WO2021200826A1 - 化合物 - Google Patents

化合物 Download PDF

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Publication number
WO2021200826A1
WO2021200826A1 PCT/JP2021/013306 JP2021013306W WO2021200826A1 WO 2021200826 A1 WO2021200826 A1 WO 2021200826A1 JP 2021013306 W JP2021013306 W JP 2021013306W WO 2021200826 A1 WO2021200826 A1 WO 2021200826A1
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Prior art keywords
ring
group
compound
formula
formulas
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PCT/JP2021/013306
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English (en)
French (fr)
Japanese (ja)
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悠司 淺津
浩司 久門
由紀 西上
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住友化学株式会社
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Priority to CN202180026579.7A priority Critical patent/CN115443265A/zh
Priority to KR1020227036875A priority patent/KR20220163974A/ko
Publication of WO2021200826A1 publication Critical patent/WO2021200826A1/ja

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/57—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C233/58—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/16—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and singly-bound oxygen atoms bound to the same carbon atom of an acyclic carbon skeleton
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    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/17—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and doubly-bound oxygen atoms bound to the same acyclic carbon skeleton
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    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/24—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the same saturated acyclic carbon skeleton
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    • C07C255/24—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the same saturated acyclic carbon skeleton
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    • C07C309/63—Esters of sulfonic acids
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    • C07C327/00—Thiocarboxylic acids
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    • C07C327/04—Monothiocarboxylic acids having carbon atoms of thiocarboxyl groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C327/12—Monothiocarboxylic acids having carbon atoms of thiocarboxyl groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of an unsaturated carbon skeleton containing rings
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
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    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
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    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
    • C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
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    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
    • C07D251/30—Only oxygen atoms
    • C07D251/32—Cyanuric acid; Isocyanuric acid
    • C—CHEMISTRY; METALLURGY
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D309/04—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
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    • C07D341/00—Heterocyclic compounds containing rings having three or more sulfur atoms as the only ring hetero atoms
    • C—CHEMISTRY; METALLURGY
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    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/40—Esters thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/16—Catalysts
    • C08G18/22—Catalysts containing metal compounds
    • C08G18/24—Catalysts containing metal compounds of tin
    • C08G18/242—Catalysts containing metal compounds of tin organometallic compounds containing tin-carbon bonds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
    • C08G18/3855—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur
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    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
    • C08G18/7614—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring
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    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/315—Compounds containing carbon-to-nitrogen triple bonds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/0008—Methine or polymethine dyes, e.g. cyanine dyes substituted on the polymethine chain
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    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/10—The polymethine chain containing an even number of >CH- groups
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    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/006—Preparation of organic pigments
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/04—Systems containing only non-condensed rings with a four-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/18—Systems containing only non-condensed rings with a ring being at least seven-membered
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
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Definitions

  • the present invention relates to a compound.
  • Blue light cut by mixing an absorber that absorbs light with a wavelength of 400 to 500 nm on the display surface, glasses, contact lenses, etc., or by laminating a layer containing an absorber that absorbs light with a wavelength of 400 to 500 nm. Functions can be added.
  • C.I. I. Quinoline compounds such as Solvent Yellow 33 may not have sufficient weather resistance.
  • the present invention includes the following inventions.
  • ring W 1 represents a ring structure having at least one substituent.
  • ring W 1 has the same meaning as above.
  • Each of 14 independently represents a ring structure, and the ring structure may have a substituent.
  • R 3 represents a monovalent substituent.
  • R 13 , R 23 , R 33 , R 43 , R 53 , R 63 and R 133 represent monovalent substituents.
  • R 1 and R 2 may be connected to each other to form a ring.
  • R 2 and R 3 may be connected to each other to form a ring.
  • R 3 and R 4 may be connected to each other to form a ring.
  • R 4 and R 5 may be connected to each other to form a ring.
  • R 12 and R 13 may be connected to each other to form a ring.
  • R 13 and R 14 may be connected to each other to form a ring.
  • R 14 and R 15 may be connected to each other to form a ring.
  • R 22 and R 23 may be connected to each other to form a ring.
  • R 23 and R 24 may be connected to each other to form a ring.
  • R 24 and R 25 may be connected to each other to form a ring.
  • R 32 and R 33 may be connected to each other to form a ring.
  • R 33 and R 34 may be connected to each other to form a ring.
  • R 34 and R 35 may be connected to each other to form a ring.
  • R 42 and R 43 may be connected to each other to form a ring.
  • R 43 and R 44 may be connected to each other to form a ring.
  • R 44 and R 45 may be connected to each other to form a ring.
  • R 52 and R 53 may be connected to each other to form a ring.
  • R 53 and R 54 may be connected to each other to form a ring.
  • R 54 and R 55 may be connected to each other to form a ring.
  • R 62 and R 63 may be connected to each other to form a ring.
  • R 63 and R 64 may be connected to each other to form a ring.
  • R 64 and R 65 may be connected to each other to form a ring.
  • R 71 and R 72 may be connected to each other to form a ring.
  • R 74 and R 75 may be connected to each other to form a ring.
  • R 81 and R 82 may be connected to each other to form a ring.
  • R 84 and R 85 may be connected to each other to form a ring.
  • R 91 and R 92 may be connected to each other to form a ring.
  • R 94 and R 95 may be connected to each other to form a ring.
  • R 101 and R 102 may be connected to each other to form a ring.
  • R 104 and R 105 may be connected to each other to form a ring.
  • R 111 and R 112 may be connected to each other to form a ring.
  • R 114 and R 115 may be connected to each other to form a ring.
  • R 121 and R 122 may be connected to each other to form a ring.
  • R 124 and R 125 may be connected to each other to form a ring.
  • R 131 and R 132 may be connected to each other to form a ring.
  • R 132 and R 133 may be connected to each other to form a ring.
  • R 133 and R 134 may be connected to each other to form a ring.
  • R 134 and R 135 may be connected to each other to form a ring.
  • R x1 , R x4 and R x7 each independently represent a single bond or a divalent linking group.
  • R x2 and R x5 each independently represent a trivalent linking group.
  • R x3 and R x6 each independently represent a tetravalent linking group.
  • At least one selected from R 1 , R 2 , R 3 , R 4 and R 5 is a cyano group, a nitro group, an alkyl halide group, an aryl halide group, -CO-R 1 , -CO-O.
  • R 9 (R 1 , R 2 , R 3 , R 3k , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are hydrocarbons that may have independent substituents, respectively. represents a group or a halogen atom), -.
  • OCF 3, -SCF 3, -SF 5, -SF 3, or a compound according to -SO are 3 H [2] or [3].
  • At least one selected from R 1 , R 2 , R 3 , R 4 and R 5 is a cyano group, a nitro group, -CO-R 1 , -CO-O-R 2 , -SO 2- R 9 (R 1 , R 2 and R 9 represent hydrocarbon groups or halogen atoms that may independently have substituents, respectively.), -SF 5 , -SF 3 , -SO 3 H, -SO 2
  • epsilon represents the gram extinction coefficient at the maximum absorption wavelength (lambda max).
  • ⁇ ( ⁇ max + 30 nm) represents the gram absorption coefficient at the maximum absorption wavelength ( ⁇ max) + 30 nm.
  • the unit of the gram extinction coefficient is L / (g ⁇ cm).
  • the present invention provides a novel compound that sufficiently absorbs light having a wavelength of around 440 nm and has high weather resistance.
  • the compound of the present invention is a compound containing an anion having a partial structure represented by the formula (X) (hereinafter, may be referred to as compound (X)).
  • compound (X) a compound containing an anion having a partial structure represented by the formula (X) (hereinafter, may be referred to as compound (X)).
  • ring W 1 represents a ring having at least one substituent.
  • Ring ring W 1 is not particularly limited. Ring W 1 may be a single ring or a condensed ring. Ring W 1 may be a hetero ring containing a hetero atom (for example, an oxygen atom, a sulfur atom, a nitrogen atom, etc.) as a constituent requirement of the ring, or an aliphatic hydrocarbon ring composed of a carbon atom and a hydrogen atom. There may be.
  • a hetero atom for example, an oxygen atom, a sulfur atom, a nitrogen atom, etc.
  • Ring W 1 is usually a ring having 5 to 18 carbon atoms, preferably having a 5- to 7-membered ring structure, and more preferably a 6-membered ring structure.
  • the ring W 1 preferably has a ring structure having 5 to 7 carbon atoms, and more preferably a ring structure having 6 carbon atoms.
  • Ring W 1 is preferably a single ring.
  • Ring W 1 is preferably a ring of an aliphatic hydrocarbon (alicyclic hydrocarbon group).
  • the ring W 1 has, for example, the following ring structure.
  • Ring W 1 has at least one substituent, which is present between two double bonds attached to ring W 1. That is, the compound of the present invention is preferably a compound containing an anion having a partial structure represented by the formula (X-1). [In formula (X-1), ring W 1 represents the same meaning as above, and R 3 represents a monovalent substituent. ]
  • R 3 is not particularly limited as long as it is a monovalent substituent, but for example, a monovalent aliphatic hydrocarbon group, a monovalent aromatic hydrocarbon group, an electron attracting group, an electron donating group, and a heterocyclic group. And so on.
  • the monovalent aliphatic hydrocarbon group represented by R 3 includes a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a tert-butyl group, a sec-butyl group and an n-pentyl group.
  • the monovalent aromatic hydrocarbon group represented by R 3 includes a phenyl group, a naphthyl group, an anthrasenyl group, a tetrasenyl group, a pentasenyl group, a phenanthryl group, a chrysenyl group, a triphenylenyl group, a tetraphenyl group, a pyrenyl group and a perylenyl group.
  • Aryl groups having 6 to 18 carbon atoms such as coronenyl group and biphenyl group; aralkyl groups having 7 to 18 carbon atoms such as benzyl group, phenylethyl group and naphthylmethyl group; phenoxyethyl group, phenoxydiethylene glycol group and phenoxypolyalkylene glycol Examples thereof include an arylalkoxy group as a group, and an aryl group having 6 to 18 carbon atoms is preferable, and a phenyl group or a benzyl group is more preferable.
  • Examples of the electron donating group represented by R 3 include a hydroxyl group; a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, a hexyloxy group, a heptyloxy group, an octyloxy group, and the like having 1 to 12 carbon atoms.
  • Examples of the heterocyclic group represented by R 3 include a pyrrolidine ring group, a pyrrolidine ring group, an imidazolidine ring group, an imidazoline ring group, an oxazoline ring group, a thiazoline ring group, a piperazine ring group, a morpholine ring group, a piperazine ring group, and an indole.
  • An aliphatic heterocyclic group having 4 to 20 carbon atoms or an aromatic heterocyclic group having 3 to 20 carbon atoms such as a ring group, an isoindole ring group, a quinoline ring group, a thiophene ring group, a pyrrol ring group, a thiazolin ring group and a furan ring group. Ring groups and the like can be mentioned.
  • Examples of the electron-attracting group represented by R 3 include a halogen atom, a nitro group, a cyano group, a carboxy group, an alkyl halide group, an aryl halide group, -OCF 3 , -SCF 3 , -SF 5 , and so on. Examples thereof include -SF 3 , -SO 3 H, -SO 2 H, and groups represented by the formula (z-1). [In formula (z-1), R222 represents a hydrogen atom, a halogen atom, or a hydrocarbon group which may have a substituent.
  • X 1 is -CO-, -COO-, -OCO-, -CS-, -CSS-, -COS-, -CSO-, -SO-, -SO 2- , -NR 223 CO- or -CONR 224.
  • R223 and R224 independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a phenyl group. * Represents a bond. ]
  • halogen atom examples include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
  • the alkyl halide groups include trifluoromethyl group, perfluoroethyl group, perfluoropropyl group, perfluoroisopropyl group, perfluorobutyl group, perfluorosec-butyl group, perfluorotert-butyl group, perfluoropentyl group, perfluorohexyl group and dichloromethyl group.
  • alkyl halide group having 1 to 25 carbon atoms such as a group, a bromomethyl group and an iodomethyl group.
  • an alkyl halide group having 1 to 12 carbon atoms is preferably an alkyl halide group having 1 to 12 carbon atoms, more preferably a fluoroalkyl group having 1 to 12 carbon atoms, and further preferably a perfluoroalkyl group having 1 to 12 carbon atoms.
  • the aryl halide group include an aryl halide group having 6 to 18 carbon atoms such as a fluorophenyl group, a chlorophenyl group and a bromophenyl group, and a fluoroaryl group having 6 to 18 carbon atoms is preferable. It is more preferably a perfluoroaryl group of 6-12, and even more preferably a pentafluorophenyl group.
  • X 1 is preferably -CO-, -COO- or -SO 2-.
  • the halogen atom represented by R 222 a fluorine atom, a chlorine atom, a bromine atom, an iodine atom.
  • Examples of the aliphatic hydrocarbon group having 1 to 25 carbon atoms include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a tert-butyl group, a sec-butyl group, an n-pentyl group and an n-.
  • Linear, branched, cyclic alkyl having 1 to 25 carbon atoms such as hexyl group, 1-methylbutyl group, 3-methylbutyl group, n-octyl group, n-decyl, 2-hexyl-octyl group and cyclohexyl group.
  • the group is mentioned, and it is preferably an alkyl having 1 to 12 carbon atoms.
  • the aromatic hydrocarbon group having 6 to 18 carbon atoms include an aryl group having 6 to 18 carbon atoms such as a phenyl group, a naphthyl group, an anthracenyl group and a biphenyl group; and a benzyl group, a phenylethyl group and a naphthylmethyl group. Examples thereof include 7 to 18 aralkyl groups.
  • the substituent which may be a hydrocarbon group having represented by R 222, halogen atom, hydroxy group, and the like.
  • Alkyl groups having 1 to 6 carbon atoms represented by R223 and R224 include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, tert-butyl group, sec-butyl group and n. Examples thereof include linear or branched alkyl having 1 to 6 carbon atoms such as a pentyl group, an n-hexyl group and a 1-methylbutyl group.
  • the groups represented by the formula (z-1) are -CO-R 1 , -CO- OR 2 , -CO-NR 3 R 3k , -CO-SR 4 , -CS-R 5 ,- CS- OR 6 , -CS-SR 7 , -SO-R 8 , -SO 2- R 9 (R 1 , R 2 , R 3 , R 3k , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 each represent a hydrocarbon group or a halogen atom which may have a substituent independently).
  • -CO-R 1, -CO-O -R 2, more preferably -SO 2 -R 9, -SO 2- R 9 is even more preferred.
  • -SO 2 -R 10 (R 10 is an aromatic hydrocarbon group having to 18 6 carbon atoms which may have a substituent), - SO 2 CF 3, -SO 2 CHF 2, -SO 2 CH 2 It is even more preferably F.
  • R 3 is preferably an electron-attracting group, preferably Cyan group, nitro group, alkyl halide group, aryl halide group, -SF 5 , -SF 3 , -SO 3 H, -SO 2 H, -CO-R 1 , -CO-O-R 2 , -CO -NR 3 R 3k , -CO-S-R 4 , -CS-R 5 , -CS- OR 6 , -CS-SR 7 , -SO-R 8 , -SO 2-
  • R 9 (R) 1 represents R 2, R 3, R 3k , R 4, R 5, R 6, R 7, R 8 and R 9 each independently may be substituted hydrocarbon group or a halogen atom ), -OCF 3 or -SCF 3 is more preferred.
  • Ring W 1 may have a substituent other than the substituent represented by R 3.
  • substituents include halogen atoms such as fluorine atom, chlorine atom, bromine atom and iodine atom; carbon such as methyl, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group and nonyl group.
  • An aliphatic hydrocarbon group having a number of 1 to 25 (preferably an alkyl group having 1 to 12 carbon atoms); a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a 2-fluoroethyl group, a 2,2-difluoroethyl group, Alkyl halide groups having 1 to 12 carbon atoms such as 2,2,2-trifluoroethyl group, 1,1,2,2-tetrafluoroethyl group, 1,1,2,2,2-pentafluoroethyl group
  • An alkoxy group having 1 to 12 carbon atoms such as a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, a hexyloxy group; a methylthio group, an ethylthio group, a propylthio group, a butylthio group, a pentylthio group
  • Alkylthio group having 1 to 12 carbon atoms monofluoromethoxy group, difluoromethoxy group, trifluoromethoxy group, 2-fluoroethoxy group, 1,1,2,2,2-pentafluoroethoxy group and the like having 1 to 12 carbon atoms.
  • Amino group which may be substituted with one alkyl group having 1 to 6 carbon atoms; N-position such as carbamoyl group, N-methylcarbamoyl group, N, N-dimethylcarbamoyl group is substituted with alkyl having 1 to 6 carbon atoms.
  • Carbamoyl group which may be used; alkylcarbonyloxy group having 2 to 12 carbon atoms such as methylcarbonyloxy group and ethylcarbonyloxy group; alkylsulfonyl group having 1 to 12 carbon atoms such as methylsulfonyl group and ethylsulfonyl group; phenyl Aromatic hydrocarbon groups having 6 to 25 carbon atoms (preferably aryl groups having 6 to 18 hydrocarbons) such as groups, naphthyl groups and diphenyl groups; arylsulfonyl groups having 6 to 12 carbon atoms such as phenylsulfonyl groups; methoxysulfonyl groups.
  • An alkoxysulfonyl group having 1 to 12 carbon atoms such as a group and an ethoxysulfonyl group; an acyl group having 2 to 12 carbon atoms such as an acetyl group and an ethylcarbonyl group; an aldehyde group; a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group and a butyl
  • An alkoxycarbonyl group having 2 to 12 carbon atoms such as an oxycarbonyl group; methoxythiocarbonyl Like -SF 5 or the like; a cyano group; a nitro group, a hydroxyl group, a thiol group, a sulfo group, a carbamoyl group, a carboxyl group, -SF 3 group, alkoxythiocarbonyl group having 2 to 12 carbon atoms such as ethoxycarbonyl thiocarbonyl group ..
  • the anion having a partial structure represented by the formula (X-1) may be an anion represented by the formula (I) to an anion represented by the formula (IV) or an anion represented by the formula (VIII). preferable.
  • rings W 1 and R 3 have the same meanings as described above, respectively.
  • Ring W 2 , ring W 3 , ring W 4 , ring W 5 , ring W 6 , ring W 7 and ring W 14 each independently represent a ring structure, which ring structure has a substituent. May be good.
  • R 13 , R 23 , R 33 , R 43 , R 53 , R 63 and R 133 represent monovalent substituents.
  • R 1 and R 2 may be connected to each other to form a ring.
  • R 2 and R 3 may be connected to each other to form a ring.
  • R 3 and R 4 may be connected to each other to form a ring.
  • R 4 and R 5 may be connected to each other to form a ring.
  • R 12 and R 13 may be connected to each other to form a ring.
  • R 13 and R 14 may be connected to each other to form a ring.
  • R 14 and R 15 may be connected to each other to form a ring.
  • R 22 and R 23 may be connected to each other to form a ring.
  • R 23 and R 24 may be connected to each other to form a ring.
  • R 24 and R 25 may be connected to each other to form a ring.
  • R 32 and R 33 may be connected to each other to form a ring.
  • R 33 and R 34 may be connected to each other to form a ring.
  • R 34 and R 35 may be connected to each other to form a ring.
  • R 42 and R 43 may be connected to each other to form a ring.
  • R 43 and R 44 may be connected to each other to form a ring.
  • R 44 and R 45 may be connected to each other to form a ring.
  • R 52 and R 53 may be connected to each other to form a ring.
  • R 53 and R 54 may be connected to each other to form a ring.
  • R 54 and R 55 may be connected to each other to form a ring.
  • R 62 and R 63 may be connected to each other to form a ring.
  • R 63 and R 64 may be connected to each other to form a ring.
  • R 64 and R 65 may be connected to each other to form a ring.
  • R 131 and R 132 may be connected to each other to form a ring.
  • R 132 and R 133 may be connected to each other to form a ring.
  • R 133 and R 134 may be connected to each other to form a ring.
  • R 134 and R 135 may be connected to each other to form a ring.
  • R x1 and R x7 each independently represent a single bond or a divalent linking group.
  • R x2 represents a trivalent linking group.
  • R x3 represents a tetravalent linking group.
  • the ring structure in the ring W 2 , the ring W 3 , the ring W 4 , the ring W 5 , the ring W 6 , the ring W 7, and the ring W 14 is not particularly limited.
  • Each ring W 2 ⁇ ring W 7 and ring 14 may be a single ring may be a condensed ring.
  • Rings W 2 to W 7 and 14 may be heterocycles containing a hetero atom (for example, an oxygen atom, a sulfur atom, a nitrogen atom, etc.) as a component of the ring.
  • Ring W 2 ⁇ ring W 7 and ring 14 is typically a ring having 5 to 18 carbon atoms, preferably 5 to 7-membered ring structure, more preferably a 6-membered ring structure.
  • the rings W 2 to W 7 and the ring 14 preferably have a ring structure having 5 to 7 carbon atoms, and more preferably a ring structure having 6 carbon atoms.
  • Ring W 2 ⁇ ring W 7 and ring 14 are each independently preferably a single ring.
  • Ring W 2 ⁇ ring W 7 and ring 14 may have a substituent, specifically, a substituent which may be ring W 1 optionally has other than the substituent represented by R 3 The same can be mentioned.
  • Substituents wherein the ring W 2 ⁇ ring W 7 and the ring 14 has an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an alkylthio group or an alkyl having 1 to 6 carbon atoms having 1 to 12 carbon atoms It is preferably an amino group that may be substituted with a group.
  • rings W 2 to W 7 and the ring 14 include the same as the specific examples of the ring W 1 .
  • the monovalent substituent represented by R 13 , R 23 , R 33 , R 43 , R 53 , R 63 and R 133 is not particularly limited and is the same as the monovalent substituent represented by R 3. Can be mentioned. Specific examples thereof include a monovalent aliphatic hydrocarbon group, a monovalent aromatic hydrocarbon group, an electron attracting group, an electron donating group, and a heterocyclic group. It is preferable that R 13 , R 23 , R 33 , R 43 , R 53 , R 63 and R 133 are independently electron-attracting groups, respectively.
  • R 1 and R 2 may be combined with each other to form a ring.
  • the ring formed by bonding R 1 and R 2 to each other may be a monocyclic ring or a condensed ring, but is preferably a monocyclic ring.
  • the ring formed by bonding R 1 and R 2 to each other may contain a hetero atom (nitrogen atom, oxygen atom, sulfur atom) or the like as a component of the ring.
  • the ring formed by bonding R 1 and R 2 to each other is usually a 3- to 10-membered ring, preferably a 5- to 7-membered ring, and more preferably a 5-membered ring or a 6-membered ring.
  • Examples of the ring formed by bonding R 1 and R 2 to each other include the ring structure described below. [In the formula, * represents a bond. ]
  • the rings formed by combining R 1 and R 2 with each other are represented by formulas (w-1) to (w-15), formulas (w-17), formulas (w-31), and formulas (w-32).
  • Formulations (w-35) to formulas (w-42) and preferably ring structures represented by formulas (w-44), formulas (w-1) to formulas (w-6), formulas (w). -13), the ring structure represented by the formula (w-35), the formula (w-36), the formula (w-42) and the formula (w-44) is more preferable.
  • Examples of the ring formed by connecting R 4 and R 5 to each other include the same ring formed by connecting R 1 and R 2 to each other.
  • Ring R 4 and R 5 are formed by linking each other, the formula (w-1) ⁇ formula (w-15), formula (w-17), formula (w-31), formula (w-32) , Formulations (w-35) to formulas (w-42) and preferably ring structures represented by formulas (w-44), formulas (w-1) to formulas (w-6), formulas (w). -13), the ring structure represented by the formula (w-35), the formula (w-36), the formula (w-42) and the formula (w-44) is more preferable.
  • Examples of the ring formed by connecting R 14 and R 15 to each other include the same ring formed by connecting R 1 and R 2 to each other.
  • the rings formed by connecting R 14 and R 15 to each other are represented by formulas (w-1) to (w-15), formulas (w-17), formulas (w-31), and formulas (w-32).
  • Formulations (w-35) to formulas (w-42) and preferably ring structures represented by formulas (w-44), formulas (w-1) to formulas (w-6), formulas (w). -13), the ring structure represented by the formula (w-35), the formula (w-36), the formula (w-42) and the formula (w-44) is more preferable.
  • Examples of the ring formed by connecting R 24 and R 25 to each other include the same ring formed by connecting R 1 and R 2 to each other.
  • the rings formed by connecting R 24 and R 25 to each other are represented by formulas (w-1) to (w-15), formulas (w-17), formulas (w-31), and formulas (w-32).
  • Formulations (w-35) to formulas (w-42) and preferably ring structures represented by formulas (w-44), formulas (w-1) to formulas (w-6), formulas (w). -13), the ring structure represented by the formula (w-35), the formula (w-36), the formula (w-42) and the formula (w-44) is more preferable.
  • Examples of the ring formed by connecting R 34 and R 35 to each other include the same ring formed by connecting R 1 and R 2 to each other.
  • the rings formed by connecting R 34 and R 35 to each other are represented by formulas (w-1) to (w-15), formulas (w-17), formulas (w-31), and formulas (w-32).
  • Formulations (w-35) to formulas (w-42) and preferably ring structures represented by formulas (w-44), formulas (w-1) to formulas (w-6), formulas (w). -13), the ring structure represented by the formula (w-35), the formula (w-36), the formula (w-42) and the formula (w-44) is more preferable.
  • Examples of the ring formed by connecting R 44 and R 45 to each other include the same ring formed by connecting R 1 and R 2 to each other.
  • the rings formed by connecting R 44 and R 45 to each other are represented by formulas (w-1) to (w-15), formulas (w-17), formulas (w-31), and formulas (w-32).
  • Formulations (w-35) to formulas (w-42) and preferably ring structures represented by formulas (w-44), formulas (w-1) to formulas (w-6), formulas (w). -13), the ring structure represented by the formula (w-35), the formula (w-36), the formula (w-42) and the formula (w-44) is more preferable.
  • Examples of the ring formed by connecting R 54 and R 55 to each other include the same ring formed by connecting R 1 and R 2 to each other.
  • the rings formed by connecting R 54 and R 55 to each other are represented by formulas (w-1) to (w-15), formulas (w-17), formulas (w-31), and formulas (w-32).
  • Formulations (w-35) to formulas (w-42) and preferably ring structures represented by formulas (w-44), formulas (w-1) to formulas (w-6), formulas (w). -13), the ring structure represented by the formula (w-35), the formula (w-36), the formula (w-42) and the formula (w-44) is more preferable.
  • Examples of the ring formed by connecting R 64 and R 65 to each other include the same ring formed by connecting R 1 and R 2 to each other.
  • the rings formed by connecting R 64 and R 65 to each other are represented by formulas (w-1) to (w-15), formulas (w-17), formulas (w-31), and formulas (w-32).
  • Formulations (w-35) to formulas (w-42) and preferably ring structures represented by formulas (w-44), formulas (w-1) to formulas (w-6), formulas (w). -13), the ring structure represented by the formula (w-35), the formula (w-36), the formula (w-42) and the formula (w-44) is more preferable.
  • Examples of the ring formed by connecting R 131 and R 132 to each other include the same ring formed by connecting R 1 and R 2 to each other.
  • the rings formed by connecting R 131 and R 132 to each other are represented by formulas (w-1) to (w-15), formulas (w-17), formulas (w-31), and formulas (w-32).
  • Formulations (w-35) to formulas (w-42) and preferably ring structures represented by formulas (w-44), formulas (w-1) to formulas (w-6), formulas (w). -13), the ring structure represented by the formula (w-35), the formula (w-36), the formula (w-42) and the formula (w-44) is more preferable.
  • Examples of the ring formed by connecting R 134 and R 135 to each other include the same ring formed by connecting R 1 and R 2 to each other.
  • the rings formed by connecting R 134 and R 135 to each other are represented by formulas (w-1) to (w-15), formulas (w-17), formulas (w-31), and formulas (w-32).
  • Formulations (w-35) to formulas (w-42) and preferably ring structures represented by formulas (w-44), formulas (w-1) to formulas (w-6), formulas (w). -13), the ring structure represented by the formula (w-35), the formula (w-36), the formula (w-42) and the formula (w-44) is more preferable.
  • R 2 and R 3 may be connected to each other to form a ring.
  • the ring formed by connecting R 2 and R 3 includes a double bond bonded to ring W 1 as a component of the ring.
  • a fused ring is formed by a ring formed by connecting R 2 and R 3 and a ring W 1. Examples of the fused ring formed by the ring formed by bonding R 2 and R 3 to each other and the ring W 1 are represented by the following formulas (w11-1) to (w11-12).
  • the ring structure to be formed is mentioned. [In the equation, ring W 1 has the same meaning as above. * 1 represents a bond with R 1 , * 2 represents a bond with R 4, and * 3 represents a bond with R 5 .
  • R f1 , R f2, and R f3 independently represent an electron-attracting group, a hydrocarbon group, and a hydroxyl group, respectively.
  • m1 represents an integer of 0 to 6
  • m2 represents an integer of 0 to 4
  • m3 represents an integer of 0 to 2.
  • fused ring formed by the ring formed by bonding R 2 and R 3 to each other and the ring W 1 include the ring structure described below.
  • R 12 and R 13 may be connected to each other to form a ring.
  • the ring formed by connecting R 12 and R 13 includes a double bond bonded to ring W 2 as a component of the ring.
  • a fused ring is formed by a ring formed by connecting R 12 and R 13 and a ring W 2. Specifically, the same ring as the fused ring formed by the ring W 1 formed by bonding R 2 and R 3 to each other can be mentioned.
  • R 22 and R 23 may be connected to each other to form a ring.
  • the ring formed by connecting R 22 and R 23 includes a double bond bonded to ring W 3 as a component of the ring.
  • a fused ring is formed by a ring formed by connecting R 22 and R 23 and a ring W 3. Specifically, the same ring as the fused ring formed by the ring W 1 formed by bonding R 2 and R 3 to each other can be mentioned.
  • R 32 and R 33 may be connected to each other to form a ring.
  • the ring formed by connecting R 32 and R 33 includes a double bond bonded to ring W 4 as a component of the ring.
  • a fused ring is formed by a ring formed by connecting R 32 and R 33 and a ring W 4. Specifically, the same ring as the fused ring formed by the ring W 1 formed by bonding R 2 and R 3 to each other can be mentioned.
  • R 42 and R 43 may be connected to each other to form a ring.
  • the ring formed by connecting R 42 and R 43 includes a double bond bonded to ring W 5 as a component of the ring.
  • a fused ring is formed by a ring formed by connecting R 42 and R 43 and a ring W 5. Specifically, the same ring as the fused ring formed by the ring W 1 formed by bonding R 2 and R 3 to each other can be mentioned.
  • R 52 and R 53 may be connected to each other to form a ring.
  • the ring formed by connecting R 52 and R 53 includes a double bond bonded to ring W 6 as a component of the ring.
  • a fused ring is formed by a ring formed by connecting R 52 and R 53 and a ring W 6. Specifically, the same ring as the fused ring formed by the ring W 1 formed by bonding R 2 and R 3 to each other can be mentioned.
  • R 62 and R 63 may be connected to each other to form a ring.
  • the ring formed by connecting R 62 and R 63 includes a double bond bonded to ring W 7 as a component of the ring.
  • a fused ring is formed by a ring formed by connecting R 62 and R 63 and a ring W 7. Specifically, the same ring as the fused ring formed by the ring W 1 formed by bonding R 2 and R 3 to each other can be mentioned.
  • R 132 and R 133 may be connected to each other to form a ring.
  • the ring formed by connecting R 132 and R 133 includes a double bond bonded to ring W 14 as a component of the ring.
  • a fused ring is formed by a ring formed by connecting R 132 and R 133 and a ring W 14. Specifically, the same ring as the fused ring formed by the ring W 1 formed by bonding R 2 and R 3 to each other can be mentioned.
  • R 3 and R 4 may be connected to each other to form a ring.
  • the ring formed by connecting R 3 and R 4 includes a double bond bonded to ring W 1 as a component of the ring.
  • a fused ring is formed by a ring formed by connecting R 3 and R 4 and a ring W 1.
  • Specific examples of the fused ring formed by the ring W 1 formed by the ring formed by bonding R 3 and R 4 to each other include the rings described below. [In the equation, ring W 1 has the same meaning as above. * 4 represents a bond with R 1 , * 5 represents a bond with R 2, and * 6 represents a bond with R 5 .
  • R f4 , R f5 and R f6 independently represent an electron-attracting group, a hydrocarbon group and a hydroxyl group, respectively.
  • m4 represents an integer of 0 to 6
  • m5 represents an integer of 0 to 4
  • m6 represents an integer of 0 to 2.
  • fused ring formed by the ring formed by bonding R 3 and R 4 to each other and the ring W 1 include the ring structure described below.
  • R 13 and R 14 may be connected to each other to form a ring.
  • the ring formed by connecting R 13 and R 14 includes a double bond bonded to ring W 2 as a component of the ring.
  • a fused ring is formed by a ring formed by connecting R 13 and R 14 and a ring W 2. Specifically, the same as the fused ring formed by the ring formed by bonding R 3 and R 4 to each other and the ring W 1 can be mentioned.
  • R 23 and R 24 may be connected to each other to form a ring.
  • the ring formed by connecting R 23 and R 24 includes a double bond bonded to ring W 3 as a component of the ring.
  • a fused ring is formed by a ring formed by connecting R 23 and R 24 and a ring W 3. Specifically, the same as the fused ring formed by the ring formed by bonding R 3 and R 4 to each other and the ring W 1 can be mentioned.
  • R 33 and R 34 may be connected to each other to form a ring.
  • the ring formed by connecting R 33 and R 34 includes a double bond bonded to ring W 4 as a component of the ring.
  • a fused ring is formed by a ring formed by connecting R 33 and R 34 and a ring W 4. Specifically, the same as the fused ring formed by the ring formed by bonding R 3 and R 4 to each other and the ring W 1 can be mentioned.
  • R 43 and R 44 may be connected to each other to form a ring.
  • the ring formed by connecting R 43 and R 44 includes a double bond bonded to ring W 5 as a component of the ring.
  • a fused ring is formed by a ring formed by connecting R 43 and R 44 and a ring W 5. Specifically, the same as the fused ring formed by the ring formed by bonding R 3 and R 4 to each other and the ring W 1 can be mentioned.
  • R 53 and R 54 may be connected to each other to form a ring.
  • the ring formed by connecting R 53 and R 54 includes a double bond bonded to ring W 6 as a component of the ring.
  • a fused ring is formed by a ring formed by connecting R 53 and R 54 and a ring W 6. Specifically, the same as the fused ring formed by the ring formed by bonding R 3 and R 4 to each other and the ring W 1 can be mentioned.
  • R 63 and R 64 may be connected to each other to form a ring.
  • the ring formed by connecting R 63 and R 64 includes a double bond bonded to ring W 7 as a component of the ring.
  • a fused ring is formed by a ring formed by connecting R 63 and R 64 and a ring W 7. Specifically, the same as the fused ring formed by the ring formed by bonding R 3 and R 4 to each other and the ring W 1 can be mentioned.
  • R 133 and R 134 may be connected to each other to form a ring.
  • the ring formed by connecting R 133 and R 134 includes a double bond bonded to ring W 14 as a component of the ring.
  • a fused ring is formed by a ring formed by connecting R 133 and R 134 and a ring W 14. Specifically, the same as the fused ring formed by the ring formed by bonding R 3 and R 4 to each other and the ring W 1 can be mentioned.
  • each independently has a divalent aliphatic hydrocarbon group having 1 to 18 carbon atoms or a substituent which may have a substituent.
  • examples thereof include a divalent aromatic hydrocarbon group having 6 to 18 carbon atoms which may be used.
  • -CH 2- contained in the divalent aliphatic hydrocarbon group and the divalent aromatic hydrocarbon group is -O-, -S-, -NR 1B- (R 1B is a hydrogen atom or 1 to 1 to carbon atoms. (Representing an alkyl group of 6), -CO-, -SO 2- , -SO-, -PO 3- may be substituted.
  • Examples of the substituent that the divalent aliphatic hydrocarbon group may have include a halogen atom, a hydroxyl group, a carboxy group, an amino group, and an aryl group having 6 to 16 carbon atoms.
  • Examples of the substituent that the divalent aromatic hydrocarbon group may have include a halogen atom, a hydroxyl group, a carboxy group, an amino group, an aldehyde group and the like.
  • R x1 and R x7 include the linking groups described below.
  • * represents a bond.
  • the divalent linking groups represented by R x1 and R x7 each independently have a divalent aliphatic hydrocarbon group having 1 to 12 carbon atoms and a substituent which may have a substituent. preferably also a divalent aromatic hydrocarbon group which may having 6 to 12 carbon atoms optionally (-CH 2 contained in the aromatic hydrocarbon group having a bivalent aliphatic hydrocarbon group and the divalent said - is, -O -, - S -, - NR 1B -, - CO -, - SO 2 - is preferred that substituted also be) in, and more preferably a linking group as described below.
  • Examples include ⁇ 18 trivalent aromatic hydrocarbon groups.
  • -CH 2- contained in the trivalent aliphatic hydrocarbon group and the trivalent aromatic hydrocarbon group is -O-, -S-, -CS-, -CO-, -SO-, -SO. It may be replaced with 2-, -NR 11B- (R 11B represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms).
  • the trivalent linking group represented by R x2 is a trivalent aliphatic hydrocarbon group having 1 to 18 carbon atoms (-CH 2- contained in the trivalent aliphatic hydrocarbon group is -O-, -CO-, -SO 2- may be replaced) and a trivalent aromatic hydrocarbon group having 6 to 18 carbon atoms (-CH 2- contained in the trivalent aromatic hydrocarbon group-is. -O -, - CO -, - SO 2 -. which may be replaced by) is preferably.
  • Specific examples of the trivalent linking group represented by R x2 include the linking groups described below.
  • Examples include to 18 tetravalent aromatic hydrocarbon groups.
  • -CH 2- contained in the tetravalent aliphatic hydrocarbon group and the tetravalent aromatic hydrocarbon group is -O-, -S-, -CS-, -CO-, -SO-, -SO. It may be replaced with 2-, -NR 11C- (R 11C represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms).
  • the substituent that the tetravalent aliphatic hydrocarbon group and the tetravalent aromatic hydrocarbon group may have include a halogen atom, a hydroxyl group, a carboxy group, an amino group and the like.
  • the tetravalent linking group represented by R x3 is a tetravalent aliphatic hydrocarbon group having 1 to 18 carbon atoms (-CH 2- contained in the tetravalent aliphatic hydrocarbon group is -O-, -CO-, -SO 2- may be replaced) and a tetravalent aliphatic hydrocarbon group having 6 to 18 carbon atoms (-CH 2- contained in the tetravalent aromatic hydrocarbon group-is. -O -, - CO -, - SO 2 -. which may be replaced by) is preferably.
  • Specific examples of the tetravalent linking group represented by R x3 include the linking groups described below.
  • the anion represented by the formula (I) is more preferably an anion represented by the formula (IA).
  • R 1 , R 2 , R 3 , R 4 and R 5 have the same meanings as described above.
  • R E1 , R E2 , R E3 , R E4 , R E5 and R E6 each independently represent a hydrogen atom, a hydrocarbon group having 1 to 25 carbon atoms or an alkoxy group.
  • at least one selected from R 1 , R 2 , R 3 , R 4 and R 5 is a cyano group, a nitro group, an alkyl halide group, an aryl halide group, -SCF 3 ,-.
  • it is a cyano group, a nitro group, -CO-R 1 , -CO- OR 2 , -SO 2- R 9 , -OCF 3 , -SCF 3 or -SF 5.
  • a cyano group, a nitro group, -OCF 3, -SCF 3, -SF 5, -SO 2 CF 3, -SO 2 -R 10 (R 10 is a substituted group the unprotected 6 to 18 carbon atoms also have Aromatic hydrocarbon groups) are even more preferred, More preferably, it is a cyano group or a nitro group.
  • anion represented by the formula (I) examples include the anions described below.
  • anion represented by the formula (II) examples include the anions described below.
  • anion represented by the formula (III) examples include the anions described below.
  • anion represented by the formula (IV) examples include the anions described below.
  • anion represented by the formula (VIII) examples include the anions described below.
  • the anion having the partial structure represented by the formula (X) is, for example, an anion represented by the formula (V) to the formula (VII). Examples thereof include anions represented by.
  • rings W 1 , R 1 , R 2 , R 4 and R 5 have the same meanings as described above, respectively.
  • Ring W 8 , ring W 9 , ring W 10 , ring W 11 , ring W 12 and ring W 13 each independently represent a ring structure, and the ring structure may have a substituent.
  • R 71 and R 72 may be connected to each other to form a ring.
  • R 74 and R 75 may be connected to each other to form a ring.
  • R 81 and R 82 may be connected to each other to form a ring.
  • R 84 and R 85 may be connected to each other to form a ring.
  • R 91 and R 92 may be connected to each other to form a ring.
  • R 94 and R 95 may be connected to each other to form a ring.
  • R 101 and R 102 may be connected to each other to form a ring.
  • R 104 and R 105 may be connected to each other to form a ring.
  • R 111 and R 112 may be connected to each other to form a ring.
  • R 114 and R 115 may be connected to each other to form a ring.
  • R 121 and R 122 may be connected to each other to form a ring.
  • R 124 and R 125 may be connected to each other to form a ring.
  • R x4 represents a single bond or a divalent linking group.
  • R x5 represents a trivalent linking group.
  • R x6 represents a tetravalent linking group.
  • Rings W 9 to W 12 may be monocyclic or condensed rings, respectively. Rings W 9 to W 12 may be heterocycles containing a hetero atom (for example, an oxygen atom, a sulfur atom, a nitrogen atom, etc.) as a component of the ring. Rings W 9 to W 12 are usually rings having 5 to 18 carbon atoms, preferably having a 5- to 7-membered ring structure, and more preferably a 6-membered ring structure.
  • Rings W 9 to W 12 preferably have a ring structure having 5 to 7 carbon atoms, and more preferably a ring structure having 6 carbon atoms. It is preferable that the rings W 9 to W 12 are independent and monocyclic. Rings W 9 to W 12 may have a substituent, and specifically, the same substituents that the ring W 1 may have other than the substituent represented by R 3 are used. Can be mentioned.
  • the substituents of rings W 9 to W 12 are substituted with an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an alkylthio group having 1 to 12 carbon atoms or an alkyl group having 1 to 6 carbon atoms. It is preferably an amino group which may be used.
  • Specific examples of the rings W 9 to 12 include the same as the specific examples of the ring W 1 .
  • Examples of the electron attracting group are the same as those represented by R 3. ..
  • R 9 R 1 , R 2 , R 3 , R 3k , R 4 , R 5 , R 6 , R 7) , R 8 and R 9 each independently represents which may have a substituent a hydrocarbon group or a halogen atom), -.
  • a OCF 3 or -SCF 3 A cyano group, a nitro group, -OCF 3, -SCF 3, -SF 5, -SF 3, -SO 3 H, -SO 2 H, -CO-R 1, -CO-O-R 2, -SO 2 - more preferably R 9, More preferably, it is a cyano group, a nitro group, -CO-R 1 , -CO- OR 2 , -SO 2- R 9 , -OCF 3 , -SCF 3 or -SF 5.
  • a cyano group, a nitro group, -OCF 3, -SCF 3, -SF 5, -SO 2 CF 3, -SO 2 -R 10 (R 10 is a substituted group the unprotected 6 to 18 carbon atoms also have Aromatic hydrocarbon groups) are even more preferred, More preferably, it is a cyano group or a nitro group.
  • R 71 and R 72 may be combined with each other to form a ring.
  • the ring formed by bonding R 71 and R 72 to each other may be a monocyclic ring or a condensed ring, but is preferably a monocyclic ring.
  • the ring formed by bonding R 71 and R 72 to each other may contain a hetero atom (nitrogen atom, oxygen atom, sulfur atom) or the like as a component of the ring.
  • the ring formed by connecting R 71 and R 72 to each other is usually a 3- to 10-membered ring, preferably a 5- to 7-membered ring, and more preferably a 5-membered ring or a 6-membered ring.
  • Examples of the ring formed by connecting R 71 and R 72 to each other include the same ring formed by connecting R 1 and R 2 to each other.
  • the rings formed by connecting R 71 and R 72 to each other are represented by formulas (w-1) to (w-15), formulas (w-17), formulas (w-31), and formulas (w-32).
  • Formula (w-35) to formula (w-42) and formula (w-44) are preferable, and formulas (w-1) to formula (w-6), formula (w-). 13), the ring structure represented by the formula (w-35), the formula (w-36), the formula (w-42) and the formula (w-44) is more preferable.
  • Examples of the ring formed by connecting R 74 and R 75 to each other include the same ring formed by connecting R 71 and R 72 to each other.
  • the rings formed by connecting R 74 and R 75 to each other are represented by formulas (w-1) to (w-15), formulas (w-17), formulas (w-31), and formulas (w-32).
  • Formulations (w-35) to formulas (w-42) and preferably ring structures represented by formulas (w-44), formulas (w-1) to formulas (w-6), formulas (w). -13), the ring structure represented by the formula (w-35), the formula (w-36), the formula (w-42) and the formula (w-44) is more preferable.
  • Examples of the ring formed by connecting R 81 and R 82 to each other include the same ring formed by connecting R 71 and R 72 to each other.
  • the rings formed by connecting R 81 and R 82 to each other are represented by formulas (w-1) to (w-15), formulas (w-17), formulas (w-31), and formulas (w-32).
  • Formulations (w-35) to formulas (w-42) and preferably ring structures represented by formulas (w-44), formulas (w-1) to formulas (w-6), formulas (w). -13), the ring structure represented by the formula (w-35), the formula (w-36), the formula (w-42) and the formula (w-44) is more preferable.
  • Examples of the ring formed by connecting R 84 and R 85 to each other include the same ring formed by connecting R 71 and R 72 to each other.
  • the rings formed by combining R 84 and R 85 with each other are represented by formulas (w-1) to (w-15), formulas (w-17), formulas (w-31), and formulas (w-32).
  • Formulations (w-35) to formulas (w-42) and preferably ring structures represented by formulas (w-44), formulas (w-1) to formulas (w-6), formulas (w). -13), the ring structure represented by the formula (w-35), the formula (w-36), the formula (w-42) and the formula (w-44) is more preferable.
  • Examples of the ring formed by connecting R 91 and R 92 to each other include the same ring formed by connecting R 71 and R 72 to each other.
  • the rings formed by connecting R 91 and R 92 to each other are represented by formulas (w-1) to (w-15), formulas (w-17), formulas (w-31), and formulas (w-32).
  • Formulations (w-35) to formulas (w-42) and preferably ring structures represented by formulas (w-44), formulas (w-1) to formulas (w-6), formulas (w). -13), the ring structure represented by the formula (w-35), the formula (w-36), the formula (w-42) and the formula (w-44) is more preferable.
  • Examples of the ring formed by connecting R 94 and R 95 to each other include the same ring formed by connecting R 71 and R 72 to each other.
  • the rings formed by combining R 94 and R 95 with each other are represented by formulas (w-1) to (w-15), formulas (w-17), formulas (w-31), and formulas (w-32).
  • Formulations (w-35) to formulas (w-42) and preferably ring structures represented by formulas (w-44), formulas (w-1) to formulas (w-6), formulas (w). -13), the ring structure represented by the formula (w-35), the formula (w-36), the formula (w-42) and the formula (w-44) is more preferable.
  • Examples of the ring formed by connecting R 101 and R 102 to each other include the same ring formed by connecting R 71 and R 72 to each other.
  • the rings formed by connecting R 101 and R 102 to each other are represented by formulas (w-1) to (w-15), formulas (w-17), formulas (w-31), and formulas (w-32).
  • Formulations (w-35) to formulas (w-42) and preferably ring structures represented by formulas (w-44), formulas (w-1) to formulas (w-6), formulas (w). -13), the ring structure represented by the formula (w-35), the formula (w-36), the formula (w-42) and the formula (w-44) is more preferable.
  • Examples of the ring formed by connecting R 104 and R 105 to each other include the same ring formed by connecting R 71 and R 72 to each other.
  • the rings formed by connecting R 104 and R 105 to each other are represented by formulas (w-1) to (w-15), formulas (w-17), formulas (w-31), and formulas (w-32).
  • Formulations (w-35) to formulas (w-42) and preferably ring structures represented by formulas (w-44), formulas (w-1) to formulas (w-6), formulas (w). -13), the ring structure represented by the formula (w-35), the formula (w-36), the formula (w-42) and the formula (w-44) is more preferable.
  • Examples of the ring formed by connecting R 111 and R 112 to each other include the same ring formed by connecting R 71 and R 72 to each other.
  • the rings formed by connecting R 111 and R 112 to each other are represented by formulas (w-1) to (w-15), formulas (w-17), formulas (w-31), and formulas (w-32).
  • Formulations (w-35) to formulas (w-42) and preferably ring structures represented by formulas (w-44), formulas (w-1) to formulas (w-6), formulas (w). -13), the ring structure represented by the formula (w-35), the formula (w-36), the formula (w-42) and the formula (w-44) is more preferable.
  • Examples of the ring formed by connecting R 114 and R 115 to each other include the same ring formed by connecting R 71 and R 72 to each other.
  • the rings formed by connecting R 114 and R 115 to each other are represented by formulas (w-1) to (w-15), formulas (w-17), formulas (w-31), and formulas (w-32).
  • Formulations (w-35) to formulas (w-42) and preferably ring structures represented by formulas (w-44), formulas (w-1) to formulas (w-6), formulas (w). -13), the ring structure represented by the formula (w-35), the formula (w-36), the formula (w-42) and the formula (w-44) is more preferable.
  • Examples of the ring formed by connecting R 121 and R 122 to each other include the same ring formed by connecting R 71 and R 72 to each other.
  • the rings formed by connecting R 121 and R 122 to each other are represented by formulas (w-1) to (w-15), formulas (w-17), formulas (w-31), and formulas (w-32).
  • Formulations (w-35) to formulas (w-42) and preferably ring structures represented by formulas (w-44), formulas (w-1) to formulas (w-6), formulas (w). -13), the ring structure represented by the formula (w-35), the formula (w-36), the formula (w-42) and the formula (w-44) is more preferable.
  • Examples of the ring formed by connecting R 124 and R 125 to each other include the same ring formed by connecting R 71 and R 72 to each other.
  • the rings formed by the coupling of R 124 and R 125 to each other are represented by formulas (w-1) to (w-15), formulas (w-17), formulas (w-31), and formulas (w-32).
  • Formulations (w-35) to formulas (w-42) and preferably ring structures represented by formulas (w-44), formulas (w-1) to formulas (w-6), formulas (w). -13), the ring structure represented by the formula (w-35), the formula (w-36), the formula (w-42) and the formula (w-44) is more preferable.
  • Examples thereof include divalent aromatic hydrocarbon groups of ⁇ 18. -CH 2- contained in the divalent aliphatic hydrocarbon group and the divalent aromatic hydrocarbon group is -O-, -S-, -NR 1B- (R 1B is a hydrogen atom or 1 to 1 to carbon atoms. (Representing an alkyl group of 6), -CO-, -SO 2- , -SO-, -PO 3- may be substituted.
  • Examples of the substituent that the divalent aliphatic hydrocarbon group and the divalent aromatic hydrocarbon group may have include a halogen atom, a hydroxyl group, a carboxy group, an amino group and the like.
  • Specific examples of the divalent linking group represented by R x4 include the same specific examples of the divalent linking group represented by R x1.
  • a divalent linking group represented by R x4 preferably the linking group described below.
  • Examples include ⁇ 18 trivalent aromatic hydrocarbon groups.
  • -CH 2- contained in the trivalent aliphatic hydrocarbon group is -O-, -S-, -CS-, -CO-, -SO- , -NR 11B (R 11B is a hydrogen atom or the number of carbon atoms). It represents an alkyl group of 1 to 6)-may be replaced by.
  • the trivalent linking group represented by R x5 is preferably a trivalent aliphatic hydrocarbon group having 1 to 12 carbon atoms which may have a substituent.
  • Specific examples of the trivalent linking group represented by R x5 include the same specific examples of the trivalent linking group represented by R x2.
  • the linking group represented by R x5 is preferably the linking group described below.
  • a tetravalent linking group represented by R x6 a tetravalent aliphatic hydrocarbon group having 1 to 18 carbon atoms which may have a substituent or a substituent may have 6 carbon atoms.
  • Examples include to 18 tetravalent aromatic hydrocarbon groups.
  • -CH 2- contained in the tetravalent aliphatic hydrocarbon group is -O-, -S-, -CS-, -CO-, -SO- , -NR 11C- (R 11C is a hydrogen atom or carbon. It may be replaced by (representing an alkyl group of the number 1 to 6).
  • the substituent that the tetravalent aliphatic hydrocarbon group and the tetravalent aromatic hydrocarbon group may have include a halogen atom, a hydroxyl group, a carboxy group, an amino group and the like.
  • the tetravalent linking group represented by R x6 is preferably a tetravalent aliphatic hydrocarbon group having 1 to 12 carbon atoms, which may independently have a substituent.
  • Specific examples of the tetravalent linking group represented by R x6 include the same specific examples of the tetravalent linking group represented by R x3.
  • the tetravalent linking group represented by R x6 is preferably the linking group described below.
  • Examples of the anion represented by the formula (V) include the anions described below.
  • anion represented by the formula (VI) examples include the anions described below.
  • anion represented by the formula (VII) examples include the anions described below.
  • the compound of the present invention is composed of an anion represented by the formula (X) and a pair of cations.
  • the valence of the anion represented by the formula (X) and the valence of the cation are the same, the combination is not limited.
  • the cation may be a cation having the same valence as the anion represented by the formula (X), or is represented by the formula (X). It may have a plurality of monovalent cations so as to have the same valence as the valence of the anion.
  • the valence is the same as the valence of the anion represented by the formula (X), even if it has a monovalent cation and a cation other than the monovalent cation (for example, a divalent cation). good.
  • the cation has a valence of 2 or more, it may have a plurality of anions represented by the monovalent formula (X) so as to have the same valence as the cation.
  • it may have an anion represented by a monovalent formula (X) and an anion represented by a formula (X) other than monovalent. ..
  • the cation may be an organic cation or an inorganic cation. Further, when the valence of the anion represented by the formula (X) is 2 or more, the compound (X) may have an organic cation and an inorganic cation as cations.
  • organic cations include N-methylpyridinium, N-ethylpyridinium, N-propylpyridinium, N-ethyl-2-methylpyridinium, N-ethyl-3-methylpyridinium, 1-ethyl-3- (hydroxymethyl) pyridinium, N-butylpyridinium, N-butyl-4-methylpyridinium, N-butyl-3-methylpyridinium, N-hexylpyridinium, N-octylpyridinium, N-octyl-4-methylpyridinium, 1,1'-dimethyl-4 , 4'-bipyridinium, 1,1'-dibenzyl-4,4'-bipyridinium and other pyridinium cations; Piperidinium cations such as 1-butyl-1-methylpiperidinium and 1-methyl-1-propylpiperidinium; 1-allyl-1-methylpyrrolidinium, 1-butyl
  • Examples of the inorganic cation include alkali metal ions such as lithium ion, sodium ion, potassium ion, rubidium ion, and cesium ion; Monovalent metal ions such as copper (I) ion, silver ion, iron (I) ion; Alkaline earth metal ions such as beryllium ion, magnesium ion, calcium ion, strontium ion, barium ion; Divalent metal ions such as copper (II) ion, nickel ion, cobalt ion, iron (II) ion, manganese ion, palladium ion, zinc ion, germanium (IV) ion; Trivalent metal ions such as aluminum ion, cobalt (III) ion, iron (III) ion, chromium (III) ion, scandium ion, yttrium ion, ruthenium (III) ion, gallium ion, and
  • the cations are alkali metal ion, alkaline earth metal ion, copper (I) ion, copper (II) ion, nickel ion, cobalt (III) ion, iron (II) ion, iron (III) ion, palladium ion and organic. It is preferably a cation, more preferably a potassium ion, a calcium ion, a barium ion, a magnesium ion, a copper (I) ion, a copper (II) ion, a nickel ion and an organic cation, and even more preferably a potassium ion and an organic. It is a cation.
  • Examples of the compound (X) include the compounds listed in Tables 1 to 9 below.
  • the compound (1) is a compound shown below.
  • Examples of the compound (X) having an anion represented by the formula (I) include compounds (1) to (63), and compounds (2) and compounds ( 3), Compound (7) to Compound (11), Compound (13) to Compound (18), Compound (24), Compound (28), Compound (31), Compound (32), Compound (37), Compound ( 40) to compound (44), compound (46), compound (47), compound (49), compound (50), compound (55), compound (58), compound (60) are preferable.
  • Examples of the compound (X) having an anion represented by the formula (II) include compound (64) to compound (92), and the compound (64) and the compound ( 65), compound (67), compound (70), compound (72), compound (75) to compound (77), compound (79), compound (80), compound (83), compound (84), compound ( 86), preferably compound (87).
  • Examples of the compound (X) having an anion represented by the formula (III) include compound (93) to compound (118), and compound (93) and compound ( 94), compound (96), compound (101) to compound (105), compound (107), compound (109), compound (111), compound (115), compound (116).
  • Examples of the compound (X) having an anion represented by the formula (IV) include compound (119) to compound (129), and are compound (125). Is preferable.
  • Examples of the compound (X) having an anion represented by the formula (V) include compound (130) to compound (139), and compound (130) and compound ( 131), compound (134), and compound (135) are preferable.
  • Examples of the compound (X) having an anion represented by the formula (VI) include compound (140) to compound (144), and compound (140) and compound ( 142), preferably compound (144).
  • Examples of the compound (X) having an anion represented by the formula (VII) (hereinafter, may be referred to as compound (VII)) include compound (145) to compound (153).
  • Examples of the compound (X) having an anion represented by the formula (VIII) include compound (154) to compound (163).
  • the compound (I) is, for example, a compound represented by the formula (M-1) (hereinafter, may be referred to as a compound (M-1)) and a compound represented by the formula (M-2) (hereinafter, a compound). It may be obtained by reacting with (M-2).
  • M-1 a compound represented by the formula (M-1)
  • M-2 a compound represented by the formula (M-2)
  • the reaction between compound (M-1) and compound (M-2) is usually carried out by mixing compound (M-1) and compound (M-2), and the base and compound (M-1). It is preferable to add compound (M-2) to the mixture with.
  • the reaction between compound (M-1) and compound (M-2) is preferably carried out in the presence of a methylating agent. It is more preferable to add compound (M-2) to a mixture of compound (M-1), a methylating agent and a base.
  • Examples of the base include metal hydroxides such as sodium hydroxide, lithium hydroxide, potassium hydroxide, cesium hydroxide, rubicium hydroxide, calcium hydroxide, barium hydroxide, and magnesium hydroxide (preferably alkali metal hydroxides).
  • metal hydroxides such as sodium hydroxide, lithium hydroxide, potassium hydroxide, cesium hydroxide, rubicium hydroxide, calcium hydroxide, barium hydroxide, and magnesium hydroxide (preferably alkali metal hydroxides).
  • Metal amides such as sodium methoxyd, potassium methoxyd, lithium methoxyd, sodium ethoxydo, sodium isopropoxide, sodium tertiary butoxide, potassium tertiary butoxide (preferably alkali metal amides); lithium hydride, sodium hydride , Metal hydrides such as potassium hydride, lithium aluminum hydride, sodium boron hydride, aluminum hydride, sodium aluminum hydride; metal oxides such as calcium oxide and magnesium oxide; sodium hydrogen carbonate, sodium carbonate, potassium carbonate, etc.
  • Metal carbonates preferably alkaline earth metal carbonates
  • organic alkyl metal compounds such as normal butyl lithium, tertiary butyl lithium, methyl lithium, glignal reagents; ammonia, triethylamine, diisopropylethylamine, ethanolamine, pyrrolidine, piperidine, Amin compounds such as diazabicycloundecene, diazabicyclononen, guanidine, tetramethylammonium hydroxide, tetraethylammonium hydroxide, pyridine, aniline, dimethoxyaniline, ammonium acetate, ⁇ -alanine (preferably triethylamine, diisopropylethylamine, etc.) Tertiary amine); metal amide compounds such as lithium diisopropylamide, sodium amide, potassium hexamethyldisilazide (preferably alkali metal amides); sulfonium compounds such as trimethylsul
  • methylating agent examples include iodomethane, dimethyl sulfate, methyl methanesulfonate, methyl fluorosulfonate, methyl paratoluenesulfonate, methyl trifluoromethanesulfonate, trimethyloxonium tetrafluoroborate and the like.
  • the amount of the methylating agent used is usually 0.1 to 10 mol, preferably 0.5 to 5 mol, based on 1 mol of compound (M-1).
  • the reaction between compound (M-1) and compound (M-2) may be carried out in the presence of a solvent.
  • Solvents include acetonitrile, benzene, toluene, acetone, ethyl acetate, chloroform, dichloroethane, monochlorobenzene, methanol, ethanol, isopropanol, tert-butanol, 2-butanone, tetrahydrofuran, diethyl ether, dimethyl sulfoxide, N, N-dimethylacetamide. , N, N-dimethylformamide, water and the like.
  • the solvent is preferably a dehydration solvent.
  • the reaction time of the compound (M-1) and the compound (M-2) is usually 0.1 to 10 hours, preferably 0.2 to 3 hours.
  • the reaction temperature of the compound (M-1) and the compound (M-2) is usually ⁇ 50 to 150 ° C., preferably ⁇ 20 to 100 ° C.
  • the amount of the compound (M-2) to be used is usually 0.1 to 10 mol, preferably 0.5 to 5 mol, based on 1 mol of the compound (M-1).
  • Examples of the compound (M-1) include the compounds described below.
  • the compound (M-2) a commercially available product may be used, and examples thereof include cloak nitrile.
  • Compound (I) obtained by reacting compound (M-1) with compound (M-2) in the presence of a base usually has a base-derived cation as a counter cation.
  • ion exchange may be carried out by mixing the compound (I) with a salt having the desired cation. The ion exchange may be carried out in the presence of a solvent.
  • the salt having a desired cation is, for example, a chloride salt composed of a desired cation and a chloride ion, a bromide salt composed of a desired cation and a bromide ion, an iodide salt composed of a desired cation and an iodide ion, and the like.
  • a fluoride salt consisting of a desired cation and a fluoride ion, a nitrate consisting of a desired cation and a nitrate ion, a sulfate consisting of a desired cation and a sulfate ion, and a perchlorine composed of a desired cation and a perchlorate ion.
  • Acid salt, sulfonate consisting of desired cation and sulfonate ion, carboxylate consisting of desired cation and carboxylic acid ion, hypochlorite consisting of desired cation and hypochlorite ion, desired Hexafluorophosphate salt composed of the above cation and hexafluorophosphate, imide salt composed of the desired cation and imide, and the like can be mentioned.
  • the compound (M-1) is a compound represented by the formula (M-3) (hereinafter, may be referred to as a compound (M-3)) and a compound represented by the formula (M-4) (hereinafter, a compound). It may be obtained by reacting with (M-4).
  • (M-3) rings W 1A , R 4 and R 5 have the same meanings as described above.
  • R 3 represents the same meaning as described above, and E 1 represents a leaving group.
  • Examples of the leaving group represented by E 1 include a halogen atom, a p-toluenesulfonyl group, a trifluoromethylsulfonyl group and the like.
  • the reaction between the compound (M-3) and the compound (M-4) is carried out by mixing the compound (M-3) and the compound (M-4).
  • the amount of the compound (M-4) to be used is usually 0.1 to 5 mol, preferably 0.5 to 2 mol, based on 1 mol of the compound (M-3).
  • the reaction between compound (M-3) and compound (M-4) is preferably carried out in the presence of a base.
  • a base include metal alkoxides (preferably alkali metal alkoxides) such as sodium methoxyd, potassium methoxyd, lithium methoxyd, sodium ethoxydo, sodium isopropoxide, sodium tertiary butoxide, and potassium tertiary butoxide; lithium hydroxide.
  • Metal hydroxides such as sodium hydroxide and potassium hydroxide, metal hydrides such as sodium hydride, lithium aluminum hydride, sodium hydride; lithium diisopropylamide, pyridine, triethylamine, diisopropylethylamine, piperidine, pyrrolidine, proline
  • metal hydroxides such as sodium hydroxide and potassium hydroxide
  • metal hydrides such as sodium hydride, lithium aluminum hydride, sodium hydride
  • lithium diisopropylamide pyridine, triethylamine, diisopropylethylamine, piperidine, pyrrolidine, proline
  • amine compounds such as.
  • the amount of the base used is usually 0.1 to 10 mol and preferably 0.5 to 5 mol with respect to 1 mol of the compound (M-3).
  • the reaction between compound (M-3) and compound (M-4) may be carried out in the presence of a solvent.
  • Solvents include acetonitrile, benzene, toluene, acetone, ethyl acetate, chloroform, dichloroethane, monochlorobenzene, methanol, ethanol, isopropanol, tert-butanol, 2-butanone, tetrahydrofuran, diethyl ether, dimethyl sulfoxide, N, N-dimethylacetamide. , N, N-dimethylformamide, water and the like.
  • Acetonitrile, tetrahydrofuran, chloroform, dichloromethane and diethyl ether are preferable, acetonitrile, tetrahydrofuran and chloroform are more preferable, and methanol, ethanol, isopropanol and acetonitrile are more preferable.
  • the reaction time of compound (M-3) and compound (M-4) is usually 0.1 to 10 hours.
  • the reaction temperature of the compound (M-3) and the compound (M-4) is usually ⁇ 50 to 150 ° C.
  • Examples of the compound (M-3) include the compounds described below.
  • the compound (M-4) a commercially available product may be used.
  • Compound (M-3) can be obtained by reacting a compound represented by the formula (M-5) (hereinafter, may be referred to as compound (M-5)) with compound (M-2a).
  • compound (M-5) a compound represented by the formula (M-5)
  • compound (M-5) a compound represented by the formula (M-5)
  • M-2a a compound represented by the formula (M-5)
  • rings W 1A , R 4 and R 5 have the same meanings as described above. ]
  • the reaction between the compound (M-5) and the compound (M-2a) can be carried out by mixing the compound (M-5) and the compound (M-2a).
  • the reaction between compound (M-5) and compound (M-2a) is preferably carried out in the presence of a base.
  • the base include the same bases used in the reaction between the compound (M-1) and the compound (M-2).
  • the amount of the base used is usually 0.1 to 5 mol, preferably 0.5 to 2 mol, based on 1 mol of the compound (M-5).
  • the reaction between compound (M-5) and compound (M-2a) may be carried out in the presence of a solvent.
  • the solvent is preferably methanol, ethanol, isopropanol, toluene, or acetonitrile.
  • the reaction time of compound (M-5) and compound (M-2a) is usually 0.1 to 10 hours.
  • the reaction temperature of compound (M-5) and compound (M-2a) is usually ⁇ 50 to 150 ° C.
  • the amount of the compound (M-2a) to be used is usually 0.1 to 10 mol, preferably 0.5 to 2 mol, based on 1 mol of the compound (M-5).
  • Examples of the compound (M-5) include the compounds described below.
  • compound (I) when the combination of R 1 and R 2 and the combination of R 4 and R 5 are the same, compound (I) is a compound represented by the formula (M-6) (hereinafter, compound). It can also be obtained by reacting (M-6) with the compound (M-2). [In the formula (M-6), the rings W 1A and R 3 have the same meanings as described above. ]
  • the reaction between compound (M-6) and compound (M-2) can be carried out by mixing compound (M-6) and compound (M-2).
  • the reaction between compound (M-6) and compound (M-2) is preferably carried out in the presence of a base or a methylating agent, more preferably in the presence of a base and methyl.
  • the reaction between compound (M-6) and compound (M-2) is more preferably a mixture of compound (M-6), compound (M-2), a base and a methylating agent. It is more preferable to mix the compound (M-2) and the base with the mixture of the compound (M-6) and the methylating agent.
  • Examples of the base used in the reaction between the compound (M-6) and the compound (M-2) include the same bases used in the reaction between the compound (M-1) and the compound (M-2). Metal carbonates are preferred, and alkaline earth metal carbonates are more preferred.
  • the amount of the base used is usually 0.1 to 5 mol and preferably 0.5 to 2 mol with respect to 1 mol of the compound (M-6).
  • the methylating agent used in the reaction between the compound (M-6) and the compound (M-2) is the same as the methylating agent used in the reaction between the compound (M-1) and the compound (M-2). However, it is preferably dimethyl sulfate.
  • the amount of the methylating agent used is usually 0.1 to 5 mol and preferably 0.5 to 2 mol with respect to 1 mol of the compound (M-6).
  • the reaction between compound (M-6) and compound (M-2) may be carried out in the presence of a solvent.
  • Solvents include acetonitrile, benzene, toluene, acetone, ethyl acetate, chloroform, dichloroethane, monochlorobenzene, methanol, ethanol, isopropanol, tert-butanol, 2-butanone, tetrahydrofuran, diethyl ether, dimethyl sulfoxide, N, N-dimethylacetamide. , N, N-dimethylformamide, water and the like.
  • the solvent is preferably a dehydration solvent.
  • the reaction time of the compound (M-6) and the compound (M-2) is usually 0.1 to 10 hours, preferably 0.2 to 3 hours.
  • the reaction temperature of the compound (M-6) and the compound (M-2) is usually ⁇ 50 to 150 ° C., preferably ⁇ 20 to 100 ° C.
  • the amount of the compound (M-2) to be used is usually 0.1 to 10 mol, preferably 0.5 to 5 mol, based on 1 mol of the compound (M-6).
  • Examples of the compound (M-6) include 2-methyl-1,3-cyclohexanedione.
  • the molecular weight of compound (X) is preferably 3000 or less, more preferably 2000 or less, and even more preferably 1000 or less. Further, it is preferably 50 or more, more preferably 100 or more, and further preferably 200 or more.
  • Compound (X) preferably exhibits maximum absorption at a wavelength of 400 to 550 nm.
  • the maximum absorption wavelength ( ⁇ max) of compound (X) is preferably a wavelength of 410 to 500 nm, more preferably a wavelength of 420 to 480 nm, and even more preferably a wavelength of 430 to 450 nm.
  • the gram absorption coefficient ⁇ at the maximum absorption wavelength ( ⁇ max) is preferably 0.5 or more, more preferably 1.0 or more, and particularly preferably 1.5 or more.
  • the upper limit is not particularly limited, but is generally 10 or less.
  • the gram absorption coefficient ⁇ at ⁇ max of compound (X) is 0.5 or more, it is preferable from the viewpoint that light called blue light can be efficiently absorbed.
  • Compound (X) preferably satisfies the following formula (a). ⁇ ( ⁇ max ) / ⁇ ( ⁇ max + 30 nm) ⁇ 5 (a) Wherein, epsilon (.lambda.max) represents the gram extinction coefficient at the maximum absorption wavelength (lambda max). ⁇ ( ⁇ max + 30 nm) represents the gram absorption coefficient at the maximum absorption wavelength ( ⁇ max) + 30 nm. The unit of the gram extinction coefficient is L / (g ⁇ cm). ] The compound (X) preferably has ⁇ ( ⁇ max) / ⁇ ( ⁇ max + 30 nm) of 5 or more, preferably 10 or more, and particularly preferably 20 or more.
  • the upper limit is not particularly limited, but is generally 1000 or less.
  • ⁇ ( ⁇ max) / ⁇ ( ⁇ max + 30 nm) is 5 or more, it is preferable because coloring of the composition containing the compound (X) can be minimized and only blue light can be selectively absorbed.
  • it is suitable because it can contribute to suppressing the influence on the color display of a display or the like and expanding the color gamut.
  • the present invention also includes a composition containing compound (X) (preferably any one of compound (I) to compound (VIII)).
  • the composition containing the compound (X) of the present invention is the compound (X) (preferably any of the compounds (I) to (VIII)).
  • the resin composition contains any one) and a resin.
  • the above composition can be used for all purposes, but it can be particularly preferably used for applications that may be exposed to light including sunlight or ultraviolet rays.
  • Specific examples include, for example, glass substitutes and their surface coating materials; window glass for dwellings, facilities, transportation equipment, etc., coating materials for light-collecting glass and light source protection glass; window films for dwellings, facilities, transportation equipment, etc .; dwellings, Interior / exterior materials and interior / exterior paints for facilities, transportation equipment, etc.
  • alkyd resin lacquer coatings and coatings formed by the coatings alkyd resin lacquer coatings and coatings formed by the coatings; acrylic lacquer coatings and coatings formed by the coatings; fluorescence Materials for light sources that emit ultraviolet rays such as lamps and mercury lamps; Materials for precision machinery, electronic and electrical equipment, materials for blocking electromagnetic waves generated from various displays; Containers or packaging materials for foods, chemicals, chemicals, etc .; Bottles, boxes, blister , Cups, special packaging, compact disc coats, agricultural and industrial sheets or film materials; anti-fading agents for printed matter, dyes, dyes, etc .; for polymer supports (eg, for plastic parts such as machine and automotive parts) ) Protective film; Printed matter overcoat; Inkjet medium coating; Laminated matte; Optical light film; Safety glass / front glass intermediate layer; Electrochromic / Photochromic applications; Overlaminated film; Solar heat control film; Sunscreen cream, shampoo, rinse , Cosmetics such as hairdressers; Textile products and textiles for clothing such
  • the molded product obtained by molding the above composition is preferably a polymer molded product.
  • the shape of the molded product may be flat film-like, powder-like, spherical particle-like, crushed particle-like, massive continuous body, fibrous, tubular, hollow thread-like, granular, plate-like, or porous. good.
  • the resin used in the resin composition includes thermoplastic resins, thermosetting resins and the like conventionally used in the production of various known molded products, sheets, films and the like.
  • the thermoplastic resin include olefin resins such as polyethylene resins, polypropylene resins, and polycycloolefin resins, poly (meth) acrylic acid ester resins, polystyrene resins, styrene-acrylonitrile resins, and acrylonitrile-butadiene-styrene resins.
  • Resin polyvinyl chloride resin, vinylidene chloride resin, vinyl acetate resin, polyvinyl butyral resin, ethylene-vinyl acetate copolymer, ethylene-vinyl alcohol resin, polyethylene terephthalate resin, polybutylene terephthalate resin, Examples thereof include polyester resins such as liquid crystal polyester resins, polyacetal resins, polyamide resins, polycarbonate resins, polyurethane resins and polyphenylene sulfide resins. One or more of these resins may be used as a polymer blend or polymer alloy.
  • thermosetting resin examples include epoxy resin, melamine resin, unsaturated polyester resin, phenol resin, urea resin, alkyd resin, and thermosetting polyimide resin.
  • the resin is preferably a transparent resin.
  • the resin composition can be obtained by mixing compound (X) and a resin.
  • the compound (X) may be contained in an amount necessary for imparting desired performance, for example, 0.00001 to 99 parts by mass with respect to 100 parts by mass of the resin.
  • the composition of the present invention may contain other additives such as a solvent, a cross-linking catalyst, a tack fire, a plasticizer, a softener, a dye, a pigment, and an inorganic filler, if necessary.
  • the composition and the resin composition may be compositions for spectacle lenses.
  • a spectacle lens can be formed by molding or the like using a composition for a spectacle lens.
  • the molding method of the composition for an spectacle lens may be injection molding or cast polymerization molding.
  • the casting polymerization molding is a method in which a composition for a spectacle lens mainly composed of a monomer or an oligomer resin is injected into a lens mold, and the composition for a spectacle lens is cured by heat or light to be molded into a lens.
  • the composition for an spectacle lens may have a composition suitable for the molding method.
  • a resin composition for a spectacle lens containing a resin and a compound (X) may be used.
  • the spectacle lens is formed by casting polymerization molding, it may be a composition for spectacle lenses containing a curable monomer that is cured by heat or light and compound (X).
  • the resin contained in the composition for spectacle lenses examples include the above-mentioned resins, and a transparent resin is preferable.
  • the resin contained in the composition for spectacle lenses is a polymer blend or polymer alloy of one or more of poly (meth) acrylic acid ester resin, polycarbonate resin, polyamide resin, polyurethane resin, and polythiourethane resin. It is preferable to use as. Moreover, it may contain not only a polymer but also a monomer component.
  • the lens composition for spectacles may be a composition containing a curable monomer and compound (X).
  • the curable monomer may contain two or more kinds. Specifically, it may be a mixture of a polyol compound and an isocyanate compound, a mixture of a thiol compound and an isocyanate compound, preferably a mixture of a thiol compound and an isocyanate, and a mixture of a polyfunctional thiol compound and a polyfunctional isocyanate compound. More preferably.
  • the thiol compound is not particularly limited as long as it is a compound having at least one thiol group in the molecule. It may be chain-shaped or cyclic. In addition, the molecule may have a sulfide bond, a polysulfide bond, or another functional group. Specific examples of the thiol compound include one thiol group in one molecule described in JP-A-2004-315556, such as an aliphatic polythiol compound, an aromatic polythiol compound, a thiol group-containing cyclic compound, and a thiol group-containing sulfide compound. Examples thereof include thiol group-containing organic compounds having the above.
  • a polyfunctional thiol compound having two or more thiol groups is preferable, and an aliphatic polythiol compound having two or more thiol groups and two or more thiol groups are preferable in terms of improving the refractive index of the lens and the glass transition temperature.
  • the sulfide compound contained is more preferable, bis (mercaptomethyl) sulfide, 1,2-bis [(2-mercaptoethyl) thio] -3-mercaptopropane, pentaerythritol tetraxthiopropionate, 4,8-dimercaptomethyl. -1,11-Mercapto-3,6,9-Trithiaundecane is more preferred.
  • the thiol compound may be used alone or in combination of two or more.
  • the isocyanate compound is preferably a polyfunctional isocyanate compound having at least two isocyanato groups (-NCO) in the molecule, for example, an aliphatic isocyanate compound (for example, hexamethylene diisocyanate) or an alicyclic isocyanate compound (for example).
  • an aliphatic isocyanate compound for example, hexamethylene diisocyanate
  • an alicyclic isocyanate compound for example.
  • isophorone diisocyanate hydrogenated diphenylmethane diisocyanate, hydrogenated xylylene diisocyanate
  • aromatic isocyanate compounds for example, tolylene diisocyanate, xylylene diisocyanate, diphenylmethane diisocyanate, naphthalenedi isocyanate, triphenylmethane triisocyanate, etc.
  • an adduct (adduct) of the isocyanate compound made of a polyhydric alcohol compound for example, an adduct made of glycerol, trimethylolpropane, etc.
  • an isocyanurate for example, an isocyanurate, a bullet-type compound, a polyether polyol, a polyester polyol, an acrylic polyol, and a polybutadiene.
  • It may be a derivative such as a urethane prepolymer type isocyanate compound which has been subjected to an addition reaction with a polyol, a polyisoprene polyol, or the like.
  • a curing catalyst may be contained in order to improve the curability.
  • the curing catalyst include tin compounds such as dibutyltin chloride, amines, phosphins, quaternary ammonium salts, quaternary phosphonium salts, tertiary sulfonium salts, and secondary compounds described in JP-A-2004-315556.
  • Class iodonium salts mineral acids, Lewis acids, organic acids, silicic acids, boric acids tetrafluoride, peroxides, azo compounds, condensates of aldehydes and ammonia compounds, guanidines, thioureas, thiazoles, Examples thereof include sulfenamides, thiurams, dithiocarbamates, xanthogenates, acidic phosphoric acid esters and the like.
  • These curing catalysts may be used alone or in combination of two or more.
  • the content of the compound (X) in the composition for spectacle lenses can be, for example, 0.01 to 20 parts by mass with respect to 100 parts by mass of the resin.
  • the content of the compound (X) can be 0.00001 to 20 parts by mass with respect to 100 parts by mass of the curable component.
  • the content of the compound (X) is preferably 0.0001 to 15 parts by mass, more preferably 0.001 to 10 parts by mass, and further preferably 0 with respect to 100 parts by mass of the resin or the curable component. It is 0.01 to 5 parts by mass, and particularly preferably 0.1 to 3 parts by mass.
  • the amount of the curing catalyst added is preferably 0.0001 to 10.0% by mass, more preferably 0.001 to 5.0% by mass, based on 100% by mass of the spectacle lens composition.
  • the composition for spectacle lenses may contain other additives.
  • the composition of the present invention When the composition of the present invention is used for optical products such as an optical filter, it can be applied to, for example, an optical display device.
  • the layer formed from the resin composition may be any of a film layer, an adhesive layer, a coat layer and the like, and is an adhesive layer and a coat layer. Is preferable.
  • the pressure-sensitive adhesive layer is a pressure-sensitive adhesive composition containing a resin (A), a compound (X), a cross-linking agent (B) and a silane compound (C).
  • the pressure-sensitive adhesive composition (i) may be further referred to as a light-absorbing compound (F) other than the radical-curable component (D), the initiator (E), and the compound (X) (hereinafter, the light-selective absorbing compound (F)).
  • It may contain an antistatic agent or the like, and preferably contains at least one selected from the group consisting of a radical curable component (D), an initiator (E) and a light selective absorption compound (F). ..
  • the resin (A) is not particularly limited as long as it is a resin used in the pressure-sensitive adhesive composition.
  • the resin (A) preferably does not exhibit maximum absorption in the wavelength range of 300 nm to 780 nm.
  • the resin (A) is preferably a resin having a glass transition temperature (Tg) of 40 ° C. or lower.
  • the glass transition temperature (Tg) of the resin (A) is more preferably 20 ° C. or lower, further preferably 10 ° C. or lower, and particularly preferably 0 ° C. or lower.
  • the glass transition temperature of the resin (A) is usually ⁇ 80 ° C. or higher, preferably ⁇ 70 ° C. or higher, more preferably ⁇ 60 ° C.
  • the glass transition temperature of the resin (A) is 40 ° C. or lower, it is advantageous to improve the adhesion of the pressure-sensitive adhesive layer formed from the pressure-sensitive adhesive composition (i) to the adherend. Further, when the glass transition temperature of the resin (A) is ⁇ 80 ° C. or higher, it is advantageous to improve the durability of the pressure-sensitive adhesive layer formed from the pressure-sensitive adhesive composition (i).
  • the glass transition temperature can be measured by a differential scanning calorimeter (DSC).
  • Examples of the resin (A) include (meth) acrylic resin, silicone resin, rubber resin, urethane resin and the like, and (meth) acrylic resin is preferable.
  • the (meth) acrylic resin is preferably a polymer containing a constituent unit derived from the (meth) acrylic acid ester as a main component (preferably containing 50% by mass or more).
  • the structural unit derived from the (meth) acrylic acid ester is a simple structural unit derived from a monomer other than one or more (meth) acrylic acid esters (for example, having a polar functional group such as a hydroxyl group, a carboxyl group, or an amino group).
  • a structural unit derived from a monomer may be included.
  • the content of the resin (A) is usually 50% by mass to 99.9% by mass, preferably 60% by mass to 95% by mass, based on 100% by mass of the solid content of the pressure-sensitive adhesive composition (i). It is preferably 70% by mass to 90% by mass.
  • the content of the compound (X) is usually 0.01 to 20 parts by mass, preferably 0.1 to 20 parts by mass, and more preferably 0.2 to 0.2 parts by mass with respect to 100 parts by mass of the resin (A). It is 10 parts by mass, and particularly preferably 0.5 to 5 parts by mass.
  • cross-linking agent (B) examples include isocyanate-based cross-linking agents, epoxy-based cross-linking agents, aziridine-based cross-linking agents, metal chelate-based cross-linking agents, and the like, and in particular, the pot life of the pressure-sensitive adhesive composition (i) and the durability of the pressure-sensitive adhesive layer. From the viewpoint of properties, cross-linking rate and the like, an isocyanate-based cross-linking agent is preferable.
  • the content of the cross-linking agent (B) is usually 0.01 to 25 parts by mass, preferably 0.1 to 15 parts by mass, and more preferably 0.15 parts by mass with respect to 100 parts by mass of the resin (A). It is ⁇ 7 parts by mass, more preferably 0.2 to 5 parts by mass, and particularly preferably 0.25 to 2 parts by mass.
  • silane compound (C) examples include vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris (2-methoxyethoxy) silane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropyltriethoxysilane, and 3 -Glysidoxypropylmethyldimethoxysilane, 3-glycidoxypropylethoxydimethylsilane, 2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane, Examples thereof include 3-methacryloyloxypropyltrimethoxysilane and 3-mercaptopropyltrimethoxysilane.
  • the silane compound (C) may be a silicone oligomer.
  • the content of the silane compound (C) is usually 0.01 to 20 parts by mass, preferably 0.1 to 10 parts by mass, and more preferably 0.15 with respect to 100 parts by mass of the resin (A). It is ⁇ 7 parts by mass, more preferably 0.2 to 5 parts by mass, and particularly preferably 0.25 to 2 parts by mass.
  • radical curable component (D) examples include radical curable components such as compounds or oligomers that are cured by a radical polymerization reaction.
  • examples of the radically polymerizable component (D) include (meth) acrylate-based compounds, styrene-based compounds, and vinyl-based compounds.
  • the pressure-sensitive adhesive composition (i) may contain two or more radical curable components (D).
  • Examples of the (meth) acrylate-based compound include a (meth) acrylate monomer having at least one (meth) acryloyloxy group in the molecule, a (meth) acrylamide monomer, and at least two (meth) acryloyl groups in the molecule.
  • (Meta) acryloyl group-containing compounds such as (meth) acrylic oligomers having the above can be mentioned.
  • the (meth) acrylic oligomer is preferably a (meth) acrylate oligomer having at least two (meth) acryloyloxy groups in the molecule.
  • As the (meth) acrylate compound only one kind may be used alone, or two or more kinds may be used in combination.
  • the (meth) acrylate monomer includes a monofunctional (meth) acrylate monomer having one (meth) acryloyloxy group in the molecule and a bifunctional (meth) acrylate having two (meth) acryloyloxy groups in the molecule.
  • Examples include monomers and polyfunctional (meth) acrylate monomers having three or more (meth) acryloyloxy groups in the molecule. It is preferably a (meth) acrylate compound, and more preferably a polyfunctional (meth) acrylate compound.
  • the polyfunctional (meth) acrylate compound is preferably trifunctional or higher.
  • the content of the radical curable component (D) is usually 0.5 to 100 parts by mass, preferably 1 to 70 parts by mass, and 3 to 50 parts by mass with respect to 100 parts by mass of the resin (A). It is more preferably 5 to 30 parts by mass, and particularly preferably 7.5 to 25 parts by mass.
  • the initiator (E) is either a compound that induces a polymerization reaction by absorbing heat energy (thermal polymerization initiator) or a compound that induces a polymerization reaction by absorbing light energy (photopolymerization initiator). May be good.
  • the light is preferably an active energy ray such as visible light, ultraviolet light, X-ray, or electron beam.
  • thermal polymerization initiator examples include compounds that generate radicals by heating (thermal radical generators), compounds that generate acids by heating (thermal acid generators), and compounds that generate bases by heating (thermal base generators). ) Etc. can be mentioned.
  • Photopolymerization initiators include compounds that generate radicals by absorbing light energy (photoradical generators), compounds that generate acids by absorbing light energy (photoacid generators), and light energy. Examples thereof include compounds that generate a base by absorbing the above (photobase generator).
  • the initiator (E) it is preferable to select one suitable for the polymerization reaction of the above-mentioned radical curable component (D), more preferably a radical polymerization initiator, and preferably a photoradical polymerization initiator. More preferred.
  • the radical polymerization initiator include an alkylphenone compound, a benzoin compound, a benzophenone compound, an oxime ester compound, a phosphine compound and the like.
  • the radical polymerization initiator is preferably a photoradical polymerization initiator, and more preferably an oxime ester-based photoradical polymerization initiator from the viewpoint of the reactivity of the polymerization reaction.
  • the reaction rate of the radical curing component (D) can be increased even under curing conditions where the illuminance or the amount of light is weak.
  • the content of the initiator (E) is usually 0.01 to 20 parts by mass, preferably 0.3 to 10 parts by mass, and 0.5 to 5 parts by mass with respect to 100 parts by mass of the resin (A). It is more preferably parts by mass, more preferably 0.75 to 4 parts by mass, and particularly preferably 1 to 3 parts by mass.
  • the light selective absorption compound (F) is a light-absorbing compound other than the compound (X), and is, for example, a compound (ultraviolet absorber) that absorbs light having a wavelength of 250 nm to 380 nm (preferably a wavelength of 250 nm or more and less than 360 nm). Alternatively, it is a compound (dye) that absorbs light having a wavelength of 380 nm to 780 nm, or a compound (infrared absorber) that absorbs light having a wavelength of 780 nm to 1500 nm.
  • a compound (ultraviolet absorber) that absorbs light having a wavelength of 250 nm to 380 nm (preferably a wavelength of 250 nm or more and less than 360 nm).
  • it is a compound (dye) that absorbs light having a wavelength of 380 nm to 780 nm, or a compound (infrared absorber) that absorbs light having a wavelength of 7
  • the structure of the ultraviolet absorber is not particularly limited as long as it is a compound that absorbs light having a wavelength of 250 nm to 380 nm, but a benzotriazole compound, a benzophenone compound, a triazine compound, a salicylic acid compound, a cyanoacrylate compound, Compounds such as benzoxazine compounds are preferable.
  • the content of the light selective absorption compound (F) is usually 0.1 to 50 parts by mass, preferably 0.2 to 40 parts by mass, and more preferably 0 with respect to 100 parts by mass of the resin (A). It is .5 to 30 parts by mass, more preferably 1 to 25 parts by mass, and particularly preferably 2 to 20 parts by mass.
  • the molded product formed from the composition containing the compound (X) preferably has a transmittance of 50% or less, more preferably 30% or less at a wavelength of 440 nm.
  • Example 1 Synthesis of compound represented by formula (1) The inside of a 100 mL-four-necked flask equipped with a Dimroth condenser and a thermometer is set to a nitrogen atmosphere, and 2 parts of 2-methyl-1,3-cyclohexanedione, 1.3 parts of dimethyl sulfate, and 10 parts of acetonitrile are added and heated for 3 hours. The mixture was refluxed and stirred. 0.75 parts of malononitrile, 1.2 parts of potassium carbonate and 10 parts of isopropanol were mixed with the obtained mixture, and the mixture was heated under reflux for 3 hours and stirred. After distilling off the solvent from the obtained mixture, the mixture was purified to obtain 0.1 part of the compound represented by the formula (1).
  • ⁇ Maximum absorption wavelength and gram absorption coefficient ⁇ measurement> A 2-butanone solution (0.006 g / L) of the obtained compound represented by the formula (1) was placed in a 1 cm quartz cell, and the quartz cell was set in a spectrophotometer UV-2450 (manufactured by Shimadzu Corporation). Then, the absorbance in the wavelength range of 300 to 800 nm was measured every 1 nm step by the double beam method. The gram extinction coefficient for each wavelength was calculated from the obtained absorbance value, the concentration of the compound represented by the formula (1) in the solution, and the optical path length of the quartz cell.
  • ⁇ ( ⁇ ) A ( ⁇ ) / CL
  • ⁇ ( ⁇ ) represents the gram extinction coefficient (L / (g ⁇ cm)) of the compound represented by the formula (1) at the wavelength ⁇ nm
  • a ( ⁇ ) represents the absorbance at the wavelength ⁇ nm
  • C represents the concentration (g / L)
  • L represents the optical path length (cm) of the quartz cell.
  • the maximum absorption wavelength of the obtained compound represented by the formula (1) was 457 nm.
  • the obtained compound represented by the formula (1) has ⁇ ( ⁇ max) of 150.6 L / (g ⁇ cm), ⁇ ( ⁇ max + 30 nm) of 3.8 L / (g ⁇ cm), and ⁇ ( ⁇ max) / ⁇ ( ⁇ max + 30 nm) was 39.6.
  • Example 2 Synthesis of compound represented by formula (2) A nitrogen atmosphere is created in a 300 mL-four-necked flask equipped with a Dimroth condenser and a thermometer, and 70 parts of dimedone, 10.4 parts of malononitrile, 40.6 parts of diisopropylethylamine, and 100 parts of ethanol are charged, and the mixture is heated under reflux for 3 hours and stirred. I let you. The solvent was distilled off from the obtained mixture and the mixture was purified to obtain 15.1 part of the compound represented by the formula (M-5).
  • the maximum absorption wavelength and the gram absorption coefficient were measured in the same manner as above.
  • the maximum absorption wavelength of the obtained compound represented by the formula (2) was 432 nm.
  • the obtained compound represented by the formula (2) has ⁇ ( ⁇ max) of 237 L / (g ⁇ cm), ⁇ ( ⁇ max + 30 nm) of 4.4 L / (g ⁇ cm), and ⁇ ( ⁇ max) / ⁇ ( ⁇ max + 30 nm).
  • ⁇ ( ⁇ max) 237 L / (g ⁇ cm)
  • ⁇ ( ⁇ max) / ⁇ ( ⁇ max + 30 nm) was 53.9.
  • Example 3 Preparation of resin composition (1) (adhesive composition (1))
  • Polymerization example 1 Preparation of acrylic resin (A) A reaction vessel equipped with a cooling tube, a nitrogen introduction tube, a thermometer and a stirrer. A mixed solution of 81.8 parts of ethyl acetate, 96 parts of butyl acrylate, 3 parts of 2-hydroxyethylmethyl acrylate, and 1 part of acrylic acid was charged as a solvent, and the air in the reaction vessel was replaced with nitrogen gas. The internal temperature was raised to 55 ° C. while containing no oxygen.
  • acrylic resin (A) was referred to as acrylic resin (A).
  • a cross-linking agent (manufactured by Toso Co., Ltd .: trade name "Coronate L", isocyanate compound, solid content 75%) is 0 with respect to 100 parts of the solid content of the ethyl acetate solution (resin concentration: 20%) of the acrylic resin (A). .3 parts, 0.28 parts of silane compound (manufactured by Shin-Etsu Chemical Industry Co., Ltd .: trade name "KBM3066"), 1.5 parts of the compound represented by the formula (2) are mixed, and the solid content concentration is 14%. Ethyl acetate was added so as to obtain a resin composition (1) (adhesive composition).
  • the blending amount of the above-mentioned cross-linking agent is the number of parts by mass as the active ingredient.
  • Examples 4 to 7 and Comparative Example 1 Preparation of Resin Compositions (2) to (6) As shown in Table 10, each component and the content of each component were changed in the same manner as in Example 3.
  • the pressure-sensitive adhesive composition (2) to the pressure-sensitive adhesive composition (6) were prepared.
  • the amount of the cross-linking agent blended is the number of parts by mass as the active ingredient, and the resin (A) is the number of parts by mass of the solid content.
  • Acrylic resin (A) Acrylic resin (A) synthesized in Polymerization Example 1
  • the obtained resin molded body (1) was attached to a cycloolefin film containing an ultraviolet absorber having a thickness of 23 ⁇ m [trade name “ZEONOR” obtained from Nippon Zeon Corporation] by a laminator, and then the temperature was 23 ° C. and the relative humidity was 65.
  • the mixture was cured under the condition of% for 7 days to obtain a laminate (1) of a cycloolefin film / resin molded product (1) / separate film.
  • a resin molded body (2), a laminated body (2), and a resin molded body with a double-sided separate film (2) were prepared using the resin composition (2) instead of the resin composition (1), and evaluated in the same manner. went. The results are shown in Table 11.
  • a resin molded body (3), a laminated body (3), and a resin molded body with a double-sided separate film (3) were prepared using the resin composition (3) instead of the resin composition (1), and evaluated in the same manner. went. The results are shown in Table 11.
  • a resin molded body (6), a laminated body (6), and a resin molded body with a double-sided separate film (6) were prepared using the resin composition (6) instead of the resin composition (1), and evaluated in the same manner. went. The results are shown in Table 11.
  • UV-A (wavelength 320 to 390 nm) was adjusted to an illuminance of 500 mW and an integrated light amount of 500 mJ using an ultraviolet irradiation device (“Fusion UV Systems Co., Ltd.“ Electrodeless UV lamp system H valve ”).
  • a resin molded body (adhesive layer) (4) was produced by irradiating with ultraviolet rays.
  • the obtained resin molded product (4) was bonded to non-alkali glass, the separate film was peeled off, and then the resin molded product (4) was coated with a 23 ⁇ m ultraviolet absorber-containing cycloolefin film [a product obtained from Nippon Zeon Co., Ltd.].
  • the name "ZEONOR”] was laminated to prepare a laminated body (4) having a cycloolefin film / resin molded body (4) / glass structure.
  • the prepared laminate (4) was set in a spectrophotometer UV-2450 (manufactured by Shimadzu Corporation), and the absorbance was measured in the wavelength range of 300 to 800 nm in 1 nm steps by the double beam method.
  • the measured absorbance at a wavelength of 440 nm was defined as the absorbance of the resin molded product (4) at a wavelength of 440 nm.
  • the absorbance at a wavelength of 330 nm and a wavelength of 440 nm of the non-alkali glass simple substance and the cycloolefin film simple substance are 0, respectively.
  • a resin molded body (5), a laminated body (5), and a resin molded body with a double-sided separate film (5) were prepared using the resin composition (5) instead of the resin composition (4), and evaluated in the same manner. went. The results are shown in Table 11.
  • Example 8 Preparation of resin composition for spectacle lens and molded product thereof 40 parts of xylylene diisocyanate, 60 parts of trimethylolpropane tris (thioglycolate), compound represented by the formula (2) synthesized in Example 2. 0.01 part, 0.2 part of a release agent (trade name: ZELEC-UN, obtained from Sigma-Aldrich), and 0.03 part of dibutyldichlorotin as a curing catalyst were mixed and stirred. The obtained mixture was allowed to stand in a vacuum dryer for 1 hour and degassed. The resulting mixture was poured into a glass mold and heated at a temperature of 120 ° C. for 1 hour. Only the molded body was peeled off from the glass mold to prepare a resin plate having a thickness of 2 mm, 3 cm ⁇ 3 cm as the molded body.
  • acrylic resin (A1) had a polystyrene-equivalent weight average molecular weight Mw of 1.25 million and Mw / Mn of 4.5 by GPC. This is referred to as acrylic resin (A1).
  • the pressure-sensitive adhesive composition (7) to the pressure-sensitive adhesive composition (9) were prepared in the same manner as in Example 3 except that each component and the content of each component were changed as shown in Table 14.
  • the amount of the cross-linking agent blended is the number of parts by mass as the active ingredient, and the resin (A) is the number of parts by mass of the solid content.
  • Acrylic resin (A1) Acrylic resin (A1) synthesized in Polymerization Example 2 Formula (2): Compound represented by the formula (2) synthesized in Example 2 Coronate L: manufactured by Toso Co., Ltd., trade name: coronate L, isocyanate-based cross-linking agent KBM3066: manufactured by Shin-Etsu Chemical Co., Ltd., trade name: KBM3066, silane coupling agent KBM403: manufactured by Shin-Etsu Chemical Co., Ltd., trade name: KBM403, silane coupling agent M-130G: manufactured by Shin-Nakamura Chemical Industry Co., Ltd., trade name: M-130G, monofunctional methoxypolyethylene glycol methacrylate ion Sex compound: An ionic compound represented by the following formula
  • the obtained resin molded body (7) was attached to a cycloolefin film containing an ultraviolet absorber having a thickness of 23 ⁇ m [trade name “ZEONOR” obtained from Nippon Zeon Corporation] by a laminator, and then the temperature was 23 ° C. and the relative humidity was 65.
  • the mixture was cured under the condition of% for 7 days to obtain a laminate (7) of a cycloolefin film / resin molded product (7) / separate film.
  • a resin molded body (8), a laminated body (8), and a resin molded body with a double-sided separate film (7) were prepared using the resin composition (8) instead of the resin composition (7), and evaluated in the same manner. went. The results are shown in Table 15.
  • a resin molded body (9), a laminated body (9), and a resin molded body with a double-sided separate film (9) were prepared using the resin composition (9) instead of the resin composition (7), and evaluated in the same manner. went. The results are shown in Table 15.
  • the compound of the present invention has high absorption selectivity for short wavelength visible light having a wavelength of 440 nm.
  • the resin composition containing the compound of the present invention has a high absorbance retention rate even after the weather resistance test, and has good weather resistance.

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WO2022168754A1 (ja) * 2021-02-04 2022-08-11 住友化学株式会社 化合物

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WO2022168754A1 (ja) * 2021-02-04 2022-08-11 住友化学株式会社 化合物

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