WO2020022134A1 - 化合物及びその製造方法 - Google Patents

化合物及びその製造方法 Download PDF

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WO2020022134A1
WO2020022134A1 PCT/JP2019/028047 JP2019028047W WO2020022134A1 WO 2020022134 A1 WO2020022134 A1 WO 2020022134A1 JP 2019028047 W JP2019028047 W JP 2019028047W WO 2020022134 A1 WO2020022134 A1 WO 2020022134A1
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group
compound
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substituent
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French (fr)
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健一郎 大家
三上　智司
廷烋 朴
光敬 佐▲瀬▼
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住友化学株式会社
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Priority to KR1020207037998A priority Critical patent/KR20210034554A/ko
Priority to CN201980048864.1A priority patent/CN112469695A/zh
Publication of WO2020022134A1 publication Critical patent/WO2020022134A1/ja

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    • 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
    • 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
    • C07D207/30—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 two double bonds between ring members or between ring members and non-ring members
    • C07D207/32—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 two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/33—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 two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/335—Radicals substituted by nitrogen atoms not forming part of a nitro radical
    • 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
    • C07D403/14—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 three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B61/00—Other general methods

Definitions

  • the present invention relates to a novel compound and a method for producing the same.
  • Patent Literature 1 discloses that a squarylium-based compound is used for a filter for a plasma display panel capable of effectively cutting neon light emitted from a plasma display.
  • the object of the present invention is to provide a novel compound useful for an optical filter such as a display device and a method for producing the same.
  • R 1 to R 4 each independently represent a hydrogen atom or a monovalent hydrocarbon group having 1 to 6 carbon atoms which may have a substituent.
  • T 1 and T 2 each independently represent a hydrogen atom or a monovalent hydrocarbon group having 1 to 6 carbon atoms which may have a substituent.
  • Y 1 and Y 2 each represent a monovalent aromatic group which may have a substituent, and the other one may represent a monovalent aromatic group which may have a substituent, a hydrogen atom, A halogen atom or a monovalent hydrocarbon group having 1 to 6 carbon atoms which may have a substituent (the hydrocarbon group is a group other than a monovalent aromatic group and is included in the hydrocarbon group; CH 2 — represents —O— or —CO—. ] [2] A compound represented by the formula (II). [Where, R 1 to R 4 each independently represent a hydrogen atom or a monovalent hydrocarbon group having 1 to 6 carbon atoms which may have a substituent.
  • T 1 and T 2 each independently represent a hydrogen atom or a monovalent hydrocarbon group having 1 to 6 carbon atoms which may have a substituent.
  • X 1 and X 2 each represent any group selected from group A, and the other represents any group selected from group A, a hydrogen atom or a carbon atom 1 which may have a substituent.
  • To 6 monovalent hydrocarbon groups (the hydrocarbon group is a group other than a monovalent aromatic group, and —CH 2 — contained in the hydrocarbon group is replaced by —O— or —CO— May be used.)
  • Group A a group consisting of a halogen atom, a borate group, and —B (OH) 2 .
  • R 1 to R 4 each independently represent a hydrogen atom or a monovalent hydrocarbon group having 1 to 6 carbon atoms which may have a substituent.
  • T 1 and T 2 each independently represent a hydrogen atom or a monovalent hydrocarbon group having 1 to 6 carbon atoms which may have a substituent.
  • Y 1a and Y 2a each independently represent a monovalent aromatic group which may have a substituent.
  • T 1 and T 2 represent the same meaning as described above.
  • X 1a and X 2a each independently represent any group selected from Group A.
  • Group A a group consisting of a halogen atom, a borate group, and —B (OH) 2 .
  • Y 1a -Z 1 (III-1a) Y 2a -Z 2 (III-2a) [In the formulas (III-1a) and (III-2a), Y 1a and Y 2a have the same meaning as described above.
  • Z 1 and Z 2 each independently represent a halogen atom, a borate group, —B (OH) 2 , an alkylsulfonate group, or an arylsulfonate group.
  • R 1 to R 4 each independently represent a hydrogen atom or a monovalent hydrocarbon group having 1 to 6 carbon atoms which may have a substituent.
  • T 1 and T 2 each independently represent a hydrogen atom or a monovalent hydrocarbon group having 1 to 6 carbon atoms which may have a substituent.
  • Y 1b represents a monovalent aromatic group which may have a substituent.
  • X 2b represents a hydrogen atom or a monovalent hydrocarbon group having 1 to 6 carbon atoms which may have a substituent (the hydrocarbon group is a group other than a monovalent aromatic group; Represents a —CH 2 — which may be replaced by —O— or —CO—.) ]
  • R 1 to R 4 have the same meaning as described above.
  • T 1 and T 2 represent the same meaning as described above.
  • X 1b represents any group selected from Group A.
  • Group A a group consisting of a halogen atom, a borate group, and —B (OH) 2 .
  • X 2b has the same meaning as described above.
  • Y 1b -Z 1 (III-1b) [Where, Y 1b has the same meaning as described above.
  • Z 1 represents a halogen atom, a borate group, —B (OH) 2 , an alkylsulfonate group, or an arylsulfonate group. ]
  • the compound of the present invention can be suitably used for an optical filter such as a display device.
  • FIG. 1 A and (b) are schematic sectional views showing an example of an optical filter.
  • FIG. 1 A is a schematic sectional view showing an example of an organic EL display device, and
  • FIG. 1 A is a schematic sectional view showing an example of a liquid crystal display device.
  • the present invention relates to a compound represented by the following formula (I) (hereinafter, sometimes referred to as “compound (I)”).
  • R 1 to R 4 each independently represent a hydrogen atom or a monovalent hydrocarbon group having 1 to 6 carbon atoms which may have a substituent.
  • T 1 and T 2 each independently represent a hydrogen atom or a monovalent hydrocarbon group having 1 to 6 carbon atoms which may have a substituent.
  • Y 1 and Y 2 each represent a monovalent aromatic group which may have a substituent, and the other one may represent a monovalent aromatic group which may have a substituent, a hydrogen atom, A halogen atom or a monovalent hydrocarbon group having 1 to 6 carbon atoms which may have a substituent (the hydrocarbon group is a group other than a monovalent aromatic group and is included in the hydrocarbon group; CH 2 — represents —O— or —CO—. ]
  • examples of the monovalent hydrocarbon group having 1 to 6 carbon atoms in R 1 to R 4 include a monovalent saturated hydrocarbon group and a monovalent unsaturated hydrocarbon group.
  • examples of the monovalent saturated hydrocarbon group include a linear alkyl group such as a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, and a hexyl group; A branched chain alkyl group such as a group, an isopentyl group or a neopentyl group; and an alicyclic saturated hydrocarbon group such as a cyclopropyl group, a cyclopentyl group or a cyclohexyl group.
  • Examples of the monovalent unsaturated hydrocarbon group include a phenyl group which is an aromatic hydrocarbon group; a monovalent unsaturated aliphatic hydrocarbon group such as a vinyl group, a propenyl group, a butenyl group, or a pentenyl group; a cyclopropenyl group; Examples thereof include a monovalent alicyclic unsaturated hydrocarbon group such as a cyclopentenyl group or a cyclohexenyl group.
  • examples of the substituent of the optionally substituted monovalent hydrocarbon group having 1 to 6 carbon atoms in R 1 to R 4 include a halogen atom, a hydroxy group, an amino group, and a nitro group.
  • a halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
  • examples of the monovalent hydrocarbon group having 1 to 6 carbon atoms which may have a substituent in T 1 and T 2 include those exemplified for R 1 to R 4 .
  • one of Y 1 and Y 2 may be a monovalent aromatic group which may have a substituent, and both of them independently have a substituent. It may be a monovalent aromatic group which may be substituted.
  • the other is a hydrogen atom, a halogen atom or a monovalent hydrocarbon group having 1 to 6 carbon atoms which may have a substituent.
  • —CH 2 — contained in the hydrocarbon group may be replaced by —O— or —CO—.
  • the monovalent aromatic group which may have a substituent in Y 1 and Y 2 includes a monovalent aromatic hydrocarbon group which may have a substituent or a monovalent aromatic hydrocarbon group which has a substituent. And a monovalent aromatic heterocyclic group which may be substituted.
  • the monovalent aromatic group may have a single ring structure or a condensed ring structure.
  • the monovalent aromatic hydrocarbon group usually has 6 to 30 carbon atoms, preferably 6 to 20 carbon atoms, and more preferably 6 to 13 carbon atoms.
  • Examples of the monovalent aromatic hydrocarbon group include a phenyl group; a naphthyl group; an anthracenyl group; a phenanthryl group; a pyrenyl group; and a fluorenyl group.
  • the hydrogen contained in the above group is an alkyl group (-CH 2- contained in the alkyl group may be replaced by -O- or -CO-), Including those substituted with a hydrocarbon group such as an aryl group, for example, tolyl group, xylyl group, mesityl group, propylphenyl group, butylphenyl group, hexylphenyl group, biphenyl group, terphenyl group, propylbiphenyl And the like.
  • a hydrocarbon group such as an aryl group, for example, tolyl group, xylyl group, mesityl group, propylphenyl group, butylphenyl group, hexylphenyl group, biphenyl group, terphenyl group, propylbiphenyl And the like.
  • the monovalent aromatic heterocyclic group usually has 2 to 30 carbon atoms, preferably 4 to 20, and more preferably 4 to 10.
  • the hetero atom in the monovalent aromatic heterocyclic group represents a nitrogen atom, an oxygen atom, a sulfur atom, or the like.
  • Examples of the monovalent aromatic heterocyclic group include furan, thiophene, pyrrole, oxazole, isoxazole, thiazole, isothiazole, imidazole, pyrazole, furazane, triazole, oxadiazole, isoxazole, tetrazole, pyran, pyridine, thiopyran, Pyridazine, pyrimidine, pyrazine, triazine, benzofuran, isobenzofuran, benzothiophene, indole, isoindole, indolizine, indoline, isoindoline, chromene, isochromene, chroman, isochroman, benzopyran, quinoline, isoquinoline, quinolidine, benzimidazole, benzothiazole , Benzothiadiazole, indazole, naphthyridine, quinoxaline, quinazoline,
  • the monovalent aromatic heterocyclic group includes a group in which hydrogen contained in the above group is substituted with a hydrocarbon group such as an alkyl group and an aryl group.
  • a hydrogen atom is converted from N-biphenylcarbazole. It may be a group excluding one.
  • substituent in the optionally substituted monovalent aromatic group include the above-mentioned halogen atom; hydroxy group; amino group; nitro group; aryloxy group; arylcarbonyl group; Group; sulfo group; carbamoyl group; sulfamoyl group and the like.
  • any one of Y 1 and Y 2 which is a hydrocarbon group other than a monovalent aromatic group and has 1 to 6 carbon atoms which may have a substituent.
  • the hydrocarbon group include a monovalent saturated hydrocarbon group which may have a substituent and a monovalent unsaturated aliphatic hydrocarbon which may have a substituent as exemplified in R 1 to R 4 .
  • a monovalent alicyclic unsaturated hydrocarbon group which may have a group or a substituent.
  • Examples of compound (I) include compounds represented by the following formula.
  • Compound (I) can be used for an optical filter in a display device or the like.
  • an optical filter capable of absorbing light near 580 nm (575 to 590 nm) (preferably light having a maximum absorption wavelength of 580 nm) can be obtained.
  • the light transmitted through the optical filter can increase the separability of green light and red light, and improve the color purity of green light and red light, as compared with light incident on the optical filter. Can be expected. Therefore, a display device with improved color purity can be obtained by applying an optical filter using the compound (I) to a display device or the like.
  • compound (II) The compound of the present invention represented by the following formula (II) (hereinafter sometimes referred to as “compound (II)”) can be used as an intermediate for producing compound (I).
  • R 1 to R 4 each independently represent a hydrogen atom or a monovalent hydrocarbon group having 1 to 6 carbon atoms which may have a substituent.
  • T 1 and T 2 each independently represent a hydrogen atom or a monovalent hydrocarbon group having 1 to 6 carbon atoms which may have a substituent.
  • X 1 and X 2 each represent any group selected from group A, and the other represents any group selected from group A, a hydrogen atom or a carbon atom 1 which may have a substituent.
  • Group A a group consisting of a halogen atom, a borate group, and —B (OH) 2 .
  • the monovalent hydrocarbon group having 1 to 6 carbon atoms which may have a substituent in R 1 to R 4 , T 1 and T 2 includes those described above.
  • one of X 1 and X 2 represents any group selected from Group A, and both may be any groups selected from Group A.
  • the other is a hydrogen atom or a monovalent hydrocarbon group having 1 to 6 carbon atoms which may have a substituent.
  • —CH 2 — contained in the hydrocarbon group may be replaced by —O— or —CO—.
  • examples of the halogen atom in the group A include those described above.
  • examples of the borate group in X 1 and X 2 include groups represented by the following formula. In the following formula, * represents a bond.
  • any one of X 1 and X 2 which is a hydrocarbon group other than a monovalent aromatic group and has 1 to 6 carbon atoms which may have a substituent.
  • Examples of the compound (II) include a compound represented by the following formula.
  • the monovalent hydrocarbon group having 1 to 6 carbon atoms which may have a substituent in R 1 to R 4 , T 1 and T 2 includes those described above.
  • the monovalent aromatic group which may have a substituent in Y 1a and Y 2a in the formula (Ia) has a substituent represented by Y 1 and Y 2 in the above formula (I). Examples of the monovalent aromatic group which may be used include those described above.
  • the method for producing the compound (Ia) includes the steps of: converting a compound represented by the formula (IIa), a compound represented by the formula (III-1a), and a compound represented by the formula (III-2a) into a nickel catalyst or A step of reacting in the presence of a palladium catalyst may be included.
  • R 1 to R 4 have the same meaning as described above.
  • T 1 and T 2 represent the same meaning as described above.
  • X 1a and X 2a each independently represent any group selected from Group A.
  • Group A a group consisting of a halogen atom, a borate group, and —B (OH) 2 .
  • Y 1a -Z 1 (III-1a) Y 2a -Z 2 (III-2a) In the formulas (III-1a) and (III-2a), Y 1a and Y 2a have the same meaning as described above.
  • Z 1 and Z 2 each independently represent a halogen atom, a borate group, —B (OH) 2 , an alkylsulfonate group, or an arylsulfonate group. ]
  • the monovalent hydrocarbon group having 1 to 6 carbon atoms which may have a substituent in R 1 to R 4 , T 1 and T 2 includes those described above.
  • the halogen atom and the borate in Group A of X 1a and X 2a in the formula (IIa) include those described above.
  • the halogen atom and the borate group in Z 1 and Z 2 are as described above.
  • Examples of the alkylsulfonate group for Z 1 and Z 2 include an alkylsulfonate group having 1 to 6 carbon atoms which may have a halogen atom, such as a methanesulfonate group, an ethanesulfonate group, and a trifluoromethanesulfonate group.
  • Examples of the halogen atom include those exemplified above.
  • As the arylsulfonate group for Z 1 and Z 2, an arylsulfonate group having 6 to 18 carbon atoms such as a benzenesulfonate group, a p-toluenesulfonate group and a benzylsulfonate group can be mentioned.
  • Z 1 and Z 2 are each independently a halogen atom, a borate group, or —B (OH) 2 .
  • Examples of the compound represented by the formula (IIa) include a compound represented by the following formula.
  • Compounds represented by the formulas (III-1a) and (III-2a) include 2,6-dimethyl-4- (4,4,5,5-tetramethyl-1,3,2-dioxaborane-2) -Yl) phenol, 3,4,5-trimethoxyphenylboronic acid, 4-hexylphenylboronic acid, 4-hexyloxyphenylboronic acid, 4- (dimethylamino) phenylboronic acid, 4- (diphenylamino) phenylboron Acid, 4'-propyl-4-biphenylboronic acid, 6-ethoxy-2-naphthaleneboronic acid, 9,9-dimethylfluorene-2-boronic acid, benzo [b] thiophen-2-boronic acid, 9-ethylcarbazole 3-boronic acid, 9- (4-biphenylyl) carbazole-3-boronic acid pinacol, 4-tert-butylphenylboronic acid, 4-methoxy 3,5-d
  • a compound represented by the formula (IIa), a compound represented by the formula (III-1a), and a compound represented by the formula (III-2a) are treated with a palladium catalyst
  • a coupling method in the presence or in the presence of a nickel catalyst is preferred, and a coupling method in the presence of a palladium catalyst is most preferred.
  • the palladium catalyst include tetrakis (triphenylphosphine) palladium (0), tris (dibenzylideneacetone) dipalladium (0), palladium (II) acetate, dichlorobistriphenylphosphinepalladium (II), and potassium hexachloropalladium (IV).
  • nickel catalyst examples include tetrakis (triphenylphosphine) nickel (0), [bis (1,5-cyclooctadiene)] nickel (0), [1,3-bis (diphenylphosphino) propane] dichloronickel (II) ), Bis (2,4-pentanedionato) nickel (II), bis (triphenylphosphine) nickel (II) dichloride, nickel (II) halide and the like.
  • the amount of the palladium catalyst or nickel catalyst used is preferably 0.1 mol% or more and 50 mol% or less based on 1 mol of the compound represented by the formula (IIa).
  • the amount of the compound represented by the formula (III-1a) is preferably 1 mol or more and 5 mol or less, more preferably 1.1 mol or more and 3 mol or less with respect to 1 mol of the compound represented by the formula (IIa). It is more preferred that:
  • the amount of the compound represented by the formula (III-2a) to be used is preferably 1 mol or more and 5 mol or less, more preferably 1.1 mol or more and 3 mol or less with respect to 1 mol of the compound represented by the formula (IIa). It is more preferred that:
  • the reaction temperature is preferably 30 ° C to 180 ° C, more preferably 80 ° C to 140 ° C.
  • the reaction time is preferably 1 hour to 20 hours, more preferably 3 hours to 15 hours.
  • the reaction is preferably performed in an organic solvent from the viewpoint of yield.
  • organic solvent include aromatic hydrocarbon solvents such as toluene and xylene; hydrocarbon solvents such as hexane, cyclohexane and decalin; ether solvents such as tetrahydrofuran, 1,4-dioxane and dimethoxyethane; chlorobenzene, dichlorobenzene, chloroform and the like.
  • Alcohol solvents such as methanol, ethanol, isopropanol and butanol; nitrohydrocarbon solvents such as nitrobenzene; ketone solvents such as methyl isobutyl ketone; N, N-dimethylformamide, 1-methyl-2-pyrrolidone Amide solvent; and these may be used as a mixture. Of these, tetrahydrofuran is preferred. Further, the reaction can be carried out by a two-phase or mixed reaction with water, such as a coupling reaction using a palladium catalyst.
  • the amount of the organic solvent to be used is preferably 10 parts by mass or more and 200 parts by mass or less, more preferably 20 parts by mass or more and 150 parts by mass or less with respect to 1 part by mass of the compound represented by the formula (IIa). preferable.
  • a base may be added to the reaction of the compound represented by the formula (IIa), the compound represented by the formula (III-1a), and the compound represented by the formula (III-2a).
  • the base is preferably one that sufficiently dissolves in the solvent used for the reaction.
  • an inorganic base such as sodium carbonate, potassium carbonate, cesium carbonate, potassium fluoride, cesium fluoride, tripotassium phosphate; butyllithium, potassium-tert-butoxide, sodium-tert-butoxide, sodium methoxide;
  • Organic bases such as sodium ethoxide, tetrabutylammonium fluoride, tetrabutylammonium chloride, tetrabutylammonium bromide, tetraethylammonium hydroxide, and tetrabutylammonium hydroxide are exemplified.
  • Examples of the method of mixing the base include a method of adding a base solution while stirring the reaction solution under an inert atmosphere such as argon or nitrogen, and a method of adding the reaction solution to the base solution.
  • the use amount of the base is preferably 2 mol or more and 20 mol or less based on 1 mol of the compound represented by the formula (IIa).
  • the method for obtaining the target compound (Ia) from the reaction mixture is not particularly limited, and various known methods can be employed. For example, there is a method in which the precipitated crystals are collected by filtration after cooling. The crystals collected by filtration are preferably washed with water or the like and then dried. Further, if necessary, it may be further purified by a known method such as recrystallization, column chromatography and the like.
  • Y 1 is a monovalent aromatic group which may have a substituent
  • Y 2 is a hydrogen atom or a carbon atom having 1 to 6 carbon atoms which may have a substituent.
  • a monovalent hydrocarbon group (the hydrocarbon group is a group other than a monovalent aromatic group, and —CH 2 — contained in the hydrocarbon group may be replaced with —O— or —CO—
  • compound (Ib) represented by the following formula (Ib) will be described.
  • R 1 to R 4 each independently represent a hydrogen atom or a monovalent hydrocarbon group having 1 to 6 carbon atoms which may have a substituent.
  • T 1 and T 2 each independently represent a hydrogen atom or a monovalent hydrocarbon group having 1 to 6 carbon atoms which may have a substituent.
  • Y 1b represents a monovalent aromatic group which may have a substituent.
  • X 2b represents a hydrogen atom or a monovalent hydrocarbon group having 1 to 6 carbon atoms which may have a substituent (the hydrocarbon group is a group other than a monovalent aromatic group; Represents a —CH 2 — which may be replaced by —O— or —CO—.) ]
  • the monovalent hydrocarbon group having 1 to 6 carbon atoms which may have a substituent in R 1 to R 4 , T 1 and T 2 is represented by R in the above formula (I) include those exemplified in 1 ⁇ R 4.
  • examples of the optionally substituted monovalent aromatic group for Y 1b include those exemplified for Y 1 and Y 2 in the above formula (I).
  • the monovalent hydrocarbon group having 1 to 6 carbon atoms which may have a substituent in X 2b is exemplified by those exemplified as R 1 to R 4 in the above formula (I). No.
  • the production method of the compound (Ib) includes a step of reacting a compound represented by the formula (IIb) with a compound represented by the formula (III-1b) in the presence of a nickel catalyst or a palladium catalyst. Is also good.
  • R 1 to R 4 have the same meaning as described above.
  • T 1 and T 2 represent the same meaning as described above.
  • X 1b represents any group selected from Group A.
  • Group A a group consisting of a halogen atom, a borate group, and —B (OH) 2 .
  • X 2b has the same meaning as described above.
  • Y 1b -Z 1 (III-1b) [Where, Y 1b has the same meaning as described above. Z 1 represents a halogen atom, a borate group, —B (OH) 2 , an alkylsulfonate group, or an arylsulfonate group. ]
  • the monovalent hydrocarbon group having 1 to 6 carbon atoms which may have a substituent in R 1 to R 4 , T 1 and T 2 , and X 2b is And those exemplified for R 1 to R 4 in the above formula (I).
  • the monovalent aromatic group which may have a substituent in Y 1b is exemplified by Y 1 and Y 2 in the above formula (I) Is mentioned.
  • the halogen atom and the borate group in X 1b include those described above.
  • Examples of the compound represented by the formula (IIb) include a compound represented by the following formula.
  • Examples of the compound represented by the formula (III-1b) include the compounds exemplified as the compounds represented by the formulas (III-1a) and (III-2a) described above.
  • a method of coupling the compound represented by the formula (IIb) and the compound represented by the formula (III-1b) in the presence of a palladium catalyst or a nickel catalyst is known.
  • a coupling method in the presence of a palladium catalyst is most preferable.
  • the palladium catalyst and the nickel catalyst include those described above.
  • the amount of the compound represented by the formula (III-1b) is preferably 1 mol or more and 5 mol or less, more preferably 1.1 mol or more and 3 mol or less, per 1 mol of the compound represented by the formula (IIb). It is more preferred that:
  • the use amount of the palladium catalyst or the nickel catalyst is preferably 0.1 mol% or more and 50 mol% or less based on 1 mol of the compound represented by the formula (IIb).
  • the reaction temperature is preferably 30 ° C to 180 ° C, more preferably 80 ° C to 140 ° C.
  • the reaction time is preferably 1 hour to 20 hours, more preferably 3 hours to 15 hours.
  • the reaction is preferably performed in an organic solvent from the viewpoint of yield.
  • the organic solvent include those exemplified above.
  • the amount of the organic solvent to be used is preferably 10 parts by mass or more and 200 parts by mass or less, more preferably 20 parts by mass or more and 150 parts by mass or less with respect to 1 part by mass of the compound represented by the formula (IIb). preferable.
  • the method for obtaining the target compound (Ib) from the reaction mixture is not particularly limited, and various known methods can be employed, and examples thereof include the above-described methods.
  • the production method of the compound (I) of the present invention is represented by the following formula (IV): squaric acid (3,4-dihydroxy-3-cyclobutene-1,2-dione) or the formula (IV-1) (Hereinafter sometimes referred to as compound (IV-1)), a compound represented by the following formula (V1) (hereinafter sometimes referred to as “pyrrole compound (V1)”), and a compound represented by the following formula: A step of reacting with a compound represented by (V2) (hereinafter, sometimes referred to as “pyrrole compound (V2)”) may be included.
  • R 1 to R 4 have the same meaning as described above.
  • Y 1 and Y 2 each represent a monovalent aromatic group which may have a substituent, and the other one may represent a monovalent aromatic group which may have a substituent, a hydrogen atom, A halogen atom or a monovalent hydrocarbon group having 1 to 6 carbon atoms which may have a substituent (the hydrocarbon group is a group other than a monovalent aromatic group and is included in the hydrocarbon group; CH 2 — represents —O— or —CO—.
  • T 1 and T 2 represent the same meaning as described above.
  • R 11 and R 12 each independently represent an alkyl group having 1 to 4 carbon atoms.
  • the monovalent hydrocarbon group having 1 to 6 carbon atoms which may have a substituent in R 1 to R 4 , T 1 and T 2 is as described above.
  • a monovalent aromatic group which may have a substituent in Y 1 and Y 2 , a halogen atom, and a carbon atom having 1 to 6 carbon atoms which may have a substituent examples include those described above.
  • Examples of the pyrrole compound (V1) and the pyrrole compound (V2) include compounds represented by the following formulas.
  • a method in which squaric acid, a pyrrole compound (V1), and a pyrrole compound (V2) are dehydrated and condensed in an organic solvent is preferable.
  • the organic solvent include those described above, and a mixed solvent of butanol and toluene is preferable.
  • the amount of squaric acid used in the step of reacting squaric acid with the pyrrole compound (V1) and the pyrrole compound (V2) is based on 1 mol of the pyrrole compound (V1) and the pyrrole compound (V2) in total. , 0.45 mol or more and 0.6 mol or less, more preferably 0.47 mol or more and 0.51 mol or less.
  • the amount of the pyrrole compound (V2) to be used is preferably 1 mol or more and 1.5 mol or less per 1 mol of the pyrrole compound (V1).
  • the reaction between the compound represented by the formula (IV) or the compound (IV-1), the pyrrole compound (V1), and the pyrrole compound (V2) is performed by the compound represented by the formula (IV) or the compound (IV -1), a pyrrole compound (V1) and a pyrrole compound (V2).
  • the compound represented by the formula (IV) or the compound (IV-1), the pyrrole compound (V1), and the pyrrole compound (V2) may all be reacted together.
  • a method of mixing the compound represented by the formula (IV) or the compound (IV-1) with the pyrrole compound (1) first, and then mixing the pyrrole compound (2) A method in which the compound represented by the formula (IV) or the compound (IV-1) and the pyrrole compound (2) are mixed first, and then the pyrrole compound (1) may be mixed.
  • the reaction temperature is preferably 30 ° C to 180 ° C, more preferably 80 ° C to 140 ° C.
  • the reaction time is preferably 1 hour to 20 hours, more preferably 3 hours to 15 hours.
  • the reaction is preferably performed in an organic solvent from the viewpoint of yield.
  • organic solvent include those exemplified above.
  • the amount of the organic solvent to be used is preferably 5 parts by mass or more and 200 parts by mass or less, more preferably 8 parts by mass or more and 160 parts by mass or less with respect to 1 part by mass of squaric acid.
  • the method for obtaining the target compound (I) from the reaction mixture is not particularly limited, and various known methods can be employed, and examples thereof include the above-described methods.
  • the pyrrole compound (V1) is obtained by reacting, for example, the following formula (V1 ′) (hereinafter sometimes referred to as “pyrrole compound (V1 ′)”) with a halogenating agent, And a compound represented by the following formula (III-1) (hereinafter sometimes referred to as “compound (III-1)”).
  • the pyrrole-based compound (V2) is obtained by reacting, for example, a compound represented by the following formula (V2 ′) (hereinafter, sometimes referred to as “pyrrole-based compound (V2 ′)”) with a halogenating agent.
  • the reaction product can be produced by reacting the reaction product with a compound represented by the following formula (III-2) (hereinafter, sometimes referred to as “compound (III-2)”).
  • compound (III-2) a compound represented by the following formula (III-2)
  • (V1 ′) and (V2 ′) have a protecting group such as an ethoxycarbonyl group at a position where they are not desired to react.
  • the desired pyrrole compound (V1) and the desired pyrrole compound (V2) can be produced by deprotection after the reaction.
  • R 1 to R 4 have the same meaning as described above.
  • T 1 and T 2 represent the same meaning as described above. ]
  • the monovalent hydrocarbon group having 1 to 6 carbon atoms which may have a substituent in R 1 to R 4 , T 1 and T 2 in the formulas (V1 ′) and (V2 ′) is as described above. Things.
  • Y 1 -Z 1 (III-1) Y 2 -Z 2 (III-2) In the formulas (III-1) and (III-2), Y 1 and Y 2 represent the same meaning as described above.
  • Z 1 and Z 2 each independently represent a halogen atom, a borate group, —B (OH) 2 , an alkylsulfonate group, or an arylsulfonate group. ]
  • a monovalent aromatic group which may have a substituent, a halogen atom, and a carbon which may have a substituent in Y 1 and Y 2 examples include those described above.
  • the halogen atom, borate ester group, alkylsulfonate group, or arylsulfonate group for Z 1 and Z 2 are as described above.
  • Examples of the pyrrole compound (V1 ′) and the pyrrole compound (V2 ′) include 2,4-dimethylpyrrole.
  • Examples of the compound (III-1) and the compound (III-2) include 4-hexylphenylboronic acid.
  • N-fluorosuccinimide N-chlorosuccinimide (NCS), N-bromosuccinimide (NBS), N-iodosuccinimide (NIS) represented as N-halogen succinimide (NXS), N-chlorophthalimide, N-chlorodiethylamine, N-chlorodibutylamine, N-chlorocyclohexylamine, chlorine, iodotrichloride, aluminum trichloride, tellurium (IV) chloride, molybdenum chloride, antimony chloride, iron (III) chloride , Titanium tetrachloride, phosphorus pentachloride, thionyl chloride, N-bromophthalimide, N-bromoditrifluoromethylamine, bromine, 1,2-dibromoethane, boron tribromide, copper bromide, silver bromide, bromide
  • a reaction product obtained by reacting the pyrrole compound (V1 ′) or the pyrrole compound (V2 ′) with a halogenating agent is preferably carried out in the presence of a palladium catalyst or in the presence of a nickel catalyst, and most preferably in the presence of a palladium catalyst.
  • a palladium catalyst and the nickel catalyst include those described above.
  • the substituent introduced into the reaction product by the halogenating agent is a halogen atom
  • Z 1 in compound (III-1) or Z 2 in compound (III-2) is each independently a borate ester group Alternatively, it is preferably -B (OH) 2 .
  • Z 1 and Z 2 are preferably each independently a halogen atom.
  • Z 1 and Z 2 Is preferably each independently an alkylsulfonate group or an arylsulfonate group.
  • the reaction between the pyrrole compound (V1 ′) or the pyrrole compound (V2 ′) and the halogenating agent is performed by reacting the halogenating agent with 1 mole of the pyrrole compound (V1 ′) or the pyrrole compound (V2 ′). It is preferably from 5 mol to 5 mol, more preferably from 1.05 mol to 3 mol.
  • the reaction temperature is preferably from -80 ° C to the boiling point of the solvent.
  • the reaction time is preferably 1 hour to 20 hours, more preferably 3 hours to 15 hours.
  • the reaction is preferably performed in an organic solvent from the viewpoint of yield.
  • the organic solvent include those exemplified above.
  • the amount of the organic solvent to be used is preferably 5 parts by mass or more and 100 parts by mass or less, more preferably 8 parts by mass or more and 50 parts by mass with respect to 1 part by mass of the pyrrole compound (V1 ′) or the pyrrole compound (V2 ′). It is more preferred that:
  • the method for obtaining the reaction product of the pyrrole compound (V1 ′) or the pyrrole compound (V2 ′) as the target compound from the reaction mixture and the halogenating agent is not particularly limited, and various known methods can be adopted. For example, the method described above can be used.
  • the amount of the compound (III-1) to be used is 1 to 1 mol of the pyrrole compound (V1 ′). It is preferably from 5 mol to 5 mol, and more preferably from 1.1 mol to 3 mol.
  • the amount of the compound (III-2) used is based on 1 mol of the pyrrole compound (V2'). It is preferably from 1 mol to 5 mol, more preferably from 1.1 mol to 3 mol.
  • the reaction temperature is preferably 30 ° C to 180 ° C, more preferably 80 ° C to 140 ° C.
  • the reaction time is preferably 1 hour to 20 hours, more preferably 3 hours to 15 hours.
  • the method for obtaining the target compound, pyrrole compound (V1) or pyrrole compound (V2), from the reaction mixture is not particularly limited, and various known methods can be employed, and examples thereof include the methods described above.
  • Compound (Ic) can be produced by halogenating the hydrogen atom represented by X 2b in the compound represented by the above formula (Ib) wherein X 2b is a hydrogen atom.
  • the halogenation can be performed, for example, using the above-mentioned halogenating agent.
  • the compound (II) is a compound of the formula (II) in which X 1 and X 2 are halogen atoms (hereinafter, may be referred to as “compound (IIc)”).
  • compound (IIc) halogen atoms
  • the squaric acid represented by the above formula (IV), the pyrrole-based compound (V1 ′), and the pyrrole-based compound (V2 ′) are allowed to react with each other, and represented by the following formula (II ′).
  • a compound (IIc) by reacting the compound (II ′) with a halogenating agent to obtain a compound (IIc).
  • R 1 to R 4 each independently represent a hydrogen atom or a monovalent hydrocarbon group having 1 to 6 carbon atoms which may have a substituent.
  • T 1 and T 2 each independently represent a hydrogen atom or a monovalent hydrocarbon group having 1 to 6 carbon atoms which may have a substituent.
  • the monovalent hydrocarbon group having 1 to 6 carbon atoms which may have a substituent in R 1 to R 4 , T 1 and T 2 includes those described above.
  • Examples of the halogenating agent include those described above.
  • Examples of the compound (II ′) include a compound represented by the following formula.
  • the amount of squaric acid used in the step of reacting squaric acid with the pyrrole compound (V1 ′) and the pyrrole compound (V2 ′) is 1 in total of the pyrrole compound (V1 ′) and the pyrrole compound (V2 ′). It is preferably from 0.45 mol to 0.6 mol, and more preferably from 0.47 mol to 0.51 mol, based on the mol.
  • the amount of the pyrrole compound (V2 ') to be used is preferably 1 mol or more and 1.5 mol or less based on 1 mol of the pyrrole compound (V1').
  • the reaction temperature is preferably 30 ° C to 180 ° C, more preferably 80 ° C to 140 ° C.
  • the reaction time is preferably 1 hour to 20 hours, more preferably 3 hours to 15 hours.
  • the reaction is preferably performed in an organic solvent from the viewpoint of yield.
  • organic solvent those exemplified above can be used.
  • the amount of the organic solvent to be used is preferably 5 parts by mass or more and 200 parts by mass or less, more preferably 8 parts by mass or more and 100 parts by mass or less with respect to a total of 1 part by mass of the pyrrole compound (V1 ′) and the pyrrole compound (V2 ′). More preferably, the amount is not more than part by mass.
  • the method for obtaining the target compound (II ') from the reaction mixture is not particularly limited, and various known methods can be employed, for example, the above-described methods can be used.
  • the halogenating agent is preferably used in an amount of 2 to 6 mol, preferably 2.2 to 5 mol, per 1 mol of compound (II ′). Preferably, there is.
  • the reaction temperature is preferably from -80 ° C to the boiling point of the solvent.
  • the reaction time is preferably 1 hour to 20 hours, more preferably 3 hours to 15 hours.
  • the reaction is preferably performed in an organic solvent from the viewpoint of yield.
  • organic solvent those exemplified above can be used.
  • the amount of the organic solvent to be used is preferably 5 parts by mass or more and 200 parts by mass or less, more preferably 10 parts by mass or more and 100 parts by mass or less with respect to 1 part by mass of compound (II ').
  • the method for obtaining the target compound (IIc) from the reaction mixture is not particularly limited, and various known methods can be employed, for example, the methods described above can be used.
  • Optical filter Compound (I) can be used, for example, for an optical filter of a display device or the like.
  • the optical filter is usually a layer formed from a composition containing a thermoplastic resin or a thermosetting resin having a light-transmitting property (preferably optically transparent), for example, a film-like material. It is.
  • the optical filter only needs to have a layer containing the compound (I) (hereinafter, sometimes referred to as “color correction layer”), and may be a color correction film having a single-layer structure of the color correction layer. Alternatively, a laminate having a multilayer structure including a color correction layer may be used.
  • the color filter may include one color correction layer, may include two or more color correction layers, and may include the compound (I) included in the two or more layers. They may be the same or different.
  • the color correction layer may be an adhesive layer, or may be a resin layer other than the adhesive layer (hereinafter, may be simply referred to as a “resin layer”).
  • the color correction layer is an adhesive layer
  • the two layers included in the optical filter may be bonded to each other, and the optical filter may be bonded to another member such as an image display device.
  • the adhesive layer can be an adhesive layer formed of an adhesive composition, an adhesive layer formed of an adhesive composition, or a layer formed of an adhesive composition and an adhesive composition.
  • the color correction film or the resin layer contains the compound (I).
  • the method used There is no particular limitation on the method used. For example, [i] a method of kneading with a resin for forming a color correction film or a resin layer and heat-forming the film, [ii] a resin for forming a color correction film or a resin layer or a monomer of the resin, and a compound (I) ) Is dispersed or dissolved in an organic solvent and formed into a film by a casting method or the like.
  • a coating solution obtained by dispersing or dissolving the compound (I) in a binder resin or an organic solvent on a resin base film may be used as the resin layer, and the resin base film may be peeled from the resin layer.
  • the resulting film may be used as a color correction film.
  • the thickness of the color correction film or the resin layer is not particularly limited, but may be, for example, 1 ⁇ m to 200 ⁇ m.
  • the content is not particularly limited.
  • the compound (I) can be used in an amount of at least 0.001 part by mass, preferably at least 0.02 part by mass, based on 100 parts by mass of the base polymer forming the color correction film or the resin layer. It is more preferably at least 05 parts by mass, and can be at most 10 parts by mass, preferably at most 3 parts by mass, more preferably at most 0.5 part by mass.
  • the method for incorporating the compound (I) into the adhesive layer is not particularly limited, and when preparing the adhesive composition or the pressure-sensitive adhesive composition forming the adhesive layer, the compound (I) I) may be added.
  • the thickness of the adhesive layer is not particularly limited, but may be, for example, 1 ⁇ m to 100 ⁇ m.
  • the content is not particularly limited.
  • the compound (I) can be used in an amount of 0.01 part by mass or more based on 100 parts by mass of the base polymer constituting the adhesive composition and / or the pressure-sensitive adhesive composition contained in the adhesive layer, and 0.02 parts by mass. Is preferably at least 0.05 part by mass, and more preferably at most 10 parts by mass, and preferably at most 5 parts by mass, more preferably at most 0.5 part by mass. More preferably, there is.
  • the optical filter can be used for a display device such as an organic electroluminescence (organic EL) display device or a liquid crystal display device, and can be used by being bonded to the viewing side of an image display element of the display device.
  • the optical filter preferably has an adhesive layer and a resin layer other than the adhesive layer, and at least one of the adhesive layer and the resin layer is preferably a color correction layer containing the compound (I).
  • the laminate structure is not particularly limited, and may have, for example, the laminate structure shown in FIGS. 1 (a) and 1 (b).
  • 1A and 1B are schematic cross-sectional views illustrating an example of an optical filter.
  • the optical filter 10 shown in FIG. 1A can be used for an organic EL display device.
  • the optical filter 10 can include, for example, an adhesive layer 11 for an image display element, a retardation film 12, an adhesive layer 13, a first protective film 14, a polarizing film 15, and a second protective film 16 in this order.
  • Each of the pressure-sensitive adhesive layer 11 and the pressure-sensitive adhesive layer 13 for an image display element corresponds to the above-described adhesive layer, and the retardation film 12, the first protective film 14, the polarizing film 15, and the second protective film 16 are all This corresponds to the resin layer described above.
  • the first protective film 14, the polarizing film 15, and the second protective film 16 in the optical filter 10 form a polarizing plate, and the first protective film 14 and the second protective film 16 are bonded to the polarizing film 15. May have an adhesive layer.
  • the pressure-sensitive adhesive layer 11 for an image display element is used for bonding to a light emitting layer including an organic EL element which is an image display element of an organic EL display device.
  • a separator (release film) may be provided on the surface of the image display element pressure-sensitive adhesive layer 11 opposite to the retardation film 12.
  • the optical filter 20 shown in FIG. 1B can be used for a liquid crystal display device.
  • the optical filter 20 can include, for example, an adhesive layer 21 for an image display element, a first protective film 24, a polarizing film 25, and a second protective film 26 in this order.
  • the pressure-sensitive adhesive layer 21 for an image display element corresponds to the above-described adhesive layer
  • the first protective film 24, the polarizing film 25, and the second protective film 26 all correspond to the above-described resin layer.
  • the first protective film 24, the polarizing film 25, and the second protective film 26 in the optical filter 20 form a polarizing plate, and the first protective film 24 and the second protective film 26 are bonded to the polarizing film 25.
  • the pressure-sensitive adhesive layer 21 for an image display element is used for bonding to a liquid crystal cell which is an image display element of a liquid crystal display device.
  • a separator (release film) (not shown) may be provided on the surface of the image display element pressure-sensitive adhesive layer 21 opposite to the first protective film 24.
  • the compound (I) can be contained in at least one of the resin layer and the adhesive layer constituting the optical filters 10 and 20 shown in FIGS. 1A and 1B.
  • the optical filter 10 shown in FIG. 1A for example, one or more of the pressure-sensitive adhesive layer 11 for an image display element, the pressure-sensitive adhesive layer 13, the first protective film 14, and the second protective film 15 are provided with the compound ( I).
  • the optical filter 20 shown in FIG. 1B for example, one or more of the pressure-sensitive adhesive layer 21 for an image display element, the first protective film 24, and the second protective film 25 may contain the compound (I). it can.
  • the optical filters 10 and 20 shown in FIGS. 1A and 1B are merely examples, and may have a laminated structure other than the above.
  • the second protective films 16 and 26 may have further layers such as a film with an anti-glare function and a film with a surface anti-reflection function on the surface opposite to the polarizing films 15 and 25.
  • the first protective films 15 and 25 may have a function as a retardation film
  • the second protective films 16 and 26 may have a function as an antiglare function, a surface antireflection function, a function as a retardation film, and the like. May be provided.
  • a color correction layer containing the compound (I) may be provided at an arbitrary position separately from the layers constituting the optical filters 10 and 20 shown in FIGS. 1 (a) and 1 (b).
  • the optical filter contains the compound (I), it can absorb light near 580 nm (575 to 590 nm) (preferably light having a maximum absorption wavelength of 580 nm).
  • light having an absorption wavelength in a wavelength range around 580 nm (575 to 590 nm) is absorbed from light incident on the optical filter.
  • the light transmitted through the optical filter can improve the color purity of the green light and the red light as compared with the light incident on the optical filter.
  • Adhesive layer examples of the adhesive composition that can be used for the adhesive layer include a water-based adhesive, an active energy ray-curable adhesive, and a combination thereof.
  • the water-based adhesive examples include a polyvinyl alcohol-based resin aqueous solution, a water-based two-part urethane-based emulsion adhesive, and the like.
  • Active energy ray-curable adhesives are adhesives that are cured by irradiating active energy rays such as ultraviolet rays, for example, those containing a polymerizable compound and a photopolymerizable initiator, those containing a photoreactive resin, Examples include those containing a binder resin and a photoreactive crosslinking agent.
  • the polymerizable compound include photopolymerizable monomers such as photocurable epoxy monomers, photocurable (meth) acrylic monomers, and photocurable urethane monomers, and oligomers derived from these monomers.
  • photopolymerization initiator examples include those containing a substance that generates active species such as neutral radicals, anion radicals, and cation radicals upon irradiation with active energy rays such as ultraviolet rays.
  • active species such as neutral radicals, anion radicals, and cation radicals upon irradiation with active energy rays such as ultraviolet rays.
  • (meth) acrylic means “at least one of acrylic and methacrylic”.
  • the pressure-sensitive adhesive composition that can be used for the adhesive layer a conventionally known pressure-sensitive adhesive composition can be used.
  • the adhesive composition include (meth) acrylic adhesives, urethane-based adhesives, silicone-based adhesives, polyester-based adhesives, polyamide-based adhesives, polyether-based adhesives, fluorine-based adhesives, and rubber-based adhesives.
  • An adhesive and the like can be mentioned.
  • an energy ray-curable pressure-sensitive adhesive, a thermosetting pressure-sensitive adhesive, or the like may be used.
  • a (meth) acrylic pressure-sensitive adhesive is preferably used from the viewpoint of transparency, adhesive strength, reliability and the like.
  • the acrylic pressure-sensitive adhesive is not particularly limited, but is a polymer having (meth) acrylic acid ester as a main component (containing 50% by mass or more), and one kind of (meth) acrylic acid ester It may be a homopolymer or a copolymer of (meth) acrylate and another (meth) acrylate.
  • the (meth) acrylate include butyl (meth) acrylate, ethyl (meth) acrylate, methyl (meth) acrylate, isooctyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, and (meth) acrylic acid. 2-phenoxyethyl acid.
  • a polar monomer may be copolymerized in these polymers mainly composed of (meth) acrylic acid esters.
  • the polar monomer include (meth) acrylic acid, 2-hydroxypropyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, (meth) acrylamide, and 2- (N, N-dimethylamino) ethyl ( Monomers having a polar functional group such as a carboxy group, a hydroxyl group, an amide group, an amino group, and an epoxy group, such as meth) acrylate and glycidyl (meth) acrylate.
  • a resin having a weight average molecular weight (Mw) of 100,000 or more can be used, preferably 600,000 or more, and usually 2.5 million or less.
  • acrylic pressure-sensitive adhesives can be used alone, but are usually used in combination with a crosslinking agent.
  • the crosslinking agent include divalent or polyvalent metal ions that form a metal carboxylate with a carboxy group, amine compounds that form an amide bond with a carboxy group, Examples include epoxy compounds and diol compounds which form an ester bond with a carboxy group, and isocyanate compounds which form an amide bond with a carboxy group. Among them, isocyanate compounds are preferably used.
  • isocyanate compounds xylylene diisocyanate, tolylene diisocyanate or hexamethylene diisocyanate; an adduct obtained by reacting a polyol such as glycerol or trimethylolpropane with these isocyanate compounds; dimer or trimer of these isocyanate compounds Or a mixture thereof; a mixture of two or more of the above-mentioned isocyanate compounds is preferably used.
  • Preferred isocyanate-based compounds include tolylene diisocyanate, adducts obtained by reacting polyol with tolylene diisocyanate, dimers of tolylene diisocyanate, and trimers of tolylene diisocyanate, and hexamethylene diisocyanate and hexamethylene diisocyanate.
  • An adduct obtained by reacting a polyol, a dimer of hexamethylene diisocyanate, and a trimer of hexamethylene diisocyanate are exemplified.
  • the content of the crosslinking agent in the acrylic pressure-sensitive adhesive is generally 0 parts by mass or more and 5 parts by mass or less, preferably 0.05 parts by mass or more and 2 parts by mass or less with respect to 100 parts by mass of the (meth) acrylic resin. .
  • the acrylic pressure-sensitive adhesive may further contain a silane compound.
  • the acrylic pressure-sensitive adhesive contains a silane compound, the adhesiveness between the obtained pressure-sensitive adhesive layer and an optical member such as a glass substrate can be enhanced.
  • silane compound examples include vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris (2-methoxyethoxy) silane, 3-aminopropyltriethoxysilane, 3-glycidoxypropyltrimethoxysilane, and 3-glycidoxypropyl Methyldimethoxysilane, 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane, 3-methacryloyloxypropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-gly Sidoxypropyltriethoxysilane, 3-glycidoxypropyldimethoxymethylsilane, 3-glycidoxypropylethoxydimethylsilane and the like can be mentioned. Two or more silane compounds may be used.
  • the silane compound may be of a silicone oligomer type.
  • silicone oligomer is shown in the form of a (monomer) oligomer, for example, 3-mercaptopropyltrimethoxysilane-tetramethoxysilane copolymer, mercaptomethyltrimethoxysilane-tetramethoxysilane copolymer, 3-glycidoxypropyltrimethoxysilane -Tetramethoxysilane copolymer, 3-methacryloyloxypropyltrimethoxysilane-tetramethoxysilane copolymer, 3-acryloyloxypropyltrimethoxysilane-tetramethoxysilane copolymer, vinyltrimethoxysilane-tetramethoxysilane copolymer and the like.
  • the content of the silane compound in the acrylic pressure-sensitive adhesive is usually 0.01 to 10 parts by mass, preferably 0.05 to 5 parts by mass, based on 100 parts by mass of the (meth) acrylic resin. It is more preferably at least 0.1 part by mass and at most 2 parts by mass.
  • the content of the silane compound is 0.01 parts by mass or more, the effect of improving the adhesion between the pressure-sensitive adhesive layer and an optical member such as a glass substrate is easily obtained.
  • the content of the silane compound is 10 parts by mass or less, bleed out of the silane compound from the pressure-sensitive adhesive layer can be suppressed.
  • the acrylic pressure-sensitive adhesive may further contain an ionic compound as an antistatic agent for imparting antistatic properties.
  • the ionic compound is a compound having an inorganic cation or an organic cation and an inorganic anion or an organic anion.
  • the acrylic pressure-sensitive adhesive may contain two or more ionic compounds.
  • Examples of the inorganic cation include alkali metal ions such as lithium cation [Li + ], sodium cation [Na + ], potassium cation [K + ], beryllium cation [Be 2+ ], magnesium cation [Mg 2+ ], and calcium cation. And alkaline earth metal ions such as [Ca 2+ ].
  • Examples of the organic cation include an imidazolium cation, a pyridinium cation, a pyrrolidinium cation, an ammonium cation, a sulfonium cation, and a phosphonium cation.
  • inorganic anion examples include a chloride anion [Cl ⁇ ], a bromide anion [Br ⁇ ], an iodide anion [I ⁇ ], a tetrachloroaluminate anion [AlCl 4 ⁇ ], a 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] ⁇ ], Hexafluoroantimonate anion [SbF 6 ⁇ ], hexafluoroniobate anion [NbF 6 ⁇ ], hexafluorotantalate anion [TaF 6 ⁇ ], dicyanamide anion [(CN)
  • organic anion examples include an acetate anion [CH 3 COO ⁇ ], a trifluoroacetate anion [CF 3 COO ⁇ ], a methanesulfonate anion [CH 3 SO 3 ⁇ ], a trifluoromethanesulfonate anion [CF 3 SO 3 ⁇ ], p-toluenesulfonate anion [p-CH 3 C 6 H 4 SO 3 ⁇ ], bis (fluorosulfonyl) imide anion [(FSO 2 ) 2 N ⁇ ], bis (trifluoromethanesulfonyl) imide anion [(CF 3 SO 2 ) 2 N ⁇ ], tris (trifluoromethanesulfonyl) methanide anion [(CF 3 SO 2 ) 3 C ⁇ ], dimethylphosphinate anion [(CH 3 ) 2 POO ⁇ ], (poly) hydrofluorofluoride anion [ F (HF) n ⁇
  • ionic compound can be selected from combinations of the above-mentioned cation component and anion component.
  • Examples of the ionic compound having an organic cation include N-octylpyridinium hexafluorophosphate, N-octyl-4-methylpyridinium hexafluorophosphate, N-butyl-4-methylpyridinium hexafluorophosphate, N-decylpyridinium bis ( Pyridinium salts such as fluorosulfonyl) imide, N-hexylpyridinium bis (trifluoromethanesulfonyl) imide, N-octylpyridinium bis (trifluoromethanesulfonyl) imide, 1-ethyl-3-methylimidazolium hexafluorophosphate, 1-ethyl- 3-methylimidazolium ⁇ p-toluenesulfonate, 1-ethyl-3-methylimidazolium ⁇ bis (fluorosulfonyl) imide, ⁇ 1-e
  • Examples of the ionic compound having an inorganic cation include lithium bromide, lithium iodide, sodium hexafluorophosphate, and the like.
  • the ionic compound is preferably solid at room temperature from the viewpoint of maintaining antistatic performance.
  • the ionic compound preferably has a melting point of 30 ° C. or more, more preferably 35 ° C. or more.
  • the melting point of the ionic compound is preferably 90 ° C. or lower, more preferably 70 ° C. or lower, and further preferably 50 ° C. or lower. It is below ° C.
  • the content of the ionic compound in the acrylic pressure-sensitive adhesive is preferably 0.1 to 8 parts by mass, more preferably 0.2 to 6 parts by mass, based on 100 parts by mass of the (meth) acrylic resin. Or less, more preferably 0.5 to 5 parts by mass, particularly preferably 1 to 5 parts by mass.
  • the content of the ionic compound is 0.1 parts by mass or more, it is advantageous for improving antistatic performance, and when it is 8 parts by mass or less, it is advantageous for maintaining the durability of the pressure-sensitive adhesive layer.
  • the adhesive composition and the pressure-sensitive adhesive composition may further contain various additives.
  • the additives include a reworking agent, a tackifying resin, an antioxidant, an ultraviolet absorber, an antifoaming agent, a corrosive, and a light diffusing agent such as fine particles.
  • the resin layer As the resin layer, a polarizing film; a protective film provided to protect the surface of the polarizing film or the like; a retardation film; an optical compensation film other than the retardation film; A film having an anti-reflection function; a reflection film having a reflection function on the surface; a transflective film having both a reflection function and a transmission function; a light diffusion film; a hard coat film;
  • the optical filter may include one or more resin layers described above.
  • the polarizing film examples include a film in which iodine is oriented in a polyvinyl alcohol-based resin layer, a film in which a liquid crystal compound and a dichroic dye are oriented, and the like.
  • the material when the resin layer is other than the polarizing film is not particularly limited, and examples thereof include chain polyolefin resins (polyethylene resins, polypropylene resins, etc.) and cyclic polyolefin resins (norbornene resins, etc.).
  • Polyolefin resins such as triacetyl cellulose, diacetyl cellulose and cellulose acetate propionate; polyester resins such as polyethylene terephthalate and polyethylene naphthalate; polycarbonate resins; (meth) acrylic acid, poly (meth) acrylic (Meth) acrylic resins such as methyl acid; vinyl alcohol resins such as polyvinyl alcohol and polyvinyl acetate; polystyrene resins; mixtures thereof, copolymers and the like.
  • These resins may contain one or more additives such as lubricants, plasticizers, dispersants, heat stabilizers, ultraviolet absorbers, infrared absorbers, antistatic agents, antioxidants, and light diffusing agents such as fine particles. It may be contained.
  • the above-described optical filter can be suitably used for display devices such as an organic EL display device, a liquid crystal display device, an inorganic electroluminescence (inorganic EL) display device, and an electron emission display device.
  • display devices such as an organic EL display device, a liquid crystal display device, an inorganic electroluminescence (inorganic EL) display device, and an electron emission display device.
  • the optical filter By arranging the optical filter on the viewing side relative to the image display element of the display device, of the light incident on the optical filter, light having a wavelength of about 580 nm (575 to 590 nm) (preferably light having a maximum absorption wavelength of 580 nm) Can be absorbed. Accordingly, the light transmitted through the optical filter has higher color purity of the green light and the red light as compared with the case where the light does not transmit through the optical filter, so that the color gamut that can be expressed in the display device can be expanded. . In a conventional display device not using the optical filter, the separation between green
  • FIGS. 2A and 2B are schematic cross-sectional views illustrating an example of a display device including an optical filter.
  • the display device illustrated in FIG. 2A is an organic EL display device including the optical filter 10 illustrated in FIG. 1A and the image display device 1 that is a light emitting layer including the organic EL device.
  • the optical filter 10 can be arranged on the viewing side of the image display element 1 via the adhesive layer 11 for the image display element.
  • the display device shown in FIG. 2B is a liquid crystal display device including the optical filter 20 shown in FIG. 1B and the image display element 2 which is a liquid crystal cell including a liquid crystal layer.
  • the optical filter 20 can be disposed on the viewing side of the image display element 2 via the adhesive layer 21 for the image display element.
  • Example 1 (compound represented by formula (II))] 3.0 parts of 3,4-dihydroxy-3-cyclobutene-1,2-dione (manufactured by Fuji Film Wako Pure Chemical Industries, Ltd.) and 5.0 parts of 2,4-dimethylpyrrole (manufactured by Tokyo Chemical Industry Co., Ltd.) 175 parts of 1-butanol and 290 parts of toluene were mixed. The resulting mixture was stirred at a temperature of 110 ° C. for 3 hours while removing generated water using a Dean-Stark tube. After completion of the reaction, the solvent was distilled off, 300 parts of ion-exchanged water was added, and the precipitated solid was collected by filtration. The solid collected by filtration was washed with methanol / ion exchanged water. The obtained solid was dried under reduced pressure at a temperature of 60 ° C. for 12 hours to obtain 4.0 parts of a compound represented by the formula (A-1).
  • Example 2 (compound represented by formula (I)) 0.85 part of the compound represented by the formula (A-2) obtained in Example 1, 89 parts of tetrahydrofuran and 70 parts of ion-exchanged water were mixed. 6 parts of a 1 mol / L cesium carbonate aqueous solution, 0.37 parts of tris (dibenzylideneacetone) -dipalladium (0), 0.46 parts of tri-tert-butylphosphonium tetrafluoroborate, 2,6-dimethyl-4- ( 1.49 parts of 4,4,5,5-tetramethyl-1,3,2-dioxaboran-2-yl) phenol (manufactured by Tokyo Chemical Industry Co., Ltd.) was added, and the mixture was refluxed for 2 hours.
  • Example 3 (compound represented by formula (I))
  • 2,6-dimethyl-4- (4,4,5,5-tetramethyl-1,3,2-dioxaboran-2-yl) phenol in Example 2 3,4,5-trimethoxyphenyl Synthesis was performed in the same manner as in Example 2 except that boronic acid was used, to obtain a compound represented by the formula (A-4).
  • boronic acid was used, to obtain a compound represented by the formula (A-4).
  • the maximum absorption wavelength was measured. Table 1 shows the measured maximum absorption wavelengths.
  • Example 6 (compound represented by formula (I))
  • A-7 4- (dimethylamino) phenylboronic acid
  • Table 1 shows the measured maximum absorption wavelengths.
  • Example 7 (compound represented by formula (I))
  • 4- (diphenylamino) phenylboronic acid Compound (A-8) was synthesized in the same manner as in Example 2 except that was used to obtain a compound represented by the formula (A-8).
  • Table 1 shows the measured maximum absorption wavelengths.
  • Example 9 (compound represented by formula (I))
  • 6-ethoxy-2-naphthaleneboronic acid Compound (A-10) was synthesized in the same manner as in Example 2 except that was used to obtain a compound represented by the formula (A-10).
  • Table 1 shows the measured maximum absorption wavelengths.
  • Example 10 (compound represented by formula (I))
  • Example 2 instead of 2,6-dimethyl-4- (4,4,5,5-tetramethyl-1,3,2-dioxaboran-2-yl) phenol in Example 2, 9,9-dimethylfluorene-2-yl
  • the compound was synthesized in the same manner as in Example 2 except that boronic acid was used, to obtain a compound represented by the formula (A-11).
  • the maximum absorption wavelength was measured.
  • Table 1 shows the measured maximum absorption wavelengths.
  • Example 11 (compound represented by formula (I))
  • benzo [b] thiophen-2-boron Synthesis was performed in the same manner as in Example 2 except that an acid was used to obtain a compound represented by the formula (A-12).
  • the maximum absorption wavelength was measured. Table 1 shows the measured maximum absorption wavelengths.
  • Example 13 (compound represented by formula (I))
  • 9- (4-biphenylyl) carbazole- Synthesis was performed in the same manner as in Example 2 except that 3-boronic acid pinacol was used to obtain a compound represented by the formula (A-14).
  • the maximum absorption wavelength was measured. Table 1 shows the measured maximum absorption wavelengths.
  • Example 14 (compound represented by formula (I))
  • Example 15 (compound represented by formula (I))
  • Example 2 4-methoxy-3,5-dimethyl Synthesis was performed in the same manner as in Example 2 except that phenylboronic acid was used to obtain a compound represented by the formula (A-16).
  • phenylboronic acid was used to obtain a compound represented by the formula (A-16).
  • Table 1 shows the measured maximum absorption wavelengths.
  • Example 16 (compound represented by formula (I))
  • Example 19 (compound represented by formula (II))] 11.89 parts of 3,4-dibutoxy-3-cyclobutene-1,2-dione (manufactured by Tokyo Chemical Industry Co., Ltd.) and 38.9 parts of 1-butanol were mixed and heated and stirred at 110 ° C. To the obtained mixture, 5.0 parts of 2,4-dimethylpyrrole (manufactured by Tokyo Chemical Industry Co., Ltd.) was added dropwise over 10 minutes, and the mixture was heated under reflux for 3 hours. The obtained mixture was cooled to room temperature, and the precipitated crystals were filtered to separate the solution from the crystals.
  • Example 20 (compound represented by formula (I))] 0.195 parts of the compound represented by the formula (A-20), 22.2 parts of tetrahydrofuran, and 17.5 parts of pure water were added to a four-necked flask, and nitrogen gas was introduced at 80 ° C. for 60 minutes to perform bubbling. went. 0.092 parts of tris (dibenzylideneacetone) palladium, 0.116 parts of [tri (tertiarybutyl) phosphonium] tetrafluoroborate and 1.5 parts of a 1 mol / L cesium carbonate aqueous solution were added to the obtained mixture. .
  • the reaction solution was obtained by dissolving 0.243 parts of benzofuran-2-boronic acid (manufactured by Tokyo Chemical Industry Co., Ltd.) in 6.66 parts of tetrahydrofuran while stirring the reaction solution at an oil bath temperature of 80 ° C. The solution was added dropwise over 10 minutes and stirred for 2 hours. To the obtained mixture, 100 parts of a 10% by mass acetic acid aqueous solution was added, and the mixture was stirred under a nitrogen atmosphere for 15 minutes. To the obtained mixture, 0.3 parts of 10% saline was added, and a liquid separation operation was performed to separate an organic layer. The organic layer was dried using an evaporator to obtain a tar-like crude product 1.
  • a crosslinking agent (“Coronate HXR” (isocyanurate-modified hexamethylene diisocyanate) obtained from Tosoh Corporation) was used for 100 parts of the solid content of the (meth) acrylic resin obtained in the production of the (meth) acrylic resin. ), 0.5 part of a silane compound (“KBM-403" (3-glycidoxypropyltrimethoxysilane) obtained from Shin-Etsu Chemical Co., Ltd.), and N-hexyl-4 as an antistatic agent.
  • KBM-403 3-glycidoxypropyltrimethoxysilane
  • the pressure-sensitive adhesive composition 1 is applied to a release-treated surface of a first separator film ("PLR-382190" obtained from Lintec Co., Ltd.) made of a polyethylene terephthalate film subjected to a release treatment using an applicator. Then, it was dried at 100 ° C. for 1 minute to prepare an adhesive layer. The thickness of the obtained pressure-sensitive adhesive layer was 20 ⁇ m.
  • a release-treated surface of a second separator film (“PLR-251130" obtained from Lintec Co., Ltd.) made of a release-treated polyethylene terephthalate film was bonded. Sheet 1 was obtained.
  • One of the separator films of the obtained pressure-sensitive adhesive sheet 1 was peeled off, bonded to one surface of non-alkali glass (EagleXG manufactured by Corning Incorporated), and using an ultraviolet-visible spectrophotometer (UV-2450 manufactured by Shimadzu Corporation). The maximum absorption wavelength was measured. Table 2 shows the results. The absorbance of the above-mentioned separator film and alkali-free glass at a wavelength of 400 nm to 700 nm is almost 0.
  • Pressure-sensitive adhesive composition 2 was prepared in the same manner as in preparation of pressure-sensitive adhesive composition 1, except that the compound represented by formula (A-6) was used instead of the compound represented by formula (A-5).
  • a pressure-sensitive adhesive sheet 2 was prepared in the same manner as in the preparation of the pressure-sensitive adhesive sheet 1 except that the obtained pressure-sensitive adhesive composition 2 was used, and the maximum absorption wavelength was measured. Table 2 shows the results.
  • Pressure-sensitive adhesive compositions 5 to 11 were prepared in the same manner as in the preparation of pressure-sensitive adhesive composition 1, except that the compounds shown in Table 2 were used instead of the compound represented by the formula (A-5).
  • the pressure-sensitive adhesive sheets 5 to 11 were prepared in the same manner as in the preparation of the pressure-sensitive adhesive sheet 1 except that the obtained pressure-sensitive adhesive compositions 5 to 11 were used, and the maximum absorption wavelength was measured. Table 2 shows the results.
  • Pressure-sensitive adhesive composition 3 was prepared in the same manner as in the preparation of pressure-sensitive adhesive composition 1, except that the compound represented by formula (B-1) was used instead of the compound represented by formula (A-5).
  • a pressure-sensitive adhesive sheet 3 was prepared in the same manner as in the preparation of the pressure-sensitive adhesive sheet 1 except that the obtained pressure-sensitive adhesive composition 3 was used, and the maximum absorption wavelength was measured. Table 2 shows the results.
  • Pressure-sensitive adhesive composition 4 was prepared in the same manner as in the preparation of pressure-sensitive adhesive composition 1, except that the compound represented by formula (A-1) was used instead of the compound represented by formula (A-5).
  • the pressure-sensitive adhesive sheet 4 was prepared in the same manner as in the preparation of the pressure-sensitive adhesive sheet 1 except that the obtained pressure-sensitive adhesive composition 4 was used, and the maximum absorption wavelength was measured. Table 2 shows the results.
  • Pressure-sensitive adhesive composition 14 was prepared in the same manner as in the preparation of pressure-sensitive adhesive composition 1, except that the compound represented by the formula (A-5) was not used.
  • the pressure-sensitive adhesive sheet 14 was produced in the same manner as in the production of the pressure-sensitive adhesive sheet 1 except that the obtained pressure-sensitive adhesive composition 14 was used.
  • an optical filter having a maximum absorption wavelength in a wavelength range around 580 nm (wavelength 575 to 590 nm) can be prepared.
  • the pressure-sensitive adhesive sheet (optical filter) containing the compound (I) to a display device, the separation between green light and red light in transmitted light can be improved, and thus, reproducibility can be improved.
  • the gamut range could be expanded.
  • a decrease in the transmittance of the backlight could be suppressed.
  • Photocurable adhesive liquid 2 was prepared by performing the same preparation as photocurable adhesive liquid 1 except that the compound represented by formula (A-18) was added instead of the compound represented by formula (A-16). did.
  • a surface of a 60 ⁇ m-thick triacetylcellulose film (trade name “Fujitac TG60UL”, manufactured by Fuji Film Co., Ltd.) containing an ultraviolet absorber is subjected to corona discharge treatment, and the corona discharge treated surface is subjected to the photocuring prepared above.
  • the adhesive liquid 1 was applied using a bar coater so that the film thickness after curing was about 2 ⁇ m.
  • a 28 ⁇ m thick polyvinyl alcohol-iodine polarizer was bonded to the adhesive layer formed by this coating.
  • a corona discharge treatment is applied to the surface of a 50 ⁇ m-thick retardation film (trade name “ZEONOR”, manufactured by Zeon Corporation) made of a cyclic polyolefin resin, and the photocurable adhesive is applied to the corona discharge treatment surface.
  • Liquid 1 was applied using a bar coater so that the film thickness after curing was about 2 ⁇ m.
  • the polarizer side of the polarizer having the above-prepared triacetylcellulose film bonded on one side was bonded to the adhesive layer formed by this coating to prepare a laminate.
  • a polarizing plate 2 having a protective film attached to both surfaces of a polarizer was prepared in the same manner as in the production of the polarizing plate 1 except that the photocurable adhesive solution 2 was used instead of the photocurable adhesive solution 1. Produced. The obtained polarizing plate was cut into 40 mm ⁇ 40 mm, and the maximum absorption wavelength was obtained by using the same method as that for the polarizing plate 1. Table 4 shows the results.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Electroluminescent Light Sources (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Optical Filters (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pyrrole Compounds (AREA)
PCT/JP2019/028047 2018-07-23 2019-07-17 化合物及びその製造方法 WO2020022134A1 (ja)

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JP2001183522A (ja) * 1999-12-27 2001-07-06 Mitsubishi Chemicals Corp プラズマディスプレイパネル用フィルター
JP2005520835A (ja) * 2002-03-19 2005-07-14 バイエル ケミカルズ アクチエンゲゼルシャフト 光データキャリアの情報層における吸光性化合物としてのスクアリリウム色素
JP2017203902A (ja) * 2016-05-12 2017-11-16 ソニー株式会社 スクアリリウム化合物および固体撮像素子ならびに電子機器

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WO2005034066A1 (ja) * 2003-09-30 2005-04-14 Mitsubishi Chemical Corporation 電子ディスプレイ用フィルタ及び電子ディスプレイ装置
WO2008069268A1 (ja) * 2006-12-07 2008-06-12 Konica Minolta Holdings, Inc. 光学フィルター用組成物、その製造方法、光学フィルター及びディスプレイ用前面フィルター
TW201348226A (zh) * 2012-02-28 2013-12-01 Amgen Inc 作為ｐｉｍ抑制劑之醯胺
JP2017141215A (ja) * 2016-02-08 2017-08-17 国立大学法人愛媛大学 新規オキソカーボン系化合物
CN108178720B (zh) * 2018-02-13 2021-04-13 山东盛华新材料科技股份有限公司 一种4-环丁基联苯含氟化合物的合成方法

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JP2001183522A (ja) * 1999-12-27 2001-07-06 Mitsubishi Chemicals Corp プラズマディスプレイパネル用フィルター
JP2005520835A (ja) * 2002-03-19 2005-07-14 バイエル ケミカルズ アクチエンゲゼルシャフト 光データキャリアの情報層における吸光性化合物としてのスクアリリウム色素
JP2017203902A (ja) * 2016-05-12 2017-11-16 ソニー株式会社 スクアリリウム化合物および固体撮像素子ならびに電子機器

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