JP2007262263A - Phthalocyanine compound - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a phthalocyanine compound that has absorption in the near infrared region, good solubility and excellent light resistance. <P>SOLUTION: The phthalocyanine compound is represented by general formula (I), wherein R<SP>10</SP>is an atomic group making a spectral absorption maximum wavelength in a solution of the compound 470 nm or shorter within the range of 270 to 750 nm; L<SP>10</SP>is a single bond or a bivalent group; n10 is an integer of 1-16; R<SP>11</SP>-R<SP>14</SP>are each a substituent group other than (L<SP>10</SP>-R<SP>10</SP>); n11-n14 are each an integer of 0-4; and M<SP>1</SP>is a hydrogen atom and/or a metal atom. <P>COPYRIGHT: (C)2008,JPO&INPIT

Description

  The present invention relates to a phthalocyanine compound serving as a near-infrared absorbing material. More specifically, the present invention relates to a near-infrared absorbing filter, a near-infrared absorbing colored resin composition, a liquid crystal display element, an optical card, an optical recording medium, protective glasses, etc. The present invention relates to a near-infrared absorbing compound that plays an important role in materials and products and achieves both light resistance and other properties required for other phthalocyanine compounds.

  Near-infrared absorbing dyes that do not substantially absorb visible light but absorb infrared rays are used in various optoelectronic products such as near-infrared absorbing filters. These are exposed to high temperature, high humidity, or light irradiation conditions depending on the production process and usage, and the decomposition thereof may be a problem.

As a technique for improving resistance to these by changing the structure of the dye, for example, a naphthalocyanine dye having a specific structure (for example, Patent Documents 1 to 3) has been found to be good. It was difficult to achieve compatibility with other physical properties such as properties. In particular, suppression of light degradation of the phthalocyanine compound and other physical properties are desired (for example, Patent Document 4). Moreover, although the technique which suppresses decomposition | disassembly by light by using a near-infrared absorption pigment | dye and ultraviolet-ray absorption material together was known (for example, patent document 5, 6), the degree of the suppression is inadequate, and further light resistance, A technique for improving durability was desired.
Japanese Laid-Open Patent Publication No. 2-4685 JP-A-2-43269 JP-A-2-138382 Japanese Patent Laid-Open No. 11-152413 JP-A-10-77360 JP 2005-181966 A

  In view of the above problems of the prior art, an object of the present invention is to provide a new phthalocyanine compound having improved light resistance without impairing the physical properties of phthalocyanine compounds.

  As a result of intensive studies, the present inventors have found that a phthalocyanine compound having a specific structure can solve the problems of the prior art. That is, the following present invention has been provided as means for solving the problems.

(1) A phthalocyanine compound represented by the general formula (I).

In general formula (I), R ¹⁰ has a spectral absorption maximum wavelength at 270 to 750 nm in a solution of compound R ¹⁰ -H of 470 nm or less, or compound R ¹⁰ -H is a singlet oxygen scavenger, radical trap Represents an atomic group satisfying the condition of being an agent or an antioxidant, L ¹⁰ represents a single bond or a divalent group, n10 represents an integer of 1 to 16, and when n10 is 2 or more, each L ¹⁰ , R ¹⁰ may be the same or different. (L ¹⁰ -R ¹⁰ ) is substituted at a substitutable position in the structure in []. R ¹¹ to R ¹⁴ each independently represent a (L ¹⁰ -R ¹⁰⁾ other than the substituent each independently represent an integer of 0 to 4 N11～n14. When n11 to n14 is 2 or more, adjacent R ^{11 to} R ¹⁴ may be connected to each other to form a ring. M ¹ represents two atoms selected from the group consisting of a hydrogen atom and a monovalent metal atom, a divalent metal atom, or a divalent substituted metal atom including a trivalent or tetravalent metal atom.

(2) The compound according to (1) above, wherein R ^{10 in the} general formula (I) is a group represented by any of the following structural formulas.

In general formula (II-1), R ²⁰¹¹ represents a hydrogen atom, an aliphatic group, an aromatic group, a heterocyclic group bonded by a carbon atom or a hydrolyzable protecting group, R ²⁰¹² , R ²⁰¹³ , R ²⁰¹⁴ , R ²⁰¹⁵ and R ²⁰¹⁶ each independently represent a hydrogen atom or a substituent, and R ²⁰¹¹ and R ²⁰¹² , R ²⁰¹² and R ²⁰¹³ , R ²⁰¹³ and R ²⁰¹⁴ , R ²⁰¹⁴ and R ²⁰¹⁵ , R ²⁰¹⁵ and R ²⁰¹⁶ and R ²⁰¹⁶ R ²⁰¹¹ may be bonded to each other to form a ring.
In general formula (II-2), R ²⁰²¹ represents a hydrogen atom, an aliphatic group, an acyl group, a sulfonyl group, a sulfinyl group, an oxy radical group or a hydroxyl group, and Q forms a 5-membered, 6-membered or 7-membered ring. R ²⁰²² , R ²⁰²³ , R ²⁰²⁴ and R ²⁰²⁵ each independently represents a hydrogen atom, an aliphatic group, an aromatic group or a heterocyclic group bonded with a carbon atom, ²⁰²¹ and R ²⁰²² , R ²⁰²² and R ²⁰²³ , R ²⁰²⁴ and R ^2025, and R ²⁰²¹ and R ²⁰²⁴ may be bonded to each other to form a ring.
In general formula (II-3), R ²⁰³¹ , R ²⁰³² , R ²⁰³³ and R ²⁰³⁴ each independently represent a hydrogen atom or a substituent, and R ²⁰³⁵ is bonded by a hydrogen atom, an aliphatic group, an aromatic group or a carbon atom. R ²⁰³¹ and R ²⁰³² , R ²⁰³² and R ^2033, and R ²⁰³³ and R ²⁰³⁴ may be bonded to each other to form a ring.
In general formula (II-4), ^R2041 , ^R2042 , ^R2043 , ^R2044 , ^R2045 , ^R2046 , ^R2047 , ^R2048 , ^R2049 and ^R2050 each independently represents a hydrogen atom or a substituent, R ²⁰⁴¹ and R ^2042, R ²⁰⁴² and R ^2043, R ²⁰⁴³ and R ^2044, R ²⁰⁴⁴ and R ^2045, R ²⁰⁴⁶ and R ^2047, R ²⁰⁴⁷ and R ^2048, R ²⁰⁴⁸ and R ²⁰⁴⁹ and R ²⁰⁴⁹ and R ²⁰⁵⁰ are coupled to each other To form a ring.
In general formula (II-5), ^R2051 , ^R2052 , ^R2053 , ^R2054 , ^R2055 , ^R2056 , ^R2057 , ^R2058 , ^R2059 and ^R2060 each independently represents a hydrogen atom or a substituent, R ²⁰⁵¹ and R ²⁰⁵² , R ²⁰⁵² and R ²⁰⁵³ , R ²⁰⁵³ and R ²⁰⁵⁴ , R ²⁰⁵⁴ and R ²⁰⁵⁵ , R ²⁰⁵⁶ and R ²⁰⁵⁷ , R ²⁰⁵⁷ and R ²⁰⁵⁸ , R ²⁰⁵⁸ and R ^2059, and R ²⁰⁵⁹ and R ²⁰⁶⁰ are bonded to each other. To form a ring.
In the general formula (II-6), R ²⁰⁶¹ , R ²⁰⁶² , R ²⁰⁶³ , R ²⁰⁶⁴ , R ²⁰⁶⁵ , R ²⁰⁶⁶ , R ²⁰⁶⁷ , R ²⁰⁶⁸ , R ²⁰⁶⁹ and R ²⁰⁷⁰ each independently represents a hydrogen atom or a substituent, R ²⁰⁶¹ and R ²⁰⁶² , R ²⁰⁶² and R ²⁰⁶³ , R ²⁰⁶³ and R ²⁰⁶⁴ , R ²⁰⁶⁴ and R ²⁰⁶⁵ , R ²⁰⁶⁶ and R ²⁰⁶⁷ , R ²⁰⁶⁷ and R ²⁰⁶⁸ , R ²⁰⁶⁸ and R ^2069, and R ²⁰⁶⁹ and R ²⁰⁷⁰ are bonded to each other. To form a ring. X ²⁰⁶¹ represents a hydrogen atom, an aliphatic group, an aromatic group, or a heterocyclic group bonded with a carbon atom.
In general formula (II-7), R ²⁰⁷¹ , R ²⁰⁷² , R ²⁰⁷³ , R ²⁰⁷⁴ , R ²⁰⁷⁵ , R ²⁰⁷⁶ , R ²⁰⁷⁷ , R ²⁰⁷⁸ , R ²⁰⁷⁹ and R ²⁰⁸⁰ each independently represents a hydrogen atom or a substituent, R ²⁰⁷¹ and R ²⁰⁷² , R ²⁰⁷² and R ²⁰⁷³ , R ²⁰⁷³ and R ²⁰⁷⁴ , R ²⁰⁷⁴ and R ²⁰⁷⁵ , R ²⁰⁷⁶ and R ²⁰⁷⁷ , R ²⁰⁷⁷ and R ²⁰⁷⁸ , R ²⁰⁷⁸ and R ²⁰⁷⁹ and R ²⁰⁷⁹ and R ²⁰⁸⁰ are bonded to each other To form a ring.
In general formula (II-8), R ²⁰⁸¹ , R ²⁰⁸² , R ²⁰⁸³ , R ²⁰⁸⁴ , R ²⁰⁸⁵ and R ²⁰⁸⁶ each independently represent a hydrogen atom or a substituent. R ²⁰⁸¹ and R ²⁰⁸² , R ²⁰⁸² and R ²⁰⁸³ , R ²⁰⁸³ and R ²⁰⁸⁴ , R ²⁰⁸⁴ and R ^2085, and R ²⁰⁸⁵ and R ²⁰⁸⁶ may be bonded to each other to form a ring.
In general formula (II-9), R ²⁰⁹¹ , R ²⁰⁹² , R ²⁰⁹³ , R ²⁰⁹⁴ , R ²⁰⁹⁵ , R ²⁰⁹⁶ , R ²⁰⁹⁷ and R ²⁰⁹⁸ each independently represent a hydrogen atom or a substituent, and R ²⁰⁹⁹ and R ²¹⁰⁰ are Represents a substituent. R ²⁰⁹¹ and R ²⁰⁹² , R ²⁰⁹² and R ²⁰⁹³ , R ²⁰⁹³ and R ²⁰⁹⁴ , R ²⁰⁹⁵ and R ²⁰⁹⁶ , R ²⁰⁹⁶ and R ²⁰⁹⁷ and R ²⁰⁹⁷ and R ²⁰⁹⁸ may be bonded to each other to form a ring. n2099 and n2100 each independently represents an integer of 0 to 4, when the n2099 and n2100 are 2 or more, plural R ²⁰⁹⁹ and R ²¹⁰⁰ may be the same or different.
In the general formula (II-10), R ²¹⁰¹ , R ²¹⁰² , R ²¹⁰³ , R ²¹⁰⁴ , R ²¹⁰⁶ , R ²¹⁰⁷ , R ²¹⁰⁸ and R ²¹⁰⁹ each independently represent a hydrogen atom or a substituent, and R ²¹⁰⁵ represents a substituent. To express. R ²¹⁰¹ and R ²¹⁰² , R ²¹⁰² and R ²¹⁰³ , R ²¹⁰³ and R ²¹⁰⁴ , R ²¹⁰⁶ and R ²¹⁰⁷ , R ²¹⁰⁷ and R ^2108, and R ²¹⁰⁸ and R ²¹⁰⁹ may be bonded to each other to form a ring. n2105 represents an integer of 0 to 6, and when n2105 is 2 or more, a plurality of R ²¹⁰⁵ may be the same or different.
In general formula (II-11), R ²¹¹¹ , R ²¹¹² , R ²¹¹³ , R ²¹¹⁴ , R ²¹¹⁵ , R ²¹¹⁶ , R ²¹¹⁷ , R ²¹¹⁸ , R ²¹¹⁹ and R ²¹²⁰ each independently represent a hydrogen atom or a substituent. R ²¹¹¹ and R ²¹¹² , R ²¹¹² and R ²¹¹³ , R ²¹¹³ and R ²¹¹⁴ , R ²¹¹⁵ and R ²¹¹⁶ , R ²¹¹⁷ and R ²¹¹⁸ , R ²¹¹⁸ and R ²¹¹⁹ and R ²¹¹⁹ and R ²¹²⁰ are bonded together to form a ring. May be.
However, any one of R ^{2011 to} R ^{2016 in} the general formula (II-1), any one of R ^{2021 to} R ^{2025 in} the general formula (II-2), R ^{2031 in the} general formula (II-3) Any one of -R ²⁰³⁵ , any one of R ²⁰⁴¹ -R ^{2050 in} the general formula (II-4), any one of R ²⁰⁵¹ -R ^{2060 in} the general formula (II-5), Any one of R ^{2061 to} R ²⁰⁷⁰ of II-6), any one of R ^{2071 to} R ²⁰⁸⁰ of general formula (II-7), and any of R ^{2081 to} R ²⁰⁸⁶ of general formula (II-8) Any one of R ^{2091 to} R ²¹⁰⁰ of the general formula (II-9), any one of R ^{2101 to} R ²¹⁰⁹ of the general formula (II-10), and the general formula (II-11) Any one of R ^{2111 to} R ²¹²⁰ is substituted by a single bond for bonding one hydrogen atom contained therein to L ¹⁰ .

(3) The compound according to (1) or (2) above, wherein the compound represented by the general formula (I) has a 2,3-naphthalocyanine skeleton.

(4) The compound according to any one of (1) to (3) above, wherein the compound represented by the general formula (I) is a compound represented by the following general formula (III): .

In general formula (III), at least one of OR ^{311 to} OR ³¹⁸ independently represents a group having the same meaning as L ¹⁰ -R ¹⁰ in general formula (I), and R ^{311 to} R ³¹⁸ in the remaining OR ³¹¹ to OR ³¹⁸ . ³¹⁸ each independently represents an aliphatic group or an aromatic group. R ^{321 to} R ³³⁶ each independently represents a hydrogen atom or a substituent. M ³ represents a hydrogen atom, two atoms selected from the group consisting of monovalent metal atoms, a divalent metal atom, or a divalent substituted metal atom containing a trivalent or tetravalent metal atom.

  The phthalocyanine compound of the present invention has characteristics that it has absorption in the near infrared region, has good solubility, and is excellent in light resistance.

  Hereinafter, the phthalocyanine compound of the present invention will be described in detail. The description of the constituent elements described below may be made based on typical embodiments of the present invention, but the present invention is not limited to such embodiments. In the present specification, a numerical range represented by using “to” means a range including numerical values described before and after “to” as a lower limit value and an upper limit value.

  The compound represented by the general formula (I) of the present invention has a spectral absorption maximum wavelength (λmax) in the range of 750 nm to 1200 nm, and preferably has λmax in the range of 800 nm to 950 nm. . Here, λmax was measured at 25 ° C. using a spectroscopic absorption measurement device (manufactured by Hitachi High-Technologies Corporation, U-4100 spectrophotometer) after dissolving in THF solvent at a concentration of 0.4 to 4 μmol / L. Value.

  In the present specification, the substituent means an atom or a group of atoms other than a hydrogen atom. Examples of the substituent include an aliphatic group, an aromatic group, and a heterocyclic group, which will be described later, and examples of substituents on the alkyl portion of the substituted alkyl group, the substituted alkenyl group, the substituted alkynyl group, and the substituted aralkyl group, which will be described later. Are also included.

  In the present specification, the aliphatic group means an alkyl group, a substituted alkyl group, an alkenyl group, a substituted alkenyl group, an alkynyl group, a substituted alkynyl group, an aralkyl group, and a substituted aralkyl group. The alkyl group may have a branch or may form a ring. The alkyl group preferably has 1 to 20 carbon atoms, and more preferably 1 to 18 carbon atoms. The alkyl part of the substituted alkyl group is the same as the above alkyl group. The alkenyl group may have a branch or may form a ring. The alkenyl group preferably has 2 to 20 carbon atoms, and more preferably 2 to 18 carbon atoms. The alkenyl part of the substituted alkenyl group is the same as the above alkenyl group. The alkynyl group may have a branch or may form a ring. The number of carbon atoms in the alkynyl group is preferably 2-20, and more preferably 2-18. The alkynyl part of the substituted alkynyl group is the same as the above alkynyl group. The alkyl part of the aralkyl group and the substituted aralkyl group is the same as the above alkyl group. The aryl part of the aralkyl group and the substituted aralkyl group is the same as the following aryl group.

  Examples of substituents in the alkyl moiety of substituted alkyl groups, substituted alkenyl groups, substituted alkynyl groups and substituted aralkyl groups include halogen atoms (eg, chlorine atoms, bromine atoms, iodine atoms), alkyl groups [straight chain, branched, cyclic Represents a substituted or unsubstituted alkyl group. They are alkyl groups (preferably alkyl groups having 1 to 30 carbon atoms such as methyl group, ethyl group, n-propyl group, isopropyl group, tert-butyl group, n-octyl group, eicosyl group, 2-chloroethyl group, 2-cyanoethyl group, 2-ethylhexyl group), cycloalkyl group (preferably a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, such as cyclohexyl group, cyclopentyl group, 4-n-dodecylcyclohexyl group), Bicycloalkyl group (preferably a substituted or unsubstituted bicycloalkyl group having 5 to 30 carbon atoms, that is, a monovalent group obtained by removing one hydrogen atom from a bicycloalkane having 5 to 30 carbon atoms. For example, bicyclo [ 1.2.2] heptan-2-yl group, bicyclo [2.2.2] octane-3-yl group), and ring A tricyclo structure having many structures is also included. An alkyl group (for example, an alkyl group of an alkylthio group) in the substituents described below also represents such an alkyl group. ], An alkenyl group [represents a linear, branched or cyclic substituted or unsubstituted alkenyl group. They are an alkenyl group (preferably a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, such as a vinyl group, an allyl group, a prenyl group, a geranyl group, an oleyl group), a cycloalkenyl group (preferably a carbon number of 3 A substituted or unsubstituted cycloalkenyl group having ˜30, that is, a monovalent group obtained by removing one hydrogen atom of a cycloalkene having 3 to 30 carbon atoms, such as a 2-cyclopenten-1-yl group and 2-cyclohexene -1-yl group), a bicycloalkenyl group (substituted or unsubstituted bicycloalkenyl group, preferably a substituted or unsubstituted bicycloalkenyl group having 5 to 30 carbon atoms, that is, a hydrogen atom of a bicycloalkene having one double bond. For example, a bicyclo [2.2.1] hept-2-en-1-yl group, It is intended to include [2.2.2] oct-2-en-4-yl group). ], An alkynyl group (preferably a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, such as an ethynyl group, a propargyl group, or a trimethylsilylethynyl group), an aryl group (preferably a substituted or unsubstituted group having 6 to 30 carbon atoms) Aryl group such as phenyl group, p-tolyl group, naphthyl group, m-chlorophenyl group, o-hexadecanoylaminophenyl group), heterocyclic group (preferably 5- or 6-membered substituted or unsubstituted, aromatic Alternatively, it is a monovalent group obtained by removing one hydrogen atom from a non-aromatic heterocyclic compound, and more preferably a 5- to 6-membered aromatic heterocyclic group having 3 to 30 carbon atoms. -Furyl group, 2-thienyl group, 2-pyrimidinyl group, 2-benzothiazolyl group), cyano group, hydroxyl group, nitro group, carboxyl Group, alkoxy group (preferably a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms such as methoxy group, ethoxy group, isopropoxy group, tert-butoxy group, n-octyloxy group, 2-methoxyethoxy group) Group), an aryloxy group (preferably a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, such as phenoxy group, 2-methylphenoxy group, 4-tert-butylphenoxy group, 3-nitrophenoxy group, 2-tetradecanoylaminophenoxy group), silyloxy group (preferably a silyloxy group having 3 to 20 carbon atoms, such as trimethylsilyloxy group, tert-butyldimethylsilyloxy group), heterocyclic oxy group (preferably carbon number) 2-30 substituted or unsubstituted heterocyclic oxy groups, 1-phenyltetrazole-5 Oxy group, 2-tetrahydropyranyloxy group), acyloxy group (preferably formyloxy group, substituted or unsubstituted alkylcarbonyloxy group having 2 to 30 carbon atoms, substituted or unsubstituted arylcarbonyl group having 6 to 30 carbon atoms) Oxy groups such as formyloxy group, acetyloxy group, pivaloyloxy group, stearoyloxy group, benzoyloxy group, p-methoxyphenylcarbonyloxy group), carbamoyloxy group (preferably substituted or unsubstituted having 1 to 30 carbon atoms) Carbamoyloxy group, for example, N, N-dimethylcarbamoyloxy group, N, N-diethylcarbamoyloxy group, morpholinocarbonyloxy group, N, N-di-n-octylaminocarbonyloxy group, Nn-octylcarbamoyl Oxy group), al A alkoxycarbonyloxy group (preferably a substituted or unsubstituted alkoxycarbonyloxy group having 2 to 30 carbon atoms, such as a methoxycarbonyloxy group, an ethoxycarbonyloxy group, a tert-butoxycarbonyloxy group, or an n-octylcarbonyloxy group), Aryloxycarbonyloxy group (preferably a substituted or unsubstituted aryloxycarbonyloxy group having 7 to 30 carbon atoms such as phenoxycarbonyloxy group, p-methoxyphenoxycarbonyloxy group, pn-hexadecyloxyphenoxycarbonyl An oxy group), an amino group (preferably an amino group, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted anilino group having 6 to 30 carbon atoms, such as an amino group and a methylamino group. , Dimethylamino Group, anilino group, N-methyl-anilino group, diphenylamino group), acylamino group (preferably formylamino group, substituted or unsubstituted alkylcarbonylamino group having 1 to 30 carbon atoms, substitution having 6 to 30 carbon atoms) Or unsubstituted arylcarbonylamino group such as formylamino group, acetylamino group, pivaloylamino group, lauroylamino group, benzoylamino group, 3,4,5-tri-n-octyloxyphenylcarbonylamino group), aminocarbonyl An amino group (preferably a substituted or unsubstituted aminocarbonylamino group having 1 to 30 carbon atoms, such as carbamoylamino group, N, N-dimethylaminocarbonylamino group, N, N-diethylaminocarbonylamino group, morpholinocarbonylamino; Group), alkoxycal Nylamino group (preferably a substituted or unsubstituted alkoxycarbonylamino group having 2 to 30 carbon atoms such as methoxycarbonylamino group, ethoxycarbonylamino group, tert-butoxycarbonylamino group, n-octadecyloxycarbonylamino group, N-methyl Rumethoxycarbonylamino group), aryloxycarbonylamino group (preferably a substituted or unsubstituted aryloxycarbonylamino group having 7 to 30 carbon atoms, such as phenoxycarbonylamino group, p-chlorophenoxycarbonylamino group, m- n-octyloxyphenoxycarbonylamino group), sulfamoylamino group (preferably a substituted or unsubstituted sulfamoylamino group having 0 to 30 carbon atoms such as sulfamoylamino group, N, N-dimethylamino group) Sulfonylamino group, Nn-octylaminosulfonylamino group), alkyl and arylsulfonylamino groups (preferably substituted or unsubstituted alkylsulfonylamino group having 1 to 30 carbon atoms, substituted or unsubstituted groups having 6 to 30 carbon atoms) Arylsulfonylamino group of, for example, methylsulfonylamino group, butylsulfonylamino group, phenylsulfonylamino group, 2,3,5-trichlorophenylsulfonylamino group, p-methylphenylsulfonylamino group), mercapto group, alkylthio group ( Preferably, it is a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, such as a methylthio group, an ethylthio group, or an n-hexadecylthio group, an arylthio group (preferably a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms, such as The Nylthio group, p-chlorophenylthio group, m-methoxyphenylthio group), heterocyclic thio group (preferably a substituted or unsubstituted heterocyclic thio group having 2 to 30 carbon atoms, such as 2-benzothiazolylthio group, 1-phenyltetrazol-5-ylthio group), sulfamoyl group (preferably a substituted or unsubstituted sulfamoyl group having 0 to 30 carbon atoms such as N-ethylsulfamoyl group, N- (3-dodecyloxypropyl) sulfamoyl Group, N, N-dimethylsulfamoyl group, N-acetylsulfamoyl group, N-benzoylsulfamoyl group, N- (N′-phenylcarbamoyl) sulfamoyl group), sulfo group, alkyl and arylsulfinyl group ( Preferably, it is a substituted or unsubstituted alkylsulfinyl group having 1 to 30 carbon atoms, 6 to 30 substituted or unsubstituted arylsulfinyl groups such as methylsulfinyl group, ethylsulfinyl group, phenylsulfinyl, p-methylphenylsulfinyl group), alkyl and arylsulfonyl groups (preferably substituted or unsubstituted groups having 1 to 30 carbon atoms) A substituted alkylsulfonyl group, 6-30 substituted or unsubstituted arylsulfonyl groups such as methylsulfonyl group, ethylsulfonyl group, phenylsulfonyl group, p-methylphenylsulfonyl group), acyl group (preferably formyl group, carbon It is bonded to the carbonyl group by a substituted or unsubstituted alkylcarbonyl group having 2 to 30 carbon atoms, a substituted or unsubstituted arylcarbonyl group having 7 to 30 carbon atoms, or a substituted or unsubstituted carbon atom having 4 to 30 carbon atoms. A heterocyclic carbonyl group such as Til group, pivaloyl group, 2-chloroacetyl group, stearoyl group, benzoyl group, pn-octyloxyphenylcarbonyl group, 2-pyridylcarbonyl group, 2-furylcarbonyl group), aryloxycarbonyl group (preferably carbon A substituted or unsubstituted aryloxycarbonyl group of 7 to 30, for example, phenoxycarbonyl group, o-chlorophenoxycarbonyl group, m-nitrophenoxycarbonyl group, p-tert-butylphenoxycarbonyl group), alkoxycarbonyl group (preferably Is a substituted or unsubstituted alkoxycarbonyl group having 2 to 30 carbon atoms, such as a methoxycarbonyl group, an ethoxycarbonyl group, a tert-butoxycarbonyl group or an n-octadecyloxycarbonyl group), a carbamoyl group (preferably having a carbon number of 1 to 3 0 substituted or unsubstituted carbamoyl group such as carbamoyl group, N-methylcarbamoyl group, N, N-dimethylcarbamoyl group, N, N-di-n-octylcarbamoyl group, N- (methylsulfonyl) carbamoyl group) Aryl and heterocyclic azo groups (preferably substituted or unsubstituted arylazo groups having 6 to 30 carbon atoms, substituted or unsubstituted heterocyclic azo groups having 3 to 30 carbon atoms, such as phenylazo groups and p-chlorophenylazo groups) , 5-ethylthio-1,3,4-thiadiazol-2-ylazo group), imide group (preferably N-succinimide group, N-phthalimide group), phosphino group (preferably substituted with 2 to 30 carbon atoms or Unsubstituted phosphino groups such as dimethylphosphino group, diphenylphosphino group, methylphenol Xyphosphino group), phosphinyl group (preferably a substituted or unsubstituted phosphinyl group having 2 to 30 carbon atoms, such as phosphinyl group, dioctyloxyphosphinyl group, diethoxyphosphinyl group), phosphinyloxy group ( Preferably, it is a substituted or unsubstituted phosphinyloxy group having 2 to 30 carbon atoms, such as a diphenoxyphosphinyloxy group or a dioctyloxyphosphinyloxy group, or a phosphinylamino group (preferably having a carbon number). 2-30 substituted or unsubstituted phosphinylamino groups such as dimethoxyphosphinylamino group and dimethylaminophosphinylamino group, silyl groups (preferably substituted or unsubstituted 3 to 30 carbon atoms) Silyl groups such as trimethylsilyl group, tert-butyldimethylsilyl group, phenyldimethyl It represents a Rushiriru group).

  Among the above functional groups, those having a hydrogen atom may be substituted with the above groups by removing this. Examples of such functional groups include an alkylcarbonylaminosulfonyl group, an arylcarbonylaminosulfonyl group, an alkylsulfonylaminocarbonyl group, and an arylsulfonylaminocarbonyl group. Examples thereof include a methylsulfonylaminocarbonyl group, a p-methylphenylsulfonylaminocarbonyl group, an acetylaminosulfonyl group, and a benzoylaminosulfonyl group.

  Examples of the substituent of the aryl part of the substituted aralkyl group are the same as those described above as examples of the substituent of the alkyl part of the substituted alkyl group, substituted alkenyl group, substituted alkynyl group and substituted aralkyl group.

  In the present specification, the aromatic group means an aryl group and a substituted aryl group. In addition, these aromatic groups may be condensed with an aliphatic ring, another aromatic ring or a heterocyclic ring. 6-40 are preferable, as for the carbon atom number of an aromatic group, 6-30 are more preferable, and 6-20 are especially preferable. Among them, the aryl group is preferably a phenyl group or a naphthyl group, and particularly preferably a phenyl group.

  The aryl part of the substituted aryl group is the same as the above aryl group. Examples of the substituent of the substituted aryl group are the same as those described above as examples of the substituent of the alkyl portion of the substituted alkyl group, the substituted alkenyl group, the substituted alkynyl group, and the substituted aralkyl group.

  In the present specification, a heterocyclic group means a saturated or unsaturated ring group containing a hetero atom. The heterocyclic group preferably contains a 5- or 6-membered saturated or unsaturated heterocyclic ring. As used herein, the heterocyclic ring may be an aliphatic ring, an aromatic ring or a condensed condensed heterocyclic ring. Examples of heteroatoms of the heterocycle include B, N, O, S, Se and Te. Heteroatoms are preferably N, O and S. The heterocyclic ring preferably has a valence (monovalence) in which the carbon atom is free (the heterocyclic group is bonded at the carbon atom). The number of carbon atoms of a preferable heterocyclic group is 1-40, More preferably, it is 1-30, More preferably, it is 1-20. Examples of the saturated heterocyclic ring include a pyrrolidine ring, a morpholine ring, a 2-bora-1,3-dioxolane ring, and a 1,3-thiazolidine ring. Examples of the unsaturated heterocyclic ring include imidazole ring, thiazole ring, benzothiazole ring, benzoxazole ring, benzotriazole ring, benzoselenazole ring, pyridine ring, pyrimidine ring and quinoline ring. The heterocyclic group may have a substituent. Examples of the substituent are the same as those described above as examples of the substituent of the alkyl portion of the substituted alkyl group, the substituted alkenyl group, the substituted alkynyl group, and the substituted aralkyl group.

  Next, the compounds represented by the general formulas (I) to (III) will be described. In addition, the compound represented by general formula (III) is a preferable compound of the compound represented by general formula (I).

The substituent R ¹⁰ of the general formula (I) has a spectral absorption maximum wavelength in 270 to 750 nm in a solution of the compound R ¹⁰ —H of 470 nm or less, or the compound R ¹⁰ —H is a singlet oxygen scavenger, An atomic group that satisfies the condition of being a radical trapping agent or an antioxidant. Here, the spectral absorption maximum wavelength in 270~750nm in a solution of the compound R ¹⁰ -H can be measured by the same measuring method as the spectral absorption maximum wavelength of the compound (I). The spectral absorption maximum wavelength in 270 to 750 nm in the solution of compound R ¹⁰ —H is preferably 410 nm or less, and more preferably 380 nm or less. If the spectral absorption maximum wavelength in 270 to 750 nm in the solution of compound R ¹⁰ -H is 470 nm or less, compound R ¹⁰ -H does not fall under any of the singlet oxygen scavenger, radical trap agent, or antioxidant. It does not matter.

The compound R ¹⁰ —H may be any compound as long as it captures singlet oxygen, traps radicals, or prevents oxidation. Compound R ¹⁰ —H may correspond to a plurality of singlet oxygen scavengers, radical trap agents, and antioxidants.

As R ¹⁰ in the general formula (I), those represented by the general formulas (II-1) to (II-11) are particularly preferable. Here, the general formulas (II-1) to (II-11) will be described in detail.

In the general formula (II-1), the hydrolyzable protecting group as R ²⁰¹¹ is a silyl group, a phosphate group or a group represented by the following general formula (IV).
R ¹¹¹ -Y ¹¹¹ -Z ¹¹¹ -
Formula (IV)
In the formula, R ¹¹¹ represents an aliphatic group, an aromatic group or a heterocyclic group bonded with a carbon atom, and Y ¹¹¹ represents a single bond, —O—, —S—, —N (R ¹¹² ) —, —C—. And a combination of these. Here, R ¹¹² represents a hydrogen atom, an aliphatic group, an aromatic group or a heterocyclic group, an acyl group or a sulfonyl group bonded with a carbon atom. Z ¹¹¹ represents —CO— or —SO ₂ —. R ²⁰¹¹ is preferably a hydrogen atom, an aliphatic group having 1 to 20 carbon atoms, an aromatic group having 6 to 20 carbon atoms, a heterocyclic group bonded with carbon atoms having 2 to 20 carbon atoms, and water having 1 to 20 carbon atoms. A decomposable protecting group, more preferably a hydrogen atom, an aliphatic group having 1 to 10 carbon atoms, or a hydrolyzable protecting group having 1 to 10 carbon atoms, more preferably a hydrogen atom or 1 to 8 carbon atoms. A hydrolyzable protecting group connected by an aliphatic group, a silyl group having 1 to 10 carbon atoms, a phosphate ester group having 1 to 10 carbon atoms, or a carbonyl group having 1 to 10 carbon atoms, and more preferably a hydrogen atom , A hydrolyzable protecting group linked by an aliphatic group having 1 to 4 carbon atoms, a silyl group having 3 to 6 carbon atoms, a phosphate ester group having 2 to 8 carbon atoms, or a carbonyl group having 1 to 8 carbon atoms. More preferably, a hydrogen atom, trimethylsilyl group, di Chill or diethyl phosphoric acid ester group, a benzoyl or acetyl group, most preferably a hydrogen atom.

R ²⁰¹² , R ²⁰¹³ , R ²⁰¹⁴ , R ²⁰¹⁵ and R ²⁰¹⁶ are preferably hydrogen atom, halogen atom, alkyl group, alkenyl group, alkynyl group, aryl group, cyano group, hydroxyl group, carboxyl group, alkoxy group, aryloxy group Silyloxy group, acyloxy group, carbamoyloxy group, alkoxycarbonyloxy group, aryloxycarbonyloxy group, amino group, acylamino group, aminocarbonylamino group, alkoxycarbonylamino group, aryloxycarbonylamino group, sulfamoylamino group, Alkyl and arylsulfonylamino groups, mercapto groups, alkylthio groups, arylthio groups, sulfamoyl groups, sulfo groups, alkyl and arylsulfinyl groups, alkyl and arylsulfonyl groups, acyl groups, A reeloxycarbonyl group, an alkoxycarbonyl group, a carbamoyl group, an imide group, a phosphino group, a phosphinyl group, a phosphinyloxy group, a phosphinylamino group, and a silyl group, more preferably a hydrogen atom, a halogen atom, an alkyl group, Alkenyl, aryl, cyano, hydroxyl, carboxyl, alkoxy, aryloxy, silyloxy, acyloxy, carbamoyloxy, alkoxycarbonyloxy, aryloxycarbonyloxy, amino, acylamino, alkylthio Group, arylthio group, acyl group, aryloxycarbonyl group, alkoxycarbonyl group, carbamoyl group and silyl group, more preferably hydrogen atom, halogen atom, alkyl group, aryl group, hydroxy group Group, alkoxy group, acyloxy group, acylamino group, carbamoyloxy group, alkylthio group, more preferably hydrogen atom, halogen atom, alkyl group, hydroxyl group, alkoxy group, acylamino group, most preferably hydrogen atom or alkyl group. It is a group. Moreover, it is preferable that one or both of R ²⁰¹² and R ²⁰¹⁶ is a tertiary alkyl group.

In Formula (II-2), R ²⁰²¹ is preferably a hydrogen atom, an aliphatic group having 1 to 10 carbon atoms, an acyl group having 2 to 10 carbon atoms, an oxy radical, or a hydroxyl group, more preferably a hydrogen atom or carbon number. An alkyl group having 1 to 3 carbon atoms, an acyl group having 2 to 7 carbon atoms, an oxy radical or a hydroxyl group, more preferably a hydrogen atom, an acetyl group, an oxy radical or a hydroxyl group, and most preferably a hydrogen atom. R ²⁰²² , R ²⁰²³ , R ²⁰²⁴ and R ²⁰²⁵ are preferably a hydrogen atom or an aliphatic group having 1 to 10 carbon atoms, more preferably a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, more preferably hydrogen. It is an atom or an alkyl group having 1 to 2 carbon atoms, and most preferably, all of R ^{2022 to} R ²⁰²⁵ are methyl groups. Q is preferably a nonmetallic atom group necessary for forming a 5- to 7-membered ring composed of a carbon atom, a hydrogen atom, an oxygen atom, a sulfur atom and a nitrogen atom, more preferably a carbon atom, a hydrogen atom, Non-metallic atom group necessary for forming a 5- to 7-membered ring composed of an oxygen atom and a nitrogen atom, more preferably a 5- to 7-membered ring composed of a carbon atom, a hydrogen atom and a nitrogen atom It is a nonmetallic atom group necessary for forming a ring, and most preferably a nonmetallic atom group necessary for forming a piperidine ring.

In the general formula (II-3), R ²⁰³¹ , R ²⁰³² , R ²⁰³³ and R ²⁰³⁴ each independently represent a hydrogen atom or a substituent, and examples of the substituent include the aforementioned substituted alkyl group, substituted alkenyl group and substituted alkynyl group. And the thing similar to what was mentioned as an example of the substituent of the alkyl part of a substituted aralkyl group is mentioned. R ²⁰³¹ , R ²⁰³² , R ²⁰³³ and R ²⁰³⁴ are preferably hydrogen atom, halogen atom, alkyl group, alkenyl group, alkynyl group, aryl group, cyano group, hydroxyl group, carboxyl group, alkoxy group, aryloxy group, silyloxy group , Acyloxy group, carbamoyloxy group, alkoxycarbonyloxy group, aryloxycarbonyloxy group, amino group, acylamino group, aminocarbonylamino group, alkoxycarbonylamino group, aryloxycarbonylamino group, sulfamoylamino group, alkyl and aryl Sulfonylamino group, mercapto group, alkylthio group, arylthio group, sulfamoyl group, sulfo group, alkyl and arylsulfinyl group, alkyl and arylsulfonyl group, acyl group, aryl group Xoxycarbonyl group, alkoxycarbonyl group, carbamoyl group, imide group, phosphino group, phosphinyl group, phosphinyloxy group, phosphinylamino group, silyl group, more preferably hydrogen atom, halogen atom, alkyl group, alkenyl Group, aryl group, cyano group, hydroxyl group, carboxyl group, alkoxy group, aryloxy group, silyloxy group, amino group, alkylthio group, arylthio group, imide group, silyl group, more preferably hydrogen atom, halogen atom, An alkyl group, an aryl group, an alkoxy group, an aryloxy group, a silyloxy group, and an amino group, more preferably a hydrogen atom, a halogen atom, and an alkyl group, and most preferably a hydrogen atom and a halogen atom.

R ²⁰³⁵ represents a hydrogen atom, an aliphatic group, an aromatic group or a heterocyclic group bonded with a carbon atom, preferably a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, or an aryl group, more preferably a hydrogen atom, An alkyl group having 1 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, an alkynyl group having 2 to 30 carbon atoms, and an aryl group having 6 to 30 carbon atoms, more preferably a hydrogen atom or an alkyl group having 1 to 25 carbon atoms. An alkyl group, an alkenyl group having 2 to 25 carbon atoms, and an aryl group having 6 to 25 carbon atoms, more preferably an alkyl group having 1 to 22 carbon atoms and an aryl group having 6 to 22 carbon atoms, more preferably carbon. An aryl group having 6 to 20 carbon atoms, and most preferably an orthohydroxyphenyl group having 6 to 20 carbon atoms.

In the general formula (II-4), R ²⁰⁴¹ , R ²⁰⁴² , R ²⁰⁴³ , R ²⁰⁴⁴ , R ²⁰⁴⁵ , R ²⁰⁴⁶ , R ²⁰⁴⁷ , R ²⁰⁴⁸ , R ²⁰⁴⁹ and R ²⁰⁵⁰ represent a hydrogen atom or a substituent, and examples of substituents Examples thereof include the same as those mentioned as the examples of the substituent of the alkyl moiety of the substituted alkyl group, substituted alkenyl group, substituted alkynyl group and substituted aralkyl group described above. Preferred R ²⁰⁴¹ , R ²⁰⁴² , R ²⁰⁴³ , R ²⁰⁴⁴ , R ²⁰⁴⁵ , R ²⁰⁴⁶ , R ²⁰⁴⁷ , R ²⁰⁴⁸ , R ²⁰⁴⁹ and R ²⁰⁵⁰ are a hydrogen atom, halogen atom, alkyl group, alkenyl group, alkynyl group, aryl group, cyano group Group, hydroxyl group, carboxyl group, alkoxy group, aryloxy group, silyloxy group, acyloxy group, carbamoyloxy group, alkoxycarbonyloxy group, aryloxycarbonyloxy group, amino group, acylamino group, aminocarbonylamino group, alkoxycarbonylamino Group, aryloxycarbonylamino group, sulfamoylamino group, alkyl and arylsulfonylamino group, mercapto group, alkylthio group, arylthio group, sulfamoyl group, sulfo group, alkyl and arylsulfinyl group, alkyl and Arylsulfonyl group, acyl group, aryloxycarbonyl group, alkoxycarbonyl group, carbamoyl group, imide group, phosphino group, phosphinyl group, phosphinyloxy group, phosphinylamino group, silyl group, more preferably a hydrogen atom , Halogen atom, alkyl group, alkenyl group, aryl group, cyano group, hydroxyl group, carboxyl group, alkoxy group, aryloxy group, silyloxy group, acyloxy group, acylamino group, aminocarbonylamino group, alkoxycarbonylamino group, aryloxy Carbonylamino group, sulfamoylamino group, alkyl and arylsulfonylamino group, mercapto group, alkylthio group, arylthio group, sulfamoyl group, sulfo group, alkyl and arylsulfonyl group, Sil group, aryloxycarbonyl group, alkoxycarbonyl group, carbamoyl group, imide group, silyl group, more preferably hydrogen atom, halogen atom, alkyl group, aryl group, hydroxyl group, alkoxy group, aryloxy group, acyloxy group , Acylamino group, alkyl and arylsulfonylamino group, sulfamoyl group, acyl group, aryloxycarbonyl group, alkoxycarbonyl group, carbamoyl group, more preferably hydrogen atom, halogen atom, alkyl group, hydroxyl group, alkoxy group, acyloxy Group, acylamino group, acyl group, alkoxycarbonyl group, carbamoyl group, more preferably hydrogen atom, halogen atom, alkyl group, hydroxyl group, alkoxy group, acylamino group, alcohol Shi is a carbonyl group. R ²⁰⁴¹ is most preferably a hydroxy group.

In the general formula (II-5), R ²⁰⁵¹ , R ²⁰⁵² , R ²⁰⁵³ , R ²⁰⁵⁴ , R ²⁰⁵⁵ , R ²⁰⁵⁶ , R ²⁰⁵⁷ , R ²⁰⁵⁸ , R ²⁰⁵⁹ and R ²⁰⁶⁰ represent a hydrogen atom or a substituent, and examples of the substituent Examples thereof include the same as those mentioned as the examples of the substituent of the alkyl moiety of the substituted alkyl group, substituted alkenyl group, substituted alkynyl group and substituted aralkyl group described above. Preferred R ²⁰⁵¹ , R ²⁰⁵² , R ²⁰⁵³ , R ²⁰⁵⁴ , R ²⁰⁵⁵ , R ²⁰⁵⁶ , R ²⁰⁵⁷ , R ²⁰⁵⁸ , R ²⁰⁵⁹ and R ²⁰⁶⁰ are a hydrogen atom, halogen atom, alkyl group, alkenyl group, alkynyl group, aryl group, cyano group Group, hydroxyl group, carboxyl group, alkoxy group, aryloxy group, silyloxy group, acyloxy group, carbamoyloxy group, alkoxycarbonyloxy group, aryloxycarbonyloxy group, amino group, acylamino group, aminocarbonylamino group, alkoxycarbonylamino Group, aryloxycarbonylamino group, sulfamoylamino group, alkyl and arylsulfonylamino group, mercapto group, alkylthio group, arylthio group, sulfamoyl group, sulfo group, alkyl and arylsulfinyl group, alkyl and Arylsulfonyl group, acyl group, aryloxycarbonyl group, alkoxycarbonyl group, carbamoyl group, imide group, phosphino group, phosphinyl group, phosphinyloxy group, phosphinylamino group, silyl group, more preferably a hydrogen atom , Halogen atom, alkyl group, alkenyl group, aryl group, cyano group, hydroxyl group, carboxyl group, alkoxy group, aryloxy group, silyloxy group, acyloxy group, acylamino group, aminocarbonylamino group, alkoxycarbonylamino group, aryloxy Carbonylamino group, sulfamoylamino group, alkyl and arylsulfonylamino group, mercapto group, alkylthio group, arylthio group, sulfamoyl group, sulfo group, alkyl and arylsulfonyl group, Sil group, aryloxycarbonyl group, alkoxycarbonyl group, carbamoyl group, imide group, silyl group, more preferably hydrogen atom, halogen atom, alkyl group, aryl group, hydroxyl group, alkoxy group, aryloxy group, acyloxy group , Acylamino group, alkyl and arylsulfonylamino group, sulfamoyl group, acyl group, aryloxycarbonyl group, alkoxycarbonyl group, carbamoyl group, more preferably hydrogen atom, halogen atom, alkyl group, hydroxyl group, alkoxy group, acyloxy Group, acylamino group, acyl group, alkoxycarbonyl group, carbamoyl group, more preferably hydrogen atom, halogen atom, alkyl group, hydroxyl group, alkoxy group, acylamino group, alcohol Shi is a carbonyl group. R ²⁰⁵¹ is most preferably a hydroxy group.

In the general formula (II-6), R ²⁰⁶¹ , R ²⁰⁶² , R ²⁰⁶³ , R ²⁰⁶⁴ , R ²⁰⁶⁵ , R ²⁰⁶⁶ , R ²⁰⁶⁷ , R ²⁰⁶⁸ , R ²⁰⁶⁹ and R ²⁰⁷⁰ represent a hydrogen atom or a substituent, and examples of the substituent Examples thereof include the same as those mentioned as the examples of the substituent of the alkyl moiety of the substituted alkyl group, substituted alkenyl group, substituted alkynyl group and substituted aralkyl group described above. Preferred R ²⁰⁶¹ , R ²⁰⁶² , R ²⁰⁶³ , R ²⁰⁶⁴ , R ²⁰⁶⁵ , R ²⁰⁶⁶ , R ²⁰⁶⁷ , R ²⁰⁶⁸ , R ²⁰⁶⁹ and R ²⁰⁷⁰ are a hydrogen atom, halogen atom, alkyl group, alkenyl group, alkynyl group, aryl group, cyano group Group, hydroxyl group, carboxyl group, alkoxy group, aryloxy group, silyloxy group, acyloxy group, carbamoyloxy group, alkoxycarbonyloxy group, aryloxycarbonyloxy group, amino group, acylamino group, aminocarbonylamino group, alkoxycarbonylamino Group, aryloxycarbonylamino group, sulfamoylamino group, alkyl and arylsulfonylamino group, mercapto group, alkylthio group, arylthio group, sulfamoyl group, sulfo group, alkyl and arylsulfinyl group, alkyl and Arylsulfonyl group, acyl group, aryloxycarbonyl group, alkoxycarbonyl group, carbamoyl group, imide group, phosphino group, phosphinyl group, phosphinyloxy group, phosphinylamino group, silyl group, more preferably a hydrogen atom , Halogen atom, alkyl group, aryl group, hydroxyl group, alkoxy group, aryloxy group, silyloxy group, acyloxy group, carbamoyloxy group, alkoxycarbonyloxy group, aryloxycarbonyloxy group, amino group, acylamino group, aminocarbonylamino Group, alkoxycarbonylamino group, aryloxycarbonylamino group, sulfamoylamino group, alkyl and arylsulfonylamino group, alkylthio group, arylthio group, sulfamoyl group, acyl Group, aryloxycarbonyl group, alkoxycarbonyl group, carbamoyl group, silyl group, more preferably hydrogen atom, halogen atom, alkyl group, aryl group, alkoxy group, aryloxy group, amino group, acylamino group, alkylthio group, An arylthio group, more preferably a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an amino group, and an acylamino group, and most preferably a hydrogen atom, an alkoxy group, and an amino group.

X ²⁰⁶¹ represents a hydrogen atom, an aliphatic group, an aromatic group or a heterocyclic group bonded with a carbon atom, preferably a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group or an aryl group, more preferably a hydrogen atom, An alkyl group having 1 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, an alkynyl group having 2 to 30 carbon atoms, and an aryl group having 6 to 30 carbon atoms, more preferably a hydrogen atom or an alkyl group having 1 to 25 carbon atoms. An alkyl group, an alkenyl group having 2 to 25 carbon atoms, and an aryl group having 6 to 25 carbon atoms, more preferably an alkyl group having 1 to 22 carbon atoms and an aryl group having 6 to 22 carbon atoms, most preferably carbon. It is a C1-C18 alkyl group.

In the general formula (II-7), R ²⁰⁷¹ , R ²⁰⁷² , R ²⁰⁷³ , R ²⁰⁷⁴ , R ²⁰⁷⁵ , R ²⁰⁷⁶ , R ²⁰⁷⁷ , R ²⁰⁷⁸ , R ²⁰⁷⁹ and R ²⁰⁸⁰ represent a hydrogen atom or a substituent, and examples of the substituent Examples thereof include the same as those mentioned as the examples of the substituent of the alkyl moiety of the substituted alkyl group, substituted alkenyl group, substituted alkynyl group and substituted aralkyl group described above. Preferred R ²⁰⁷¹ , R ²⁰⁷² , R ²⁰⁷³ , R ²⁰⁷⁴ , R ²⁰⁷⁵ , R ²⁰⁷⁶ , R ²⁰⁷⁷ , R ²⁰⁷⁸ , R ²⁰⁷⁹ and R ²⁰⁸⁰ are a hydrogen atom, halogen atom, alkyl group, alkenyl group, alkynyl group, aryl group, cyano group Group, hydroxyl group, carboxyl group, alkoxy group, aryloxy group, silyloxy group, acyloxy group, carbamoyloxy group, alkoxycarbonyloxy group, aryloxycarbonyloxy group, amino group, acylamino group, aminocarbonylamino group, alkoxycarbonylamino Group, aryloxycarbonylamino group, sulfamoylamino group, alkyl and arylsulfonylamino group, mercapto group, alkylthio group, arylthio group, sulfamoyl group, sulfo group, alkyl and arylsulfinyl group, alkyl and Arylsulfonyl group, acyl group, aryloxycarbonyl group, alkoxycarbonyl group, carbamoyl group, imide group, phosphino group, phosphinyl group, phosphinyloxy group, phosphinylamino group, silyl group, more preferably a hydrogen atom Halogen atom, alkyl group, aryl group, cyano group, hydroxyl group, alkoxy group, aryloxy group, acyloxy group, amino group, acylamino group, mercapto group, alkylthio group, arylthio group, sulfamoyl group, alkyl and arylsulfinyl group, Alkyl and arylsulfonyl groups, acyl groups, aryloxycarbonyl groups, alkoxycarbonyl groups, silyl groups, more preferably hydrogen atoms, halogen atoms, alkyl groups, aryl groups, hydroxyl groups, alcohols, Shi group, an acyloxy group, an amino group, an acylamino group, an arylthio group, an acyl group, an aryloxycarbonyl group, an alkoxycarbonyl group, R ²⁰⁷¹ is most preferably a hydroxy group.

In the general formula (II-8), R ²⁰⁸¹ , R ²⁰⁸² , R ²⁰⁸³ , R ²⁰⁸⁴ , R ²⁰⁸⁵ and R ²⁰⁸⁶ represent a hydrogen atom or a substituent. Examples of the substituent include the above-mentioned substituted alkyl group, substituted alkenyl group, The thing similar to what was mentioned as an example of the substituent of the alkyl part of a substituted alkynyl group and a substituted aralkyl group is mentioned. R ²⁰⁸¹ is preferably a hydrogen atom, halogen atom, alkyl group, alkenyl group, alkynyl group, aryl group, heterocyclic group, cyano group, hydroxyl group, nitro group, carboxyl group, alkoxy group, aryloxy group, silyloxy group, Heterocyclic oxy group, acyloxy group, carbamoyloxy group, alkoxycarbonyloxy group, aryloxycarbonyloxy group, amino group, acylamino group, aminocarbonylamino group, alkoxycarbonylamino group, aryloxycarbonylamino group, sulfamoylamino group Alkyl, arylsulfonylamino group, mercapto group, alkylthio group, arylthio group, heterocyclic thio group, sulfamoyl group, sulfo group, alkyl and arylsulfinyl group, alkyl and arylsulfur group Nyl group, acyl group, aryloxycarbonyl group, alkoxycarbonyl group, carbamoyl group, imide group, phosphino group, phosphinyl group, phosphinyloxy group, phosphinylamino group, silyl group, more preferably a hydrogen atom, Halogen atom, alkyl group, aryl group, heterocyclic group, cyano group, hydroxyl group, alkoxy group, aryloxy group, silyloxy group, heterocyclic oxy group, alkoxycarbonyl group, acyloxy group, carbamoyloxy group, alkoxycarbonyloxy group, Aryloxycarbonyloxy, amino, acylamino, aminocarbonylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfamoylamino, alkyl and arylsulfonylamino, acyl Group, aryloxycarbonyl group, alkoxycarbonyl group, carbamoyl group, imide group, more preferably hydrogen atom, alkyl group, aryl group, heterocyclic group, amino group, acylamino group, aminocarbonylamino group, alkoxycarbonyl group , Alkoxycarbonylamino group, aryloxycarbonylamino group, sulfamoylamino group, alkyl and arylsulfonylamino group, more preferably alkyl group, aryl group, heterocyclic group, alkoxycarbonyl group and acylamino group. R ²⁰⁸² , R ²⁰⁸³ , R ²⁰⁸⁴ and R ²⁰⁸⁶ are preferably hydrogen atom, halogen atom, alkyl group, alkenyl group, alkynyl group, aryl group, heterocyclic group, cyano group, hydroxyl group, carboxyl group, alkoxy group, aryloxy Group, silyloxy group, heterocyclic oxy group, acyloxy group, carbamoyloxy group, alkoxycarbonyloxy group, aryloxycarbonyloxy group, amino group, acylamino group, aminocarbonylamino group, alkoxycarbonylamino group, aryloxycarbonylamino group, Sulfamoylamino group, alkyl and arylsulfonylamino group, mercapto group, alkylthio group, arylthio group, heterocyclic thio group, sulfamoyl group, sulfo group, alkyl and arylsulfinyl group, alkyl group And arylsulfonyl group, acyl group, aryloxycarbonyl group, alkoxycarbonyl group, carbamoyl group, imide group, phosphino group, phosphinyl group, phosphinyloxy group, phosphinylamino group, silyl group, more preferably hydrogen An atom, a halogen atom, an alkyl group, an aryl group, a heterocyclic group, a cyano group, a hydroxyl group, an alkoxy group, an aryloxy group, and a silyl group, more preferably a hydrogen atom, a halogen atom, and an alkyl group, most preferably It is a hydrogen atom. R ²⁰⁸⁵ is preferably a hydrogen atom, halogen atom, alkyl group, alkenyl group, alkynyl group, aryl group, heterocyclic group, cyano group, hydroxyl group, nitro group, carboxyl group, alkoxy group, aryloxy group, silyloxy group, Heterocyclic oxy group, acyloxy group, carbamoyloxy group, alkoxycarbonyloxy group, aryloxycarbonyloxy group, amino group, acylamino group, aminocarbonylamino group, alkoxycarbonylamino group, aryloxycarbonylamino group, sulfamoylamino group Alkyl, arylsulfonylamino group, mercapto group, alkylthio group, arylthio group, heterocyclic thio group, sulfamoyl group, sulfo group, alkyl and arylsulfinyl group, alkyl and arylsulfur group Nyl group, acyl group, aryloxycarbonyl group, alkoxycarbonyl group, carbamoyl group, imide group, phosphino group, phosphinyl group, phosphinyloxy group, phosphinylamino group, silyl group, more preferably a hydrogen atom, Halogen atom, alkyl group, aryl group, heterocyclic group, cyano group, hydroxyl group, alkoxy group, aryloxy group, silyloxy group, heterocyclic oxy group, acyloxy group, carbamoyloxy group, alkoxycarbonyloxy group, aryloxycarbonyloxy Group, amino group, acylamino group, aminocarbonylamino group, alkoxycarbonylamino group, aryloxycarbonylamino group, sulfamoylamino group, alkyl and arylsulfonylamino group, alkylthio group, arylthio Group, heterocyclic thio group, sulfamoyl group, aacyl group, aryloxycarbonyl group, alkoxycarbonyl group, carbamoyl group, imide group, silyl group, more preferably hydrogen atom, alkyl group, aryl group, heterocyclic group, amino group Group, acylamino group, aminocarbonylamino group, alkoxycarbonylamino group, aryloxycarbonylamino group, sulfamoylamino group, alkyl and arylsulfonylamino group, more preferably heterocyclic group, amino group, and acylamino group. .

In general formula (II-9), R ²⁰⁹¹ , R ²⁰⁹⁴ , R ²⁰⁹⁵ and R ²⁰⁹⁸ are preferably a hydrogen atom, a halogen atom, an alkyl group, an aryl group, a cyano group, a hydroxyl group, an alkoxy group, an amino group or a mercapto group. More preferably a hydrogen atom, a halogen atom, an alkyl group, a hydroxyl group, an alkoxy group or an amino group, and most preferably a hydrogen atom. R ²⁰⁹² , R ²⁰⁹³ , R ²⁰⁹⁶ and R ²⁰⁹⁷ are preferably a hydrogen atom, a halogen atom, an alkyl group, an aryl group, a heterocyclic group, a cyano group, a hydroxyl group, a ditro group, a carboxyl group, an alkoxy group, an aryloxy group, Silyloxy group, acyloxy group, carbamoyloxy group, alkoxycarbonyloxy group, aryloxycarbonyloxy group, amino group, acylamino group, aminocarbonylamino group, alkoxycarbonylamino group, aryloxycarbonylamino group, sulfamoylamino group, alkyl And arylsulfonylamino group, mercapto group, alkylthio group, arylthio group, sulfamoyl group, alkyl and arylsulfinyl group, alkyl and arylsulfonyl group, acyl group, aryloxycarbonyl group , Alkoxycarbonyl group, carbamoyl group, imide group, silyl group, more preferably hydrogen atom, halogen atom, alkyl group, aryl group, hydroxyl group, alkoxy group, aryloxy group, acyloxy group, amino group, acylamino group, A mercapto group, an alkylthio group, and a sulfamoyl group, more preferably a hydrogen atom, an alkyl group, an aryl group, an alkoxy group, an amino group, a mercapto group, and an alkylthio group, and more preferably a hydrogen atom, an alkyl group, an aryl group, and an alkoxy group. It is a group. R ²⁰⁹⁹ and R ²¹⁰⁰ are preferably halogen atoms, alkyl groups, aryl groups, cyano groups, hydroxyl groups, alkoxy groups, aryloxy groups, silyloxy groups, amino groups, acylamino groups, mercapto groups, alkylthio groups, arylthio groups, heterocyclic rings A thio group and a silyl group, more preferably a halogen atom, an alkyl group, an aryl group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group and a heterocyclic thio group, and more preferably a halogen atom, an alkyl group and an aryl group. Group, an alkoxy group. n2099 and n2100 are preferably 0 to 3, more preferably 0 to 2, still more preferably 0 or 1, and 0 is most preferable.

In the general formula (II-10), preferred ranges of R ²¹⁰¹ , R ²¹⁰⁴ , R ²¹⁰⁶ and R ²¹⁰⁹ are the same as those of R ²⁰⁹¹ described above. The preferred ranges of R ²¹⁰² , R ²¹⁰³ , R ²¹⁰⁷ and R ²¹⁰⁸ are the same as those of R ²⁰⁹² described above. R ²¹⁰⁵ is preferably a halogen atom, alkyl group, aryl group, heterocyclic group, cyano group, hydroxyl group, alkoxy group, aryloxy group, heterocyclic oxy group, silyloxy group, amino group, acylamino group, mercapto group, alkylthio group , An arylthio group, a heterocyclic thio group, and a silyl group, more preferably a halogen atom, an alkyl group, an aryl group, an alkoxy group, an aryloxy group, an amino group, an alkylthio group, and an arylthio group, more preferably a halogen atom, An alkyl group, an alkoxy group, an amino group, and an alkylthio group are preferable, and a halogen atom and an alkyl group are more preferable. n2105 is preferably 0 to 4, more preferably 0 to 2, still more preferably 0 to 1, and most preferably 0.

In the general formula (II-11), preferred ranges of R ²¹¹¹ , R ²¹¹⁴ , R ²¹¹⁷ and R ²¹²⁰ are the same as those of R ²⁰⁹¹ described above. The preferred ranges of R ²¹¹² , R ²¹¹³ , R ²¹¹⁸ and R ²¹¹⁹ are the same as those of R ²⁰⁹² described above. R ²¹¹⁵ and R ²¹¹⁶ are preferably a hydrogen atom, halogen atom, alkyl group, aryl group, heterocyclic group, cyano group, nitro group, hydroxyl group, alkoxy group, aryloxy group, heterocyclic oxy group, silyloxy group, amino group , Acylamino group, mercapto group, alkylthio group, arylthio group, heterocyclic thio group, silyl group, more preferably hydrogen atom, halogen atom, alkyl group, aryl group, heterocyclic group, cyano group, nitro group, alkoxy group , Aryloxy group, silyloxy group, amino group, acylamino group, alkylthio group, and arylthio group, more preferably a hydrogen atom, a halogen atom, an alkyl group, a cyano group, an alkoxy group, and an amino group, more preferably a hydrogen atom. , An alkyl group.

  The methods for synthesizing the groups represented by the general formulas (II-1) and (II-2) are described in British Patents 1,326,889, 1,354,313, 1,410,846, US Pat. 336, 135, 4, 268, 593, 4, 558, 131, 4, 584, 265, JP-B 51-1420, JP 52-6523, JP Sho 58-114036, 59-5246, 61-73152, 61-86750, 61-90155, 61-90156, 61-172246, etc. It can be synthesized by the method described or a method analogous thereto.

  For the method for synthesizing the group of the general formula (II-3), for example, JP-B-50-25,337 can be referred to. For example, it is also possible to synthesize from those sold under the trade name such as “Tinubin 109” by Ciba Specialty Chemicals. The group of the general formula (II-4) is referred to, for example, U.S. Pat. No. 3,785,827, and the group of the general formula (II-5) is referred to, for example, JP-A-5-4449. The group of the general formula (II-6) is referred to, for example, Japanese Patent Publication No. 48-30,492, and the group of the general formula (II-7) is, for example, Journal of Organic Chemistry, Vol. 23, page 1344 ( 1958) and can be synthesized. The groups represented by the general formulas (II-8) to (II-11) can be synthesized by the methods described in, for example, JP-A-2-188,573 and European Patent Publication No. 0684278A1. Commercial products can also be used. Specifically, it can be synthesized from the Whitefuluor product group manufactured by Sumitomo Chemical, the Hakkol product group manufactured by Showa Chemical, the Hostalux product group manufactured by Hoechst, and the Kayalight product group manufactured by Nippon Kayaku.

Specific examples of the groups represented by formulas (II-1) to (II-11) of the present invention are shown below, but the groups that can be employed in the present invention are not limited to these. . Note that a hydrogen atom in the compound shown here is detached to form a bond with L ¹⁰ .

  Of the substituents (II-1) to (II-11), preferably (II-1), (II-2), (II-3), (II-4), (II-5) and (II) -8), more preferably (II-1), (II-2), (II-3) and (II-4), most preferably (II-1) and (II-3). is there.

In the general formula (I), R ¹¹ , R ¹² , R ¹³ and R ¹⁴ each independently represents a substituent, and examples of the substituent include those of the aforementioned substituted alkyl group, substituted alkenyl group, substituted alkynyl group and substituted aralkyl group. The thing similar to what was mentioned as an example of the substituent of an alkyl part is mentioned. R ¹¹ , R ¹² , R ¹³ and R ¹⁴ are preferably halogen atoms, alkyl groups, alkenyl groups, alkynyl groups, aryl groups, cyano groups, hydroxyl groups, nitro groups, carboxyl groups, alkoxy groups, aryloxy groups, silyloxy groups , Heterocyclic oxy group, acyloxy group, carbamoyloxy group, alkoxycarbonyloxy group, aryloxycarbonyloxy group, amino group, acylamino group, aminocarbonylamino group, alkoxycarbonylamino group, aryloxycarbonylamino group, sulfamoylamino Group, alkyl and arylsulfonylamino group, mercapto group, alkylthio group, arylthio group, heterocyclic thio group, sulfamoyl group, sulfo group, alkyl and arylsulfinyl group, alkyl and arylsulfur group Nyl group, acyl group, aryloxycarbonyl group, alkoxycarbonyl group, carbamoyl group, imide group, phosphino group, phosphinyl group, phosphinyloxy group, phosphinylamino group, silyl group, more preferably a halogen atom, Alkyl group, aryl group, cyano group, hydroxyl group, nitro group, carboxyl group, alkoxy group, aryloxy group, silyloxy group, heterocyclic oxy group, acyloxy group, carbamoyloxy group, amino group, acylamino group, aminocarbonylamino group , Alkoxycarbonylamino group, aryloxycarbonylamino group, sulfamoylamino group, alkyl and arylsulfonylamino group, mercapto group, alkylthio group, arylthio group, heterocyclic thio group, sulfamoyl group, sulfo group Alkyl and arylsulfinyl groups, alkyl and arylsulfonyl groups, carbamoyl groups, imide groups, phosphino groups, phosphinyl groups, phosphinyloxy groups, phosphinylamino groups, and silyl groups, more preferably halogen atoms and alkyl groups , Aryl group, hydroxyl group, alkoxy group, aryloxy group, amino group, mercapto group, alkylthio group, arylthio group, sulfamoyl group, sulfo group, alkyl and arylsulfinyl group, alkyl and arylsulfonyl group, more preferably halogen An atom, an alkyl group, an aryl group, an alkoxy group, an aryloxy group, an alkylthio group, and an arylthio group, more preferably a halogen atom, an alkyl group having 1 to 20 carbon atoms, and an aryl group having 6 to 20 carbon atoms An alkoxy group having 1 to 20 carbon atoms, an aryloxy group having 6 to 20 carbon atoms, an alkylthio group having 1 to 20 carbon atoms, and an arylthio group having 6 to 20 carbon atoms, more preferably an alkyl group having 1 to 8 carbon atoms. An aryl group having 6 to 10 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, an alkylthio group having 1 to 8 carbon atoms, and an arylthio group having 6 to 10 carbon atoms, Preferred are an alkoxy group having 1 to 6 carbon atoms, an aryloxy group having 6 to 8 carbon atoms, an alkylthio group having 1 to 6 carbon atoms, and an arylthio group having 6 to 8 carbon atoms, and most preferably 1 to 4 carbon atoms. An alkoxy group;
Also, in the case of n11~n14 is 2 or more, it is also preferable that adjacent R ¹¹ to R ¹⁴ are combined to form a fused benzene ring.

n11 to n14 are preferably 0 to 2, more preferably 2, and adjacent R ^{11 to} R ¹⁴ are bonded to each other to form a condensed benzene ring. n10 is preferably 1 to 8, more preferably 4 to 8, still more preferably 6 to 8, and most preferably 8.

M ¹ is preferably 2 hydrogen atoms, 2 Li ⁺ , 2 Na ⁺ , 2 K ⁺ , 2 Rb ⁺ , 2 Cs ⁺ and Be ²⁺ , Mg ²⁺ , Ca ²⁺ , Ti ²⁺ , Mn ²⁺ , Fe ²⁺ , Co ²⁺ , Ni ²⁺ , Cu ²⁺ , Zn ²⁺ , Ru ²⁺ , Rh ²⁺ , Pd ²⁺ , Pt ²⁺ , Ba ²⁺ , Cd ²⁺ , Hg ²⁺ , Pb ²⁺ , Sn ²⁺ , Al—Cl, Al—Br, Al—F, Al—I, Ga—Cl, Ga—F, Ga—I, Ga—Br, In -Cl, In-Br, In- I, In-F, Tl-Cl, Tl-Br, Tl-I, Tl-F, Mn-OH, Fe-Cl, Ru-Cl, CrCl 2, SiCl 2, SiBr _{2, SiF 2, SiI 2,} ZrCl 2, GeCl 2, GeBr 2, GeI 2, GeF 2, SnCl 2, SnBr 2, SnI 2, SnF 2, TiCl 2, TiBr 2, T _{F 2, Si (OH) 2} , Ge (OH) 2, Zr (OH) 2, Mn (OH) 2, Sn (OH) 2, TiR 2, CrR 2, SiR 2, SnR 2, GeR 2, Si ( OR) ₂ , Sn (OR) ₂ , Ge (OR) ₂ , Ti (OR) ₂ , Cr (OR) ₂ , Sn (SR) ₂ , Ge (SR) ₂ [R represents an aliphatic group or an aromatic group. VO, MnO, TiO, more preferably 2 hydrogen atoms, 2 Li ⁺ , 2 Na ⁺ , 2 K ⁺ , 2 Rb ⁺ and Be ²⁺ , Mg ^{2 +} , Ca ²⁺ , Ti ²⁺ , Mn ²⁺ , Fe ²⁺ , Co ²⁺ , Ni ²⁺ , Cu ²⁺ , Zn ²⁺ , Ru ²⁺ , Rh ²⁺ , Pd ²⁺ , Pt ²⁺ , ^{Ba 2+, Sn 2+, Al-} Cl, Al-Br, Ga-Cl, Ga-F, Ga-I, Ga-Br, In-Cl, In-Br, Tl-Cl, Tl-Br, Mn- OH, Fe _{-Cl, Ru-Cl, CrCl 2} , SiCl 2, SiBr 2, ZrCl 2, GeCl 2, GeBr 2, SnCl 2, SnBr 2, TiCl 2, TiBr 2, Si (OH) 2, Ge (OH) 2, Zr (OH) ₂ , Mn (OH) ₂ , Sn (OH) ₂ , TiR ₂ , CrR ₂ , SiR ₂ , SnR ₂ , GeR ₂ , Si (OR) ₂ , Sn (OR) ₂ , Ge (OR) ₂ , Ti (OR) ₂ , Cr (OR) ₂ , Sn (SR) ₂ , Ge (SR) ₂ [R represents an aliphatic group or aromatic group], VO, MnO, TiO, more preferably 2 Hydrogen atoms, 2 Li ⁺ , 2 Na ⁺ , 2 K ⁺ , and Be ²⁺ , Mg ²⁺ , Ca ²⁺ , Ti ²⁺ , Mn ²⁺ , Fe ²⁺ , Co ^{2+ , Ni 2+, Cu 2+, Zn} 2+, Ru 2+, Rh 2+, Pd 2+, Pt 2+, Ba 2+, Sn 2+, Al-C , Ga-Cl, In-Cl , Tl-Cl, Mn-OH, Fe-Cl, Ru-Cl, CrCl 2, SiCl 2, ZrCl 2, GeCl 2, TiCl 2, Si (OH) 2, Ge (OH) ₂ , Zr (OH) ₂ , Mn (OH) ₂ , TiR ₂ , CrR ₂ , SiR ₂ , GeR ₂ , Si (OR) ₂ , Ge (OR) ₂ , Ti (OR) ₂ , Cr (OR) ₂ [ R represents an aliphatic group or an aromatic group], VO, MnO or TiO. Still more preferred M ¹ is two hydrogen atoms, Mn ²⁺ , VO, Zn ²⁺ or Cu ²⁺ , most preferably VO, Zn ²⁺ or Cu ²⁺ .

L ¹⁰ represents a divalent group, preferably —O—, —N (R ²¹¹ ) —, —S—, —C (R ²¹² ) (R ²¹³ ) —, —CO—, —CO—N (R ²¹⁴ ) —, —SO—, —SO ₂ —, —SO ₂ N (R ²¹⁵ ) — or a combination of these linking groups, more preferably each of these linking groups or these linking groups is represented by 2 One of the combined a group, more preferably the linking group thereof, more preferably ^{-O -, - N (R 211} ) -, - S -, - SO -, - SO 2 - or -SO ₂ N ( ^R215 )-, more preferably -O-, -N ( ^R211 )-, and -S-. Here, R ²¹¹ , R ²¹² , R ²¹³ , R ²¹⁴ and R ²¹⁵ represent a hydrogen atom, an aliphatic group, an aromatic group or a heterocyclic group. Preferred R ²¹¹ , R ²¹² , R ²¹³ , R ²¹⁴ and R ²¹⁵ are a hydrogen atom, an aliphatic group having 1 to 20 carbon atoms, an aromatic group having 6 to 20 carbon atoms or a heterocyclic group having 4 to 20 carbon atoms. More preferably a hydrogen atom, an alkyl group having 1 to 10 carbon atoms or a phenyl group having 6 to 10 carbon atoms, more preferably a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, most preferably a hydrogen atom. is there.

M ³ in the general formula (III) has the same meaning as M ¹ in the general formula (I), and the preferred range is also the same.

R ^{321 to} R ³³⁶ in the general formula (III) each independently represents a hydrogen atom or a substituent. The substituent has the same meaning as R ^11, R ^12, R ¹³ and R ¹⁴ in the above general formula (I), most preferred R ³²¹ to R ³³⁶ is a hydrogen atom.

At least one of the OR ³¹¹ ~OR ³¹⁸ in the general formula (III) represent the L ¹⁰ -R ¹⁰ group having the same meaning as in Formula (I), each independently R ³¹¹ to R ³¹⁸ in the remaining OR ³¹¹ ~OR ³¹⁸ is Represents a substituent.

  Specific examples of the compounds represented by the general formulas (I) and (III) are shown below, but the compounds of the present invention are not limited thereto.

The phthalocyanine compound of the present invention has excellent light resistance as shown in Examples and Test Examples described later.
Moreover, the phthalocyanine compound of the present invention exhibits excellent solubility in a solvent. That is, it exhibits excellent solubility in organic solvents, inorganic solvents, water, or mixtures thereof. Examples of the organic solvent include amide solvents (for example, N, N-dimethylformamide, N, N-dimethylacetamide, 1-methyl-2-pyrrolidone), sulfone solvents (for example, sulfolane) sulfoxide solvents (for example, dimethyl sulfoxide), and ureido. Solvent (eg, tetramethylurea), ether solvent (eg, dioxane, tetrahydrofuran, cyclopentylmethyl ether), ketone solvent (eg, acetone, cyclohexanone), hydrocarbon solvent (eg, toluene, xylene, n-decane), halogen type Solvent (eg, tetrachloroethane, chlorobenzene, chloronaphthalene), alcohol solvent (eg, methanol, ethanol, isopropyl alcohol, ethylene glycol, cyclohexanol, phenol), pyridine Solvent (eg, pyridine, γ-picoline, 2,6-lutidine), ester solvent (eg, ethyl acetate, butyl acetate), carboxylic acid solvent (eg, acetic acid, propionic acid), nitrile solvent (eg, acetonitrile), sulfonic acid Examples of the solvent include a system solvent (for example, methanesulfonic acid) and an amine solvent (for example, triethylamine and tributylamine). Examples of the inorganic solvent include sulfuric acid and phosphoric acid. Preferred solvents exhibiting higher solubility are amide solvents, sulfone solvents, sulfoxide solvents, ureido solvents, ether solvents, ketone solvents, halogen solvents, alcohol solvents, ester solvents, nitrile solvents. is there.

  Next, a method for producing the compound of the present invention represented by the general formulas (I) and (III) will be described.

  General formulas (I) and (III) can be synthesized by carrying out a cyclization reaction in the presence of a metal compound using the corresponding phthalic acid or a derivative thereof (an acid anhydride, diamide, dinitrile, etc.). it can. This cyclization reaction can be performed with reference to Chemistry-A. European Journal, Vol. 9, pages 5123-5134 (published in 2003). At this time, it is preferable that a catalyst (for example, ammonium molybdate) and urea coexist. Alternatively, after a metal-free phthalocyanine is synthesized once using a lithium compound, it can be synthesized using a metal compound as described later, and this method is more preferable for synthesizing a metal body of naphthalocyanine.

  When synthesizing the compounds represented by the general formulas (I) and (III) using a metal-free phthalocyanine and a metal compound, the ratio of the raw materials is 0.1 mol of the metal compound per 1 mol of the metal-free phthalocyanine. It is preferable that it is 1-10 mol, More preferably, it is 0.5-5 mol, More preferably, it is 1-3 mol. As the metal compound, inorganic and organic metal compounds can be used, and examples thereof include halides (for example, chlorinated products, brominated products), sulfates, nitrates, cyanides, acetates, metal acetylacetonates, and the like. Preferred are chlorides, sulfates, cyanides and acetates, more preferred are chlorides and acetates, and most preferred are acetates.

  Examples of the solvent used in the reaction include amide solvents (for example, N, N-dimethylformamide, N, N-dimethylacetamide, 1-methyl-2-pyrrolidone), sulfone solvents (for example, sulfolane), sulfoxide solvents (for example, dimethyl sulfoxide). ), Ether solvents (eg dioxane, cyclopentyl methyl ether), ketone solvents (eg acetone, cyclohexanone), hydrocarbon solvents (eg toluene, xylene), halogen solvents (eg tetrachloroethane, chlorobenzene), alcohol solvents ( For example, 1-butanol, ethylene glycol, cyclohexanol) or a pyridine solvent (for example, pyridine, γ-picoline, 2,6-lutidine) is used alone or in combination. Of these, preferred are amide solvents, sulfone solvents, ether solvents, hydrocarbon solvents, halogen solvents, pyridine solvents, and more preferred sulfone solvents, ether solvents, hydrocarbon solvents, halogen solvents. More preferred are ether solvents, hydrocarbon solvents, halogen solvents, more preferred are halogen solvents, and chlorobenzene is most preferred.

  The reaction temperature is generally −30 to 250 ° C., preferably 0 to 200 ° C., more preferably 20 to 150 ° C., further preferably 50 to 100 ° C., and the reaction time is usually in the range of 5 minutes to 30 hours.

  Hereinafter, the features of the present invention will be described more specifically with reference to examples and test examples. The materials, amounts used, ratios, processing details, processing procedures, and the like shown in the following examples can be changed as appropriate without departing from the spirit of the present invention. Therefore, the scope of the present invention should not be construed as being limited by the specific examples shown below.

(Example 1: Synthesis of exemplary compound A-4d)
Exemplified Compound A-4d was synthesized based on the following formula.

  100 g of the compound (Z-1A), 72 g of ethylene carbonate, 6.9 g of tetraethylammonium bromide, and 200 ml of DMF were placed in a 2 L three-necked flask and stirred at an internal temperature of 140 ° C. for 6 hours. Then, the internal temperature was cooled to 55 ° C., and 750 ml of ethyl acetate and 1 L of water were added to extract the organic layer. The organic layer was concentrated on a rotary evaporator to give 380 g of residue. The residue was brought to an internal temperature of 50 ° C., 1 L of hexane was added dropwise over 30 minutes with stirring, and the mixture was cooled to −10 ° C. The precipitated crystals were filtered to obtain 98.1 g of compound (Z-1B) (yield 76%).

  90 g of compound (Z-1B), 60.3 g of triethylamine, and 180 ml of DMF were placed in a 1 L three-necked flask and cooled to an internal temperature of 5 ° C. or lower. Next, 62.0 g of methanesulfonyl chloride was added dropwise over 1 hour with stirring under ice cooling, followed by stirring at room temperature for 1 hour. 350 ml of water and 350 ml of ethyl acetate were added to the reaction product, and the organic layer was extracted. The obtained organic layer was further washed twice with 400 ml of water, dried over anhydrous magnesium sulfate, and concentrated on a rotary evaporator.

  To the obtained concentrate, 200 ml of DMF, 43.5 g of the compound (Z-1C), and 87.0 g of potassium carbonate were added, and the mixture was stirred at an internal temperature of 120 ° C. for 5 hours in a 1 L three-necked flask. After cooling to an internal temperature of 50 ° C., 200 ml of water was added to cool to 10 ° C. After stirring at 10 ° C. for 1 hour, the resulting slurry was filtered and washed with 300 ml of methanol and 300 ml of water to obtain 85.6 g of compound (Z-1D) (yield 73%).

  45 g of the compound (Z-1D), 20.1 g of lithium chloride, 12.8 g of sodium methoxide, and 200 ml of butanol were placed in a 2 L three-necked flask and stirred at 110 ° C. for 4 hours. Next, 8.7 g of hydroquinone was added and stirred at the same temperature for 30 minutes. Thereafter, the mixture was cooled to 50 ° C., and 400 ml of water, 30 ml of acetic acid and 1 L of chloroform were added to extract the organic layer. Subsequently, it was washed with 400 ml of water twice, and the obtained organic layer was dried over anhydrous magnesium sulfate and concentrated with a rotary evaporator. The obtained product was purified by silica gel column chromatography to obtain 20.27 g of the exemplified compound (A-4d) (yield 45%). When the obtained compound was measured by MS spectrum, a peak corresponding to the molecular weight was obtained.

(Example 2: Synthesis of exemplary compound A-4c)
20 g of exemplary compound (A-4d) was dissolved in 300 ml of toluene, 2.0 g of copper (II) acetate was added, and the mixture was stirred for 5 hours at an internal temperature of 80 ° C. in a 500 ml three-necked flask. 200 ml of water was added to the reaction solution, and the organic layer was extracted. Washing was performed twice with 200 ml of water, and the organic layer was dried over magnesium sulfate and then concentrated with a rotary evaporator to obtain 19.5 g of Exemplified Compound (A-4c) (yield 95%).
When the obtained compound was measured by MS spectrum, a peak corresponding to the molecular weight was obtained.

(Example 3: Synthesis of exemplary compound A-3b)
Exemplified Compound A-3b was synthesized based on the following formula.

  100 g of compound (Z-3A), 88 g of ethylene carbonate, 8.5 g of tetraethylammonium bromide, and 200 ml of DMF were placed in a 2 L three-necked flask and stirred at an internal temperature of 140 ° C. for 6 hours. Then, the internal temperature was cooled to 55 ° C., and 750 ml of ethyl acetate and 1 L of water were added to extract the organic layer. The organic layer was concentrated on a rotary evaporator to give 380 g of residue. The residue was brought to an internal temperature of 50 ° C., 1 L of hexane was added dropwise over 30 minutes with stirring, and the mixture was cooled to −10 ° C. The precipitated crystals were filtered to obtain 112.4 g of Compound (Z-3B) (yield 83%).

  77.1 g of compound (Z-3B), 60.3 g of triethylamine, and 160 ml of DMF were placed in a 1 L three-necked flask and cooled to an internal temperature of 5 ° C. or lower. Next, 62.0 g of methanesulfonyl chloride was added dropwise over 1 hour with stirring under ice cooling, followed by stirring at room temperature for 1 hour. 350 ml of water and 350 ml of ethyl acetate were added to the reaction product, and the organic layer was extracted. The obtained organic layer was further washed twice with 400 ml of water, dried over anhydrous magnesium sulfate, and concentrated on a rotary evaporator.

  To the obtained concentrate, 200 ml of DMF, 43.5 g of the compound (Z-3C), and 87.0 g of potassium carbonate were added, and the mixture was stirred at an internal temperature of 120 ° C. for 5 hours in a 1 L three-necked flask. After cooling to an internal temperature of 50 ° C., 200 ml of water was added to cool to 10 ° C. After stirring at 10 ° C. for 1 hour, the resulting slurry was filtered and washed with 300 ml of methanol and 300 ml of water to obtain 81.4 g of compound (Z-3D) (yield 77%).

  38.4 g of compound (Z-3D), 200 ml of butanol, 12.6 g of DBU and 3.6 g of zinc acetate were placed in a 1 L three-necked flask and heated at an internal temperature of 110 ° C. for 6 hours. The internal temperature was cooled to 60 ° C., and 500 ml of ethyl acetate and 300 ml of water were added to extract the organic layer. The organic layer was dried over magnesium sulfate and concentrated on a rotary evaporator. The obtained product was purified by silica gel column chromatography to obtain 25.5 g of exemplary compound (A-3b) (yield: 64.3%). When the obtained compound was measured by MS spectrum, a peak corresponding to the molecular weight was obtained.

(Example 4: Synthesis of exemplary compound C-3c)
Exemplified compound C-3c was synthesized based on the following formula.

  55 g of 1,3-dichloroaniline and 500 ml of 2 mol / L hydrochloric acid were placed in a 2 L three-necked flask, cooled to 5 ° C. or less, and 150 ml of 2 mol / L sodium nitrite aqueous solution was added dropwise over 30 minutes. Next, 67.6 g of compound (Z-4A) was added, and the mixture was stirred at 30 ° C. for 2 hours. Crystals precipitated after the reaction were filtered under reduced pressure and washed with 500 ml of water to obtain 88 g of compound (Z-4B) (yield 65%).

  50 g of the compound (Z-4B), 0.1 g of palladium-carbon powder, and 250 ml of ethanol were placed in a 500 ml autoclave and adjusted to a hydrogen pressure of 1 MPa. After reacting at room temperature for 1 hour, 300 ml of water was added, and the resulting crystals were filtered to obtain 28.7 g of compound (Z-4C) (yield 95%).

  25 g of compound (Z-4C), 18.6 g of triethylamine, and 350 ml of ethyl acetate were placed in a 1 L three-necked flask, and 14.7 g of 4-chlorobutanoic acid chloride was added dropwise at room temperature over 30 minutes. Then, after stirring for 2 hours at room temperature, 200 ml of water was added to extract the organic layer. The organic layer was washed twice with 200 ml of water, dried over anhydrous sodium sulfate, and concentrated on a rotary evaporator. The obtained product was purified by silica gel column chromatography to obtain 32.7 g of compound (Z-4D) (yield 91%).

  30 g of compound (Z-4D), 8.8 g of compound (Z-4E), 17.6 g of potassium carbonate, 0.5 g of potassium iodide and 100 ml of DMF were placed in a 500 ml three-necked flask and stirred at an internal temperature of 110 ° C. for 5 hours. Went. When the internal temperature was cooled to 50 ° C., 150 ml of water was added, and the internal temperature was adjusted to 0 ° C. over 2 hours with stirring. The precipitate was separated by filtration under reduced pressure and washed with 100 ml of water and 100 ml of methanol to obtain 24.0 g of compound (Z-4F) (yield 69%).

  20 g of compound (Z-4F), 100 ml of butanol, 3.7 g of DBU, and 1.2 g of zinc acetate were placed in a 1 L three-necked flask and heated at an internal temperature of 110 ° C. for 6 hours. The internal temperature was cooled to 60 ° C., and 500 ml of ethyl acetate and 300 ml of water were added to extract the organic layer. The organic layer was dried over magnesium sulfate and concentrated on a rotary evaporator. By purifying the obtained product by silica gel column chromatography, 11.2 g (yield 55%) of the exemplary compound (C-3c) was obtained. When the obtained compound was measured by MS spectrum, a peak corresponding to the molecular weight was obtained.

Example 5 Synthesis of Exemplary Compound A-14e
Exemplified Compound A-14e was synthesized based on the following formula.

  126.1 g of compound (Z-5A), 205.6 g of butyl bromide, 207.3 g of potassium carbonate and 300 ml of sulfolane were placed in a 1 L three-necked flask and stirred at an internal temperature of 90 ° C. for 4 hours. After cooling to an internal temperature of 50 ° C., 300 ml of water was added dropwise over 1 hour and cooled to 10 ° C. over 2 hours. After stirring at 10 ° C. for 1 hour, the resulting slurry was filtered and washed with 300 ml of methanol and 300 ml of water to obtain 154.5 g of compound (Z-5B) (yield 80%).

  64.5 g of compound (Z-5B), 67.3 g of compound (Z-3B) described in Example 3, 50.9 g of lithium chloride, 28.8 g of tert-butoxy sodium, and 300 ml of butanol were placed in a 2 L three-necked flask. Heating was performed at 130 ° C. for 5 hours. Thereafter, the mixture was cooled to 50 ° C., and 400 ml of water, 30 ml of acetic acid and 1 L of chloroform were added to extract the organic layer. Subsequently, it was washed twice with 400 ml of water, and the obtained organic layer was dried over anhydrous magnesium sulfate and concentrated to 250 g with a rotary evaporator. To the concentrate, 400 ml of hexane was added at an internal temperature of 50 ° C., and the mixture was cooled to −10 ° C. over 2 hours with stirring. Then, it left still at -10 degreeC for 12 hours, the produced | generated crystal | crystallization was vacuum-filtered, and it wash | cleaned with 300 ml of methanol. The obtained compound was a compound in which the butoxy group in the side chain portion of (A-14e) was further replaced with 1 to 5 compounds (Z-3B) in addition to the exemplified compound (A-14e). When these MS spectra were measured, peaks corresponding to the molecular weights of the respective compounds were obtained. This mixture was separated by silica gel column chromatography to obtain 24.2 g of exemplary compound (A-14e) (yield 35%). When the obtained compound was measured by MS spectrum, a peak corresponding to the molecular weight was obtained.

(Test Example 1: Light resistance test)
Exemplified compounds (A-4d) (A-4c) (A-3b) (C-3c) (A-14e) obtained in Examples 1 to 5, and 5,9,14,18,23 for comparison , 27, 32, 36-octabutoxy-2,3-naphthalocyanine (comparative example) was subjected to a light resistance test according to the following procedure.
Add 100 ml of chloroform to 0.1 g of each compound and 10 g of polystyrene, stir and dissolve at 40 ° C. for 15 minutes, apply the resulting solution to a glass plate, blow dry at room temperature, and use a near infrared absorption filter sample It was created. Each sample was irradiated with a xenon lamp at 95,000 lux for 3 days, the concentration of the spectral absorption maximum wavelength of the compound before and after irradiation was measured, and the residual ratio was determined by the following formula to determine the light resistance (light fastness) ) Was evaluated. The results are shown in Table 1. When the residual ratio was 0.01 or more, it was judged that the present invention had the intended light resistance.

Moreover, exemplary compound (A-20d) (B-4e) (C-7c) (D-1a) (D-2b) (D-3b) (D-4c) (D-11c) (D-12e) ( D-13f) (D-14e) was also subjected to a light resistance test in the same manner, and these compounds were also subjected to Comparative Examples 5, 9, 14, 18, 23, 27, 32, 36-octa. High light resistance was confirmed as compared with butoxy-2,3-naphthalocyanine.
From the above, it was confirmed that the compound of the present invention has high light resistance.

(Test Example 2: Absorption wavelength measurement and solubility test)
Exemplified compounds (A-4d) (A-4c) (A-3b) (C-3c) (A-14e) obtained in Examples 1 to 5 in THF solvent at a concentration of 0.4 to 4 μmol / L. The maximum absorption wavelength at 25 ° C. was measured using a spectral absorption measurement device (manufactured by Hitachi High-Technologies Corporation, U-4100 spectrophotometer). As a result, it was confirmed that any of these compounds has a maximum absorption wavelength in the near infrared region.
Moreover, the solubility with respect to chloroform was evaluated about the exemplary compound (A-4d) (A-4c) (A-3b) (C-3c) (A-14e) obtained in Examples 1-5. As a result, it was confirmed that 1 g of these compounds were completely dissolved in 100 ml of chloroform and had sufficient solubility.

  The phthalocyanine compound of the present invention has characteristics that it has absorption in the near infrared region, has good solubility, and is excellent in light resistance. For this reason, the phthalocyanine compound of the present invention is an optical fiber such as a near-infrared absorbing filter, a near-infrared absorbing colored resin composition (for example, paint or ink), a liquid crystal display element, a photothermal conversion material, an optical card, an optical recording medium, and protective glasses. It can be used in a wide range of electronics-related materials and products. Therefore, the industrial applicability of the present invention is high.

Claims (4)

A phthalocyanine compound represented by formula (I).

[In the general formula (I), R ¹⁰ has a spectral absorption maximum wavelength at 270 to 750 nm in a solution of compound R ¹⁰ -H of 470 nm or less, or compound R ¹⁰ -H is a singlet oxygen scavenger, radical Represents an atomic group satisfying the condition of being a trapping agent or an antioxidant, L ¹⁰ represents a single bond or a divalent group, n10 represents an integer of 1 to 16, and when n10 is 2 or more, each L ¹⁰ and R ¹⁰ may be the same or different. (L ¹⁰ -R ¹⁰ ) is substituted at a substitutable position in the structure in []. R ¹¹ to R ¹⁴ each independently represent a (L ¹⁰ -R ¹⁰⁾ other than the substituent each independently represent an integer of 0 to 4 N11～n14. When n11 to n14 is 2 or more, adjacent R ^{11 to} R ¹⁴ may be connected to each other to form a ring. M ¹ represents two atoms selected from the group consisting of a hydrogen atom and a monovalent metal atom, a divalent metal atom, or a divalent substituted metal atom including a trivalent or tetravalent metal atom. ] The compound according to claim 1, wherein R ^{10 in the} general formula (I) is a group represented by any of the following structural formulas.

[In the general formula (II-1), R ²⁰¹¹ represents a hydrogen atom, an aliphatic group, an aromatic group, a heterocyclic group bonded by a carbon atom or a hydrolyzable protecting group, and R ²⁰¹² , R ²⁰¹³ , R ²⁰¹⁴ , R ²⁰¹⁵ and R ²⁰¹⁶ each independently represents a hydrogen atom or a substituent, and R ²⁰¹¹ and R ²⁰¹² , R ²⁰¹² and R ²⁰¹³ , R ²⁰¹³ and R ²⁰¹⁴ , R ²⁰¹⁴ and R ²⁰¹⁵ , R ²⁰¹⁵ and R ²⁰¹⁶ and R ^2016. And R ²⁰¹¹ may combine with each other to form a ring.
In general formula (II-2), R ²⁰²¹ represents a hydrogen atom, an aliphatic group, an acyl group, a sulfonyl group, a sulfinyl group, an oxy radical group or a hydroxyl group, and Q forms a 5-membered, 6-membered or 7-membered ring. R ²⁰²² , R ²⁰²³ , R ²⁰²⁴ and R ²⁰²⁵ each independently represents a hydrogen atom, an aliphatic group, an aromatic group or a heterocyclic group bonded with a carbon atom, ²⁰²¹ and R ²⁰²² , R ²⁰²² and R ²⁰²³ , R ²⁰²⁴ and R ^2025, and R ²⁰²¹ and R ²⁰²⁴ may be bonded to each other to form a ring.
In general formula (II-3), R ²⁰³¹ , R ²⁰³² , R ²⁰³³ and R ²⁰³⁴ each independently represent a hydrogen atom or a substituent, and R ²⁰³⁵ is bonded by a hydrogen atom, an aliphatic group, an aromatic group or a carbon atom. R ²⁰³¹ and R ²⁰³² , R ²⁰³² and R ^2033, and R ²⁰³³ and R ²⁰³⁴ may be bonded to each other to form a ring.
In general formula (II-4), ^R2041 , ^R2042 , ^R2043 , ^R2044 , ^R2045 , ^R2046 , ^R2047 , ^R2048 , ^R2049 and ^R2050 each independently represents a hydrogen atom or a substituent, R ²⁰⁴¹ and R ^2042, R ²⁰⁴² and R ^2043, R ²⁰⁴³ and R ^2044, R ²⁰⁴⁴ and R ^2045, R ²⁰⁴⁶ and R ^2047, R ²⁰⁴⁷ and R ^2048, R ²⁰⁴⁸ and R ²⁰⁴⁹ and R ²⁰⁴⁹ and R ²⁰⁵⁰ are coupled to each other To form a ring.
In general formula (II-5), ^R2051 , ^R2052 , ^R2053 , ^R2054 , ^R2055 , ^R2056 , ^R2057 , ^R2058 , ^R2059 and ^R2060 each independently represents a hydrogen atom or a substituent, R ²⁰⁵¹ and R ²⁰⁵² , R ²⁰⁵² and R ²⁰⁵³ , R ²⁰⁵³ and R ²⁰⁵⁴ , R ²⁰⁵⁴ and R ²⁰⁵⁵ , R ²⁰⁵⁶ and R ²⁰⁵⁷ , R ²⁰⁵⁷ and R ²⁰⁵⁸ , R ²⁰⁵⁸ and R ^2059, and R ²⁰⁵⁹ and R ²⁰⁶⁰ are bonded to each other. To form a ring.
In the general formula (II-6), R ²⁰⁶¹ , R ²⁰⁶² , R ²⁰⁶³ , R ²⁰⁶⁴ , R ²⁰⁶⁵ , R ²⁰⁶⁶ , R ²⁰⁶⁷ , R ²⁰⁶⁸ , R ²⁰⁶⁹ and R ²⁰⁷⁰ each independently represents a hydrogen atom or a substituent, R ²⁰⁶¹ and R ²⁰⁶² , R ²⁰⁶² and R ²⁰⁶³ , R ²⁰⁶³ and R ²⁰⁶⁴ , R ²⁰⁶⁴ and R ²⁰⁶⁵ , R ²⁰⁶⁶ and R ²⁰⁶⁷ , R ²⁰⁶⁷ and R ²⁰⁶⁸ , R ²⁰⁶⁸ and R ^2069, and R ²⁰⁶⁹ and R ²⁰⁷⁰ are bonded to each other. To form a ring. X ²⁰⁶¹ represents a hydrogen atom, an aliphatic group, an aromatic group, or a heterocyclic group bonded with a carbon atom.
In general formula (II-7), R ²⁰⁷¹ , R ²⁰⁷² , R ²⁰⁷³ , R ²⁰⁷⁴ , R ²⁰⁷⁵ , R ²⁰⁷⁶ , R ²⁰⁷⁷ , R ²⁰⁷⁸ , R ²⁰⁷⁹ and R ²⁰⁸⁰ each independently represents a hydrogen atom or a substituent, R ²⁰⁷¹ and R ²⁰⁷² , R ²⁰⁷² and R ²⁰⁷³ , R ²⁰⁷³ and R ²⁰⁷⁴ , R ²⁰⁷⁴ and R ²⁰⁷⁵ , R ²⁰⁷⁶ and R ²⁰⁷⁷ , R ²⁰⁷⁷ and R ²⁰⁷⁸ , R ²⁰⁷⁸ and R ²⁰⁷⁹ and R ²⁰⁷⁹ and R ²⁰⁸⁰ are bonded to each other To form a ring.
In general formula (II-8), R ²⁰⁸¹ , R ²⁰⁸² , R ²⁰⁸³ , R ²⁰⁸⁴ , R ²⁰⁸⁵ and R ²⁰⁸⁶ each independently represent a hydrogen atom or a substituent. R ²⁰⁸¹ and R ²⁰⁸² , R ²⁰⁸² and R ²⁰⁸³ , R ²⁰⁸³ and R ²⁰⁸⁴ , R ²⁰⁸⁴ and R ^2085, and R ²⁰⁸⁵ and R ²⁰⁸⁶ may be bonded to each other to form a ring.
In General Formula (II-9), R ²⁰⁹¹ , R ²⁰⁹² , R ²⁰⁹³ , R ²⁰⁹⁴ , R ²⁰⁹⁵ , R ²⁰⁹⁶ , R ²⁰⁹⁷ and R ²⁰⁹⁸ each independently represent a hydrogen atom or a substituent, and R ²⁰⁹⁹ and R ²¹⁰⁰ are Represents a substituent. R ²⁰⁹¹ and R ²⁰⁹² , R ²⁰⁹² and R ²⁰⁹³ , R ²⁰⁹³ and R ²⁰⁹⁴ , R ²⁰⁹⁵ and R ²⁰⁹⁶ , R ²⁰⁹⁶ and R ²⁰⁹⁷ and R ²⁰⁹⁷ and R ²⁰⁹⁸ may be bonded to each other to form a ring. n2099 and n2100 each independently represents an integer of 0 to 4, when the n2099 and n2100 are 2 or more, plural R ²⁰⁹⁹ and R ²¹⁰⁰ may be the same or different.
In the general formula (II-10), R ²¹⁰¹ , R ²¹⁰² , R ²¹⁰³ , R ²¹⁰⁴ , R ²¹⁰⁶ , R ²¹⁰⁷ , R ²¹⁰⁸ and R ²¹⁰⁹ each independently represent a hydrogen atom or a substituent, and R ²¹⁰⁵ represents a substituent. To express. R ²¹⁰¹ and R ²¹⁰² , R ²¹⁰² and R ²¹⁰³ , R ²¹⁰³ and R ²¹⁰⁴ , R ²¹⁰⁶ and R ²¹⁰⁷ , R ²¹⁰⁷ and R ^2108, and R ²¹⁰⁸ and R ²¹⁰⁹ may be bonded to each other to form a ring. n2105 represents an integer of 0 to 6, and when n2105 is 2 or more, a plurality of R ²¹⁰⁵ may be the same or different.
In general formula (II-11), R ²¹¹¹ , R ²¹¹² , R ²¹¹³ , R ²¹¹⁴ , R ²¹¹⁵ , R ²¹¹⁶ , R ²¹¹⁷ , R ²¹¹⁸ , R ²¹¹⁹ and R ²¹²⁰ each independently represent a hydrogen atom or a substituent. R ²¹¹¹ and R ²¹¹² , R ²¹¹² and R ²¹¹³ , R ²¹¹³ and R ²¹¹⁴ , R ²¹¹⁵ and R ²¹¹⁶ , R ²¹¹⁷ and R ²¹¹⁸ , R ²¹¹⁸ and R ²¹¹⁹ and R ²¹¹⁹ and R ²¹²⁰ are bonded together to form a ring. May be.
However, any one of R ^{2011 to} R ^{2016 in} the general formula (II-1), any one of R ^{2021 to} R ^{2025 in} the general formula (II-2), R ^{2031 in the} general formula (II-3) Any one of -R ²⁰³⁵ , any one of R ²⁰⁴¹ -R ^{2050 in} the general formula (II-4), any one of R ²⁰⁵¹ -R ^{2060 in} the general formula (II-5), Any one of R ^{2061 to} R ²⁰⁷⁰ of II-6), any one of R ^{2071 to} R ²⁰⁸⁰ of general formula (II-7), and any of R ^{2081 to} R ²⁰⁸⁶ of general formula (II-8) Any one of R ^{2091 to} R ²¹⁰⁰ of the general formula (II-9), any one of R ^{2101 to} R ²¹⁰⁹ of the general formula (II-10), and the general formula (II-11) Any one of R ^{2111 to} R ²¹²⁰ is substituted by a single bond for bonding one hydrogen atom contained therein to L ¹⁰ . ]   3. The compound according to claim 1 or 2, wherein the compound represented by the general formula (I) has a 2,3-naphthalocyanine skeleton. The compound represented by said general formula (I) is a compound represented by the following general formula (III), The compound as described in any one of Claims 1-3 characterized by the above-mentioned.

[At least one OR ³¹¹ ~OR ³¹⁸ represents the L ¹⁰ -R ¹⁰ group having the same meaning as independently in the general formula (I), the fatty each independently R ³¹¹ to R ³¹⁸ in the remaining OR ³¹¹ ~OR ³¹⁸ Represents an aromatic group or an aromatic group. R ^{321 to} R ³³⁶ each independently represents a hydrogen atom or a substituent. M ³ represents a hydrogen atom, two atoms selected from the group consisting of monovalent metal atoms, a divalent metal atom, or a divalent substituted metal atom containing a trivalent or tetravalent metal atom. ]