adjacent R ７２Ａ If there is a ７２Ａ Together they ７２Ａ 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.

[0423]

[11] In the formula (1), R １ and R ２ The photochromic composition according to any one of [1] to

[10] , wherein each of the groups has a different structure.

[0424]

[12] The photochromic composition according to any one of [1] to

[11] , wherein the proportion of the first photochromic compound in the total amount of the first photochromic compound and the second photochromic compound is 10% by mass or more and 95% by mass or less.

[0425]

[13] The photochromic composition according to any one of [1] to

[12] , further containing a third photochromic compound represented by the following formula (9): In the formula (9), R １３ and R ２３ are each independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms or a group represented by the formula (2a), １３ and R ２３ may together with the carbon atom to which they are bonded form a substituted or unsubstituted aliphatic ring having 3 to 20 ring carbon atoms, a substituted or unsubstituted fused polycyclic ring in which an aromatic hydrocarbon ring or an aromatic heterocycle is fused to the aliphatic ring, a substituted or unsubstituted heterocycle having 3 to 20 ring atoms, or a substituted or unsubstituted fused polycyclic ring in which an aromatic ring or an aromatic heterocycle is fused to the heterocycle; １ , Y ２ , and Y ３ are each independently a sulfur atom, a substituted or unsubstituted methylene group, an oxygen atom, or NR ３３ and R ３３ represents a hydrogen atom, a hydroxy group, a substituted or unsubstituted alkyl group, a haloalkyl group, a substituted or unsubstituted alkoxy group, a haloalkoxy group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a group represented by the formula (2a), b3 represents an integer of 1 or more and 6 or less, R ４３represents a hydroxy group, a substituted or unsubstituted alkyl group, a haloalkyl group, a substituted or unsubstituted alkoxy group, a haloalkoxy group, a substituted or unsubstituted cycloalkyl 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), c3 is an integer of 0 to 4, and when c3 is an integer of 2 to 4, a plurality of R ４３ may be the same or different, c3 is an integer of 2 or more and 4 or less, and adjacent R ４３ If there is a ４３ Together they ４３ and R 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, ５３ and R ６３ are each independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group.

[0426]

[14] The photochromic composition according to any one of [1] to

[13] , further containing a fourth photochromic compound represented by the following formula (11): In the formula (11), R １４ and R ２４together with the carbon atom to which they are bonded, form a substituted or unsubstituted aliphatic ring having 3 to 20 ring carbon atoms, a substituted or unsubstituted fused polycyclic ring in which an aromatic hydrocarbon ring or an aromatic heterocycle is fused to the aliphatic ring, a substituted or unsubstituted heterocycle having 3 to 20 ring atoms, or a substituted or unsubstituted fused polycyclic ring in which an aromatic ring or an aromatic heterocycle is fused to the heterocycle, ３４ and R ４４ each independently represents a hydroxy group, a substituted or unsubstituted alkyl group, a haloalkyl group, a substituted or unsubstituted alkoxy group, a haloalkoxy group, a substituted or unsubstituted cycloalkyl 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), b3 is an integer of 0 to 3, and c4 is an integer of 0 to 4, When b4 is 2 or 3, a plurality of R ３４ may be the same or different, and when c4 is an integer of 2 or more and 4 or less, a plurality of R ４４ may be the same or different, b4 is 2 or 3, and adjacent R ３４ If there is a ３４ Together they ３４ 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,４４ If there is a ４４ Together they ４４ and R 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, ５４ and R ６４ are each independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group; Z ５ is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group.

[0427]

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

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

[0428]

[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 composition according to any one of [1] to

[14] .

[19] Eyeglasses comprising the lens according to

[18] .

Claims

1. A photochromic composition comprising one or more first photochromic compounds represented by the following formula (1) and one or more second photochromic compounds represented by the following formula (2): In the formula (1), M is C, Si, or Ge, ring A is a substituted or unsubstituted aromatic hydrocarbon 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, Z １ is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group; R １ R is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms or a group represented by the following formula (2a): ２ is a substituted or unsubstituted alkyl group having 2 to 20 carbon atoms, or a group represented by the following formula (2a): 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 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group; a is an integer of 0 to 10; ３ is a substituent, b is an integer of 0 to 3, R ５ and R ６ are each independently a hydrogen atom or a substituent, In the formula (2), M ２ is C, Si, or Ge; Z ２ and Z ３ are each independently a hydrogen atom, a hydroxy group, a substituted or unsubstituted alkyl group, a haloalkyl group, a substituted or unsubstituted alkoxy group, a haloalkoxy group, a substituted or unsubstituted cycloalkyl 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) above, a group represented by formula (X) below, or a group represented by formula (X3) below, ４ is a hydrogen atom, a hydroxy group, a substituted or unsubstituted alkyl group, a haloalkyl group, a substituted or unsubstituted alkoxy group, a haloalkoxy group, a substituted or unsubstituted cycloalkyl 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 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 the formula (2a), a group represented by the following formula (X), or a group represented by the following formula (X3), 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, 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): 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 １２ and R ２２ are each independently a hydrogen atom or a substituent; R ３２ and R ４２ are each independently a substituent, b2 is an integer of 0 or more and 2 or less, c2 is an integer of 0 or more and 3 or less, R ５２ and R ６２ are each independently a hydrogen atom or a substituent.

2. In the formula (1), R １ is a linear or branched alkyl group having 1 to 20 carbon atoms, a halogen-substituted alkyl group having 1 to 20 carbon atoms, or a group represented by the following formula (2b): ２ The photochromic composition according to claim 1, wherein -Q is a linear or branched alkyl group having 2 to 20 carbon atoms, an alkyl group having 2 to 20 carbon atoms substituted with a halogen atom, or a group represented by the following formula (2b): １ - (OQ ２ ) a-OQ ３ (2b) In the formula (2b), Q １ , Q ２ , Q ３ and a have the same meanings as in formula (2a).

3. The photochromic composition according to claim 1, wherein the first photochromic compound comprises a compound represented by the following formula (4): In the formula (4), R １ , R ２ , Z １ , M., R. ５ , and R ６ are the same as those in the formula (1), ３ and R ４ are each independently a hydroxy group, a substituted or unsubstituted alkyl group, a haloalkyl group, a substituted or unsubstituted alkoxy group, a haloalkoxy group, a substituted or unsubstituted cycloalkyl 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 the formula (2a), a group represented by the formula (X), or a group represented by the formula (X3), b is an integer of 0 to 3, and c is an integer of 0 to 4, When b is 2 or 3, multiple R ３ may be the same or different, and when c is an integer of 2 to 4, a plurality of R ４ may be the same or different, b is 2 or 3, and adjacent R ３ If there is a pair of adjacent R ３ Together, they ３ 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 condensed polycycle in which an aromatic ring or an aromatic heterocycle is condensed to the above ring, ４ If there is a pair of adjacent R ４ Together, they ４ 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.

4. The photochromic composition according to claim 3, wherein the first photochromic compound comprises a compound represented by the following formula (5): In the formula (5), R １ , R ２ , R ３ , R ４ , b, c, and Z １ are the same as those in the formula (4), ７ and R ８ are each independently a hydroxy group, a substituted or unsubstituted alkyl group, a haloalkyl group, a substituted or unsubstituted alkoxy group, a haloalkoxy group, a substituted or unsubstituted cycloalkyl 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), d is an integer of 0 to 5, and e is an integer of 0 to 5, When d is an integer of 2 to 5, a plurality of R ７ may be the same or different, and when e is an integer of 2 to 5, a plurality of R ８ may be the same or different, d is an integer of 2 to 5, and adjacent R ７ If there is a pair of adjacent R ７ Together, they 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 condensed polycycle in which an aromatic ring or an aromatic heterocycle is condensed to the above ring, ８ If there is a pair of adjacent R ８ Together, they ８ 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.

5. In the formula (1), Z １ The photochromic composition of claim 1 , wherein is a substituted or unsubstituted phenyl group.

6. In the formula (1), Z １ is a phenyl group having at least one functional group selected from the group consisting of an alkyl group, a haloalkyl group, an alkoxy group, a haloalkoxy group, a substituted amino group, a substituted or unsubstituted heterocyclic group, a halogen atom, a substituted or unsubstituted arylthio group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group, as a substituent.

7. The photochromic composition according to claim 1, wherein the second photochromic compound comprises a compound represented by the following formula (6): In the formula (6), Z ２ , Z ３ , and Z ４ are the same as those in the formula (2), １２ and R ２２ are each independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms or a group represented by the formula (2a), １２ and R ２２ may together with the carbon atom to which they are bonded form a substituted or unsubstituted aliphatic ring having 3 to 20 ring carbon atoms, a substituted or unsubstituted condensed polycyclic ring in which an aromatic hydrocarbon ring or an aromatic heterocycle is condensed to the aliphatic ring, a substituted or unsubstituted heterocycle having 3 to 20 ring atoms, or a substituted or unsubstituted condensed polycyclic ring in which an aromatic ring or an aromatic heterocycle is condensed to the heterocycle; ３２ and R ４２ are each independently a hydroxy group, a substituted or unsubstituted alkyl group, a haloalkyl group, a substituted or unsubstituted alkoxy group, a haloalkoxy group, a substituted or unsubstituted cycloalkyl 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 the formula (2a), a group represented by the formula (X), or a group represented by the formula (X3); b2 is an integer of 0 to 2, and c2 is an integer of 0 to 3, When b2 is 2, a plurality of R ３２ may be the same or different from each other, and when c2 is 2 or 3, a plurality of R ４２ may be the same or different, and adjacent R ４２ If there is a pair of adjacent R ４２ Together, they ４２ and R 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 condensed polycycle in which an aromatic ring or an aromatic heterocycle is condensed to any of these rings, ５２ and R ６２ are each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

8. The photochromic composition according to claim 7, wherein the second photochromic compound comprises a compound represented by the following formula (7): In the formula (7), R １２ , R ２２ , R ３２ , R ４２ , b2, c2, Z ２ , Z ３ , and Z ４ are the same as those in the formula (6), ７２ and R ８２ are each independently a hydroxy group, a substituted or unsubstituted alkyl group, a haloalkyl group, a substituted or unsubstituted alkoxy group, a haloalkoxy group, a substituted or unsubstituted cycloalkyl 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 the formula (2a), a group represented by the formula (X), or a group represented by the formula (X3); d2 is an integer of 0 to 5, and e2 is an integer of 0 to 5, When d2 is an integer of 2 to 5, a plurality of R ７２ may be the same or different, and when e2 is an integer of 2 to 5, a plurality of R ８２ may be the same or different, d2 is an integer of 2 to 5, and adjacent R ７２ If there is a pair of adjacent R ７２ Together, they ７２ and 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 together with the carbon atom bonded to the ８２ If there is a pair of adjacent R ８２ Together, they ８２ 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.

9. In the formula (2), Z ２ and Z ３ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group, a haloalkyl group, a substituted or unsubstituted alkoxy group, a haloalkoxy group, a substituted or unsubstituted cycloalkyl 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 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). The photochromic composition according to claim 1.

10. The photochromic composition according to claim 8, wherein the second photochromic compound comprises a compound represented by the following formula (8): In the formula (8), R １２ , R ２２ , R ８２ and e2 are the same as those in the formula (7), ２Ａ and Z ３Ａ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group, a haloalkyl group, a substituted or unsubstituted alkoxy group, a haloalkoxy group, a substituted or unsubstituted cycloalkyl 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 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); Z ４Ａ is a hydrogen atom, a hydroxy group, a substituted or unsubstituted alkyl group, a haloalkyl group, a substituted or unsubstituted alkoxy group, a haloalkoxy group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted heterocyclic group, a halogen atom, an alkylthio group, a substituted or unsubstituted arylthio 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 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), R １０２ is a substituted or unsubstituted alkyl group, a haloalkyl group, a substituted or unsubstituted alkoxy group, a haloalkoxy group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted heterocyclic group, a halogen atom, 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 silyl group, a substituted or unsubstituted oxysilyl group, a group represented by formula (2a) above, or a group represented by formula (X3) above, R ７２Ａ is a hydroxy group, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, a haloalkoxy group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 8 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 nitro group, a formyl group, a hydroxycarbonyl group, an alkylcarbonyl group, an alkoxy group, a ...cycloalkyl group having 3 to 8 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a cycloalkyl group having 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, 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 the formula (2a), a group represented by the formula (X), or a group represented by the formula (X3), d2A is an integer of 0 or more and 4 or less, and when d2A is an integer of 2 or more and 4 or less, a plurality of R ７２Ａ may be the same or different groups, and adjacent R ７２Ａ If there is a pair of adjacent R ７２Ａ Together, they ７２Ａ 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.

11. In the above formula (1), R １ and R ２ The photochromic composition of claim 1 , wherein each of the has a different structure.

12. The photochromic composition described in claim 1, wherein the proportion of the first photochromic compound in the total value of the first photochromic compound and the second photochromic compound is 10% by mass or more and 95% by mass or less.

13. The photochromic composition according to claim 1, further comprising a third photochromic compound represented by the following formula (9): In the formula (9), R １３ and R ２３ are each independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms or a group represented by the formula (2a), １３ and R ２３ may together with the carbon atom to which they are bonded form a substituted or unsubstituted aliphatic ring having 3 to 20 ring carbon atoms, a substituted or unsubstituted condensed polycyclic ring in which an aromatic hydrocarbon ring or an aromatic heterocycle is condensed to the aliphatic ring, a substituted or unsubstituted heterocycle having 3 to 20 ring atoms, or a substituted or unsubstituted condensed polycyclic ring in which an aromatic ring or an aromatic heterocycle is condensed to the heterocycle; １ , Y ２ , and Y ３ each independently represents a sulfur atom, a substituted or unsubstituted methylene group, an oxygen atom, or NR ３３ And R ３３ is a hydrogen atom, a hydroxy group, a substituted or unsubstituted alkyl group, a haloalkyl group, a substituted or unsubstituted alkoxy group, a haloalkoxy group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a group represented by the formula (2a), b3 is an integer of 1 to 6, ４３ is a hydroxy group, a substituted or unsubstituted alkyl group, a haloalkyl group, a substituted or unsubstituted alkoxy group, a haloalkoxy group, a substituted or unsubstituted cycloalkyl 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 the formula (2a), a group represented by the formula (X), or a group represented by the formula (X3), c3 is an integer of 0 to 4, and when c3 is an integer of 2 to 4, a plurality of R ４３ may be the same or different, c3 is an integer of 2 to 4, and adjacent R ４３ If there is a pair of adjacent R ４３ Together, they ４３ and R 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 condensed polycycle in which an aromatic ring or an aromatic heterocycle is condensed to any of these rings, ５３ and R ６３ are each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

14. The photochromic composition according to claim 1, further comprising a fourth photochromic compound represented by the following formula (11): In the formula (11), R １４ and R ２４ form, together with the carbon atom to which they are bonded, a substituted or unsubstituted aliphatic ring having 3 to 20 ring carbon atoms, a substituted or unsubstituted condensed polycycle in which an aromatic hydrocarbon ring or an aromatic heterocycle is condensed to the aliphatic ring, a substituted or unsubstituted heterocycle having 3 to 20 ring atoms, or a substituted or unsubstituted condensed polycycle in which an aromatic ring or an aromatic heterocycle is condensed to the heterocycle; R ３４ and R ４４ are each independently a hydroxy group, a substituted or unsubstituted alkyl group, a haloalkyl group, a substituted or unsubstituted alkoxy group, a haloalkoxy group, a substituted or unsubstituted cycloalkyl 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 the formula (2a), a group represented by the formula (X), or a group represented by the formula (X3), b3 is an integer of 0 to 3, and c4 is an integer of 0 to 4, When b4 is 2 or 3, a plurality of R ３４ may be the same or different, and when c4 is an integer of 2 to 4, a plurality of R ４４ may be the same or different, b4 is 2 or 3, and adjacent R ３４ If there is a pair of adjacent R ３４ Together, they ３４ and a carbon atom bonded to the R 2 , 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 above ring, ４４ If there is a pair of adjacent R ４４ Together, they ４４ and R 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 condensed polycycle in which an aromatic ring or an aromatic heterocycle is condensed to any of these rings, ５４ and R ６４ are each independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group; Z ５ is a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

15. A curable composition comprising the photochromic composition 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 composition of claim 1.

19. Eyeglasses comprising the lens of claim 18.

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