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WO2017034370A1 - Composé à base de pérylène, procédé de préparation associé, et colorant fluorescent le comprenant - Google Patents

Composé à base de pérylène, procédé de préparation associé, et colorant fluorescent le comprenant Download PDF

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Publication number
WO2017034370A1
WO2017034370A1 PCT/KR2016/009517 KR2016009517W WO2017034370A1 WO 2017034370 A1 WO2017034370 A1 WO 2017034370A1 KR 2016009517 W KR2016009517 W KR 2016009517W WO 2017034370 A1 WO2017034370 A1 WO 2017034370A1
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group
substituted
compound
ring
perylene
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Korean (ko)
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이윤이
현동균
정재훈
신상식
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Ukseung Chemical Co Ltd
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Ukseung Chemical Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
    • C07C15/20—Polycyclic condensed hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
    • C07C15/40—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals
    • C07C15/56—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals polycyclic condensed
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B3/00—Dyes with an anthracene nucleus condensed with one or more carbocyclic rings
    • C09B3/14—Perylene derivatives

Definitions

  • the present application relates to a novel perylene-based compound, a preparation method thereof, and a fluorescent dye including the same.
  • Perylene-based compounds are used as liquid phase fluorescent dyes as polycyclic aromatic hydrocarbon compounds, and are particularly well known as excellent photosafety pigments and bat dyes. Pigments and dyes containing perylene-based compounds show long-wavelength luminescence due to extended resonance, and are used in various fields with very strong fluorescence, and recently, their use as chemiluminescent materials in the display field has greatly increased. Patent Publication No. US2011 / 0251393).
  • the present application is to provide a novel perylene-based compound, a preparation method thereof and a fluorescent dye comprising the same.
  • a first aspect of the present application provides a perylene-based compound represented by Formula 1 below:
  • R 1 and said R 2 are, each independently, hydrogen, halogen, cyano, C 1-20 alkyl group which may be substituted with a linear or branched, optionally substituted C 3-30 cycloalkyl Alkyl group, C 6-30 aryl group which may be substituted, C 1-20 alkylamine group which may be substituted, C 3-30 cycloalkylamine group which may be substituted, C 6- which may be substituted 30 arylamine group, a linear or branched C 1-20 alkoxy group which may be substituted, a C 3-30 cycloalkoxy group which may be substituted, a C 6-30 aryloxy group which may be substituted, a linear which may be substituted Or a branched C 2-10 alkylcarboxyl group, a substituted C 6-30 arylcarboxyl group, or a substituted C 6-30 arylmercapto group, wherein R 3 and R 4 are each independently hydrogen , Halogen group, cyan
  • a compound represented by the following Chemical Formula 2 may be substituted with a linear or branched C 1-20 alkane compound, a C 3-30 cycloalkane compound which may be substituted, and C 6 which may be substituted.
  • -30 aryl compounds, substitutable C 6-30 phenolic compounds, substitutable linear or branched C 1-20 alcohol compounds, substitutable linear or branched C 1-20 alkylamine compounds Preparation of the perylene-based compound according to claim 1 comprising reacting with a C 3-30 cycloalkylamine compound which may be substituted, a C 6-30 arylamine compound which may be substituted, or N-halosuccinimide.
  • R 5 to R 8 are each independently hydrogen, halogen or a linear or branched C 2-10 alkylcarboxyl group which may be substituted.
  • the third aspect of the present application provides a fluorescent dye comprising a perylene-based compound according to the present application.
  • the perylene-based compound of the present application is a novel compound which can be used as a green fluorescent dye having a perylene-based nucleus structure and exhibits excellent solubility, in particular, excellent solubility, durability, thermal stability, and luminescence properties in an organic solvent.
  • 1 is a spectrum showing the UV / PL results of the perylene compound according to an embodiment of the present application.
  • the term "combination of these" included in the expression of the makushi form means one or more mixtures or combinations selected from the group consisting of constituents described in the expression of the makushi form, wherein the constituents It means to include one or more selected from the group consisting of.
  • alkyl refers to a linear or branched, C 1 -C 20 alkyl, C 1 -C 15 alkyl, C 1 -C 10 alkyl, or It may include C 1 -C 6 alkyl, including, for example, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl or all possible isomers thereof It may be, but may not be limited thereto.
  • cycloalkyl alone or in combination with other substituents, may include C 3-30 cycloalkyl, C 3-20 cycloalkyl, or C 3-10 cycloalkyl, which may be substituted; , Mono- or bicycloaliphatic.
  • aryl described alone or in combination with other substituents, may include C 6-30 aryl, C 6-20 aryl, or C 6-10 aryl, which may be substituted, and the adjacent carbons. Double bonds alternate (resonance) between atoms or suitable heteroatoms.
  • alkoxy refers to an alkyl group single bond with oxygen, for example, linear or branched C 1 -C 20 alkoxy, C 1 -C 15 alkoxy, C 1 which may be substituted -C 10 alkoxy, or C 1 -C 6 alkoxy, and may include, for example, methoxy, ethoxy, propoxy, butoxy, pentyloxy, heptyloxy and the like and all possible isomers thereof. It may be, but may not be limited thereto.
  • aryloxy refers to an aryl group single bond with oxygen, wherein the aryl group single bond with oxygen may be substituted C 6-30 aryl, C 6-20 aryl, or C 6-10 It may include an aryl, for example, a phenyl ring, toluyl ring, naphthalenyl ring, anthracenyl ring, phenanthrene ring, pentarene ring, indene ring, biphenylene ring, phenylene ring, azulene Ring, heptarene ring, acenaphthylene ring, fluorene ring, tetracene ring, triphenylene ring, pyrene ring, chrysene ring, ethyl-chrysene ring, pisene ring, perylene ring, pentaphene ring, pentacene Ring, tetraphenylene
  • alkylcarboxyl group includes an alkoxy group mono-bonded with carbon of a carbonyl group in an ester group, wherein the alkoxy group included in the alkylcarboxyl group is, for example, linear or branched C which may be substituted. 1 -C 20 alkoxy, C 1 -C 15 alkoxy, C 1 -C 10 alkoxy, or C 1 -C 6 alkoxy, for example, methoxy, ethoxy, propoxy, butoxy, Pentyloxy, heptyloxy, and the like and all possible isomers thereof, but may not be limited thereto.
  • arylcarboxyl group includes an aryloxy group single-bonded with carbon of a carbonyl group in an ester group, and the aryl group single-bonded with oxygen in the aryloxy group included in the arylcarboxyl group may be substituted.
  • arylmercapto group refers to an aryl group single bond with sulfur, wherein the aryl group single bond with sulfur may be substituted C 6-30 aryl, C 6-20 aryl, or C 6 It may include -10 aryl, for example, a phenyl ring, toluyl ring, naphthalenyl ring, anthracenyl ring, phenanthrene ring, pentarene ring, indene ring, biphenylene ring, phenylene ring, Azulene ring, heptarene ring, acenaphthylene ring, fluorene ring, tetracene ring, triphenylene ring, pyrene ring, chrysene ring, ethyl-crisene ring, pysene ring, perylene ring, pentafen ring, Pentacene ring, te
  • halogen is a Group 17 element of the periodic table, which may include, for example, F, Cl, Br, or I, but may not be limited thereto.
  • a first aspect of the present application provides a perylene-based compound represented by Formula 1 below:
  • R 1 and said R 2 are, each independently, hydrogen, halogen, cyano, C 1-20 alkyl group which may be substituted with a linear or branched, optionally substituted C 3-30 cycloalkyl Alkyl group, C 6-30 aryl group which may be substituted, C 1-20 alkylamine group which may be substituted, C 3-30 cycloalkylamine group which may be substituted, C 6- which may be substituted 30 arylamine group, a linear or branched C 1-20 alkoxy group which may be substituted, a C 3-30 cycloalkoxy group which may be substituted, a C 6-30 aryloxy group which may be substituted, a linear which may be substituted Or a branched C 2-10 alkylcarboxyl group, a substituted C 6-30 arylcarboxyl group, or a substituted C 6-30 arylmercapto group, wherein R 3 and R 4 are each independently hydrogen , Halogen group, cyan
  • the alkyl group, the alkylamine group, the alkoxy group, and the alkylcarboxyl group independently included in each of R 1 to R 4 may be substituted linearly having about 1 to about 20 carbon atoms. Or branched alkyl groups. As used herein, a linear or branched alkyl group has about 1 to about 20 carbon atoms, about 1 to about 15 carbon atoms, about 1 to about 10 carbon atoms, or about 1 to 6 carbon atoms.
  • It may include an alkyl group, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, octadecyl, nona Decyl, eicosanyl, or all possible isomers thereof.
  • it may be an alkyl group having 1 to 12 carbon atoms, that is, methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl, undecyl, dodecyl group, Or an alkyl group having 1 to 6 carbon atoms, that is, a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, or a hexyl group, or an alkyl group having 1 to 4 carbon atoms, that is, a methyl group, an ethyl group, or an i-propyl group. , n-propyl group, t-butyl group, s-butyl group, or n-butyl group.
  • the cycloalkyl group, the cycloalkylamine group, and the cycloalkoxy group independently included in each of R 1 to R 4 include a substituted cycloalkyl group having about 3 to about 30 carbon atoms. This may include a single cyclic ring or a polycyclic ring to which a single cyclic ring is linked or fused. As used herein, a cycloalkyl group includes about 3 to about 30, about 3 to about 25, about 3 to about 20, about 3 to about 15, about 3 to about 10, about 5 to about 30, about 5 to about carbon atoms.
  • a cycloalkyl group for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclohexenyl, cycloheptyl, cycloheptenyl, cyclooctyl, cyclooctenyl, 2,5-cyclohexadiee Nyl, bicyclo [2.2.2] octyl, adamant-1-yl, decahydronaphthyl, oxocyclohexyl, dioxocyclohexyl, thiocyclohexyl, 2-oxobicyclo [2.2.1] hept-1 -One, or all possible isomers thereof, but may not be limited thereto.
  • aryl group may include a substituted aryl group having about 6 to about 30 carbon atoms, which may be a phenyl group or a polycyclic ring in which two or more phenyl groups are linked or fused.
  • the aryl group may include an aryl group having about 6 to about 30 carbon atoms, about 6 to about 25, about 6 to about 20, about 6 to about 15, or about 6 to about 10 carbon atoms, for example, phenyl Ring, toluyl ring, naphthalenyl ring, anthracenyl ring, phenanthrene ring, pentarene ring, indene ring, biphenylene ring, phenylene ring, azylene ring, heptarene ring, acenaphthylene ring, fluorene Ring, tetracene ring, triphenylene ring, pyrene ring, chrysene ring, ethyl-crysene ring, pisene ring, perylene ring, pentaphene ring, pentacene ring, tetraphenylene ring, hexaphene ring, hexacene
  • the aryl group contained in the aryl group, the arylamine group, the aryloxy group, the arylcarboxyl group or the arylmercapto group independently contained in each of R 1 to R 4 , a phenyl group, It may include a biphenyl group or a naphthyl group, but is not limited thereto.
  • the substituents that may be substituted for R 1 and R 2 are each independently a halogen group, cyano group, linear or branched C 1-8 alkyl group, or linear or branched C It may be to include a 1-8 alkoxy group, but is not limited thereto.
  • the substituents that may be independently substituted for each of R 3 and R 4 are each independently a halogen group, cyano group, linear or branched C 1-8 alkyl group, or linear or branched group. It may be to include a C 1-8 alkoxy group of the topography, but is not limited thereto.
  • the linear or branched C 1-8 alkyl group or the linear or branched C 1-8 alkoxy group which may be substituted with R 1 to R 4 has about 1 to about 8 carbon atoms. It may include, but is not limited to, linear or branched alkyl groups.
  • the linear or branched alkyl group has about 1 to about 8 carbon atoms, about 1 to about 7, about 1 to about 6, about 1 to about 5, about 1 to about 4, about 1 to about 3, or about 1 carbon atoms.
  • To about 2 alkyl groups including methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, or all possible isomers thereof.
  • an alkyl group having 1 to 8 carbon atoms that is, a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, or an alkyl group having 1 to 6 carbon atoms, that is, a methyl group ,
  • the perylene-based compound may include, but may not be limited to:
  • a C 1-20 alkane compound which may be substituted with a compound represented by Formula 2 below a C 6-30 cycloalkane compound which may be substituted, a C 6-30 aryl compound which may be substituted, and a substitution C 6-30 phenolic compound which may be substituted, C 1-20 alcoholic compound which may be substituted, C 1-20 alkylamine compound which may be substituted, C 6-30 cycloalkylamine compound which may be substituted,
  • a process for preparing a perylene based compound according to the first aspect comprising reacting with a C 6-30 arylamine compound, or N-halosuccinimide, which may be:
  • R 5 to R 8 are each independently hydrogen, halogen or a linear or branched C 2-10 alkylcarboxyl group which may be substituted.
  • substitutable C 6-30 phenolic compounds capable of reacting with the compound represented by Formula 2 are each independently hydroxyphenyl, dihydroxyphenyl, meth Methoxyphenyl, dimethoxyphenyl, trimethoxyphenyl, ethoxyphenyl, diethoxyphenyl, triethoxyphenyl, propoxyphenyl, dipropoxyphenyl, isopropoxyphenyl, diisopropoxyphenyl, butoxyphenyl, hydroxide Hydroxyphenyl, dihydroxyphenyl, cyanophenyl, carboxyphenyl, carboxamidophenyl, N-methylcarboxamidophenyl, acetylaminophenyl, propionylaminophenyl, butyrylaminophenyl, N-phenylaminophenyl, N- (o-tolyl) aminophenyl, N- (m-tolyl) aminophenyl, N- (p-to
  • the C 1-20 alcohol-based compound which may be reacted with the compound represented by Formula 2 is, for example, each independently hydroxyethyl, hydroxypropyl, dihydrate Hydroxypropyl, hydroxybutyl, dihydroxybutyl, hydroxypentyl, dihydroxypentyl, hydroxyhexyl, dihydroxyhexyl, hydroxyheptyl, dihydroxyheptyl, and all isomers thereof It may include, but is not limited to.
  • the compound represented by the formula (2) may include reacting with one selected from the group consisting of all isomers.
  • the compound represented by Formula 2 is phenol, 2-phenylphenol, 2,4-di-tert-butylphenol, 4-hydroxy-3-tert-butylanisole, N- And reacting with one selected from the group consisting of bromosuccinimide, hexylamine, and all isomers thereof.
  • the perylene-based compound prepared in the group consisting of halogen, cyanide salt, phenolic compound, naphthol-based compound, alcohol-based compound, thiol-based compound, amine-based compound and boronic acid that can be substituted The reaction may be further performed by adding a material selected from the reaction one to three times.
  • the prepared perylene-based phenol compound and naphthol-based compound for example, each independently hydroxyphenyl, dihydroxyphenyl, methoxyphenyl, dimethoxyphenyl, Trimethoxyphenyl, ethoxyphenyl, diethoxyphenyl, triethoxyphenyl, propoxyphenyl, dipropoxyphenyl, isopropoxyphenyl, diisopropoxyphenyl, butoxyphenyl, hydroxyphenyl, dihydroxyphenyl , Cyanophenyl, carboxyphenyl, carboxamidophenyl, N-methylcarboxamidophenyl, acetylaminophenyl, propionylaminophenyl, butyrylaminophenyl, N-phenylaminophenyl, N- (o-tolyl) aminophenyl , N- (m-tolyl) aminophenyl, N- (p-tolyl) aminophen
  • the prepared perylene-based alcohol compound is, for example, each independently hydroxyethyl, hydroxypropyl, dihydroxypropyl, hydroxybutyl, dihydroxybutyl , Hydroxypentyl, dihydroxypentyl, hydroxyhexyl, dihydroxyhexyl, hydroxyheptyl, dihydroxyheptyl, and all isomers thereof, but are not limited thereto. no.
  • the prepared perylene-based reactable amine compound is, for example, each independently amino group, methylamino, dimethylamino, ethylamino, diethylamino, propylamino, dipropylamino , Diisopropylamino, dibutylamino, diisobutylamino, di-tert-butylamino, dipentylamino, dihexylamino, diphenylamino, di-o-tolylamino, di-m-tolylamino, di- p-tolylamino, di (4-cyanophenyl) amino, and all isomers thereof, but are not limited thereto.
  • the reaction may be further performed once to three times by adding the boronic acid, and one selected from the group consisting of all isomers thereof.
  • it may further include, but is not limited to, adding a carbonate salt in some or all of the above reaction step.
  • the carbonate salt forms a basic atmosphere in each reaction step.
  • alkali metal carbonates such as sodium carbonate, potassium carbonate, and cesium carbonate or alkali metal hydroxides such as sodium hydroxide or potassium hydroxide may be used for the same purpose. However, it is not limited thereto.
  • the reaction may be to include the reaction by dissolving the reactants in an organic solvent, and then precipitated and filtered at room temperature, but is not limited thereto.
  • the reactions range from room temperature to about 200 ° C., for example, room temperature to about 200 ° C., room temperature to about 180 ° C., room temperature to about 160 ° C., room temperature to about 140 ° C., room temperature to about 120 °C, room temperature to about 100 °C, room temperature to about 80 °C, about 70 °C to about 200 °C, about 70 °C to about 180 °C, about 70 °C to about 160 °C, about 70 °C to about 140 °C, about 80 °C to It may be performed at a temperature of about 130 °C, about 100 °C to about 130 °C, about 110 °C to about 130 °C, or about 120 °C to about 130 °C, but is not limited thereto.
  • the preparation method may include a C 1-20 alkane compound which may be substituted with the compound of Formula 2, a C 6-30 cycloalkane compound which may be substituted, in an organic solvent, C 6-30 aryl compound which may be substituted, C 6-30 phenolic compound which may be substituted, C 1-20 alcohol compound which may be substituted, C 1-20 alkylamine compound which may be substituted, may be substituted Adding a C 6-30 cycloalkylamine compound, a substitutable C 6-30 arylamine compound, or N-halosuccinimide, and reacting at a temperature of from about room temperature to about 200 ° C., followed by precipitation and filtration at room temperature. It may be included, but is not limited thereto.
  • the production method is a halogen, cyanide salt, phenolic compound, naphthol-based compound, alcohol-based compound, thiol-based compound, amine-based compound and the above-mentioned perylene-based compound dissolved in an organic solvent
  • a material selected from the group consisting of boronic acid which may be substituted the reaction may be performed at room temperature to about 200 ° C., followed by precipitation and filtration at room temperature, but is not limited thereto.
  • the organic solvent may be used without limitation so long as it is an organic solvent usable in the art, for example, dimethylformamide, tetrahydrofuran, methylene chloride, acetone, acetonitrile, dimethyl Sulfoxide, hexamethylphosphoamide, pyridine, pyrimidine, imidazole, quinoline, isoquinoline, quinaldine, N-methylpiperidine, N-methylpiperidone, N-methylpyrrolidone, dimethylformamide, dimethyl It may include acetamide, or tetramethylurea, but is not limited thereto.
  • the organic solvent may be used in about 5 g to about 120 g per g of perylene raw material, but is not limited thereto.
  • the third aspect of the present application provides a fluorescent dye comprising the perylene-based compound according to the present application.
  • the fluorescent dye may be a green fluorescent dye, but may not be limited thereto.
  • the fluorescent dye may be used as, but not limited to, a fluorescent dye for coloring high molecular weight organic and inorganic materials, in particular plastics, paints, printing inks, inorganic-organic composites, and oxide layer systems. You may not.
  • the fluorescent dyes can be used as dispersants, pigment additives for organic pigments and intermediates for producing fluorescent dyes and pigment additives, or dispersants for preparing inkjet inks and aqueous polymer dispersions which absorb and / or emit in the yellow region of the electromagnetic spectrum. It may be used as a pigment additive and an intermediate, but may not be limited thereto.
  • the fluorescent dye may be used as a dispersant, a photoconductor for electrophotography, as a coloring component or color correction component of a luminescent color filter, a semi-transparent color filter, and a retroreflective element, or as an electron emission source of an electroluminescent device and a chemiluminescent device. This may not be limited.
  • the fluorescent dye may be used as an active component of fluorescence conversion, fluorescent solar collectors, bioluminescent arrays, and photovoltaic, or as a laser dye, but may not be limited thereto.
  • the fluorescent dye is a fluorescent dye for reactive coloring of high molecular weight organic and inorganic materials, in particular plastics, paints, printing inks, inorganic-organic composites, or in the yellow region of the electromagnetic spectrum and / or Or as fluorescent dyes for preparing bleeding-resistant aqueous polymer dispersions, but may not be limited thereto.
  • the fluorescent dye may be used as a coloring component or color correction component of a luminescent color filter and a semi-transparent color filter and a retroreflective element, or as a migration-stable electron emission source of an electroluminescent device and a chemiluminescent device. This may not be limited
  • fluorescent dye according to this aspect may be applied to all the contents described for the first to second aspects of the present application, but may not be limited thereto.
  • MALDI-TOF analysis calculated molecular weight 705, measured molecular weight 704
  • the intermediate 1 (1.00 mmol) was dissolved in 10 mL of dimethylformamide, followed by addition of phenol (5.00 mmol) and potassium carbonate (5.00 mmol). After stirring at 130 ° C. for 6 hours, the temperature was lowered to room temperature. The reactant was added to 20 mL of 5% aqueous ammonium chloride solution, and the resulting precipitate was filtered and washed with 30 mL of water to yield Compound 1 (yellow solid, yield: 68%).
  • MALDI-TOF analysis calculated molecular weight 758, measured molecular weight 756
  • MALDI-TOF analysis calculated molecular weight 786, measured molecular weight 785
  • Example 1 Compound 1 (1.00 mmol) in Example 1 was dissolved in 10 mL of dimethylformamide, and then cyclohexanol (5.00 mmol) and cesium carbonate (5.00 mmol) were added thereto. After stirring at 130 ° C. for 12 hours, the temperature was lowered to room temperature. The resulting precipitate was filtered by adding the mixed solution to 20 mL of 5% aqueous ammonium chloride solution, and then washed with 30 mL of water to obtain compound 8 (yellow solid, yield: 42%).
  • the compound 10 (1.00 mmol) was dissolved in 5 mL of tetrahydrofuran, and stirred with 3 mL of water, phenylboronic acid (4.00 mmol) and sodium carbonate (4.00 mmol). Pd (PPh 3 ) 4 (0.01 mmol) was added as a catalyst and refluxing was performed at 70 ° C. for 12 hours. After the temperature was lowered, the water layer was removed with a separatory funnel, and then poured into 10 mL of methanol to form crystals. The resulting crystals were filtered and washed with 20 mL each of water and methanol to obtain compound 11 (light yellow solid, yield: 30%).
  • MALDI-TOF analysis calculated molecular weight 654, measured molecular weight 654
  • Example 9 Compound 10 (1.00 mmol) in Example 9 was dissolved in 10 mL methylene chloride, and bromine (3 mmol) was added thereto, followed by stirring at room temperature. After 6 hours, crystals were formed by pouring into 50 mL of methanol and washed three times with a filter and 50 mL of water to obtain Compound 14 (light yellow solid, yield: 76%).
  • MALDI-TOF analysis calculated molecular weight 768, measured molecular weight 768
  • the compound 14 (1.00 mmol) was dissolved in 5 mL of tetrahydrofuran, and stirred with 3 mL of water, phenylboronic acid (6.00 mmol) and sodium carbonate (6.00 mmol). Pd (PPh 3 ) 4 (0.01 mmol) was added as a catalyst and refluxing was performed at 70 ° C. for 12 hours. After the temperature was lowered, the water layer was removed with a separatory funnel, and then poured into 10 mL of methanol to form crystals. The resulting crystals were filtered and washed with 20 mL each of water and methanol to give compound 15 (light orange solid, yield: 22%).
  • MALDI-TOF analysis calculated molecular weight 756, measured molecular weight 756
  • Example 10 Compound 14 (1.00 mmol) in Example 10 was dissolved in 10 mL of dimethylformamide, followed by addition of copper cyanide (6 mmol). After stirring at 150 ° C. for 8 hours, the temperature was lowered and poured into 30 mL of water to form crystals. The resulting crystals were filtered and washed with 50 mL of methanol to yield compound 17 (red solid, yield: 72%).
  • MALDI-TOF analysis calculated molecular weight 564, measured molecular weight 564
  • MALDI-TOF analysis calculated molecular weight 722, measured molecular weight 721
  • the compound 19 (1.00 mmol) was dissolved in 5 mL of tetrahydrofuran, and stirred with 3 mL of water, phenylboronic acid (4.00 mmol) and sodium carbonate (4.00 mmol). Pd (PPh 3 ) 4 (0.01 mmol) was added as a catalyst and refluxing was performed at 70 ° C. for 12 hours. After the temperature was lowered, the water layer was removed with a separatory funnel, and then poured into 10 mL of methanol to form crystals. The resulting crystals were filtered and washed with 20 mL each of water and methanol to give compound 20 (orange solid, yield: 23%).
  • MALDI-TOF analysis calculated molecular weight 716, measured molecular weight 716
  • Example 9 Compound 10 (1.00 mmol) in Example 9 was dissolved in 10 mL of dimethylformamide, and then stirred at 130 ° C. for 6 hours with phenol (3.00 mmol) and potassium carbonate (3.00 mmol). Lowered. The resulting precipitate was added to 20 mL of 5% aqueous ammonium chloride solution and the resulting precipitate was filtered and washed with 30 mL of water to yield Compound 21 (yellow solid, yield: 68%).
  • Example 9 Compound 10 (1.00 mmol) in Example 9 was dissolved in 10 mL of dimethylformamide, and 2-phenylphenol (5.00 mmol) and cesium carbonate (5.00 mmol) were added thereto. After stirring at 130 ° C. for 8 hours, the temperature was lowered to room temperature. The resulting precipitate was added to 20 mL of 5% aqueous ammonium chloride solution and the resulting precipitate was filtered and washed with 30 mL of water to yield Compound 22 (yellow solid, yield: 52%).
  • MALDI-TOF analysis calculated molecular weight 788, measured molecular weight 790
  • Example 9 Compound 10 (1.00 mmol) in Example 9 was dissolved in 10 mL of dimethylformamide, followed by addition of aniline (3.00 mmol) and cesium carbonate (3.00 mmol). After stirring at 130 ° C. for 12 hours, the temperature was lowered to room temperature. The resulting precipitate was filtered by adding the mixed solution to 20 mL of 5% aqueous ammonium chloride solution, and then washed with 30 mL of water to obtain Compound 23 (yellow solid, yield: 48%).
  • MALDI-TOF analysis calculated molecular weight 636, measured molecular weight 636
  • Example 9 Compound 10 (1.00 mmol) in Example 9 was dissolved in 10 mL of dimethylformamide, and 2-naphthol (3.00 mmol) and cesium carbonate (3.00 mmol) were added thereto. After stirring at 130 ° C. for 10 hours, the temperature was lowered to room temperature. The resulting precipitate was filtered by adding the mixed solution to 20 mL of 5% aqueous ammonium chloride solution, and then washed with 30 mL of water to obtain compound 24 (dark yellow solid, yield: 62%).
  • MALDI-TOF analysis calculated molecular weight 736, measured molecular weight 737
  • Example 9 Compound 10 (1.00 mmol) in Example 9 was dissolved in 10 mL of dimethylformamide, followed by addition of 4-tert-butylbutylphenol (3.00 mmol) and potassium carbonate (3.00 mmol). After stirring at 130 ° C. for 6 hours, the temperature was lowered to room temperature. The resulting precipitate was filtered by adding the mixed solution to 20 mL of 5% aqueous ammonium chloride solution, and then washed with 30 mL of water to obtain Compound 25 (yellow solid, yield: 63%).
  • MALDI-TOF analysis calculated molecular weight 748, measured molecular weight 747
  • Example 9 Compound 10 (1.00 mmol) in Example 9 was dissolved in 10 mL of dimethylformamide, followed by addition of 2-methyl-2-propanol (5.00 mmol) and cesium carbonate (5.00 mmol). After stirring at 130 ° C. for 24 hours, the temperature was lowered to room temperature. The resulting precipitate was filtered by adding the mixed solution to 20 mL of 5% aqueous ammonium chloride solution and then washed with 30 mL of water to give compound 27 (yellow solid, yield: 38%).
  • MALDI-TOF analysis calculated molecular weight 654, measured molecular weight 654
  • Example 9 Compound 10 (1.00 mmol) in Example 9 was dissolved in 10 mL of dimethylformamide, followed by addition of 4-methoxythiophenol (4.00 mmol) and cesium carbonate (4.00 mmol). After stirring at 130 ° C. for 24 hours, the temperature was lowered to room temperature. The resulting precipitate was filtered by adding the mixed solution to 20 mL of 5% aqueous ammonium chloride solution, and then washed with 30 mL of water to obtain Compound 29 (orange solid, yield: 63%).
  • MALDI-TOF analysis calculated molecular weight 728, measured molecular weight 728
  • Propylene glycol monomethyl ether acetate was added to each of the perylene-based compounds (1000 ppm) and stirred for 10 minutes in order to confirm the optical properties of absorption and fluorescence for the perylene-based compounds 1 to 29 synthesized as in Example. Thereafter, additional propylene glycol monomethyl ether acetate was added and the concentration was diluted to 20 ppm, followed by absorption and absorption using a UV / Vis / NIR spectrophotometer (UV3600-shimadzu) and a spectrophotometer (RF-5301PC-shimadzu). Fluorescence was measured and the results are shown in Table 1 below. As a comparative example, commercially available Lumogen F Yellow 083 (BASF) was used.
  • Table 1 shows the maximum absorption wavelength ( ⁇ max), maximum emission wavelength ( ⁇ emission) and molar extinction coefficient ( ⁇ ) for the dye compounds prepared as in the above examples and as a comparative example, Lumogen 083.
  • ⁇ max maximum absorption wavelength
  • ⁇ emission maximum emission wavelength
  • ⁇ molar extinction coefficient
  • Table 1 shows the maximum absorption wavelength ( ⁇ max), maximum emission wavelength ( ⁇ emission) and molar extinction coefficient ( ⁇ ) for the dye compounds prepared as in the above examples and as a comparative example, Lumogen 083.
  • ⁇ max maximum absorption wavelength
  • ⁇ emission maximum emission wavelength
  • ⁇ molar extinction coefficient
  • FIG. 1 shows the maximum absorption wavelength (solid line) and the maximum emission wavelength (dotted line) of compounds 2, 7 and 9, which are compounds having high solubility in organic solvents and high molar coefficients among dye compounds according to the present example.
  • the compound and the solvent were mixed in a 25 mL vial bottle at a concentration of about 3% to about 5%, the vial bottle was completely sealed, shaken for 15 minutes, and after 30 minutes, the presence of a liquid precipitate was visually observed. When the precipitate was confirmed, it was determined that the solubility is poor.
  • As a solubility determination criterion when completely dissolved at 3% or more,? Is indicated by O, when dissolved at 3% or less, and partially dissolved or by X when not dissolved (Table 2). As can be seen in Table 2, it was confirmed that the solubility of the perylene-based compound of the present application is superior to the conventional fluorescent dyes.

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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La présente invention concerne un nouveau composé à base de pérylène, un procédé de préparation associé, ainsi qu'un colorant fluorescent le comprenant.
PCT/KR2016/009517 2015-08-26 2016-08-26 Composé à base de pérylène, procédé de préparation associé, et colorant fluorescent le comprenant Ceased WO2017034370A1 (fr)

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KR102253839B1 (ko) 2017-11-16 2021-05-20 에스에프씨 주식회사 표지용 염료 및 이를 포함하는 키트
KR102539870B1 (ko) 2018-09-12 2023-06-05 동우 화인켐 주식회사 자발광 감광성 수지 조성물, 이를 이용한 색변환층을 포함하는 컬러필터 및 화상표시장치
JP2020083982A (ja) * 2018-11-21 2020-06-04 住友化学株式会社 着色硬化性樹脂組成物、カラーフィルタ、表示装置及び化合物
KR102607871B1 (ko) 2019-03-29 2023-11-29 동우 화인켐 주식회사 자발광 감광성 수지 조성물, 이를 이용한 색변환층을 포함하는 컬러필터 및 화상표시장치
KR102204532B1 (ko) 2019-05-28 2021-01-19 동우 화인켐 주식회사 자발광 감광성 수지 조성물, 이를 이용하여 제조된 색변환층 및 이를 포함하는 컬러필터 및 화상표시장치
KR102760849B1 (ko) 2020-02-20 2025-02-03 동우 화인켐 주식회사 자발광 감광성 수지 조성물, 이로부터 제조된 색변환층을 포함하는 컬러필터 및 화상표시장치
KR20210106170A (ko) 2020-02-20 2021-08-30 동우 화인켐 주식회사 자발광 감광성 수지 조성물, 이로부터 제조된 색변환층을 포함하는 컬러필터 및 화상표시장치
KR20210121648A (ko) 2020-03-31 2021-10-08 동우 화인켐 주식회사 자발광 감광성 수지 조성물, 이를 이용하여 제조된 색변환층 및 이를 포함하는 컬러필터 및 화상표시장치
KR20210121752A (ko) 2020-03-31 2021-10-08 동우 화인켐 주식회사 자발광 감광성 수지 조성물, 이를 이용하여 제조된 색 변환층 및 화상표시장치
KR102772174B1 (ko) 2020-03-31 2025-02-25 동우 화인켐 주식회사 자발광 감광성 수지 조성물, 이를 이용하여 제조된 색변환층 및 이를 포함하는 컬러필터 및 화상표시장치
WO2022191485A1 (fr) 2021-03-10 2022-09-15 에스에프씨 주식회사 Rapporteur et son utilisation

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