WO2023287209A1 - Compound, composition comprising same, molded product, dyed product, and optical layer - Google Patents

Compound, composition comprising same, molded product, dyed product, and optical layer Download PDF

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WO2023287209A1
WO2023287209A1 PCT/KR2022/010249 KR2022010249W WO2023287209A1 WO 2023287209 A1 WO2023287209 A1 WO 2023287209A1 KR 2022010249 W KR2022010249 W KR 2022010249W WO 2023287209 A1 WO2023287209 A1 WO 2023287209A1
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compound
formula
group
ring
carbon atoms
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PCT/KR2022/010249
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French (fr)
Korean (ko)
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아사즈유우지
쿠몬코오지
니시카미유키
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동우 화인켐 주식회사
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Priority to KR1020237026420A priority Critical patent/KR20230131477A/en
Priority to CN202280029107.1A priority patent/CN117177966A/en
Publication of WO2023287209A1 publication Critical patent/WO2023287209A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/45—Carboxylic acid nitriles having cyano groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C255/47—Carboxylic acid nitriles having cyano groups bound to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of rings being part of condensed ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/01—Sulfonic acids
    • C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C309/45—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton
    • C07C309/46—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton having the sulfo groups bound to carbon atoms of non-condensed six-membered aromatic rings
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C317/32—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C323/31—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • 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
    • C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • 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
    • C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
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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
    • C07D209/44—Iso-indoles; Hydrogenated iso-indoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D211/70—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/04—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
    • C07D215/06—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms having only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/04—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
    • C07D215/10—Quaternary compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C07D233/58—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • C07D249/06—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles with aryl radicals directly attached to ring atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/16—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
    • C07D249/18—Benzotriazoles
    • C07D249/20—Benzotriazoles with aryl radicals directly attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • 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
    • C08K5/17—Amines; Quaternary ammonium compounds
    • C08K5/18—Amines; Quaternary ammonium compounds with aromatically bound amino groups
    • C—CHEMISTRY; METALLURGY
    • 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
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3442—Heterocyclic compounds having nitrogen in the ring having two nitrogen atoms in the ring
    • C08K5/3445—Five-membered rings
    • C08K5/3447—Five-membered rings condensed with carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/14—All rings being cycloaliphatic
    • C07C2602/26—All rings being cycloaliphatic the ring system containing ten carbon atoms
    • C07C2602/28—Hydrogenated naphthalenes

Definitions

  • the present invention relates to a compound and a composition, a molded article, a dye and an optical layer containing the compound.
  • Pigment compounds that absorb visible light are used in a wide range of applications such as textiles, inks, paints, containers, packaging materials, prints, optical products, glasses, and display devices for the purpose of coloring objects or transmitting or absorbing light of a specific wavelength. It is being used. As important characteristics of a dye compound, selective absorption (absorption spectrum sharpness) and durability (particularly weather resistance) are mentioned.
  • the cyanine pigment can control the wavelength showing maximum absorption in a wide range from the ultraviolet region with a wavelength of 380 nm or less to the near-infrared region with a wavelength of 780 nm or more by controlling the number of methine carbon atoms in the polymethine skeleton. It has been widely used in that it exhibits high selective absorption (for example, US Patent No. 6004536).
  • cyanine dyes have high selective absorption but have poor durability (particularly, weather resistance), so a compound having good durability is required.
  • the present invention includes the following inventions.
  • Ring W 1 and ring W 2 each independently represent a ring structure having at least one double bond as a ring component.
  • Ring W 1 and ring W 2 may each independently have a substituent.
  • R 1 and R 2 each independently represent a hydrogen atom or a monovalent substituent, and at least one of R 1 and R 2 is a monovalent substituent.
  • Each of ring W 1 , ring W 2 , R 1 and R 2 has the same meaning as described above.
  • R 3 and R 4 may be connected to each other to form a ring.
  • R 5 and R 6 may be connected to each other to form a ring.
  • Each of ring W 1 , ring W 2 , R 1 and R 2 has the same meaning as described above.
  • Ar 1 and Ar 2 each independently represent an aromatic hydrocarbon group having 6 to 24 carbon atoms which may have a substituent.
  • R 4A and R 6A each independently represent a hydrogen atom or a hydrocarbon group having 6 to 24 carbon atoms which may have a substituent.
  • Ring W 3 and Ring W 4 each independently represent a nitrogen-containing heterocyclic group.
  • a resin composition comprising the compound according to any one of [1] to [7] and a resin.
  • composition containing the compound according to any one of [1] to [7] and a polymerizable monomer.
  • Ring W 1 and ring W 2 each independently represent a ring structure having at least one double bond as a ring component.
  • Ring W 1 and ring W 2 may each independently have a substituent.
  • R 1 and R 2 each independently represent a hydrogen atom or a monovalent substituent, and at least one of R 1 and R 2 is a monovalent substituent.
  • An object of the present invention is to provide a novel compound that efficiently absorbs light in the visible light region (wavelength 400 nm to wavelength 750 nm, preferably wavelength 450 nm to wavelength 600 nm) and at the same time has good weather resistance.
  • the compound of the present invention is a compound containing a cation containing a partial structure represented by the following formula (I) (hereinafter sometimes referred to as compound (I)).
  • Ring W 1 and ring W 2 each independently represent a ring structure having at least one double bond as a ring component.
  • Ring W 1 and ring W 2 may each independently have a substituent.
  • R 1 and R 2 each independently represent a hydrogen atom or a monovalent substituent, and at least one of R 1 and R 2 is a monovalent substituent.
  • a cation having a partial structure represented by formula (I) also includes all resonance structures as shown below.
  • Ring W 1 and ring W 2 each independently represent a ring structure having at least one double bond as a ring component. Ring W 1 and ring W 2 have at least one double bond as a component of the ring, but the number of double bonds included in ring W 1 and ring W 2 is usually 1 to 4, preferably 1 to 3, and 1 or It is more preferable that it is 2, and it is still more preferable that it is 1.
  • Ring W 1 and ring W 2 may each independently be monocyclic or polycyclic.
  • the ring W 1 and the ring W 2 may each independently be an aromatic ring or a non-aromatic ring (aliphatic ring), but is preferably a non-aromatic ring. If it is a ring which does not have aromaticity, the selective absorption property can be further improved.
  • Ring W 1 and ring W 2 may each independently be a heterocycle containing a hetero atom (eg, a nitrogen atom, an oxygen atom, a sulfur atom, etc.), or may be a hydrocarbon ring. It is preferable that ring W 1 and ring W 2 are each independently a ring composed of a hydrocarbon.
  • a heterocycle containing a hetero atom eg, a nitrogen atom, an oxygen atom, a sulfur atom, etc.
  • ring W 1 and ring W 2 are each independently a ring composed of a hydrocarbon.
  • Ring W 1 and ring W 2 are each independently preferably a 3-membered ring to a 20-membered ring structure, more preferably a 3-membered ring to a 12-membered ring, and preferably a 4-membered ring to a 6-membered ring. .
  • ring W 1 and ring W 2 are each independently monocyclic.
  • Ring W 1 and ring W 2 form a condensed ring.
  • the condensed ring formed by the ring W 1 and the ring W 2 is preferably a condensed ring of an aliphatic hydrocarbon, more preferably a condensed ring of an aliphatic hydrocarbon having 6 to 40 carbon atoms.
  • the condensed ring formed by ring W 1 and ring W 2 includes, for example, the condensed ring described below.
  • * represents a binding site.
  • Ring W 1 and ring W 2 may each independently have a substituent.
  • substituents include halogen atoms such as a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom; methyl group, ethyl group, propyl group, normal butyl group, isobutyl group, tert-butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, 2-ethylhexyl group, 4-butyloctyl group, aliphatic hydrocarbon groups having 1 to 25 carbon atoms (preferably alkyl groups having 1 to 12 carbon atoms) such as ethenyl, propenyl, butenyl, pentenyl, ethynyl, propynyl, allyl, cyclohexenyl and butadienyl; Fluoromethyl group, di
  • the condensed ring formed by ring W 1 and ring W 2 may also have a substituent, and the substituent may include a substituent that ring W 1 or ring W 2 may have.
  • R 1 and R 2 each independently represent a hydrogen atom or a monovalent substituent, and at least one selected from R 1 and R 2 is a monovalent substituent.
  • the monovalent substituent represented by R 1 and R 2 is not particularly limited as long as it is not a hydrogen atom, and has, for example, a monovalent aliphatic hydrocarbon group, a monovalent aromatic hydrocarbon group, an electron withdrawing group, an electron donating group, a heterocyclic group, or a polyoxyalkylene group and the like.
  • Examples of the monovalent aliphatic hydrocarbon group represented by R 1 and R 2 include methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, n-pentyl, isopentyl, n-hexyl group, isohexyl group, n-octyl group, isooctyl group, n-nonyl group, isononyl group, n-decyl group, isodecyl group, n-dodecyl group, isododecyl group, undecyl group, lauryl group , Myristyl group, cetyl group, stearyl group, 2-ethylhexyl group, straight-chain or branched chain alkyl group having 1 to 25 carbon atoms such as 4-butyloctyl group: cyclopropyl group, cyclobutyl group
  • Examples of the monovalent aromatic hydrocarbon group represented by R 1 and R 2 include a phenyl group, a naphthyl group, anthracenyl group, tetracenyl group, pentacenyl group, phenanthryl group, chrysenyl group, triphenylenyl group, tetraphenyl group, pyrenyl group, and phenyl group.
  • aryl groups having 6 to 18 carbon atoms such as a relenyl group, a coronenyl group, and a biphenyl group; aralkyl groups having 7 to 18 carbon atoms such as benzyl group, phenylethyl group and naphthylmethyl group; A phenoxyethyl group, a phenoxydiethylene glycol group, an arylalkoxy group of a phenoxypolyalkylene glycol group, etc. are mentioned, 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 1 and R 2 include a hydroxyl group; Alkoxy having 1 to 25 carbon atoms such as methoxy group, ethoxy group, propoxy group, butoxy group, pentyloxy group, hexyloxy group, heptyloxy group, octyloxy group, 2-ethylhexyloxy group, 4-butyloctyloxy group, etc.
  • an alkylthio group having 1 to 12 carbon atoms such as a methylthio group, an ethylthio group, a propylthio group, a butylthio group, a pentylthio group, and a hexylthio group; and amino groups which may be substituted with one or two alkyl groups having 1 to 6 carbon atoms, such as an amino group, a monomethylamino group, a monoethylamino group, a dimethylamino group, a diethylamino group, and a methylethylamino group.
  • Examples of the heterocyclic group represented by R 1 and R 2 include a pyrrolidine ring group, a piperidine ring group, a pyrroline ring group, an imidazolidine ring group, an imidazoline ring group, an oxazoline ring group, and a thiazoline ring group.
  • piperidine ring group piperidine ring group, morpholine ring group, piperazine ring group, indole ring group, isoindole ring group, quinoline ring group, thiophene ring group, pyrrole ring group, thiazoline ring group and furan ring group, tetrahydro and an aliphatic heterocyclic group having 4 to 20 carbon atoms, such as a furan ring group, or an aromatic heterocyclic group having 3 to 20 carbon atoms.
  • the group having a polyoxyalkylene group represented by R 1 and R 2 is a group having an oxyethylene group (-CH 2 CH 2 O-), an oxypropyl group (-CH 2 CH 2 CH 2 O-), and the like. More specifically, a group represented by -(X 11 O)mR 11 (X 11 represents an alkylene group having 1 to 6 carbon atoms, R 11 represents an alkyl group having 1 to 6 carbon atoms which may have a hydroxyl group, and m is 1 to 6 represents the integer of).
  • Examples of electron-withdrawing groups represented by R 1 and R 2 include halogen atoms, nitro groups, cyano groups, carboxy groups, halogenated alkyl groups, halogenated aryl groups, -OCF 3 , -SCF 3 , -SF 5 , -SF 3 , -SO 3 H, -SO 2 H, and a group represented by the formula (z-1).
  • R 222 represents a hydrogen atom, a halogen atom, a hydrocarbon group which may have a substituent, or a group having a polyoxyalkylene group.
  • X 1 represents -CO-, -COO-, -OCO-, -CS-, -CSS-, -COS-, -CSO-, -SO 2 -, -NR 223 CO- or -CONR 224 -.
  • R 223 and R 224 each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a phenyl group.
  • a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom are mentioned as a halogen atom.
  • Halogenated alkyl groups include trifluoromethyl, perfluoroethyl, perfluoropropyl, perfluoroisopropyl, perfluorobutyl, perfluoro sec-butyl, perfluoro tert-butyl, purple and halogenated alkyl groups having 1 to 25 carbon atoms, such as a fluoropentyl group, a perfluorohexyl group, a dichloromethyl group, a bromomethyl group, and an iodomethyl group. It is preferably a C1-C12 halogenated alkyl group, more preferably a C1-C12 fluoroalkyl group, still more preferably a C1-C12 perfluoroalkyl group.
  • Halogenated aryl groups include halogenated aryl groups having 6 to 18 carbon atoms such as fluorophenyl, chlorophenyl and bromophenyl groups, preferably fluoroaryl groups having 6 to 18 carbon atoms, and perfluoroaryl groups having 6 to 12 carbon atoms.
  • a group is more preferable, and a pentafluorophenyl group is still more preferable.
  • X 1 is preferably -CO-, -COO- or -SO 2 -.
  • the halogen atom represented by R 222 includes a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
  • Examples of the hydrocarbon group represented by R 222 include an aliphatic hydrocarbon group having 1 to 25 carbon atoms or an aromatic hydrocarbon group having 6 to 18 carbon atoms.
  • Examples of the aliphatic hydrocarbon group having 1 to 25 carbon atoms include methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, n-pentyl, n-hexyl, 1-methyl Straight-chain, branched-chain, or cyclic carbon atoms of 1 to 25, such as butyl group, 3-methylbutyl group, n-octyl group, n-decyl group, 2-hexyl-octyl group, 4-butyloctyl group and cyclohexyl group an alkyl group; unsaturated aliphatic hydrocarbon groups such as an ethenyl group, a propenyl group, a butenyl group, a pentenyl group, an ethynyl group, a propynyl group, an allyl group, a cyclohexenyl group, and
  • aromatic hydrocarbon group having 6 to 18 carbon atoms examples include aryl groups having 6 to 18 carbon atoms such as a phenyl group, a naphthyl group, anthracenyl group, and a biphenyl group; and aralkyl groups having 7 to 18 carbon atoms, such as a benzyl group, a phenylethyl group, and a naphthylmethyl group.
  • Examples of the substituent that the hydrocarbon group represented by R 222 may have include a halogen atom, a hydroxyl group, an alkoxy group, a thioalkyl group, and a dialkylamino group.
  • Examples of the group having a polyoxyalkylene group represented by R 222 include the same group as the group having a polyoxyalkylene group represented by R 1 .
  • Examples of the C1-C6 alkyl group represented by R 223 and R 224 include methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, n-pentyl, n- and straight-chain or branched-chain alkyls having 1 to 6 carbon atoms, such as a hexyl group and a 1-methylbutyl group.
  • the group represented by formula (z-1) is -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 are each independently represents a hydrocarbon group or a halogen atom which may have a substituent).
  • R 10 is an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent
  • -SO 2 CF 3 is an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent
  • -SO 2 CF 3 is an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent
  • -SO 2 CHF 2 is an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent
  • At least one selected from R 1 and R 2 is preferably an electron withdrawing group
  • a cyano group, a nitro group, -OCF 3 , -SCF 3 , -SF 5 , -SO 2 CF 3 , -SO 2 -R 10 are more preferred,
  • a cyano group or a nitro group is particularly preferred
  • a cyano group is particularly preferred.
  • the cation containing the partial structure represented by formula (I) is a cation represented by formula (I-A).
  • Each of ring W 1 , ring W 2 , R 1 and R 2 has the same meaning as described above.
  • R 3 and R 4 may be connected to each other to form a ring.
  • R 5 and R 6 may be connected to each other to form a ring.
  • Examples of the hydrocarbon group having 1 to 24 carbon atoms represented by R 3 , R 4 , R 5 and R 6 include an aliphatic hydrocarbon group having 1 to 24 carbon atoms and an aromatic hydrocarbon group having 6 to 24 carbon atoms.
  • Examples of the aliphatic hydrocarbon group having 1 to 24 carbon atoms include methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, n-pentyl, n-hexyl, 1-methyl Straight-chain, branched-chain, or cyclic carbon atoms of 1 to 24, such as butyl group, 3-methylbutyl group, n-octyl group, n-decyl group, 2-hexyl-octyl group, 4-butyloctyl group, and cyclohexyl group an alkyl group; and unsaturated aliphatic hydrocarbon groups such as ethenyl, propenyl, butenyl, pentenyl, ethynyl, propynyl, allyl, cyclohexenyl and butadienyl.
  • aromatic hydrocarbon group having 6 to 24 carbon atoms examples include aryl groups having 6 to 24 carbon atoms such as a phenyl group, a naphthyl group, an anthracenyl group, and a biphenyl group; and aralkyl groups having 7 to 24 carbon atoms such as benzyl group, phenylethyl group and naphthylmethyl group.
  • a group represented by -(X 12 O) m1 -R 12 including an oxyethylene group (-CH 2 CH 2 O-), an oxypropyl group (-CH 2 CH 2 CH 2 O-), etc.
  • R 12 represents an alkyl group having 1 to 6 carbon atoms which may have a hydroxyl group
  • m1 represents an integer of 1 to 6, and the total number of carbon atoms is 24 or less).
  • a group represented by -(X 13 S) m2 -R 13 including a thioethylene group (-CH 2 CH 2 S-), a thiopropyl group (-CH 2 CH 2 CH 2 S-), etc.
  • X 13 has 1 carbon atom) to 6 alkylene groups
  • R 13 represents an alkyl group having 1 to 6 carbon atoms which may have a hydroxyl group
  • m2 represents an integer of 1 to 6, and the total number of carbon atoms is 24 or less).
  • Substituents that the hydrocarbon group having 1 to 24 carbon atoms represented by R 3 , R 4 , R 5 and R 6 may have include halogen atoms such as fluorine, chlorine, bromine and iodine; Fluoromethyl group, difluoromethyl group, trifluoromethyl group, 2-fluoroethyl group, 2,2-difluoroethyl group, 2,2,2-trifluoroethyl group, 1,1,2,2-tetrafluoro halogenated alkyl groups having 1 to 25 carbon atoms such as roethyl group, 1,1,2,2,2-pentafluoroethyl group, and nonafluorobutyl group; 1 to 25 carbon atoms such as methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, tertiary butoxy group, pentyloxy group, hexyloxy group, 2-ethylhexyloxy group, 4-buty
  • Examples of the heterocyclic group represented by R 3 , R 4 , R 5 and R 6 include an aziridine ring group, an azetidine ring group, a pyrrolidine ring group, a piperidine ring group, a pyrroline ring group, and an imidazolidine ring group.
  • Pyrazolidine ring group imidazolidine ring group, imidazoline ring group, oxazoline ring group, thiazoline ring group, piperidine ring group, morpholine ring group, piperazine ring group, indole ring group
  • a ring formed by connecting R 3 and R 4 is a ring containing a nitrogen atom as a component of the ring.
  • a ring formed by connecting R 3 and R 4 may contain a hetero atom other than a nitrogen atom as a component of the ring.
  • a ring formed by connecting R 3 and R 4 may be a monocyclic ring or a condensed ring. Examples of the ring formed by connecting R 3 and R 4 include an aziridine ring group, an azetidine ring group, a pyrrolidine ring group, a piperidine ring group, a morpholine ring group, an indoline ring group, and an imidazoline ring.
  • Ring group pyrazole ring group, imidazole ring group, triazole ring group, tetrazole ring group, thiazolidinedione ring group, succinimide ring group, oxazolidone ring group, piperazine ring group, thiomorpholine Ring group, decahydroisoquinoline ring group, decahydroquinoline ring group, tetrahydroquinoline ring group, carbazole ring group, phenothiazine ring group, azaadamantane ring group, azocan ring group, azonane ring group, etc.
  • a hydrogen atom included in a ring formed by linking R 3 and R 4 to each other may be substituted with an arbitrary substituent, and the optional substituent includes, for example, the same substituents that ring W 1 and ring W 2 may have.
  • a ring formed by connecting R 5 and R 6 to each other is a ring containing a nitrogen atom as a component of the ring.
  • a ring formed by connecting R 5 and R 6 may contain a hetero atom other than a nitrogen atom as a component of the ring.
  • a ring formed by connecting R 5 and R 6 to each other may be a monocyclic ring or a condensed ring. Examples of the ring formed by connecting R 5 and R 6 include the same rings as those formed by connecting R 3 and R 4 to each other.
  • a hydrogen atom included in a ring formed by connecting R 5 and R 6 to each other may be substituted with an arbitrary substituent, and examples of the optional substituent include the same substituents as those of ring W 1 and ring W 2 .
  • each of R 3 , R 4 , R 5 and R 6 independently represents a hydrogen atom or a hydrocarbon group having 1 to 24 carbon atoms.
  • At least one selected from R 3 and R 4 is preferably a hydrocarbon group of 1 to 24 carbon atoms, more preferably an aromatic hydrocarbon group of 6 to 24 carbon atoms.
  • At least one selected from R5 and R6 is a C1 - C24 hydrocarbon group, and it is more preferable that it is a C6-C24 aromatic hydrocarbon group.
  • R 3 and R 4 are connected to each other to form a ring
  • R 5 and R 6 are connected to each other to form a ring.
  • the cation represented by formula (I-A) is preferably a cation represented by formula (I-B) or a cation represented by formula (I-C).
  • Each of ring W 1 , ring W 2 , R 1 and R 2 has the same meaning as described above.
  • Ar 1 and Ar 2 each independently represent an aromatic hydrocarbon group having 6 to 24 carbon atoms which may have a substituent.
  • R 4A and R 6A each independently represent a hydrogen atom or a hydrocarbon group having 6 to 24 carbon atoms which may have a substituent.
  • Ring W 3 and Ring W 4 each independently represent a nitrogen-containing heterocyclic group.
  • the aromatic hydrocarbon group having 6 to 24 carbon atoms represented by Ar 1 and Ar 2 includes the same aromatic hydrocarbon group represented by R 3 .
  • Ar 1 and Ar 2 are each independently preferably an aryl group having 6 to 24 carbon atoms, and more preferably an aryl group having 6 to 12 carbon atoms.
  • hydrocarbon groups having 6 to 24 carbon atoms represented by R 4A and R 6A include the same hydrocarbon groups represented by R 3 .
  • R 4A and R 6A are each independently preferably a hydrogen atom or an aliphatic hydrocarbon group having 1 to 24 carbon atoms, more preferably a hydrogen atom or an alkyl group having 1 to 24 carbon atoms, and preferably a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. More preferable
  • Substituents that Ar 1 , Ar 2 , R 4A and R 6A may have include substituents that the hydrocarbon group represented by R 3 may have.
  • the nitrogen-containing heterocyclic group represented by the ring W 3 and the ring W 4 may be a monocyclic ring or a condensed ring, preferably a condensed ring.
  • ring W 3 and ring W 4 are each independently an azetidine ring, a pyrrolidine ring, a piperidine ring, a morpholine ring, an imidazoline ring, a pyrazole ring, an imidazole ring, a triazole ring, a tetrazole ring, It is preferably a piperazine ring, a thiomorpholine ring, or an indoline ring.
  • the cation represented by formula (I-B) is preferably a cation represented by formula (I-B1), and the cation represented by formula (I-C) is preferably a cation represented by formula (I-C1).
  • Examples of cations containing a partial structure represented by formula (I) include cations described below.
  • Cations having a partial structure represented by formula (I) include formula (I-1), formula (I-2), formula (I-3), formula (I-4), formula (I-8), formula (I-12), Formula (I-13), Formula (I-17), Formula (I-18), Formula (I-23), Formula (I-25), Formula (I-26), Formula ( I-27), Formula (I-28), Formula (I-29), Formula (I-31), Formula (I-38), Formula (I-60), Formula (I-61), Formula (I -62), Formula (I-79), Formula (I-80), Formula (I-85), Formula (I-87), Formula (I-90), Formula (I-93), Formula (I- 94), Formula (I-95), Formula (I-96), Formula (I-101), Formula (I-103), Formula (I-105), Formula (I-107), Formula (I-128) ), a cation represented by formula (I-133), formula (I-135), formula (I-137), or formula (I-139) is preferred.
  • Compound (I) is usually composed of an anion paired with a cation represented by formula (I).
  • the combination of the cation and anion represented by Formula (I) of Compound (I) is not limited.
  • the valence of an anion is 2 or more, it can have a plurality of cations represented by formula (I).
  • the valence of an anion is 2 or more, it can have a cation other than the cation represented by Formula (I) and the cation represented by Formula (I).
  • the anion may be an organic anion or an inorganic anion.
  • organic anion examples include acetate anion, methide anion, amide anion, sulfonate anion, or borate anion, and methide anion, amide anion, sulfonate anion, or borate anion is preferable.
  • the methide anion is preferably an anion represented by formula (c-A).
  • R 1c , R 2c and R 3c each independently represent a monovalent substituent.
  • the monovalent substituent represented by R 1c , R 2c and R 3c is not particularly limited, but is fluorine atom; fluoroalkyl groups having 1 to 12 carbon atoms such as a monofluoromethyl group, a difluoromethyl group, a trifluoromethyl group, and a tetrafluoroethyl group; fluoroaryl groups having 6 to 18 carbon atoms, such as a monofluorophenyl group and a tetrafluorophenyl group; cyano group; nitro group; It is preferably -SO 2 -R 11c (R 11c represents a hydrocarbon group having 1 to 12 carbon atoms which may have a fluorine atom).
  • the amide anion is preferably an anion represented by formula (c-B).
  • R 4c and R 5c each independently represent a monovalent substituent.
  • the monovalent substituent represented by R 4c and R 5c is not particularly limited, but is fluorine atom; fluoroalkyl groups having 1 to 12 carbon atoms such as a monofluoromethyl group, a difluoromethyl group, a trifluoromethyl group, and a tetrafluoroethyl group; fluoroaryl groups having 6 to 18 carbon atoms, such as a monofluorophenyl group and a tetrafluorophenyl group; cyano group; nitro group; It is preferably -SO 2 -R 11c (R 11c represents a hydrocarbon group having 1 to 12 carbon atoms which may have a fluorine atom).
  • an anion represented by the formula (c-C) is preferable.
  • R 6c represents a monovalent substituent.
  • the monovalent substituent represented by R 6c is not particularly limited, but is fluorine atom; fluoroalkyl groups having 1 to 12 carbon atoms such as a monofluoromethyl group, a difluoromethyl group, a trifluoromethyl group, and a tetrafluoroethyl group; fluoroaryl groups having 6 to 18 carbon atoms, such as a monofluorophenyl group and a tetrafluorophenyl group; cyano group; nitro group; It is preferably -SO 2 -R 11c (R 11c represents a hydrocarbon group having 1 to 12 carbon atoms which may have a fluorine atom).
  • the borate anion is preferably an anion represented by formula (c-D).
  • R 7c , R 8c , R 9c and R 10c each independently represent a monovalent substituent.
  • the monovalent substituent represented by R 7c , R 8c , R 9c and R 10c is not particularly limited, but is fluorine atom; fluoroalkyl groups having 1 to 12 carbon atoms such as a monofluoromethyl group, a difluoromethyl group, a trifluoromethyl group, and a tetrafluoroethyl group; fluoroaryl groups having 6 to 18 carbon atoms, such as a monofluorophenyl group and a tetrafluorophenyl group; cyano group; nitro group; It is preferably -SO 2 -R 11c (R 11c represents a hydrocarbon group having 1 to 12 carbon atoms which may have a fluorine atom).
  • the anion represented by formula (c-A) is preferably an anion represented by formula (c-A1),
  • the anion represented by formula (c-B) is preferably an anion represented by formula (c-B1),
  • the anion represented by formula (c-C) is preferably an anion represented by formula (c-C1),
  • the anion represented by formula (c-D) is preferably an anion represented by formula (c-D1) or an anion represented by formula (c-D2).
  • Rf 1 , Rf 2 and Rf 3 each independently represent a fluoroalkyl group having 1 to 12 carbon atoms.
  • Rf 4 and Rf 5 each independently represent a fluorine atom or a fluoroalkyl group having 1 to 12 carbon atoms.
  • Rf 6 represents a fluoroalkyl group having 1 to 12 carbon atoms.
  • R 1d , R 2d , R 3d and R 4d each independently represent a fluorine atom or a fluoroalkyl group having 1 to 12 carbon atoms.
  • n1 to n4 each independently represent an integer of 0 to 5.
  • More specific organic anions include, for example, acetate anion [CH 3 COO - ], trifluoroacetate anion [CF 3 COO - ], methanesulfonate anion [CH 3 SO 3 - ], trifluoromethanesulfonate anion [CF 3 SO 3 - ], p-toluenesulfonate anion [p-CH 3 C 6 H 4 SO 3 - ], bis(trifluoromethanesulfonyl)imide anion [(CF 3 SO 2 ) 2 N - ], bis (Nonafluorobutylsulfonyl)imide anion [(C 4 F 9 SO 2 ) 2 N - ], tris(trifluoromethanesulfonyl)methanide anion [(CF 3 SO 2 ) 3 C - ], dimethyl Phosphinate anion [(CH 3 ) 2 POO - ], (poly)hydrofluorofluoride anion [
  • Inorganic anions include, for example, fluoride anion, chloride anion, bromide anion, iodide anion, tetrachloroaluminate anion [AlCl 4 - ], heptachlorodialuminate anion [Al 2 Cl 7 - ], tetrafluoroborate anion [BF 4 - ], hexafluorophosphate anion [PF 6 - ], perchlorate anion [ClO 4 - ], nitrate anion [NO 3 - ], hexafluoroarsenate anion [AsF 6 - ], hexafluoro Roantimonate anion [SbF 6 - ], hexafluoroniobate anion [NbF 6 - ], hexafluorotantalate anion [TaF 6 - ], dicyanamide anion [(CN) 2 N - ], bis( fluorosulfonyl)imi
  • the inorganic anion is preferably a bis(fluorosulfonyl)imide anion (N - (SO 2 F) 2 ).
  • organic anions include trifluoroacetate anion [CF 3 COO - ], trifluoromethanesulfonate anion [CF 3 SO 3 - ], bis(trifluoromethanesulfonyl)imide anion [(CF 3 SO 2 ) 2 N - ], tris (trifluoromethanesulfonyl)methanide anion [(CF 3 SO 2 ) 3 C - ], perfluorobutanesulfonate anion [C 4 F 9 SO 3 - ], bis(pentafluoro Roethanesulfonyl) imide anion [(C 2 F 5 SO 2 ) 2 N - ], perfluorobutanoate anion [C 3 F 7 COO - ], (trifluoromethanesulfonyl) (trifluoro
  • Compound (I) examples include compounds listed in Tables 1 to 8 below.
  • compound (1) in Table 1 is a compound containing a cation represented by formula (I-1) and a chloride anion, and is a compound described below.
  • Compound (I) includes compound (3), compound (39), compound (40), compound (41), compound (43), compound (45), compound (46), compound (47), compound (49), Compound (53), Compound (55), Compound (56), Compound (57), Compound (58), Compound (59), Compound (60), Compound (65), Compound (66), Compound (67), Compound (70), Compound (72), Compound (75), Compound (115), Compound (116), Compound (117), Compound (119), Compound (121), Compound (122), Compound (123), Compound (125), Compound (129), Compound (131), Compound (132), Compound (133), Compound (134), Compound (135), Compound (136), Compound (141), Compound (142), Compound (143), Compound (146), Compound (148), Compound (151), Compound (153), Compound (154), Compound (155), Compound (157), Compound (159), Compound (160), Compound (161), Compound (163), Compound (
  • the cation containing the partial structure represented by formula (I) of compound (I) is represented by the compound represented by formula (M) (hereinafter sometimes referred to as compound (M)) and formula (b-1) It can be produced by reacting a compound (hereinafter sometimes referred to as compound (b-1)) with a compound represented by formula (b-2) (hereinafter sometimes referred to as compound (b-2)). .
  • ring W 1 , ring W 2 , R 1 , R 2 , R 3 , R 4 , R 5 and R 6 respectively represent the same meanings as above.
  • reaction of compound (M) with compound (b-1) and compound (b-2) is preferably carried out in the presence of a catalyst.
  • the catalyst examples include carboxylic acids such as formic acid, acetic acid, and trifluoroacetic acid; ammonium chloride; Lewis acids such as titanium tetrachloride, aluminum chloride, aluminum isopropoxide, boron tribromide, boron trifluoride, iron chloride, gallium chloride, tin tetrachloride, and lanthanoid triflate; sulfonic acid anhydrides such as methanesulfonic acid anhydride, p-toluenesulfonic acid anhydride, trifluoromethanesulfonic acid anhydride, and nonafluorobutanesulfonic acid anhydride; sulfonic acids such as p-toluenesulfonic acid, trifluoromethanesulfonic acid, and fluorosulfuric acid; electrophilic alkylating agents such as dimethyl sulfuric acid, methyl triflate, iodomethane, trimethyloxon
  • the amount of the catalyst used is usually 0.001 to 10 moles, preferably 0.05 to 2 moles, per mole of the compound (M).
  • reaction of compound (M) with compound (b-1) and compound (b-2) is preferably carried out in the presence of a base.
  • Bases include metals such as sodium methoxide, potassium methoxide, lithium methoxide, sodium ethoxide, potassium ethoxide, lithium ethoxide, sodium isopropoxide, sodium tert-butoxide, and potassium tert-butoxide.
  • alkoxides preferably alkali metal alkoxides and the like
  • metal hydroxides such as lithium hydroxide, sodium hydroxide and potassium hydroxide
  • metal hydrides such as sodium hydride, potassium hydride, lithium aluminum hydride and sodium borohydride
  • Metal carbonates such as sodium carbonate, sodium hydrogencarbonate, potassium carbonate, potassium hydrogencarbonate, lithium carbonate, lithium hydrogencarbonate, and cesium carbonate
  • organolithium compounds such as methyllithium, n-butyllithium, sec-butyllithium, tert-butyllithium, and phenyllithium
  • Alkyl metal halides such as methyl magnesium bromide, isopropyl magnesium bromide, n-butyl magnesium bromide, and isopropyl magnesium chloride
  • metal amide compounds such as lithium diisopropylamide, lithium 2,2,6,6-tetramethylpiperidide, lithium (bistrimethylsilyl)amide, and lithium tetramethyl
  • the amount of base used is usually 0.1 to 10 moles, preferably 0.5 to 2 moles, per mole of the compound (M).
  • reaction of compound (M), compound (b-1) and compound (b-2) can be carried out in the presence of a solvent.
  • the solvent examples include nitrile solvents such as acetonitrile and benzonitrile; aromatic hydrocarbon solvents such as benzene, toluene, xylene, and anisole; aliphatic hydrocarbon solvents such as n-hexane, n-heptane, cyclohexane, and methylcyclohexane; halogen solvents such as chlorobenzene, orthodichlorobenzene, metadichlorobenzene, paradichlorobenzene, dichloromethane, dichloroethane, tetrachloroethane, tetrachloroethylene, and chloroform; ester solvents such as methyl acetate, ethyl acetate, butyl acetate, isobutyl acetate, and normal propyl acetate; alcohol solvents such as methanol, ethanol, isopropanol, hexafluoroisopropanol, n
  • the solvent is preferably a nitrile solvent, a ketone solvent, or an aromatic hydrocarbon solvent, and more preferably acetonitrile, toluene, methyl ethyl ketone, or methyl isobutyl ketone.
  • the amount of the solvent used is usually 0.5 to 1000 parts by mass, preferably 1 to 10 parts by mass, per 1 part by mass of the compound (M).
  • reaction of compound (M), compound (b-1) and compound (b-2) is carried out by mixing compound (M), compound (b-1) and compound (b-2).
  • compound (M), compound (b-1) and compound (b-2) it is preferable to add compound (b-1) and compound (b-2) to a mixture of compound (M), base and catalyst. .
  • the amount of compound (b-1) used is usually 0.1 to 20 moles, preferably 0.5 to 4 mole equivalents, per mole of compound (M).
  • the amount of compound (b-2) used is usually 0.1 to 20 moles, preferably 0.5 to 4 mole equivalents, per mole of compound (M).
  • reaction time of compound (M), compound (b-1) and compound (b-2) is usually 0.1 to 100 hours.
  • reaction temperature of compound (M), compound (b-1) and compound (b-2) is usually -80 to 200 ⁇ .
  • Examples of the compound (b-1) and the compound (b-2) include aziridine, azetidine, pyrrolidine, piperidine, morpholine, thiomorpholine, indoline, methylindoline, nitroindoline, and aminobiphenyl. , cyanoaminobiphenyl, nitroaminobiphenyl, methoxyaminobiphenyl, etc. are mentioned.
  • Examples of the compound (M) include compounds described below.
  • Compound (M) is a compound represented by formula (M1-1) (hereinafter sometimes referred to as compound (M1-1)) or a compound represented by formula (M1-2) (hereinafter referred to as compound (M1-2) ) and a compound represented by formula (M1-3) (hereinafter sometimes referred to as compound (M1-3)).
  • ring W 1 , ring W 2 , R 1 and R 2 represent the same meanings as above.
  • E 1 and E 2 each independently represent a leaving group.
  • the leaving groups represented by E 1 and E 2 are each independently a halogen atom, a succinimide group, a maleimide group, saccharin, a methylsulfonyl group, a p-methoxybenzenesulfonyl group, a p-toluenesulfonyl group, and a trifluoromethylsulfonyl group.
  • a yl group, a nonafluorobutanesulfonyl group, etc. are mentioned.
  • reaction of compound (M1-1), compound (M1-2) and compound (M1-3) is preferably carried out in the presence of a base.
  • Examples of the base include the same bases used for the reaction between compound (M), compound (b-1) and compound (b-2), metal alkoxides, metal hydroxides, metal hydrides, metal carbonates, organic It is preferably lithium, a metal amide compound, an amine compound or a metal carboxylate, potassium ethoxide, sodium tertiary butoxide, potassium tertiary butoxide, sodium hydroxide, potassium hydroxide, sodium hydride, lithium aluminum hydride, sodium carbonate, carbonate Sodium hydrogen carbonate, potassium carbonate, potassium hydrogen carbonate, methyl lithium, normal butyl lithium, tertiary butyl lithium, lithium diisopropylamide, lithium 2,2,6,6-tetramethylpiperidide, lithium (bistrimethylsilyl)amide , lithium tetramethylpiperidide, pyridine, 2,6-dimethylpyridine, 2,6-ditertiarybutylpyridine, triethylamine, diisopropylethylamine,
  • the amount of the base used is usually 0.001 to 20 moles, preferably 0.1 to 10 moles, per mole of the compound (M1-1).
  • the reaction of compound (M1-1), compound (M1-2) and compound (M1-3) can be carried out in the presence of a solvent.
  • a solvent include the same solvents usable in the reaction of compound (M), compound (b-1) and compound (b-2). Preferred are acetonitrile, methanol, ethanol, toluene, 2-butanone, dioxane, tetrahydrofuran, dimethylsulfoxide, dimethylformamide and dimethylacetamide.
  • the solvent is preferably a dehydration solvent.
  • reaction of compound (M1-1), compound (M1-2) and compound (M1-3) is carried out by mixing compound (M1-1), compound (M1-2) and compound (M1-3), and a base , It is preferably carried out by mixing the compound (M1-1), the compound (M1-2) and the compound (M1-3).
  • the reaction of the compound (M1-1), the compound (M1-2) and the compound (M1-3) is preferably carried out in a deoxygenated atmosphere (for example, a nitrogen atmosphere).
  • a deoxygenated atmosphere for example, a nitrogen atmosphere.
  • the amount of compound (M1-2) used is usually 0.1 to 20 moles, preferably 0.5 to 10 moles, per mole of compound (M1-1).
  • the amount of compound (M1-3) used is usually 0.1 to 20 moles, preferably 0.5 to 10 moles, per mole of compound (M1-1).
  • the amount of the base used is usually 0.001 to 20 mol, preferably 0.1 to 10 mol, per 1 mol of the compound (M1-1).
  • reaction time of compound (M1-1), compound (M1-2) and compound (M1-3) is usually 0.1 to 200 hours.
  • reaction temperature of compound (M1-1), compound (M1-2) and compound (M1-3) is usually -100 to 200 ⁇ .
  • compound (M1-1) a commercial item can also be used, and 7-hydroxy-2,3,4,4a,5,6-hexahydronaphthalen-2-one etc. are mentioned.
  • a commercial item can also be used as compound (M1-2) and compound (M1-3).
  • compound (M), compound (b-1), and compound (b-2) are reacted in the presence of a base, compound (I) containing an anion derived from a base and a cation represented by formula (I-A) can be obtained. .
  • ion exchange may be performed by mixing Compound (I) with a salt having a desired anion.
  • the ion exchange may be performed in the presence of a solvent.
  • salts having desired anions include lithium salts, sodium salts, potassium salts, cesium salts, barium salts, calcium salts, magnesium salts, and ammonium salts.
  • the present invention also includes compositions containing Compound (I).
  • composition containing compound (I) can be used for all applications, but can be particularly suitably used for applications that may be exposed to light including sunlight or ultraviolet rays.
  • Specific examples include, for example, glass substitutes and surface coatings thereof; Coating materials for window glass, skylight glass, and light source protection glass of dwellings, facilities, transportation equipment, etc.; window films for dwellings, facilities, transportation devices, etc.; paints for interior and exterior materials and interior and exterior decorations of dwellings, facilities, transportation equipment, etc., and coating films formed by the paints; alkyd resin lacquer paints and coating films formed by the paints; acrylic lacquer paint and a coating film formed by the paint; members for light sources emitting ultraviolet rays such as fluorescent lamps and mercury lamps; Materials for blocking electromagnetic waves generated from precision instruments, members for electronic and electrical devices, and various displays; Containers or packaging materials for food, chemicals, medicines, etc.; Bottles, boxes, blisters, cups, special packaging, compact disc coats, sheet or film materials for agriculture and industry; fading inhibitors such as prints, dyes
  • a composition containing Compound (I) may be a resin composition containing Compound (I) and a resin (hereinafter sometimes referred to as “resin composition”) or a composition containing Compound (I) and a polymerizable monomer (hereinafter referred to as “composition”). (1) It is sometimes referred to as “.) is preferable.
  • thermoplastic resins and thermosetting resins conventionally used in the manufacture of various molded articles, sheets, and films known in the art.
  • thermoplastic resin examples include olefin-based resins such as polyethylene resin, polypropylene resin, and polycycloolefin resin, poly(meth)acrylic acid ester-based resin, polystyrene-based resin, styrene-acrylonitrile-based resin, and acrylonitrile-butadiene-styrene.
  • olefin-based resins such as polyethylene resin, polypropylene resin, and polycycloolefin resin
  • poly(meth)acrylic acid ester-based resin polystyrene-based resin
  • styrene-acrylonitrile-based resin examples include acrylonitrile-butadiene-styrene.
  • polyvinyl chloride based resin polyvinylidene chloride based resin
  • polyvinyl acetate based resin polyvinyl butyral based resin
  • ethylene-vinyl acetate based copolymer ethylene vinyl alcohol based resin
  • polyethylene terephthalate resin polybutylene polyester resins such as terephthalate resins and liquid crystal polyester resins, polyacetal resins, polyamide resins, polycarbonate resins, polyurethane resins, and polyphenylene sulfide resins; and the like.
  • These resins may be used as one type or a polymer blend or polymer alloy of two or more types.
  • thermosetting resin examples include epoxy resins, melamine resins, unsaturated polyester resins, phenol resins, urea resins, alkyd resins, and thermosetting polyimide resins.
  • the shape of the polymer molded article (molded article) formed from the resin composition may be any shape such as flat film, powder, spherical particle, crushed particle, bulky continuum, fibrous, tubular, hollow fiber, granular, plate, porous, etc. there is.
  • the resin composition is used as a UV absorbing filter or a UV absorbing film
  • the resin is preferably a transparent resin.
  • the resin composition can be obtained by mixing Compound (I) and a resin.
  • Compound (I) may be contained in an amount necessary for imparting desired performance, for example, from 0.00001 to 99 parts by mass with respect to 100 parts by mass of the resin.
  • the resin composition may contain other additives such as a solvent, a crosslinking catalyst, a tackifier, a plasticizer, a softener, a dye, a pigment, an inorganic filler, and the like, if necessary.
  • additives such as a solvent, a crosslinking catalyst, a tackifier, a plasticizer, a softener, a dye, a pigment, an inorganic filler, and the like, if necessary.
  • the polymerizable monomer used in the composition (1) is not particularly limited, but is preferably a radically polymerizable monomer, more preferably an optical radically polymerizable monomer, and still more preferably a (meth)acrylate.
  • Examples of the (meth)acrylate include a monofunctional (meth)acrylate monomer having one (meth)acryloyloxy group in the molecule, and a bifunctional (meth)acrylate monomer having two (meth)acryloyloxy groups in the molecule. , polyfunctional (meth)acrylate monomers having three or more (meth)acryloyloxy groups in the molecule.
  • the composition (1) further contains a polymerization initiator.
  • the polymerization initiator is preferably a radical polymerization initiator, and more preferably a photopolymerization initiator.
  • Composition (1) can be obtained by mixing compound (I) and a polymerizable monomer.
  • Compound (I) may be contained in an amount necessary for imparting desired performance, for example, 0.01 to 20 parts by mass or the like per 100 parts by mass of the polymerizable monomer.
  • the composition 1 may contain other additives such as a solvent, a crosslinking catalyst, a tackifier, a plasticizer, a softener, a dye, a pigment, an inorganic filler, and the like, if necessary.
  • additives such as a solvent, a crosslinking catalyst, a tackifier, a plasticizer, a softener, a dye, a pigment, an inorganic filler, and the like, if necessary.
  • the present invention includes an optical layer containing a cation comprising a partial structure represented by formula (I).
  • An optical layer containing a cation containing a partial structure represented by formula (I) is usually formed from an optical layer containing compound (I).
  • the optical layer containing compound (I) can be laminated on, for example, a display element such as an organic EL element or a liquid crystal cell and used for an image display device (FPD: Flat Panel Display) such as an organic EL display device or a liquid crystal display device.
  • the optical layer can be formed using the resin composition of the present invention.
  • the optical layer formed from the resin composition of the present invention may be applied to any of a film layer, an adhesive layer, a coating layer, and the like, and is preferably an adhesive layer or a coating layer.
  • the optical layer containing compound (I) is preferably formed from the resin composition or composition (1) described above.
  • the optical layer containing compound (I) may consist of only the optical layer containing compound (I), or may be an optical laminate in which a layer containing compound (I) and other layers are laminated.
  • Other layers include, for example, a polarizing film (polarizer), a retardation film, a thermoplastic resin film, a wavelength conversion layer, and the like. If the optical laminate is a laminate in which the optical layer, adhesive agent layer, and polarizing film of the present invention are laminated in this order, the optical layer of the present invention is preferably an optical layer (optical film) formed from a resin composition.
  • the optical layer of the present invention is preferably an optical layer (coating layer) formed from the composition (1).
  • the optical layer of the present invention is preferably an optical layer (adhesive layer) formed from a resin composition. In the case of laminating the optical layer of the present invention and the wavelength conversion layer, it is preferable that the optical layer of the present invention is disposed on the viewing side more than the wavelength conversion layer.
  • the pressure-sensitive adhesive composition (1) containing the resin (A), the compound (I), the crosslinking agent (B) and the silane compound (C) (hereinafter referred to as the pressure-sensitive adhesive composition (1)) It is formed from The pressure-sensitive adhesive composition (1) further includes a radical curable component (D), an initiator (E), a light absorbing compound (F) other than the compound (I) (hereinafter sometimes referred to as a photoselective absorbing compound (F)), an electrical charge. It may contain an inhibitor, etc., and it is preferable to include at least one selected from the group consisting of a radical curable component (D), an initiator (E), and a photoselective absorption compound (F).
  • Resin (A) is not particularly limited as long as it is a resin used for the pressure-sensitive adhesive composition. It is preferable that the resin (A) does not show maximum absorption in the wavelength range of 300 nm to 780 nm.
  • Resin (A) is preferably a resin having a glass transition temperature (Tg) of 40°C or less.
  • the glass transition temperature (Tg) of the resin (A) is more preferably 20°C or lower, still more 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 or higher, still more preferably -55°C or higher, particularly -50°C or higher. desirable.
  • 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 (1) to the adherend.
  • the glass transition temperature of resin (A) is -80 degreeC or more, it is advantageous to improve the durability of the adhesive layer formed from the adhesive composition (1).
  • the glass transition temperature can be measured by a differential scanning calorimeter (DSC).
  • Examples of the resin (A) include (meth)acrylic resins, silicone resins, rubber resins, urethane resins, and the like, and (meth)acrylic resins are preferred.
  • the (meth)acrylic resin is preferably a polymer containing a structural unit derived from (meth)acrylic acid ester as a main component (preferably containing 50% by mass or more).
  • the (meth)acrylic resin may include structural units derived from monomers other than one or more (meth)acrylic acid esters (for example, structural units derived from monomers having polar functional groups such as hydroxyl groups, carboxyl groups, and amino groups).
  • the content of the resin (A) is usually 50% by mass to 99.9% by mass, preferably 60% by mass to 95% by mass, more preferably 70% by mass to 90% by mass, based on 100% by mass of the solid content of the pressure-sensitive adhesive composition (1). %to be.
  • the content of compound (I) is usually 0.01 to 20 parts by mass, preferably 0.1 to 20 parts by mass, more preferably 0.2 to 10 parts by mass, particularly preferably 0.5 to 5 parts by mass, based on 100 parts by mass of the resin (A). is the mass part.
  • crosslinking agent (B) examples include isocyanate-based crosslinking agents, epoxy-based crosslinking agents, aziridine-based crosslinking agents, metal chelate-based crosslinking agents, and the like, and in particular, isocyanate-based crosslinking agents are preferred from the viewpoint of the pot life of the pressure-sensitive adhesive composition, durability of the pressure-sensitive adhesive layer, and crosslinking rate. desirable.
  • the content of the crosslinking agent (B) is usually 0.01 to 25 parts by mass, preferably 0.1 to 15 parts by mass, more preferably 0.15 to 7 parts by mass, still more preferably 0.2 to 5 parts by mass, based on 100 parts by mass of the resin (A). It is a mass part, It is 0.25-2 mass parts especially preferably.
  • silane compound (C) examples include vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris(2-methoxyethoxy)silane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropyltrie Toxysilane, 3-glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropylethoxydimethylsilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3-chloropropylmethyldimethoxysilane , 3-chloropropyltrimethoxysilane, 3-methacryloyloxypropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, etc. are mentioned.
  • 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, more preferably 0.15 to 7 parts by mass, still more preferably 0.2 to 20 parts by mass, based on 100 parts by mass of the resin (A). 5 parts by mass, 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 (1) may contain two or more kinds of radical curable components (D).
  • the (meth)acrylate-based compound a (meth)acrylate monomer having at least one (meth)acryloyloxy group in a molecule, a (meth)acrylamide monomer, and at least two (meth)acryloyl groups in a molecule and (meth)acryloyl group-containing compounds such as (meth)acrylic oligomers having.
  • the (meth)acrylic oligomer is preferably a (meth)acrylate oligomer having at least two (meth)acryloyloxy groups in the molecule.
  • a (meth)acrylate-type compound can be used individually by 1 type, and may use 2 or more types together.
  • Examples of the (meth)acrylate monomer include 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. Monofunctional (meth)acrylate monomers having three or more (meth)acryloyloxy groups in the molecule are exemplified.
  • it is a (meth)acrylate compound, and it is more preferable that it is a polyfunctional (meth)acrylate compound. It is preferable that the polyfunctional (meth)acrylate compound is more than trifunctional.
  • the content of the radical curable component (D) is usually 0.5 to 100 parts by mass, preferably 1 to 70 parts by mass, more preferably 3 to 50 parts by mass, and 5 to 30 parts by mass relative to 100 parts by mass of the resin (A). It is more preferable that it is negative, and it is particularly preferable that it is 7.5 to 25 parts by mass.
  • the initiator (E) may be either a compound that causes a polymerization reaction by absorbing heat energy (thermal polymerization initiator) or a compound that causes a polymerization reaction by absorbing light energy (photopolymerization initiator).
  • the light herein is preferably an active energy ray such as visible light, ultraviolet rays, X-rays, or electron beams.
  • thermal polymerization initiator examples include compounds that generate radicals by heating (thermal radical generators), compounds that generate acids by heating (thermal acid generators), compounds that generate bases by heating (thermal base generators), and the like. can be heard
  • Photopolymerization initiators include compounds that generate radicals by absorbing light energy (photoradical generators), compounds that generate acids by absorbing light energy (photoacid generators), and compounds that generate bases by absorbing light energy. (Photo base generator) etc. are mentioned.
  • the initiator (E) is preferably selected from those suitable for the polymerization reaction of the above-described radical curable component (D), preferably a radical polymerization initiator, and more preferably an optical radical polymerization initiator.
  • radical polymerization initiator examples include alkylphenone compounds, benzoin compounds, benzophenone compounds, oxime ester compounds, and phosphine compounds.
  • the radical polymerization initiator is preferably an optical radical polymerization initiator, and more preferably an oxime ester-based radical optical polymerization initiator from the viewpoint of the reactivity of the polymerization reaction.
  • an oxime ester-based radical photopolymerization initiator By using an oxime ester-based radical photopolymerization initiator, the reaction rate of the radical curing component (D) can be increased even under curing conditions where the intensity of illumination or the amount of light is low.
  • the content of the initiator (E) is usually 0.01 to 20 parts by mass, preferably 0.3 to 10 parts by mass, more preferably 0.5 to 5 parts by mass, and 0.75 to 4 parts by mass relative to 100 parts by mass of the resin (A). More preferably, it is 1 to 3 parts by mass particularly preferably.
  • the light-selective absorbing compound (F) is a light-absorbing compound other than compound (I), for example, a compound (ultraviolet absorber) that absorbs light of a wavelength of 250 nm to 380 nm (preferably a wavelength of 250 nm or more and a wavelength of less than 360 nm) , A compound (dye) that absorbs a wavelength of 380 to 780 nm, or a compound (infrared absorber) that absorbs a wavelength of 780 nm to 1500 nm.
  • a compound (ultraviolet absorber) that absorbs light of a wavelength of 250 nm to 380 nm (preferably a wavelength of 250 nm or more and a wavelength of less than 360 nm)
  • a compound (dye) that absorbs a wavelength of 380 to 780 nm or a compound (infrared absorber) that absorbs a wavelength of 780 nm to 1500 nm.
  • the structure of the ultraviolet absorber is not particularly limited as long as it is a compound that absorbs light with a wavelength of 250 nm to 380 nm, but benzotriazole-based compounds, benzophenone-based compounds, triazine-based compounds, salicylic acid-based compounds, cyanoacrylate-based compounds, Compounds, such as a benzoxazine type compound, etc. are preferable.
  • the content of the photoselective absorbing compound (F) is usually 0.1 to 50 parts by mass, preferably 0.2 to 40 parts by mass, more preferably 0.5 to 30 parts by mass, and still more preferably based on 100 parts by mass of the resin (A). 1 to 25 parts by mass, particularly preferably 2 to 20 parts by mass.
  • the present invention includes dyes (eg, textiles, films, resins, etc.) dyed with Compound (I).
  • Dyeing with Compound (I) is performed, for example, by immersing articles such as fibers, films, and resins in a solution obtained by dissolving Compound (I) in a solvent.
  • a 2-butanone solution (0.003 g/L) of the compound represented by the obtained formula (1) was placed in a 1 cm quartz cell, and the quartz cell was set in a spectrophotometer UV-2450 (manufactured by Shimadzu Seisakusho Co., Ltd.). Absorbance was measured in the wavelength range of 300 to 800 nm for each 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 Formula (1) in the solution, and the optical path length of the quartz cell.
  • ⁇ ( ⁇ ) represents the gram extinction coefficient (L/(g cm)) of the compound represented by formula (1) at a wavelength of ⁇ nm
  • A( ⁇ ) represents the absorbance at a wavelength of ⁇ nm
  • C represents the concentration (g/L)
  • L represents the optical path length (m) of the quartz cell.
  • the maximum absorption wavelength of the obtained compound represented by Formula (1) was 509 nm.
  • the gram extinction coefficient ⁇ ( ⁇ max) at the maximum absorption wavelength of the compound represented by the obtained formula (1) was 52 L/(g ⁇ cm).
  • 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 as a solvent was injected into a reaction vessel equipped with a cooling pipe, a nitrogen inlet pipe, a thermometer and a stirrer, and nitrogen gas
  • the air in the apparatus was purged with a furnace to make it free of oxygen, while raising the internal temperature to 55°C.
  • a solution in which 0.14 parts of azobisisobutyronitrile (polymerization initiator) was dissolved in 10 parts of ethyl acetate was added in whole amount.
  • the temperature was maintained at this temperature for 1 hour after addition of the initiator, and then ethyl acetate was continuously added into the reaction vessel at an addition rate of 17.3 parts/hr while maintaining the internal temperature at 54 to 56° C., at which point the acrylic resin concentration reached 35%.
  • the addition of ethyl acetate was stopped, and the mixture was kept warm at this temperature until 12 hours elapsed from the start of addition of ethyl acetate.
  • ethyl acetate was added to adjust the concentration of the acrylic resin to 20% to prepare an ethyl acetate solution of the acrylic resin.
  • the obtained acrylic resin had a weight average molecular weight Mw of 1,400,000 and Mw/Mn of 5.5 in terms of polystyrene by GPC. Let this be an acrylic resin (A1).
  • a crosslinking agent manufactured by Tosoh Corporation: trade name "Coronate L", isocyanate compound, solid content 75%)
  • silane A resin composition by mixing 0.28 part of a compound (manufactured by Shin-Etsu Chemical Industry Co., Ltd.: trade name "KBM3066") and 0.5 part of a compound represented by formula (1), and further adding 2-butanone so that the solid content concentration is 14% (1) (Adhesive composition) was obtained.
  • the blending amount of the crosslinking agent is the number of parts by mass as an active ingredient.
  • resin composition (2) and resin composition (3) were produced in the same manner as in Example 2, except that each component and the content of each component were changed.
  • the mixing amount of the crosslinking agent is the number of parts by mass as an active ingredient, and the number of parts by mass of the solid content of the resin (A).
  • Example comparative example 2 3 One Resin composition No. One 2 3 Resin (A) (A1) 100 100 100 Compound (I) Equation (1) 0.5 1.0 cross-linking agent Coronate L 0.5 0.5 0.5 0.5 silane compound KBM3066 0.28 0.28 0.28 Formula (B) 1.0
  • Acrylic resin (A1) Acrylic resin (A1) synthesized in Polymerization Example 1
  • Coronate L manufactured by Tosoh Corporation, trade name: Coronate L, isocyanate-based crosslinking agent
  • KBM3066 manufactured by Shin-Etsu Chemical Industry Co., Ltd., trade name: KBM3066, silane coupling agent
  • Formula (B) A compound represented by the following formula (B) synthesized with reference to the specification of US Patent No. 6004536 (3-butyl-2-[3-(-3-butyl-5-phenyl-2(3H)- benzolylidene)-1-propen-1-yl]-5-phenyl-benzoxazolium p-toluenesulfonate), and the full width at half maximum determined in the same manner as described above was 44 nm.
  • the obtained resin composition (1) was applied using an applicator to the release-treated surface of a separate film made of a polyethylene terephthalate film subjected to release treatment [trade name "PLR-382190” obtained from Lintec Co., Ltd.], and then at 100 ° C. It was dried for 1 minute to prepare a resin molded body (adhesive layer) (1).
  • the thickness of the obtained resin molded body 1 was 20 ⁇ m.
  • a separate film was further laminated on one side of the obtained resin molded body (1) to obtain an adhesive layer with double-sided separate films.
  • the obtained resin layer 1 with double-sided separation films was stored under air at a temperature of 23 to 25°C for one month.
  • the presence or absence of crystal precipitation of the in-plane compound was confirmed using a microscope for the resin molded body 1 with the double-sided separation film after storage.
  • the case without crystal precipitation was designated as a
  • the case with crystal precipitation was designated as b.
  • Table 10 shows the evaluation results.
  • a polarizing plate in which a cycloolefin film having a thickness of 13 ⁇ m was bonded to one side of a polarizer having a thickness of 8 ⁇ m using an adhesive layer was prepared.
  • the obtained laminate (1-1) was put into a Sunshine Weather Meter (manufactured by Suga Scientific Instruments Co., Ltd.) for 75 hours at a temperature of 63°C and a relative humidity of 50% RH to conduct a weather resistance test.
  • the absorbance of the extracted laminate (1-1) was measured in the same manner as above. From the measured absorbance, the absorbance retention of the sample at a wavelength of 500 nm was determined based on the following formula. The results are shown in Table 10. The closer the absorbance retention ratio is to 100, the better the weather resistance without deterioration of the light selective absorption function.
  • the absorption wavelength for evaluating the absorbance retention rate a wavelength at which the absorbance becomes 1 to 1.5 on the long wavelength side of the maximum absorption wavelength among the measured absorbances was selected. This is because the wavelength is the most sensitive absorbance region in terms of measurement accuracy of the spectroscopic measuring device.
  • a (500) represents the absorbance of the laminate (1-1).
  • the resin composition (3) instead of the resin composition (1), the resin molded body (3) and the laminated body (3-1) were produced and evaluated in the same manner. In addition, the absorbance retention rate was evaluated at a wavelength of 510 nm. The results are shown in Table 10.
  • the compounds of the present invention have high absorption selectivity for light near the maximum absorption wavelength.
  • the resin composition containing the compound of the present invention has a high absorbance retention even after a weather resistance test, and thus has good weather resistance.
  • An object of the present invention is to provide a novel compound that efficiently absorbs light in the visible light region (wavelength 400 nm to wavelength 750 nm, preferably wavelength 450 nm to wavelength 600 nm) and at the same time has good weather resistance.

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Abstract

The objective of the present invention is to provide a novel compound effectively absorbing light in a visible light range and, simultaneously, having excellent weather resistance. The present invention provides: a compound, which has cations comprising a partial structure represented by formula (I); a composition comprising same; a molded product; a dyed product; and an optical layer.

Description

화합물과, 이를 포함하는 조성물, 성형체, 염색물 및 광학층Compounds, compositions containing them, molded articles, dyes and optical layers
본 발명은 화합물과, 이를 포함하는 조성물, 성형체, 염색물 및 광학층에 관한 것이다.The present invention relates to a compound and a composition, a molded article, a dye and an optical layer containing the compound.
가시광의 빛을 흡수하는 색소 화합물은 물체의 착색이나 특정 파장의 빛의 투과 또는 흡수 등의 목적으로 섬유, 잉크, 도료, 용기, 포장재, 인쇄물, 광학 물품, 안경, 표시장치 등의 폭넓은 용도로 사용되고 있다. 색소 화합물의 중요한 특성으로서 선택 흡수성(흡수 스펙트럼의 샤프니스) 및 내구성(특히 내후성)을 들 수 있다. 색소 화합물 중에서도 시아닌 색소는 폴리메틴 골격 중 메틴 탄소수를 컨트롤함으로써 파장 380 nm 이하의 자외선 영역에서 파장 780 nm 이상의 근적외선 영역까지 폭넓게 극대 흡수를 나타내는 파장을 컨트롤할 수 있는 점, 또한 시아닌 색소의 대다수는 비교적 높은 선택 흡수성을 나타내는 점에서 널리 사용되어 왔다(예컨대 미국특허 제6004536호).Pigment compounds that absorb visible light are used in a wide range of applications such as textiles, inks, paints, containers, packaging materials, prints, optical products, glasses, and display devices for the purpose of coloring objects or transmitting or absorbing light of a specific wavelength. It is being used. As important characteristics of a dye compound, selective absorption (absorption spectrum sharpness) and durability (particularly weather resistance) are mentioned. Among the pigment compounds, the cyanine pigment can control the wavelength showing maximum absorption in a wide range from the ultraviolet region with a wavelength of 380 nm or less to the near-infrared region with a wavelength of 780 nm or more by controlling the number of methine carbon atoms in the polymethine skeleton. It has been widely used in that it exhibits high selective absorption (for example, US Patent No. 6004536).
그런데 시아닌 색소는 높은 선택 흡수성을 갖기는 하나 내구성(그 중에서도 내후성)이 떨어지는 것이 많아 양호한 내구성을 갖는 화합물이 요구되고 있다.By the way, cyanine dyes have high selective absorption but have poor durability (particularly, weather resistance), so a compound having good durability is required.
본 발명은 이하의 발명을 포함한다.The present invention includes the following inventions.
[1]　하기 식 (I)로 표시되는 부분 구조를 포함하는 양이온을 포함하는 화합물.[1] A compound containing a cation containing a partial structure represented by formula (I) below.
[화학식 1][Formula 1]
Figure PCTKR2022010249-appb-I000001
Figure PCTKR2022010249-appb-I000001
[식 (I) 중,[In Formula (I),
고리 W1 및 고리 W2는 각각 독립적으로 적어도 하나의 이중 결합을 고리의 구성 요소로 갖는 고리 구조를 나타낸다.Ring W 1 and ring W 2 each independently represent a ring structure having at least one double bond as a ring component.
고리 W1 및 고리 W2는 각각 독립적으로 치환기를 가질 수 있다.Ring W 1 and ring W 2 may each independently have a substituent.
R1 및 R2는 각각 독립적으로 수소 원자 또는 1가의 치환기를 나타내고, R1 및 R2 중 적어도 한쪽은 1가의 치환기이다.]R 1 and R 2 each independently represent a hydrogen atom or a monovalent substituent, and at least one of R 1 and R 2 is a monovalent substituent.]
[2]　[1]에 있어서, R1 및 R2에서 선택되는 적어도 하나가 전자 흡인성기인 화합물.[2] The compound according to [1], wherein at least one selected from R 1 and R 2 is an electron-withdrawing group.
[3]　[2]에 있어서, R1 및 R2에서 선택되는 적어도 하나가 시아노기, 니트로기, 할로겐화알킬기, 할로겐화아릴기, -CO-R1, -CO-O-R2, -CO-NR3R3k, -CO-S-R4, -CS-R5, -CS-O-R6, -CS-S-R7, -SO-R8, -SO2-R9(R1, R2, R3, R3k, R4, R5, R6, R7, R8 및 R9는 각각 독립적으로 치환기를 가질 수 있는 탄화수소기 또는 할로겐 원자를 나타낸다.), -OCF3, -SCF3, -SF5, -SF3, -SO2H 또는 -SO3H인 화합물.[3] The method of [2], wherein at least one selected from R 1 and R 2 is a cyano group, a nitro group, a halogenated alkyl group, a halogenated aryl group, -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 independently represent a hydrocarbon group which may have a substituent or a halogen atom), -OCF 3 , -SCF 3 , -SF 5 , A compound that is -SF 3 , -SO 2 H or -SO 3 H.
[4]　[3]에 있어서, R1 및 R2에서 선택되는 적어도 하나가 시아노기인 화합물.[4] The compound according to [3], wherein at least one selected from R 1 and R 2 is a cyano group.
[5]　[1] 내지 [4] 중 어느 하나에 있어서, 식 (I)로 표시되는 부분 구조를 포함하는 양이온이 식 (I-A)로 표시되는 양이온인 화합물.[5] The compound according to any one of [1] to [4], wherein the cation containing the partial structure represented by formula (I) is a cation represented by formula (I-A).
[화학식 2][Formula 2]
Figure PCTKR2022010249-appb-I000002
Figure PCTKR2022010249-appb-I000002
[식 (I-A) 중,[In Formula (I-A),
고리 W1, 고리 W2, R1 및 R2는 각각 상기와 동일한 의미를 나타낸다.Each of ring W 1 , ring W 2 , R 1 and R 2 has the same meaning as described above.
R3, R4, R5 및 R6은 각각 독립적으로 수소 원자, 복소환기, 치환기를 가질 수 있는 탄소수 1 내지 24의 탄화수소기를 나타내고, 상기 탄화수소기에 포함되는 -CH2- 또는 =CH-는 -O- 또는 -S-에 치환될 수 있다.R 3 , R 4 , R 5 and R 6 each independently represent a hydrogen atom, a heterocyclic group, or a hydrocarbon group having 1 to 24 carbon atoms which may have a substituent, and -CH 2 - or =CH- contained in the hydrocarbon group is - may be substituted for O- or -S-.
R3 및 R4는 서로 연결하여 고리를 형성할 수 있다.R 3 and R 4 may be connected to each other to form a ring.
R5 및 R6은 서로 연결하여 고리를 형성할 수 있다.]R 5 and R 6 may be connected to each other to form a ring.]
[6]　[5]에 있어서, 식 (I-A)로 표시되는 양이온이 식 (I-B)로 표시되는 양이온 또는 식 (I-C)로 표시되는 양이온인 화합물.[6] The compound according to [5], wherein the cation represented by formula (I-A) is a cation represented by formula (I-B) or a cation represented by formula (I-C).
[화학식 3][Formula 3]
Figure PCTKR2022010249-appb-I000003
Figure PCTKR2022010249-appb-I000003
[식 (I-B) 및 식 (I-C) 중,[In Formula (I-B) and Formula (I-C),
고리 W1, 고리 W2, R1 및 R2는 각각 상기와 동일한 의미를 나타낸다.Each of ring W 1 , ring W 2 , R 1 and R 2 has the same meaning as described above.
Ar1 및 Ar2는 각각 독립적으로 치환기를 가질 수 있는 탄소수 6 내지 24의 방향족 탄화수소기를 나타낸다.Ar 1 and Ar 2 each independently represent an aromatic hydrocarbon group having 6 to 24 carbon atoms which may have a substituent.
R4A 및 R6A는 각각 독립적으로 수소 원자 또는 치환기를 가질 수 있는 탄소수 6 내지 24의 탄화수소기를 나타낸다.R 4A and R 6A each independently represent a hydrogen atom or a hydrocarbon group having 6 to 24 carbon atoms which may have a substituent.
고리 W3 및 고리 W4는 각각 독립적으로 함질소 복소환기를 나타낸다.]Ring W 3 and Ring W 4 each independently represent a nitrogen-containing heterocyclic group.]
[7]　[1] 내지 [6] 중 어느 하나에 있어서, 파장 400 nm 내지 파장 700 nm 사이에 극대 흡수를 나타내는 화합물.[7] The compound according to any one of [1] to [6], which exhibits maximum absorption between a wavelength of 400 nm and a wavelength of 700 nm.
[8]　[1] 내지 [7] 중 어느 하나에 따른 화합물과 수지를 포함하는 수지 조성물.[8] A resin composition comprising the compound according to any one of [1] to [7] and a resin.
[9]　[1] 내지 [7] 중 어느 하나에 따른 화합물과 중합성 모노머를 포함하는 조성물.[9] A composition containing the compound according to any one of [1] to [7] and a polymerizable monomer.
[10]　[8] 또는 [9]에 따른 조성물로부터 성형되는 성형체.[10] A molded article molded from the composition according to [8] or [9].
[11]　[1] 내지 [7] 중 어느 하나에 따른 화합물에 의해 염색된 염색물.[11] A dyed article dyed with the compound according to any one of [1] to [7].
[12]　하기 식 (I)로 표시되는 부분 구조를 포함하는 양이온을 포함하는 광학층.[12] An optical layer containing cations containing a partial structure represented by the following formula (I).
[화학식 4][Formula 4]
Figure PCTKR2022010249-appb-I000004
Figure PCTKR2022010249-appb-I000004
[식 (I) 중,[In Formula (I),
고리 W1 및 고리 W2는 각각 독립적으로 적어도 하나의 이중 결합을 고리의 구성 요소로 갖는 고리 구조를 나타낸다.Ring W 1 and ring W 2 each independently represent a ring structure having at least one double bond as a ring component.
고리 W1 및 고리 W2는 각각 독립적으로 치환기를 가질 수 있다.Ring W 1 and ring W 2 may each independently have a substituent.
R1 및 R2는 각각 독립적으로 수소 원자 또는 1가의 치환기를 나타내고, R1 및 R2 중 적어도 한쪽은 1가의 치환기이다.]R 1 and R 2 each independently represent a hydrogen atom or a monovalent substituent, and at least one of R 1 and R 2 is a monovalent substituent.]
본 발명은 가시광 영역(파장 400 nm 내지 파장 750 nm, 바람직하게 파장 450 nm 내지 파장 600 nm)의 빛을 효율적으로 흡수하고, 동시에 양호한 내후성을 갖는 신규 화합물을 제공하는 것을 목적으로 한다.An object of the present invention is to provide a novel compound that efficiently absorbs light in the visible light region (wavelength 400 nm to wavelength 750 nm, preferably wavelength 450 nm to wavelength 600 nm) and at the same time has good weather resistance.
본 발명의 화합물은 하기 식 (I)로 표시되는 부분 구조를 포함하는 양이온을 포함하는 화합물(이하 화합물(I)이라 하는 경우가 있다.)이다.The compound of the present invention is a compound containing a cation containing a partial structure represented by the following formula (I) (hereinafter sometimes referred to as compound (I)).
[화학식 5][Formula 5]
Figure PCTKR2022010249-appb-I000005
Figure PCTKR2022010249-appb-I000005
[식 (I) 중,[In Formula (I),
고리 W1 및 고리 W2는 각각 독립적으로 적어도 하나의 이중 결합을 고리의 구성 요소로 갖는 고리 구조를 나타낸다.Ring W 1 and ring W 2 each independently represent a ring structure having at least one double bond as a ring component.
고리 W1 및 고리 W2는 각각 독립적으로 치환기를 가질 수 있다.Ring W 1 and ring W 2 may each independently have a substituent.
R1 및 R2는 각각 독립적으로 수소 원자 또는 1가의 치환기를 나타내고, R1 및 R2 중 적어도 한쪽은 1가의 치환기이다.]R 1 and R 2 each independently represent a hydrogen atom or a monovalent substituent, and at least one of R 1 and R 2 is a monovalent substituent.]
＜양이온＞<cation>
식 (I)로 표시되는 부분 구조를 갖는 양이온은 하기에 나타낸 바와 같은 공명 구조도 모두 포함한다.A cation having a partial structure represented by formula (I) also includes all resonance structures as shown below.
[화학식 6][Formula 6]
Figure PCTKR2022010249-appb-I000006
Figure PCTKR2022010249-appb-I000006
고리 W1 및 고리 W2는 각각 독립적으로 고리의 구성 요소로서 적어도 하나의 이중 결합을 갖는 고리 구조를 나타낸다. 고리 W1 및 고리 W2는 고리의 구성 요소로서 이중 결합을 하나 이상 갖지만, 고리 W1 및 고리 W2에 포함되는 이중 결합은 통상적으로 1 내지 4이며, 1 내지 3인 것이 바람직하고, 1 또는 2인 것이 보다 바람직하고, 1인 것이 더욱 바람직하다.Ring W 1 and ring W 2 each independently represent a ring structure having at least one double bond as a ring component. Ring W 1 and ring W 2 have at least one double bond as a component of the ring, but the number of double bonds included in ring W 1 and ring W 2 is usually 1 to 4, preferably 1 to 3, and 1 or It is more preferable that it is 2, and it is still more preferable that it is 1.
고리 W1 및 고리 W2는 각각 독립적으로 단환일 수도 있으며, 다환일 수도 있다. 고리 W1 및 고리 W2는 각각 독립적으로 방향환일 수도 있으며, 방향족성을 갖지 않는 고리(지방족환)일 수도 있지만, 방향족성을 갖지 않는 고리인 것이 바람직하다. 방향족성을 갖지 않는 고리라면 보다 선택 흡수성을 높일 수 있다.Ring W 1 and ring W 2 may each independently be monocyclic or polycyclic. The ring W 1 and the ring W 2 may each independently be an aromatic ring or a non-aromatic ring (aliphatic ring), but is preferably a non-aromatic ring. If it is a ring which does not have aromaticity, the selective absorption property can be further improved.
고리 W1 및 고리 W2는 각각 독립적으로 헤테로 원자(예컨대 질소 원자, 산소 원자, 황 원자 등)를 포함하는 복소환일 수도 있으며, 탄화수소로 이루어진 고리일 수도 있다. 고리 W1 및 고리 W2는 각각 독립적으로 탄화수소로 이루어진 고리인 것이 바람직하다.Ring W 1 and ring W 2 may each independently be a heterocycle containing a hetero atom (eg, a nitrogen atom, an oxygen atom, a sulfur atom, etc.), or may be a hydrocarbon ring. It is preferable that ring W 1 and ring W 2 are each independently a ring composed of a hydrocarbon.
고리 W1 및 고리 W2는 각각 독립적으로 3원 고리 내지 20원 고리의 고리 구조인 것이 바람직하고, 3원 고리 내지 12원 고리인 것이 보다 바람직하고, 4원 고리 내지 6원 고리인 것이 바람직하다.Ring W 1 and ring W 2 are each independently preferably a 3-membered ring to a 20-membered ring structure, more preferably a 3-membered ring to a 12-membered ring, and preferably a 4-membered ring to a 6-membered ring. .
고리 W1 및 고리 W2는 각각 독립적으로 단환인 것이 바람직하다.It is preferable that ring W 1 and ring W 2 are each independently monocyclic.
고리 W1과 고리 W2는 축합환을 형성하고 있다. 고리 W1과 고리 W2로 형성되는 축합환은 지방족 탄화수소의 축합환인 것이 바람직하고, 탄소수 6 내지 40의 지방족 탄화수소의 축합환인 것이 보다 바람직하다.Ring W 1 and ring W 2 form a condensed ring. The condensed ring formed by the ring W 1 and the ring W 2 is preferably a condensed ring of an aliphatic hydrocarbon, more preferably a condensed ring of an aliphatic hydrocarbon having 6 to 40 carbon atoms.
고리 W1과 고리 W2로 형성되는 축합환은 예컨대 이하에 기재된 축합환을 들 수 있다. 하기 식 중의 *는 결합 부위를 나타낸다.The condensed ring formed by ring W 1 and ring W 2 includes, for example, the condensed ring described below. In the following formula, * represents a binding site.
[화학식 7][Formula 7]
Figure PCTKR2022010249-appb-I000007
Figure PCTKR2022010249-appb-I000007
고리 W1 및 고리 W2는 각각 독립적으로 치환기를 가질 수 있다. 상기 치환기로는 불소 원자, 염소 원자, 브롬 원자, 요오드 원자 등의 할로겐 원자; 메틸기, 에틸기, 프로필기, 노르말부틸기, 이소부틸기, 터셔리부틸기, 펜틸기, 헥실기, 헵틸기, 옥틸기, 노닐기, 데실기, 2-에틸헥실기, 4-부틸옥틸기, 에테닐기, 프로페닐기, 부테닐기, 펜테닐기, 에티닐기, 프로피닐기, 알릴기, 시클로헥세닐기, 부타디에닐기 등의 탄소수 1 내지 25의 지방족 탄화수소기(바람직하게 탄소수 1 내지 12의 알킬기); 플루오로메틸기, 디플루오로메틸기, 트리플루오로메틸기, 2-플루오로에틸기, 2,2-디플루오로에틸기, 2,2,2-트리플루오로에틸기, 1,1,2,2-테트라플루오로에틸기, 1,1,2,2,2-펜타플루오로에틸기, 노나플루오로부틸기 등의 탄소수 1 내지 25의 할로겐화알킬기; 메톡시기, 에톡시기, 프로폭시기, 이소프로폭시기, 부톡시기, 터셔리부톡시기, 펜틸옥시기, 헥실옥시기, 2-에틸헥실옥시기, 4-부틸옥틸옥시기 등의 탄소수 1 내지 25의 알콕시기; 메틸티오기, 에틸티오기, 프로필티오기, 부틸티오기, 펜틸티오기, 헥실티오기 등의 탄소수 1 내지 12의 알킬티오기; 모노플루오로메톡시기, 디플루오로메톡시기, 트리플루오로메톡시기, 2-플루오로에톡시기, 1,1,2,2,2-펜타플루오로에톡시기, 헥사플루오로이소프로폭시기 등의 탄소수 1 내지 12의 불소화알콕시기; 트리플루오로메탄티오알콕시기 등의 탄소수 1 내지 12의 불소화알콕시기; 아미노기, 메틸아미노기, 에틸아미노기, 디메틸아미노기, 디에틸아미노기, 디페닐아미노기, 피페리디노기, 피롤리디노기, 메틸에틸 등의 1개 또는 2개의 탄소수 1 내지 25의 치환기로 치환될 수 있는 아미노기; 카바모일기, N-메틸카바모일기, N,N-디메틸카바모일기 등의 N-위치가 탄소수 1 내지 6의 알킬기로 치환될 수 있는 카바모일기; 메틸카보닐옥시기, 에틸카보닐옥시기 등의 탄소수 2 내지 12의 알킬카보닐옥시기; 메틸설포닐기, 에틸설포닐기 등의 탄소수 1 내지 12의 알킬설포닐기; 페닐기, 나프틸기, 비페닐기, 안트라세닐기 등의 탄소수 6 내지 25의 방향족 탄화수소기(바람직하게 탄화수소 6 내지 18의 아릴기); 페닐설포닐기 등의 탄소수 6 내지 12의 아릴설포닐기; 메톡시설포닐기, 에톡시설포닐기 등의 탄소수 1 내지 12의 알콕시설포닐기; 트리플루오로메틸설포닐기, 펜타플루오로에틸설포닐기, 트리플루오로에틸설포닐기 등의 탄소수 1 내지 12의 플루오로알킬설포닐기; 아세틸기, 에틸카보닐기 등의 탄소수 2 내지 12의 아실기; 알데히드기; 메톡시카보닐기, 에톡시카보닐기, 프로폭시카보닐기, 부틸옥시카보닐기 등의 탄소수 2 내지 12의 알콕시카보닐기; 메톡시티오카보닐기, 에톡시티오카보닐기 등의 탄소수 2 내지 12의 알콕시티오카보닐기; 시아노기; 니트로기; 수산기; 티올기; 설포기; 카바모일기; 카복실기; -SF3; -SF5 등을 들 수 있다.Ring W 1 and ring W 2 may each independently have a substituent. Examples of the substituent include halogen atoms such as a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom; methyl group, ethyl group, propyl group, normal butyl group, isobutyl group, tert-butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, 2-ethylhexyl group, 4-butyloctyl group, aliphatic hydrocarbon groups having 1 to 25 carbon atoms (preferably alkyl groups having 1 to 12 carbon atoms) such as ethenyl, propenyl, butenyl, pentenyl, ethynyl, propynyl, allyl, cyclohexenyl and butadienyl; Fluoromethyl group, difluoromethyl group, trifluoromethyl group, 2-fluoroethyl group, 2,2-difluoroethyl group, 2,2,2-trifluoroethyl group, 1,1,2,2-tetrafluoro halogenated alkyl groups having 1 to 25 carbon atoms such as roethyl group, 1,1,2,2,2-pentafluoroethyl group, and nonafluorobutyl group; 1 to 25 carbon atoms such as methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, tertiary butoxy group, pentyloxy group, hexyloxy group, 2-ethylhexyloxy group, 4-butyloctyloxy group, etc. an alkoxy group of; an alkylthio group having 1 to 12 carbon atoms, such as a methylthio group, an ethylthio group, a propylthio group, a butylthio group, a pentylthio group, and a hexylthio group; Monofluoromethoxy group, difluoromethoxy group, trifluoromethoxy group, 2-fluoroethoxy group, 1,1,2,2,2-pentafluoroethoxy group, hexafluoroisopropoxy group fluorinated alkoxy groups having 1 to 12 carbon atoms, such as; fluorinated alkoxy groups having 1 to 12 carbon atoms such as trifluoromethanethioalkoxy groups; an amino group which may be substituted with one or two substituents having 1 to 25 carbon atoms such as an amino group, a methylamino group, an ethylamino group, a dimethylamino group, a diethylamino group, a diphenylamino group, a piperidino group, a pyrrolidino group, and a methylethyl group; a carbamoyl group in which the N-position may be substituted with an alkyl group having 1 to 6 carbon atoms, such as a carbamoyl group, an N-methylcarbamoyl group, and a N,N-dimethylcarbamoyl group; Alkylcarbonyloxy groups having 2 to 12 carbon atoms such as methylcarbonyloxy group and ethylcarbonyloxy group; alkylsulfonyl groups having 1 to 12 carbon atoms such as methylsulfonyl group and ethylsulfonyl group; Aromatic hydrocarbon groups of 6 to 25 carbon atoms (preferably aryl groups of 6 to 18 hydrocarbons) such as phenyl, naphthyl, biphenyl and anthracenyl groups; arylsulfonyl groups having 6 to 12 carbon atoms such as phenylsulfonyl groups; alkoxysulfonyl groups having 1 to 12 carbon atoms such as a methoxysulfonyl group and an ethoxysulfonyl group; a fluoroalkylsulfonyl group having 1 to 12 carbon atoms such as a trifluoromethylsulfonyl group, a pentafluoroethylsulfonyl group, and a trifluoroethylsulfonyl group; acyl groups having 2 to 12 carbon atoms, such as an acetyl group and an ethyl carbonyl group; aldehyde group; alkoxycarbonyl groups having 2 to 12 carbon atoms, such as a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, and a butyloxycarbonyl group; alkoxythiocarbonyl groups having 2 to 12 carbon atoms, such as a methoxythiocarbonyl group and an ethoxythiocarbonyl group; cyano group; nitro group; hydroxyl group; thiol group; sulfo group; carbamoyl group; carboxyl group; -SF 3 ; -SF 5 etc. are mentioned.
고리 W1과 고리 W2로 형성되는 축합환도 치환기를 가질 수 있고, 상기 치환기는 고리 W1 또는 고리 W2가 가질 수 있는 치환기를 들 수 있다.The condensed ring formed by ring W 1 and ring W 2 may also have a substituent, and the substituent may include a substituent that ring W 1 or ring W 2 may have.
R1 및 R2는 각각 독립적으로 수소 원자 또는 1가의 치환기를 나타내지만, R1 및 R2에서 선택되는 적어도 한쪽은 1가의 치환기이다.R 1 and R 2 each independently represent a hydrogen atom or a monovalent substituent, and at least one selected from R 1 and R 2 is a monovalent substituent.
R1 및 R2로 나타나는 1가의 치환기는 수소 원자가 아니면 특별히 한정되지 않지만, 예컨대 1가의 지방족 탄화수소기, 1가의 방향족 탄화수소기, 전자 흡인성기, 전자 공여성기, 헤테로 고리기, 폴리옥시알킬렌기를 갖는 기 등을 들 수 있다.The monovalent substituent represented by R 1 and R 2 is not particularly limited as long as it is not a hydrogen atom, and has, for example, a monovalent aliphatic hydrocarbon group, a monovalent aromatic hydrocarbon group, an electron withdrawing group, an electron donating group, a heterocyclic group, or a polyoxyalkylene group and the like.
R1 및 R2로 나타나는 1가의 지방족 탄화수소기로는 메틸기, 에틸기, n-프로필기, 이소프로필기, n-부틸기, tert-부틸기, sec-부틸기, n-펜틸기, 이소펜틸기, n-헥실기, 이소헥실기, n-옥틸기, 이소옥틸기, n-노닐기, 이소노닐기, n-데실기, 이소데실기, n-도데실기, 이소도데실기, 운데실기, 라우릴기, 미리스틸기, 세틸기, 스테아릴기, 2-에틸헥실기, 4-부틸옥틸기 등의 탄소수 1 내지 25의 직쇄형 또는 분기쇄형 알킬기: 시클로프로필기, 시클로부틸기, 시클로펜틸기, 시클로헥실기 등의 탄소수 3 내지 25의 시클로알킬기; 시클로헥실메틸기 등의 탄소수 4 내지 25의 시클로알킬알킬기: 이소보로닐기 등의 탄소수 4 내지 25의 알킬시클로알킬기; 에테닐기, 프로페닐기, 부테닐기, 펜테닐기, 에티닐기, 프로피닐기, 알릴기, 시클로헥세닐기, 부타디에닐기 등의 불포화 지방족 탄화수소기;를 들 수 있다. 바람직하게 탄소수 1 내지 12의 직쇄형 또는 분기쇄형 알킬기이다.Examples of the monovalent aliphatic hydrocarbon group represented by R 1 and R 2 include methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, n-pentyl, isopentyl, n-hexyl group, isohexyl group, n-octyl group, isooctyl group, n-nonyl group, isononyl group, n-decyl group, isodecyl group, n-dodecyl group, isododecyl group, undecyl group, lauryl group , Myristyl group, cetyl group, stearyl group, 2-ethylhexyl group, straight-chain or branched chain alkyl group having 1 to 25 carbon atoms such as 4-butyloctyl group: cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclo Cycloalkyl groups having 3 to 25 carbon atoms, such as a hexyl group; cycloalkylalkyl groups having 4 to 25 carbon atoms such as cyclohexylmethyl group; alkylcycloalkyl groups having 4 to 25 carbon atoms such as isoboronyl group; and unsaturated aliphatic hydrocarbon groups such as ethenyl, propenyl, butenyl, pentenyl, ethynyl, propynyl, allyl, cyclohexenyl and butadienyl. It is preferably a straight-chain or branched-chain alkyl group having 1 to 12 carbon atoms.
R1 및 R2로 나타나는 1가의 방향족 탄화수소기로는 페닐기, 나프틸기, 안트라세닐기, 테트라세닐기, 펜타세닐기, 페난트릴기, 크리세닐기, 트리페닐레닐기, 테트라페닐기, 피레닐기, 페릴레닐기, 코로네닐기, 비페닐기 등의 탄소수 6 내지 18의 아릴기; 벤질기, 페닐에틸기, 나프틸메틸기 등의 탄소수 7 내지 18의 아랄킬기; 페녹시에틸기, 페녹시디에틸렌글리콜기, 페녹시폴리알킬렌글리콜기의 아릴알콕시기 등을 들 수 있고, 탄소수 6 내지 18의 아릴기인 것이 바람직하고, 페닐기 또는 벤질기인 것이 보다 바람직하다.Examples of the monovalent aromatic hydrocarbon group represented by R 1 and R 2 include a phenyl group, a naphthyl group, anthracenyl group, tetracenyl group, pentacenyl group, phenanthryl group, chrysenyl group, triphenylenyl group, tetraphenyl group, pyrenyl group, and phenyl group. aryl groups having 6 to 18 carbon atoms, such as a relenyl group, a coronenyl group, and a biphenyl group; aralkyl groups having 7 to 18 carbon atoms such as benzyl group, phenylethyl group and naphthylmethyl group; A phenoxyethyl group, a phenoxydiethylene glycol group, an arylalkoxy group of a phenoxypolyalkylene glycol group, etc. are mentioned, and an aryl group having 6 to 18 carbon atoms is preferable, and a phenyl group or a benzyl group is more preferable.
R1 및 R2로 나타나는 전자 공여성기로는 수산기; 메톡시기, 에톡시기, 프로폭시기, 부톡시기, 펜틸옥시기, 헥실옥시기, 헵틸옥시기, 옥틸옥시기, 2-에틸헥실옥시기, 4-부틸옥틸옥시기 등의 탄소수 1 내지 25의 알콕시기; 메틸티오기, 에틸티오기, 프로필티오기, 부틸티오기, 펜틸티오기, 헥실티오기 등의 탄소수 1 내지 12의 알킬티오기; 아미노기, 모노메틸아미노기, 모노에틸아미노기, 디메틸아미노기, 디에틸아미노기, 메틸에틸아미노기 등의 1개 또는 2개의 탄소수 1 내지 6의 알킬기로 치환될 수 있는 아미노기 등을 들 수 있다.Examples of the electron-donating group represented by R 1 and R 2 include a hydroxyl group; Alkoxy having 1 to 25 carbon atoms such as methoxy group, ethoxy group, propoxy group, butoxy group, pentyloxy group, hexyloxy group, heptyloxy group, octyloxy group, 2-ethylhexyloxy group, 4-butyloctyloxy group, etc. energy; an alkylthio group having 1 to 12 carbon atoms, such as a methylthio group, an ethylthio group, a propylthio group, a butylthio group, a pentylthio group, and a hexylthio group; and amino groups which may be substituted with one or two alkyl groups having 1 to 6 carbon atoms, such as an amino group, a monomethylamino group, a monoethylamino group, a dimethylamino group, a diethylamino group, and a methylethylamino group.
R1 및 R2로 나타나는 헤테로 고리기로는 피롤리딘 고리기, 피페리딘 고리기, 피롤린 고리기, 이미다졸리딘 고리기, 이미다졸린 고리기, 옥사졸린 고리기, 티아졸린 고리기, 피페리딘 고리기, 모폴린 고리기, 피페라진 고리기, 인돌 고리기, 이소인돌 고리기, 퀴놀린 고리기, 티오펜 고리기, 피롤 고리기, 티아졸린 고리기 및 퓨란 고리기, 테트라히드로퓨란 고리기 등의 탄소수 4 내지 20의 지방족 복소환기 또는 탄소수 3 내지 20의 방향족 복소환기 등을 들 수 있다.Examples of the heterocyclic group represented by R 1 and R 2 include a pyrrolidine ring group, a piperidine ring group, a pyrroline ring group, an imidazolidine ring group, an imidazoline ring group, an oxazoline ring group, and a thiazoline ring group. , piperidine ring group, morpholine ring group, piperazine ring group, indole ring group, isoindole ring group, quinoline ring group, thiophene ring group, pyrrole ring group, thiazoline ring group and furan ring group, tetrahydro and an aliphatic heterocyclic group having 4 to 20 carbon atoms, such as a furan ring group, or an aromatic heterocyclic group having 3 to 20 carbon atoms.
R1 및 R2로 나타나는 폴리옥시알킬렌기를 갖는 기로는 옥시에틸렌기(-CH2CH2O-), 옥시프로필기(-CH2CH2CH2O-) 등을 갖는 기이다. 보다 구체적으로 -(X11O)m-R11로 나타나는 기(X11은 탄소수 1 내지 6의 알킬렌기를 나타내고, R11은 수산기를 가질 수 있는 탄소수 1 내지 6의 알킬기를 나타내고, m은 1 내지 6의 정수를 나타낸다.) 등을 들 수 있다.The group having a polyoxyalkylene group represented by R 1 and R 2 is a group having an oxyethylene group (-CH 2 CH 2 O-), an oxypropyl group (-CH 2 CH 2 CH 2 O-), and the like. More specifically, a group represented by -(X 11 O)mR 11 (X 11 represents an alkylene group having 1 to 6 carbon atoms, R 11 represents an alkyl group having 1 to 6 carbon atoms which may have a hydroxyl group, and m is 1 to 6 represents the integer of).
R1 및 R2로 나타나는 전자 흡인성기로는 예컨대 할로겐 원자, 니트로기, 시아노기, 카복시기, 할로겐화알킬기, 할로겐화아릴기, -OCF3, -SCF3, -SF5, -SF3, -SO3H, -SO2H, 식 (z-1)로 표시되는 기를 들 수 있다.Examples of electron-withdrawing groups represented by R 1 and R 2 include halogen atoms, nitro groups, cyano groups, carboxy groups, halogenated alkyl groups, halogenated aryl groups, -OCF 3 , -SCF 3 , -SF 5 , -SF 3 , -SO 3 H, -SO 2 H, and a group represented by the formula (z-1).
[화학식 8][Formula 8]
Figure PCTKR2022010249-appb-I000008
Figure PCTKR2022010249-appb-I000008
[식 (z-1) 중,[In Formula (z-1),
R222는 수소 원자, 할로겐 원자, 치환기를 가질 수 있는 탄화수소기, 폴리옥시알킬렌기를 갖는 기를 나타낸다.R 222 represents a hydrogen atom, a halogen atom, a hydrocarbon group which may have a substituent, or a group having a polyoxyalkylene group.
X1은 -CO-, -COO-, -OCO-, -CS-, -CSS-, -COS-, -CSO-, -SO2-, -NR223CO- 또는 -CONR224-를 나타낸다.X 1 represents -CO-, -COO-, -OCO-, -CS-, -CSS-, -COS-, -CSO-, -SO 2 -, -NR 223 CO- or -CONR 224 -.
R223 및 R224는 각각 독립적으로 수소 원자, 탄소수 1 내지 6의 알킬기 또는 페닐기를 나타낸다.R 223 and R 224 each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a phenyl group.
*는 결합 부위를 나타낸다.]* indicates a binding site.]
할로겐 원자로는 불소 원자, 염소 원자, 브롬 원자, 요오드 원자를 들 수 있다.A fluorine atom, a chlorine atom, a bromine atom, and an iodine atom are mentioned as a halogen atom.
할로겐화알킬기로는 트리플루오로메틸기, 퍼플루오로에틸기, 퍼플루오로프로필기, 퍼플루오로이소프로필기, 퍼플루오로부틸기, 퍼플루오로 sec-부틸기, 퍼플루오로 tert-부틸기, 퍼플루오로펜틸기, 퍼플루오로헥실기, 디클로로메틸기, 브로모메틸기, 요오드메틸기 등의 탄소수 1 내지 25의 할로겐화알킬기를 들 수 있다. 바람직하게 탄소수 1 내지 12의 할로겐화알킬기이며, 보다 바람직하게 탄소수 1 내지 12의 플루오로알킬기이며, 더욱 바람직하게 탄소수 1 내지 12의 퍼플루오로알킬기이다.Halogenated alkyl groups include trifluoromethyl, perfluoroethyl, perfluoropropyl, perfluoroisopropyl, perfluorobutyl, perfluoro sec-butyl, perfluoro tert-butyl, purple and halogenated alkyl groups having 1 to 25 carbon atoms, such as a fluoropentyl group, a perfluorohexyl group, a dichloromethyl group, a bromomethyl group, and an iodomethyl group. It is preferably a C1-C12 halogenated alkyl group, more preferably a C1-C12 fluoroalkyl group, still more preferably a C1-C12 perfluoroalkyl group.
할로겐화아릴기로는 플루오로페닐기, 클로로페닐기, 브로모페닐기 등의 탄소수 6 내지 18의 할로겐화아릴기를 들 수 있고, 탄소수 6 내지 18의 플루오로아릴기인 것이 바람직하고, 탄소수 6 내지 12의 퍼플루오로아릴기인 것이 보다 바람직하고, 더욱 바람직하게 펜타플루오로페닐기이다.Halogenated aryl groups include halogenated aryl groups having 6 to 18 carbon atoms such as fluorophenyl, chlorophenyl and bromophenyl groups, preferably fluoroaryl groups having 6 to 18 carbon atoms, and perfluoroaryl groups having 6 to 12 carbon atoms. A group is more preferable, and a pentafluorophenyl group is still more preferable.
X1은 -CO-, -COO- 또는 -SO2-인 것이 바람직하다.X 1 is preferably -CO-, -COO- or -SO 2 -.
R222로 나타나는 할로겐 원자로는 불소 원자, 염소 원자, 브롬 원자, 요오드 원자를 들 수 있다.The halogen atom represented by R 222 includes a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
R222로 나타나는 탄화수소기로는 탄소수 1 내지 25의 지방족 탄화수소기 또는 탄소수 6 내지 18의 방향족 탄화수소기 등을 들 수 있다.Examples of the hydrocarbon group represented by R 222 include an aliphatic hydrocarbon group having 1 to 25 carbon atoms or an aromatic hydrocarbon group having 6 to 18 carbon atoms.
탄소수 1 내지 25의 지방족 탄화수소기로는 메틸기, 에틸기, n-프로필기, 이소프로필기, n-부틸기, tert-부틸기, sec-부틸기, n-펜틸기, n-헥실기, 1-메틸부틸기, 3-메틸부틸기, n-옥틸기, n-데실, 2-헥실-옥틸기, 4-부틸옥틸기, 시클로헥실기 등의 직쇄형, 분기쇄형, 고리형의 탄소수 1 내지 25의 알킬기; 에테닐기, 프로페닐기, 부테닐기, 펜테닐기, 에티닐기, 프로피닐기, 알릴기, 시클로헥세닐기, 부타디에닐기 등의 불포화 지방족 탄화수소기; 등을 들 수 있고, 탄소수 1 내지 12의 알킬기인 것이 바람직하다.Examples of the aliphatic hydrocarbon group having 1 to 25 carbon atoms include methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, n-pentyl, n-hexyl, 1-methyl Straight-chain, branched-chain, or cyclic carbon atoms of 1 to 25, such as butyl group, 3-methylbutyl group, n-octyl group, n-decyl group, 2-hexyl-octyl group, 4-butyloctyl group and cyclohexyl group an alkyl group; unsaturated aliphatic hydrocarbon groups such as an ethenyl group, a propenyl group, a butenyl group, a pentenyl group, an ethynyl group, a propynyl group, an allyl group, a cyclohexenyl group, and a butadienyl group; These etc. are mentioned, It is preferable that it is a C1-C12 alkyl group.
탄소수 6 내지 18의 방향족 탄화수소기로는 페닐기, 나프틸기, 안트라세닐기, 비페닐기 등의 탄소수 6 내지 18의 아릴기; 벤질기, 페닐에틸기, 나프틸메틸기 등의 탄소수 7 내지 18의 아랄킬기 등을 들 수 있다.Examples of the aromatic hydrocarbon group having 6 to 18 carbon atoms include aryl groups having 6 to 18 carbon atoms such as a phenyl group, a naphthyl group, anthracenyl group, and a biphenyl group; and aralkyl groups having 7 to 18 carbon atoms, such as a benzyl group, a phenylethyl group, and a naphthylmethyl group.
R222로 나타나는 탄화수소기가 가질 수 있는 치환기로는 할로겐 원자, 히드록시기, 알콕시기, 티오알킬기, 디알킬아미노기 등을 들 수 있다.Examples of the substituent that the hydrocarbon group represented by R 222 may have include a halogen atom, a hydroxyl group, an alkoxy group, a thioalkyl group, and a dialkylamino group.
R222로 나타나는 폴리옥시알킬렌기를 갖는 기로는 R1로 나타나는 폴리옥시알킬렌기를 갖는 기와 동일한 것을 들 수 있다.Examples of the group having a polyoxyalkylene group represented by R 222 include the same group as the group having a polyoxyalkylene group represented by R 1 .
R223 및 R224로 나타나는 탄소수 1 내지 6의 알킬기로는 메틸기, 에틸기, n-프로필기, 이소프로필기, n-부틸기, tert-부틸기, sec-부틸기, n-펜틸기, n-헥실기, 1-메틸부틸기 등의 직쇄형 또는 분기쇄형의 탄소수 1 내지 6의 알킬을 들 수 있다.Examples of the C1-C6 alkyl group represented by R 223 and R 224 include methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, n-pentyl, n- and straight-chain or branched-chain alkyls having 1 to 6 carbon atoms, such as a hexyl group and a 1-methylbutyl group.
식 (z-1)로 표시되는 기는 -CO-R1, -CO-O-R2, -CO-NR3R3k, -CO-S-R4, -CS-R5, -CS-O-R6, -CS-S-R7, -SO-R8, -SO2-R9(R1, R2, R3, R3k, R4, R5, R6, R7, R8 및 R9는 각각 독립적으로 치환기를 가질 수 있는 탄화수소기 또는 할로겐 원자를 나타낸다.)인 것이 바람직하고,The group represented by formula (z-1) is -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 are each independently represents a hydrocarbon group or a halogen atom which may have a substituent).
-CO-R1, -CO-O-R2, -SO2-R9인 것이 보다 바람직하고,More preferably -CO-R 1 , -CO-OR 2 , -SO 2 -R 9 ,
-SO2-R9인 것이 더욱 바람직하고,-SO 2 -R 9 is more preferred,
-SO2-R10(R10은 치환기를 가질 수 있는 탄소수 6 내지 18의 방향족 탄화수소기), -SO2CF3, -SO2CHF2, -SO2CH2F인 것이 보다 더 바람직하다.More preferably -SO 2 -R 10 (R 10 is an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent), -SO 2 CF 3 , -SO 2 CHF 2 , or -SO 2 CH 2 F.
R1 및 R2에서 선택되는 적어도 하나는 전자 흡인성기인 것이 바람직하고,At least one selected from R 1 and R 2 is preferably an electron withdrawing group;
시아노기, 니트로기, 할로겐화알킬기, 할로겐화아릴기, -SCF3, -SF5, -SF3, -SO3H, -SO2H, -CO-R1, -CO-O-R2, -CO-NR3R3k, -CO-S-R4, -CS-R5, -CS-O-R6, -CS-S-R7, -SO-R8, -SO2-R9(R1, R2, R3, R3k, R4, R5, R6, R7, R8 및 R9는 각각 독립적으로 치환기를 가질 수 있는 탄화수소기 또는 할로겐 원자를 나타낸다.), -OCF3인 것이 보다 바람직하고,Cyano group, nitro group, halogenated alkyl group, halogenated aryl group, -SCF 3 , -SF 5 , -SF 3 , -SO 3 H, -SO 2 H, -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 independently represent a hydrocarbon group which may have a substituent or a halogen atom), more preferably -OCF 3 ,
시아노기, 니트로기, -OCF3, -SCF3, -SF5, -SF3, -SO3H, -SO2H, -CO-R1, -CO-O-R2, -SO2-R9인 것이 더욱 바람직하고,Cyano group, nitro group, -OCF 3 , -SCF 3 , -SF 5 , -SF 3 , -SO 3 H, -SO 2 H, -CO-R 1 , -CO-OR 2 , -SO 2 -R 9 More preferably,
시아노기, 니트로기, -OCF3, -SCF3, -SF5, -SO2CF3, -SO2-R10인 것이 보다 더 바람직하고,A cyano group, a nitro group, -OCF 3 , -SCF 3 , -SF 5 , -SO 2 CF 3 , -SO 2 -R 10 are more preferred,
시아노기 또는 니트로기인 것이 특히 바람직하고,A cyano group or a nitro group is particularly preferred,
시아노기인 것이 특히 더 바람직하다.A cyano group is particularly preferred.
식 (I)로 표시되는 부분 구조를 포함하는 양이온은 식 (I-A)로 표시되는 양이온인 것이 바람직하다.It is preferable that the cation containing the partial structure represented by formula (I) is a cation represented by formula (I-A).
[화학식 9][Formula 9]
Figure PCTKR2022010249-appb-I000009
Figure PCTKR2022010249-appb-I000009
[식 (I-A) 중,[In Formula (I-A),
고리 W1, 고리 W2, R1 및 R2는 각각 상기와 동일한 의미를 나타낸다.Each of ring W 1 , ring W 2 , R 1 and R 2 has the same meaning as described above.
R3, R4, R5 및 R6은 각각 독립적으로 수소 원자, 복소환기, 치환기를 가질 수 있는 탄소수 1 내지 24의 탄화수소기를 나타내고, 상기 탄화수소기에 포함되는 -CH2- 또는 =CH-는 -O- 또는 -S-에 치환될 수 있다.R 3 , R 4 , R 5 and R 6 each independently represent a hydrogen atom, a heterocyclic group, or a hydrocarbon group having 1 to 24 carbon atoms which may have a substituent, and -CH 2 - or =CH- contained in the hydrocarbon group is - may be substituted for O- or -S-.
R3 및 R4는 서로 연결하여 고리를 형성할 수 있다.R 3 and R 4 may be connected to each other to form a ring.
R5 및 R6은 서로 연결하여 고리를 형성할 수 있다.]R 5 and R 6 may be connected to each other to form a ring.]
R3, R4, R5 및 R6으로 나타나는 탄소수 1 내지 24의 탄화수소기로는 탄소수 1 내지 24의 지방족 탄화수소기, 탄소수 6 내지 24의 방향족 탄화수소기 등을 들 수 있다.Examples of the hydrocarbon group having 1 to 24 carbon atoms represented by R 3 , R 4 , R 5 and R 6 include an aliphatic hydrocarbon group having 1 to 24 carbon atoms and an aromatic hydrocarbon group having 6 to 24 carbon atoms.
탄소수 1 내지 24의 지방족 탄화수소기로는 메틸기, 에틸기, n-프로필기, 이소프로필기, n-부틸기, tert-부틸기, sec-부틸기, n-펜틸기, n-헥실기, 1-메틸부틸기, 3-메틸부틸기, n-옥틸기, n-데실, 2-헥실-옥틸기, 4-부틸옥틸기, 시클로헥실기 등의 직쇄형, 분기쇄형, 고리형의 탄소수 1 내지 24의 알킬기; 에테닐기, 프로페닐기, 부테닐기, 펜테닐기, 에티닐기, 프로피닐기, 알릴기, 시클로헥세닐기, 부타디에닐기 등의 불포화 지방족 탄화수소기 등을 들 수 있다.Examples of the aliphatic hydrocarbon group having 1 to 24 carbon atoms include methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, n-pentyl, n-hexyl, 1-methyl Straight-chain, branched-chain, or cyclic carbon atoms of 1 to 24, such as butyl group, 3-methylbutyl group, n-octyl group, n-decyl group, 2-hexyl-octyl group, 4-butyloctyl group, and cyclohexyl group an alkyl group; and unsaturated aliphatic hydrocarbon groups such as ethenyl, propenyl, butenyl, pentenyl, ethynyl, propynyl, allyl, cyclohexenyl and butadienyl.
탄소수 6 내지 24의 방향족 탄화수소기로는 페닐기, 나프틸기, 안트라세닐기, 비페닐기 등의 탄소수 6 내지 24의 아릴기; 벤질기, 페닐에틸기, 나프틸메틸기 등의 탄소수 7 내지 24의 아랄킬기 등을 들 수 있다.Examples of the aromatic hydrocarbon group having 6 to 24 carbon atoms include aryl groups having 6 to 24 carbon atoms such as a phenyl group, a naphthyl group, an anthracenyl group, and a biphenyl group; and aralkyl groups having 7 to 24 carbon atoms such as benzyl group, phenylethyl group and naphthylmethyl group.
R3, R4, R5 및 R6으로 나타나는 탄소수 1 내지 24의 탄화수소기에 포함되는 -CH2- 또는 =CH-는 -O- 또는 -S-에 치환될 수 있다. 예컨대 탄소수 1 내지 24의 탄화수소기에 포함되는 -CH2- 또는 =CH-가 -O-로 치환된 기로는 메톡시기, 에톡시기, 프로폭시기 등의 탄소수 1 내지 24의 알콕시기; 페톡시기 등의 탄소수 6 내지 18의 아릴옥시기; 옥시에틸렌기(-CH2CH2O-), 옥시프로필기(-CH2CH2CH2O-) 등을 포함하는 -(X12O)m1-R12로 나타나는 기(X12는 탄소수 1 내지 6의 알킬렌기를 나타내고, R12는 수산기를 가질 수 있는 탄소수 1 내지 6의 알킬기를 나타내고, m1은 1 내지 6의 정수를 나타내고, 탄소수의 합계가 24 이하이다) 등을 들 수 있다.-CH 2 - or =CH- contained in a hydrocarbon group having 1 to 24 carbon atoms represented by R 3 , R 4 , R 5 and R 6 may be substituted for -O- or -S-. Examples of groups in which -CH 2 - or =CH- contained in a hydrocarbon group having 1 to 24 carbon atoms is substituted with -O- include an alkoxy group having 1 to 24 carbon atoms such as a methoxy group, an ethoxy group, and a propoxy group; aryloxy groups having 6 to 18 carbon atoms such as a phenoxy group; A group represented by -(X 12 O) m1 -R 12 including an oxyethylene group (-CH 2 CH 2 O-), an oxypropyl group (-CH 2 CH 2 CH 2 O-), etc. (X 12 has 1 carbon atom) to 6 alkylene groups, R 12 represents an alkyl group having 1 to 6 carbon atoms which may have a hydroxyl group, m1 represents an integer of 1 to 6, and the total number of carbon atoms is 24 or less).
탄소수 1 내지 24의 탄화수소기에 포함되는 -CH2- 또는 =CH-가 -S-로 치환된 기로는 메틸티오기, 에틸티오기, 프로필티오기, 부틸티오기, 펜틸티오기, 헥실티오기 등의 탄소수 1 내지 18의 알킬티오기; 페닐티오기 등의 탄소수 6 내지 18의 아릴티오기; 티오에틸렌기(-CH2CH2S-), 티오프로필기(-CH2CH2CH2S-) 등을 포함하는 -(X13S)m2-R13으로 나타나는 기(X13은 탄소수 1 내지 6의 알킬렌기를 나타내고, R13은 수산기를 가질 수 있는 탄소수 1 내지 6의 알킬기를 나타내고, m2는 1 내지 6의 정수를 나타내고, 탄소수의 합계가 24 이하이다) 등을 들 수 있다.Groups in which -CH 2 - or =CH- contained in a hydrocarbon group having 1 to 24 carbon atoms is substituted with -S- include methylthio, ethylthio, propylthio, butylthio, pentylthio, hexylthio, etc. An alkylthio group having 1 to 18 carbon atoms; arylthio groups having 6 to 18 carbon atoms such as phenylthio groups; A group represented by -(X 13 S) m2 -R 13 including a thioethylene group (-CH 2 CH 2 S-), a thiopropyl group (-CH 2 CH 2 CH 2 S-), etc. (X 13 has 1 carbon atom) to 6 alkylene groups, R 13 represents an alkyl group having 1 to 6 carbon atoms which may have a hydroxyl group, m2 represents an integer of 1 to 6, and the total number of carbon atoms is 24 or less).
R3, R4, R5 및 R6으로 나타나는 탄소수 1 내지 24의 탄화수소기가 가질 수 있는 치환기로는 불소 원자, 염소 원자, 브롬 원자, 요오드 원자 등의 할로겐 원자; 플루오로메틸기, 디플루오로메틸기, 트리플루오로메틸기, 2-플루오로에틸기, 2,2-디플루오로에틸기, 2,2,2-트리플루오로에틸기, 1,1,2,2-테트라플루오로에틸기, 1,1,2,2,2-펜타플루오로에틸기, 노나플루오로부틸기 등의 탄소수 1 내지 25의 할로겐화알킬기; 메톡시기, 에톡시기, 프로폭시기, 이소프로폭시기, 부톡시기, 터셔리부톡시기, 펜틸옥시기, 헥실옥시기, 2-에틸헥실옥시기, 4-부틸옥틸옥시기 등의 탄소수 1 내지 25의 알콕시기; 메틸티오기, 에틸티오기, 프로필티오기, 부틸티오기, 펜틸티오기, 헥실티오기 등의 탄소수 1 내지 12의 알킬티오기; 모노플루오로메톡시기, 디플루오로메톡시기, 트리플루오로메톡시기, 2-플루오로에톡시기, 1,1,2,2,2-펜타플루오로에톡시기, 헥사플루오로이소프로폭시기 등의 탄소수 1 내지 12의 불소화알콕시기; 트리플루오로메탄티오알콕시기 등의 탄소수 1 내지 12의 불소화알콕시기; 아미노기, 메틸아미노기, 에틸아미노기, 디메틸아미노기, 디에틸아미노기, 디페닐아미노기, 피페리디노기, 피롤리디노기, 메틸에틸 등의 1개 또는 2개의 탄소수 1 내지 25의 치환기로 치환될 수 있는 아미노기; 카바모일기, N-메틸카바모일기, N,N-디메틸카바모일기 등의 N-위치가 탄소수 1 내지 6의 알킬로 치환될 수 있는 카바모일기; 메틸카보닐옥시기, 에틸카보닐옥시기 등의 탄소수 2 내지 12의 알킬카보닐옥시기; 메틸설포닐기, 에틸설포닐기 등의 탄소수 1 내지 12의 알킬설포닐기; 페닐설포닐기 등의 탄소수 6 내지 12의 아릴설포닐기; 메톡시설포닐기, 에톡시설포닐기 등의 탄소수 1 내지 12의 알콕시설포닐기; 트리플루오로메틸설포닐기, 펜타플루오로에틸설포닐기, 트리플루오로에틸설포닐기 등의 탄소수 1 내지 12의 플루오로알킬설포닐기; 아세틸기, 에틸카보닐기 등의 탄소수 2 내지 12의 아실기; 알데히드기; 메톡시카보닐기, 에톡시카보닐기, 프로폭시카보닐기, 부틸옥시카보닐기 등의 탄소수 2 내지 12의 알콕시카보닐기; 메톡시티오카보닐기, 에톡시티오카보닐기 등의 탄소수 2 내지 12의 알콕시티오카보닐기; 시아노기; 니트로기; 수산기; 티올기; 설포기; 카바모일기; 카복실기; -SF3; -SF5 등을 들 수 있다.Substituents that the hydrocarbon group having 1 to 24 carbon atoms represented by R 3 , R 4 , R 5 and R 6 may have include halogen atoms such as fluorine, chlorine, bromine and iodine; Fluoromethyl group, difluoromethyl group, trifluoromethyl group, 2-fluoroethyl group, 2,2-difluoroethyl group, 2,2,2-trifluoroethyl group, 1,1,2,2-tetrafluoro halogenated alkyl groups having 1 to 25 carbon atoms such as roethyl group, 1,1,2,2,2-pentafluoroethyl group, and nonafluorobutyl group; 1 to 25 carbon atoms such as methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, tertiary butoxy group, pentyloxy group, hexyloxy group, 2-ethylhexyloxy group, 4-butyloctyloxy group, etc. an alkoxy group of; an alkylthio group having 1 to 12 carbon atoms, such as a methylthio group, an ethylthio group, a propylthio group, a butylthio group, a pentylthio group, and a hexylthio group; Monofluoromethoxy group, difluoromethoxy group, trifluoromethoxy group, 2-fluoroethoxy group, 1,1,2,2,2-pentafluoroethoxy group, hexafluoroisopropoxy group fluorinated alkoxy groups having 1 to 12 carbon atoms, such as; fluorinated alkoxy groups having 1 to 12 carbon atoms such as trifluoromethanethioalkoxy groups; an amino group which may be substituted with one or two substituents having 1 to 25 carbon atoms such as an amino group, a methylamino group, an ethylamino group, a dimethylamino group, a diethylamino group, a diphenylamino group, a piperidino group, a pyrrolidino group, and a methylethyl group; a carbamoyl group in which the N-position such as a carbamoyl group, an N-methylcarbamoyl group, or a N,N-dimethylcarbamoyl group may be substituted with an alkyl having 1 to 6 carbon atoms; Alkylcarbonyloxy groups having 2 to 12 carbon atoms such as methylcarbonyloxy group and ethylcarbonyloxy group; alkylsulfonyl groups having 1 to 12 carbon atoms such as methylsulfonyl group and ethylsulfonyl group; arylsulfonyl groups having 6 to 12 carbon atoms such as phenylsulfonyl groups; alkoxysulfonyl groups having 1 to 12 carbon atoms such as a methoxysulfonyl group and an ethoxysulfonyl group; a fluoroalkylsulfonyl group having 1 to 12 carbon atoms such as a trifluoromethylsulfonyl group, a pentafluoroethylsulfonyl group, and a trifluoroethylsulfonyl group; acyl groups having 2 to 12 carbon atoms, such as an acetyl group and an ethyl carbonyl group; aldehyde group; alkoxycarbonyl groups having 2 to 12 carbon atoms, such as a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, and a butyloxycarbonyl group; alkoxythiocarbonyl groups having 2 to 12 carbon atoms, such as a methoxythiocarbonyl group and an ethoxythiocarbonyl group; cyano group; nitro group; hydroxyl group; thiol group; sulfo group; carbamoyl group; carboxyl group; -SF 3 ; -SF 5 etc. are mentioned.
R3, R4, R5 및 R6으로 나타나는 복소환기로는 아지리딘 고리기, 아제티딘 고리기, 피롤리딘 고리기, 피페리딘 고리기, 피롤린 고리기, 이미다졸리딘 고리기, 피라졸리딘 고리기, 이미다졸리딘 고리기, 이미다졸린 고리기, 옥사졸린 고리기, 티아졸린 고리기, 피페리딘 고리기, 모폴린 고리기, 피페라진 고리기, 인돌 고리기, 이소인돌 고리기, 퀴놀린 고리기, 티오펜 고리기, 피롤 고리기, 티아졸린 고리기 및 퓨란 고리기, 테트라히드로퓨란 고리기 등의 탄소수 4 내지 20의 지방족 복소환기 또는 탄소수 3 내지 20의 방향족 복소환기 등을 들 수 있다.Examples of the heterocyclic group represented by R 3 , R 4 , R 5 and R 6 include an aziridine ring group, an azetidine ring group, a pyrrolidine ring group, a piperidine ring group, a pyrroline ring group, and an imidazolidine ring group. , Pyrazolidine ring group, imidazolidine ring group, imidazoline ring group, oxazoline ring group, thiazoline ring group, piperidine ring group, morpholine ring group, piperazine ring group, indole ring group, An aliphatic heterocyclic group having 4 to 20 carbon atoms or an aromatic heterocyclic group having 3 to 20 carbon atoms, such as an isoindole ring group, a quinoline ring group, a thiophene ring group, a pyrrole ring group, a thiazoline ring group, a furan ring group, and a tetrahydrofuran ring group; Ventilation etc. are mentioned.
R3 및 R4가 서로 연결하여 형성하는 고리는 질소 원자를 고리의 구성 요소로 포함하는 고리이다. R3 및 R4가 서로 연결하여 형성하는 고리는 고리의 구성 요소로서 질소 원자 이외의 헤테로 원자를 포함하고 있을 수 있다. R3 및 R4가 서로 연결하여 형성하는 고리는 단환일 수도 있으며, 축합환일 수도 있다. R3 및 R4가 서로 연결하여 형성하는 고리로는 예컨대 아지리딘 고리기, 아제티딘 고리기, 피롤리딘 고리기, 피페리딘 고리기, 모폴린 고리기, 인돌린 고리기, 이미다졸린 고리기, 피라졸 고리기, 이미다졸 고리기, 트리아졸 고리기, 테트라졸 고리기, 티아졸리딘디온 고리기, 숙신이미드 고리기, 옥사졸리돈 고리기, 피페라진 고리기, 티오모폴린 고리기, 데카히드로이소퀴놀린 고리기, 데카히드로퀴놀린 고리기, 테트라히드로퀴놀린 고리기, 카바졸 고리기, 페노티아진 고리기, 아자아다만탄 고리기, 아조칸 고리기, 아조난 고리기 등을 들 수 있다. R3 및 R4가 서로 연결하여 형성하는 고리에 포함되는 수소 원자는 임의의 치환기로 치환될 수 있고, 상기 임의의 치환기로는 예컨대 고리 W1 및 고리 W2가 가질 수 있는 치환기와 동일한 기를 들 수 있다.A ring formed by connecting R 3 and R 4 is a ring containing a nitrogen atom as a component of the ring. A ring formed by connecting R 3 and R 4 may contain a hetero atom other than a nitrogen atom as a component of the ring. A ring formed by connecting R 3 and R 4 may be a monocyclic ring or a condensed ring. Examples of the ring formed by connecting R 3 and R 4 include an aziridine ring group, an azetidine ring group, a pyrrolidine ring group, a piperidine ring group, a morpholine ring group, an indoline ring group, and an imidazoline ring. Ring group, pyrazole ring group, imidazole ring group, triazole ring group, tetrazole ring group, thiazolidinedione ring group, succinimide ring group, oxazolidone ring group, piperazine ring group, thiomorpholine Ring group, decahydroisoquinoline ring group, decahydroquinoline ring group, tetrahydroquinoline ring group, carbazole ring group, phenothiazine ring group, azaadamantane ring group, azocan ring group, azonane ring group, etc. can be heard A hydrogen atom included in a ring formed by linking R 3 and R 4 to each other may be substituted with an arbitrary substituent, and the optional substituent includes, for example, the same substituents that ring W 1 and ring W 2 may have. can
R5 및 R6이 서로 연결하여 형성하는 고리는 질소 원자를 고리의 구성 요소로 포함하는 고리이다. R5 및 R6이 서로 연결하여 형성하는 고리는 고리의 구성 요소로서 질소 원자 이외의 헤테로 원자를 포함하고 있을 수 있다. R5 및 R6이 서로 연결하여 형성하는 고리는 단환일 수도 있으며, 축합환일 수도 있다. R5 및 R6이 서로 연결하여 형성하는 고리로는 R3 및 R4가 서로 연결하여 형성하는 고리와 동일한 고리를 들 수 있다. R5 및 R6이 서로 연결하여 형성하는 고리에 포함되는 수소 원자는 임의의 치환기로 치환될 수 있고, 상기 임의의 치환기로는 예컨대 고리 W1 및 고리 W2가 가질 수 있는 치환기와 동일한 기를 들 수 있다.A ring formed by connecting R 5 and R 6 to each other is a ring containing a nitrogen atom as a component of the ring. A ring formed by connecting R 5 and R 6 may contain a hetero atom other than a nitrogen atom as a component of the ring. A ring formed by connecting R 5 and R 6 to each other may be a monocyclic ring or a condensed ring. Examples of the ring formed by connecting R 5 and R 6 include the same rings as those formed by connecting R 3 and R 4 to each other. A hydrogen atom included in a ring formed by connecting R 5 and R 6 to each other may be substituted with an arbitrary substituent, and examples of the optional substituent include the same substituents as those of ring W 1 and ring W 2 . can
R3, R4, R5 및 R6은 각각 독립적으로 수소 원자 또는 탄소수 1 내지 24의 탄화수소기인 것이 바람직하다.It is preferable that each of R 3 , R 4 , R 5 and R 6 independently represents a hydrogen atom or a hydrocarbon group having 1 to 24 carbon atoms.
R3 및 R4에서 선택되는 적어도 하나가 탄소수 1 내지 24의 탄화수소기인 것이 바람직하고, 탄소수 6 내지 24의 방향족 탄화수소기인 것이 보다 바람직하다.At least one selected from R 3 and R 4 is preferably a hydrocarbon group of 1 to 24 carbon atoms, more preferably an aromatic hydrocarbon group of 6 to 24 carbon atoms.
R5 및 R6에서 선택되는 적어도 하나가 탄소수 1 내지 24의 탄화수소기인 것이 바람직하고, 탄소수 6 내지 24의 방향족 탄화수소기인 것이 보다 바람직하다.It is preferable that at least one selected from R5 and R6 is a C1 - C24 hydrocarbon group, and it is more preferable that it is a C6-C24 aromatic hydrocarbon group.
R3 및 R4가 서로 연결하여 고리를 형성하는 경우, R5 및 R6이 서로 연결하여 고리를 형성하는 것이 바람직하다.When R 3 and R 4 are connected to each other to form a ring, it is preferable that R 5 and R 6 are connected to each other to form a ring.
식 (I-A)로 표시되는 양이온은 식 (I-B)로 표시되는 양이온 또는 식 (I-C)로 표시되는 양이온인 것이 바람직하다.The cation represented by formula (I-A) is preferably a cation represented by formula (I-B) or a cation represented by formula (I-C).
[화학식 10][Formula 10]
Figure PCTKR2022010249-appb-I000010
Figure PCTKR2022010249-appb-I000010
[식 (I-B) 및 식 (I-C) 중,[In Formula (I-B) and Formula (I-C),
고리 W1, 고리 W2, R1 및 R2는 각각 상기와 동일한 의미를 나타낸다.Each of ring W 1 , ring W 2 , R 1 and R 2 has the same meaning as described above.
Ar1 및 Ar2는 각각 독립적으로 치환기를 가질 수 있는 탄소수 6 내지 24의 방향족 탄화수소기를 나타낸다.Ar 1 and Ar 2 each independently represent an aromatic hydrocarbon group having 6 to 24 carbon atoms which may have a substituent.
R4A 및 R6A는 각각 독립적으로 수소 원자 또는 치환기를 가질 수 있는 탄소수 6 내지 24의 탄화수소기를 나타낸다.R 4A and R 6A each independently represent a hydrogen atom or a hydrocarbon group having 6 to 24 carbon atoms which may have a substituent.
고리 W3 및 고리 W4는 각각 독립적으로 함질소 복소환기를 나타낸다.]Ring W 3 and Ring W 4 each independently represent a nitrogen-containing heterocyclic group.]
Ar1 및 Ar2로 나타나는 탄소수 6 내지 24의 방향족 탄화수소기는 R3으로 나타나는 방향족 탄화수소기와 동일한 것을 들 수 있다. Ar1 및 Ar2는 각각 독립적으로 탄소수 6 내지 24의 아릴기인 것이 바람직하고, 탄소수 6 내지 12의 아릴기인 것이 보다 바람직하다.The aromatic hydrocarbon group having 6 to 24 carbon atoms represented by Ar 1 and Ar 2 includes the same aromatic hydrocarbon group represented by R 3 . Ar 1 and Ar 2 are each independently preferably an aryl group having 6 to 24 carbon atoms, and more preferably an aryl group having 6 to 12 carbon atoms.
R4A 및 R6A로 나타나는 탄소수 6 내지 24의 탄화수소기로는 R3으로 나타나는 탄화수소기와 동일한 것을 들 수 있다. R4A 및 R6A는 각각 독립적으로 수소 원자 또는 탄소수 1 내지 24의 지방족 탄화수소기인 것이 바람직하고, 수소 원자 또는 탄소수 1 내지 24의 알킬기인 것이 보다 바람직하고, 수소 원자 또는 탄소수 1 내지 6의 알킬기인 것이 더욱 바람직하다.Examples of hydrocarbon groups having 6 to 24 carbon atoms represented by R 4A and R 6A include the same hydrocarbon groups represented by R 3 . R 4A and R 6A are each independently preferably a hydrogen atom or an aliphatic hydrocarbon group having 1 to 24 carbon atoms, more preferably a hydrogen atom or an alkyl group having 1 to 24 carbon atoms, and preferably a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. more preferable
Ar1, Ar2, R4A 및 R6A가 가질 수 있는 치환기로는 R3으로 나타나는 탄화수소기가 가질 수 있는 치환기를 들 수 있다.Substituents that Ar 1 , Ar 2 , R 4A and R 6A may have include substituents that the hydrocarbon group represented by R 3 may have.
고리 W3 및 고리 W4로 나타나는 함질소 복소환기는 단환일 수도 있으며, 축합환일 수도 있고, 축합환인 것이 바람직하다.The nitrogen-containing heterocyclic group represented by the ring W 3 and the ring W 4 may be a monocyclic ring or a condensed ring, preferably a condensed ring.
고리 W3 및 고리 W4는 각각 독립적으로 아제티딘 고리, 피롤리딘 고리, 피페리딘 고리, 모폴린 고리, 이미다졸린 고리, 피라졸 고리, 이미다졸 고리, 트리아졸 고리, 테트라졸 고리, 피페라진 고리, 티오모폴린 고리, 인돌린 고리인 것이 바람직하다.ring W 3 and ring W 4 are each independently an azetidine ring, a pyrrolidine ring, a piperidine ring, a morpholine ring, an imidazoline ring, a pyrazole ring, an imidazole ring, a triazole ring, a tetrazole ring, It is preferably a piperazine ring, a thiomorpholine ring, or an indoline ring.
식 (I-B)로 표시되는 양이온은 식 (I-B1)로 표시되는 양이온인 것이 바람직하고, 식 (I-C)로 표시되는 양이온은 식 (I-C1)로 표시되는 양이온인 것이 바람직하다.The cation represented by formula (I-B) is preferably a cation represented by formula (I-B1), and the cation represented by formula (I-C) is preferably a cation represented by formula (I-C1).
[화학식 11][Formula 11]
Figure PCTKR2022010249-appb-I000011
Figure PCTKR2022010249-appb-I000011
[식 (I-B1) 및 식 (I-C1) 중, 고리 W3, 고리 W4, R1, R2, R4A, R6A, Ar1 및 Ar2는 각각 상기와 동일한 의미를 나타낸다.][In formulas (I-B1) and (I-C1), ring W 3 , ring W 4 , R 1 , R 2 , R 4A , R 6A , Ar 1 and Ar 2 each have the same meaning as described above. ]
식 (I)로 표시되는 부분 구조를 포함하는 양이온으로는 예컨대 이하에 기재된 양이온을 들 수 있다.Examples of cations containing a partial structure represented by formula (I) include cations described below.
[화학식 12][Formula 12]
Figure PCTKR2022010249-appb-I000012
Figure PCTKR2022010249-appb-I000012
[화학식 13][Formula 13]
Figure PCTKR2022010249-appb-I000013
Figure PCTKR2022010249-appb-I000013
[화학식 14][Formula 14]
Figure PCTKR2022010249-appb-I000014
Figure PCTKR2022010249-appb-I000014
[화학식 15][Formula 15]
Figure PCTKR2022010249-appb-I000015
Figure PCTKR2022010249-appb-I000015
[화학식 16][Formula 16]
Figure PCTKR2022010249-appb-I000016
Figure PCTKR2022010249-appb-I000016
[화학식 17][Formula 17]
Figure PCTKR2022010249-appb-I000017
Figure PCTKR2022010249-appb-I000017
[화학식 18][Formula 18]
Figure PCTKR2022010249-appb-I000018
Figure PCTKR2022010249-appb-I000018
[화학식 19][Formula 19]
Figure PCTKR2022010249-appb-I000019
Figure PCTKR2022010249-appb-I000019
[화학식 20][Formula 20]
Figure PCTKR2022010249-appb-I000020
Figure PCTKR2022010249-appb-I000020
식 (I)로 표시되는 부분 구조를 갖는 양이온으로는 식 (I-1), 식 (I-2), 식 (I-3), 식 (I-4), 식 (I-8), 식 (I-12), 식 (I-13), 식 (I-17), 식 (I-18), 식 (I-23), 식 (I-25), 식 (I-26), 식 (I-27), 식 (I-28), 식 (I-29), 식 (I-31), 식 (I-38), 식 (I-60), 식 (I-61), 식 (I-62), 식 (I-79), 식 (I-80), 식 (I-85), 식 (I-87), 식 (I-90), 식 (I-93), 식 (I-94), 식 (I-95), 식 (I-96), 식 (I-101), 식 (I-103), 식 (I-105), 식 (I-107), 식 (I-128), 식 (I-133), 식 (I-135), 식 (I-137), 식 (I-139)로 표시되는 양이온인 것이 바람직하다.Cations having a partial structure represented by formula (I) include formula (I-1), formula (I-2), formula (I-3), formula (I-4), formula (I-8), formula (I-12), Formula (I-13), Formula (I-17), Formula (I-18), Formula (I-23), Formula (I-25), Formula (I-26), Formula ( I-27), Formula (I-28), Formula (I-29), Formula (I-31), Formula (I-38), Formula (I-60), Formula (I-61), Formula (I -62), Formula (I-79), Formula (I-80), Formula (I-85), Formula (I-87), Formula (I-90), Formula (I-93), Formula (I- 94), Formula (I-95), Formula (I-96), Formula (I-101), Formula (I-103), Formula (I-105), Formula (I-107), Formula (I-128) ), a cation represented by formula (I-133), formula (I-135), formula (I-137), or formula (I-139) is preferred.
<음이온><Anion>
화합물(I)은 통상적으로 식 (I)로 표시되는 양이온과 쌍이 되는 음이온으로 구성된다. 화합물(I)이 갖는 식 (I)로 표시되는 양이온과 음이온의 조합은 한정되지 않는다. 음이온의 가수가 2 이상인 경우, 식 (I)로 표시되는 양이온을 복수 개 가질 수 있다. 또한 음이온의 가수가 2 이상인 경우, 식 (I)로 표시되는 양이온과 식 (I)로 표시되는 양이온 이외의 양이온을 가질 수 있다.Compound (I) is usually composed of an anion paired with a cation represented by formula (I). The combination of the cation and anion represented by Formula (I) of Compound (I) is not limited. When the valence of an anion is 2 or more, it can have a plurality of cations represented by formula (I). Moreover, when the valence of an anion is 2 or more, it can have a cation other than the cation represented by Formula (I) and the cation represented by Formula (I).
음이온은 유기 음이온일 수도 있으며, 무기 음이온일 수도 있다.The anion may be an organic anion or an inorganic anion.
유기 음이온으로는 예컨대 아세테이트 음이온, 메티드 음이온, 아미드 음이온, 설포네이트 음이온 또는 보레이트 음이온 등을 들 수 있고, 메티드 음이온, 아미드 음이온, 설포네이트 음이온 또는 보레이트 음이온인 것이 바람직하다.Examples of the organic anion include acetate anion, methide anion, amide anion, sulfonate anion, or borate anion, and methide anion, amide anion, sulfonate anion, or borate anion is preferable.
메티드 음이온으로는 식 (c-A)로 표시되는 음이온인 것이 바람직하다.The methide anion is preferably an anion represented by formula (c-A).
[화학식 21][Formula 21]
Figure PCTKR2022010249-appb-I000021
Figure PCTKR2022010249-appb-I000021
[식 (c-A) 중, R1c, R2c 및 R3c는 각각 독립적으로 1가의 치환기를 나타낸다.][In Formula (cA), R 1c , R 2c and R 3c each independently represent a monovalent substituent.]
R1c, R2c 및 R3c로 나타나는 1가의 치환기는 특별히 한정되지 않지만, 불소 원자; 모노플루오로메틸기, 디플루오로메틸기, 트리플루오로메틸기, 테트라플루오로에틸기 등의 탄소수 1 내지 12의 플루오로알킬기; 모노플루오로페닐기, 테트라플루오로페닐기 등의 탄소수 6 내지 18의 플루오로아릴기; 시아노기; 니트로기; -SO2-R11c(R11c는 불소 원자를 가질 수 있는 탄소수 1 내지 12의 탄화수소기를 나타낸다.)인 것이 바람직하다.The monovalent substituent represented by R 1c , R 2c and R 3c is not particularly limited, but is fluorine atom; fluoroalkyl groups having 1 to 12 carbon atoms such as a monofluoromethyl group, a difluoromethyl group, a trifluoromethyl group, and a tetrafluoroethyl group; fluoroaryl groups having 6 to 18 carbon atoms, such as a monofluorophenyl group and a tetrafluorophenyl group; cyano group; nitro group; It is preferably -SO 2 -R 11c (R 11c represents a hydrocarbon group having 1 to 12 carbon atoms which may have a fluorine atom).
아미드 음이온으로는 식 (c-B)로 표시되는 음이온인 것이 바람직하다.The amide anion is preferably an anion represented by formula (c-B).
[화학식 22][Formula 22]
Figure PCTKR2022010249-appb-I000022
Figure PCTKR2022010249-appb-I000022
[식 (c-B) 중, R4c 및 R5c는 각각 독립적으로 1가의 치환기를 나타낸다.][In formula (cB), R 4c and R 5c each independently represent a monovalent substituent.]
R4c 및 R5c로 나타나는 1가의 치환기는 특별히 한정되지 않지만, 불소 원자; 모노플루오로메틸기, 디플루오로메틸기, 트리플루오로메틸기, 테트라플루오로에틸기 등의 탄소수 1 내지 12의 플루오로알킬기; 모노플루오로페닐기, 테트라플루오로페닐기 등의 탄소수 6 내지 18의 플루오로아릴기; 시아노기; 니트로기; -SO2-R11c(R11c는 불소 원자를 가질 수 있는 탄소수 1 내지 12의 탄화수소기를 나타낸다.)인 것이 바람직하다.The monovalent substituent represented by R 4c and R 5c is not particularly limited, but is fluorine atom; fluoroalkyl groups having 1 to 12 carbon atoms such as a monofluoromethyl group, a difluoromethyl group, a trifluoromethyl group, and a tetrafluoroethyl group; fluoroaryl groups having 6 to 18 carbon atoms, such as a monofluorophenyl group and a tetrafluorophenyl group; cyano group; nitro group; It is preferably -SO 2 -R 11c (R 11c represents a hydrocarbon group having 1 to 12 carbon atoms which may have a fluorine atom).
설포네이트 음이온으로는 식 (c-C)로 표시되는 음이온인 것이 바람직하다.As the sulfonate anion, an anion represented by the formula (c-C) is preferable.
[화학식 23][Formula 23]
Figure PCTKR2022010249-appb-I000023
Figure PCTKR2022010249-appb-I000023
[식 (c-C) 중, R6c는 1가의 치환기를 나타낸다.][In formula (cC), R 6c represents a monovalent substituent.]
R6c로 나타나는 1가의 치환기는 특별히 한정되지 않지만, 불소 원자; 모노플루오로메틸기, 디플루오로메틸기, 트리플루오로메틸기, 테트라플루오로에틸기 등의 탄소수 1 내지 12의 플루오로알킬기; 모노플루오로페닐기, 테트라플루오로페닐기 등의 탄소수 6 내지 18의 플루오로아릴기; 시아노기; 니트로기; -SO2-R11c(R11c는 불소 원자를 가질 수 있는 탄소수 1 내지 12의 탄화수소기를 나타낸다.)인 것이 바람직하다.The monovalent substituent represented by R 6c is not particularly limited, but is fluorine atom; fluoroalkyl groups having 1 to 12 carbon atoms such as a monofluoromethyl group, a difluoromethyl group, a trifluoromethyl group, and a tetrafluoroethyl group; fluoroaryl groups having 6 to 18 carbon atoms, such as a monofluorophenyl group and a tetrafluorophenyl group; cyano group; nitro group; It is preferably -SO 2 -R 11c (R 11c represents a hydrocarbon group having 1 to 12 carbon atoms which may have a fluorine atom).
보레이트 음이온으로는 식 (c-D)로 표시되는 음이온인 것이 바람직하다.The borate anion is preferably an anion represented by formula (c-D).
[화학식 24][Formula 24]
Figure PCTKR2022010249-appb-I000024
Figure PCTKR2022010249-appb-I000024
[식 (c-D) 중, R7c, R8c, R9c 및 R10c는 각각 독립적으로 1가의 치환기를 나타낸다.][In Formula (cD), R 7c , R 8c , R 9c and R 10c each independently represent a monovalent substituent.]
R7c, R8c, R9c 및 R10c로 나타나는 1가의 치환기는 특별히 한정되지 않지만, 불소 원자; 모노플루오로메틸기, 디플루오로메틸기, 트리플루오로메틸기, 테트라플루오로에틸기 등의 탄소수 1 내지 12의 플루오로알킬기; 모노플루오로페닐기, 테트라플루오로페닐기 등의 탄소수 6 내지 18의 플루오로아릴기; 시아노기; 니트로기; -SO2-R11c(R11c는 불소 원자를 가질 수 있는 탄소수 1 내지 12의 탄화수소기를 나타낸다.)인 것이 바람직하다.The monovalent substituent represented by R 7c , R 8c , R 9c and R 10c is not particularly limited, but is fluorine atom; fluoroalkyl groups having 1 to 12 carbon atoms such as a monofluoromethyl group, a difluoromethyl group, a trifluoromethyl group, and a tetrafluoroethyl group; fluoroaryl groups having 6 to 18 carbon atoms, such as a monofluorophenyl group and a tetrafluorophenyl group; cyano group; nitro group; It is preferably -SO 2 -R 11c (R 11c represents a hydrocarbon group having 1 to 12 carbon atoms which may have a fluorine atom).
식 (c-A)로 표시되는 음이온은 식 (c-A1)로 표시되는 음이온인 것이 바람직하고,The anion represented by formula (c-A) is preferably an anion represented by formula (c-A1),
식 (c-B)로 표시되는 음이온은 식 (c-B1)로 표시되는 음이온인 것이 바람직하고,The anion represented by formula (c-B) is preferably an anion represented by formula (c-B1),
식 (c-C)로 표시되는 음이온은 식 (c-C1)로 표시되는 음이온인 것이 바람직하고,The anion represented by formula (c-C) is preferably an anion represented by formula (c-C1),
식 (c-D)로 표시되는 음이온은 식 (c-D1)로 표시되는 음이온 또는 식 (c-D2)로 표시되는 음이온인 것이 바람직하다.The anion represented by formula (c-D) is preferably an anion represented by formula (c-D1) or an anion represented by formula (c-D2).
[화학식 25][Formula 25]
Figure PCTKR2022010249-appb-I000025
Figure PCTKR2022010249-appb-I000025
[식 (c-A1) 중, Rf1, Rf2 및 Rf3은 각각 독립적으로 탄소수 1 내지 12의 플루오로알킬기를 나타낸다.[In formula (c-A1), Rf 1 , Rf 2 and Rf 3 each independently represent a fluoroalkyl group having 1 to 12 carbon atoms.
식 (c-B1) 중, Rf4 및 Rf5는 각각 독립적으로 불소 원자 또는 탄소수 1 내지 12의 플루오로알킬기를 나타낸다.In formula (c-B1), Rf 4 and Rf 5 each independently represent a fluorine atom or a fluoroalkyl group having 1 to 12 carbon atoms.
식 (c-C1) 중, Rf6은 탄소수 1 내지 12의 플루오로알킬기를 나타낸다.In formula (c-C1), Rf 6 represents a fluoroalkyl group having 1 to 12 carbon atoms.
식 (c-D2) 중, R1d, R2d, R3d 및 R4d는 각각 독립적으로 불소 원자 또는 탄소수 1 내지 12의 플루오로알킬기를 나타낸다. n1 내지 n4는 각각 독립적으로 0 내지 5의 정수를 나타낸다.]In formula (c-D2), R 1d , R 2d , R 3d and R 4d each independently represent a fluorine atom or a fluoroalkyl group having 1 to 12 carbon atoms. n1 to n4 each independently represent an integer of 0 to 5.]
보다 구체적인 유기 음이온으로는 예컨대 아세테이트 음이온〔CH3COO-〕, 트리플루오로아세테이트 음이온〔CF3COO-〕, 메탄설포네이트 음이온〔CH3SO3 -〕, 트리플루오로메탄설포네이트 음이온〔CF3SO3 -〕, p-톨루엔설포네이트 음이온〔p-CH3C6H4SO3 -〕, 비스(트리플루오로메탄설포닐)이미드 음이온〔(CF3SO2)2N-〕, 비스(노나플루오로부틸설포닐)이미드 음이온〔(C4F9SO2)2N-〕, 트리스(트리플루오로메탄설포닐)메타니드 음이온〔(CF3SO2)3C-〕, 디메틸포스피네이트 음이온〔(CH3)2POO-〕, (폴리)히드로플루오로플루오라이드 음이온〔F(HF)m -〕(m은 1 이상 3 이하 정도), 퍼플루오로부탄설포네이트 음이온〔C4F9SO3 -〕, 비스(펜타플루오로에탄설포닐)이미드 음이온〔(C2F5SO2)2N-〕, 퍼플루오로부타노에이트 음이온〔C3F7COO-〕, (트리플루오로메탄설포닐)(트리플루오로메탄카보닐)이미드 음이온〔(CF3SO2)(CF3CO)N-〕, 퍼플루오로프로판-1,3-디설포네이트 음이온〔-O3S (CF2)3SO3 -〕, 카보네이트 음이온〔CO3 2-〕, 테트라시아노보레이트, 테트라키스(펜타플루오로페닐)보레이트, 테트라키스페닐보레이트, 트리스(펜타플루오로에틸)트리플루오로포스페이트[P-(C2F5)3F3] 등을 들 수 있다.More specific organic anions include, for example, acetate anion [CH 3 COO - ], trifluoroacetate anion [CF 3 COO - ], methanesulfonate anion [CH 3 SO 3 - ], trifluoromethanesulfonate anion [CF 3 SO 3 - ], p-toluenesulfonate anion [p-CH 3 C 6 H 4 SO 3 - ], bis(trifluoromethanesulfonyl)imide anion [(CF 3 SO 2 ) 2 N - ], bis (Nonafluorobutylsulfonyl)imide anion [(C 4 F 9 SO 2 ) 2 N - ], tris(trifluoromethanesulfonyl)methanide anion [(CF 3 SO 2 ) 3 C - ], dimethyl Phosphinate anion [(CH 3 ) 2 POO - ], (poly)hydrofluorofluoride anion [F(HF) m - ] (m is approximately 1 or more and 3 or less), perfluorobutanesulfonate anion [C 4 F 9 SO 3 - ], bis(pentafluoroethanesulfonyl)imide anion [(C 2 F 5 SO 2 ) 2 N - ], perfluorobutanoate anion [C 3 F 7 COO - ], (trifluoromethanesulfonyl)(trifluoromethanecarbonyl)imide anion [(CF 3 SO 2 )(CF 3 CO)N - ], perfluoropropane-1,3-disulfonate anion [ - O 3 S (CF 2 ) 3 SO 3 - ], carbonate anion [CO 3 2- ], tetracyanoborate, tetrakis(pentafluorophenyl)borate, tetrakisphenylborate, tris(pentafluoroethyl)tris fluorophosphate [P- ( C 2 F 5 ) 3 F 3 ]; and the like.
무기 음이온으로는 예컨대 플루오라이드 음이온, 클로라이드 음이온, 브로미드 음이온, 요오다이드 음이온, 테트라클로로알루미네이트 음이온〔AlCl4 -〕, 헵타클로로디알루미네이트 음이온〔Al2Cl7 -〕, 테트라플루오로보레이트 음이온〔BF4 -〕, 헥사플루오로포스페이트 음이온〔PF6 -〕, 퍼클로레이트 음이온〔ClO4 -〕, 나이트레이트 음이온〔NO3 -〕, 헥사플루오로아르세네이트 음이온〔AsF6 -〕, 헥사플루오로안티모네이트 음이온〔SbF6 -〕, 헥사플루오로니오베이트 음이온〔NbF6 -〕, 헥사플루오로탄탈레이트 음이온〔TaF6 -〕, 디시안아미드 음이온〔(CN)2N-〕, 비스(플루오로설포닐)이미드 음이온[(FSO2)2N-], 인산 음이온(PO4 3-), 티오시안 음이온〔SCN-〕 등을 들 수 있다.Inorganic anions include, for example, fluoride anion, chloride anion, bromide anion, iodide anion, tetrachloroaluminate anion [AlCl 4 - ], heptachlorodialuminate anion [Al 2 Cl 7 - ], tetrafluoroborate anion [BF 4 - ], hexafluorophosphate anion [PF 6 - ], perchlorate anion [ClO 4 - ], nitrate anion [NO 3 - ], hexafluoroarsenate anion [AsF 6 - ], hexafluoro Roantimonate anion [SbF 6 - ], hexafluoroniobate anion [NbF 6 - ], hexafluorotantalate anion [TaF 6 - ], dicyanamide anion [(CN) 2 N - ], bis( fluorosulfonyl)imide anion [(FSO 2 ) 2 N - ], phosphoric acid anion (PO 4 3- ), thiocyanate anion [SCN - ] and the like.
무기 음이온으로는 비스(플루오로설포닐)이미드 음이온(N-(SO2F)2)인 것이 바람직하다. 유기 음이온으로는 트리플루오로아세테이트 음이온〔CF3COO-〕, 트리플루오로메탄설포네이트 음이온〔CF3SO3 -〕, 비스(트리플루오로메탄설포닐)이미드 음이온〔(CF3SO2)2N-〕, 트리스(트리플루오로메탄설포닐)메타니드 음이온〔(CF3SO2)3C-〕, 퍼플루오로부탄설포네이트 음이온〔C4F9SO3 -〕, 비스(펜타플루오로에탄설포닐)이미드 음이온〔(C2F5SO2)2N-〕, 퍼플루오로부타노에이트 음이온〔C3F7COO-〕, (트리플루오로메탄설포닐)(트리플루오로메탄카보닐)이미드 음이온〔(CF3SO2)(CF3CO)N-〕, 퍼플루오로프로판-1,3-디설포네이트 음이온〔-O3S(CF2)3SO3 -〕, 테트라키스아릴보레이트 음이온(테트라키스페닐보레이트, 테트라키스(펜타플루오로페닐)보레이트), 테트라시아노보레이트가 바람직하고, 더욱 바람직하게 비스(트리플루오로메탄설포닐)이미드 음이온〔(CF3SO2)2N-〕, 트리스(트리플루오로메탄설포닐)메타니드 음이온〔(CF3SO2)3C-〕, 테트라키스(펜타플루오로페닐)보레이트, 테트라시아노보레이트이며, 특히 바람직하게 테트라키스(펜타플루오로페닐)보레이트이다.The inorganic anion is preferably a bis(fluorosulfonyl)imide anion (N - (SO 2 F) 2 ). Examples of organic anions include trifluoroacetate anion [CF 3 COO - ], trifluoromethanesulfonate anion [CF 3 SO 3 - ], bis(trifluoromethanesulfonyl)imide anion [(CF 3 SO 2 ) 2 N - ], tris (trifluoromethanesulfonyl)methanide anion [(CF 3 SO 2 ) 3 C - ], perfluorobutanesulfonate anion [C 4 F 9 SO 3 - ], bis(pentafluoro Roethanesulfonyl) imide anion [(C 2 F 5 SO 2 ) 2 N - ], perfluorobutanoate anion [C 3 F 7 COO - ], (trifluoromethanesulfonyl) (trifluoro Methanecarbonyl)imide anion [(CF 3 SO 2 )(CF 3 CO)N - ], perfluoropropane-1,3-disulfonate anion [ - O 3 S(CF 2 ) 3 SO 3 - ] , tetrakisarylborate anion (tetrakisphenylborate, tetrakis(pentafluorophenyl)borate) and tetracyanoborate are preferred, more preferably bis(trifluoromethanesulfonyl)imide anion [(CF 3 SO 2 ) 2 N - ], tris (trifluoromethanesulfonyl) metanide anion [(CF 3 SO 2 ) 3 C - ], tetrakis (pentafluorophenyl) borate, tetracyanoborate, particularly preferred. It is tetrakis(pentafluorophenyl)borate.
화합물(I)로는 예컨대 이하 표 1 내지 표 8에 기재된 화합물을 들 수 있다. 또, 표 1에서의 화합물(1)은 식 (I-1)로 표시되는 양이온과 클로라이드 음이온을 포함하는 화합물이며, 하기에 기재된 화합물이다.Examples of Compound (I) include compounds listed in Tables 1 to 8 below. In addition, compound (1) in Table 1 is a compound containing a cation represented by formula (I-1) and a chloride anion, and is a compound described below.
[화학식 26][Formula 26]
Figure PCTKR2022010249-appb-I000026
Figure PCTKR2022010249-appb-I000026
번호number 양이온cation 음이온anion
화합물(1)Compound (1) 식 (I-1)Formula (I-1) Cl- Cl -
화합물(2)Compound (2) 식 (I-2)Formula (I-2) Cl－ Cl -
화합물(3)compound (3) 식 (I-3)Formula (I-3) Cl－ Cl -
화합물(4)compound (4) 식 (I-4)Formula (I-4) Cl－ Cl -
화합물(5)compound (5) 식 (I-8)Formula (I-8) Cl－ Cl -
화합물(6)compound (6) 식 (I-12)Formula (I-12) Cl－ Cl -
화합물(7)compound (7) 식 (I-13)Formula (I-13) Cl－ Cl -
화합물(8)compound (8) 식 (I-17)Formula (I-17) Cl－ Cl -
화합물(9)Compound (9) 식 (I-18)Formula (I-18) Cl－ Cl -
화합물(10)compound (10) 식 (I-23)Formula (I-23) Cl－ Cl -
화합물(11)Compound (11) 식 (I-25)Formula (I-25) Cl－ Cl -
화합물(12)Compound (12) 식 (I-26)Formula (I-26) Cl－ Cl -
화합물(13)Compound (13) 식 (I-27)Formula (I-27) Cl－ Cl -
화합물(14)Compound (14) 식 (I-28)Formula (I-28) Cl－ Cl -
화합물(15)Compound (15) 식 (I-29)Formula (I-29) Cl－ Cl -
화합물(16)Compound (16) 식 (I-31)Formula (I-31) Cl－ Cl -
화합물(17)compound (17) 식 (I-38)Formula (I-38) Cl－ Cl -
화합물(18)Compound (18) 식 (I-60)Formula (I-60) Cl－ Cl -
화합물(19)Compound (19) 식 (I-61)Formula (I-61) Cl－ Cl -
화합물(20)compound (20) 식 (I-62)Formula (I-62) Cl－ Cl -
화합물(21)Compound (21) 식 (I-79)Formula (I-79) Cl－ Cl -
화합물(22)Compound (22) 식 (I-80)Formula (I-80) Cl－ Cl -
화합물(23)Compound (23) 식 (I-85)Formula (I-85) Cl－ Cl -
화합물(24)Compound (24) 식 (I-87)Formula (I-87) Cl－ Cl -
화합물(25)compound (25) 식 (I-90)Formula (I-90) Cl－ Cl -
화합물(26)Compound (26) 식 (I-93)Formula (I-93) Cl－ Cl -
화합물(27)compound (27) 식 (I-94)Formula (I-94) Cl－ Cl -
화합물(28)Compound (28) 식 (I-95)Formula (I-95) Cl－ Cl -
화합물(29)compound (29) 식 (I-96)Formula (I-96) Cl－ Cl -
화합물(30)compound (30) 식 (I-101)Formula (I-101) Cl－ Cl -
화합물(31)Compound (31) 식 (I-103)Formula (I-103) Cl－ Cl -
화합물(32)Compound (32) 식 (I-105)Formula (I-105) Cl－ Cl -
화합물(33)Compound (33) 식 (I-107)Formula (I-107) Cl－ Cl -
화합물(34)Compound (34) 식 (I-128)Formula (I-128) Cl－ Cl -
화합물(35)Compound (35) 식 (I-133)Formula (I-133) Cl－ Cl -
화합물(36)Compound (36) 식 (I-135)Formula (I-135) Cl－ Cl -
화합물(37)Compound (37) 식 (I-137)Formula (I-137) Cl－ Cl -
화합물(38)Compound (38) 식 (I-139)Formula (I-139) Cl－ Cl -
번호number 양이온cation 음이온anion
화합물(39)Compound (39) 식 (I-1)Formula (I-1) (FSO2)2N- (FSO 2 ) 2 N -
화합물(40)compound (40) 식 (I-2)Formula (I-2) (FSO2)2N- (FSO 2 ) 2 N -
화합물(41)Compound (41) 식 (I-3)Formula (I-3) (FSO2)2N- (FSO 2 ) 2 N -
화합물(42)compound (42) 식 (I-4)Formula (I-4) (FSO2)2N- (FSO 2 ) 2 N -
화합물(43)compound (43) 식 (I-8)Formula (I-8) (FSO2)2N- (FSO 2 ) 2 N -
화합물(44)compound (44) 식 (I-12)Formula (I-12) (FSO2)2N- (FSO 2 ) 2 N -
화합물(45)Compound (45) 식 (I-13)Formula (I-13) (FSO2)2N- (FSO 2 ) 2 N -
화합물(46)compound (46) 식 (I-17)Formula (I-17) (FSO2)2N- (FSO 2 ) 2 N -
화합물(47)compound (47) 식 (I-18)Formula (I-18) (FSO2)2N- (FSO 2 ) 2 N -
화합물(48)Compound (48) 식 (I-23)Formula (I-23) (FSO2)2N- (FSO 2 ) 2 N -
화합물(49)compound (49) 식 (I-25)Formula (I-25) (FSO2)2N- (FSO 2 ) 2 N -
화합물(50)compound (50) 식 (I-26)Formula (I-26) (FSO2)2N- (FSO 2 ) 2 N -
화합물(51)Compound (51) 식 (I-27)Formula (I-27) (FSO2)2N- (FSO 2 ) 2 N -
화합물(52)compound (52) 식 (I-28)Formula (I-28) (FSO2)2N- (FSO 2 ) 2 N -
화합물(53)compound (53) 식 (I-29)Formula (I-29) (FSO2)2N- (FSO 2 ) 2 N -
화합물(54)Compound (54) 식 (I-31)Formula (I-31) (FSO2)2N- (FSO 2 ) 2 N -
화합물(55)Compound (55) 식 (I-38)Formula (I-38) (FSO2)2N- (FSO 2 ) 2 N -
화합물(56)compound (56) 식 (I-60)Formula (I-60) (FSO2)2N- (FSO 2 ) 2 N -
화합물(57)compound (57) 식 (I-61)Formula (I-61) (FSO2)2N- (FSO 2 ) 2 N -
화합물(58)Compound (58) 식 (I-62)Formula (I-62) (FSO2)2N- (FSO 2 ) 2 N -
화합물(59)compound (59) 식 (I-79)Formula (I-79) (FSO2)2N- (FSO 2 ) 2 N -
화합물(60)compound (60) 식 (I-80)Formula (I-80) (FSO2)2N- (FSO 2 ) 2 N -
화합물(61)compound (61) 식 (I-85)Formula (I-85) (FSO2)2N- (FSO 2 ) 2 N -
화합물(62)compound (62) 식 (I-87)Formula (I-87) (FSO2)2N- (FSO 2 ) 2 N -
화합물(63)compound (63) 식 (I-90)Formula (I-90) (FSO2)2N- (FSO 2 ) 2 N -
화합물(64)compound (64) 식 (I-93)Formula (I-93) (FSO2)2N- (FSO 2 ) 2 N -
화합물(65)compound (65) 식 (I-94)Formula (I-94) (FSO2)2N- (FSO 2 ) 2 N -
화합물(66)compound (66) 식 (I-95)Formula (I-95) (FSO2)2N- (FSO 2 ) 2 N -
화합물(67)compound (67) 식 (I-96)Formula (I-96) (FSO2)2N- (FSO 2 ) 2 N -
화합물(68)Compound (68) 식 (I-101)Formula (I-101) (FSO2)2N- (FSO 2 ) 2 N -
화합물(69)compound (69) 식 (I-103)Formula (I-103) (FSO2)2N- (FSO 2 ) 2 N -
화합물(70)compound (70) 식 (I-105)Formula (I-105) (FSO2)2N- (FSO 2 ) 2 N -
화합물(71)compound (71) 식 (I-107)Formula (I-107) (FSO2)2N- (FSO 2 ) 2 N -
화합물(72)compound (72) 식 (I-128)Formula (I-128) (FSO2)2N- (FSO 2 ) 2 N -
화합물(73)compound (73) 식 (I-133)Formula (I-133) (FSO2)2N- (FSO 2 ) 2 N -
화합물(74)compound (74) 식 (I-135)Formula (I-135) (FSO2)2N- (FSO 2 ) 2 N -
화합물(75)Compound (75) 식 (I-137)Formula (I-137) (FSO2)2N- (FSO 2 ) 2 N -
화합물(76)compound (76) 식 (I-139)Formula (I-139) (FSO2)2N- (FSO 2 ) 2 N -
번호number 양이온cation 음이온anion
화합물(77)compound (77) 식 (I-1)Formula (I-1) CF3SO3 - CF 3 SO 3 -
화합물(78)Compound (78) 식 (I-2)Formula (I-2) CF3SO3 - CF 3 SO 3 -
화합물(79)compound (79) 식 (I-3)Formula (I-3) CF3SO3 - CF 3 SO 3 -
화합물(80)compound (80) 식 (I-4)Formula (I-4) CF3SO3 - CF 3 SO 3 -
화합물(81)Compound (81) 식 (I-8)Formula (I-8) CF3SO3 - CF 3 SO 3 -
화합물(82)Compound (82) 식 (I-12)Formula (I-12) CF3SO3 - CF 3 SO 3 -
화합물(83)compound (83) 식 (I-13)Formula (I-13) CF3SO3 - CF 3 SO 3 -
화합물(84)Compound (84) 식 (I-17)Formula (I-17) CF3SO3 - CF 3 SO 3 -
화합물(85)compound (85) 식 (I-18)Formula (I-18) CF3SO3 - CF 3 SO 3 -
화합물(86)compound (86) 식 (I-23)Formula (I-23) CF3SO3 - CF 3 SO 3 -
화합물(87)compound (87) 식 (I-25)Formula (I-25) CF3SO3 - CF 3 SO 3 -
화합물(88)Compound (88) 식 (I-26)Formula (I-26) CF3SO3 - CF 3 SO 3 -
화합물(89)compound (89) 식 (I-27)Formula (I-27) CF3SO3 - CF 3 SO 3 -
화합물(90)compound (90) 식 (I-28)Formula (I-28) CF3SO3 - CF 3 SO 3 -
화합물(91)Compound (91) 식 (I-29)Formula (I-29) CF3SO3 - CF 3 SO 3 -
화합물(92)Compound (92) 식 (I-31)Formula (I-31) CF3SO3 - CF 3 SO 3 -
화합물(93)compound (93) 식 (I-38)Formula (I-38) CF3SO3 - CF 3 SO 3 -
화합물(94)Compound (94) 식 (I-60)Formula (I-60) CF3SO3 - CF 3 SO 3 -
화합물(95)compound (95) 식 (I-61)Formula (I-61) CF3SO3 - CF 3 SO 3 -
화합물(96)Compound (96) 식 (I-62)Formula (I-62) CF3SO3 - CF 3 SO 3 -
화합물(97)compound (97) 식 (I-79)Formula (I-79) CF3SO3 - CF 3 SO 3 -
화합물(98)Compound (98) 식 (I-80)Formula (I-80) CF3SO3 - CF 3 SO 3 -
화합물(99)compound (99) 식 (I-85)Formula (I-85) CF3SO3 - CF 3 SO 3 -
화합물(100)compound (100) 식 (I-87)Formula (I-87) CF3SO3 - CF 3 SO 3 -
화합물(101)compound (101) 식 (I-90)Formula (I-90) CF3SO3 - CF 3 SO 3 -
화합물(102)compound (102) 식 (I-93)Formula (I-93) CF3SO3 - CF 3 SO 3 -
화합물(103)compound (103) 식 (I-94)Formula (I-94) CF3SO3 - CF 3 SO 3 -
화합물(104)compound (104) 식 (I-95)Formula (I-95) CF3SO3 - CF 3 SO 3 -
화합물(105)compound (105) 식 (I-96)Formula (I-96) CF3SO3 - CF 3 SO 3 -
화합물(106)compound (106) 식 (I-101)Formula (I-101) CF3SO3 - CF 3 SO 3 -
화합물(107)compound (107) 식 (I-103)Formula (I-103) CF3SO3 - CF 3 SO 3 -
화합물(108)Compound (108) 식 (I-105)Formula (I-105) CF3SO3 - CF 3 SO 3 -
화합물(109)compound (109) 식 (I-107)Formula (I-107) CF3SO3 - CF 3 SO 3 -
화합물(110)compound (110) 식 (I-128)Formula (I-128) CF3SO3 - CF 3 SO 3 -
화합물(111)compound (111) 식 (I-133)Formula (I-133) CF3SO3 - CF 3 SO 3 -
화합물(112)compound (112) 식 (I-135)Formula (I-135) CF3SO3 - CF 3 SO 3 -
화합물(113)compound (113) 식 (I-137)Formula (I-137) CF3SO3 - CF 3 SO 3 -
화합물(114)compound (114) 식 (I-139)Formula (I-139) CF3SO3 - CF 3 SO 3 -
번호number 양이온cation 음이온anion
화합물(115)compound (115) 식 (I-1)Formula (I-1) (CF3SO2)2N- (CF 3 SO 2 ) 2 N -
화합물(116)compound (116) 식 (I-2)Formula (I-2) (CF3SO2)2N- (CF 3 SO 2 ) 2 N -
화합물(117)compound (117) 식 (I-3)Formula (I-3) (CF3SO2)2N- (CF 3 SO 2 ) 2 N -
화합물(118)compound (118) 식 (I-4)Formula (I-4) (CF3SO2)2N- (CF 3 SO 2 ) 2 N -
화합물(119)compound (119) 식 (I-8)Formula (I-8) (CF3SO2)2N- (CF 3 SO 2 ) 2 N -
화합물(120)compound (120) 식 (I-12)Formula (I-12) (CF3SO2)2N- (CF 3 SO 2 ) 2 N -
화합물(121)compound (121) 식 (I-13)Formula (I-13) (CF3SO2)2N- (CF 3 SO 2 ) 2 N -
화합물(122)compound (122) 식 (I-17)Formula (I-17) (CF3SO2)2N- (CF 3 SO 2 ) 2 N -
화합물(123)compound (123) 식 (I-18)Formula (I-18) (CF3SO2)2N- (CF 3 SO 2 ) 2 N -
화합물(124)compound (124) 식 (I-23)Formula (I-23) (CF3SO2)2N- (CF 3 SO 2 ) 2 N -
화합물(125)compound (125) 식 (I-25)Formula (I-25) (CF3SO2)2N- (CF 3 SO 2 ) 2 N -
화합물(126)compound (126) 식 (I-26)Formula (I-26) (CF3SO2)2N- (CF 3 SO 2 ) 2 N -
화합물(127)compound (127) 식 (I-27)Formula (I-27) (CF3SO2)2N- (CF 3 SO 2 ) 2 N -
화합물(128)compound (128) 식 (I-28)Formula (I-28) (CF3SO2)2N- (CF 3 SO 2 ) 2 N -
화합물(129)compound (129) 식 (I-29)Formula (I-29) (CF3SO2)2N- (CF 3 SO 2 ) 2 N -
화합물(130)compound (130) 식 (I-31)Formula (I-31) (CF3SO2)2N- (CF 3 SO 2 ) 2 N -
화합물(131)compound (131) 식 (I-38)Formula (I-38) (CF3SO2)2N- (CF 3 SO 2 ) 2 N -
화합물(132)compound (132) 식 (I-60)Formula (I-60) (CF3SO2)2N- (CF 3 SO 2 ) 2 N -
화합물(133)compound (133) 식 (I-61)Formula (I-61) (CF3SO2)2N- (CF 3 SO 2 ) 2 N -
화합물(134)compound (134) 식 (I-62)Formula (I-62) (CF3SO2)2N- (CF 3 SO 2 ) 2 N -
화합물(135)compound (135) 식 (I-79)Formula (I-79) (CF3SO2)2N- (CF 3 SO 2 ) 2 N -
화합물(136)compound (136) 식 (I-80)Formula (I-80) (CF3SO2)2N- (CF 3 SO 2 ) 2 N -
화합물(137)compound (137) 식 (I-85)Formula (I-85) (CF3SO2)2N- (CF 3 SO 2 ) 2 N -
화합물(138)compound (138) 식 (I-87)Formula (I-87) (CF3SO2)2N- (CF 3 SO 2 ) 2 N -
화합물(139)compound (139) 식 (I-90)Formula (I-90) (CF3SO2)2N- (CF 3 SO 2 ) 2 N -
화합물(140)compound (140) 식 (I-93)Formula (I-93) (CF3SO2)2N- (CF 3 SO 2 ) 2 N -
화합물(141)compound (141) 식 (I-94)Formula (I-94) (CF3SO2)2N- (CF 3 SO 2 ) 2 N -
화합물(142)compound (142) 식 (I-95)Formula (I-95) (CF3SO2)2N- (CF 3 SO 2 ) 2 N -
화합물(143)compound (143) 식 (I-96)Formula (I-96) (CF3SO2)2N- (CF 3 SO 2 ) 2 N -
화합물(144)compound (144) 식 (I-101)Formula (I-101) (CF3SO2)2N- (CF 3 SO 2 ) 2 N -
화합물(145)compound (145) 식 (I-103)Formula (I-103) (CF3SO2)2N- (CF 3 SO 2 ) 2 N -
화합물(146)compound (146) 식 (I-105)Formula (I-105) (CF3SO2)2N- (CF 3 SO 2 ) 2 N -
화합물(147)compound (147) 식 (I-107)Formula (I-107) (CF3SO2)2N- (CF 3 SO 2 ) 2 N -
화합물(148)compound (148) 식 (I-128)Formula (I-128) (CF3SO2)2N- (CF 3 SO 2 ) 2 N -
화합물(149)compound (149) 식 (I-133)Formula (I-133) (CF3SO2)2N- (CF 3 SO 2 ) 2 N -
화합물(150)compound (150) 식 (I-135)Formula (I-135) (CF3SO2)2N- (CF 3 SO 2 ) 2 N -
화합물(151)compound (151) 식 (I-137)Formula (I-137) (CF3SO2)2N- (CF 3 SO 2 ) 2 N -
화합물(152)compound (152) 식 (I-139)Formula (I-139) (CF3SO2)2N- (CF 3 SO 2 ) 2 N -
번호number 양이온cation 음이온anion
화합물(153)compound (153) 식 (I-1)Formula (I-1) (CF3SO2)3C- (CF 3 SO 2 ) 3 C -
화합물(154)compound (154) 식 (I-2)Formula (I-2) (CF3SO2)3C- (CF 3 SO 2 ) 3 C -
화합물(155)compound (155) 식 (I-3)Formula (I-3) (CF3SO2)3C- (CF 3 SO 2 ) 3 C -
화합물(156)compound (156) 식 (I-4)Formula (I-4) (CF3SO2)3C- (CF 3 SO 2 ) 3 C -
화합물(157)compound (157) 식 (I-8)Formula (I-8) (CF3SO2)3C- (CF 3 SO 2 ) 3 C -
화합물(158)compound (158) 식 (I-12)Formula (I-12) (CF3SO2)3C- (CF 3 SO 2 ) 3 C -
화합물(159)compound (159) 식 (I-13)Formula (I-13) (CF3SO2)3C- (CF 3 SO 2 ) 3 C -
화합물(160)compound (160) 식 (I-17)Formula (I-17) (CF3SO2)3C- (CF 3 SO 2 ) 3 C -
화합물(161)compound (161) 식 (I-18)Formula (I-18) (CF3SO2)3C- (CF 3 SO 2 ) 3 C -
화합물(162)compound (162) 식 (I-23)Formula (I-23) (CF3SO2)3C- (CF 3 SO 2 ) 3 C -
화합물(163)compound (163) 식 (I-25)Formula (I-25) (CF3SO2)3C- (CF 3 SO 2 ) 3 C -
화합물(164)compound (164) 식 (I-26)Formula (I-26) (CF3SO2)3C- (CF 3 SO 2 ) 3 C -
화합물(165)compound (165) 식 (I-27)Formula (I-27) (CF3SO2)3C- (CF 3 SO 2 ) 3 C -
화합물(166)compound (166) 식 (I-28)Formula (I-28) (CF3SO2)3C- (CF 3 SO 2 ) 3 C -
화합물(167)compound (167) 식 (I-29)Formula (I-29) (CF3SO2)3C- (CF 3 SO 2 ) 3 C -
화합물(168)compound (168) 식 (I-31)Formula (I-31) (CF3SO2)3C- (CF 3 SO 2 ) 3 C -
화합물(169)compound (169) 식 (I-38)Formula (I-38) (CF3SO2)3C- (CF 3 SO 2 ) 3 C -
화합물(170)compound (170) 식 (I-60)Formula (I-60) (CF3SO2)3C- (CF 3 SO 2 ) 3 C -
화합물(171)compound (171) 식 (I-61)Formula (I-61) (CF3SO2)3C- (CF 3 SO 2 ) 3 C -
화합물(172)compound (172) 식 (I-62)Formula (I-62) (CF3SO2)3C- (CF 3 SO 2 ) 3 C -
화합물(173)compound (173) 식 (I-79)Formula (I-79) (CF3SO2)3C- (CF 3 SO 2 ) 3 C -
화합물(174)compound (174) 식 (I-80)Formula (I-80) (CF3SO2)3C- (CF 3 SO 2 ) 3 C -
화합물(175)compound (175) 식 (I-85)Formula (I-85) (CF3SO2)3C- (CF 3 SO 2 ) 3 C -
화합물(176)compound (176) 식 (I-87)Formula (I-87) (CF3SO2)3C- (CF 3 SO 2 ) 3 C -
화합물(177)compound (177) 식 (I-90)Formula (I-90) (CF3SO2)3C- (CF 3 SO 2 ) 3 C -
화합물(178)compound (178) 식 (I-93)Formula (I-93) (CF3SO2)3C- (CF 3 SO 2 ) 3 C -
화합물(179)compound (179) 식 (I-94)Formula (I-94) (CF3SO2)3C- (CF 3 SO 2 ) 3 C -
화합물(180)compound (180) 식 (I-95)Formula (I-95) (CF3SO2)3C- (CF 3 SO 2 ) 3 C -
화합물(181)compound (181) 식 (I-96)Formula (I-96) (CF3SO2)3C- (CF 3 SO 2 ) 3 C -
화합물(182)compound (182) 식 (I-101)Formula (I-101) (CF3SO2)3C- (CF 3 SO 2 ) 3 C -
화합물(183)compound (183) 식 (I-103)Formula (I-103) (CF3SO2)3C- (CF 3 SO 2 ) 3 C -
화합물(184)Compound (184) 식 (I-105)Formula (I-105) (CF3SO2)3C- (CF 3 SO 2 ) 3 C -
화합물(185)compound (185) 식 (I-107)Formula (I-107) (CF3SO2)3C- (CF 3 SO 2 ) 3 C -
화합물(186)compound (186) 식 (I-128)Formula (I-128) (CF3SO2)3C- (CF 3 SO 2 ) 3 C -
화합물(187)compound (187) 식 (I-133)Formula (I-133) (CF3SO2)3C- (CF 3 SO 2 ) 3 C -
화합물(188)Compound (188) 식 (I-135)Formula (I-135) (CF3SO2)3C- (CF 3 SO 2 ) 3 C -
화합물(189)compound (189) 식 (I-137)Formula (I-137) (CF3SO2)3C- (CF 3 SO 2 ) 3 C -
화합물(190)compound (190) 식 (I-139)Formula (I-139) (CF3SO2)3C- (CF 3 SO 2 ) 3 C -
번호number 양이온cation 음이온anion
화합물(191)compound (191) 식 (I-1)Formula (I-1) (CN)4B- (CN) 4 B -
화합물(192)compound (192) 식 (I-2)Formula (I-2) (CN)4B- (CN) 4 B -
화합물(193)compound (193) 식 (I-3)Formula (I-3) (CN)4B- (CN) 4 B -
화합물(194)compound (194) 식 (I-4)Formula (I-4) (CN)4B- (CN) 4 B -
화합물(195)compound (195) 식 (I-8)Formula (I-8) (CN)4B- (CN) 4 B -
화합물(196)compound (196) 식 (I-12)Formula (I-12) (CN)4B- (CN) 4 B -
화합물(197)compound (197) 식 (I-13)Formula (I-13) (CN)4B- (CN) 4 B -
화합물(198)compound (198) 식 (I-17)Formula (I-17) (CN)4B- (CN) 4 B -
화합물(199)compound (199) 식 (I-18)Formula (I-18) (CN)4B- (CN) 4 B -
화합물(200)compound (200) 식 (I-23)Formula (I-23) (CN)4B- (CN) 4 B -
화합물(201)compound (201) 식 (I-25)Formula (I-25) (CN)4B- (CN) 4 B -
화합물(202)compound (202) 식 (I-26)Formula (I-26) (CN)4B- (CN) 4 B -
화합물(203)compound (203) 식 (I-27)Formula (I-27) (CN)4B- (CN) 4 B -
화합물(204)compound (204) 식 (I-28)Formula (I-28) (CN)4B- (CN) 4 B -
화합물(205)Compound (205) 식 (I-29)Formula (I-29) (CN)4B- (CN) 4 B -
화합물(206)compound (206) 식 (I-31)Formula (I-31) (CN)4B- (CN) 4 B -
화합물(207)Compound (207) 식 (I-38)Formula (I-38) (CN)4B- (CN) 4 B -
화합물(208)Compound (208) 식 (I-60)Formula (I-60) (CN)4B- (CN) 4 B -
화합물(209)compound (209) 식 (I-61)Formula (I-61) (CN)4B- (CN) 4 B -
화합물(210)compound (210) 식 (I-62)Formula (I-62) (CN)4B- (CN) 4 B -
화합물(211)Compound (211) 식 (I-79)Formula (I-79) (CN)4B- (CN) 4 B -
화합물(212)Compound (212) 식 (I-80)Formula (I-80) (CN)4B- (CN) 4 B -
화합물(213)Compound (213) 식 (I-85)Formula (I-85) (CN)4B- (CN) 4 B -
화합물(214)Compound (214) 식 (I-87)Formula (I-87) (CN)4B- (CN) 4 B -
화합물(215)Compound (215) 식 (I-90)Formula (I-90) (CN)4B- (CN) 4 B -
화합물(216)Compound (216) 식 (I-93)Formula (I-93) (CN)4B- (CN) 4 B -
화합물(217)Compound (217) 식 (I-94)Formula (I-94) (CN)4B- (CN) 4 B -
화합물(218)Compound (218) 식 (I-95)Formula (I-95) (CN)4B- (CN) 4 B -
화합물(219)Compound (219) 식 (I-96)Formula (I-96) (CN)4B- (CN) 4 B -
화합물(220)compound (220) 식 (I-101)Formula (I-101) (CN)4B- (CN) 4 B -
화합물(221)Compound (221) 식 (I-103)Formula (I-103) (CN)4B- (CN) 4 B -
화합물(222)compound (222) 식 (I-105)Formula (I-105) (CN)4B- (CN) 4 B -
화합물(223)Compound (223) 식 (I-107)Formula (I-107) (CN)4B- (CN) 4 B -
화합물(224)compound (224) 식 (I-128)Formula (I-128) (CN)4B- (CN) 4 B -
화합물(225)Compound (225) 식 (I-133)Formula (I-133) (CN)4B- (CN) 4 B -
화합물(226)compound (226) 식 (I-135)Formula (I-135) (CN)4B- (CN) 4 B -
화합물(227)compound (227) 식 (I-137)Formula (I-137) (CN)4B- (CN) 4 B -
화합물(228)Compound (228) 식 (I-139)Formula (I-139) (CN)4B- (CN) 4 B -
번호number 양이온cation 음이온anion
화합물(229)compound (229) 식 (I-1)Formula (I-1) (C6H5)4B- (C 6 H 5 ) 4 B -
화합물(230)compound (230) 식 (I-2)Formula (I-2) (C6H5)4B- (C 6 H 5 ) 4 B -
화합물(231)compound (231) 식 (I-3)Formula (I-3) (C6H5)4B- (C 6 H 5 ) 4 B -
화합물(232)compound (232) 식 (I-4)Formula (I-4) (C6H5)4B- (C 6 H 5 ) 4 B -
화합물(233)Compound (233) 식 (I-8)Formula (I-8) (C6H5)4B- (C 6 H 5 ) 4 B -
화합물(234)Compound (234) 식 (I-12)Formula (I-12) (C6H5)4B- (C 6 H 5 ) 4 B -
화합물(235)Compound (235) 식 (I-13)Formula (I-13) (C6H5)4B- (C 6 H 5 ) 4 B -
화합물(236)compound (236) 식 (I-17)Formula (I-17) (C6H5)4B- (C 6 H 5 ) 4 B -
화합물(237)compound (237) 식 (I-18)Formula (I-18) (C6H5)4B- (C 6 H 5 ) 4 B -
화합물(238)Compound (238) 식 (I-23)Formula (I-23) (C6H5)4B- (C 6 H 5 ) 4 B -
화합물(239)compound (239) 식 (I-25)Formula (I-25) (C6H5)4B- (C 6 H 5 ) 4 B -
화합물(240)compound (240) 식 (I-26)Formula (I-26) (C6H5)4B- (C 6 H 5 ) 4 B -
화합물(241)Compound (241) 식 (I-27)Formula (I-27) (C6H5)4B- (C 6 H 5 ) 4 B -
화합물(242)Compound (242) 식 (I-28)Formula (I-28) (C6H5)4B- (C 6 H 5 ) 4 B -
화합물(243)Compound (243) 식 (I-29)Formula (I-29) (C6H5)4B- (C 6 H 5 ) 4 B -
화합물(244)compound (244) 식 (I-31)Formula (I-31) (C6H5)4B- (C 6 H 5 ) 4 B -
화합물(245)Compound (245) 식 (I-38)Formula (I-38) (C6H5)4B- (C 6 H 5 ) 4 B -
화합물(246)compound (246) 식 (I-60)Formula (I-60) (C6H5)4B- (C 6 H 5 ) 4 B -
화합물(247)Compound (247) 식 (I-61)Formula (I-61) (C6H5)4B- (C 6 H 5 ) 4 B -
화합물(248)Compound (248) 식 (I-62)Formula (I-62) (C6H5)4B- (C 6 H 5 ) 4 B -
화합물(249)compound (249) 식 (I-79)Formula (I-79) (C6H5)4B- (C 6 H 5 ) 4 B -
화합물(250)compound (250) 식 (I-80)Formula (I-80) (C6H5)4B- (C 6 H 5 ) 4 B -
화합물(251)compound (251) 식 (I-85)Formula (I-85) (C6H5)4B- (C 6 H 5 ) 4 B -
화합물(252)compound (252) 식 (I-87)Formula (I-87) (C6H5)4B- (C 6 H 5 ) 4 B -
화합물(253)compound (253) 식 (I-90)Formula (I-90) (C6H5)4B- (C 6 H 5 ) 4 B -
화합물(254)compound (254) 식 (I-93)Formula (I-93) (C6H5)4B- (C 6 H 5 ) 4 B -
화합물(255)Compound (255) 식 (I-94)Formula (I-94) (C6H5)4B- (C 6 H 5 ) 4 B -
화합물(256)compound (256) 식 (I-95)Formula (I-95) (C6H5)4B- (C 6 H 5 ) 4 B -
화합물(257)compound (257) 식 (I-96)Formula (I-96) (C6H5)4B- (C 6 H 5 ) 4 B -
화합물(258)compound (258) 식 (I-101)Formula (I-101) (C6H5)4B- (C 6 H 5 ) 4 B -
화합물(259)compound (259) 식 (I-103)Formula (I-103) (C6H5)4B- (C 6 H 5 ) 4 B -
화합물(260)compound (260) 식 (I-105)Formula (I-105) (C6H5)4B- (C 6 H 5 ) 4 B -
화합물(261)Compound (261) 식 (I-107)Formula (I-107) (C6H5)4B- (C 6 H 5 ) 4 B -
화합물(262)compound (262) 식 (I-128)Formula (I-128) (C6H5)4B- (C 6 H 5 ) 4 B -
화합물(263)compound (263) 식 (I-133)Formula (I-133) (C6H5)4B- (C 6 H 5 ) 4 B -
화합물(264)compound (264) 식 (I-135)Formula (I-135) (C6H5)4B- (C 6 H 5 ) 4 B -
화합물(265)compound (265) 식 (I-137)Formula (I-137) (C6H5)4B- (C 6 H 5 ) 4 B -
화합물(266)compound (266) 식 (I-139)Formula (I-139) (C6H5)4B- (C 6 H 5 ) 4 B -
번호number 양이온cation 음이온anion
화합물(267)compound (267) 식 (I-1)Formula (I-1) (C6F5)4B- (C 6 F 5 ) 4 B -
화합물(268)compound (268) 식 (I-2)Formula (I-2) (C6F5)4B- (C 6 F 5 ) 4 B -
화합물(269)compound (269) 식 (I-3)Formula (I-3) (C6F5)4B- (C 6 F 5 ) 4 B -
화합물(270)compound (270) 식 (I-4)Formula (I-4) (C6F5)4B- (C 6 F 5 ) 4 B -
화합물(271)Compound (271) 식 (I-8)Formula (I-8) (C6F5)4B- (C 6 F 5 ) 4 B -
화합물(272)compound (272) 식 (I-12)Formula (I-12) (C6F5)4B- (C 6 F 5 ) 4 B -
화합물(273)compound (273) 식 (I-13)Formula (I-13) (C6F5)4B- (C 6 F 5 ) 4 B -
화합물(274)Compound (274) 식 (I-17)Formula (I-17) (C6F5)4B- (C 6 F 5 ) 4 B -
화합물(275)compound (275) 식 (I-18)Formula (I-18) (C6F5)4B- (C 6 F 5 ) 4 B -
화합물(276)compound (276) 식 (I-23)Formula (I-23) (C6F5)4B- (C 6 F 5 ) 4 B -
화합물(277)compound (277) 식 (I-25)Formula (I-25) (C6F5)4B- (C 6 F 5 ) 4 B -
화합물(278)Compound (278) 식 (I-26)Formula (I-26) (C6F5)4B- (C 6 F 5 ) 4 B -
화합물(279)compound (279) 식 (I-27)Formula (I-27) (C6F5)4B- (C 6 F 5 ) 4 B -
화합물(280)compound (280) 식 (I-28)Formula (I-28) (C6F5)4B- (C 6 F 5 ) 4 B -
화합물(281)compound (281) 식 (I-29)Formula (I-29) (C6F5)4B- (C 6 F 5 ) 4 B -
화합물(282)compound (282) 식 (I-31)Formula (I-31) (C6F5)4B- (C 6 F 5 ) 4 B -
화합물(283)Compound (283) 식 (I-38)Formula (I-38) (C6F5)4B- (C 6 F 5 ) 4 B -
화합물(284)Compound (284) 식 (I-60)Formula (I-60) (C6F5)4B- (C 6 F 5 ) 4 B -
화합물(285)Compound (285) 식 (I-61)Formula (I-61) (C6F5)4B- (C 6 F 5 ) 4 B -
화합물(286)compound (286) 식 (I-62)Formula (I-62) (C6F5)4B- (C 6 F 5 ) 4 B -
화합물(287)Compound (287) 식 (I-79)Formula (I-79) (C6F5)4B- (C 6 F 5 ) 4 B -
화합물(288)Compound (288) 식 (I-80)Formula (I-80) (C6F5)4B- (C 6 F 5 ) 4 B -
화합물(289)Compound (289) 식 (I-85)Formula (I-85) (C6F5)4B- (C 6 F 5 ) 4 B -
화합물(290)compound (290) 식 (I-87)Formula (I-87) (C6F5)4B- (C 6 F 5 ) 4 B -
화합물(291)compound (291) 식 (I-90)Formula (I-90) (C6F5)4B- (C 6 F 5 ) 4 B -
화합물(292)compound (292) 식 (I-93)Formula (I-93) (C6F5)4B- (C 6 F 5 ) 4 B -
화합물(293)compound (293) 식 (I-94)Formula (I-94) (C6F5)4B- (C 6 F 5 ) 4 B -
화합물(294)compound (294) 식 (I-95)Formula (I-95) (C6F5)4B- (C 6 F 5 ) 4 B -
화합물(295)compound (295) 식 (I-96)Formula (I-96) (C6F5)4B- (C 6 F 5 ) 4 B -
화합물(296)compound (296) 식 (I-101)Formula (I-101) (C6F5)4B- (C 6 F 5 ) 4 B -
화합물(297)compound (297) 식 (I-103)Formula (I-103) (C6F5)4B- (C 6 F 5 ) 4 B -
화합물(298)compound (298) 식 (I-105)Formula (I-105) (C6F5)4B- (C 6 F 5 ) 4 B -
화합물(299)compound (299) 식 (I-107)Formula (I-107) (C6F5)4B- (C 6 F 5 ) 4 B -
화합물(300)compound (300) 식 (I-128)Formula (I-128) (C6F5)4B- (C 6 F 5 ) 4 B -
화합물(301)compound (301) 식 (I-133)Formula (I-133) (C6F5)4B- (C 6 F 5 ) 4 B -
화합물(302)compound (302) 식 (I-135)Formula (I-135) (C6F5)4B- (C 6 F 5 ) 4 B -
화합물(303)Compound (303) 식 (I-137)Formula (I-137) (C6F5)4B- (C 6 F 5 ) 4 B -
화합물(304)Compound (304) 식 (I-139)Formula (I-139) (C6F5)4B- (C 6 F 5 ) 4 B -
화합물(I)로는 화합물(3), 화합물(39), 화합물(40), 화합물(41), 화합물(43), 화합물(45), 화합물(46), 화합물(47), 화합물(49), 화합물(53), 화합물(55), 화합물(56), 화합물(57), 화합물(58), 화합물(59), 화합물(60), 화합물(65), 화합물(66), 화합물(67), 화합물(70), 화합물(72), 화합물(75), 화합물(115), 화합물(116), 화합물(117), 화합물(119), 화합물(121), 화합물(122), 화합물(123), 화합물(125), 화합물(129), 화합물(131), 화합물(132), 화합물(133), 화합물(134), 화합물(135), 화합물(136), 화합물(141), 화합물(142), 화합물(143), 화합물(146), 화합물(148), 화합물(151), 화합물(153), 화합물(154), 화합물(155), 화합물(157), 화합물(159), 화합물(160), 화합물(161), 화합물(163), 화합물(167), 화합물(169), 화합물(170), 화합물(171), 화합물(172), 화합물(173), 화합물(174), 화합물(179), 화합물(180), 화합물(181), 화합물(184), 화합물(186), 화합물(189), 화합물(191), 화합물(192), 화합물(193), 화합물(195), 화합물(197), 화합물(198), 화합물(199), 화합물(201), 화합물(205), 화합물(207), 화합물(208), 화합물(209), 화합물(210), 화합물(211), 화합물(212), 화합물(217), 화합물(218), 화합물(219), 화합물(222), 화합물(224), 화합물(227), 화합물(267), 화합물(268), 화합물(269), 화합물(271), 화합물(273), 화합물(274), 화합물(275), 화합물(277), 화합물(281), 화합물(283), 화합물(284), 화합물(285), 화합물(286), 화합물(287), 화합물(288), 화합물(293), 화합물(294), 화합물(295), 화합물(298), 화합물(300)인 것이 바람직하다.Compound (I) includes compound (3), compound (39), compound (40), compound (41), compound (43), compound (45), compound (46), compound (47), compound (49), Compound (53), Compound (55), Compound (56), Compound (57), Compound (58), Compound (59), Compound (60), Compound (65), Compound (66), Compound (67), Compound (70), Compound (72), Compound (75), Compound (115), Compound (116), Compound (117), Compound (119), Compound (121), Compound (122), Compound (123), Compound (125), Compound (129), Compound (131), Compound (132), Compound (133), Compound (134), Compound (135), Compound (136), Compound (141), Compound (142), Compound (143), Compound (146), Compound (148), Compound (151), Compound (153), Compound (154), Compound (155), Compound (157), Compound (159), Compound (160), Compound (161), Compound (163), Compound (167), Compound (169), Compound (170), Compound (171), Compound (172), Compound (173), Compound (174), Compound (179), Compound (180), Compound (181), Compound (184), Compound (186), Compound (189), Compound (191), Compound (192), Compound (193), Compound (195), Compound (197), Compound (198), Compound (199), Compound (201), Compound (205), Compound (207), Compound (208), Compound (209), Compound (210), Compound (211), Compound (212), Compound (217), Compound (218), Compound (219), Compound (222), Compound (224), Compound (227), Compound (267), Compound (268), Compound (269), Compound (271), Compound (273), Compound (274), Compound (275), Compound (277), Compound (281), Compound (283), Compound (284), Compound (285), Compound (286), Compound (287), Compound (288), Compound (293), Compound ( 294), compound (295), compound (298), and compound (300) are preferred.
<화합물(I)의 제조 방법><Method for producing compound (I)>
화합물(I)이 갖는 식 (I)로 표시되는 부분 구조를 포함하는 양이온은 식 (M)으로 표시되는 화합물(이하 화합물(M)이라 하는 경우가 있다.)과 식 (b-1)로 표시되는 화합물(이하 화합물(b-1)이라 하는 경우가 있다.)과 식 (b-2)로 표시되는 화합물(이하 화합물(b-2)이라 하는 경우가 있다.)을 반응시킴으로써 제조할 수 있다.The cation containing the partial structure represented by formula (I) of compound (I) is represented by the compound represented by formula (M) (hereinafter sometimes referred to as compound (M)) and formula (b-1) It can be produced by reacting a compound (hereinafter sometimes referred to as compound (b-1)) with a compound represented by formula (b-2) (hereinafter sometimes referred to as compound (b-2)). .
[화학식 27][Formula 27]
Figure PCTKR2022010249-appb-I000027
Figure PCTKR2022010249-appb-I000027
[식 중, 고리 W1, 고리 W2, R1, R2, R3, R4, R5 및 R6은 각각 상기와 동일한 의미를 나타낸다.][In the formula, ring W 1 , ring W 2 , R 1 , R 2 , R 3 , R 4 , R 5 and R 6 respectively represent the same meanings as above.]
화합물(M)과 화합물(b-1)과 화합물(b-2)의 반응은 촉매의 존재 하에 수행되는 것이 바람직하다.The reaction of compound (M) with compound (b-1) and compound (b-2) is preferably carried out in the presence of a catalyst.
촉매로는 포름산, 아세트산, 트리플루오로아세트산 등의 카복실산; 염화암모늄; 4염화티탄, 염화알루미늄, 알루미늄이소프로폭시드, 3브롬화붕소, 3불화붕소, 염화철, 염화갈륨, 4염화주석, 란타노이드트리플레이트 등의 루이스산; 메탄설폰산 무수물, 파라톨루엔설폰산 무수물, 트리플루오로메탄설폰산 무수물, 노나플루오로부탄설폰산 무수물 등의 설폰산 무수물; 파라톨루엔설폰산, 트리플루오로메탄설폰산, 플루오로황산 등의 설폰산; 디메틸황산, 메틸트리플레이트, 요오드메탄, 트리메틸옥소늄테트라플루오로보레이트, 플루오로황산 디메틸 등의 친전자적 알킬화제; 파라톨루엔설포닐클로라이드, 트리플루오로메탄설포닐클로라이드 등의 설폰산 할로겐화물 등을 들 수 있다.Examples of the catalyst include carboxylic acids such as formic acid, acetic acid, and trifluoroacetic acid; ammonium chloride; Lewis acids such as titanium tetrachloride, aluminum chloride, aluminum isopropoxide, boron tribromide, boron trifluoride, iron chloride, gallium chloride, tin tetrachloride, and lanthanoid triflate; sulfonic acid anhydrides such as methanesulfonic acid anhydride, p-toluenesulfonic acid anhydride, trifluoromethanesulfonic acid anhydride, and nonafluorobutanesulfonic acid anhydride; sulfonic acids such as p-toluenesulfonic acid, trifluoromethanesulfonic acid, and fluorosulfuric acid; electrophilic alkylating agents such as dimethyl sulfuric acid, methyl triflate, iodomethane, trimethyloxonium tetrafluoroborate, and dimethyl fluorosulfate; and sulfonic acid halides such as p-toluenesulfonyl chloride and trifluoromethanesulfonyl chloride.
촉매의 사용량은 화합물(M) 1 몰에 대해 통상적으로 0.001 내지 10 몰이며, 0.05 내지 2 몰인 것이 바람직하다.The amount of the catalyst used is usually 0.001 to 10 moles, preferably 0.05 to 2 moles, per mole of the compound (M).
화합물(M)과 화합물(b-1)과 화합물(b-2)의 반응은 염기의 존재 하에 수행되는 것이 바람직하다.The reaction of compound (M) with compound (b-1) and compound (b-2) is preferably carried out in the presence of a base.
염기로는 나트륨메톡시드, 칼륨메톡시드, 리튬메톡시드, 나트륨에톡시드, 칼륨에톡시드, 리튬에톡시드, 나트륨이소프로폭시드, 나트륨터셔리부톡시드, 칼륨터셔리부톡시드 등의 금속 알콕시드 (바람직하게 알칼리 금속 알콕시드) 등; 수산화리튬, 수산화나트륨, 수산화칼륨 등의 금속 수산화물, 수소화나트륨, 수소화칼륨, 수소화알루미늄리튬, 수소화붕소나트륨 등의 금속 수소화물; 탄산나트륨, 탄산수소나트륨, 탄산칼륨, 탄산수소칼륨, 탄산리튬, 탄산수소리튬, 탄산세슘 등의 금속 탄산염; 메틸리튬, n-부틸리튬, sec-부틸리튬, tert-부틸리튬, 페닐리튬 등의 유기 리튬 화합물; 메틸마그네슘브로미드, 이소프로필마그네슘브로미드, n-부틸마그네슘브로미드, 이소프로필마그네슘클로라이드 등의 알킬 금속 할로겐화물; 리튬디이소프로필아미드, 리튬 2,2,6,6-테트라메틸피페리디드, 리튬(비스트리메틸실릴)아미드, 리튬테트라메틸피페리디드 등의 금속 아미드 화합물; 피리딘, 2,6-디메틸피리딘, 2,6-디-tert-부틸피리딘, 트리에틸아민, 디이소프로필에틸아민, 트리이소프로필아민, 2,2,6,6-테트라메틸피페리딘, 피페리딘, 피롤리딘, 프롤린, 아닐린, N,N-디메틸아닐린, 에틸렌디아민 등의 아민 화합물; 아세트산나트륨, 아세트산칼륨, 포름산나트륨 등의 금속 카복실산염; 아세트산암모늄 등의 카복실산암모늄염; 등을 들 수 있다.Bases include metals such as sodium methoxide, potassium methoxide, lithium methoxide, sodium ethoxide, potassium ethoxide, lithium ethoxide, sodium isopropoxide, sodium tert-butoxide, and potassium tert-butoxide. alkoxides (preferably alkali metal alkoxides) and the like; metal hydroxides such as lithium hydroxide, sodium hydroxide and potassium hydroxide; metal hydrides such as sodium hydride, potassium hydride, lithium aluminum hydride and sodium borohydride; Metal carbonates, such as sodium carbonate, sodium hydrogencarbonate, potassium carbonate, potassium hydrogencarbonate, lithium carbonate, lithium hydrogencarbonate, and cesium carbonate; organolithium compounds such as methyllithium, n-butyllithium, sec-butyllithium, tert-butyllithium, and phenyllithium; Alkyl metal halides, such as methyl magnesium bromide, isopropyl magnesium bromide, n-butyl magnesium bromide, and isopropyl magnesium chloride; metal amide compounds such as lithium diisopropylamide, lithium 2,2,6,6-tetramethylpiperidide, lithium (bistrimethylsilyl)amide, and lithium tetramethylpiperidide; Pyridine, 2,6-dimethylpyridine, 2,6-di-tert-butylpyridine, triethylamine, diisopropylethylamine, triisopropylamine, 2,2,6,6-tetramethylpiperidine, p amine compounds such as peridine, pyrrolidine, proline, aniline, N,N-dimethylaniline, and ethylenediamine; Metal carboxylates, such as sodium acetate, potassium acetate, and sodium formate; Carboxylate ammonium salts, such as ammonium acetate; etc. can be mentioned.
염기의 사용량으로는 화합물(M) 1 몰에 대해 통상적으로 0.1 내지 10 몰이며, 0.5 내지 2 몰인 것이 바람직하다.The amount of base used is usually 0.1 to 10 moles, preferably 0.5 to 2 moles, per mole of the compound (M).
화합물(M)과 화합물(b-1)과 화합물(b-2)의 반응은 용매의 존재 하에 수행할 수 있다.The reaction of compound (M), compound (b-1) and compound (b-2) can be carried out in the presence of a solvent.
용매로는 아세토니트릴, 벤조니트릴 등의 니트릴 용매; 벤젠, 톨루엔, 크실렌, 아니솔의 방향족 탄화수소 용매; n-헥산, n-헵탄, 시클로헥산, 메틸시클로헥산 등의 지방족 탄화수소 용매; 클로로벤젠, 오르토디클로로벤젠, 메타디클로로벤젠, 파라디클로로벤젠, 디클로로메탄, 디클로로에탄, 테트라클로로에탄, 테트라클로로에틸렌, 클로로포름 등의 할로겐계 용매; 아세트산메틸, 아세트산에틸, 아세트산부틸, 아세트산이소부틸, 아세트산노르말프로필 등의 에스테르 용매; 메탄올, 에탄올, 이소프로판올, 헥사플루오로이소프로판올, n-부탄올, 이소부탄올, tert-부탄올 등의 알코올 용매; 아세톤, 메틸에틸케톤, 메틸이소부틸케톤, 디이소부틸케톤, 시클로헥사논 등의 케톤계 용매; 테트라히드로퓨란, 2-메틸테트라히드로퓨란, 시클로펜틸메틸에테르, 4-메틸테트라히드로피란, 디옥산, 디에틸에테르, tert-부틸메틸에테르, 디이소프로필에테르, 디메톡시에탄, 디에톡시메탄 등의 에테르 용매; N,N-디메틸아세트아미드, N,N-디메틸포름아미드 등의 아미드 용매; 디메틸설폭시드; 1,3-디메틸-2-이미다졸리디논; 헥사메틸인산트리아미드; 물 등 을 들 수 있다. 용매는 니트릴 용매, 케톤 용매, 방향족 탄화수소 용매인 것이 바람직하고, 아세토니트릴, 톨루엔, 메틸에틸케톤, 메틸이소부틸케톤인 것이 보다 바람직하다.Examples of the solvent include nitrile solvents such as acetonitrile and benzonitrile; aromatic hydrocarbon solvents such as benzene, toluene, xylene, and anisole; aliphatic hydrocarbon solvents such as n-hexane, n-heptane, cyclohexane, and methylcyclohexane; halogen solvents such as chlorobenzene, orthodichlorobenzene, metadichlorobenzene, paradichlorobenzene, dichloromethane, dichloroethane, tetrachloroethane, tetrachloroethylene, and chloroform; ester solvents such as methyl acetate, ethyl acetate, butyl acetate, isobutyl acetate, and normal propyl acetate; alcohol solvents such as methanol, ethanol, isopropanol, hexafluoroisopropanol, n-butanol, isobutanol, and tert-butanol; ketone solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, and cyclohexanone; tetrahydrofuran, 2-methyltetrahydrofuran, cyclopentylmethyl ether, 4-methyltetrahydropyran, dioxane, diethyl ether, tert-butyl methyl ether, diisopropyl ether, dimethoxyethane, diethoxymethane, etc. ether solvent; amide solvents such as N,N-dimethylacetamide and N,N-dimethylformamide; dimethyl sulfoxide; 1,3-dimethyl-2-imidazolidinone; Hexamethylphosphate triamide; water and the like. The solvent is preferably a nitrile solvent, a ketone solvent, or an aromatic hydrocarbon solvent, and more preferably acetonitrile, toluene, methyl ethyl ketone, or methyl isobutyl ketone.
용매의 사용량으로는 화합물(M) 1 질량부에 대해 통상적으로 0.5 내지 1000 질량부이며, 1 내지 10 질량부인 것이 바람직하다.The amount of the solvent used is usually 0.5 to 1000 parts by mass, preferably 1 to 10 parts by mass, per 1 part by mass of the compound (M).
화합물(M)과 화합물(b-1)과 화합물(b-2)의 반응은 화합물(M)과 화합물(b-1)과 화합물(b-2)을 혼합함으로써 실시된다.The reaction of compound (M), compound (b-1) and compound (b-2) is carried out by mixing compound (M), compound (b-1) and compound (b-2).
화합물(M)과 화합물(b-1)과 화합물(b-2)의 반응은 화합물(M), 염기 및 촉매의 혼합물에 화합물(b-1)과 화합물(b-2)을 가하는 것이 바람직하다.For the reaction between compound (M), compound (b-1) and compound (b-2), it is preferable to add compound (b-1) and compound (b-2) to a mixture of compound (M), base and catalyst. .
화합물(b-1)의 사용량은 화합물(M) 1 몰에 대해 통상적으로 0.1 내지 20 몰이며, 0.5 내지 4 몰 당량인 것이 바람직하다.The amount of compound (b-1) used is usually 0.1 to 20 moles, preferably 0.5 to 4 mole equivalents, per mole of compound (M).
화합물(b-2)의 사용량은 화합물(M) 1 몰에 대해 통상적으로 0.1 내지 20 몰이며, 0.5 내지 4 몰 당량인 것이 바람직하다.The amount of compound (b-2) used is usually 0.1 to 20 moles, preferably 0.5 to 4 mole equivalents, per mole of compound (M).
화합물(M)과 화합물(b-1)과 화합물(b-2)의 반응 시간은 통상적으로 0.1 내지 100 시간이다.The reaction time of compound (M), compound (b-1) and compound (b-2) is usually 0.1 to 100 hours.
화합물(M)과 화합물(b-1)과 화합물(b-2)의 반응 온도는 통상적으로 -80 내지 200 ℃이다.The reaction temperature of compound (M), compound (b-1) and compound (b-2) is usually -80 to 200캜.
화합물(b-1) 및 화합물(b-2)로는 예컨대 아지리딘, 아제티딘, 피롤리딘, 피페리딘, 모폴린, 티오모폴린, 인돌린, 메틸인돌린, 니트로인돌린, 아미노비페닐, 시아노아미노비페닐, 니트로아미노비페닐, 메톡시아미노비페닐 등을 들 수 있다.Examples of the compound (b-1) and the compound (b-2) include aziridine, azetidine, pyrrolidine, piperidine, morpholine, thiomorpholine, indoline, methylindoline, nitroindoline, and aminobiphenyl. , cyanoaminobiphenyl, nitroaminobiphenyl, methoxyaminobiphenyl, etc. are mentioned.
화합물(M)로는 하기에 기재된 화합물을 들 수 있다.Examples of the compound (M) include compounds described below.
[화학식 28][Formula 28]
Figure PCTKR2022010249-appb-I000028
Figure PCTKR2022010249-appb-I000028
화합물(M)은 식 (M1-1)로 표시되는 화합물(이하 화합물(M1-1)이라 하는 경우가 있다.), 식 (M1-2)로 표시되는 화합물(이하 화합물(M1-2)이라 하는 경우가 있다.) 및 식 (M1-3)으로 표시되는 화합물(이하 화합물(M1-3)이라 하는 경우가 있다.)을 반응시킴으로써 제조할 수 있다.Compound (M) is a compound represented by formula (M1-1) (hereinafter sometimes referred to as compound (M1-1)) or a compound represented by formula (M1-2) (hereinafter referred to as compound (M1-2) ) and a compound represented by formula (M1-3) (hereinafter sometimes referred to as compound (M1-3)).
[화학식 29][Formula 29]
Figure PCTKR2022010249-appb-I000029
Figure PCTKR2022010249-appb-I000029
[식 중, 고리 W1, 고리 W2, R1 및 R2는 상기와 동일한 의미를 나타낸다.[In the formula, ring W 1 , ring W 2 , R 1 and R 2 represent the same meanings as above.
　 E1 및 E2는 각각 독립적으로 탈리기를 나타낸다.]E 1 and E 2 each independently represent a leaving group.]
E1 및 E2로 나타나는 탈리기로는 각각 독립적으로 할로겐 원자, 숙신이미드기, 말레이미드기, 사카린, 메틸설포닐기, p-메톡시벤젠설포닐기, p-톨루엔설포닐기, 트리플루오로메틸설포닐기, 노나플루오로부탄설포닐기 등을 들 수 있다.The leaving groups represented by E 1 and E 2 are each independently a halogen atom, a succinimide group, a maleimide group, saccharin, a methylsulfonyl group, a p-methoxybenzenesulfonyl group, a p-toluenesulfonyl group, and a trifluoromethylsulfonyl group. A yl group, a nonafluorobutanesulfonyl group, etc. are mentioned.
화합물(M1-1), 화합물(M1-2) 및 화합물(M1-3)의 반응은 염기의 존재 하에 수행하는 것이 바람직하다.The reaction of compound (M1-1), compound (M1-2) and compound (M1-3) is preferably carried out in the presence of a base.
염기로는 화합물(M)과 화합물(b-1)과 화합물(b-2)의 반응에 사용할 때의 염기와 동일한 것을 들 수 있고, 금속 알콕시드, 금속 수산화물, 금속 수소화물, 금속 탄산염, 유기 리튬, 금속 아미드 화합물, 아민 화합물 또는 금속 카복실산염인 것이 바람직하고, 칼륨에톡시드, 나트륨터셔리부톡시드, 칼륨터셔리부톡시드, 수산화나트륨, 수산화칼륨, 수소화나트륨, 수소화알루미늄리튬, 탄산나트륨, 탄산수소나트륨, 탄산칼륨, 탄산수소칼륨, 메틸리튬, 노르말부틸리튬, 터셔리부틸리튬, 리튬디이소프로필아미드, 리튬 2,2,6,6-테트라메틸피페리디드, 리튬(비스트리메틸실릴)아미드, 리튬테트라메틸피페리디드, 피리딘, 2,6-디메틸피리딘, 2,6-디터셔리부틸피리딘, 트리에틸아민, 디이소프로필에틸아민, 트리이소프로필아민, 2,2,6,6-테트라메틸피페리딘, 피페리딘, 피롤리딘, 프롤린, 아닐린, N,N-디메틸아닐린, 아세트산나트륨, 포름산나트륨, 아세트산암모늄인 것이 보다 바람직하다.Examples of the base include the same bases used for the reaction between compound (M), compound (b-1) and compound (b-2), metal alkoxides, metal hydroxides, metal hydrides, metal carbonates, organic It is preferably lithium, a metal amide compound, an amine compound or a metal carboxylate, potassium ethoxide, sodium tertiary butoxide, potassium tertiary butoxide, sodium hydroxide, potassium hydroxide, sodium hydride, lithium aluminum hydride, sodium carbonate, carbonate Sodium hydrogen carbonate, potassium carbonate, potassium hydrogen carbonate, methyl lithium, normal butyl lithium, tertiary butyl lithium, lithium diisopropylamide, lithium 2,2,6,6-tetramethylpiperidide, lithium (bistrimethylsilyl)amide , lithium tetramethylpiperidide, pyridine, 2,6-dimethylpyridine, 2,6-ditertiarybutylpyridine, triethylamine, diisopropylethylamine, triisopropylamine, 2,2,6,6-tetra Methylpiperidine, piperidine, pyrrolidine, proline, aniline, N,N-dimethylaniline, sodium acetate, sodium formate, and ammonium acetate are more preferable.
염기의 사용량으로는 화합물(M1-1) 1 몰에 대해 통상적으로 0.001 내지 20 몰이며, 0.1 내지 10 몰인 것이 바람직하다.The amount of the base used is usually 0.001 to 20 moles, preferably 0.1 to 10 moles, per mole of the compound (M1-1).
화합물(M1-1), 화합물(M1-2) 및 화합물(M1-3)의 반응은 용매의 존재 하에 수행할 수 있다. 용매로는 화합물(M)과 화합물(b-1)과 화합물(b-2)의 반응 시에 사용할 수 있는 용매와 동일한 것을 들 수 있다. 바람직하게 아세토니트릴, 메탄올, 에탄올, 톨루엔, 2-부탄온, 디옥산, 테트라히드로퓨란, 디메틸설폭시드, 디메틸포름아미드, 디메틸아세트아미드이다.The reaction of compound (M1-1), compound (M1-2) and compound (M1-3) can be carried out in the presence of a solvent. Examples of the solvent include the same solvents usable in the reaction of compound (M), compound (b-1) and compound (b-2). Preferred are acetonitrile, methanol, ethanol, toluene, 2-butanone, dioxane, tetrahydrofuran, dimethylsulfoxide, dimethylformamide and dimethylacetamide.
또한 용매는 탈수 용매인 것이 바람직하다.Also, the solvent is preferably a dehydration solvent.
화합물(M1-1), 화합물(M1-2) 및 화합물(M1-3)의 반응은 화합물(M1-1), 화합물(M1-2) 및 화합물(M1-3)을 혼합함으로써 실시되고, 염기, 화합물(M1-1), 화합물(M1-2) 및 화합물(M1-3)을 혼합함으로써 실시되는 것이 바람직하다.The reaction of compound (M1-1), compound (M1-2) and compound (M1-3) is carried out by mixing compound (M1-1), compound (M1-2) and compound (M1-3), and a base , It is preferably carried out by mixing the compound (M1-1), the compound (M1-2) and the compound (M1-3).
화합물(M1-1), 화합물(M1-2) 및 화합물(M1-3)의 반응은 탈산소 분위기 하(예컨대 질소 분위기 하)에 실시되는 것이 바람직하다.The reaction of the compound (M1-1), the compound (M1-2) and the compound (M1-3) is preferably carried out in a deoxygenated atmosphere (for example, a nitrogen atmosphere).
화합물(M1-2)의 사용량은 화합물(M1-1) 1 몰에 대해 통상적으로 0.1 내지 20 몰이며, 0.5 내지 10 몰인 것이 바람직하다.The amount of compound (M1-2) used is usually 0.1 to 20 moles, preferably 0.5 to 10 moles, per mole of compound (M1-1).
화합물(M1-3)의 사용량은 화합물(M1-1) 1 몰에 대해 통상적으로 0.1 내지 20 몰이며, 0.5 내지 10 몰인 것이 바람직하다.The amount of compound (M1-3) used is usually 0.1 to 20 moles, preferably 0.5 to 10 moles, per mole of compound (M1-1).
염기의 사용량은 화합물(M1-1) 1 몰에 대해 통상적으로 0.001 내지 20 몰이며, 0.1 내지 10 몰인 것이 바람직하다.The amount of the base used is usually 0.001 to 20 mol, preferably 0.1 to 10 mol, per 1 mol of the compound (M1-1).
화합물(M1-1), 화합물(M1-2) 및 화합물(M1-3)의 반응 시간은 통상적으로 0.1 내지 200 시간이다.The reaction time of compound (M1-1), compound (M1-2) and compound (M1-3) is usually 0.1 to 200 hours.
화합물(M1-1), 화합물(M1-2) 및 화합물(M1-3)의 반응 온도는 통상적으로 -100 내지 200 ℃이다.The reaction temperature of compound (M1-1), compound (M1-2) and compound (M1-3) is usually -100 to 200캜.
화합물(M1-1)로는 시판품을 사용할 수도 있고, 7-히드록시-2,3,4,4a,5,6-헥사히드로나프탈렌-2-온 등을 들 수 있다.As compound (M1-1), a commercial item can also be used, and 7-hydroxy-2,3,4,4a,5,6-hexahydronaphthalen-2-one etc. are mentioned.
화합물(M1-2) 및 화합물(M1-3)로는 시판품을 사용할 수도 있다. 예컨대 클로로시안, 브로모시안, 파라톨루엔설포닐시아나이드, 트리플루오로메탄설포닐시아나이드, 티오시안산벤질, tert-부틸이소시아나이드, 시안화구리 (I), 시안화칼륨, 1-시아노-4-(디메틸아미노)피리디늄테트라플루오로보레이트, p-톨루엔설포닐메틸이소시아나이드, 1-클로로메틸-4-플루오로-1,4-디아조니아비시클로[2.2.2]옥탄 비스(테트라플루오로보레이트)(셀렉트 플루오르(Air Products and Chemicals의 등록 상표)라고도 함), 벤조일(페닐요오도니오)(트리플루오로메탄설포닐)메타니드, 2,8-디플루오로-5-(트리플루오로메틸)-5H-디벤조[b,d]티오펜-5-이움트리플루오로메탄설포네이트, 1-플루오로-3,3-디메틸-1,2-벤조요오독솔, N-브로모숙신이미드, N-클로로숙신이미드, N-요오드숙신이미드, 테트라메틸암모늄트리브로미드, 불소 (F2), 브롬(Br2), 염소(Cl2), 요오드(I2), N-브로모프탈이미드, N-클로로프탈이미드, N-요오드프탈이미드, N-브로모사카린, N- (트리플루오로메틸티오)사카린, N-(트리플루오로메틸티오)사카린, N-(트리플루오로메틸티오)아닐린, N-메틸-N-[(트리플루오로메틸)티오]-파라톨루엔설폰아미드, 1-트리플루오로메틸-3,3-디메틸-1,2-벤조요오독솔, 1-트리플루오로메틸-1,2-벤조요오독솔-3(1H)-온, 질산, 요오드메탄, 디메틸황산, 메틸트리플레이트, 에틸트리플레이트, 노르말부틸트리플레이트, 아세틸클로라이드 등을 들 수 있다.A commercial item can also be used as compound (M1-2) and compound (M1-3). For example, chlorocyanate, bromocyanide, p-toluenesulfonylcyanide, trifluoromethanesulfonylcyanide, benzyl thiocyanate, tert-butylisocyanide, copper (I) cyanide, potassium cyanide, 1-cyano- 4-(dimethylamino)pyridinium tetrafluoroborate, p-toluenesulfonylmethylisocyanide, 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetra Fluoroborate) (also known as Select Fluor (registered trademark of Air Products and Chemicals)), benzoyl (phenyliodonio) (trifluoromethanesulfonyl)methanide, 2,8-difluoro-5-(tri Fluoromethyl)-5H-dibenzo[b,d]thiophene-5-iumtrifluoromethanesulfonate, 1-fluoro-3,3-dimethyl-1,2-benzoiodoxole, N-bromo Succinimide, N-chlorosuccinimide, N-iodosuccinimide, tetramethylammonium tribromide, fluorine (F 2 ), bromine (Br 2 ), chlorine (Cl 2 ), iodine (I 2 ), N -Bromophthalimide, N-chlorophthalimide, N-iodophthalimide, N-bromosaccharin, N-(trifluoromethylthio)saccharin, N-(trifluoromethylthio)saccharin, N-(trifluoromethylthio)aniline, N-methyl-N-[(trifluoromethyl)thio]-paratoluenesulfonamide, 1-trifluoromethyl-3,3-dimethyl-1,2-benzo Iodoxol, 1-trifluoromethyl-1,2-benzoiodoxol-3(1H)-one, nitric acid, iodomethane, dimethyl sulfate, methyl triflate, ethyl triflate, normal butyl triflate, acetyl chloride, etc. can be heard
화합물(M)과 화합물(b-1)과 화합물(b-2)을 염기의 존재 하에 반응시키면, 염기 유래의 음이온과 식 (I-A)로 표시되는 양이온을 포함하는 화합물(I)을 얻을 수 있다.When compound (M), compound (b-1), and compound (b-2) are reacted in the presence of a base, compound (I) containing an anion derived from a base and a cation represented by formula (I-A) can be obtained. .
화합물(I)의 음이온을 원하는 음이온으로 교환하고자 할 경우에는 화합물(I)과 원하는 음이온을 갖는 염을 혼합함으로써 이온 교환을 수행하면 된다. 상기 이온 교환은 용매의 존재 하에 수행할 수 있다. 원하는 음이온을 갖는 염은 예컨대 리튬염, 나트륨염, 칼륨염, 세슘염, 바륨염, 칼슘염, 마그네슘염, 암모늄염 등을 들 수 있다.In the case of exchanging the anion of Compound (I) with a desired anion, ion exchange may be performed by mixing Compound (I) with a salt having a desired anion. The ion exchange may be performed in the presence of a solvent. Examples of salts having desired anions include lithium salts, sodium salts, potassium salts, cesium salts, barium salts, calcium salts, magnesium salts, and ammonium salts.
<화합물(I)을 포함하는 조성물><Composition Containing Compound (I)>
본 발명은 화합물(I)을 함유하는 조성물도 포함한다.The present invention also includes compositions containing Compound (I).
화합물(I)을 포함하는 조성물은 모든 용도에 사용 가능하지만, 그 중에서도 햇빛 또는 자외선을 포함하는 빛에 노출될 가능성이 있는 용도에 특히 적합하게 사용될 수 있다. 구체적인 예로는 예컨대 유리 대체품과 그 표면 코팅재; 주거, 시설, 수송 기기 등의 창유리, 채광 유리 및 광원 보호 유리용 코팅재; 주거, 시설, 수송 기기 등의 윈도우 필름; 주거, 시설, 수송 기기 등의 내외장재 및 내외장용 도료 및 그 도료에 의해 형성되는 도막; 알키드 수지 래커 도료 및 그 도료에 의해 형성되는 도막; 아크릴 래커 도료 및 그 도료에 의해 형성되는 도막; 형광등, 수은등 등의 자외선을 발하는 광원용 부재; 정밀 기계, 전자전기 기기용 부재, 각종 디스플레이에서 발생하는 전자파 등의 차단용 재료; 식품, 화학품, 약품 등의 용기 또는 포장재; 보틀, 박스, 블리스터, 컵, 특수 포장용, 컴팩트 디스크 코트, 농공업용 시트 또는 필름재; 인쇄물, 염색물, 염·안료 등의 퇴색 방지제; 폴리머 지지체용(예컨대 기계 및 자동차 부품과 같은 플라스틱제 부품용) 보호막; 인쇄물 오버코트; 잉크젯 매체 피막; 적층 매트; 옵티컬 라이트 필름; 안전 유리 및 프론트 유리의 중간층; 일렉트로크로믹 또는 포토크로믹 용도; 오버라미네이트 필름; 태양열 제어막; 자외선 차단 크림, 샴푸, 린스, 정발료 등의 화장품; 스포츠웨어, 스타킹, 모자 등의 의류용 섬유 제품 및 섬유; 커튼, 융단, 벽지 등의 가정용 내장품; 플라스틱 렌즈, 콘택트 렌즈, 의안 등의 의료용 기구; 광학 필터, 백라이트 디스플레이 필름, 프리즘, 거울, 사진 재료 등의 광학 용품; 금형막, 전사식 스티커, 낙서 방지막, 테이프, 잉크 등의 문방구; 표시판, 표시기 등과 그 표면 코팅재 등을 들 수 있다.The composition containing compound (I) can be used for all applications, but can be particularly suitably used for applications that may be exposed to light including sunlight or ultraviolet rays. Specific examples include, for example, glass substitutes and surface coatings thereof; Coating materials for window glass, skylight glass, and light source protection glass of dwellings, facilities, transportation equipment, etc.; window films for dwellings, facilities, transportation devices, etc.; paints for interior and exterior materials and interior and exterior decorations of dwellings, facilities, transportation equipment, etc., and coating films formed by the paints; alkyd resin lacquer paints and coating films formed by the paints; acrylic lacquer paint and a coating film formed by the paint; members for light sources emitting ultraviolet rays such as fluorescent lamps and mercury lamps; Materials for blocking electromagnetic waves generated from precision instruments, members for electronic and electrical devices, and various displays; Containers or packaging materials for food, chemicals, medicines, etc.; Bottles, boxes, blisters, cups, special packaging, compact disc coats, sheet or film materials for agriculture and industry; fading inhibitors such as prints, dyes, dyes and pigments; protective films for polymer supports (for example, for parts made of plastics such as machine and automobile parts); printed overcoat; inkjet media coatings; laminated mat; optical light film; interlayer of safety glass and windshield; electrochromic or photochromic applications; overlaminate film; solar control membrane; cosmetics such as sunscreen creams, shampoos, conditioners, and hair conditioners; textile products and textiles for apparel such as sportswear, stockings and caps; home furnishings such as curtains, rugs, and wallpaper; medical instruments such as plastic lenses, contact lenses, and artificial eyes; optical products such as optical filters, backlight display films, prisms, mirrors, and photographic materials; stationery such as mold film, transfer sticker, anti-graffiti film, tape, ink; display panels, indicators, and the like, and surface coating materials thereof.
화합물(I)을 포함하는 조성물은 화합물(I)과 수지를 포함하는 수지 조성물(이하 "수지 조성물"이라 하는 경우가 있다.) 또는 화합물(I)과 중합성 모노머를 포함하는 조성물(이하 "조성물(1)"이라 하는 경우가 있다.)인 것이 바람직하다.A composition containing Compound (I) may be a resin composition containing Compound (I) and a resin (hereinafter sometimes referred to as "resin composition") or a composition containing Compound (I) and a polymerizable monomer (hereinafter referred to as "composition"). (1) It is sometimes referred to as ".) is preferable.
수지 조성물에 사용되는 수지로는 공지된 각종 성형체, 시트, 필름 등의 제조에 종래부터 사용되고 있는 열가소성 수지 및 열경화성 수지 등을 들 수 있다.Examples of the resin used in the resin composition include thermoplastic resins and thermosetting resins conventionally used in the manufacture of various molded articles, sheets, and films known in the art.
열가소성 수지로는 예컨대 폴리에틸렌 수지, 폴리프로필렌 수지, 폴리시클로올레핀 수지 등의 올레핀계 수지, 폴리(메타)아크릴산에스테르계 수지, 폴리스티렌계 수지, 스티렌-아크릴로니트릴계 수지, 아크릴로니트릴-부타디엔-스티렌계 수지, 폴리염화비닐계 수지, 폴리염화비닐리덴계 수지, 폴리아세트산비닐계 수지, 폴리비닐부티랄계 수지, 에틸렌-아세트산비닐계 공중합체, 에틸렌비닐알코올계 수지, 폴리에틸렌테레프탈레이트 수지, 폴리부틸렌테레프탈레이트 수지, 액정 폴리에스테르 수지 등의 폴리에스테르계 수지, 폴리아세탈 수지, 폴리아미드 수지, 폴리카보네이트 수지, 폴리우레탄 수지 및 폴리페닐렌설파이드 수지 등을 들 수 있다. 이들 수지를 1종 또는 2종 이상의 폴리머 블렌드 혹은 폴리머 알로이로 사용할 수도 있다.Examples of the thermoplastic resin include olefin-based resins such as polyethylene resin, polypropylene resin, and polycycloolefin resin, poly(meth)acrylic acid ester-based resin, polystyrene-based resin, styrene-acrylonitrile-based resin, and acrylonitrile-butadiene-styrene. based resin, polyvinyl chloride based resin, polyvinylidene chloride based resin, polyvinyl acetate based resin, polyvinyl butyral based resin, ethylene-vinyl acetate based copolymer, ethylene vinyl alcohol based resin, polyethylene terephthalate resin, polybutylene polyester resins such as terephthalate resins and liquid crystal polyester resins, polyacetal resins, polyamide resins, polycarbonate resins, polyurethane resins, and polyphenylene sulfide resins; and the like. These resins may be used as one type or a polymer blend or polymer alloy of two or more types.
열경화성 수지로는 예컨대 에폭시 수지, 멜라민 수지, 불포화 폴리에스테르 수지, 페놀 수지, 우레아 수지, 알키드 수지, 열경화성 폴리이미드 수지 등을 들 수 있다.Examples of the thermosetting resin include epoxy resins, melamine resins, unsaturated polyester resins, phenol resins, urea resins, alkyd resins, and thermosetting polyimide resins.
수지 조성물로부터 형성한 고분자 성형품(성형체)의 형상은 평막형, 가루형, 구상 입자형, 파쇄 입자형, 괴상 연속체, 섬유형, 관형, 중공사형, 알갱이형, 판형, 다공질형 등 중 어느 형상일 수도 있다.The shape of the polymer molded article (molded article) formed from the resin composition may be any shape such as flat film, powder, spherical particle, crushed particle, bulky continuum, fibrous, tubular, hollow fiber, granular, plate, porous, etc. there is.
수지 조성물을 자외선 흡수 필터나 자외선 흡수막으로 사용하는 경우, 수지는 투명 수지인 것이 바람직하다.When the resin composition is used as a UV absorbing filter or a UV absorbing film, the resin is preferably a transparent resin.
수지 조성물은 화합물(I)과 수지를 혼합함으로써 얻을 수 있다. 화합물(I)은 원하는 성능을 부여하기 위해 필요한 양을 함유하면 되고, 예컨대 수지 100 질량부에 대해 0.00001 내지 99 질량부 등으로 함유할 수 있다.The resin composition can be obtained by mixing Compound (I) and a resin. Compound (I) may be contained in an amount necessary for imparting desired performance, for example, from 0.00001 to 99 parts by mass with respect to 100 parts by mass of the resin.
수지 조성물은 필요에 따라 용제, 가교 촉매, 태키파이어, 가소제, 연화제, 염료, 안료, 무기 필러 등 기타 첨가물을 포함하고 있을 수 있다.The resin composition may contain other additives such as a solvent, a crosslinking catalyst, a tackifier, a plasticizer, a softener, a dye, a pigment, an inorganic filler, and the like, if necessary.
조성물(1)에 사용되는 중합성 모노머로는 특별히 한정되지 않지만, 라디칼 중합성 모노머인 것이 바람직하고, 광라디칼 중합성 모노머인 것이 보다 바람직하고, (메타)아크릴레이트인 것이 더욱 바람직하다.The polymerizable monomer used in the composition (1) is not particularly limited, but is preferably a radically polymerizable monomer, more preferably an optical radically polymerizable monomer, and still more preferably a (meth)acrylate.
(메타)아크릴레이트로는 분자 내에 1개의 (메타)아크릴로일옥시기를 갖는 단관능 (메타)아크릴레이트 모노머, 분자 내에 2개의 (메타)아크릴로일옥시기를 갖는 2관능 (메타)아크릴레이트 모노머, 분자 내에 3개 이상의 (메타)아크릴로일옥시기를 갖는 다관능 (메타)아크릴레이트 모노머를 들 수 있다.Examples of the (meth)acrylate include a monofunctional (meth)acrylate monomer having one (meth)acryloyloxy group in the molecule, and a bifunctional (meth)acrylate monomer having two (meth)acryloyloxy groups in the molecule. , polyfunctional (meth)acrylate monomers having three or more (meth)acryloyloxy groups in the molecule.
조성물(1)은 추가로 중합 개시제를 포함하는 것이 바람직하다. 중합성 모노머가 라디칼 중합성 모노머인 경우, 중합 개시제는 라디칼 중합 개시제인 것이 바람직하고, 광중합 개시제인 것이 보다 바람직하다.It is preferable that the composition (1) further contains a polymerization initiator. When the polymerizable monomer is a radically polymerizable monomer, the polymerization initiator is preferably a radical polymerization initiator, and more preferably a photopolymerization initiator.
조성물(1)은 화합물(I)과 중합성 모노머를 혼합함으로써 얻을 수 있다. 화합물(I)은 원하는 성능을 부여하기 위해 필요한 양을 함유하면 되고, 예컨대 중합성 모노머 100 질량부에 대해 0.01 내지 20 질량부 등으로 함유할 수 있다.Composition (1) can be obtained by mixing compound (I) and a polymerizable monomer. Compound (I) may be contained in an amount necessary for imparting desired performance, for example, 0.01 to 20 parts by mass or the like per 100 parts by mass of the polymerizable monomer.
조성물(1)은 필요에 따라 용제, 가교 촉매, 태키파이어, 가소제, 연화제, 염료, 안료, 무기 필러 등 기타 첨가물을 포함하고 있을 수 있다.The composition 1 may contain other additives such as a solvent, a crosslinking catalyst, a tackifier, a plasticizer, a softener, a dye, a pigment, an inorganic filler, and the like, if necessary.
<화합물(I)을 포함하는 층><Layer Containing Compound (I)>
본 발명은 식 (I)로 표시되는 부분 구조를 포함하는 양이온을 포함하는 광학층을 포함한다. 식 (I)로 표시되는 부분 구조를 포함하는 양이온을 포함하는 광학층은 통상적으로 화합물(I)을 포함하는 광학층으로부터 형성된다. 화합물(I)을 포함하는 광학층은 예컨대 유기 EL 소자, 액정 셀 등의 표시 소자에 적층시켜 유기 EL 표시장치나 액정 표시장치 등의 화상 표시장치(FPD: 플랫 패널 디스플레이)에 사용할 수 있다. 광학층은 본 발명의 수지 조성물을 사용하여 형성할 수 있다. 본 발명의 수지 조성물을 화상 표시장치에 적용하는 경우, 본 발명의 수지 조성물로부터 형성되는 광학층은 필름층, 점착제층, 코팅층 등 중 어느 것에 적용해도 좋고, 점착제층 또는 코팅층인 것이 바람직하다.The present invention includes an optical layer containing a cation comprising a partial structure represented by formula (I). An optical layer containing a cation containing a partial structure represented by formula (I) is usually formed from an optical layer containing compound (I). The optical layer containing compound (I) can be laminated on, for example, a display element such as an organic EL element or a liquid crystal cell and used for an image display device (FPD: Flat Panel Display) such as an organic EL display device or a liquid crystal display device. The optical layer can be formed using the resin composition of the present invention. When applying the resin composition of the present invention to an image display device, the optical layer formed from the resin composition of the present invention may be applied to any of a film layer, an adhesive layer, a coating layer, and the like, and is preferably an adhesive layer or a coating layer.
화합물(I)을 포함하는 광학층은 상술한 수지 조성물 또는 조성물(1)로부터 형성되는 것이 바람직하다.The optical layer containing compound (I) is preferably formed from the resin composition or composition (1) described above.
화합물(I)을 포함하는 광학층은 화합물(I)을 포함하는 광학층만으로 이루어질 수 있으며, 화합물(I)을 포함하는 층과 다른 층이 적층된 광학 적층체일 수도 있다. 다른 층으로는 예컨대 편광 필름(편광자), 위상차 필름, 열가소성 수지 필름, 파장 변환층 등을 들 수 있다. 광학 적층체가 본 발명의 광학층, 점접착제층, 편광 필름의 순서로 적층된 적층체라면, 본 발명의 광학층은 수지 조성물로부터 형성되는 광학층(광학 필름)인 것이 바람직하다. 광학 적층체가 본 발명의 광학층, 열가소성 수지 필름, 점접착제층, 편광 필름의 순서로 적층된 적층체라면, 본 발명의 광학층은 조성물(1)로부터 형성되는 광학층(코팅층)인 것이 바람직하다. 광학 적층체가 위상차 필름, 본 발명의 광학층, 위상차 필름의 순서로 적층된 적층체라면, 본 발명의 광학층은 수지 조성물로부터 형성되는 광학층(점착제층)인 것이 바람직하다. 본 발명의 광학층과 파장 변환층을 적층하는 경우에는 본 발명의 광학층이 파장 변환층보다 더 시인측에 배치되는 것이 바람직하다.The optical layer containing compound (I) may consist of only the optical layer containing compound (I), or may be an optical laminate in which a layer containing compound (I) and other layers are laminated. Other layers include, for example, a polarizing film (polarizer), a retardation film, a thermoplastic resin film, a wavelength conversion layer, and the like. If the optical laminate is a laminate in which the optical layer, adhesive agent layer, and polarizing film of the present invention are laminated in this order, the optical layer of the present invention is preferably an optical layer (optical film) formed from a resin composition. If the optical laminate is a laminate in which the optical layer of the present invention, the thermoplastic resin film, the adhesive layer, and the polarizing film are laminated in this order, the optical layer of the present invention is preferably an optical layer (coating layer) formed from the composition (1). . If the optical laminate is a laminate in which retardation film, the optical layer of the present invention, and the retardation film are laminated in this order, the optical layer of the present invention is preferably an optical layer (adhesive layer) formed from a resin composition. In the case of laminating the optical layer of the present invention and the wavelength conversion layer, it is preferable that the optical layer of the present invention is disposed on the viewing side more than the wavelength conversion layer.
<점착제 조성물><Adhesive composition>
본 발명의 조성물로부터 형성되는 층이 점착제층인 경우, 수지(A), 화합물(I), 가교제(B) 및 실란 화합물(C)을 포함하는 점착제 조성물(이하 점착제 조성물(1)이라 하는 경우가 있다.)로부터 형성된다. 점착제 조성물(1)은 추가로 라디칼 경화성 성분(D), 개시제(E), 화합물(I) 이외의 광 흡수 화합물(F)(이하 광 선택 흡수 화합물(F)이라 하는 경우가 있다.), 대전 방지제 등을 포함하고 있을 수 있고, 라디칼 경화성 성분(D), 개시제(E) 및 광 선택 흡수 화합물(F)로 이루어진 군에서 선택되는 적어도 하나를 포함하는 것이 바람직하다.When the layer formed from the composition of the present invention is a pressure-sensitive adhesive layer, the pressure-sensitive adhesive composition containing the resin (A), the compound (I), the crosslinking agent (B) and the silane compound (C) (hereinafter referred to as the pressure-sensitive adhesive composition (1)) It is formed from The pressure-sensitive adhesive composition (1) further includes a radical curable component (D), an initiator (E), a light absorbing compound (F) other than the compound (I) (hereinafter sometimes referred to as a photoselective absorbing compound (F)), an electrical charge. It may contain an inhibitor, etc., and it is preferable to include at least one selected from the group consisting of a radical curable component (D), an initiator (E), and a photoselective absorption compound (F).
수지(A)는 점착제 조성물에 사용되는 수지라면 특별히 한정되지 않는다. 수지(A)는 파장 300 nm 내지 파장 780 nm의 범위에서 극대 흡수를 나타내지 않는 것이 바람직하다.Resin (A) is not particularly limited as long as it is a resin used for the pressure-sensitive adhesive composition. It is preferable that the resin (A) does not show maximum absorption in the wavelength range of 300 nm to 780 nm.
수지(A)는 유리 전이 온도(Tg)가 40 ℃이하인 수지인 것이 바람직하다. 수지(A)의 유리 전이 온도(Tg)는 20 ℃이하인 것이 보다 바람직하고, 10 ℃이하인 것이 더욱 바람직하고, 0 ℃이하인 것이 특히 바람직하다. 또한 수지(A)의 유리 전이 온도는 통상적으로 -80 ℃이상이며, -70 ℃이상인 것이 바람직하고, -60 ℃이상인 것이 보다 바람직하고, -55 ℃이상인 것이 더욱 바람직하고, -50 ℃이상인 것이 특히 바람직하다. 수지(A)의 유리 전이 온도가 40 ℃이하이면, 점착제 조성물(1)로부터 형성되는 점착제층의 피착체에 대한 밀착성 향상에 유리하다. 또한 수지(A)의 유리 전이 온도가 -80 ℃이상이면, 점착제 조성물(1)로부터 형성되는 점착제층의 내구성 향상에 유리하다. 또, 유리 전이 온도는 시차주사 열량계(DSC)에 의해 측정할 수 있다.Resin (A) is preferably a resin having a glass transition temperature (Tg) of 40°C or less. The glass transition temperature (Tg) of the resin (A) is more preferably 20°C or lower, still more 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 or higher, still more preferably -55°C or higher, particularly -50°C or higher. desirable. When 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 (1) to the adherend. Moreover, if the glass transition temperature of resin (A) is -80 degreeC or more, it is advantageous to improve the durability of the adhesive layer formed from the adhesive composition (1). In addition, the glass transition temperature can be measured by a differential scanning calorimeter (DSC).
수지(A)로는 (메타)아크릴계 수지, 실리콘계 수지, 고무계 수지, 우레탄계 수지 등을 들 수 있고, (메타)아크릴계 수지인 것이 바람직하다.Examples of the resin (A) include (meth)acrylic resins, silicone resins, rubber resins, urethane resins, and the like, and (meth)acrylic resins are preferred.
(메타)아크릴계 수지로는 (메타)아크릴산에스테르 유래의 구성 단위를 주 성분(바람직하게 50 질량% 이상 포함한다)으로 하는 중합체인 것이 바람직하다. (메타)아크릴계 수지는 1종 이상의 (메타)아크릴산에스테르 이외의 단량체에서 유래된 구성 단위(예컨대 수산기, 카복실기, 아미노기 등의 극성 관능기를 갖는 단량체에서 유래된 구성 단위)를 포함할 수도 있다.The (meth)acrylic resin is preferably a polymer containing a structural unit derived from (meth)acrylic acid ester as a main component (preferably containing 50% by mass or more). The (meth)acrylic resin may include structural units derived from monomers other than one or more (meth)acrylic acid esters (for example, structural units derived from monomers having polar functional groups such as hydroxyl groups, carboxyl groups, and amino groups).
수지(A)의 함유량은 점착제 조성물(1)의 고형분 100 질량% 중, 통상적으로 50 질량% 내지 99.9 질량%이며, 바람직하게 60 질량% 내지 95 질량%이며, 보다 바람직하게 70 질량% 내지 90 질량%이다.The content of the resin (A) is usually 50% by mass to 99.9% by mass, preferably 60% by mass to 95% by mass, more preferably 70% by mass to 90% by mass, based on 100% by mass of the solid content of the pressure-sensitive adhesive composition (1). %to be.
화합물(I)의 함유량은 수지(A) 100 질량부에 대해 통상적으로 0.01 내지 20 질량부이며, 바람직하게 0.1 내지 20 질량부이며, 보다 바람직하게 0.2 내지 10 질량부이며, 특히 바람직하게 0.5 내지 5 질량부이다.The content of compound (I) is usually 0.01 to 20 parts by mass, preferably 0.1 to 20 parts by mass, more preferably 0.2 to 10 parts by mass, particularly preferably 0.5 to 5 parts by mass, based on 100 parts by mass of the resin (A). is the mass part.
가교제(B)로는 이소시아네이트계 가교제, 에폭시계 가교제, 아지리딘계 가교제, 금속 킬레이트계 가교제 등을 들 수 있고, 특히 점착제 조성물의 포트 라이프 및 점착제층의 내구성, 가교 속도 등의 관점에서 이소시아네이트계 가교제인 것이 바람직하다.Examples of the crosslinking agent (B) include isocyanate-based crosslinking agents, epoxy-based crosslinking agents, aziridine-based crosslinking agents, metal chelate-based crosslinking agents, and the like, and in particular, isocyanate-based crosslinking agents are preferred from the viewpoint of the pot life of the pressure-sensitive adhesive composition, durability of the pressure-sensitive adhesive layer, and crosslinking rate. desirable.
가교제(B)의 함유량은 수지(A) 100 질량부에 대해 통상적으로 0.01 내지 25 질량부이며, 바람직하게 0.1 내지 15 질량부이며, 보다 바람직하게 0.15 내지 7 질량부이며, 더욱 바람직하게 0.2 내지 5 질량부이며, 특히 바람직하게 0.25 내지 2 질량부이다.The content of the crosslinking agent (B) is usually 0.01 to 25 parts by mass, preferably 0.1 to 15 parts by mass, more preferably 0.15 to 7 parts by mass, still more preferably 0.2 to 5 parts by mass, based on 100 parts by mass of the resin (A). It is a mass part, It is 0.25-2 mass parts especially preferably.
실란 화합물(C)로는 예컨대 비닐트리메톡시실란, 비닐트리에톡시실란, 비닐트리스(2-메톡시에톡시)실란, 3-글리시독시프로필트리메톡시실란, 3-글리시독시프로필트리에톡시실란, 3-글리시독시프로필메틸디메톡시실란, 3-글리시독시프로필에톡시디메틸실란, 2-(3,4-에폭시시클로헥실)에틸트리메톡시실란, 3-클로로프로필메틸디메톡시실란, 3-클로로프로필트리메톡시실란, 3-메타크릴로일옥시프로필트리메톡시실란, 3-메르캅토프로필트리메톡시실란 등을 들 수 있다.Examples of the silane compound (C) include vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris(2-methoxyethoxy)silane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropyltrie Toxysilane, 3-glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropylethoxydimethylsilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3-chloropropylmethyldimethoxysilane , 3-chloropropyltrimethoxysilane, 3-methacryloyloxypropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, etc. are mentioned.
실란 화합물(C)은 실리콘 올리고머일 수도 있다.The silane compound (C) may be a silicone oligomer.
실란 화합물(C)의 함유량은 수지(A) 100 질량부에 대해 통상적으로 0.01 내지 20 질량부이며, 바람직하게 0.1 내지 10 질량부이며, 보다 바람직하게 0.15 내지 7 질량부이며, 더욱 바람직하게 0.2 내지 5 질량부이며, 특히 바람직하게 0.25 내지 2 질량부이다.The content of the silane compound (C) is usually 0.01 to 20 parts by mass, preferably 0.1 to 10 parts by mass, more preferably 0.15 to 7 parts by mass, still more preferably 0.2 to 20 parts by mass, based on 100 parts by mass of the resin (A). 5 parts by mass, particularly preferably 0.25 to 2 parts by mass.
라디칼 경화성 성분(D)으로는 라디칼 중합 반응에 의해 경화하는 화합물 또는 올리고머 등의 라디칼 경화성 성분을 들 수 있다.Examples of the radical curable component (D) include radical curable components such as compounds or oligomers that are cured by a radical polymerization reaction.
라디칼 중합성 성분(D)으로는 (메타)아크릴레이트계 화합물, 스티렌계 화합물, 비닐계 화합물 등을 들 수 있다.Examples of the radically polymerizable component (D) include (meth)acrylate-based compounds, styrene-based compounds, and vinyl-based compounds.
점착제 조성물(1)은 라디칼 경화성 성분(D)을 2종 이상 포함하고 있을 수 있다.The pressure-sensitive adhesive composition (1) may contain two or more kinds of radical curable components (D).
(메타)아크릴레이트계 화합물로는 분자 내에 적어도 1개의 (메타)아크릴로일옥시기를 갖는 (메타)아크릴레이트 모노머, (메타)아크릴아미드 모노머, 및 분자 내에 적어도 2개의 (메타)아크릴로일기를 갖는 (메타)아크릴 올리고머 등의 (메타)아크릴로일기 함유 화합물을 들 수 있다. (메타)아크릴 올리고머는 바람직하게 분자 내에 적어도 2개의 (메타)아크릴로일옥시기를 갖는 (메타)아크릴레이트 올리고머이다. (메타)아크릴레이트계 화합물은 1종만을 단독으로 사용할 수 있으며 2종 이상을 병용할 수도 있다.As the (meth)acrylate-based compound, a (meth)acrylate monomer having at least one (meth)acryloyloxy group in a molecule, a (meth)acrylamide monomer, and at least two (meth)acryloyl groups in a molecule and (meth)acryloyl group-containing compounds such as (meth)acrylic oligomers having. The (meth)acrylic oligomer is preferably a (meth)acrylate oligomer having at least two (meth)acryloyloxy groups in the molecule. A (meth)acrylate-type compound can be used individually by 1 type, and may use 2 or more types together.
(메타)아크릴레이트 모노머로는 분자 내에 1개의 (메타)아크릴로일옥시기를 갖는 단관능 (메타)아크릴레이트 모노머, 분자 내에 2개의 (메타)아크릴로일옥시기를 갖는 2관능 (메타)아크릴레이트 모노머, 분자 내에 3개 이상의 (메타)아크릴로일옥시기를 갖는 다관능 (메타)아크릴레이트 모노머를 들 수 있다.Examples of the (meth)acrylate monomer include 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. Monofunctional (meth)acrylate monomers having three or more (meth)acryloyloxy groups in the molecule are exemplified.
(메타)아크릴레이트 화합물인 것이 바람직하고, 다관능 (메타)아크릴레이트 화합물인 것이 보다 바람직하다. 다관능 (메타)아크릴레이트 화합물은 3관능 이상인 것이 바람직하다.It is preferable that it is a (meth)acrylate compound, and it is more preferable that it is a polyfunctional (meth)acrylate compound. It is preferable that the polyfunctional (meth)acrylate compound is more than trifunctional.
라디칼 경화성 성분(D)의 함유량은 수지(A) 100 질량부에 대해 통상적으로 0.5 내지 100 질량부이며, 1 내지 70 질량부인 것이 바람직하고, 3 내지 50 질량부인 것이 보다 바람직하고, 5 내지 30 질량부인 것이 더욱 바람직하고, 7.5 내지 25 질량부인 것이 특히 바람직하다.The content of the radical curable component (D) is usually 0.5 to 100 parts by mass, preferably 1 to 70 parts by mass, more preferably 3 to 50 parts by mass, and 5 to 30 parts by mass relative to 100 parts by mass of the resin (A). It is more preferable that it is negative, and it is particularly preferable that it is 7.5 to 25 parts by mass.
개시제(E)는 열의 에너지를 흡수함으로써 중합 반응을 일으키는 화합물(열중합 개시제), 빛의 에너지를 흡수함으로써 중합 반응을 일으키는 화합물(광중합 개시제) 중 어느 것이라도 좋다. 또, 여기서 빛이란 가시광선, 자외선, X선, 또는 전자선과 같은 활성 에너지선인 것이 바람직하다.The initiator (E) may be either a compound that causes a polymerization reaction by absorbing heat energy (thermal polymerization initiator) or a compound that causes a polymerization reaction by absorbing light energy (photopolymerization initiator). In addition, the light herein is preferably an active energy ray such as visible light, ultraviolet rays, X-rays, or electron beams.
열중합 개시제로는 가열 등에 의해 라디칼을 발생하는 화합물(열라디칼 발생제), 가열 등에 의해 산을 발생하는 화합물(열산 발생제), 가열 등에 의해 염기를 발생하는 화합물(열 염기 발생제) 등을 들 수 있다.Examples of the thermal polymerization initiator include compounds that generate radicals by heating (thermal radical generators), compounds that generate acids by heating (thermal acid generators), compounds that generate bases by heating (thermal base generators), and the like. can be heard
광중합 개시제로는 빛의 에너지를 흡수함으로써 라디칼을 발생하는 화합물(광라디칼 발생제), 빛의 에너지를 흡수함으로써 산을 발생하는 화합물(광산 발생제), 빛의 에너지를 흡수함으로써 염기를 발생하는 화합물(광 염기 발생제) 등을 들 수 있다.Photopolymerization initiators include compounds that generate radicals by absorbing light energy (photoradical generators), compounds that generate acids by absorbing light energy (photoacid generators), and compounds that generate bases by absorbing light energy. (Photo base generator) etc. are mentioned.
개시제(E)는 상술한 라디칼 경화성 성분(D)의 중합 반응에 적합한 것을 선택하는 것이 바람직하고, 라디칼 중합 개시제인 것이 바람직하고, 광라디칼 중합 개시제인 것이 보다 바람직하다.The initiator (E) is preferably selected from those suitable for the polymerization reaction of the above-described radical curable component (D), preferably a radical polymerization initiator, and more preferably an optical radical polymerization initiator.
라디칼 중합 개시제는 예컨대 알킬페논 화합물, 벤조인 화합물, 벤조페논 화합물, 옥심에스테르 화합물, 포스핀 화합물 등을 들 수 있다. 라디칼 중합 개시제는 광라디칼 중합 개시제인 것이 바람직하고, 중합 반응의 반응성 관점에서 옥심에스테르계 광라디칼 중합 개시제인 것이 보다 바람직하다. 옥심에스테르계 광라디칼 중합 개시제를 사용함으로써, 조도 또는 광량이 약한 경화 조건이라도 라디칼 경화 성분(D)의 반응률을 높일 수 있다.Examples of the radical polymerization initiator include alkylphenone compounds, benzoin compounds, benzophenone compounds, oxime ester compounds, and phosphine compounds. The radical polymerization initiator is preferably an optical radical polymerization initiator, and more preferably an oxime ester-based radical optical polymerization initiator from the viewpoint of the reactivity of the polymerization reaction. By using an oxime ester-based radical photopolymerization initiator, the reaction rate of the radical curing component (D) can be increased even under curing conditions where the intensity of illumination or the amount of light is low.
개시제(E)의 함유량은 수지(A) 100 질량부에 대해 통상적으로 0.01 내지 20 질량부이며, 0.3 내지 10 질량부인 것이 바람직하고, 0.5 내지 5 질량부인 것이 보다 바람직하고, 0.75 내지 4 질량부인 것이 더욱 바람직하고, 특히 바람직하게 1 내지 3 질량부이다.The content of the initiator (E) is usually 0.01 to 20 parts by mass, preferably 0.3 to 10 parts by mass, more preferably 0.5 to 5 parts by mass, and 0.75 to 4 parts by mass relative to 100 parts by mass of the resin (A). More preferably, it is 1 to 3 parts by mass particularly preferably.
광 선택 흡수 화합물(F)은 화합물(I) 이외의 광흡수성 화합물이며, 예컨대 파장 250 nm 내지 파장 380 nm (바람직하게 파장 250 nm 이상 파장 360 nm 미만)의 빛을 흡수하는 화합물(자외선 흡수제)이나, 파장 380 내지 파장 780 nm를 흡수하는 화합물(색소)이나, 파장 780 nm 내지 파장 1500 nm를 흡수하는 화합물(적외선 흡수제)이다.The light-selective absorbing compound (F) is a light-absorbing compound other than compound (I), for example, a compound (ultraviolet absorber) that absorbs light of a wavelength of 250 nm to 380 nm (preferably a wavelength of 250 nm or more and a wavelength of less than 360 nm) , A compound (dye) that absorbs a wavelength of 380 to 780 nm, or a compound (infrared absorber) that absorbs a wavelength of 780 nm to 1500 nm.
자외선 흡수제는 파장 250 nm 내지 파장 380 nm의 빛을 흡수하는 화합물이면 그 구조는 특별히 한정되지 않지만, 벤조트리아졸계 화합물, 벤조페논계 화합물, 트리아진계 화합물, 살리실산계 화합물, 시아노아크릴레이트계 화합물, 벤조옥사진계 화합물 등의 화합물 등이 바람직하다.The structure of the ultraviolet absorber is not particularly limited as long as it is a compound that absorbs light with a wavelength of 250 nm to 380 nm, but benzotriazole-based compounds, benzophenone-based compounds, triazine-based compounds, salicylic acid-based compounds, cyanoacrylate-based compounds, Compounds, such as a benzoxazine type compound, etc. are preferable.
광 선택 흡수 화합물(F)의 함유량은 수지(A) 100 질량부에 대해 통상적으로 0.1 내지 50 질량부이며, 바람직하게 0.2 내지 40 질량부이며, 보다 바람직하게 0.5 내지 30 질량부이며, 더욱 바람직하게 1 내지 25 질량부이며, 특히 바람직하게 2 내지 20 질량부이다.The content of the photoselective absorbing compound (F) is usually 0.1 to 50 parts by mass, preferably 0.2 to 40 parts by mass, more preferably 0.5 to 30 parts by mass, and still more preferably based on 100 parts by mass of the resin (A). 1 to 25 parts by mass, particularly preferably 2 to 20 parts by mass.
<화합물(I)에 의해 염색된 염색물><Dyeing material dyed by compound (I)>
본 발명은 화합물(I)에 의해 염색된 염색물(예컨대 섬유품, 필름, 수지 등)을 포함한다. 화합물(I)에 의한 염색은 예컨대 화합물(I)을 용제에 용해시킨 용해액에 섬유, 필름, 수지 등의 물품을 침지시킴으로써 실시된다.The present invention includes dyes (eg, textiles, films, resins, etc.) dyed with Compound (I). Dyeing with Compound (I) is performed, for example, by immersing articles such as fibers, films, and resins in a solution obtained by dissolving Compound (I) in a solvent.
이하 실시예 및 비교예에 의해 본 발명을 더욱 상세하게 설명한다. 실시예 및 비교예 중의 "%" 및 "부"는 특별히 명기하지 않는 한, "질량%" 및 "질량부"이다.The present invention will be described in more detail by the following Examples and Comparative Examples. "%" and "parts" in Examples and Comparative Examples are "% by mass" and "parts by mass" unless otherwise specified.
실시예 1: 식 (1)로 표시되는 화합물의 합성Example 1: Synthesis of Compound Represented by Formula (1)
[화학식 30][Formula 30]
Figure PCTKR2022010249-appb-I000030
Figure PCTKR2022010249-appb-I000030
딤로 냉각관 및 온도계를 설치한 500 mL-4구 플라스크 내를 질소 분위기로 하고, 식 (M-1)로 표시되는 화합물(7-히드록시-2,3,4,4a,5,6-헥사히드로나프탈렌-2-온) 25부, 에탄올 150부, 수산화칼륨 10.3부, 파라톨루엔설포닐시아나이드 33.11부를 가하여 빙욕 중에서 4 시간 교반하였다. 얻어진 혼합물로부터 용매를 증류제거한 후, 정제하여 식 (M-2)로 표시되는 화합물 17.4부를 얻었다.In a 500 mL-4-necked flask equipped with a dimro cooling tube and a thermometer, a nitrogen atmosphere was set, and the compound represented by the formula (M-1) (7-hydroxy-2,3,4,4a,5,6-hexa 25 parts of hydronaphthalen-2-one), 150 parts of ethanol, 10.3 parts of potassium hydroxide, and 33.11 parts of p-toluenesulfonylcyanide were added, and the mixture was stirred in an ice bath for 4 hours. After distilling off the solvent from the resulting mixture, 17.4 parts of a compound represented by the formula (M-2) were obtained by purification.
딤로 냉각관 및 온도계를 설치한 100 mL-4구 플라스크를 질소 분위기로 하고, 식 (M-2)로 표시되는 화합물 4부, 탈수 아세토니트릴 40부, 디이소프로필에틸아민 6.6부를 가하여 빙욕 교반하였다. 얻어진 혼합물에 트리플루오로메탄설폰산 무수물 7.2부를 가하여 15분 동안 빙욕 교반한 후, 추가로 인돌린 3부를 가하여 2 시간 빙욕 교반하였다. 얻어진 혼합물로부터 용매를 증류제거한 후, 염산과 아세트산에틸을 사용하여 정제하여 식 (1)로 표시되는 화합물을 얻었다.A 100 mL four-necked flask equipped with a dimro cooling tube and a thermometer was placed in a nitrogen atmosphere, 4 parts of the compound represented by the formula (M-2), 40 parts of dehydrated acetonitrile, and 6.6 parts of diisopropylethylamine were added and stirred in an ice bath. . 7.2 parts of trifluoromethanesulfonic acid anhydride was added to the obtained mixture and stirred in an ice bath for 15 minutes, and then 3 parts of indoline was further added and stirred in an ice bath for 2 hours. After distilling off the solvent from the obtained mixture, it was purified using hydrochloric acid and ethyl acetate to obtain a compound represented by formula (1).
LC-MS 측정 및 1H-NMR 해석을 수행하여 식 (1)로 표시되는 화합물이 생성된 것을 확인하였다. 또한 에너지 분산형 X선 분광법(SEM-EDX 분석)에 의해 클로라이드 음이온의 존재를 확인하였다.LC-MS measurement and 1 H-NMR analysis were conducted to confirm that the compound represented by Formula (1) was produced. In addition, the presence of chloride anion was confirmed by energy dispersive X-ray spectroscopy (SEM-EDX analysis).
1H-NMR(중디메틸설폭시드)δ: 7.07 ~ 7.42 (m, 8H), 5.95 (s, 1H), 4.11 ~ 4.16 (m, 4H), 2.99 ~ 3.20 (m, 5H), 2.50 (m, 2H), 2.05 (m, 2H), 1. 56 (m, 4H) 1 H-NMR (dimethyl sulfoxide) δ: 7.07 to 7.42 (m, 8H), 5.95 (s, 1H), 4.11 to 4.16 (m, 4H), 2.99 to 3.20 (m, 5H), 2.50 (m, 2H), 2.05 (m, 2H), 1.56 (m, 4H)
LC-MS; [M] = 392.5LC-MS; [M] = 392.5
<극대 흡수 파장 및 그램 흡광 계수 ε 측정><Maximum absorption wavelength and gram extinction coefficient ε measurement>
얻어진 식 (1)로 표시되는 화합물의 2-부탄온 용액(0.003 g/L)을 1 cm의 석영 셀에 넣고, 석영 셀을 분광 광도계 UV-2450(가부시키가이샤 시마즈 세이사쿠쇼제)에 세팅하여 더블빔법에 의해 1 nm 스텝별로 300 내지 800 nm의 파장 범위의 흡광도를 측정하였다.A 2-butanone solution (0.003 g/L) of the compound represented by the obtained formula (1) was placed in a 1 cm quartz cell, and the quartz cell was set in a spectrophotometer UV-2450 (manufactured by Shimadzu Seisakusho Co., Ltd.). Absorbance was measured in the wavelength range of 300 to 800 nm for each 1 nm step by the double beam method.
얻어진 흡광도의 값과, 용액 중의 식 (1)로 표시되는 화합물의 농도, 석영 셀의 광로 길이로부터 파장별 그램 흡광 계수를 산출하였다.The gram extinction coefficient for each wavelength was calculated from the obtained absorbance value, the concentration of the compound represented by Formula (1) in the solution, and the optical path length of the quartz cell.
ε(λ) = A(λ)/CLε(λ) = A(λ)/CL
〔식 중, ε(λ)는 파장 λ nm에서의 식 (1)로 표시되는 화합물의 그램 흡광 계수(L/(g·cm))를 나타내고, A(λ)는 파장 λ nm에서의 흡광도를 나타내고, C는 농도(g/L)를 나타내고, L은 석영 셀의 광로 길이(m)를 나타낸다. 〕[Wherein, ε(λ) represents the gram extinction coefficient (L/(g cm)) of the compound represented by formula (1) at a wavelength of λ nm, and A(λ) represents the absorbance at a wavelength of λ nm where C represents the concentration (g/L), and L represents the optical path length (m) of the quartz cell. ]
얻어진 식 (1)로 표시되는 화합물의 극대 흡수 파장은 509 nm이었다. 얻어진 식 (1)로 표시되는 화합물의 극대 흡수 파장에서의 그램 흡광 계수 ε(λmax)는 52 L/(g·cm)이었다.The maximum absorption wavelength of the obtained compound represented by Formula (1) was 509 nm. The gram extinction coefficient ε (λmax) at the maximum absorption wavelength of the compound represented by the obtained formula (1) was 52 L/(g·cm).
또한 측정한 흡광도로부터 극대 흡수 파장의 흡광도의 절반인 흡광도가 되는 2점의 파장을 확인하였다. 2점의 파장 중, 장파측 파장에서 단파측 파장을 빼서 반값 전폭으로 하였다. 식 (1)로 표시되는 화합물의 반값 전폭은 67 nm이었다.In addition, from the measured absorbance, two wavelengths at which the absorbance was half of the absorbance at the maximum absorption wavelength were confirmed. Among the two wavelengths, the wavelength on the short wave side was subtracted from the wavelength on the long wave side to obtain the full width at half maximum. The full width at half maximum of the compound represented by formula (1) was 67 nm.
중합예 1: 아크릴 수지(A1)의 제조Polymerization Example 1: Preparation of Acrylic Resin (A1)
냉각관, 질소 도입관, 온도계 및 교반기를 구비한 반응 용기에, 용매로서 아세트산에틸 81.8부, 아크릴산부틸 96부, 아크릴산 2-히드록시에틸메틸 3부 및 아크릴산 1부의 혼합 용액을 주입하고, 질소 가스로 장치 내 공기를 치환하여 산소 불포함으로 하면서 내부 온도를 55 ℃로 올렸다. 그 후, 아조비스이소부티로니트릴(중합 개시제) 0.14부를 아세트산에틸 10부에 녹인 용액을 전량 첨가하였다. 개시제 첨가 후 1 시간 이 온도에서 유지하고, 이어서 내부 온도를 54 내지 56 ℃로 유지하면서 아세트산에틸을 첨가 속도 17.3부/hr로 반응 용기 내로 연속적으로 가하여, 아크릴 수지의 농도가 35%가 된 시점에서 아세트산에틸의 첨가를 멈추고, 추가로 아세트산에틸의 첨가 개시부터 12 시간 경과할 때까지 이 온도에서 보온하였다. 마지막으로 아세트산에틸을 가하여 아크릴 수지의 농도가 20%가 되도록 조절하여 아크릴 수지의 아세트산에틸 용액을 제조하였다. 얻어진 아크릴 수지는 GPC에 의한 폴리스티렌 환산의 중량 평균 분자량 Mw가 140만, Mw/Mn이 5.5이었다. 이것을 아크릴 수지(A1)로 한다.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 as a solvent was injected into a reaction vessel equipped with a cooling pipe, a nitrogen inlet pipe, a thermometer and a stirrer, and nitrogen gas The air in the apparatus was purged with a furnace to make it free of oxygen, while raising the internal temperature to 55°C. Thereafter, a solution in which 0.14 parts of azobisisobutyronitrile (polymerization initiator) was dissolved in 10 parts of ethyl acetate was added in whole amount. The temperature was maintained at this temperature for 1 hour after addition of the initiator, and then ethyl acetate was continuously added into the reaction vessel at an addition rate of 17.3 parts/hr while maintaining the internal temperature at 54 to 56° C., at which point the acrylic resin concentration reached 35%. The addition of ethyl acetate was stopped, and the mixture was kept warm at this temperature until 12 hours elapsed from the start of addition of ethyl acetate. Finally, ethyl acetate was added to adjust the concentration of the acrylic resin to 20% to prepare an ethyl acetate solution of the acrylic resin. The obtained acrylic resin had a weight average molecular weight Mw of 1,400,000 and Mw/Mn of 5.5 in terms of polystyrene by GPC. Let this be an acrylic resin (A1).
실시예 2: 수지 조성물(1)(점착제 조성물(1))의 제조Example 2: Preparation of Resin Composition (1) (Adhesive Composition (1))
아크릴 수지(A1)의 아세트산에틸 용액(수지 농도: 20%)의 고형분 100부에 대해, 가교제(도소 가부시키가이샤제: 상품명 "코로네이트 L", 이소시아네이트계 화합물, 고형분 75%) 0.5부, 실란 화합물(신에츠 가가쿠고교 가부시키가이샤제: 상품명 "KBM3066") 0.28부, 식 (1)로 표시되는 화합물 0.5부를 혼합하고, 추가로 고형분 농도가 14%가 되도록 2-부탄온을 첨가하여 수지 조성물(1)(점착제 조성물)을 얻었다. 또, 상기 가교제의 배합량은 유효 성분으로서의 질량부 수이다.0.5 part of a crosslinking agent (manufactured by Tosoh Corporation: trade name "Coronate L", isocyanate compound, solid content 75%) 0.5 part, silane A resin composition by mixing 0.28 part of a compound (manufactured by Shin-Etsu Chemical Industry Co., Ltd.: trade name "KBM3066") and 0.5 part of a compound represented by formula (1), and further adding 2-butanone so that the solid content concentration is 14% (1) (Adhesive composition) was obtained. In addition, the blending amount of the crosslinking agent is the number of parts by mass as an active ingredient.
실시예 3, 비교예 1: 수지 조성물(2), (3)의 제조Example 3, Comparative Example 1: Preparation of resin compositions (2) and (3)
표 9에 나타낸 바와 같이 각 성분 및 각 성분의 함유량을 바꾼 것 이외에는 실시예 2과 동일하게 하여 수지 조성물(2), 수지 조성물(3)을 제작하였다. 또, 가교제의 배합량은 유효 성분으로서의 질량부 수이며, 수지(A)는 고형분의 질량부 수이다.As shown in Table 9, resin composition (2) and resin composition (3) were produced in the same manner as in Example 2, except that each component and the content of each component were changed. In addition, the mixing amount of the crosslinking agent is the number of parts by mass as an active ingredient, and the number of parts by mass of the solid content of the resin (A).
실시예Example 비교예comparative example
22 33 1One
수지 조성물 No.Resin composition No. 1One 22 33
수지（Ａ）Resin (A) (A1)(A1) 100100 100100 100100
화합물（Ｉ）Compound (I) 식 (1)Equation (1) 0.50.5 1.01.0
가교제cross-linking agent 코로네이트 LCoronate L 0.50.5 0.50.5 0.50.5
실란 화합물silane compound KBM3066KBM3066 0.280.28 0.280.28 0.280.28
식 (B)Formula (B) 1.01.0
또한, 표 9에서의 각 약어는 이하의 의미를 나타낸다.In addition, each abbreviation in Table 9 shows the following meaning.
아크릴 수지(A1): 중합예 1에서 합성한 아크릴 수지(A1)Acrylic resin (A1): Acrylic resin (A1) synthesized in Polymerization Example 1
식 (1): 실시예 1에서 합성한 식 (1)로 표시되는 화합물Formula (1): Compound represented by Formula (1) synthesized in Example 1
코로네이트 L: 도소 가부시키가이샤제, 상품명: 코로네이트 L, 이소시아네이트계 가교제Coronate L: manufactured by Tosoh Corporation, trade name: Coronate L, isocyanate-based crosslinking agent
KBM3066: 신에츠 가가쿠고교 가부시키가이샤제, 상품명: KBM3066, 실란 커플링제KBM3066: manufactured by Shin-Etsu Chemical Industry Co., Ltd., trade name: KBM3066, silane coupling agent
식 (B): 미국 특허 제6004536호 명세서를 참조하여 합성한 하기 식 (B)로 표시되는 화합물(3-부틸-2-[3-(-3-부틸-5-페닐-2(3H)-벤졸리리덴)-1-프로펜-1-일]-5-페닐-벤족사졸륨 파라톨루엔설포네이트), 상술한 바와 동일하게 하여 구한 반값 전폭은 44 nm이었다.Formula (B): A compound represented by the following formula (B) synthesized with reference to the specification of US Patent No. 6004536 (3-butyl-2-[3-(-3-butyl-5-phenyl-2(3H)- benzolylidene)-1-propen-1-yl]-5-phenyl-benzoxazolium p-toluenesulfonate), and the full width at half maximum determined in the same manner as described above was 44 nm.
[화학식 31][Formula 31]
Figure PCTKR2022010249-appb-I000031
Figure PCTKR2022010249-appb-I000031
<수지 조성물(1)의 성형체 평가><Evaluation of molded article of resin composition (1)>
〔수지 성형체(1)의 제작〕[Production of Resin Molded Body 1]
얻어진 수지 조성물(1)을 이형 처리가 실시된 폴리에틸렌테레프탈레이트 필름으로 이루어진 세퍼레이트 필름〔린텍 가부시키가이샤로부터 입수한 상품명 "PLR-382190"〕의 이형 처리면에 어플리케이터를 사용하여 도포하고, 100 ℃에서 1분 동안 건조하여 수지 성형체(점착제층)(1)를 제작하였다. 얻어진 수지 성형체(1)의 두께는 20 ㎛이었다.The obtained resin composition (1) was applied using an applicator to the release-treated surface of a separate film made of a polyethylene terephthalate film subjected to release treatment [trade name "PLR-382190" obtained from Lintec Co., Ltd.], and then at 100 ° C. It was dried for 1 minute to prepare a resin molded body (adhesive layer) (1). The thickness of the obtained resin molded body 1 was 20 μm.
〔수지 성형체(1)의 내블리드성 평가〕[Evaluation of bleed resistance of resin molded body 1]
얻어진 수지 성형체(1)의 한쪽 면에 추가로 세퍼레이트 필름을 적층하여 양면 세퍼레이트 필름이 부착된 점착제층을 얻었다. 얻어진 양면 세퍼레이트 필름이 부착된 수지층(1)을 온도 23 내지 25 ℃의 공기 하에 1개월 보관하였다. 보관 후의 양면 세퍼레이트 필름이 부착된 수지 성형체(1)를 현미경을 사용하여 면내 화합물의 결정 석출 유무를 확인하였다. 결정 석출이 없는 경우를 a로 하고, 결정 석출이 있는 경우를 b로 하였다. 평가 결과를 표 10에 나타낸다.A separate film was further laminated on one side of the obtained resin molded body (1) to obtain an adhesive layer with double-sided separate films. The obtained resin layer 1 with double-sided separation films was stored under air at a temperature of 23 to 25°C for one month. The presence or absence of crystal precipitation of the in-plane compound was confirmed using a microscope for the resin molded body 1 with the double-sided separation film after storage. The case without crystal precipitation was designated as a, and the case with crystal precipitation was designated as b. Table 10 shows the evaluation results.
〔수지 성형체(1)의 흡광도 유지율 측정〕[Measurement of Absorbance Retention Rate of Resin Molded Body (1)]
두께 8 ㎛인 편광자의 편면에 접착제층을 사용하여 두께 13 ㎛인 시클로올레핀 필름을 접합한 편광판을 준비하였다.A polarizing plate in which a cycloolefin film having a thickness of 13 μm was bonded to one side of a polarizer having a thickness of 8 μm using an adhesive layer was prepared.
편광판의 편광자측에 수지 성형체(1)를 라미네이터에 의해 접합한 후, 온도 23 ℃, 상대습도 65%의 조건으로 7일 동안 양생하여 시클로올레핀 필름/편광자/수지 성형체(1)/세퍼레이트 필름의 적층체를 얻었다. 얻어진 적층체를 30 cm Х 30 cm 크기로 재단하고 세퍼레이트 필름을 박리하여, 수지 성형체(1)과 무알칼리 유리〔코닝사제 상품명 "EAGLE　XG"〕를 접합하여 시클로올레핀 필름/편광자/수지 성형체(1)/유리의 적층 구조를 갖는 적층체(1-1)를 얻었다.After bonding the resin molded body (1) to the polarizer side of the polarizing plate by a laminator, curing for 7 days under the conditions of a temperature of 23 ° C. and a relative humidity of 65%, cycloolefin film / polarizer / resin molded body (1) / laminate of separate films got a sieve The resulting laminate is cut to a size of 30 cm Х 30 cm, the separate film is peeled off, and the resin molded body (1) and the alkali-free glass (trade name "EAGLE"XG manufactured by Corning) are bonded to form a cycloolefin film/polarizer/resin molded body (1 )/glass laminated body (1-1) was obtained.
얻어진 적층체(1-1)를 온도 63 ℃, 상대습도 50% RH의 조건으로 선샤인 웨더 미터(스가 시켄키 가부시키가이샤제)에 75 시간 투입하여 내후성 시험을 실시하였다. 추출한 적층체(1-1)의 흡광도를 상기와 동일한 방법으로 측정하였다. 측정한 흡광도로부터, 하기 식에 기초하여 파장 500 nm에서의 샘플의 흡광도 유지율을 구하였다. 결과를 표 10에 나타낸다. 흡광도 유지율이 100에 가까운 값일수록 광 선택 흡수 기능의 열화가 없어 양호한 내후성을 갖는 것을 나타낸다.The obtained laminate (1-1) was put into a Sunshine Weather Meter (manufactured by Suga Scientific Instruments Co., Ltd.) for 75 hours at a temperature of 63°C and a relative humidity of 50% RH to conduct a weather resistance test. The absorbance of the extracted laminate (1-1) was measured in the same manner as above. From the measured absorbance, the absorbance retention of the sample at a wavelength of 500 nm was determined based on the following formula. The results are shown in Table 10. The closer the absorbance retention ratio is to 100, the better the weather resistance without deterioration of the light selective absorption function.
또한, 흡광도 유지율을 평가하기 위한 흡수 파장은 측정한 흡광도 중 극대 흡수 파장의 장파장측에서 흡광도가 1 내지 1.5가 되는 파장을 선택하였다. 이는 상기 파장이 분광 측정 장치의 측정 정밀도 상 가장 감도가 좋은 흡광도 영역이기 때문이다.In addition, as the absorption wavelength for evaluating the absorbance retention rate, a wavelength at which the absorbance becomes 1 to 1.5 on the long wavelength side of the maximum absorption wavelength among the measured absorbances was selected. This is because the wavelength is the most sensitive absorbance region in terms of measurement accuracy of the spectroscopic measuring device.
흡광도 유지율(%)Absorbance retention rate (%)
= (내후성 시험 후의 A(500)/내후성 시험 전의 A(500)) Х 100= (A(500) after weathering test/A(500) before weathering test) Х 100
[식 중, A(500)는 적층체(1-1)의 흡광도를 나타낸다.][Wherein, A (500) represents the absorbance of the laminate (1-1).]
수지 조성물(1) 대신에 수지 조성물(2)을 사용하여 수지 성형체(2), 적층체(2-1)를 제작하고 동일하게 평가를 수행하였다. 결과를 표 10에 나타낸다.Using the resin composition (2) instead of the resin composition (1), a resin molded body (2) and a laminated body (2-1) were produced and evaluated in the same manner. The results are shown in Table 10.
수지 조성물(1) 대신에 수지 조성물(3)을 사용하여 수지 성형체(3), 적층체(3-1)를 제작하고 동일하게 평가를 수행하였다. 또, 흡광도 유지율 평가는 파장 510 nm에서 수행하였다. 결과를 표 10에 나타낸다.Using the resin composition (3) instead of the resin composition (1), the resin molded body (3) and the laminated body (3-1) were produced and evaluated in the same manner. In addition, the absorbance retention rate was evaluated at a wavelength of 510 nm. The results are shown in Table 10.
내블리드성bleed resistance 흡광도 유지율Absorbance retention rate
실시예 2Example 2 aa 70.470.4
실시예 3Example 3 aa 79.279.2
비교예 1Comparative Example 1 aa 3.53.5
본 발명의 화합물은 극대 흡수 파장 부근의 빛에 대한 높은 흡수 선택성을 갖는다. 또한 본 발명의 화합물을 포함하는 수지 조성물은 내후성 시험 후에도 높은 흡광도 유지율을 가져 양호한 내후성을 갖는다.The compounds of the present invention have high absorption selectivity for light near the maximum absorption wavelength. In addition, the resin composition containing the compound of the present invention has a high absorbance retention even after a weather resistance test, and thus has good weather resistance.
본 발명은 가시광 영역(파장 400 nm 내지 파장 750 nm, 바람직하게 파장 450 nm 내지 파장 600 nm)의 빛을 효율적으로 흡수하고, 동시에 양호한 내후성을 갖는 신규 화합물을 제공하는 것을 목적으로 한다.An object of the present invention is to provide a novel compound that efficiently absorbs light in the visible light region (wavelength 400 nm to wavelength 750 nm, preferably wavelength 450 nm to wavelength 600 nm) and at the same time has good weather resistance.

Claims (13)

  1. 하기 식 (I)로 표시되는 부분 구조를 포함하는 양이온을 포함하는 화합물.A compound containing a cation containing a partial structure represented by the following formula (I).
    Figure PCTKR2022010249-appb-I000032
    Figure PCTKR2022010249-appb-I000032
    [식 (I) 중,[In formula (I),
    고리 W1 및 고리 W2는 각각 독립적으로 적어도 하나의 이중 결합을 고리의 구성 요소로 갖는 고리 구조를 나타낸다.Ring W 1 and ring W 2 each independently represent a ring structure having at least one double bond as a ring component.
    고리 W1 및 고리 W2는 각각 독립적으로 치환기를 가질 수 있다.Ring W 1 and ring W 2 may each independently have a substituent.
    R1 및 R2는 각각 독립적으로 수소 원자 또는 1가의 치환기를 나타내고, R1 및 R2 중 적어도 한쪽은 1가의 치환기이다.]R 1 and R 2 each independently represent a hydrogen atom or a monovalent substituent, and at least one of R 1 and R 2 is a monovalent substituent.]
  2. 제1항에 있어서,According to claim 1,
    R1 및 R2에서 선택되는 적어도 하나가 전자 흡인성기인 화합물.A compound wherein at least one selected from R 1 and R 2 is an electron withdrawing group.
  3. 제2항에 있어서,According to claim 2,
    R1 및 R2에서 선택되는 적어도 하나가 시아노기, 니트로기, 할로겐화알킬기, 할로겐화아릴기, -CO-R1, -CO-O-R2, -CO-NR3R3k, -CO-S-R4, -CS-R5, -CS-O-R6, -CS-S-R7, -SO-R8, -SO2-R9(R1, R2, R3, R3k, R4, R5, R6, R7, R8 및 R9는 각각 독립적으로 치환기를 가질 수 있는 탄화수소기 또는 할로겐 원자를 나타낸다.), -OCF3, -SCF3, -SF5, -SF3, -SO2H 또는 -SO3H인 화합물.At least one selected from R 1 and R 2 is a cyano group, a nitro group, a halogenated alkyl group, a halogenated aryl group, -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 independently represent a hydrocarbon group which may have a substituent or a halogen atom.), -OCF 3 , -SCF 3 , -SF 5 , -SF 3 , -SO 2 H or A compound that is -SO 3 H.
  4. 제3항에 있어서,According to claim 3,
    R1 및 R2에서 선택되는 적어도 하나가 시아노기인 화합물.A compound in which at least one selected from R 1 and R 2 is a cyano group.
  5. 제1항에 있어서,According to claim 1,
    식 (I)로 표시되는 부분 구조를 포함하는 양이온이 식 (I-A)로 표시되는 양이온인 화합물.A compound wherein the cation containing the partial structure represented by formula (I) is a cation represented by formula (I-A).
    Figure PCTKR2022010249-appb-I000033
    Figure PCTKR2022010249-appb-I000033
    [식 (I-A) 중, [In formula (I-A),
    고리 W1, 고리 W2, R1 및 R2는 각각 상기와 동일한 의미를 나타낸다.Each of ring W 1 , ring W 2 , R 1 and R 2 has the same meaning as described above.
    R3, R4, R5 및 R6은 각각 독립적으로 수소 원자, 복소환기, 치환기를 가질 수 있는 탄소수 1 내지 24의 탄화수소기를 나타내고, 상기 탄화수소기에 포함되는 -CH2- 또는 =CH-는 -O- 또는 -S-에 치환될 수 있다.R 3 , R 4 , R 5 and R 6 each independently represent a hydrogen atom, a heterocyclic group, or a hydrocarbon group having 1 to 24 carbon atoms which may have a substituent, and -CH 2 - or =CH- contained in the hydrocarbon group is - It may be substituted for O- or -S-.
    R3 및 R4는 서로 연결하여 고리를 형성할 수 있다.R 3 and R 4 may be connected to each other to form a ring.
    R5 및 R6은 서로 연결하여 고리를 형성할 수 있다.]R 5 and R 6 may be connected to each other to form a ring.]
  6. 제5항에 있어서,According to claim 5,
    식 (I-A)로 표시되는 양이온이 식 (I-B)로 표시되는 양이온 또는 식 (I-C)로 표시되는 양이온인 화합물.A compound wherein the cation represented by formula (I-A) is a cation represented by formula (I-B) or a cation represented by formula (I-C).
    Figure PCTKR2022010249-appb-I000034
    Figure PCTKR2022010249-appb-I000034
    [식 (I-B) 및 식 (I-C) 중,[In Formula (I-B) and Formula (I-C),
    고리 W1, 고리 W2, R1 및 R2는 각각 상기와 동일한 의미를 나타낸다.Each of ring W 1 , ring W 2 , R 1 and R 2 has the same meaning as described above.
    Ar1 및 Ar2는 각각 독립적으로 치환기를 가질 수 있는 탄소수 6 내지 24의 방향족 탄화수소기를 나타낸다.Ar 1 and Ar 2 each independently represent an aromatic hydrocarbon group having 6 to 24 carbon atoms which may have a substituent.
    R4A 및 R6A는 각각 독립적으로 수소 원자 또는 치환기를 가질 수 있는 탄소수 6 내지 24의 탄화수소기를 나타낸다.R 4A and R 6A each independently represent a hydrogen atom or a hydrocarbon group having 6 to 24 carbon atoms which may have a substituent.
    고리 W3 및 고리 W4는 각각 독립적으로 함질소 복소환기를 나타낸다.]Ring W 3 and Ring W 4 each independently represent a nitrogen-containing heterocyclic group.]
  7. 제1항에 있어서,According to claim 1,
    파장 400 nm 내지 파장 700 nm 사이에 극대 흡수를 나타내는 화합물.A compound exhibiting maximum absorption between a wavelength of 400 nm and a wavelength of 700 nm.
  8. 제1항 내지 제7항 중 어느 한 항에 따른 화합물과 수지를 포함하는 조성물.A composition comprising a compound according to any one of claims 1 to 7 and a resin.
  9. 제1항 내지 제7항 중 어느 한 항에 따른 화합물과 중합성 모노머를 포함하는 조성물.A composition comprising the compound according to any one of claims 1 to 7 and a polymerizable monomer.
  10. 제8항에 따른 조성물로부터 성형되는 성형체.A shaped body molded from the composition according to claim 8.
  11. 제9항에 따른 조성물로부터 성형되는 성형체.A shaped body molded from the composition according to claim 9.
  12. 제1항 내지 제7항 중 어느 한 항에 따른 화합물에 의해 염색된 염색물.A dyed article dyed with the compound according to any one of claims 1 to 7.
  13. 하기 식 (I)로 표시되는 부분 구조를 포함하는 양이온을 포함하는 광학층.Optical layer containing a cation containing a partial structure represented by the following formula (I).
    Figure PCTKR2022010249-appb-I000035
    Figure PCTKR2022010249-appb-I000035
    [식 (I) 중, [In formula (I),
    고리 W1 및 고리 W2는 각각 독립적으로 적어도 하나의 이중 결합을 고리의 구성 요소로 갖는 고리 구조를 나타낸다.Ring W 1 and ring W 2 each independently represent a ring structure having at least one double bond as a ring component.
    고리 W1 및 고리 W2는 각각 독립적으로 치환기를 가질 수 있다.Ring W 1 and ring W 2 may each independently have a substituent.
    R1 및 R2는 각각 독립적으로 수소 원자 또는 1가의 치환기를 나타내고, R1 및 R2 중 적어도 한쪽은 1가의 치환기이다.]R 1 and R 2 each independently represent a hydrogen atom or a monovalent substituent, and at least one of R 1 and R 2 is a monovalent substituent.]
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Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
DATABASE REGISTRY 16 November 1984 (1984-11-16), ANONYMOUS : "2,3-Naphthalenediamine, 6,7-dihydro-6,7-diimino-, conjugate acid (1:2) (CA INDEX NAME)", XP093024336, retrieved from STN Database accession no. 64535-17-7 *
DATABASE REGISTRY 16 November 1984 (1984-11-16), ANONYMOUS : "2-Naphthalenamine, 3,4,4a,5,6,7-hexahydro-N-phenyl-7-(phenylimino)- (CA INDEX NAME)", XP093024334, retrieved from STN Database accession no. 47368-17-2 *
DATABASE REGISTRY 16 November 1984 (1984-11-16), ANONYMOUS : "2-Naphthalenamine, 3,4,4a,5,6,7-hexahydro-N-phenyl-7-(phenylimino)- (CA INDEX NAME)", XP093024339, retrieved from STN Database accession no. 47368-17-2 *
DATABASE REGISTRY 16 November 1984 (1984-11-16), ANONYMOUS : "Methanaminium, N-[7-(dimethylamino)-4,4a,5,6-tetrahydro-2(3H)- naphthalenylidene]-N-methyl- (CA INDEX NAME)", XP093024333, retrieved from STN Database accession no. 46710-61-6 *
ELBL-WEISER KARIN, KRIEGER CLAUS, STAAB HEINZ A.: "Vinyloge Dikationen cyaninartiger Tetrakis(dimethylamino)-Verbindungen", ANGEWANDTE CHEMIE, vol. 102, no. 2, 1 February 1990 (1990-02-01), DE , pages 183 - 185, XP093024342, ISSN: 0044-8249, DOI: 10.1002/ange.19901020207 *

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