Compound, composition, cured product, and pattern

Abstract

A compound having at least one structure selected from the group consisting of a structure represented by general formula (I-I) and a structure represented by general formula (I-II), a structure represented by general formula (II), and a structure represented by general formula (III). (X1 and X2 each independently represent a direct bond, C (R101) 2, O, CO, S or NR102, Y1 each independently represents C (R201) 2, O, CO, S, N or NR202, and when Y1 is N, a double bond is formed as shown in a dotted line of formula (II). Other descriptions in the formula refer to the specification. )

Description

Technical Field

[0001] The present invention relates to a compound, composition, and cured product having an oxime sulfonate group. Background Art

[0002] Compounds having an oxime sulfonate group (hereinafter also referred to as "oxime sulfonate compounds") are substances that generate acid upon exposure to energy rays such as light. They are used, for example, as photoacid generators in photolithography resist compositions used in the formation of electronic circuits such as semiconductors, as well as cationic polymerization initiators in photopolymerizable compositions such as resin compositions for photolithography, paints, coatings, adhesives, and inks.

[0003] For example, Patent Document 1 discloses a photoacid generator composed of a sulfone derivative compound having a specific structure that strongly absorbs light of 365 nm wavelength.

[0004] Prior art literature

[0005] Patent Literature

[0006] Patent Document 1: US20150315153A1 Summary of the Invention

[0007] Problems to be solved by the invention

[0008] However, the compound of Patent Document 1 may still have insufficient light absorptivity.

[0009] An object of the present invention is to provide a compound having excellent absorption of light having a wavelength of 365 nm and excellent photodecomposition rate.

[0010] Furthermore, since the compound efficiently decomposes to generate an acid, an excellent curing reaction and a decomposition reaction can be induced in a composition having an acid-reactive component.

[0011] Means for solving problems

[0012] The present inventors have conducted intensive studies and have found that an oxime sulfonate compound having a predetermined structure has excellent absorption of light with a wavelength of 365 nm and also has an excellent photodecomposition rate.

[0013] That is, the present invention relates to the following items.

[0014] [1] A compound having at least one structure selected from the group consisting of the structure represented by the following general formula (II) and the structure represented by the following general formula (I-II), the structure represented by the following general formula (II), and the structure represented by the following general formula (III).

[0015] [Chemical Formula 1]

[0016]

[0017] [Chemical Formula 2]

[0018]

[0019] (Where, X 1 and X 2 Each independently represents a direct bond, C(R 101 )2, O, CO, S or NR 102 ,

[0020] Y 1 Each independently represents C(R 201 )2, O, CO, S, N or NR 202 ,

[0021] Among them, Y 1 When N, a double bond is formed as shown by the dotted line in formula (II).

[0022] Y 2 Each independently represents C(R 201 )2, O, CO, S or NR 202 ,

[0023] R 101 and R 102 each independently represents a hydrogen atom, a halogen atom, a cyano group, an amino group, a hydroxyl group, a nitro group, a carboxyl group, a hydrocarbon group having 1 to 20 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms,

[0024] R 101 and R 102 The hydrocarbon group and heterocyclic group used in the group are groups in which the hydrogen atoms are not substituted, or one or more of the hydrogen atoms are substituted by a halogen atom, a cyano group, a nitro group, a hydroxyl group, a thiol group, -COOH, -SO3H, an isocyanate group or an alkyl group having 1 to 4 carbon atoms, and

[0025] One or more methylene groups in the group may be substituted with a divalent group selected from the following <Group I>,

[0026] R 201 and R 202 are each independently a hydrogen atom, a halogen atom, a cyano group, an amino group, a hydroxyl group, a nitro group, a carboxyl group, a hydrocarbon group having 1 to 20 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms,

[0027] R 201 and R 202 The hydrocarbon group and heterocyclic group used in the group are groups in which the hydrogen atoms are not substituted, or one or more of the hydrogen atoms are substituted by a halogen atom, a cyano group, a nitro group, a hydroxyl group, a thiol group, -COOH, -SO3H, an isocyanate group or an alkyl group having 1 to 4 carbon atoms, and

[0028] One or more methylene groups in the group may be substituted with a divalent group selected from the following <Group I>,

[0029] R 31 represents a hydrocarbon group having 1 to 20 carbon atoms or a heterocyclic group having 2 to 20 carbon atoms,

[0030] R 32 represents a hydrogen atom, a halogen atom, a nitro group, a cyano group, a hydrocarbon group having 1 to 20 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms,

[0031] R 31 and R 32 The hydrocarbon group and heterocyclic group used in the group are groups in which the hydrogen atoms are not substituted, or one or more of the hydrogen atoms are substituted by a halogen atom, a cyano group, a nitro group, a hydroxyl group, a thiol group, -COOH, -SO3H, an isocyanate group or an alkyl group having 1 to 4 carbon atoms, and

[0032] One or more methylene groups in the group may be substituted with a divalent group selected from the following <Group I>,

[0033] n represents 0 or 1,

[0034] *Indicates bonding site.

[0035] Group I: -O-, -COO-, -OCO-, -CO-, -CS-, -S-, -SO-, -SO2-, -NR 33 -、-NR 33 -CO-, -CO-NR 33 -、-NR 33 -COO-, -OCO-NR 33 -or-SiR 33 R 34 -,

[0036] R 33 and R 34 Each independently represents a hydrogen atom, an unsubstituted hydrocarbon group having 1 to 10 carbon atoms, or a heterocyclic group having 2 to 10 carbon atoms.

[0037] The structure represented by formula (II) or the structure represented by formula (I-II) is bonded to the structure represented by formula (II) directly or through a linking group. Furthermore, one or two or more hydrogen atoms in the structures of formula (II), formula (I-II), formula (II) and the linking group may be substituted by groups other than hydrogen atoms.

[0038] [2] The compound according to [1], which is represented by the following general formula (IIA) or (I-II-A).

[0039] [Chemical Formula 3]

[0040]

[0041] (Where, X 1A and X 2A Each independently represents a direct bond, C(R 101A )2, O, CO, S or NR 102A ,

[0042] R 101A and R 102A each independently represents a hydrogen atom, a halogen atom, a cyano group, an amino group, a hydroxyl group, a nitro group, a carboxyl group, a hydrocarbon group having 1 to 20 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms,

[0043] R 101A and R 102A The hydrocarbon group and heterocyclic group used in the group are groups in which the hydrogen atoms are not substituted, or one or more of the hydrogen atoms are substituted by a halogen atom, a cyano group, a nitro group, a hydroxyl group, a thiol group, -COOH, -SO3H, an isocyanate group or an alkyl group having 1 to 4 carbon atoms, and

[0044] One or more methylene groups in the group may be substituted with a divalent group selected from the following <Group I>,

[0045] R 1 、R 2 、R 3 、R 4 、R 9 and R 10 Each independently represents a hydrogen atom, a halogen atom, a cyano group, an amino group, a hydroxyl group, a nitro group, a carboxyl group, a hydrocarbon group having 1 to 20 carbon atoms, a heterocyclic group having 2 to 20 carbon atoms, or a group represented by the following general formula (IV),

[0046] R 5 、R 6 、R 7 、R 8 、R 11 、R 12 、R 13 and R 14 Each independently represents a hydrogen atom, a halogen atom, a cyano group, an amino group, a hydroxyl group, a nitro group, a carboxyl group, a hydrocarbon group having 1 to 20 carbon atoms, a heterocyclic group having 2 to 20 carbon atoms, or a group represented by the following general formula (III-A),

[0047] R 1 、R 2 、R 3 、R 4 、R5 、R 6 、R 7 、R 8 、R 9 、R 10 、R 11 、R 12 、R 13 and R 14 The hydrocarbon group and heterocyclic group used in the group are groups in which the hydrogen atoms are not substituted, or one or more of the hydrogen atoms are substituted by a halogen atom, a cyano group, a nitro group, a hydroxyl group, a thiol group, -COOH, -SO3H, an isocyanate group or an alkyl group having 1 to 4 carbon atoms, and

[0048] One or more methylene groups in the group may be substituted with a divalent group selected from the following <Group I>,

[0049] R 1 、R 2 、R 3 and R 4 At least one of represents a group represented by the following general formula (IV),

[0050] R 5 、R 6 、R 7 and R 8 At least one of them represents a group represented by the following general formula (III-A),

[0051] R 9 and R 10 At least one of represents a group represented by the following general formula (IV),

[0052] R 11 、R 12 、R 13 and R 14 At least one of them represents a group represented by the following general formula (III-A),

[0053] [Chemical Formula 4]

[0054]

[0055] R 31A represents a hydrocarbon group having 1 to 20 carbon atoms or a heterocyclic group having 2 to 20 carbon atoms,

[0056] R 32A represents a hydrogen atom, a halogen atom, a nitro group, a cyano group, a hydrocarbon group having 1 to 20 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms,

[0057] R 31A and R 32AThe hydrocarbon group and heterocyclic ring-containing group used in the group are groups in which the hydrogen atoms in the group are not substituted, or one or more hydrogen atoms in the group are substituted by halogen atoms, cyano groups, nitro groups, hydroxyl groups, thiol groups, -COOH groups, -SO3H groups, isocyanate groups or alkyl groups having 1 to 4 carbon atoms, and

[0058] One or more methylene groups in the group may be substituted with a divalent group selected from the following <Group I>,

[0059] n represents 0 or 1,

[0060] *Indicates the bonding site,

[0061] [Chemical Formula 5]

[0062] *-R 41 -R 42 (IV)

[0063] R 41 Each independently represents a direct bond, a divalent group selected from the following <Group I>, a hydrocarbon group having 1 to 20 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms,

[0064] R 41 The hydrocarbon group and heterocyclic group used in the group are groups in which the hydrogen atoms are not substituted, or one or more of the hydrogen atoms are substituted by a halogen atom, a cyano group, a nitro group, a hydroxyl group, a thiol group, -COOH, -SO3H, an isocyanate group or an alkyl group having 1 to 4 carbon atoms, and

[0065] One or more methylene groups in the group may be substituted with a divalent group selected from the following <Group I>,

[0066] R 42 represents a group represented by any one of the following general formulas (II-A-1), (II-A-2) or (II-A-3),

[0067] *Indicates the bonding site,

[0068] [Chemical Formula 6]

[0069]

[0070] Y 1A 、Y 1A-2 and Y 1A-3 Each independently represents C(R 201A )2, O, CO, S, N or NR 202A ,

[0071] Among them, Y 1A 、Y 1A-2 and Y 1A-3When N is present, a double bond is formed as shown by the dotted line in formula (II), and Y 2A 、Y 2A-2 and Y 2A-3 Each independently represents C(R 201A )2, O, CO, S or NR 202A ,

[0072] R 201A and R 202A each independently represents a hydrogen atom, a halogen atom, a cyano group, an amino group, a hydroxyl group, a nitro group, a carboxyl group, a hydrocarbon group having 1 to 20 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms,

[0073] R 201A and R 202A The hydrocarbon group and heterocyclic group used in the group are groups in which the hydrogen atoms are not substituted, or one or more of the hydrogen atoms are substituted by a halogen atom, a cyano group, a nitro group, a hydroxyl group, a thiol group, -COOH, -SO3H, an isocyanate group or an alkyl group having 1 to 4 carbon atoms, and

[0074] One or more methylene groups in the group may be substituted with a divalent group selected from the following <Group I>,

[0075] R 21 、R 22 、R 23 、R 24 、R 22-2 、R 23-2 、R 24-2 、R 25-2 、R 21-3 、R 23-3 、R 24-3 and R 25-3 each independently represents a hydrogen atom, a halogen atom, a cyano group, an amino group, a hydroxyl group, a nitro group, a carboxyl group, a hydrocarbon group having 1 to 20 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms,

[0076] R 21 、R 22 、R 23 、R 24 、R 22-2 、R 23-2 、R 24-2 、R 25-2 、R 21-3 、R 23-3 、R 24-3 and R 25-3The hydrocarbon group and heterocyclic group used in the group are groups in which the hydrogen atoms are not substituted, or one or more of the hydrogen atoms are substituted by halogen atoms, cyano groups, nitro groups, hydroxyl groups, thiol groups, -COOH groups, -SO3H groups, isocyanate groups or alkyl groups having 1 to 4 carbon atoms, and

[0077] One or more methylene groups in the group may be substituted with a divalent group selected from the following <Group I>,

[0078] * indicates the same as R 41 The bonding site,

[0079] Group I: -O-, -COO-, -OCO-, -CO-, -CS-, -S-, -SO-, -SO2-, -NR 33 -、-NR 33 -CO-, -CO-NR 33 -、-NR 33 -COO-, -OCO-NR 33 -or-SiR 33 R 34 -,

[0080] R 33 and R 34 Each independently represents a hydrogen atom, an unsubstituted hydrocarbon group having 1 to 10 carbon atoms, or an unsubstituted heterocyclic group having 2 to 10 carbon atoms.

[0081] [3] The compound according to [2], wherein the compound is represented by the general formula (IIA), and X 2A For direct bonding.

[0082] [4] The compound according to [2] or [3], wherein X 1A C(R 101A )2, O, S or NR 102A .

[0083] [5] The compound according to any one of [2] to [4], wherein R 41 For direct bonding.

[0084] [6] The compound according to any one of [2] to [5], wherein R 42 It is a group represented by formula (II-A-1).

[0085] [7] The compound according to any one of [2] to [6], wherein R 2 and R 9 is a group represented by formula (IV), wherein R 7 and R 13It is a group represented by formula (III-A).

[0086] [8] The compound according to any one of [2] to [8], wherein R 31A It is an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aralkyl group having 7 to 10 carbon atoms, a 10-camphoryl group, or a group in which one or two or more hydrogen atoms of the alkyl group, the aryl group, the aralkyl group, or the 10-camphoryl group are substituted with halogen atoms.

[0087] [9] The compound according to any one of [2] to [8], wherein R 32A It is a halogenated alkyl group having 1 to 10 carbon atoms.

[0088]

[10] A composition comprising the compound according to any one of [1] to [9] and a resin component.

[0089]

[11] The composition according to

[10] , wherein the resin component is an acid-curable resin component.

[0090]

[12] A cured product of the composition described in

[11] .

[0091]

[13] The composition according to

[10] , wherein the resin component is an acid-decomposable resin component.

[0092]

[14] A pattern comprising the composition described in

[13] .

[0093] Effects of the Invention

[0094] According to the present invention, a compound having excellent absorption of light having a wavelength of 365 nm and excellent photodecomposition rate can be provided. DETAILED DESCRIPTION

[0095] Hereinafter, the compound and composition of the present invention will be described.

[0096] A. Compounds

[0097] First, the compound of the present invention will be described.

[0098] The compound disclosed herein is a compound having at least one structure selected from the structure represented by the following general formula (II) and the structure represented by the following general formula (I-II), a structure represented by the following general formula (II), and a structure represented by the following general formula (III) (hereinafter sometimes referred to as "Compound A").

[0099] [Chemical Formula 7]

[0100]

[0101] In the above general formula, X 1 and X 2 Each independently represents a direct bond, C(R 101 )2, O, CO, S or NR 102 ,

[0102] The above Y 1 Each independently represents C(R 201 )2, O, CO, S, N or NR 202 ,

[0103] Among them, Y 1 When N, a double bond is formed as shown by the dotted line in formula (II).

[0104] The above Y 2 Each independently represents C(R 201 )2, O, CO, S or NR 202 ,

[0105] The above R 101 and R 102 each independently represents a hydrogen atom, a halogen atom, a cyano group, an amino group, a hydroxyl group, a nitro group, a carboxyl group, a hydrocarbon group having 1 to 20 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms,

[0106] The above R 101 and R 102 The hydrocarbon group and heterocyclic ring-containing group used in the group are groups in which the hydrogen atoms in the group are unsubstituted, or one or two or more of the hydrogen atoms are substituted by a halogen atom, a cyano group, a nitro group, a hydroxyl group, a thiol group, -COOH, -SO3H, an isocyanate group, or an alkyl group having 1 to 4 carbon atoms, and one or two or more methylene groups in the group may be substituted by a divalent group selected from the following <Group I>,

[0107] The above R 201 and R 202 each independently represents a hydrogen atom, a halogen atom, a cyano group, an amino group, a hydroxyl group, a nitro group, a carboxyl group, a hydrocarbon group having 1 to 20 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms,

[0108] The above R 201 and R 202 The hydrocarbon group and heterocyclic ring-containing group used in the group are groups in which the hydrogen atoms in the group are unsubstituted, or one or two or more of the hydrogen atoms are substituted by a halogen atom, a cyano group, a nitro group, a hydroxyl group, a thiol group, -COOH, -SO3H, an isocyanate group, or an alkyl group having 1 to 4 carbon atoms, and one or two or more methylene groups in the group may be substituted by a divalent group selected from the following <Group I>,

[0109] The above R 31represents a hydrocarbon group having 1 to 20 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms,

[0110] The above R 32 represents a hydrogen atom, a halogen atom, a nitro group, a cyano group, a hydrocarbon group having 1 to 20 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms,

[0111] The above R 31 and R 32 The hydrocarbon group and heterocyclic ring-containing group used in the group are groups in which the hydrogen atoms in the group are unsubstituted, or one or two or more of the hydrogen atoms are substituted by a halogen atom, a cyano group, a nitro group, a hydroxyl group, a thiol group, -COOH, -SO3H, an isocyanate group, or an alkyl group having 1 to 4 carbon atoms, and one or two or more methylene groups in the group may be substituted by a divalent group selected from the following <Group I>,

[0112] The above n represents 0 or 1,

[0113] *Indicates bonding site.

[0114] Group I: -O-, -COO-, -OCO-, -CO-, -CS-, -S-, -SO-, -SO2-, -NR 33 -、-NR 33 -CO-, -CO-NR 33 -、-NR 33 -COO-, -OCO-NR 33 -or-SiR 33 R 34 -,

[0115] The above R 33 and R 34 Each independently represents a hydrogen atom, an unsubstituted hydrocarbon group having 1 to 10 carbon atoms, or a heterocyclic group having 1 to 10 carbon atoms.

[0116] The structure shown in formula (II) or the structure shown in formula (I-II) and the structure shown in formula (II) are bonded directly or via a linking group by 1 or 2 or more of the hydrogen atoms being separated. The hydrogen atom mentioned here is preferably a hydrogen atom bonded to a carbon atom or a nitrogen atom constituting a ring in formula (II), formula (I-II) and formula (II). Furthermore, 1 or 2 or more hydrogen atoms in formula (II), formula (I-II), formula (II) and the linking group may be substituted by a group other than a hydrogen atom.

[0117] Compound A of the present disclosure has excellent absorption of light with a wavelength of 365 nm and also has an excellent photodecomposition rate.

[0118] By exhibiting the effects as described above, the compound A of the present disclosure can be suitably used as a photoacid generator and a cationic polymerization initiator.

[0119] Hereinafter, Compound A of the present disclosure will be described in detail.

[0120] As described above, the compound of the present disclosure is a compound having at least one structure selected from the structure represented by the following general formula (II) and the structure represented by the following general formula (I-II), the structure represented by the following general formula (II), and the structure represented by the following general formula (III).

[0121] Here, the phrase "having at least one structure selected from the structure represented by the general formula (II) (hereinafter sometimes referred to as Structure II) and the structure represented by the general formula (I-II) (hereinafter sometimes referred to as Structure I-II), the structure represented by the general formula (II) (hereinafter sometimes referred to as Structure II), and the structure represented by the general formula (III) (hereinafter sometimes referred to as Structure III) means that at least one structure selected from Structure II and Structure I-II, Structure II, and Structure III are contained in the same molecule.

[0122] In addition, at least one structure selected from Structure II and Structure I-II, Structure II and Structure III can be directly covalently bonded as exemplified by the following compound (Compound No. 1), or can be covalently bonded via a linking group as exemplified by the following compound (Compound No. 4).

[0123] The above structure II or structure I-II and structure II are structures in which one or more hydrogen atoms in the structure are separated and covalently bonded directly or via a linking group. Structure III is further bonded to the structure II or structure I-II bonded to structure II.

[0124] The combination of at least one structure selected from the Structure II and Structure I-II, the bonding of Structure II and Structure III can be a combination of any bonding selected from the bonding of Structure II and Structure I-II, the bonding of Structure II and Structure II, the bonding of Structure I-II and Structure II, the bonding of Structure II and Structure III, the bonding of Structure I-II and Structure III, and the bonding of Structure II and Structure III, or can include the bonding of Structure II, the bonding of Structure I-II, the bonding of Structure II, and the bonding of Structure III. The compounds of the present disclosure are covalently bonded directly or via a linking group by a combination of any of the above bondings in a manner including at least one structure (hereinafter, also referred to as "Structure I") selected from Structure II and Structure I-II, at least one Structure II, and at least one Structure III. Hereinafter, it is also referred to as "the Structure I, Structure II, and Structure III are covalently bonded directly or via a linking group."

[0125] The compound A may have two or more of each structure as exemplified by the following compounds (Compound No. 30, No. 31).

[0126] When the above structures are covalently bonded via a linking group, the linking group is a group having a structure other than the above-mentioned Structure II, Structure I-II, Structure II, and Structure III, and examples thereof include a divalent group selected from the following <Group I>, a hydrocarbon group having 1 to 20 carbon atoms, and a heterocyclic group having 2 to 20 carbon atoms.

[0127] The hydrocarbon group and heterocyclic ring-containing group are groups in which the hydrogen atoms in the group are unsubstituted, or one or two or more of the hydrogen atoms are substituted by a halogen atom, a cyano group, a nitro group, a hydroxyl group, a thiol group, -COOH, -SO3H, an isocyanate group, or an alkyl group having 1 to 4 carbon atoms, and one or two or more methylene groups in the group may be substituted by a divalent group selected from the following <Group I>.

[0128] Group I: -O-, -COO-, -OCO-, -CO-, -CS-, -S-, -SO-, -SO2-, -NR 33 -、-NR 33 -CO-, -CO-NR 33 -、-NR 33 -COO-, -OCO-NR 33 -or-SiR 33 R 34 -,

[0129] R 33 and R 34 Each independently represents a hydrogen atom, an unsubstituted hydrocarbon group having 1 to 10 carbon atoms, or an unsubstituted heterocyclic group having 1 to 10 carbon atoms.

[0130] The above-mentioned Structure II, any one or both of Structures I-II, and Structure II and the linking group (hereinafter also referred to as "Structures I and II, etc.". As described above, any one of them is bonded to the general formula (III).) may have one or more hydrogen atoms in the structure substituted with a substituent.

[0131] Examples of the substituent include a halogen atom, a cyano group, a nitro group, a hydroxyl group, a thiol group, -COOH, -SO3H, an isocyanate group, a hydrocarbon group having 1 to 20 carbon atoms, and a heterocyclic group having 2 to 20 carbon atoms. In some cases, the hydrogen atoms in the hydrocarbon group and the heterocyclic group are unsubstituted, and one or more methylene groups in the group are substituted with a divalent group selected from the group I. In this specification, a group other than a hydrogen atom that replaces a hydrogen atom may be referred to as a "substituent."

[0132] It should be noted that, in this disclosure, the number of carbon atoms in a group, when a hydrogen atom in the group is replaced by a substituent, refers to the number of carbon atoms in the group after the replacement. For example, the "carbon number 1 to 20" in "a substituted hydrocarbon group having 1 to 20 carbon atoms" refers to the number of carbon atoms in the entire group after the hydrogen atoms are replaced, not the number of carbon atoms in the hydrocarbon group before the hydrogen atoms are replaced.

[0133] In addition, in this disclosure, the number of carbon atoms in a group having a specified number of carbon atoms, where a methylene group in a group having a specified number of carbon atoms is substituted with a divalent group selected from the above-mentioned <Group I>, is defined as the number of carbon atoms in the group after the substitution. For example, in this specification, the number of carbon atoms in a group where one of the methylene groups (-CH2-) in an alkyl group having 20 carbon atoms is substituted with a divalent group "-O-" is 19.

[0134] Furthermore, a group in which one or more methylene groups in a hydrocarbon group are substituted with a divalent group selected from the aforementioned <Group I> does not have a structure in which multiple divalent groups are adjacent. Furthermore, a structure in which all hydrocarbon groups are substituted with groups selected from <Group I> does not exist. For example, -CO- is not a hydrocarbon group having 1 carbon atom (a group in which a methylene group is substituted with a divalent group selected from <Group I>), but rather is a divalent group selected from <Group I> itself. It should be noted that the multiple divalent groups selected from <Group I> may be the same or different.

[0135] As the unsubstituted hydrocarbon group having 1 to 20 carbon atoms used as a substituent to replace the hydrogen atoms in the above structures I and II, there can be mentioned an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a cycloalkylalkyl group having 4 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an arylalkyl group having 7 to 20 carbon atoms.

[0136] The alkyl group having 1 to 20 carbon atoms may be linear or branched. Examples of linear alkyl groups include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, and octadecyl. Examples of branched alkyl groups include isopropyl, sec-butyl, tert-butyl, isobutyl, isopentyl, tert-pentyl, 2-hexyl, 3-hexyl, 2-heptyl, 3-heptyl, isoheptyl, tert-heptyl, isooctyl, tert-octyl, 2-ethylhexyl, nonyl, isononyl, decyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, and octadecyl.

[0137] Examples of the cycloalkyl group having 3 to 20 carbon atoms include saturated monocyclic alkyl groups, saturated polycyclic alkyl groups, and groups in which one or more hydrogen atoms in the ring of these groups are replaced by an alkyl group. Examples of the saturated monocyclic alkyl group include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, and cyclodecyl. Examples of the saturated polycyclic alkyl group include adamantyl, decahydronaphthyl, octahydropentalenyl, and bicyclo[1.1.1]pentanyl. Examples of the alkyl group in which a hydrogen atom in the ring of a saturated monocyclic or saturated polycyclic alkyl group is replaced include the groups exemplified above as the alkyl group. Examples of the group in which one or more hydrogen atoms in the ring of a saturated polycyclic alkyl group is replaced by an alkyl group include bornyl.

[0138] The cycloalkylalkyl group having 4 to 20 carbon atoms is a group in which one or more hydrogen atoms of an alkyl group are replaced by a cycloalkyl group. The cycloalkyl group in the cycloalkylalkyl group may be monocyclic or polycyclic. Examples of cycloalkylalkyl groups in which the cycloalkyl group is monocyclic include cyclopropylmethyl, 2-cyclobutylethyl, 3-cyclopentylpropyl, 4-cyclohexylbutyl, cycloheptylmethyl, cyclooctylmethyl, 2-cyclononylethyl, and 2-cyclodecylethyl. Examples of cycloalkylalkyl groups in which the cycloalkyl group is polycyclic include 3-3-adamantylpropyl and decahydronaphthylpropyl.

[0139] The alkenyl group having 2 to 20 carbon atoms is an internal alkenyl group having an unsaturated bond. It may be straight-chain or branched. Examples of the internal alkenyl group include vinyl, 1-propenyl, 2-butenyl, 3-pentenyl, 2-hexenyl, 3-hexenyl, 2-heptenyl, 3-heptenyl, 4-heptenyl, 3-octenyl, 3-nonenyl, 4-decenyl, 3-undecenyl, 4-dodecenyl, and 4,8,12-tetradecatrienylallyl.

[0140] The aryl group having 6 to 20 carbon atoms may have a monocyclic structure, a condensed ring structure, or a group in which two aromatic hydrocarbon rings are linked together.

[0141] The aryl group formed by linking two aromatic hydrocarbon rings may be a group formed by linking two monocyclic aromatic hydrocarbon rings, a group formed by linking a monocyclic aromatic hydrocarbon ring and a condensed aromatic hydrocarbon ring, or a group formed by linking two condensed aromatic hydrocarbon rings. Examples of the linking group linking the two aromatic hydrocarbon rings include a single bond and a carbonyl group.

[0142] Examples of the aryl group with a monocyclic structure include phenyl, tolyl, xylyl, ethylphenyl, and 2,4,6-trimethylphenyl. Examples of the aryl group with a condensed ring structure include naphthyl, anthracenyl, phenanthrenyl, and pyrenyl. Examples of the aryl group with two linked aromatic hydrocarbon rings include biphenyl and benzoylphenyl.

[0143] Furthermore, condensed rings containing an aromatic hydrocarbon ring, such as fluorenyl and indenyl, are also included in the aryl group.

[0144] The aralkyl group having 7 to 20 carbon atoms is a group in which one or more hydrogen atoms in an alkyl group are replaced by an aryl group. Examples of the aralkyl group include benzyl, 9-fluorenylmethyl, A-methylbenzyl, phenethyl, and naphthylpropyl.

[0145] The heterocyclic group having 2 to 20 carbon atoms used as a substituent for replacing a hydrogen atom in the above structures I and II, etc., may be any group as long as it has 2 to 20 carbon atoms. Examples of the heterocyclic group include a group obtained by removing one hydrogen atom from an unsubstituted heterocyclic compound (hereinafter sometimes referred to as "heterocyclic group I"), a group obtained by replacing one or more hydrogen atoms in the above heterocyclic group I with a hydrocarbon group (hereinafter sometimes referred to as "heterocyclic group II"), or a group having a structure in which one or more hydrogen atoms in the above unsubstituted heterocyclic group I or heterocyclic group II are replaced with a substituent.

[0146] As the hydrocarbon group replacing the hydrogen atom in the heterocyclic group I, a hydrocarbon group having 1 to 20 carbon atoms, which satisfies the specified number of atoms specified for the heterocyclic ring-containing group, can be used as the substituent replacing the hydrogen atom in the above structures I and II.

[0147] When the heterocyclic group II has a substituent, the substituent may be bonded to either the heterocyclic group or the hydrocarbon group.

[0148] The heterocyclic compound (hereinafter sometimes referred to as "heterocycle") may have a monocyclic structure or a condensed ring structure. A condensed ring heterocycle is a structure in which a heterocycle is condensed with a heterocycle or a hydrocarbon ring, and examples thereof include condensed rings containing a heterocycle.

[0149] Specific examples of the heterocyclic ring include monocyclic heterocyclic rings such as a thiophene ring, a furan ring, a pyrrole ring, a pyrrolidine ring, a pyridine ring, a piperidine ring, a piperazine ring, a morpholine ring, a thiomorpholine ring, a homopiperidine ring, a homopiperazine ring, a tetrahydropyridine ring, a tetrahydrofuran ring, a tetrahydropyran ring, a caprolactam ring, an isocyanuric acid ring, and a hydantoin ring; and polycyclic heterocyclic rings such as a tetrahydroquinoline ring, a tetrahydroisoquinoline ring, a dihydrobenzofuran ring, a tetrahydrocarbazole ring, a benzothiazole ring, a benzoxazole ring, a benzimidazole ring, an indole ring, and an indene ring.

[0150] As the above R 101 and R 102 The unsubstituted hydrocarbon group having 1 to 20 carbon atoms used in the above structures I and II can be any of the hydrocarbon groups listed as substituents for hydrogen atoms, as long as the substituents satisfy the specified number of carbon atoms.

[0151] As the above R 101 and R 102 The unsubstituted heterocyclic group having 1 to 20 carbon atoms used in the above structures I and II can be any of the heterocyclic groups listed as substituents for hydrogen atoms, as long as the substituents satisfy the specified number of carbon atoms.

[0152] As the above R 201 and R 202 The unsubstituted hydrocarbon group having 1 to 20 carbon atoms used in the above structures I and II can be any of the hydrocarbon groups listed as substituents for hydrogen atoms, as long as the substituents satisfy the specified number of carbon atoms.

[0153] As the above R 201 and R 202 The unsubstituted heterocyclic group having 1 to 20 carbon atoms used in the above structures I and II can be any of the heterocyclic groups listed as substituents for hydrogen atoms, as long as the substituents satisfy the specified number of carbon atoms.

[0154] The above R 101 、R 102 、R 201 and R 202 and R 101A 、R 102A 、R 201A and R 202A The number of carbon atoms in each independently may be 10 or less, or 5 or less.

[0155] As the above R 31 and R 32 The unsubstituted hydrocarbon group having 1 to 20 carbon atoms used in the above structures I and II can be any of the hydrocarbon groups listed as substituents for hydrogen atoms, as long as the substituents satisfy the specified number of carbon atoms.

[0156] As the above R 31 and R 32 The unsubstituted heterocyclic group having 1 to 20 carbon atoms used in the above structures I and II can be any of the heterocyclic groups listed as substituents for hydrogen atoms, as long as the substituents satisfy the specified number of carbon atoms.

[0157] The above R 31 , and R described later 31A The number of carbon atoms in each independently may be 15 or less, 12 or less, 10 or less, 8 or less, or 5 or less.

[0158] The above R 32 and R32A The number of carbon atoms in each of the above may be independently 10 or less, 5 or less, or 3 or less.

[0159] In the above <Group I>, as R 33 and R 34 The unsubstituted hydrocarbon group having 1 to 10 carbon atoms used in the above structures I and II can be any of the hydrocarbon groups listed as substituents for hydrogen atoms, as long as the substituents satisfy the specified number of carbon atoms.

[0160] In the above <Group I>, as R 33 and R 34 The unsubstituted heterocyclic group having 2 to 10 carbon atoms used in the above structures I and II can be any of the heterocyclic groups listed as substituents for hydrogen atoms, as long as the substituents satisfy the specified number of carbon atoms.

[0161] The above R 33 、R 34 and R 33A 、R 34A The number of carbon atoms in each of the above may be independently 10 or less, or 5 or less.

[0162] When the above structures I and II, I and III, and / or II and III are covalently bonded via a linking group, as the hydrocarbon group having 1 to 20 carbon atoms used in the linking group, a divalent group obtained by removing one hydrogen atom from the hydrocarbon groups listed as substituents for hydrogen atoms in the above structures I and II, etc. can be used.

[0163] When the above structures I and II, I and III, and / or II and III are covalently bonded via a linking group, as the heterocyclic group having 2 to 20 carbon atoms used in the linking group, a divalent group obtained by removing one hydrogen atom from the heterocyclic group listed as a substituent for a hydrogen atom in the above structures I and II, etc. can be used.

[0164] In the present disclosure, when Compound A is at least one selected from Structure II and Structure I-II, and has one structure each of Structure II and Structure III, Compound A is preferably a structure in which Structure II and Structure III are bonded to Structure II or Structure I-II, either directly or via a linker. More preferably, Compound A is a structure in which Structure II and Structure III are directly bonded to Structure II or Structure I-II, respectively. This is because Compound A exhibits excellent absorption of light at a wavelength of 365 nm and excellent photodecomposition efficiency.

[0165] In compound A, the number of structures selected from structure II and structure I-II may be 1 or more and 5 or less, 1 or more and 2 or less, or 1 or less.

[0166] The number of structures II may be 1 or more and 5 or less, 1 or more and 2 or less, or 1 or less.

[0167] The number of Structure III may be 1 or more and 5 or less, 1 or more and 2 or less, or 1 or less.

[0168] In this disclosure, X 1 Preferably C(R 101 )2, O, S or NR 102 , wherein C(R 101 )2, O or NR 102 , particularly preferably NR 102 .

[0169] This is because through X 1 Compound A having the above structure has readily available raw materials and is easy to synthesize. It also has excellent absorption of light at a wavelength of 365 nm and an excellent photodecomposition rate.

[0170] In this disclosure, X 2 Preferably, direct bonding, C(R 101 )2, O, CO or NR 102 , wherein direct bonding, C(R 101 )2 or CO, particularly preferably a direct bond.

[0171] This is because through X 2 Compound A having the above structure has readily available raw materials and is easy to synthesize. It also has excellent absorption of light at a wavelength of 365 nm and an excellent photodecomposition rate.

[0172] In this disclosure, Y 1 Preferably C(R 201 )2, O, CO, S, N or NR 202 , wherein O, N or NR is preferred 202 , particularly preferably N.

[0173] This is because through Y 1 Compound A having the above structure has readily available raw materials and is easy to synthesize. It also has excellent absorption of light at a wavelength of 365 nm and an excellent photodecomposition rate.

[0174] In this disclosure, Y 2 Preferably C(R 201 )2, O, CO, S or NR 202 , wherein O, S or NR is preferred 202 , particularly preferably S.

[0175] This is because through Y 2 Compound A having the above structure has readily available raw materials and is easy to synthesize. It also has excellent absorption of light at a wavelength of 365 nm and an excellent photodecomposition rate.

[0176] In this disclosure, R 101 The hydrogen atoms and / or methylene groups in the hydrocarbon group or heterocyclic group may be substituted.

[0177] Hereinafter, the case where the hydrogen atoms and / or methylene groups in the hydrocarbon group or the heterocyclic ring-containing group may be substituted is also collectively referred to as "substitutable".

[0178] R 101 Preferred are hydrogen atoms, halogen atoms, amino groups, hydroxyl groups, nitro groups, hydrocarbon groups having 1 to 20 carbon atoms, or heterocyclic groups having 2 to 20 carbon atoms. Among them, hydrogen atoms, halogen atoms, hydrocarbon groups having 1 to 20 carbon atoms, or heterocyclic groups having 2 to 20 carbon atoms are preferred. A hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms is particularly preferred. A hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms is particularly preferred. A hydrogen atom or an alkyl group having 1 to 10 carbon atoms is particularly preferred. A hydrogen atom or the most preferred is a hydrogen atom.

[0179] This is because through R 101 Compound A having the above structure has readily available raw materials and is easy to synthesize. It also has excellent absorption of light at a wavelength of 365 nm and an excellent photodecomposition rate.

[0180] In this disclosure, R 102 Preferred are hydrogen atoms, halogen atoms, amino groups, hydroxyl groups, nitro groups, substitutable hydrocarbon groups having 1 to 20 carbon atoms, or substitutable heterocyclic groups having 2 to 20 carbon atoms. Among them, hydrogen atoms, halogen atoms, substitutable hydrocarbon groups having 1 to 20 carbon atoms, or substitutable heterocyclic groups having 2 to 20 carbon atoms are preferred. Especially preferred are hydrogen atoms or substitutable hydrocarbon groups having 1 to 20 carbon atoms. Among them, hydrogen atoms or substitutable hydrocarbon groups having 1 to 10 carbon atoms are particularly preferred. More preferred are substitutable hydrocarbon groups having 1 to 10 carbon atoms. Most preferred are substitutable alkyl groups having 1 to 10 carbon atoms.

[0181] This is because through R 102 Compound A having the above structure has readily available raw materials and is easy to synthesize. It also has excellent absorption of light at a wavelength of 365 nm and an excellent photodecomposition rate.

[0182] In this disclosure, R 201Preferred are hydrogen atom, halogen atom, amino group, hydroxyl group, nitro group, substitutable hydrocarbon group having 1 to 20 carbon atoms or substitutable heterocyclic group having 2 to 20 carbon atoms; among them, hydrogen atom, halogen atom, substitutable hydrocarbon group having 1 to 20 carbon atoms or substitutable heterocyclic group having 2 to 20 carbon atoms are preferred; hydrogen atom or substitutable hydrocarbon group having 1 to 20 carbon atoms is particularly preferred; among them, hydrogen atom or substitutable hydrocarbon group having 1 to 10 carbon atoms is particularly preferred; among them, hydrogen atom or substitutable alkyl group having 1 to 10 carbon atoms is particularly preferred; and hydrogen atom is most preferred.

[0183] This is because through R 201 Compound A having the above structure has readily available raw materials and is easy to synthesize. It also has excellent absorption of light at a wavelength of 365 nm and an excellent photodecomposition rate.

[0184] In this disclosure, R 202 Preferred are hydrogen atoms, halogen atoms, amino groups, hydroxyl groups, nitro groups, substitutable hydrocarbon groups having 1 to 20 carbon atoms, or substitutable heterocyclic groups having 2 to 20 carbon atoms. Among them, hydrogen atoms, halogen atoms, substitutable hydrocarbon groups having 1 to 20 carbon atoms, or substitutable heterocyclic groups having 2 to 20 carbon atoms are preferred. Especially preferred are hydrogen atoms or substitutable hydrocarbon groups having 1 to 20 carbon atoms. Among them, hydrogen atoms or substitutable hydrocarbon groups having 1 to 10 carbon atoms are particularly preferred. More preferred are substitutable hydrocarbon groups having 1 to 10 carbon atoms. Most preferred are substitutable alkyl groups having 1 to 10 carbon atoms.

[0185] This is because through R 202 Compound A having the above structure has readily available raw materials and is easy to synthesize. It also has excellent absorption of light at a wavelength of 365 nm and an excellent photodecomposition rate.

[0186] In this disclosure, R 31 It is preferably a substituted hydrocarbon group having 1 to 20 carbon atoms. The hydrocarbon group is preferably an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a cycloalkylalkyl group having 4 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an arylalkyl group having 7 to 20 carbon atoms. Among them, an alkyl group having 1 to 20 carbon atoms, a cycloalkylalkyl group having 4 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an arylalkyl group having 7 to 20 carbon atoms is preferred. Among them, R is particularly preferred. 31It is an optionally substituted alkyl group having 1 to 10 carbon atoms, an optionally substituted aryl group having 6 to 10 carbon atoms, an optionally substituted aralkyl group having 7 to 10 carbon atoms, or an optionally substituted 10-camphoryl group. It is particularly preferably an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aralkyl group having 7 to 10 carbon atoms, a 10-camphoryl group, or a group in which one or two or more hydrogen atoms of the above alkyl group, aryl group, aralkyl group, or 10-camphoryl group are substituted with halogen atoms. It is particularly preferably a group in which one or two or more hydrogen atoms of the alkyl group having 1 to 10 carbon atoms are substituted with halogen atoms.

[0187] This is because through R 31 With the above structure, Compound A has excellent absorption of light having a wavelength of 365 nm and also has an excellent photodecomposition rate.

[0188] In the present disclosure, in the above R 31 When the hydrogen atom in the group is substituted, the substituent is preferably a halogen atom, and among them, a fluorine atom is preferred. 31 In the case of an alkyl group in which a hydrogen atom in the group is substituted by a halogen atom, R is also preferably 31 In the alkyl group, three or more hydrogen atoms are substituted by halogen atoms, and R 31 A group in which all hydrogen atoms of an alkyl group are substituted with halogen atoms.

[0189] This is because through R 31 With the above structure, Compound A has excellent absorption of light having a wavelength of 365 nm and also has an excellent photodecomposition rate.

[0190] In this disclosure, R 32 Preferred are hydrogen atoms, halogen atoms, nitro groups, cyano groups or substitutable hydrocarbon groups having 1 to 20 carbon atoms, among which hydrogen atoms, halogen atoms, nitro groups, cyano groups or substitutable hydrocarbon groups having 1 to 10 carbon atoms are preferred, particularly preferred are hydrogen atoms, halogen atoms, cyano groups or substitutable hydrocarbon groups having 1 to 10 carbon atoms, among which cyano groups or substitutable hydrocarbon groups having 1 to 10 carbon atoms are particularly preferred, more preferred are substitutable hydrocarbon groups having 1 to 6 carbon atoms, and most preferred are substitutable alkyl groups having 1 to 6 carbon atoms.

[0191] This is because through R 32 With the above structure, Compound A has excellent absorption of light having a wavelength of 365 nm and also has an excellent photodecomposition rate.

[0192] In the present disclosure, in the above R 32 When a hydrogen atom in the group is substituted, the substituent is preferably a halogen atom, and particularly preferably a fluorine atom.

[0193] From these perspectives, as R32 , particularly preferably a halogenated alkyl group having 1 to 6 carbon atoms. 32 When the group is a haloalkyl group, preferably R 32 Three or more hydrogen atoms in the alkyl group are substituted with halogen atoms, and R 32 It is a group in which all hydrogen atoms of an alkyl group are substituted with halogen atoms.

[0194] This is because through R 32 With the above structure, Compound A has excellent absorption of light having a wavelength of 365 nm and also has an excellent photodecomposition rate.

[0195] In this disclosure, R 33 and R 34 It is preferably a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms, and more preferably a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an aryl group having 1 to 10 carbon atoms, or an arylalkyl group having 1 to 10 carbon atoms.

[0196] This is because through R 33 and R 34 With the above structure, Compound A has excellent absorption of light having a wavelength of 365 nm and also has an excellent photodecomposition rate.

[0197] In the present disclosure, n in the general formula (III) is preferably 0. This is because when n is the above structure, compound A has excellent absorption of light with a wavelength of 365 nm and also has excellent photodecomposition rate.

[0198] As specific structures of the compound A, for example, the following compounds No. 1 to No. 32 can be cited.

[0199] [Chemical Formula 8]

[0200]

[0201] [Chemical Formula 9]

[0202]

[0203] [Chemical Formula 10]

[0204]

[0205] X=(a)CF3SO2-*,(b)C4F9SO2-*,

[0206]

[0207] (Wherein, * represents the bonding site with =NO-.)

[0208] In the present disclosure, the compound A is preferably a compound represented by the following general formula (IIA) or (I-II-A), because it has excellent absorption of light with a wavelength of 365 nm and excellent photodecomposition rate.

[0209] [Chemical Formula 11]

[0210]

[0211] In the above general formulas (IIA) and (I-II-A), X 1A and X 2A Each independently represents a direct bond, C(R 101A )2, O, CO, S or NR 102A ,

[0212] The above R 101A and R 102A each independently represents a hydrogen atom, a halogen atom, a cyano group, an amino group, a hydroxyl group, a nitro group, a carboxyl group, a hydrocarbon group having 1 to 20 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms,

[0213] The above R 101A and R 102A The hydrocarbon group and heterocyclic ring-containing group used in the group are groups in which the hydrogen atoms in the group are not substituted, or one or more of the hydrogen atoms are substituted by a halogen atom, a cyano group, a nitro group, a hydroxyl group, a thiol group, -COOH, -SO3H, an isocyanate group or an alkyl group having 1 to 4 carbon atoms, and one or more of the methylene groups in the group are sometimes substituted by a divalent group selected from the following <Group I>.

[0214] The above R 1 、R 2 、R 3 、R 4 、R 9 and R 10 Each independently represents a hydrogen atom, a halogen atom, a cyano group, an amino group, a hydroxyl group, a nitro group, a carboxyl group, a hydrocarbon group having 1 to 20 carbon atoms, a heterocyclic group having 2 to 20 carbon atoms, or a group represented by the following general formula (IV),

[0215] The above R 5 、R 6 、R 7 、R 8 、R 11 、R 12 、R 13 and R 14 Each independently represents a hydrogen atom, a halogen atom, a cyano group, an amino group, a hydroxyl group, a nitro group, a carboxyl group, a hydrocarbon group having 1 to 20 carbon atoms, a heterocyclic group having 2 to 20 carbon atoms, or a group represented by the following general formula (III-A),

[0216] The above R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 10 、R 11 、R 12 、R 13 and R 14 The hydrocarbon group and heterocyclic ring-containing group used in the group are groups in which the hydrogen atoms in the group are not substituted, or one or more of the hydrogen atoms are substituted by a halogen atom, a cyano group, a nitro group, a hydroxyl group, a thiol group, -COOH, -SO3H, an isocyanate group or an alkyl group having 1 to 4 carbon atoms, and one or more of the methylene groups in the group are sometimes substituted by a divalent group selected from the following <Group I>.

[0217] The above R 1 、R 2 、R 3 and R 4 At least one of represents a group represented by the following general formula (IV),

[0218] The above R 5 、R 6 、R 7 and R 8 At least one of them represents a group represented by the following general formula (III-A),

[0219] R 9 and R 10 At least one of represents a group represented by the following general formula (IV),

[0220] R 11 、R 12 、R 13 and R 14 At least one of them represents a group represented by the following general formula (III-A),

[0221] [Chemical Formula 12]

[0222]

[0223] The above R 31A represents a hydrocarbon group having 1 to 20 carbon atoms or a heterocyclic group having 2 to 20 carbon atoms,

[0224] The above R 32A represents a hydrogen atom, a halogen atom, a nitro group, a cyano group, a hydrocarbon group having 1 to 20 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms,

[0225] The above R 31A and R 32A The hydrocarbon group and heterocyclic ring-containing group used in the group are groups in which the hydrogen atoms in the group are unsubstituted, or one or two or more of the hydrogen atoms are substituted by a halogen atom, a cyano group, a nitro group, a hydroxyl group, a thiol group, -COOH, -SO3H, an isocyanate group, or an alkyl group having 1 to 4 carbon atoms, and one or two or more methylene groups in the group may be substituted by a divalent group selected from the following <Group I>,

[0226] The n represents 0 or 1,

[0227] *Indicates the bonding site,

[0228] [Chemical Formula 13]

[0229] *-R 41 -R 42 (IV)

[0230] The above R 41 Each independently represents a direct bond, a divalent group selected from the following <Group I>, a hydrocarbon group having 1 to 20 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms,

[0231] The above R 41 The hydrocarbon group and heterocyclic ring-containing group used in the group are groups in which the hydrogen atoms in the group are not substituted, or one or more of the hydrogen atoms are substituted by a halogen atom, a cyano group, a nitro group, a hydroxyl group, a thiol group, -COOH, -SO3H, an isocyanate group or an alkyl group having 1 to 4 carbon atoms, and one or more of the methylene groups in the group are sometimes substituted by a divalent group selected from the following <Group I>.

[0232] *Indicates bonding site.

[0233] The above R 42 It represents a group represented by any of the following general formulas (II-A-1), (II-A-2) or (II-A-3).

[0234] [Chemical Formula 14]

[0235]

[0236] The above Y 1A 、Y 1A-2 and Y 1A-3 Each independently represents C(R 201A )2, O, CO, S, N or NR 202A ,

[0237] Among them, Y 1A 、Y 1A-2 and Y 1A-3When N is present, a double bond is formed as shown by the dotted line.

[0238] The above Y 2A 、Y 2A-2 and Y 2A-3 Each independently represents C(R 201A )2, O, CO, S or NR 202A ,

[0239] The above R 201A and R 202A each independently represents a hydrogen atom, a halogen atom, a cyano group, an amino group, a hydroxyl group, a nitro group, a carboxyl group, a hydrocarbon group having 1 to 20 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms,

[0240] The above R 201A and R 202A The hydrocarbon group and heterocyclic ring-containing group used in the group are groups in which the hydrogen atoms in the group are unsubstituted, or one or two or more of the hydrogen atoms are substituted by a halogen atom, a cyano group, a nitro group, a hydroxyl group, a thiol group, -COOH, -SO3H, an isocyanate group, or an alkyl group having 1 to 4 carbon atoms, and one or two or more methylene groups in the group may be substituted by a divalent group selected from the following <Group I>,

[0241] The above R 21 、R 22 、R 23 、R 24 、R 22-2 、R 23-2 、R 24-2 、R 25-2 、R 21-3 、R 23-3 、R 24-3 and R 25-3 Each independently represents a hydrogen atom, a halogen atom, a cyano group, an amino group, a hydroxyl group, a nitro group, a carboxyl group, a hydrocarbon group having 1 to 20 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms,

[0242] The above R 21 、R 22 、R 23 、R 24 、R 22-2 、R 23-2 、R 24-2 、R 25-2 、R 21-3 、R 23-3 、R 24-3 and R 25-3The hydrocarbon group and heterocyclic ring-containing group used in the group are groups in which the hydrogen atoms in the group are unsubstituted, or one or two or more of the hydrogen atoms are substituted by a halogen atom, a cyano group, a nitro group, a hydroxyl group, a thiol group, -COOH, -SO3H, an isocyanate group, or an alkyl group having 1 to 4 carbon atoms, and one or two or more methylene groups in the group may be substituted by a divalent group selected from the following <Group I>,

[0243] * indicates the same as R 41 The bonding site,

[0244] Group I: -O-, -COO-, -OCO-, -CO-, -CS-, -S-, -SO-, -SO2-, -NR 33 -、-NR 33 -CO-, -CO-NR 33 -、-NR 33 -COO-, -OCO-NR 33 -or-SiR 33 R 34 -,

[0245] R 33 and R 34 Each independently represents a hydrogen atom, an unsubstituted hydrocarbon group having 1 to 10 carbon atoms, or an unsubstituted heterocyclic group having 1 to 10 carbon atoms.

[0246] As the above R 101A and R 102A The unsubstituted hydrocarbon group having 1 to 20 carbon atoms used in the above structures I and II can be any of the hydrocarbon groups listed as substituents for hydrogen atoms, as long as the substituents satisfy the specified number of carbon atoms.

[0247] As the above R 101A and R 102A The unsubstituted heterocyclic group having 2 to 20 carbon atoms used in the above structures I and II can be any of the heterocyclic groups listed as substituents for hydrogen atoms, as long as the substituents satisfy the specified number of carbon atoms.

[0248] As the above R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 10 、R 11 、R 12 、R 13 and R 14The unsubstituted hydrocarbon group having 1 to 20 carbon atoms used in the above structures I and II can be any of the hydrocarbon groups listed as substituents for hydrogen atoms, as long as the substituents satisfy the specified number of carbon atoms.

[0249] As the above R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 10 、R 11 、R 12 、R 13 and R 14 The unsubstituted heterocyclic group having 2 to 20 carbon atoms used in the above structures I and II can be any of the heterocyclic groups listed as substituents for hydrogen atoms, as long as the substituents satisfy the specified number of carbon atoms.

[0250] As the above R 41 The unsubstituted hydrocarbon group having 1 to 20 carbon atoms used in the above structures I and II can be a divalent group obtained by removing one hydrogen atom from the hydrocarbon group exemplified as a substituent for replacing a hydrogen atom in the above structures I and II.

[0251] As the above R 41 The unsubstituted heterocyclic group having 2 to 20 carbon atoms used in the above structures I and II can be a divalent group obtained by removing one hydrogen atom from the heterocyclic group exemplified as a substituent for replacing a hydrogen atom in the above structures I and II.

[0252] As the above R 201A and R 202A The unsubstituted hydrocarbon group having 1 to 20 carbon atoms used in the above structures I and II can be any of the hydrocarbon groups listed as substituents for hydrogen atoms, as long as the substituents satisfy the specified number of carbon atoms.

[0253] As the above R 201A and R 202A The unsubstituted heterocyclic group having 2 to 20 carbon atoms used in the above structures I and II etc. can be any of the heterocyclic groups listed as substituents for substituting hydrogen atoms in the above structures I and II etc., as long as the group has the specified number of carbon atoms.

[0254] As the above R 21 、R 22 、R 23 、R24 、R 22-2 、R 23-2 、R 24-2 、R 25-2 、R 21-3 、R 23-3 、R 24-3 and R 25-3 The unsubstituted hydrocarbon group having 1 to 20 carbon atoms used in the above structures I and II can be any of the hydrocarbon groups listed as substituents for hydrogen atoms, as long as the substituents satisfy the specified number of carbon atoms.

[0255] As the above R 21 、R 22 、R 23 、R 24 、R 22-2 、R 23-2 、R 24-2 、R 25-2 、R 21-3 、R 23-3 、R 24-3 and R 25-3 The unsubstituted heterocyclic group having 2 to 20 carbon atoms used in the above structures I and II can be any of the heterocyclic groups listed as substituents for hydrogen atoms, as long as the substituents satisfy the specified number of carbon atoms.

[0256] In the above formulae (III) and (III-A), R 31A and R 32A The unsubstituted hydrocarbon group having 1 to 20 carbon atoms used in the above structures I and II can be any of the hydrocarbon groups listed as substituents for hydrogen atoms, as long as the substituents satisfy the specified number of carbon atoms.

[0257] In the above formulae (III) and (III-A), R 31A and R 32A The unsubstituted heterocyclic group having 2 to 20 carbon atoms used in the above structures I and II can be any of the heterocyclic groups listed as substituents for hydrogen atoms, as long as the substituents satisfy the specified number of carbon atoms.

[0258] In the present specification, examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0259] In this disclosure, X 1A Preferably -C(R 101A )2-, -O-, -S-, or -NR 102A -, wherein -C(R 101A )2-, -O- or -NR 102A-, particularly preferably -NR 102A -.

[0260] This is because through X 1A Compound A having the above structure has readily available raw materials and is easy to synthesize. It also has excellent absorption of light at a wavelength of 365 nm and an excellent photodecomposition rate.

[0261] In this disclosure, X 2A Preferably, a direct bond, -C(R 101A )2-, -O-, -CO- or -NR 102A -, wherein direct bond, -C(R 101A )2- or -CO-, and a direct bond is particularly preferred.

[0262] This is because through X 2A Compound A having the above structure has readily available raw materials and is easy to synthesize. It also has excellent absorption of light at a wavelength of 365 nm and an excellent photodecomposition rate.

[0263] In this disclosure, R 101A Preferred are hydrogen atom, halogen atom, amino group, hydroxyl group, nitro group, substitutable hydrocarbon group having 1 to 20 carbon atoms or substitutable heterocyclic group having 2 to 20 carbon atoms; among them, hydrogen atom, halogen atom, substitutable hydrocarbon group having 1 to 20 carbon atoms or substitutable heterocyclic group having 2 to 20 carbon atoms are preferred; hydrogen atom or substitutable hydrocarbon group having 1 to 20 carbon atoms is particularly preferred; among them, hydrogen atom or substitutable hydrocarbon group having 1 to 10 carbon atoms is particularly preferred; among them, hydrogen atom or substitutable alkyl group having 1 to 10 carbon atoms is particularly preferred; and hydrogen atom is most preferred.

[0264] This is because through R 101A Compound A having the above structure has readily available raw materials and is easy to synthesize. It also has excellent absorption of light at a wavelength of 365 nm and an excellent photodecomposition rate.

[0265] In this disclosure, R 102A Preferred are hydrogen atoms, halogen atoms, amino groups, hydroxyl groups, nitro groups, substitutable hydrocarbon groups having 1 to 20 carbon atoms, or substitutable heterocyclic groups having 2 to 20 carbon atoms. Among them, hydrogen atoms, halogen atoms, substitutable hydrocarbon groups having 1 to 20 carbon atoms, or substitutable heterocyclic groups having 2 to 20 carbon atoms are preferred. Especially preferred are hydrogen atoms or substitutable hydrocarbon groups having 1 to 20 carbon atoms. Among them, hydrogen atoms or substitutable hydrocarbon groups having 1 to 10 carbon atoms are particularly preferred. More preferred are substitutable hydrocarbon groups having 1 to 10 carbon atoms. Most preferred are substitutable alkyl groups having 1 to 10 carbon atoms.

[0266] This is because through R 102ACompound A having the above structure has readily available raw materials and is easy to synthesize. It also has excellent absorption of light at a wavelength of 365 nm and an excellent photodecomposition rate.

[0267] In this disclosure, as R 1 、R 2 、R 3 and R 4 The number of groups represented by the general formula (IV) in is preferably 1 to 3, particularly preferably 1 to 2, and particularly preferably 1.

[0268] This is because through R 1 、R 2 、R 3 and R 4 Compound A having the above structure has readily available raw materials and is easy to synthesize. It also has excellent absorption of light at a wavelength of 365 nm and an excellent photodecomposition rate.

[0269] In this disclosure, R 1 、R 2 、R 3 and R 4 The group other than the group represented by general formula (IV) is preferably a hydrogen atom, a halogen atom, an amino group, a hydroxyl group, a nitro group, a carboxyl group, a hydrocarbon group having 1 to 20 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms. Among them, a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms is preferred, a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms is particularly preferred, a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms is more preferred, and a hydrogen atom or an alkyl group having 1 to 10 carbon atoms is most preferred.

[0270] This is because through R 1 、R 2 、R 3 and R 4 Compound A having the above structure has readily available raw materials and is easy to synthesize. It also has excellent absorption of light at a wavelength of 365 nm and an excellent photodecomposition rate.

[0271] In this disclosure, as R 5 、R 6 、R 7 and R 8 The number of groups represented by the general formula (III-A) in is preferably 1 to 3, particularly preferably 1 to 2, and particularly preferably 1.

[0272] This is because through R 5 、R 6 、R 7 and R 8 Compound A having the above structure has readily available raw materials and is easy to synthesize. It also has excellent absorption of light at a wavelength of 365 nm and an excellent photodecomposition rate.

[0273] In this disclosure, R 5 、R 6 、R 7 and R 8 The group other than the group represented by the general formula (III-A) is preferably a hydrogen atom, a halogen atom, an amino group, a hydroxyl group, a nitro group, a carboxyl group, a hydrocarbon group having 1 to 20 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms, among which a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms is preferred, a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, is particularly preferred, a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms is more preferred, and a hydrogen atom or an alkyl group having 1 to 10 carbon atoms is most preferred.

[0274] This is because through R 5 、R 6 、R 7 and R 8 Compound A having the above structure has readily available raw materials and is easy to synthesize. It also has excellent absorption of light at a wavelength of 365 nm and an excellent photodecomposition rate.

[0275] In this disclosure, as R 9 and R 10 The number of groups represented by the general formula (IV) in is preferably 1 to 2, and particularly preferably 1.

[0276] This is because through R 9 and R 10 Compound A having the above structure has readily available raw materials and is easy to synthesize. It also has excellent absorption of light at a wavelength of 365 nm and an excellent photodecomposition rate.

[0277] In this disclosure, R 9 and R 10 The group other than the group represented by general formula (IV) is preferably a hydrogen atom, a halogen atom, an amino group, a hydroxyl group, a nitro group, a carboxyl group, a hydrocarbon group having 1 to 20 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms. Among them, a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms is preferred, a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms is particularly preferred, a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms is more preferred, and a hydrogen atom or an alkyl group having 1 to 10 carbon atoms is most preferred.

[0278] This is because through R 9 and R 10 Compound A having the above structure has readily available raw materials and is easy to synthesize. It also has excellent absorption of light at a wavelength of 365 nm and an excellent photodecomposition rate.

[0279] In this disclosure, as R 11 、R 12 、R13 and R 14 The number of groups represented by the general formula (III-A) in is preferably 1 to 3, particularly preferably 1 to 2, and particularly preferably 1.

[0280] This is because through R 11 、R 12 、R 13 and R 14 Compound A having the above structure has readily available raw materials and is easy to synthesize. It also has excellent absorption of light at a wavelength of 365 nm and an excellent photodecomposition rate.

[0281] In this disclosure, R 11 、R 12 、R 13 and R 14 The group other than the group represented by the general formula (III-A) is preferably a hydrogen atom, a halogen atom, an amino group, a hydroxyl group, a nitro group, a carboxyl group, a hydrocarbon group having 1 to 20 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms, among which a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms is preferred, a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, is particularly preferred, a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms is more preferred, and a hydrogen atom or an alkyl group having 1 to 10 carbon atoms is most preferred.

[0282] This is because through R 11 、R 12 、R 13 and R 14 Compound A having the above structure has readily available raw materials and is easy to synthesize. It also has excellent absorption of light at a wavelength of 365 nm and an excellent photodecomposition rate.

[0283] Preferably, the above R 2 and R 9 is a group represented by formula (IV), wherein the above R 7 and R 13 This is because compound A has readily available raw materials, is easily synthesized, has excellent absorption of light at a wavelength of 365 nm, and has an excellent photodecomposition rate.

[0284] In this disclosure, R 41 Preferred are direct bonds, divalent groups selected from the following <Group I>, or hydrocarbon groups having 1 to 20 carbon atoms. Among them, preferred are direct bonds or divalent groups selected from the following <Group I>, and particularly preferred are direct bonds.

[0285] This is because through R 41 With the above structure, Compound A has excellent absorption of light having a wavelength of 365 nm and also has an excellent photodecomposition rate.

[0286] In this disclosure, R42 The above-mentioned general formula (II-A-1) is preferred.

[0287] This is because through R 42 With the above structure, Compound A has excellent absorption of light having a wavelength of 365 nm and also has an excellent photodecomposition rate.

[0288] In this disclosure, Y 1A 、Y 1A-2 and Y 1A-3 Preferably C(R 201A )2, O, CO, S, N or NR 202A , wherein O, N or NR is preferred 202A , particularly preferably N.

[0289] This is because through Y 1A 、Y 1A-2 and Y 1A-3 Compound A having the above structure is easy to obtain as a raw material, has excellent absorption of light with a wavelength of 365 nm, and also has an excellent photodecomposition rate.

[0290] In this disclosure, Y 2A 、Y 2A-2 and Y 2A-3 Preferably C(R 201A )2, O, CO, S or NR 202A , wherein O, S or NR is preferred 202A , particularly preferably S.

[0291] This is because through Y 2A 、Y 2A-2 and Y 2A-3 Compound A having the above structure is easy to obtain as a raw material, has excellent absorption of light with a wavelength of 365 nm, and also has an excellent photodecomposition rate.

[0292] In this disclosure, R 201A Preferred are hydrogen atoms, halogen atoms, amino groups, hydroxyl groups, nitro groups, substitutable hydrocarbon groups having 1 to 20 carbon atoms, or substitutable heterocyclic groups having 2 to 20 carbon atoms. Among them, hydrogen atoms, halogen atoms, substitutable hydrocarbon groups having 1 to 20 carbon atoms, or substitutable heterocyclic groups having 2 to 20 carbon atoms are preferred. Hydrogen atoms and substitutable hydrocarbon groups having 1 to 20 carbon atoms are particularly preferred. Among them, hydrogen atoms and substitutable hydrocarbon groups having 1 to 10 carbon atoms are particularly preferred. Among them, hydrogen atoms and substitutable alkyl groups having 1 to 10 carbon atoms are particularly preferred. A hydrogen atom is most preferred.

[0293] This is because through R 201A Compound A having the above structure has readily available raw materials and is easy to synthesize. It also has excellent absorption of light at a wavelength of 365 nm and an excellent photodecomposition rate.

[0294] In this disclosure, R 202A Preferred are hydrogen atoms, halogen atoms, amino groups, hydroxyl groups, nitro groups, substitutable hydrocarbon groups having 1 to 20 carbon atoms, or substitutable heterocyclic groups having 2 to 20 carbon atoms. Among them, hydrogen atoms, halogen atoms, substitutable hydrocarbon groups having 1 to 20 carbon atoms, or substitutable heterocyclic groups having 2 to 20 carbon atoms are preferred. Especially preferred are hydrogen atoms and substitutable hydrocarbon groups having 1 to 20 carbon atoms. Among them, hydrogen atoms and substitutable hydrocarbon groups having 1 to 10 carbon atoms are particularly preferred. More preferred are substitutable hydrocarbon groups having 1 to 10 carbon atoms. Most preferred are substitutable alkyl groups having 1 to 10 carbon atoms.

[0295] This is because through R 202A Compound A having the above structure has readily available raw materials and is easy to synthesize. It also has excellent absorption of light at a wavelength of 365 nm and an excellent photodecomposition rate.

[0296] In this disclosure, R 21 、R 22 、R 23 、R 24 、R 22-2 、R 23-2 、R 24-2 、R 25-2 、R 21-3 、R 23-3 、R 24-3 and R 25-3 Each is independently preferably a hydrogen atom, a halogen atom, a hydrocarbon group having 1 to 20 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms, among which a hydrogen atom, a halogen atom, or a hydrocarbon group having 1 to 20 carbon atoms is preferred, among which a hydrogen atom, a halogen atom, or a hydrocarbon group having 1 to 10 carbon atoms is particularly preferred, a hydrogen atom, a halogen atom, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 1 to 10 carbon atoms is more preferred, and a hydrogen atom is most preferred.

[0297] This is because through R 21 、R 22 、R 23 、R 24 、R 22-2 、R 23-2 、R 24-2 、R 25-2 、R 21-3 、R 23-3 、R 24-3 and R 25-3 Compound A having the above structure is easy to obtain as a raw material, has excellent absorption of light with a wavelength of 365 nm, and also has an excellent photodecomposition rate.

[0298] In the present disclosure, the above R 31AIt is preferably a substituted hydrocarbon group having 1 to 20 carbon atoms. In this group, the hydrocarbon group is preferably an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a cycloalkylalkyl group having 4 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an arylalkyl group having 7 to 20 carbon atoms. Among them, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, a cycloalkylalkyl group having 1 to 20 carbon atoms, or an arylalkyl group having 7 to 20 carbon atoms is preferred. Among them, R is particularly preferred. 31A It is an optionally substituted alkyl group having 1 to 10 carbon atoms, an optionally substituted aryl group having 6 to 10 carbon atoms, an optionally substituted aralkyl group having 7 to 10 carbon atoms, or an optionally substituted 10-camphoryl group. It is particularly preferably an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aralkyl group having 7 to 10 carbon atoms, a 10-camphoryl group, or a group in which one or two or more hydrogen atoms of the above alkyl group, aryl group, aralkyl group, or 10-camphoryl group are substituted with halogen atoms. It is particularly preferably a group in which one or two or more hydrogen atoms of an alkyl group having 1 to 10 carbon atoms are substituted with halogen atoms. It is particularly preferably an optionally substituted alkyl group having 1 to 10 carbon atoms.

[0299] This is because through R 31A With the above structure, Compound A has excellent absorption of light having a wavelength of 365 nm and also has an excellent photodecomposition rate.

[0300] In the present disclosure, in the above R 31A When the hydrogen atom in the group is substituted, the substituent is preferably a halogen atom, and among them, a fluorine atom is preferred. 31A In the case of an alkyl group in which a hydrogen atom in the group is substituted by a halogen atom, it is also preferred that R 31A In the case where three or more hydrogen atoms in the alkyl group are replaced by halogen atoms, it is also preferred that R 31A It has a group in which all hydrogen atoms of an alkyl group are substituted with halogen atoms.

[0301] This is because through R 31A With the above structure, Compound A has excellent absorption of light having a wavelength of 365 nm and also has an excellent photodecomposition rate.

[0302] In the present disclosure, the above R 32A Preferred are hydrogen atoms, halogen atoms, nitro groups, cyano groups or substitutable hydrocarbon groups having 1 to 20 carbon atoms, among which hydrogen atoms, halogen atoms, nitro groups, cyano groups or substitutable hydrocarbon groups having 1 to 10 carbon atoms are preferred, particularly preferred are hydrogen atoms, halogen atoms, cyano groups or substitutable hydrocarbon groups having 1 to 10 carbon atoms, among which cyano groups or substitutable hydrocarbon groups having 1 to 10 carbon atoms are particularly preferred, more preferred are substitutable hydrocarbon groups having 1 to 6 carbon atoms, and most preferred are substitutable alkyl groups having 1 to 6 carbon atoms.

[0303] This is because through R 32A With the above structure, Compound A has excellent absorption of light having a wavelength of 365 nm and also has an excellent photodecomposition rate.

[0304] In the present disclosure, in the above R 32A When the hydrogen atom in the group is substituted, the substituent is preferably a halogen atom, and among them, a fluorine atom is preferred. 32A , particularly preferably a halogenated alkyl group having 1 to 6 carbon atoms. 32A When the group is a halogenated alkyl group, it is also preferred that R 32A In the case where three or more hydrogen atoms in the alkyl group are substituted with halogen atoms, it is also preferred that R 32A This is a group obtained by replacing all hydrogen atoms of an alkyl group with halogen atoms.

[0305] This is because through R 32A With the above structure, Compound A has excellent absorption of light having a wavelength of 365 nm and also has an excellent photodecomposition rate.

[0306] In the present disclosure, n in the above general formula (III-A) is preferably 0.

[0307] This is because when n is the above structure, Compound A has excellent absorption of light with a wavelength of 365 nm and also has an excellent photodecomposition rate.

[0308] In the present disclosure, the molar absorption coefficient of compound A with respect to light having a wavelength of 365 nm is preferably 13,000 or more and 40,000 or less, and particularly preferably 15,000 or more and 30,000 or less.

[0309] This is because compound A having the above structure has excellent absorption of light with a wavelength of 365 nm and also excellent photodecomposition rate.

[0310] The absorption coefficient was calculated by measuring the absorption spectrum at 365 nm of a solution in which the compound was dissolved using an ultraviolet-visible spectrophotometer (U-3010 manufactured by Hitachi High-Tech Science).

[0311] In the present disclosure, the photodecomposition rate of compound A with respect to light having a wavelength of 365 nm is preferably 60% or higher, more preferably 70% or higher, and particularly preferably 80% or higher.

[0312] This is because compound A having the above structure can provide a compound having an excellent photodegradation rate.

[0313] The photodecomposition rate was calculated by sealing the solution used for the above-mentioned absorption coefficient measurement, exposing it to a UVLED light source, and measuring the solution before and after exposure using high performance liquid chromatography (HPLC) to determine the decomposition rate of the compound.

[0314] The method for producing Compound A is any method that can produce a compound of the desired structure, and known chemical reactions can be used for synthesis. For example, Compound No. 1 can be synthesized by the method shown in the following flow chart. The reaction conditions in the production method, such as reaction temperature, reaction time, and the amount of raw materials used, are not particularly limited and can be used under known conditions.

[0315] [Chemical Formula 15]

[0316] (Scheme 1)

[0317]

[0318] (X 1 and X 2 With X of formula (II) 1 and X 2 Same. DMF is dimethylformamide, MCB is monochlorobenzene.)

[0319] [Chemical Formula 16]

[0320] (Scheme 2)

[0321]

[0322] (X 1 and X 2 With X of formula (II) 1 and X 2 Same. 1 and A 2 Each is independently -CH3, -OH, -SH or -NH2. 1′ and A 2′ With Y of formula (III) 1 and Y 2 Same. DMAC is dimethylacetamide.)

[0323] [Chemical Formula 17]

[0324] (Scheme 3)

[0325]

[0326] (X 1 and X 2 With X of formula (II) 1 and X 2 Same. 1′ and A2′ With Y of formula (III) 1 and Y 2 Same. 32 With R of formula (III) 32 Same. DCM is dichloromethane.)

[0327] [Chemical Formula 18]

[0328] (Scheme 4)

[0329]

[0330] (X 1 and X 2 With X of formula (II) 1 and X 2 Same. 1′ and A 2′ With Y of formula (III) 1 and Y 2 Same. 32 With R of formula (III) 32 same.)

[0331] [Chemical Formula 19]

[0332] (Scheme 5)

[0333]

[0334] (X 1 and X 2 With X of formula (II) 1 and X 2 Same. 1′ and A 2′ With Y of formula (III) 1 and Y 2 Same. 31 With R of formula (III) 31 Same. 32 With R of formula (III) 32 same.)

[0335] It should be noted that the following schemes can be used instead of schemes 1 and 2 (as described below, especially A 1′ (Y 1 ) is the case of CO, etc.).

[0336] [Chemical Formula 20]

[0337]

[0338] (X 1 and X 2 With X of formula (II)1 and X 2 Same. 2′ With Y of formula (III) 2 same.)

[0339] The compound A has a function of generating an acid by decomposing a part of its structure.

[0340] As a method for generating an acid from the compound A, methods commonly used for acid generators can be used. Specifically, methods include irradiation with energy rays, heat treatment, and simultaneous or sequential application of these methods. Examples of the energy rays include g-rays (436 nm), h-rays (405 nm), i-rays (365 nm), visible light, ultraviolet rays, extreme ultraviolet rays, X-rays, and charged particle beams.

[0341] In addition, examples of light sources include low-pressure mercury lamps, medium-pressure mercury lamps, high-pressure mercury lamps, ultra-high-pressure mercury lamps, xenon lamps, metal halide lamps, electron beam irradiation devices, X-ray irradiation devices, and lasers (argon lasers, dye lasers, nitrogen lasers, LEDs, helium-cadmium lasers, etc.).

[0342] The heating temperature in the heat treatment is preferably, for example, 70°C to 450°C, preferably 100°C to 400°C, more preferably 105°C to 370°C, and may be 150°C or higher. Furthermore, the heating time in the heat treatment is preferably, for example, 1 minute to 100 minutes. This is because these heat treatment conditions can suppress color changes in the composition.

[0343] Since the compound A has excellent absorption of light with a wavelength of 365 nm and an excellent photodecomposition rate, it is preferable to use a method of generating an acid by irradiating the compound with energy rays, particularly i-rays.

[0344] Examples of uses of the compound A include acid generators, and more specifically, photoacid generators that generate acid by energy ray irradiation, and thermal acid generators that generate acid by heat treatment.

[0345] Examples of uses of the acid generator include addition to a composition containing a resin component.

[0346] The composition can be used, for example, in optical filters, coatings, coating agents, lining agents, adhesives, printing plates, insulating varnishes, insulating sheets, laminates, printed substrates, sealants for semiconductor devices, LED packages, liquid crystal injection ports, organic EL devices, optical components, electrical insulation, electronic components, and separation membranes, molding materials, putties, glass fiber impregnation agents, fillers, passivation films for semiconductors and solar cells, interlayer insulating films, surface protective films, printed substrates, and the like used in thin film transistors (TFTs), liquid crystal display devices, organic EL display devices, and printed substrates, or

[0347] Color filters for color TVs, PC monitors, portable information terminals, CCD image sensors, electrode materials for plasma display panels, printing inks, dental compositions, photomolding resins, both liquid and dry films, micromechanical components, glass fiber cable coatings, holographic recording materials, magnetic recording materials, optical switches, plating masks, etching masks, screen printing templates, transparent conductive films and other touch panels, MEMS elements, nanoimprint materials, photosensitive processing such as two-dimensional and three-dimensional high-density mounting of semiconductor packages, decorative sheets, artificial nails, glass-substitute optical films, electronic paper, optical discs, microlens arrays used in projector / optical communication lasers, prism lens sheets used in backlights of liquid crystal displays, Fresnel lens sheets and lenticular lens sheets used in screens of projection TVs, etc. The applications include, but are not limited to, lens portions, microlenses for backlights, etc., optical lenses such as imaging lenses, optical elements, optical connectors, optical waveguides, insulating gaskets, heat shrinkable rubber tubes, O-rings, sealants for display devices, protective materials, optical fiber protective materials, adhesives, die bonding agents, high heat dissipation materials, high heat-resistant sealing materials, components for solar cells, fuel cells, and secondary batteries, solid electrolytes for batteries, insulating coating materials, photosensitive drums for copiers, gas separation membranes, civil engineering and construction materials such as concrete protective materials, linings, soil injection agents, sealants, heat storage materials, glass coatings, and foams, pipes, sealing materials, coating materials, sealing materials for sterilization equipment, contact lenses, oxygen-enriched membranes, medical materials such as biochips, automotive parts, and various machine parts.

[0348] From the viewpoint of more effectively exerting the effect of excellent acid generation sensitivity, the above-mentioned application is preferably an application in a pattern forming composition, for example, preferably an application in a negative composition used with an acid-curable component (also referred to as an "acid-curable resin component"), preferably an application in a positive composition used with an acid-decomposable component (also referred to as an "acid-decomposable resin component"), and more specifically, preferably an application in a composition used in the formation of an interlayer insulating film used in optical lenses, optical elements, optical connectors, optical waveguides, liquid crystal displays / organic EL displays / printed substrates, etc., which require high acid generation sensitivity.

[0349] B. Composition

[0350] The composition of the present invention (hereinafter, sometimes referred to as composition B) is characterized by containing compound A.

[0351] According to the present invention, by using Compound A having excellent absorption of light at a wavelength of 365 nm and excellent photodecomposition rate, Compound A efficiently decomposes to generate acid, thereby inducing excellent curing reaction and decomposition reaction in a composition having acid-reactive components.

[0352] 1. Compound A

[0353] As Compound A, the same compounds as those described in the above-mentioned "A. Compound" can be used, and therefore, description thereof will be omitted here.

[0354] The type of the compound A used in the composition B of the present invention may be any type as long as the predetermined effect is exhibited, and the composition B may contain only one type or two or more types.

[0355] In the present invention, when compound A is used for the acid-reactive resin component, the content of compound A is not particularly limited, but is preferably 0.05 to 100 parts by mass, more preferably 0.05 to 20 parts by mass, based on 100 parts by mass of the acid-reactive resin component.

[0356] However, the amount of the acid-reactive organic substance may be increased or decreased from the above range depending on factors such as the properties of the acid-reactive organic substance, light irradiation intensity, time required for the reaction, physical properties, and cost.

[0357] This is because in the composition B, the compound A is efficiently decomposed to generate an acid, and in the composition B having an acid-reactive component, an excellent curing reaction and a decomposition reaction can be induced.

[0358] The content of the compound A in the composition of the present invention is preferably 0.001 parts by mass or more and 20 parts by mass or less per 100 parts by mass of the solid content of the composition.

[0359] This is because in the composition B, the compound A is efficiently decomposed to generate an acid, and in the composition B having an acid-reactive component, an excellent curing reaction and a decomposition reaction can be induced.

[0360] The content of the compound A in the composition of the present invention is preferably 0.001 parts by mass or more and 20 parts by mass or less per 100 parts by mass of the composition. This is because compound A efficiently decomposes in composition B to generate acid, and composition B having an acid-reactive component can induce excellent curing reaction and decomposition reaction.

[0361] The content of the compound A mentioned above indicates the total amount of the compounds A when two or more types of compounds A are included.

[0362] 2. Resin composition

[0363] Composition B may contain a resin component.

[0364] As the resin component, a polymer compound or a component capable of becoming a polymer compound can be used.

[0365] The resin component may be an acid-reactive resin component having a structure capable of reacting with an acid generated by decomposition of compound A, or a non-acid-reactive resin component that does not react with an acid generated from compound A. Preferably, the resin component is an acid-reactive resin component.

[0366] This is because by using an acid-reactive resin component as the resin component, the composition B can exhibit excellent reactivity due to the acid generated by the decomposition of the compound A.

[0367] Examples of such acid-reactive resin components include acid-curable resin components that are cured by polymerization or crosslinking due to the acid generated from compound A, and acid-decomposable resin components whose solubility in a developer is increased by the acid generated from compound A.

[0368] Examples of the acid-curable resin component include cationically polymerizable compounds.

[0369] As the above-mentioned cationic polymerizable compounds, in addition to cyclic ether compounds such as epoxy compounds and oxetane compounds, vinyl ether compounds, vinyl compounds, styrenes, spiro orthoesters, bicyclic orthoesters, spiro orthocarbonates, lactones, oxazolines, aziridines, cyclosiloxanes, ketals, cyclic acid anhydrides, lactams, aryl dialdehydes, etc., polymerizable or crosslinked polymers and oligomers having these polymerizable groups in the side chain can also be listed. They can be alone or mixed with two or more. As a specific example of such a cationic polymerizable compound, for example, the acid-reactive organic substance described in International Publication No. 2017 / 130896, International Publication No. 2014 / 084269, International Publication No. 2016 / 132413, etc. can be used.

[0370] As the above-mentioned acid curing resin component, a mixture of a crosslinking resin and a crosslinking agent can also be used. As the above-mentioned crosslinking resin, for example, polyhydroxystyrene and its derivatives can be listed; polyacrylic acid and its derivatives; polymethacrylic acid and its derivatives; two or more copolymers formed by being selected from hydroxystyrene, acrylic acid, methacrylic acid and their derivatives; two or more copolymers formed by being selected from hydroxystyrene, styrene and their derivatives; three or more copolymers selected from cycloolefins and their derivatives, maleic anhydride, and acrylic acid and its derivatives; three or more copolymers selected from cycloolefins and their derivatives, maleimide, and acrylic acid and its derivatives; polynorbornene; one or more polymers selected from the group consisting of metathesis ring-opening polymers; polymers having alkoxysilyl groups; polymers obtained by partially replacing acid-labile groups with alkali dissolution control ability in these polymers, etc. As polymers containing structural units from hydroxystyrene, such as the above-mentioned polyhydroxystyrene, for example, resins (QN) containing phenolic hydroxyl groups described in Japanese Patent Application Publication No. 2018-112670 can also be cited. In this document, examples of QN include novolac resins, polyhydroxystyrene, copolymers of hydroxystyrene, copolymers of hydroxystyrene and styrene, copolymers of hydroxystyrene, styrene and (meth)acrylic acid derivatives, phenol-benzenedimethanol condensation resins, cresol-benzenedimethanol condensation resins, polyimides containing phenolic hydroxyl groups, polyamic acids containing phenolic hydroxyl groups, and phenol-dicyclopentadiene condensation resins.

[0371] As the cross-linking resin, for example, the resist base resin described in International Publication No. 2017 / 130896, the resin described in Japanese Patent Application Laid-Open No. 2003-192665 whose solubility in the alkaline developer changes under the action of the acid of component (A), claim 3 of Japanese Patent Application Laid-Open No. 2004-323704, and the resin described as an alkali-soluble resin described in Japanese Patent Application Laid-Open No. 10-10733 can also be used.

[0372] As the polymer having an alkoxysilyl group, for example, a compound in which the alkoxysilyl group is not directly bonded to an aromatic ring can be used.

[0373] The crosslinking agent may be any crosslinking agent capable of crosslinking the crosslinkable resins in the presence of an acid. Examples of such crosslinking agents include epoxy-containing compounds, hydroxyl-containing compounds, alkoxy-containing compounds, methylol-containing compounds, and carboxymethyl-containing compounds, which react with acidic groups such as phenolic hydroxyl groups and carboxyl groups contained in the resins in the presence of an acid.

[0374] More specifically, examples of the cross-linking agent include those described in JP-A-2016-169173 and JP-A-2018-112670.

[0375] The acid-decomposable resin component may be any acid-decomposable resin component whose solubility in a developer is increased by the acid generated from compound A. Examples thereof include resins having acidic groups such as phenolic hydroxyl groups, carboxyl groups, sulfonyl groups, and silanol groups, in which some or all of the hydrogen atoms of the acidic groups are protected with protecting groups.

[0376] As such a resin having an acidic group, for example, a crosslinking resin used as the above-mentioned acid curable resin component together with a crosslinking agent can be mentioned. Positive chemically amplified resins described in Japanese Patent Application Laid-Open No. 2018-112670 can also be used.

[0377] As the above-mentioned protecting group, as long as the above-mentioned acidic group can be protected, for example, the acid dissociation property group recorded in the protecting group described in Japanese Unexamined Patent Publication No. 2016-169173, the acid unstable group described in International Publication No. 2017 / 130896, the acid dissociation property group described in Japanese Unexamined Patent Publication No. 2018-112670 etc. can be enumerated. In addition, as the group protected by the above-mentioned silanol group protected group, alkoxysilyl can be enumerated. As the polymer with alkoxysilyl as acid-decomposable resin component, for example, " having the structural unit (I) comprising an aromatic ring and the alkoxysilyl directly bonded to the aromatic ring and the polymer component (A) comprising the structural unit (II) of an acidic group" described in Japanese Unexamined Patent Publication No. 2019-66828 can be used.

[0378] Examples of the developer include the developer described in the section "F. Pattern production method" described later.

[0379] In addition to acid-curable resin components and acid-decomposable resin components, the acid-reactive resin component may also include components that react with acid. For example, a resin having an alkali-soluble group that is insolubilized by acid may be used. Specifically, examples include acid-insolubilized resins that undergo dehydration condensation with an acid catalyst between a hydroxyl group and a carboxyl group, or between carboxyl groups as exemplified below, to produce intramolecular or intermolecular crosslinking reactions. Examples of acid-insolubilized resins that undergo dehydration condensation with an acid catalyst between carboxyl groups include, for example, resins having a phthalic acid structure in which carboxyl groups undergo dehydration condensation with an acid, as shown below.

[0380] [Chemical Formula 21]

[0381]

[0382] As the above-mentioned non-acid-reactive resin component, a substance that does not react with the acid generated by compound A can be used. More specifically, a substance that does not undergo solidification, decomposition, or changes in solubility in alkaline developer due to the acid generated from compound A can be used. Examples of the non-acid-reactive resin component include thermoplastic resins such as polyolefin resins, polybutadiene resins, polystyrene resins, polystyrene / butadiene resins, and polystyrene / olefin resins.

[0383] The content of the resin component in the composition B of the present invention may be appropriately set as long as a predetermined effect can be obtained depending on the type of the resin component used.

[0384] The content of the resin component in composition B can be 10 parts by mass or more, preferably 15 parts by mass or more and 99.9 parts by mass or less, and more preferably 20 parts by mass or more and 99 parts by mass or less, based on 100 parts by mass of the solid content of composition B.

[0385] This is because the composition B can induce excellent curing reaction and decomposition reaction by the acid generated by the efficient decomposition of the compound A.

[0386] The content of the resin component in the composition B of the present invention may be, for example, 10 parts by mass or more, more preferably 15 parts by mass or more and 99.9 parts by mass or less, and particularly preferably 20 parts by mass or more and 96 parts by mass or less, based on 100 parts by mass of the composition B.

[0387] This is because the composition B can induce excellent curing reaction and decomposition reaction by the acid generated by the efficient decomposition of the compound A.

[0388] 3. Solvent

[0389] The above-mentioned composition B may contain a solvent.

[0390] The solvent can disperse or dissolve the components in the composition. Therefore, even if it is liquid at room temperature (25°C) and atmospheric pressure, the compound A and the resin component are not contained in the solvent. As the solvent, either water or an organic solvent can be used.

[0391] In the present invention, the solvent is preferably an organic solvent because it can easily dissolve or disperse the compound A.

[0392] Examples of the organic solvent include carbonates such as propylene carbonate and diethyl carbonate; ketones such as acetone and 2-heptanone; polyols such as monomethyl ether or monophenyl ether of ethylene glycol, propylene glycol, propylene glycol monoacetate, dipropylene glycol, and dipropylene glycol monoacetate, and their derivatives; cyclic ethers such as dioxane; esters such as ethyl formate and 3-methyl-3-methoxybutyl acetate; aromatic hydrocarbons such as toluene and xylene; lactones such as γ-caprolactone and δ-caprolactone, etc.

[0393] The content of the solvent in the composition B of the present invention can be appropriately set depending on the application of the composition B, and can be, for example, 1 part by mass or more and 99 parts by mass or less per 100 parts by mass of the composition.

[0394] 4. Other ingredients

[0395] The composition B may contain other ingredients as needed.

[0396] Such other components can be selected according to the purpose of the composition, for example, benzotriazole, triazine, benzoate-based ultraviolet absorbers; phenolic, phosphorus, sulfur-based antioxidants; antistatic agents composed of cationic surfactants, anionic surfactants, nonionic surfactants, amphoteric surfactants, etc.; halogen compounds, phosphate ester compounds, phosphoric acid amide compounds, melamine compounds, fluororesins or metal oxides, (poly) melamine phosphate, (poly) piperazine phosphate and other flame retardants; hydrocarbons, fatty acids Lubricants of the aliphatic alcohol, aliphatic ester, aliphatic amide or metal soap series; colorants such as dyes, pigments, and carbon black; inorganic silicic acid additives such as fumed silica, particulate silica, silica, diatomaceous earth, clay, kaolin, diatomaceous earth, silica gel, calcium silicate, sericite, kaolinite, flint, feldspar powder, vermiculite, attapulgite, talc, mica, talc, pyrophyllite, and silicon dioxide; fillers such as glass fiber and calcium carbonate; crystallization agents such as nucleating agents and crystallization accelerators, rubber elasticity imparting agents such as silane coupling agents and flexible polymers, and sensitizers.

[0397] Unless the predetermined effect is impaired, an acid generator other than the compound A may be contained.

[0398] Furthermore, the above-mentioned other components may also include acid diffusion control agents such as amine compounds, amide group-containing compounds, urea compounds, and nitrogen-containing heterocyclic compounds.

[0399] Examples of the sensitizer include compounds described as spectrophotosensitizers in JP-A-2008-506749.

[0400] Examples of the acid diffusion controller include compounds described as “[D] Acid Diffusion Controller” in JP-A-2019-8300.

[0401] The content of these other components in the composition of the present invention can be 50 parts by mass or less based on 100 parts by mass of the composition.

[0402] 5. Others

[0403] As a method for producing the composition B, any known method may be used as long as the above-mentioned components can be mixed in desired blending amounts.

[0404] For example, there can be mentioned a method in which the compound A is dissolved or dispersed in a solvent and then the resin component is added to the solvent.

[0405] C. Cured material

[0406] The cured product of the present invention (hereinafter, sometimes referred to as "cured product C") is a cured product of the composition B described above.

[0407] In addition, the resin component contained in the above-mentioned composition B is an acid-curable resin component.

[0408] This is because, according to the present invention, by using the composition B, the compound A is efficiently decomposed to generate an acid, thereby inducing an excellent curing reaction.

[0409] 1. Composition

[0410] As for the composition B, the same composition as that described in the above-mentioned "B. Composition" can be used, and therefore the description here is omitted.

[0411] The resin component is an acid-curable resin component, and the cured product C is formed by curing the acid-curable component, and includes a polymer formed by polymerizing the acid-curable components or a crosslinked product formed by crosslinking.

[0412] The planar shape of the cured product C can be appropriately set according to the intended use of the cured product, and may be, for example, a pattern such as a dot shape or a line shape.

[0413] The uses of the cured product C may be the same as those described in the above section "A. Compound".

[0414] The method for producing the cured product C is not particularly limited as long as it is a method that can form the cured product of the composition B into a desired shape.

[0415] As such a production method, for example, the production method described in the section "D. Production method of cured product" described later can be used.

[0416] D. Method for producing cured product

[0417] The method for producing the cured product C of the present invention will be described.

[0418] One of the characteristics of the method for producing the cured product C of the present invention is that it comprises a curing step of curing the composition B.

[0419] In addition, the resin component contained in the above-mentioned composition B is an acid-curable resin component.

[0420] According to the present invention, by using the composition B, compound A is efficiently decomposed to generate an acid, thereby inducing an excellent curing reaction and easily forming a cured product in which the acid-curable resin component is sufficiently cured.

[0421] 1. Curing process

[0422] The curing step in the present invention is a step of curing the composition B described above.

[0423] As a method for curing the composition B, any method may be used as long as the acid-curable resin component can be cured, and a method in which the compound A generates an acid may be used.

[0424] As a method for generating an acid from Compound A, any method can be used as long as Compound A decomposes to generate a desired amount of acid. Examples include methods of irradiating with energy rays, methods of performing a heat treatment, and methods of performing these simultaneously or sequentially. Regarding such methods of irradiating with energy rays and performing a heat treatment, the same methods as those described in the section "A. Compound" above can be used.

[0425] In this step, the method for generating acid preferably includes irradiation with energy rays because the compound A has excellent light absorption and photodecomposition rate, and thus can generate acid efficiently.

[0426] The composition B contains an acid curable resin component as a resin component. The contents of such a composition may be the same as those described in the above section "B. Composition", and therefore, description thereof will be omitted here.

[0427] 2. Other processes

[0428] The method for producing the cured product C of the present invention may include other steps as needed in addition to the above-mentioned curing step.

[0429] Examples of the other steps include a development step for removing unpolymerized portions in the coating film of the composition after the curing step to obtain a patterned cured product, a post-baking step for heat-treating the cured product after the curing step, a pre-baking step for heat-treating the composition before the curing step to remove the solvent in the composition, and a step for forming a coating film of the composition before the curing step.

[0430] In the present invention, it is preferred that the above-mentioned other steps include a post-baking step because the acid generated from the compound A can be efficiently diffused, and a cured product in which the acid-curable resin component is sufficiently cured can be easily formed.

[0431] As a method of removing the unpolymerized portion in the above-mentioned development step, for example, there is a method of applying a developer such as an alkaline developer to the unpolymerized portion.

[0432] As the alkali developer, a developer generally used as an alkali developer, such as a tetramethylammonium hydroxide (TMAH) aqueous solution, a potassium hydroxide aqueous solution, or a potassium carbonate aqueous solution, can be used.

[0433] In addition, as a developer, a developer commonly used as a solvent developer such as propylene glycol monomethyl ether acetate (PEGMEA) or cyclohexanone can be used. As a development method using the above-mentioned developer, any method that can bring the area to be developed into contact with the developer can be used, and a known method such as a shower method, a spray method, or an immersion method can be used.

[0434] The development step may be performed after the curing step.

[0435] The heating conditions in the post-baking step may be any conditions that can improve the strength of the cured product obtained in the curing step, and can be, for example, 200° C. to 250° C. for 20 to 90 minutes.

[0436] The heating conditions in the pre-baking step are any conditions that can remove the solvent in the composition, and can be, for example, 70°C to 150°C for 30 to 300 seconds. In the step of forming the coating film, the composition can be applied using known methods such as a spin coater, a roll coater, a bar coater, a die coater, a curtain coater, various printing methods, and dipping.

[0437] The above-mentioned coating film can be formed on a substrate.

[0438] The substrate can be appropriately selected depending on the intended use of the cured product, and examples thereof include substrates made of soda glass, quartz glass, semiconductor substrates, wiring boards, metals, paper, and plastics.

[0439] Furthermore, after the cured product is formed on the substrate, it can be peeled from the substrate for use, or it can be transferred from the substrate to another adherend for use.

[0440] E. Pattern

[0441] The pattern of the present invention comprises composition B described above.

[0442] In addition, the resin component contained in the above-mentioned composition B is an acid-decomposable resin component.

[0443] According to the present invention, by using the aforementioned composition B, compound A efficiently decomposes to generate acid, thereby inducing an excellent decomposition reaction and facilitating the decomposition of the acid-decomposable resin component. As a result, only the acid-decomposable resin component is precisely decomposed and removed by solvent washing or the like, while any remaining undecomposed resin can be formed into a pattern with excellent dimensional accuracy.

[0444] The pattern of the present invention uses the composition B. In addition, the resin component is an acid-decomposable resin component. The pattern is formed by forming a coating film using the composition B and removing unnecessary portions.

[0445] The contents of such a composition may be the same as those described in the above-mentioned section "B. Composition", and therefore the description here is omitted.

[0446] The planar shape of the pattern can be appropriately set according to the application of the pattern, and can be, for example, a pattern such as a dot shape or a line shape.

[0447] The use of the above pattern may be the same as that described in the above section "A. Compound".

[0448] The method for producing the pattern is not particularly limited as long as it is a method that can form the composition B into a desired shape.

[0449] As such a production method, for example, the production method described in the section "F. Production method of pattern" described later can be used.

[0450] F. Pattern Manufacturing Method

[0451] Next, the method for producing a pattern of the present invention will be described.

[0452] The method for producing a pattern of the present invention comprises the following steps: forming a coating film using the composition B, generating an acid from the compound A contained in the formed coating film; and developing a portion of the coating film after the acid generation from the compound A to form a pattern. The resin component contained in the composition B is an acid-decomposable resin component.

[0453] According to the present invention, by using the above-mentioned composition B, compound A is efficiently decomposed to generate acid, thereby inducing an excellent decomposition reaction and facilitating the decomposition of the acid-degradable component. As a result, a pattern with excellent dimensional accuracy can be easily formed.

[0454] 1. Acid-generating process

[0455] The step of generating an acid in the present invention is a step of generating an acid from the compound A contained in the coating film formed using the composition B.

[0456] In this step, any method for generating an acid from Compound A can be used as long as Compound A decomposes to generate a desired amount of acid. Examples include irradiation with energy rays, heat treatment, and simultaneous or sequential methods. Examples of such irradiation with energy rays and heat treatment methods include the same methods as those described in the section "A. Compound" above.

[0457] In this step, the method for generating the acid preferably includes irradiation with energy rays. This is because Compound A has excellent light absorption and a high photodecomposition rate, allowing efficient acid generation and an excellent decomposition reaction to occur, facilitating the decomposition of acid-degradable components. As a result, patterns with excellent dimensional accuracy can be easily formed.

[0458] In addition, in this process, the portion of the coating film where acid is generated is preferably a portion of the coating film when viewed from above. This is because it facilitates the patterning process described later. The top view shape and thickness of the coating film can be appropriately set according to the purpose of the patterned coating film.

[0459] The composition B contains an acid-decomposable resin component as a resin component. The contents of such a composition may be the same as those described in the above-mentioned section "B. Composition", and therefore, description thereof will be omitted here.

[0460] 2. Pattern formation process

[0461] The patterning step in the present invention is a step of generating an acid from the compound A and then developing a portion of the coating film to form a pattern.

[0462] As a development method in this step, a method of developing using a developer can be mentioned.

[0463] Such a developer and a developing method may be the same as those described in the above-mentioned section "D. Method for producing a cured product".

[0464] 3. Other processes

[0465] The method for producing a pattern of the present invention includes the above-mentioned step of generating an acid and the step of forming a pattern, but may also include other steps as necessary.

[0466] Examples of such other steps include a step of forming a coating film of the composition B before the step of generating an acid, and a pre-baking step of performing a heat treatment after the step of forming the coating film to remove the solvent in the coating film.

[0467] In the present invention, it is preferred that the above-mentioned other steps include a post-exposure baking step because the acid generated from compound A can be efficiently diffused, thereby enabling more efficient decomposition of the acid-decomposable component.

[0468] The steps of forming the coating film and pre-baking may be the same as those described in the above section "D. Method for producing a cured product".

[0469] The conditions for the post-exposure bake step may be, for example, 70° C. or higher and 150° C. or lower, and 30 seconds to 300 seconds.

[0470] 4. Others

[0471] The pattern produced by the above production method and its uses, etc. may be the same as those described in the above section "A. Compound".

[0472] The present invention is not limited to the above-described embodiments. The above-described embodiments are merely illustrative, and any technical solution having substantially the same structure and achieving the same function and effect as the technical concept described in the claims of the present invention is encompassed within the technical scope of the present invention.

[0473] Example

[0474] Hereinafter, the present disclosure will be described in more detail with reference to Examples and the like, but the present disclosure is not limited to these Examples.

[0475] [Example 1]

[0476] In a 1L four-necked flask, 65g (332mmol) of ethylcarbazole, 223g of MCB (monochlorobenzene), and 31.6g (432mmol) of DMF (dimethylformamide) were added and stirred at room temperature. 76.6g (500mmol) of phosphorus oxychloride was added dropwise thereto. The mixture was heated and stirred at 80°C on an oil bath for 4 hours. After cooling to room temperature, the reaction solution was poured into ion-exchanged water for oil-water separation. After washing with ion-exchanged water four times, the organic layer was concentrated to obtain 56.8g of the target intermediate 1-A in the form of a light yellow oil with a yield of 77%.

[0477] [Chemical Formula 22]

[0478]

[0479] 50 g (224 mmol) of Intermediate 1-A and 183 g of DMAC (dimethylacetamide) were added to a 1L four-necked flask and stirred at room temperature. 28 g (224 mmol) of 2-aminothiophenol was added dropwise. The mixture was heated and stirred at 120°C on an oil bath for 14 hours. After cooling to room temperature, ion-exchanged water and ethyl acetate were added to the reaction mixture to separate the oil and water. After washing three times with ion-exchanged water, ethyl acetate was added to the solid from the concentrated organic layer, washed, filtered, and dried to obtain 35 g of the target Intermediate 1-B as pale yellow crystals in a yield of 47.6%.

[0480] [Chemical Formula 23]

[0481]

[0482] In a 200mL four-necked flask, 12g (37mmol) of intermediate 1-B and 60g of DCM (dichloromethane) were added and stirred on an ice bath at below 10°C. 15g (113mmol) of aluminum chloride was added to the mixture while paying attention to the heat generation. Cool the mixture to below 10°C again and add 11.5g (55mmol) of trifluoroacetic anhydride dropwise. After warming to room temperature, stir for 3 hours. The reaction solution was injected into ion exchange water for oil-water separation. After washing with ion exchange water 3 times, ethyl acetate was added to the solid of the concentrated organic layer, filtered after washing, and dried to obtain 12.3g of the target intermediate 1-C in the form of light yellow crystals with a yield of 79.3%.

[0483] [Chemical Formula 24]

[0484]

[0485] To a 200 mL four-necked flask were added 10 g (24 mmol) of Intermediate 1-C, 2.5 g (35 mmol) of hydroxylamine hydrochloride, 2.25 g (28 mmol) of pyridine, and 51.8 g of dimethylacetamide. The mixture was heated and stirred at 80°C in an oil bath for 1 hour. After cooling to room temperature, dichloromethane and water were added to the reaction mixture to separate the oil and water. After washing three times with ion-exchanged water, ethyl acetate was added to the solid from the concentrated organic layer. After washing, the solid was filtered and dried to obtain 7.45 g of the target Intermediate 1-D as pale yellow crystals with a yield of 72%.

[0486] [Chemical Formula 25]

[0487]

[0488] 6.6g (15mmol) of intermediate 1-D, 60g of dichloromethane and 2.4g (30mmol) of pyridine were added to a 200mL four-necked flask and stirred below 10°C on an ice bath. 6.36g (23mmol) of trifluoromethanesulfonic anhydride was added dropwise thereto at a temperature not exceeding 10°C. After the addition was completed, the mixture was stirred at room temperature for 2 hours. The reaction solution was poured into ice water, and after oil-water separation, it was washed 3 times with ion-exchanged water. Dichloromethane was added to the solid of the concentrated organic layer, and methanol was added while stirring for washing. The solid was filtered and dried to obtain 6.9g of the target compound 1 with a yield of 80.3%. 1 H-NMR and 19 Tables 1 and 2 show the results of F-NMR measurements.

[0489] [Chemical Formula 26]

[0490]

[0491] Table 1

[0492]

[0493] Table 2

[0494]

[0495] [Comparative Example 1] Comparative Compound 1

[0496] [Chemical Formula 27]

[0497]

[0498] [Comparative Example 2] Comparative Compound 2

[0499] [Chemical Formula 28]

[0500]

[0501] [evaluate]

[0502] 1. Light absorption coefficient

[0503] Measure 1.0×10 -4 The compound obtained in Example 1 and comparative compounds 1 and 2 were diluted to volume with acetonitrile and further diluted to 1 / 10 to prepare 1.0×10 -4 The absorption spectrum of this solution was measured using an ultraviolet-visible spectrophotometer (U-3010 manufactured by Hitachi High-Tech Science Co., Ltd.), and the molar absorption coefficient (ε) at 365 nm was calculated.

[0504] 2. Photodecomposition rate

[0505] The solution prepared in the absorbance measurement was sealed in a 1 cm square cuvette with a screw cap and a UV LED light source (365 nm: 20 mW / cm 2 ), with an exposure of 20 mW / cm 2 The exposure solution was measured by HPLC, and the photodecomposition rate (%) was calculated according to the following formula.

[0506] As the HPLC conditions, the peak areas of the compounds in the solution before and after exposure were measured as follows.

[0507] Measuring device: HITACHI High-Tech Science Co., Ltd. (trade name "Chromaster")

[0508] Column: Inertsustain C18 (4.6mm ID x 250mm)

[0509] Eluent: acetonitrile / water (20 mM OSA) = 80 / 20

[0510] Flow rate: 1 mL / min

[0511] Injection volume: 10 μL

[0512] Column temperature: 40°C

[0513] Detection: Chromaster 5430 Diode Array Detector (HITACHI High-TechScience)

[0514] In addition, OSA refers to sodium 1-octane sulfonate.

[0515] Photodecomposition rate (%) = 100 - peak area of ​​compound after exposure / peak area of ​​compound before exposure × 100

[0516] A compound with a higher photodecomposition rate (%) has a more excellent acid generation sensitivity.

[0517] Table 3

[0518] Example 1 Comparative Example 1 Comparative Example 2 ε(365nm) 22100 11000 656 Photodecomposition rate (%) 87.5 54.3 3

[0519] The compound of the present invention having a specific structure is excellent in light absorption and photodecomposition rate.

Claims

1. A compound having at least one structure selected from the group consisting of the structure represented by the following general formula (II) and the structure represented by the following general formula (I-II), the structure represented by the following general formula (II), and the structure represented by the following general formula (III), Where, X 1 and X 2 Each independently represents a direct bond, C(R 101 )2, O, CO, S or NR 102 , Y 1 Each independently represents C(R 201 )2, O, CO, S, N or NR 202 , in, Y 1 When N, a double bond is formed as shown by the dotted line in formula (II). Y 2 Each independently represents C(R 201 )2, O, CO, S or NR 202 , R 101 and R 102 each independently represents a hydrogen atom, a halogen atom, a cyano group, an amino group, a hydroxyl group, a nitro group, a carboxyl group, a hydrocarbon group having 1 to 20 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms, R 101 and R 102 The hydrocarbon group and heterocyclic group used in the group are groups in which the hydrogen atoms are not substituted, or one or more of the hydrogen atoms are substituted by a halogen atom, a cyano group, a nitro group, a hydroxyl group, a thiol group, -COOH, -SO3H, an isocyanate group or an alkyl group having 1 to 4 carbon atoms, and One or more methylene groups in the group may be substituted by a divalent group selected from the following group I, R 201 and R 202 are each independently a hydrogen atom, a halogen atom, a cyano group, an amino group, a hydroxyl group, a nitro group, a carboxyl group, a hydrocarbon group having 1 to 20 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms, R 201 and R 202 The hydrocarbon group and heterocyclic group used in the group are groups in which the hydrogen atoms are not substituted, or one or more of the hydrogen atoms are substituted by a halogen atom, a cyano group, a nitro group, a hydroxyl group, a thiol group, -COOH, -SO3H, an isocyanate group or an alkyl group having 1 to 4 carbon atoms, and One or more methylene groups in the group may be substituted by a divalent group selected from the following group I, R 31 represents a hydrocarbon group having 1 to 20 carbon atoms or a heterocyclic group having 2 to 20 carbon atoms, R 32 is a hydrogen atom, a halogen atom, a nitro group, a cyano group, a hydrocarbon group having 1 to 20 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms, R 31 and R 32 The hydrocarbon group and heterocyclic group used in the group are groups in which the hydrogen atoms are not substituted, or one or more of the hydrogen atoms are substituted by a halogen atom, a cyano group, a nitro group, a hydroxyl group, a thiol group, -COOH, -SO3H, an isocyanate group or an alkyl group having 1 to 4 carbon atoms, and One or more methylene groups in the group may be substituted by a divalent group selected from the following group I, n represents 0 or 1, *Indicates the bonding site, Group I: -O-, -COO-, -OCO-, -CO-, -CS-, -S-, -SO-, -SO2-, -NR 33 -、-NR 33 -CO-, -CO-NR 33 -、-NR 33 -COO-, -OCO-NR 33 -or-SiR 33 R 34 -, R 33 and R 34 Each independently represents a hydrogen atom, an unsubstituted hydrocarbon group having 1 to 10 carbon atoms, or a heterocyclic group having 2 to 10 carbon atoms, The structure represented by formula (II) or the structure represented by formula (I-II) is bonded to the structure represented by formula (II) directly or via a linking group, and further, one or more hydrogen atoms in the structures of formula (II), formula (I-II), formula (II) and the linking group may be substituted by groups other than hydrogen atoms.

2. The compound according to claim 1, wherein The compound is represented by the following general formula (IIA) or (I-II-A), Where, X 1A and X 2A Each independently represents a direct bond, C(R 101A )2, O, CO, S or NR 102A , R 101A and R 102A each independently represents a hydrogen atom, a halogen atom, a cyano group, an amino group, a hydroxyl group, a nitro group, a carboxyl group, a hydrocarbon group having 1 to 20 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms, R 101A and R 102A The hydrocarbon group and heterocyclic group used in the group are groups in which the hydrogen atoms are not substituted, or one or more of the hydrogen atoms are substituted by a halogen atom, a cyano group, a nitro group, a hydroxyl group, a thiol group, -COOH, -SO3H, an isocyanate group or an alkyl group having 1 to 4 carbon atoms, and One or more methylene groups in the group may be substituted by a divalent group selected from the following group I, R 1 、R 2 、R 3 、R 4 、R 9 and R 10 Each independently represents a hydrogen atom, a halogen atom, a cyano group, an amino group, a hydroxyl group, a nitro group, a carboxyl group, a hydrocarbon group having 1 to 20 carbon atoms, a heterocyclic group having 2 to 20 carbon atoms, or a group represented by the following general formula (IV), R 5 、R 6 、R 7 、R 8 、R 11 、R 12 、R 13 and R 14 Each independently represents a hydrogen atom, a halogen atom, a cyano group, an amino group, a hydroxyl group, a nitro group, a carboxyl group, a hydrocarbon group having 1 to 20 carbon atoms, a heterocyclic group having 2 to 20 carbon atoms, or a group represented by the following general formula (III-A), R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 10 、R 11 、R 12 、R 13 and R 14 The hydrocarbon group and heterocyclic group used in the group are groups in which the hydrogen atoms are not substituted, or one or more of the hydrogen atoms are substituted by a halogen atom, a cyano group, a nitro group, a hydroxyl group, a thiol group, -COOH, -SO3H, an isocyanate group or an alkyl group having 1 to 4 carbon atoms, and One or more methylene groups in the group may be substituted by a divalent group selected from the following group I, R 1 、R 2 、R 3 and R 4 At least one of represents a group represented by the following general formula (IV), R 5 、R 6 、R 7 and R 8 At least one of them represents a group represented by the following general formula (III-A), R 9 and R 10 At least one of them represents a group represented by the following general formula (IV), R 11 、R 12 、R 13 and R 14 At least one of them represents a group represented by the following general formula (III-A), R 31A represents a hydrocarbon group having 1 to 20 carbon atoms or a heterocyclic group having 2 to 20 carbon atoms, R 32A represents a hydrogen atom, a halogen atom, a nitro group, a cyano group, a hydrocarbon group having 1 to 20 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms, R 31A and R 32A The hydrocarbon group and heterocyclic ring-containing group used in the group are groups in which the hydrogen atoms in the group are not substituted, or one or more hydrogen atoms in the group are substituted by halogen atoms, cyano groups, nitro groups, hydroxyl groups, thiol groups, -COOH groups, -SO3H groups, isocyanate groups or alkyl groups having 1 to 4 carbon atoms, and One or more methylene groups in the group may be substituted by a divalent group selected from the following group I, n represents 0 or 1, *Indicates the bonding site, *-R 41 -R 42 (IV) R 41 Each independently represents a direct bond, a divalent group selected from the following Group I, a hydrocarbon group having 1 to 20 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms, R 41 The hydrocarbon group and heterocyclic group used in the group are groups in which the hydrogen atoms are not substituted, or one or more of the hydrogen atoms are substituted by a halogen atom, a cyano group, a nitro group, a hydroxyl group, a thiol group, -COOH, -SO3H, an isocyanate group or an alkyl group having 1 to 4 carbon atoms, and One or more methylene groups in the group may be substituted by a divalent group selected from the following group I, R 42 represents a group represented by any one of the following general formulas (II-A-1), (II-A-2) or (II-A-3), *Indicates the bonding site, [Chemical Formula 5] Y 1A 、Y 1A-2 and Y 1A-3 Each independently represents C(R 201A )2, O, CO, S, N or NR 202A , Among them, Y 1A 、Y 1A-2 and Y 1A-3 When N, a double bond is formed as shown by the dotted line in formula (II). Y 2A 、Y 2A-2 and Y 2A-3 Each independently represents C(R 201A )2, O, CO, S or NR 202A , R 201A and R 202A each independently represents a hydrogen atom, a halogen atom, a cyano group, an amino group, a hydroxyl group, a nitro group, a carboxyl group, a hydrocarbon group having 1 to 20 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms, R 201A and R 202A The hydrocarbon group and heterocyclic group used in the group are groups in which the hydrogen atoms are not substituted, or one or more of the hydrogen atoms are substituted by a halogen atom, a cyano group, a nitro group, a hydroxyl group, a thiol group, -COOH, -SO3H, an isocyanate group or an alkyl group having 1 to 4 carbon atoms, and One or more methylene groups in the group may be substituted by a divalent group selected from the following group I, R 21 、R 22 、R 23 、R 24 、R 22-2 、R 23-2 、R 24-2 、R 25-2 、R 21-3 、R 23-3 、R 24-3 and R 25-3 each independently represents a hydrogen atom, a halogen atom, a cyano group, an amino group, a hydroxyl group, a nitro group, a carboxyl group, a hydrocarbon group having 1 to 20 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms, R 21 、R 22 、R 23 、R 24 、R 22-2 、R 23-2 、R 24-2 、R 25-2 、R 21-3 、R 23-3 、R 24-3 and R 25-3 The hydrocarbon group and heterocyclic group used in the group are groups in which the hydrogen atoms are not substituted, or one or more of the hydrogen atoms are substituted by halogen atoms, cyano groups, nitro groups, hydroxyl groups, thiol groups, -COOH groups, -SO3H groups, isocyanate groups or alkyl groups having 1 to 4 carbon atoms, and One or more methylene groups in the group may be substituted by a divalent group selected from the following group I, * indicates the same as R 41 The bonding site, Group I: -O-, -COO-, -OCO-, -CO-, -CS-, -S-, -SO-, -SO2-, -NR 33 -、-NR 33 -CO-, -CO-NR 33 -、-NR 33 -COO-, -OCO-NR 33 -or-SiR 33 R 34 -, R 33 and R 34 Each independently represents a hydrogen atom, an unsubstituted hydrocarbon group having 1 to 10 carbon atoms, or an unsubstituted heterocyclic group having 2 to 10 carbon atoms.

3. The compound according to claim 2, wherein The compound is represented by the general formula (IIA), wherein X 2A For direct bonding.

4. The compound according to claim 2 or 3, wherein The X 1A C(R 101A )2, O, S or NR 102A .

5. The compound according to claim 2 or 3, wherein The R 41 For direct bonding.

6. The compound according to claim 2 or 3, wherein The R 42 It is a group represented by formula (II-A-1).

7. The compound according to claim 2 or 3, wherein The R 2 and R 9 is a group represented by formula (IV), The R 7 and R 13 It is a group represented by formula (III-A).

8. The compound according to claim 2 or 3, wherein The R 31A An alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aralkyl group having 7 to 10 carbon atoms, a 10-camphoryl group, or a group in which one or two or more hydrogen atoms of the alkyl group, the aryl group, the aralkyl group, or the 10-camphoryl group are substituted with halogen atoms.

9. The compound according to claim 2 or 3, wherein The R 32A It is a halogenated alkyl group having 1 to 10 carbon atoms.

10. A composition comprising: The compound according to claim 1 or 2, and Resin composition.

11. The composition according to claim 10, wherein The resin component is an acid-curable resin component.

12. A cured product of the composition according to claim 11.

13. The composition according to claim 10, wherein The resin component is an acid-decomposable resin component.

14. A pattern comprising the composition of claim 13.

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