KR101867399B1 - Perylene-based compounds, method of producing the same, and fluorescent dye including the same - Google Patents

Abstract

The present invention relates to a novel perylene compound, a process for producing the same, and a fluorescent dye containing the same.

Description

TECHNICAL FIELD [0001] The present invention relates to a perylene-based compound, a method for producing the same, and a fluorescent dye containing the same. BACKGROUND OF THE INVENTION 1. Field of the Invention [0001]

The present invention relates to a novel perylene-based compound, a process for producing the same, and a fluorescent dye containing the same.

The perylene-based compound is a polycyclic aromatic hydrocarbon compound and is used as a liquid fluorescent dye, and has been particularly popular as an excellent light-safe pigment and a bat dye. Pigments and dyes including a perylene group compound exhibit emission wavelengths in a long wavelength due to their extended vacancy and are used in various fields because of their very strong fluorescence. Recently, their use as a chemiluminescent material in a display field has been greatly increased Patent Publication No. US2011 / 0251393).

The present invention is to provide a novel perylene compound, a process for producing the same, and a fluorescent dye containing the same.

However, the problems to be solved by the present invention are not limited to the problems described above, and other problems not described can be clearly understood by those skilled in the art from the following description.

A first aspect of the present invention provides a perylene-based compound represented by the following Formula 1:

[Chemical Formula 1]

In the formula 1, wherein 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, optionally substituted C _6-30 aryl group, which may be C _1-20 alkyl which may be substituted with a linear or branched amine group, a substituted C _3-30 cycloalkyl amine groups, which may be substituted with C _{6- 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 Or a branched C _2-10 alkylcarboxyl group, a C _6-30 arylcarboxyl group which may be substituted, or a C _{6-30 arylmercapto} group which may be substituted, and R ₃ and R ₄ are each independently hydrogen , A halogen group, a cyano group, a linear or branched C _1-20 alkyl group which may be substituted, a C _3-30 cycloalkyl group which may be substituted , A C _6-30 aryl group which may be substituted, a linear or branched C _1-20 alkoxy group which may be substituted, a C _3-30 cycloalkoxy group which may be substituted, or C _6-30 aryl It is jade.

Present the second side, to C ₆ in the compound represented by the formula 2, C _1-20 alkanes which may be substituted with a compound of linear or branched, C _3-30 cycloalkane compound which may be substituted, may be substituted _-30 aryl compound, a C _6-30 phenol compound which may be substituted, a linear or branched C _1-20 alcohol compound which may be substituted, a linear or branched C _1-20 alkylamine compound which may be substituted , A C _3-30 cycloalkylamine compound that may be substituted, a C _6-30 arylamine compound that may be substituted, or N-halosuccinimide. The method provides:

(2)

In Formula 2, R ₅ to R ₈ are each independently hydrogen, halogen, or a linear or branched C _2-10 alkylcarboxyl group which may be substituted.

A third aspect of the present invention provides a fluorescent dye comprising a perylenic compound according to the present invention.

The perylene-based compound of the present invention is a novel compound that can be used as a green fluorescent dye having perylene as a perinuclear structure, and exhibits excellent solubility, particularly excellent solubility, durability, thermal stability, and luminescent property with respect to an organic solvent.

BRIEF DESCRIPTION OF THE DRAWINGS FIG. 1 is a spectrum showing UV / PL results of a perillin compound according to one embodiment of the present invention. FIG.

Hereinafter, embodiments and examples of the present invention will be described in detail with reference to the accompanying drawings, which will be readily apparent to those skilled in the art to which the present invention pertains.

It should be understood, however, that the present invention may be embodied in many different forms and is not limited to the embodiments and examples described herein. In order to clearly illustrate the present invention, parts not related to the description are omitted, and similar parts are denoted by like reference characters throughout the specification.

Throughout this specification, when a member is "on " another member, it includes not only when the member is in contact with the other member, but also when there is another member between the two members.

Throughout this specification, when an element is referred to as "including " an element, it is understood that the element may include other elements as well, without departing from the other elements unless specifically stated otherwise. The terms "about "," substantially ", etc. used to the extent that they are used throughout the specification are intended to be taken to mean the approximation of the manufacturing and material tolerances inherent in the stated sense, Accurate or absolute numbers are used to help prevent unauthorized exploitation by unauthorized intruders of the referenced disclosure. The word " step (or step) "or" step "used to the extent that it is used throughout the specification does not mean" step for.

Throughout this specification, the term "combination thereof" included in the expression of the machine form means one or more combinations or combinations selected from the group consisting of the constituents described in the expression of the machine form, And the like.

Throughout this specification, the description of "A and / or B" means "A or B, or A and B".

Throughout the present specification, alone or in the term "alkyl" described in combination with other substituents are linear or branched, optionally substituted, C ₁ -C ₂₀ alkyl, C ₁ -C ₁₅ alkyl, C ₁ -C ₁₀ alkyl, or C ₁ -C ₆ alkyl and include, for example, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl or all possible isomers thereof , But may not be limited thereto.

Throughout the specification, the term "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. Cyclobutyl, cyclopentyl, cyclohexyl, cyclohexenyl, cycloheptyl, cycloheptenyl, cyclooctyl, cyclooctenyl, 2,5-cyclohexadienyl, bicyclo [2.2.2] 2-oxocyclo [2.2.1] hept-1-yl, or any of the possible isomers thereof, or a pharmaceutically acceptable salt, solvate or prodrug thereof. But are not limited thereto.

Throughout this specification, the term "aryl ", 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, The double bonds alternate (resonate) between the atoms or the appropriate heteroatoms. Examples of the hetero ring include a phenyl ring, a tolyl ring, a naphthalenyl ring, an anthracenyl ring, a phenanthrene ring, a pentaren ring, an indene ring, a biphenylene ring, a phenalene ring, A heterocyclic ring, a thiophene ring, a thienylene ring, a fluorene ring, a tetracene ring, a triphenylene ring, a pyrene ring, a chrysene ring, an ethyl-chrysene ring, a picene ring, a perylene ring, a pentaphene ring, A phenanthrene ring, a hexane ring, a rubisen ring, a coronene ring, a trinaphthylene ring, a heptaphene ring, a heptacene ring, a pyranthrene ring, an obaren ring, a fluoransen ring, A phenanthryl group, a 1-pyrenyl group, a chrysene group, a naphthacene group, a coronyl group, and derivatives thereof, But may not be limited.

For the purposes of the present specification, the term "alkoxy" means an alkyl group mono-bonded to oxygen, for example, linear or branched C ₁ -C ₂₀ alkoxy which may be substituted, C ₁ -C ₁₅ alkoxy, C ₁ -C ₁₀ alkoxy, or C ₁ -C ₆ alkoxy may be one containing, for example, methoxy, ethoxy, propoxy, butoxy, pentyloxy, heptyloxy, and the like thereof to include all possible isomers But may not be limited thereto.

Throughout the present specification, the term "aryloxy" is to mean a group of a single bond and oxygen, aryl, C _6-30 aryl which may be substituted aryl groups with a single bond and oxygen, C _6-20 aryl, or C _6-10 And examples thereof include a phenyl ring, a tolyl ring, a naphthalenyl ring, an anthracenyl ring, a phenanthrene ring, a pentaren ring, an indene ring, a biphenylene ring, a phenalene ring, azene A heterocyclic ring, a heterocyclic ring, a heterocyclic ring, an acenaphthylene ring, an acenaphthylene ring, a fluorene ring, a tetracene ring, a triphenylene ring, a pyrene ring, a chrysene ring, A heterocyclic ring, a heterocyclic ring, a heterocyclic ring, a heterocyclic ring, a heterocyclic ring, a heterocyclic ring, a heterocyclic ring, a tetraphenyl ring, a hexaphen ring, a hexasene ring, a rubisene ring, a coronene ring, a trinaphthylene ring, Fluoransene ring, 9-anthryl group, 2-anthryl group, 9-phen May be selected from the group consisting of a trityl group, a 2-phenanthryl group, a 1-pyrenyl group, a chrysene group, a naphthacene group, a coronyl group, and derivatives thereof.

Throughout the specification, the term "alkylcarboxyl group" includes an alkoxy group that is single bonded to the carbon of the carbonyl group in the ester group, and the alkoxy group contained in the alkylcarboxyl group includes, for example, a linear or branched C ₁ -C ₂₀ alkoxy, C ₁ -C ₁₅ alkoxy, C ₁ -C ₁₀ alkoxy, or C ₁ may be one containing a -C ₆ alkoxy, e.g., methoxy, ethoxy, propoxy, butoxy, Pentyloxy, heptyloxy, and the like, as well as all possible isomers thereof.

Throughout this specification, the term "arylcarboxyl group" includes an aryloxy group which is mono-bonded to the carbon of the carbonyl group in the ester group, and the aryl group mono-bonded to oxygen in the aryloxy group contained in the arylcarboxyl group may be substituted C _6-30 aryl, C _6-20 aryl, or may be one containing a C _6-10 aryl group, for example, a phenyl ring, toluyl ring, naphthalenyl ring, anthracenyl ring, a phenanthrene ring, a cyclopenta An acenaphthylene ring, an acenaphthylene ring, a fluorenone ring, a tetracene ring, a triphenylene ring, a pyrenylene ring, a chrysene ring, an ethylenic ring, an acenaphthylene ring, an indene ring, a biphenylene ring, a phenylene ring, A hexene ring, a hexane ring, a rubisene ring, a coronene ring, a trinaphthylene ring, a heptane ring, a heptane ring, a heptane ring, a heptane ring, Tassen Gori , A pyranthrene ring, an obaren ring, a fluoransen ring, a benzofluoransen ring, a 9-anthryl group, a 2-anthryl group, a 9-phenanthryl group, a 2-phenanthryl group, A naphthacene group, a naphthacene group, a coronyl group, and derivatives thereof, but the present invention is not limited thereto.

Throughout the present specification, the term "aryl mercapto group" is sulfur and a single bond to mean an aryl, wherein the sulfur single bond and the aryl group is C _6-30 aryl, C _6-20 aryl, or C ₆ which may be substituted be one that includes a _-10 aryl, and, for example, a phenyl ring, a toluyl ring, a naphthalenyl ring, anthracenyl ring, a phenanthrene ring, a cyclopenta alkylene ring, indene ring, a biphenylene ring, a page nalren ring, A pyrenylene ring, a pyrenylene ring, a pyrenylene ring, a pyrenylene ring, a chrysene ring, an ethyl-chrysene ring, a picene ring, a perylene ring, a pentaphene ring, A pentacene ring, a tetraphenylene ring, a hexaphen ring, a hexasene ring, a rubisene ring, a coronene ring, a trinaphthylene ring, a heptaphene ring, a heptacene ring, a pyranthrene ring, , Benzofluoransene ring, 9-anthryl group, 2-anthryl group , A 9-phenanthryl group, a 2-phenanthryl group, a 1-pyrenyl group, a chrysene group, a naphthacene group, a coronyl group, and derivatives thereof.

Throughout the specification of the present application, the term "halogen" may include, but is not limited to, Group 17 elements of the periodic table, for example, F, Cl, Br,

A first aspect of the present invention provides a perylene-based compound represented by the following Formula 1:

[Chemical Formula 1]

In the formula 1, wherein 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, optionally substituted C _6-30 aryl group, which may be C _1-20 alkyl which may be substituted with a linear or branched amine group, a substituted C _3-30 cycloalkyl amine groups, which may be substituted with C _{6- 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 Or a branched C _2-10 alkylcarboxyl group, a C _6-30 arylcarboxyl group which may be substituted, or a C _{6-30 arylmercapto} group which may be substituted, and R ₃ and R ₄ are each independently hydrogen , A halogen group, a cyano group, a linear or branched C _1-20 alkyl group which may be substituted, a C _3-30 cycloalkyl group which may be substituted , A C _6-30 aryl group which may be substituted, a linear or branched C _1-20 alkoxy group which may be substituted, a C _3-30 cycloalkoxy group which may be substituted, or C _6-30 aryl It is jade.

In one embodiment of the invention, the alkyl, amine, alkoxy, and alkyl carboxyl groups independently included in each of R ¹ to R ⁴ are substituted linear groups having from about 1 to about 20 carbon atoms Or a branched alkyl group. As used herein, a linear or branched alkyl group can have from about 1 to about 20 carbon atoms, from about 1 to about 15, from about 1 to about 10, or from about 1 to about 6 Alkyl group and may be an alkyl group such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, octadecyl, Decyl, eicosanyl, or all possible isomers thereof. For example, an alkyl group having 1 to 12 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, a nonyl group, a decyl 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, , n-propyl group, t-butyl group, s-butyl group, or n-butyl group.

In one embodiment of the present invention, the cycloalkyl group, the cycloalkylamine group, and the cycloalkoxy group independently included in each of R ¹ to R ⁴ include an optionally substituted cycloalkyl group having about 3 to about 30 carbon atoms , Which may comprise a single cyclic ring or a polycyclic ring fused or fused with a single cyclic ring. As used herein, cycloalkyl groups may have from about 3 to about 30 carbon atoms, from about 3 to about 25, from about 3 to about 20, from about 3 to about 15, from about 3 to about 10, from about 5 to about 30, from about 5 to about 25, about 5 to about 20, about 5 to about 15, about 5 to 10, about 6 to about 30, about 6 to about 25, about 6 to about 20, about 6 to about 15, or about 6 to about 10 And may include a cycloalkyl group. Examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclohexenyl, cycloheptyl, cycloheptenyl, cyclooctyl, cyclooctenyl, 2,5-cyclohexadiyl 2-oxocyclo [2.2.1] hept-1-yl, and the like are preferable, and the heterocyclic ring may be substituted with at least one substituent selected from the group consisting of hydrogen, -, or all possible isomers thereof.

In one embodiment of the present invention, the aryl group, the arylamine group, the aryloxyl group, the arylcarboxyl group, and the arylmercapto group contained in the aryl mercapto group, which are independently included in each of R ₁ to R ₄ , The aryl group may comprise an aryl group that may be substituted having from about 6 to about 30 carbon atoms, which may be a phenyl group or may comprise a polycyclic ring fused with two or more phenyl groups. The aryl group may be an aryl group containing from about 6 to about 30 carbon atoms, from about 6 to about 25, from about 6 to about 20, from about 6 to about 15, or from about 6 to about 10, A heterocyclic ring, an acenaphthylene ring, an acenaphthylene ring, a fluorene ring, a phenylene ring, a biphenylene ring, a phenylene ring, a phenylene ring, an azrene ring, a heptarenylene ring, an acenaphthylene ring, A heterocyclic ring, a tetracene ring, a tetracene ring, a tetracene ring, a triphenylene ring, a pyrene ring, a chrysene ring, an ethyl-chrysene ring, a picene ring, a perylene ring, a pentaphene ring, Anthracene ring, heptadecene ring, heptadecene ring, pyranthrene ring, obaren ring, fluoransen ring, benzofluoransen ring, 9-anthryl group, 2- Anthryl group, 9-phenanthryl group, 2-phenanthryl group, 1-pyreneyl group, Line group, nose group, and may be selected from the group consisting of their derivatives, may not be limited thereto.

In one embodiment of the present invention, the aryl group, the arylamine group, the aryloxy group, the arylcarboxyl group or the aryl group contained in the arylmercapto group, which are independently included in each of R ₁ to R ₄ , A biphenyl group, or a naphthyl group, but the present invention is not limited thereto.

In one embodiment of the present invention, the substituents which may be substituted for R ₁ and R ₂ are each independently a halogen group, a cyano group, a linear or branched C _1-8 alkyl group, or a linear or branched C _{Lt; / RTI} > alkoxy group, but is not limited thereto.

In one embodiment of the present invention, the substituent which can be independently substituted for each of R ₃ and R ₄ is, each independently, a halogen group, a cyano group, a linear or branched C _1-8 alkyl group, Lt; RTI ID = 0.0 > C _1-8 < / RTI > alkoxy group of the terrestrial form.

In one embodiment of the present invention, the linear or branched C _1-8 alkyl group or the linear or branched C _1-8 alkoxy group which may be substituted for R ₁ to R ₄ has a carbon number of about 1 to about 8 But are not limited to, linear or branched alkyl groups. Wherein the linear or branched alkyl group has from about 1 to about 8 carbon atoms, from about 1 to about 7, from about 1 to about 6, from about 1 to about 5, from about 1 to about 4, from about 1 to about 3, To about 2 alkyl groups, and includes methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, or all possible isomers thereof. For example, the 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, , 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 such as a methyl group, an ethyl group, an i-propyl group, -Butyl group, or n-butyl group, but is not limited thereto.

In one embodiment herein, the perylene compound may include, but is not limited to, the following compounds:

Second aspect of the present application is to C _6-30 aryl compound, which may substituted C _6-30 cycloalkane compound, optionally substituted C _1-20 alkanes which may be the compounds, which may be substituted with a substituted a compound represented by the formula (2) be C _6-30 phenol-based compound, which may be substituted with C _1-20 alcohol-based compound, a C _1-20 alkyl amine compound which may be substituted, may be substituted with a C _6-30 cycloalkyl amine compound, which may be optionally substituted , it provides a process for the preparation of a perylene compound of the first aspect, which comprises a C _6-30 aryl amine, or N- halo succinimide which can be reacted with imide:

(2)

In Formula 2, R ₅ to R ₈ are each independently hydrogen, halogen, or a linear or branched C _2-10 alkylcarboxyl group which may be substituted.

In one embodiment of the present invention, the C _6-30 phenol-based compound that can be reacted with the compound represented by Formula 2 is, for example, independently selected from the group consisting of hydroxyphenyl, dihydroxyphenyl, Propoxyphenyl, dipropoxyphenyl, diisopropoxyphenyl, diisopropoxyphenyl, butoxyphenyl, heptoxyphenyl, diethoxyphenyl, trimethoxyphenyl, ethoxyphenyl, diethoxyphenyl, triethoxyphenyl, N-methylcarbamidophenyl, acetylaminophenyl, propionylaminophenyl, butyrylaminophenyl, N-phenylaminophenyl, N-phenylaminophenyl, N-phenylaminophenyl, (o-tolyl) aminophenyl, N- (m-tolyl) aminophenyl, N- (p- tolyl) aminophenyl, Dilaminophenyl, (2-pyrimidyl) aminophenyl, 4- (4-pyrimidyl) aminophenyl, It may include those selected from the group consisting of chedeul However, without being limited thereto.

In one embodiment of the present invention, the C _1-20 alcohol compound which can be reacted with the compound represented by Formula 2 is, for example, independently selected from the group consisting of hydroxyethyl, hydroxypropyl, dihydro Is selected from the group consisting of hydroxypropyl, hydroxypropyl, hydroxybutyl, dihydroxybutyl, hydroxypentyl, dihydroxypentyl, hydroxyhexyl, dihydroxyhexyl, hydroxyheptyl, dihydroxyheptyl, and all isomers thereof , But is not limited thereto.

In one embodiment of the present invention, a linear or branched C _1-20 alkylamine compound which may be substituted, which may be reacted with the compound represented by Formula 2, a C _3-30 cycloalkylamine compound that may be substituted, And C _6-30 arylamine compounds which may be substituted are, for example, each independently selected from the group consisting of an amino group, a methylamino group, a dimethylamino group, an ethylamino group, a diethylamino group, a propylamino group, a dipropylamino group, a diisopropylamino group, Amino, diisobutylamino, di-tert-butylamino, dipentylamino, dihexylamino, diphenylamino, di-o- tolylamino, di- -Cyanophenyl) amino, and all isomers thereof, but is not limited thereto.

In one embodiment of the present invention, the compound represented by the general formula (2) is used in combination with at least one compound selected from the group consisting of phenol, phenylphenol, di-tert-butylphenol, hydroxy tert- butyl anisole, N-halosuccinimide, All of the isomers, and all of the isomers.

In one embodiment herein, the compound of Formula 2 is reacted with a compound selected from the group consisting of phenol, 2-phenylphenol, 2,4-di-tert-butylphenol, 4-hydroxy- Bromosuccinimide, hexylamine, and all of the isomers thereof.

In one embodiment of the present invention, the perylene-based compound prepared by the above-mentioned process comprises a compound consisting of a halogen, a cyanide salt, a phenol compound, a naphthol compound, an alcohol compound, a thiol compound, And then performing the reaction one to three times.

In one embodiment of the present invention, the phenol compound and the naphthol compound that can be reacted with the perylene compound are each independently selected from the group consisting of hydroxyphenyl, dihydroxyphenyl, methoxyphenyl, dimethoxyphenyl, Butoxyphenyl, diethoxyphenyl, diethoxyphenyl, triethoxyphenyl, propoxyphenyl, dipropoxyphenyl, isopropoxyphenyl, diisopropoxyphenyl, butoxyphenyl, hydroxyphenyl, dihydroxyphenyl , Naphthylaminophenyl, N-phenylaminophenyl, N- (o-tolyl) aminophenyl, N-phenylcarbamoylphenyl, N-methylcarboxamidophenyl, acetylaminophenyl, , (2-pyridyl) aminophenyl, (4-pyridyl) aminophenyl, (2-pyridyl) aminophenyl, -Pyrimidyl) aminophenyl, 4- (4-pyrimidyl) aminophenyl, and all isomers thereof. Gin may include is selected from the group, but is not limited to this.

In one embodiment of the present invention, the produced perylene-based reactive alcohol-based compound is, for example, independently selected from the group consisting of hydroxyethyl, hydroxypropyl, dihydroxypropyl, hydroxybutyl, dihydroxybutyl Dihydroxypentyl, dihydroxypentyl, hydroxyhexyl, dihydroxyhexyl, hydroxyheptyl, dihydroxyheptyl, and all isomers thereof, but is not limited thereto no.

In one embodiment of the present invention, the produced perylene-based reactive amine compound is, for example, each independently an amino group, methylamino, dimethylamino, ethylamino, diethylamino, Di-tert-butylamino, di-tert-butylamino, dipentylamino, dihexylamino, diphenylamino, di- p-tolylamino, di (4-cyanophenyl) amino, and all isomers thereof, but is not limited thereto.

In one embodiment of the present invention, the perylene compound thus prepared is reacted with a halogenated cyanide salt, phenol, phenylphenol, tert-butylphenol, di-tert-butylphenol, naphthol, methylpropanol, cyclohexanol, methoxythiophenol , Aniline, phenylboronic acid, cyanophenylboronic acid, naphthylboronic acid, and 2-methylpropylboronic acid, and all isomers thereof. One to three times.

In one embodiment of the present invention, the perylene-based compound prepared above is mixed with a compound selected from the group consisting of bromine, copper cyanide, phenol, 2-phenylphenol, 4-tert- butylphenol, 2-methylpropanol, cyclohexanol, 4-methoxythiophenol, aniline, phenylboronic acid, 4-cyanophenylboronic acid, 1-naphthylboronic acid, The addition of one selected from the group consisting of an isomer, a boronic acid, a boronic acid, a boronic acid, a boronic acid, a boronic acid, a boronic acid, a boronic acid, a boronic acid, a boronic acid, a boronic acid, a boronic acid, and all isomers thereof.

In one embodiment of the invention, the addition of a carbonate salt in some or all of the above reaction steps may additionally include, but is not limited to. The carbonate salt forms a basic atmosphere in each reaction step, for example an alkali metal carbonate such as sodium carbonate, potassium carbonate and cesium carbonate or an alkali metal hydroxide such as sodium hydroxide or potassium hydroxide for the same purpose But is not limited thereto.

In one embodiment herein, the reactions may include, but are not limited to, dissolving the reactants in an organic solvent, reacting, and then precipitating and filtering at room temperature.

In one embodiment herein, the reactions are conducted at ambient temperature to about 200 ° C, such as ambient temperature to about 200 ° C, ambient temperature to about 180 ° C, ambient temperature to about 160 ° C, ambient temperature to about 140 ° C, From about 70 ° C to about 180 ° C, from about 70 ° C to about 160 ° C, from about 70 ° C to about 140 ° C, from about 80 ° C to about 100 ° C, from ambient temperature to about 80 ° C, But is not limited to, at a temperature of about 130 캜, about 100 캜 to about 130 캜, about 110 캜 to about 130 캜, or about 120 캜 to about 130 캜.

In one embodiment of the present invention, the production method comprises a step of preparing a C _1-20 alkane compound, an optionally substituted C _6-30 cycloalkane compound, A C _6-30 aryl compound which may be substituted, a C _6-30 phenol compound which may be substituted, a C _1-20 alcohol compound which may be substituted, a C _1-20 alkylamine compound which may be substituted, A C _6-30 cycloalkylamine compound, a C _6-30 arylamine compound which may be substituted, or N-halosuccinimide, followed by reaction at a temperature of room temperature to about 200 캜, followed by precipitation and filtration at room temperature But are not limited thereto.

In one embodiment of the present invention, the production method is characterized in that a halogen, a cyanide salt, a phenol compound, a naphthol compound, an alcohol compound, a thiol compound, an amine compound and / or a salt thereof is added to the prepared perylene compound dissolved in an organic solvent Substitution of a substance selected from the group consisting of voronic acids, and the like, followed by reaction at a temperature ranging from room temperature to about 200 ° C., followed by precipitation and filtration at room temperature. However, the present invention is not limited thereto.

In one embodiment of the present invention, the organic solvent may be any organic solvent usable in the art without limitation, and examples thereof include dimethylformamide, tetrahydrofuran, methylene chloride, acetone, acetonitrile, dimethyl But are not limited to, sulfoxide, sulfoxide, hexamethylphosphoramide, pyridine, pyrimidine, imidazole, quinoline, isoquinoline, quinaldine, N-methylpiperidine, N-methylpiperidone, Acetamide, or tetramethylurea, but the present invention is not limited thereto. The organic solvent may be used in an amount of about 5 g to about 120 g per g of the perylene raw material, but is not limited thereto.

The third aspect of the present invention provides a fluorescent dye comprising a perylene-based compound according to the present invention.

In one embodiment of the present invention, the fluorescent dye may be a green fluorescent dye, but may not be limited thereto.

In one embodiment of the invention, the fluorescent dye may be used as a fluorescent dye for coloring high molecular weight organic and inorganic materials, especially plastic, paint, printing ink, inorganic-organic complexes, and oxide layer systems, . The fluorescent dyes can be used as intermediates for preparing dispersants, pigment additives for organic pigments and fluorescent dyes and pigment additives, or they can be used as ink-jet inks absorbing and / or releasing in the yellow region of the electromagnetic spectrum and dispersants for producing aqueous polymer dispersions , Pigment additives, and intermediates. The fluorescent dye can be used as a coloring component or a color correcting component of a luminescent color filter and a semipermeable color filter and a retroreflective element or as an electron emitting source of an electroluminescent device and a chemiluminescent device as a dispersant, But may not be limited thereto. In addition, the fluorescent dye may be used as an active component of a fluorescent conversion, a fluorescent photovoltaic collector, a bioluminescent array, and a photovoltaic generation, or as a laser dye, but may not be limited thereto.

In one embodiment of this application, the fluorescent dyes are used as fluorescent dyes for reactive coloration of high molecular weight organic and inorganic materials, especially plastics, paints, printing inks, inorganic-organic complexes, or as absorbing and / But not limited to, a fluorescent dye for producing a bleeding-resistant aqueous polymer dispersion. In addition, the fluorescent dye can be used as a coloring component or a color correcting component of a luminescent color filter and a semipermeable color filter and a retroreflective element, or as a migration-stable electron emitter of an electroluminescent device and a chemiluminescent device, But may not be limited thereto

The fluorescent dye according to the present aspect may be applied to all of the first and second aspects of the present invention, but the present invention is not limited thereto.

Hereinafter, the present invention will be described in more detail with reference to Examples, but the scope of the present invention is not limited by these Examples.

[Example]

Example 1

Synthesis of Intermediate 1

To a suspension of 1,6,7,12-tetrachlorophorylene tetracarboxylic acid dihydroidide (2.00 mmol) and 20 mL of water was added 10 mL of 1 M aqueous NaOH solution and stirred at 55 DEG C for 30 minutes . Bromine (1.0 mL) was added, and the mixture was stirred for 24 hours. The precipitate was filtered off and dried to give Intermediate Compound 1 (orange solid, yield: 87%).

- MALDI-TOF analysis: calculated molecular weight 705, measured molecular weight 704

- Melting point: 226 ℃

FTIR analysis (cm ^-1 ): (Ar CH) 3165, 3016, (Ar C = C) 1667, 1547, (C-Cl) 743, (C-Br) 651.

Synthesis of Compound 1

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 DEG C for 6 hours, the temperature was lowered to room temperature. The reaction product was added to 20 mL of 5% ammonium chloride aqueous solution, and the resulting precipitate was filtered and washed with 30 mL of water to obtain Compound 1 (yellow solid, yield: 68%).

- MALDI-TOF analysis: calculated molecular weight 758, measured molecular weight 756

- Melting point:> 350 ℃

- FTIR analysis (cm ^-1 ): (Ar CH) 3060, 2957, (Ar C = C) 1569, 1484, 1431, (COC) 1212, 1149, (C-Cl) 752, 713.

Synthesis of Compound 2

Compound 1 (1.00 mmol) was dissolved in 10 mL of dimethylformamide, followed by addition of 4-tert-butylphenol (5.00 mmol) and cesium carbonate (5.00 mmol). After stirring at 130 DEG C for 12 hours, the temperature was lowered to room temperature. The reaction product was added to 20 mL of 5% ammonium chloride aqueous solution, and the resulting precipitate was filtered and washed with 30 mL of water to obtain Compound 2 (yellow solid, yield: 38%).

- MALDI-TOF analysis: calculated molecular weight 1213, measured molecular weight 1212

- Melting point: 311 ℃

FTIR analysis (cm ^-1 ): (Ar CH) 2935, 2821, (Ar C = C) 1565, 1546, 1485, (C-CH ₃ ) 1367, (COC) 1255, 1216, 1167.

Example 2

Synthesis of Compound 3

Intermediate 1 (1.00 mmol) prepared as in Example 1 was dissolved in 10 mL of dimethylformamide, and then 2-phenylphenol (5.00 mmol) and potassium carbonate (5.00 mmol) were added. After stirring at 130 DEG C for 8 hours, the temperature was lowered to room temperature. The mixed solution was put into 20 mL of 5% ammonium chloride aqueous solution, and the resulting precipitate was filtered and washed with 30 mL of water to obtain Compound 3 (yellow solid, yield: 78%).

- MALDI-TOF analysis: calculated molecular weight 1063, measured molecular weight 1064

- Melting point:> 350 ℃

- FTIR analysis (cm ^-1 ) (Ar CH) 3052, 2995, (Ar C = C) 1572, 1521, 1491, (COC) 1256, 1205, (C-Cl) 769, 753.

Example 3

Synthesis of Compound 4

Intermediate 1 (1.00 mmol) prepared as in Example 1 was dissolved in 10 mL of dimethylformamide, and 2,4-ditetrabutylphenol (5.00 mmol) and potassium carbonate (5.00 mmol) were added. After stirring at 130 DEG C for 12 hours, the temperature was lowered to room temperature. The mixed solution was put into 20 mL of 5% aqueous ammonium chloride solution, and the resulting precipitate was filtered and washed with 30 mL of water to obtain Compound 4 (yellow solid, yield: 63%).

- MALDI-TOF analysis: calculated molecular weight 1207, measured molecular weight 1206

- Melting point:> 350 ℃

- FTIR analysis ^{(cm -1): (Ar CH} ) 2954, 2865, (Ar C = C) 1569, 1482, (C-CH 3) 1394, 1359, (COC) 1211, 1155, 1120, (C-Cl ) 769, 693.

Example 4

Synthesis of Compound 5

Intermediate 1 (1.00 mmol) prepared as in Example 1 was dissolved in 10 mL of dimethylformamide, followed by addition of 4-hydroxy-3-tetrabutyl anisole (5.00 mmol) and potassium carbonate (5.00 mmol) Respectively. After stirring at 130 DEG C for 12 hours, the temperature was lowered to room temperature. The mixed solution was put into 20 mL of 5% ammonium chloride aqueous solution, and the resulting precipitate was filtered and washed with 30 mL of water to obtain Compound 5 (yellow solid, yield: 42%)

- MALDI-TOF analysis: calculated molecular weight 1103, measured molecular weight 1103

- Melting point:> 350 ℃

- FTIR analysis ^{(cm -1): (Ar CH} ) 3012, 2965, (Ar C = C) 1502, 1499, (C-CH 3) 1386, 1348, (COC) 1202, 1185, 1166, 1058 (C- Cl) 715.

Example 5

Synthesis of Compound 6

Intermediate 1 (1.00 mmol) prepared as in Example 1 was dissolved in 10 mL of dimethylformamide, and then hexylamine (5.00 mmol) and triethylamine (5.00 mmol) were added. After stirring at 130 DEG C for 12 hours, the temperature was lowered to room temperature. The mixed solution was put into 20 mL of 5% ammonium chloride aqueous solution, and the resulting precipitate was filtered and washed with 30 mL of water to obtain Compound 6 (orange solid, yield: 76%).

- MALDI-TOF analysis: calculated molecular weight 786, measured molecular weight 785

- Melting point:> 350 ℃

FTIR analysis (cm ^-1 ): (NH) 3233, (CH ₂ ) 3211, (Ar CH) 3021, 2915, (Ar C = C) 1565, 1501, 1486 (C-CH ₃ ) 1415, 1392, 1331 , (COC) 185 1138 (C-Cl) 775.

Example 6

Synthesis of Compound 7

Compound 1 (1.00 mmol) of Example 1 was dissolved in 10 mL of dimethylformamide, and phenol (5.00 mmol) and potassium carbonate (5.00 mmol) were added. After stirring at 130 ° C for 8 hours, the temperature was lowered to room temperature. The reaction product was added to 20 mL of 5% ammonium chloride aqueous solution, and the resulting precipitate was filtered and washed with 30 mL of water to obtain Compound 7 (yellow solid, yield: 42%).

- MALDI-TOF analysis: calculated molecular weight 989, measured molecular weight 989

- Melting point: 263 ℃

- FTIR analysis ^{(cm -1): (Ar CH} ) 2975, 2844, (Ar C = C) 1577, 1465, (C-CH 3) 1301, 1287, (COC) 1212, 1192.

Example 7

Synthesis of Compound 8

Compound 1 (1.00 mmol) in Example 1 was dissolved in 10 mL of dimethylformamide, followed by addition of cyclohexanol (5.00 mmol) and cesium carbonate (5.00 mmol). After stirring at 130 DEG C for 12 hours, the temperature was lowered to room temperature. A mixed solution was added to 20 mL of 5% ammonium chloride aqueous solution, and the resulting precipitate was filtered and washed with 30 mL of water to obtain Compound 8 (yellow solid, yield: 42%).

- MALDI-TOF analysis: calculated molecular weight 1013, measured molecular weight 1012

- Melting point: 212 ℃

- FTIR analysis ^{(cm -1): (Ar CH} ) 3061, 2931, (Ar C = C) 1575, 1485, (COC) 1206, 1162, (-CH 2) 812, 747.

Example 8

Synthesis of Compound 9

Compound 1 (1.00 mmol) of Example 1 was dissolved in 10 mL of dimethylformamide, and then 2,4-diisopropylbutylphenol (5.00 mmol) and cesium carbonate (5.00 mmol) were added. After stirring at 130 DEG C for 12 hours, the temperature was lowered to room temperature. The reaction product was added to 20 mL of 5% ammonium chloride aqueous solution, and the resulting precipitate was filtered and washed with 30 mL of water to obtain Compound 9 (yellow solid, yield: 24%).

- MALDI-TOF analysis: calculated molecular weight 1437, measured molecular weight 1436

- Melting point: 285 ℃

- FTIR analysis ^{(cm -1): (Ar CH} ) 2954, 2866, (Ar C = C) 1584, 1487, (C-CH 3) 1372, 1303, (COC) 1209, 1121.

Example 9

Synthesis of compound 10.

Diisobutyl perylene-3,9-dicarboxylate (2.00 mmol) was dissolved in 10 mL of dimethylformamide, N-bromosuccinimide (4.20 mmol) was added, and the mixture was stirred at 80 ° C for 6 hours The temperature was then lowered to room temperature. Pour the mixture into 30 mL of methanol and stir for 30 minutes. The resulting crystals were filtered and washed with water and 20 mL of methanol, respectively. After drying, Compound 10 (pale orange solid, yield: 83%) was obtained.

- MALDI-TOF analysis: calculated molecular weight 610, measured molecular weight 610

- Melting point: 351 ℃

- FTIR analysis (cm ^-1 ): (Ar CH) 2967, (C = O) 1717, (ArC = C) 1581,1502,1465, (C-CH3) 1393,1302, (COC) 1155,1132, (CH) 760.

Synthesis of Compound 11

The compound 10 (1.00 mmol) was dissolved in 5 mL of tetrahydrofuran, followed by stirring 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 the reaction was carried out at 70 ° C for 12 hours. After lowering the temperature, the water layer was removed with a separating funnel and poured into 10 mL of methanol to produce crystals. The resulting crystals were filtered and washed with 20 mL of water and methanol, respectively, to obtain Compound 11 (light yellow solid, yield: 30%).

- MALDI-TOF analysis: calculated molecular weight 604, measured molecular weight 604

- Melting point: 395 ℃

- FTIR analysis (cm ^-1 ): (Ar CH) 3050, 2959, (C = O) 1708, (Ar C = C) 1584, 1515, (C- ) 759, 700.

Synthesis of Compound 12

Compound 11 (1.00 mmol) was dissolved in 10 mL of methylene chloride, followed by addition of bromine (2.5 mmol). After stirring at room temperature for 6 hours, the mixture was poured into 30 ml of methanol and stirred for 1 hour to produce crystals. The resulting crystals were filtered and washed with 50 mL of methanol to give compound 12 (orange solid, yield: 70%).

- MALDI-TOF analysis: calculated molecular weight 762, measured molecular weight 761

- Melting point: 345 ℃

- FTIR analysis (cm ^-1 ): (Ar CH) 3052, 2955, (C = O) 1718, (Ar C = C) 1543, 1487, (C-CH 3) 1368, (COC) 1194, ) 760, 700.

Synthesis of Compound 13

Compound 12 (1.00 mmol) was dissolved in 10 mL of methylene chloride, followed by addition of copper cyanide (4 mmol). After stirring at 150 ° C for 5 hours, the temperature was lowered and poured into 30 mL of water to produce crystals. The resulting crystals were filtered and washed with 50 mL of methanol to obtain Compound 13 (red solid, yield: 65%).

- MALDI-TOF analysis: calculated molecular weight 654, measured molecular weight 654

- Melting point: 420 ℃

- FTIR analysis (cm ^-1 ): (Ar CH) 3056, 2957, (C = N) 2214, (C = O) 1720, (Ar C = C) 1589, 1489, 1468, (C- (COC) 1192, 1151, (CH) 763, 703.

Example 10

Synthesis of Compound 14

Compound 10 (1.00 mmol) in Example 9 was dissolved in 10 mL of methylene chloride, followed by addition of bromine (3 mmol), and the mixture was stirred at room temperature. After 6 hours, it was poured into 50 mL of methanol to form crystals, which were then 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

- Melting point: 321 ℃

- FTIR analysis (cm ^-1 ): (Ar CH) 2966, (C = O) 1717, (Ar C = C) 1579, 1513, 1452, (C- (CH) 758.

Synthesis of Compound (15)

The compound 14 (1.00 mmol) was dissolved in 5 mL of tetrahydrofuran, followed by stirring 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 the reaction was carried out at 70 ° C for 12 hours. After lowering the temperature, the water layer was removed with a separating funnel and poured into 10 mL of methanol to produce crystals. The resulting crystals were filtered and washed with 20 mL of water and methanol, respectively, to obtain Compound 15 (light orange solid, yield: 22%).

- MALDI-TOF analysis: calculated molecular weight 756, measured molecular weight 756

- Melting point: 363 ℃

- FTIR analysis (cm ^-1 ): (Ar CH) 3055, 2958, (C = O) 1717, (ArC.dbd.C) 1598, (C-CH3) 1368, 1256, (COC) 1190, ) 756, 698.

Example 11

Synthesis of Compound 16

Compound 14 (1.00 mmol) in Example 10 was dissolved in 10 mL of dimethylformamide, and phenol (6.00 mmol) and potassium carbonate (6.00 mmol) were added. After stirring at 130 DEG C for 12 hours, the temperature was lowered to room temperature. A mixed solution was added to 20 mL of 5% ammonium chloride aqueous solution, and the resulting precipitate was filtered and washed with 30 mL of water to obtain Compound 16 (yellow solid, yield: 63%).

- MALDI-TOF analysis: calculated molecular weight 820, measured molecular weight 820

- Melting point: 353 ℃

- FTIR analysis (cm ^-1 ): (Ar CH) 3050, 2960, (C = O) 1717, (ArC = C) 1583, 1502, (C- (CH) 760.

Example 12

Synthesis of Compound 17

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 DEG C for 8 hours, the temperature was lowered and poured into 30 mL of water to produce crystals. The resulting crystals were filtered and washed with 50 mL of methanol to obtain Compound 17 (red solid, yield: 72%).

- MALDI-TOF analysis: calculated molecular weight 554, measured molecular weight 554

- Melting point: 332 ℃

FTIR analysis (cm ^-1 ): (Ar CH) 3050, 2963, (C = N) 2211 (C = O) 1715, (Ar C = C) 1611, 1593, (C- COC) 1152, 1129, (CH) 760,681.

Example 13

Synthesis of compound 18

Compound 10 (1.00 mmol) in Example 9 was dissolved in 5 mL of tetrahydrofuran, and then stirred with 3 mL of water, 2-methylpropylboronic acid (4.00 mmol) and sodium carbonate (4.00 mmol) . Pd (PPh ₃ ) ₄ (0.01 mmol) was added as a catalyst, and the reaction was carried out at 70 ° C for 24 hours. After lowering the temperature, the water layer was removed with a separating funnel and poured into 10 mL of methanol to produce crystals. The resulting crystals were filtered and washed with 20 mL of water and methanol, respectively, to obtain Compound 18 (light yellow solid, yield: 20%).

- MALDI-TOF analysis: calculated molecular weight 564, measured molecular weight 564

- Melting point: 395 ℃

- FTIR analysis (cm ^-1 ): (Ar CH) 3050, 2972, (C = O) 1717, (Ar C = C) 1603, 1578, (C- (CH) 760, 700.

Synthesis of Compound 19

Compound 18 (1.00 mmol) was dissolved in 10 mL of methylene chloride, and bromine (3 mmol) was added. After stirring at room temperature for 6 hours, the mixture was poured into 30 mL of methanol and stirred for 1 hour to produce crystals. The resulting crystals were filtered and washed with 50 mL of methanol to obtain Compound 19 (dark yellow solid, yield: 59%).

- MALDI-TOF analysis: calculated molecular weight 722, measured molecular weight 721

- Melting point: 345 ℃

- FTIR analysis (cm ^-1 ): (Ar CH) 3057, 2959, (C = O) 1714, (Ar C = C) 1640, 1598, (C-CH 3) 1369, 1255, (COC) 1190, (CH) 755, 698.

Synthesis of Compound 20

The compound 19 (1.00 mmol) was dissolved in 5 mL of tetrahydrofuran, followed by stirring 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 the reaction was carried out at 70 ° C for 12 hours. After lowering the temperature, the water layer was removed with a separating funnel and poured into 10 mL of methanol to produce crystals. The resulting crystals were filtered and washed with 20 mL of water and methanol, respectively, to obtain Compound 20 (orange solid, yield: 23%).

- MALDI-TOF analysis: calculated molecular weight 716, measured molecular weight 716

- Melting point: 377 ℃

- FTIR analysis (cm ^-1 ): (Ar CH) 3060, 2979, (C = O) 1717, (Ar C = C) 1652, 1597, (C- (CH) 761, 698.

Example 14

Synthesis of Compound 21

Compound 10 (1.00 mmol) in Example 9 was dissolved in 10 mL of dimethylformamide, stirred with phenol (3.00 mmol) and potassium carbonate (3.00 mmol) at 130 ° C for 6 hours, Lowered. The reaction product was added to 20 mL of a 5% ammonium chloride aqueous solution, and the resulting precipitate was filtered and washed with 30 mL of water to obtain a compound 21 (yellow solid, yield: 68%).

- MALDI-TOF analysis: calculated molecular weight 636, measured molecular weight 638

- Melting point: 373 ℃

- FTIR analysis (cm ^-1 ): (Ar CH) 3049, 2959, (C = O) 1717, (Ar C = C) 1583, 1502, 1489, (C- 1132, (CH) 794, 760.

Example 15

Synthesis of Compound 22

Compound 10 (1.00 mmol) in Example 9 was dissolved in 10 mL of dimethylformamide, followed by addition of 2-phenylphenol (5.00 mmol) and cesium carbonate (5.00 mmol). After stirring at 130 DEG C for 8 hours, the temperature was lowered to room temperature. A mixed solution was added to 20 mL of 5% ammonium chloride aqueous solution, and the resulting precipitate was filtered and washed with 30 mL of water to obtain Compound 22 (yellow solid, yield: 52%).

- MALDI-TOF analysis: calculated molecular weight 788, measured molecular weight 790

- Melting point: 369 ℃

- FTIR analysis (cm ^-1 ): (Ar CH) 3054, 2958, (C = O) 1717, (Ar C = C) 1581, 1502, 1467, (C- 1132, (CH) 759, 698.

Example 16

Synthesis of Compound 23

Compound 10 (1.00 mmol) in Example 9 was dissolved in 10 mL of dimethylformamide, and aniline (3.00 mmol) and cesium carbonate (3.00 mmol) were added. After stirring at 130 DEG C for 12 hours, the temperature was lowered to room temperature. A mixed solution was added to 20 mL of a 5% ammonium chloride aqueous solution, and the resulting precipitate was filtered and washed with 30 mL of water to obtain a compound 23 (yellow solid, yield: 48%).

- MALDI-TOF analysis: calculated molecular weight 636, measured molecular weight 636

- Melting point: 359 ℃

FTIR analysis (cm ^-1 ): (Ar CH) 3050, 2959, 2873 (C = O) 1717, (Ar C = C) 1581, 1502, 1466, (C- , 1132, (CH) 760.

Example 17

Synthesis of Compound 24

Compound 10 (1.00 mmol) in Example 9 was dissolved in 10 mL of dimethylformamide, and then 2-naphthol (3.00 mmol) and cesium carbonate (3.00 mmol) were added. After stirring at 130 DEG C for 10 hours, the temperature was lowered to room temperature. A mixed solution was added to 20 mL of 5% ammonium chloride aqueous solution, and the resulting precipitate was filtered and washed with 30 mL of water to obtain Compound 24 (a dark yellow solid, yield: 62%).

- MALDI-TOF analysis: calculated molecular weight 736, measured molecular weight 737

- Melting point: 351 ℃

- FTIR analysis (cm ^-1 ): (Ar CH) 3050, 2956, (C = O) 1707, (Ar C = C) 1584, 1515, 1463, (C- (CH) 758, 700.

Example 18

Synthesis of Compound 25

Compound 10 (1.00 mmol) in Example 9 was dissolved in 10 mL of dimethylformamide, and then 4-tert-butylphenol (3.00 mmol) and potassium carbonate (3.00 mmol) were added. After stirring at 130 DEG C for 6 hours, the temperature was lowered to room temperature. A mixed solution was added to 20 mL of 5% ammonium chloride aqueous solution, and the resulting precipitate was filtered and 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

- Melting point: 373 ℃

- FTIR analysis (cm ^-1 ): (Ar CH) 3054, 2958, (C = O) 1716, (Ar C = C) 1584, 1537, 1495, (C- (CH) 748, 692.

Example 19

Synthesis of Compound 26

Compound 10 (1.00 mmol) in Example 9 was dissolved in 10 mL of tetrahydrofuran, followed by stirring with 3 mL of water, 1-naphthylboronic acid (4.00 mmol) and sodium carbonate (4.00 mmol). Pd (PPh ₃ ) ₄ (0.01 mmol) was added as a catalyst, and the reaction was carried out at 70 ° C for 8 hours. The temperature was lowered, the water layer was removed with a separating funnel, and the solution was poured into 10 mL of methanol to form crystals. The resulting crystals were filtered and washed with 20 mL of water and methanol, respectively, to obtain 26 (light yellow solid, yield: 24%).

- MALDI-TOF analysis: calculated molecular weight 704, measured molecular weight 704

- melting point: 382 ℃

- FTIR analysis (cm ^-1 ): (Ar CH) 3052, (C = O) 1715, (Ar C = C) 1593, 1522, 1502, (C- (CH) 760, 699.

Example 20

Synthesis of Compound 27

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 DEG C for 24 hours, the temperature was lowered to room temperature. A mixed solution was added to 20 mL of 5% ammonium chloride aqueous solution, and the resulting precipitate was filtered and washed with 30 mL of water to obtain Compound 27 (yellow solid, yield: 38%).

- MALDI-TOF analysis: calculated molecular weight 596, measured molecular weight 596

- Melting point: 348 ℃

- FTIR analysis (cm ^-1 ): (Ar CH) 3050, 2959, (C = O) 1717, (ArC = C) 1581, 1502, (C-CH3) 1365,1302, (COC) 1155, 1132, (CH) 817, 760, 696.

Example 21

Synthesis of Compound 28

Compound 10 (1.00 mmol) in Example 9 was dissolved in 10 mL of tetrahydrofuran, followed by stirring with 3 mL of water, 4-cyanophenylboronic acid (4.00 mmol) and sodium carbonate (4.00 mmol). Pd (PPh ₃ ) ₄ (0.01 mmol) was added as a catalyst, and the reaction was carried out at 70 ° C for 12 hours. After lowering the temperature, remove the water layer with a separating funnel and pour into 10 mL of methanol to form crystals. The resulting crystals were filtered and washed with 20 mL of water and methanol, respectively, to obtain Compound 28 (light yellow solid, yield: 25%).

- MALDI-TOF analysis: calculated molecular weight 654, measured molecular weight 654

- Melting point: 383 ℃

FTIR analysis (cm ^-1 ): (Ar CH) 3042, 2961, 2880, (C = N) 2221 (C = O) 1707, (Ar C = C) 1602, 1589, (C- , (COC) 1181, 1152, 1129, (CH) 767, 671.

Example 22

Synthesis of Compound 29

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 DEG C for 24 hours, the temperature was lowered to room temperature. A mixed solution was added to 20 mL of 5% ammonium chloride aqueous solution, and the resulting precipitate was filtered and washed with 30 mL of water to obtain 29 (orange solid, yield: 63%).

- MALDI-TOF analysis: calculated molecular weight 728, measured molecular weight 728

- Melting point: 328 ℃

- FTIR analysis (cm ^-1 ): (Ar CH) 3065, 2983, (C = O) 1717, (Ar C = C) 1601, 1581, (C-CH 3) 1316, 758.

Experimental Example  One

Propylene glycol monomethyl ether acetate was added to each of the perylene-based compounds to confirm absorption and fluorescence of the synthesized perylene-based compounds 1 to 29, and the mixture was stirred for 10 minutes. Thereafter, propylene glycol monomethyl ether acetate was further added, and the concentration was diluted to 20 ppm. Then, a UV / Vis / NIR spectrophotometer (UV3600-shimadzu) and a spectrofluorophotometer (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 (Λmax), the maximum emission wavelength (Λ emission) and the molar extinction coefficient (ε) for the dye compounds prepared as in the above Examples and Comparative Example as Lumogen 083. In Table 1 below, Lumogen 083 was not dissolved and could not exhibit molar extinction coefficient values. As can be seen from the following Table 1, Lumogen 083, which is a comparative example, is low in solubility and does not dissolve in a solvent. On the other hand, it is confirmed that the dye compounds according to the present examples show excellent solubility. In the above experiment, it was confirmed that the compounds according to the present invention exhibit spectral characteristics similar to those of the comparative examples and have a much improved solubility as compared with the comparative examples.

[Table 1]

FIG. 1 shows the maximum absorption wavelength (solid line) and the maximum emission wavelength (dotted line) of the compounds 2, 7 and 9, which are compounds having high molarities and high solubility in organic solvents among the dye compounds according to the present example.

Experimental Example  2

The solubility of propylene glycol monomethyl ether acetate (PGMEA) and methyl ethyl ketone (MEK) was evaluated for the perylene-based compounds 1 to 12 prepared as in the above examples.

The compound and solvent were mixed at a concentration of about 3% to about 5% in a 25 mL vial bottle, the vial bottle was completely sealed, and shaken for 15 minutes. After 30 minutes, the presence or absence of the liquid precipitate was visually observed. When the precipitate was confirmed, it was judged that the solubility was poor. As a criterion of solubility,?,?,?, And? Were shown as?,?, And?, Respectively, when the solubility was 3% or less and 3% or less, respectively. As can be seen from the following Table 2, it was confirmed that the solubility of the perylene compound of the present invention is superior to that of the conventional fluorescent dye.

[Table 2]

It will be understood by those of ordinary skill in the art that the foregoing description of the embodiments is for illustrative purposes and that those skilled in the art can easily modify the invention without departing from the spirit or essential characteristics thereof. It is therefore to be understood that the above-described embodiments are illustrative in all aspects and not restrictive. For example, each component described as a single entity may be distributed and implemented, and components described as being distributed may also be implemented in a combined form.

The scope of the present invention is defined by the appended claims rather than the detailed description, and all changes or modifications derived from the meaning and scope of the claims and their equivalents should be interpreted as being included in the scope of the present invention .

Claims (12)

A perylene compound comprising any one of the following compounds:

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delete delete delete delete delete delete The compound represented by the following formula 2 is dissolved in an organic solvent and then reacted with an organic solvent such as phenol, phenyl phenol, di-tert-butyl phenol, hydroxy tert-butyl anisole, N-halosuccinimide, ≪ RTI ID = 0.0 >
A process for producing the perylene compound according to claim 1, comprising:
(2)

In Formula 2,
R ₅ to R ₈ are each independently hydrogen, halogen or a linear or branched C _2-10 alkylcarboxyl group. The compound represented by the following formula 2 is dissolved in an organic solvent and then reacted with an organic solvent such as phenol, phenyl phenol, di-tert-butyl phenol, hydroxy tert-butyl anisole, N-halosuccinimide, With a compound selected from the group consisting of:
(2)

In Formula 2,
R ₅ to R ₈ are each independently hydrogen, halogen or a linear or branched C _2-10 alkylcarboxyl group;
The perylene compound thus prepared is dissolved in an organic solvent and then reacted with an organic solvent such as halogen, cyanide salt, phenol, phenylphenol, tert-butylphenol, di-tert-butylphenol, naphthol, methylpropanol, cyclohexanol, methoxythiophenol, , the step of phenyl Boro Nick Acid, cyanophenyl beam Nick Acid, naphthyl Boro Nick Acid, and 2-methylpropyl Boro Nick Acid, and their addition hayeoseo the reaction being selected is a material from the group consisting of all isomers Performing one to three times
Wherein the perylene-based compound is a perylene-based compound. 10. The method according to claim 8 or 9,
The method of producing a perylene compound according to Claim 1, further comprising adding a carbonate salt in some or all of the above reaction steps. 10. The method according to claim 8 or 9,
The method for producing a perylene compound according to claim 1, wherein the reactions include dissolving the reactants in an organic solvent, reacting them, and then precipitating and filtering at room temperature. A fluorescent dye comprising the perylene compound of claim 1.

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