KR102074546B1 - Compound containing nitrogen and color conversion film comprising the same - Google Patents

Abstract

The present specification relates to a nitrogen compound, a color conversion film, a backlight unit, and a display device including the same.

Description

Nitrogen-containing ring compound and color conversion film containing same {COMPOUND CONTAINING NITROGEN AND COLOR CONVERSION FILM COMPRISING THE SAME}

The present specification relates to a nitrogen-containing ring compound, a color conversion film, a backlight unit, and a display device including the same. This application claims the benefit of the filing date of Korean Patent Application No. 10-2015-0137062 filed with the Korea Patent Office on September 25, 2015, the contents of which are incorporated herein in its entirety.

Conventional light emitting diodes (LEDs) are obtained by mixing a green phosphor and a red phosphor into a blue light emitting diode or by mixing a yellow phosphor and a blue-green phosphor into a UV light emitting light emitting diode. However, this method is difficult to control the color and thus poor color rendering. Therefore, color reproduction rate falls.

In order to overcome such a drop in color reproduction and reduce production costs, a method of implementing green and red by quantizing quantum dots and combining them with a blue LED has been recently attempted. However, cadmium-based quantum dots have a safety problem, and other quantum dots are significantly less efficient than cadmium-based. In addition, the quantum dot has a disadvantage in that the stability of oxygen and water is poor and its performance is significantly reduced when aggregated. In addition, the production cost of the quantum dot is difficult to maintain a constant size is high.

Korean Patent Publication No. 2000-0011622

The present specification provides a nitrogen-containing ring compound, a color conversion film, a backlight unit, and a display device including the same.

According to an exemplary embodiment of the present specification, to provide a compound represented by the formula (1).

[Formula 1]

In Chemical Formula 1,

X1 and X2 are the same as or different from each other, and are each independently C or S (= 0),

Y1 and Y2 are the same as or different from each other, and are each independently NH or a direct bond,

L1 and L2 are the same as or different from each other, and each independently an alkylene group or a direct bond,

R1 to R11 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; Nitrile group; Nitro group; Hydroxyl group; Carboxy group (-COOH); Ether group; Ester group; Imide group; Imide group; Amide group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkyl thioxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted aryl sulfoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl phosphine group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, n and m are each 1 or 2,

Z1 and Z2 are the same as or different from each other, and each independently halogen; Nitrile group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Or a substituted or unsubstituted aryl group, or Z1 and Z2 combine with each other to form a substituted or unsubstituted ring.

According to yet an embodiment of the present disclosure, the resin matrix; And it provides a color conversion film comprising a compound represented by the formula (1) dispersed in the resin matrix.

According to another exemplary embodiment of the present specification, a backlight unit including the color conversion film is provided.

According to another exemplary embodiment of the present specification, a display device including the backlight unit is provided.

The compound according to an exemplary embodiment of the present specification is not only high fluorescence efficiency, but also a green light emitting material having excellent light resistance. Therefore, by using the compound described herein as a fluorescent material of the color conversion film, it is possible to provide a color conversion film excellent in brightness and color reproducibility and excellent in light resistance.

1 is a schematic diagram applying a color conversion film according to one embodiment of the present specification to a backlight.
2 is a graph comparing optical properties by applying the films prepared in Comparative Examples and Examples 1 to 5 of the present specification to a backlight.

Hereinafter, this specification is demonstrated in detail.

According to an exemplary embodiment of the present specification, it provides a compound represented by the formula (1).

The compound according to one embodiment of the present specification may be used as a green light emitting material. In particular, when the substituent has a substituent at position 8 of the core structure, that is, a -C (= 0) OR8 or -C (= 0) OR9 substituent, light resistance is greatly improved.

In the present specification, when a part "includes" a certain component, this means that it may further include other components, without excluding other components, unless specifically stated otherwise.

In this specification, when a member is located "on" another member, this includes not only when one member is in contact with another member but also when another member exists between the two members.

Examples of substituents in the present specification are described below, but are not limited thereto.

The term "substituted" means that a hydrogen atom bonded to a carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited to a position where the hydrogen atom is substituted, that is, a position where a substituent can be substituted, if two or more substituted , Two or more substituents may be the same or different from each other.

As used herein, the term "substituted or unsubstituted" is deuterium; Halogen group; Nitrile group; Nitro group; Imide group; Amide group; Carbonyl group; Carboxy group (-COOH); Ether group; Ester group; Hydroxyl group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkyl thioxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted aryl sulfoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl phosphine group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; And it is substituted with one or two or more substituents selected from the group consisting of a substituted or unsubstituted heterocyclic group, or two or more of the substituents exemplified above are substituted with a substituent, or means that do not have any substituents. For example, "a substituent to which two or more substituents are linked" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent to which two phenyl groups are linked.

는 다른 치환기 또는 결합부에 결합되는 부위를 의미한다.In the present specification,

Means a site bonded to another substituent or binding moiety.

In the present specification, the halogen group may be fluorine, chlorine, bromine or iodine.

In this specification, although carbon number of an imide group is not specifically limited, It is preferable that it is C1-C30. Specifically, it may be a compound having a structure as follows, but is not limited thereto.

In the present specification, the amide group may be substituted with nitrogen of the amide group is hydrogen, a linear, branched or cyclic alkyl group having 1 to 30 carbon atoms or an aryl group having 6 to 30 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.

Although carbon number of a carbonyl group in this specification is not specifically limited, It is preferable that it is C1-C30. Specifically, it may be a compound having a structure as follows, but is not limited thereto.

In the present specification, the ether group is a linear, branched or cyclic alkyl group of oxygen of ether having 1 to 25 carbon atoms; Or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

In the present specification, the ester group is a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms of oxygen of the ester group; Or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.

In the present specification, the alkyl group may be linear or branched chain, carbon number is not particularly limited, but is preferably 1 to 30. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl , Isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n -Heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethyl Heptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like, but is not limited thereto.

In the present specification, the cycloalkyl group is not particularly limited, but preferably 3 to 30 carbon atoms, specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but are not limited thereto. It is not.

In the present specification, the alkoxy group may be linear, branched or cyclic. Although carbon number of an alkoxy group is not specifically limited, It is preferable that it is C1-C30. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, Isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy and the like It may be, but is not limited to such.

In the present specification, the amine group is -NH ₂ ; Alkylamine group; N-arylalkylamine group; Arylamine group; N-aryl heteroaryl amine group; It may be selected from the group consisting of an N-alkylheteroarylamine group and a heteroarylamine group, and carbon number is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, and 9-methyl-anthracenylamine group. , Diphenylamine group, N-phenylnaphthylamine group, ditolylamine group, N-phenyltolylamine group, triphenylamine group and the like, but is not limited thereto.

In the present specification, the N-alkylarylamineamine group means an amine group in which an alkyl group and an aryl group are substituted for N of the amine group.

In the present specification, the N-arylheteroarylamine group means an amine group in which an aryl group and a heteroaryl group are substituted for N in the amine group.

In the present specification, the N-alkylheteroarylamine group means an amine group in which an alkyl group and a heteroarylamine group are substituted for N of the amine group.

In the present specification, the alkyl group in the alkylamine group, the N-alkylarylamine group, the alkylthioxy group, the alkyl sulfoxy group, and the N-alkylheteroarylamine group is the same as the example of the alkyl group described above. Specifically, alkyl thioxy groups include methyl thioxy group, ethyl thioxy group, tert-butyl thioxy group, hexyl thioxy group and octyl thioxy group, and the alkyl sulfoxy group includes mesyl, ethyl sulfoxy group, propyl sulfoxy group and butyl sulfoxy group. Etc., but is not limited thereto.

In the present specification, the alkenyl group may be linear or branched chain, carbon number is not particularly limited, but is preferably 2 to 30. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2- ( Naphthyl-1-yl) vinyl-1-yl, 2,2-bis (diphenyl-1-yl) vinyl-1-yl, stilbenyl group, styrenyl group and the like, but are not limited thereto.

In the present specification, specifically, the silyl group includes trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like. However, the present invention is not limited thereto.

In the present specification, the boron group may be -BR ₁₀₀ R ₁₀₁ , wherein R ₁₀₀ and R ₁₀₁ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; Nitrile group; A substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms; Substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And it may be selected from the group consisting of a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

In the present specification, the phosphine oxide group specifically includes a diphenylphosphine oxide group, dinaphthylphosphine oxide, and the like, but is not limited thereto.

In the present specification, the aryl group is not particularly limited, but preferably has 6 to 30 carbon atoms, and the aryl group may be monocyclic or polycyclic.

When the aryl group is a monocyclic aryl group, carbon number is not particularly limited, but is preferably 6 to 30 carbon atoms. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto.

Carbon number is not particularly limited when the aryl group is a polycyclic aryl group. It is preferable that it is C10-30. Specifically, the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, triphenyl group, pyrenyl group, perrylenyl group, chrysenyl group, fluorenyl group, etc., but is not limited thereto.

In the present specification, the fluorenyl group may be substituted, and adjacent substituents may combine with each other to form a ring.

,

,

및

등이 될 수 있다. 다만, 이에 한정되는 것은 아니다.When the fluorenyl group is substituted,

,

,

And

And so on. However, the present invention is not limited thereto.

In the present specification, the aryl group in the aryloxy group, arylthioxy group, aryl sulfoxy group, N-arylalkylamine group, N-arylheteroarylamine group, and arylphosphine group is the same as the examples of the aryl group described above. Specifically, as the aryloxy group, phenoxy group, p-tolyloxy group, m- toryloxy group, 3,5-dimethyl-phenoxy group, 2,4,6-trimethylphenoxy group, p-tert-butylphenoxy group, 3- Biphenyloxy group, 4-biphenyloxy group, 1-naphthyloxy group, 2-naphthyloxy group, 4-methyl-1- naphthyloxy group, 5-methyl-2- naphthyloxy group, 1- anthryloxy group , 2-anthryloxy group, 9-anthryloxy group, 1-phenanthryloxy group, 3-phenanthryloxy group, 9-phenanthryloxy group, and the like. Examples of the arylthioxy group include a phenylthioxy group and 2- The methylphenyl thioxy group, 4-tert- butylphenyl thioxy group, etc. are mentioned, An aryl sulfoxy group includes a benzene sulfoxy group, p-toluene sulfoxy group, etc., but is not limited to this.

In the present specification, examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group. The aryl group in the arylamine group may be a monocyclic aryl group, may be a polycyclic aryl group. The arylamine group including two or more aryl groups may simultaneously include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group. For example, the aryl group in the arylamine group may be selected from the examples of the aryl group described above.

In the present specification, the heteroaryl group includes one or more atoms other than carbon and heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se, and S, and the like. Although carbon number is not particularly limited, it is preferably 2 to 30 carbon atoms, the heteroaryl group may be monocyclic or polycyclic. Examples of the heterocyclic group are thiophene group, furanyl group, pyrrole group, imidazolyl group, thiazolyl group, oxazolyl group, oxadiazolyl group, pyridyl group, bipyridyl group, pyrimidyl group, triazinyl group, tria Sleepyl group, acridil group, pyridazinyl group, pyrazinyl group, quinolinyl group, quinazolinyl group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group , Isoquinolinyl group, indolyl group, carbazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiazolyl group, benzocarbazolyl group, benzothiophene group, dibenzothiophene group, benzofuranyl group, pe Nanthrolinyl group (phenanthroline), thiazolyl group, isooxazolyl group, oxadiazolyl group, thiadiazolyl group, benzothiazolyl group, phenothiazinyl group and dibenzofuranyl group and the like, but are not limited thereto.

In the present specification, examples of the heteroarylamine group include a substituted or unsubstituted monoheteroarylamine group, a substituted or unsubstituted diheteroarylamine group, or a substituted or unsubstituted triheteroarylamine group. The heteroarylamine group including two or more heteroaryl groups may include a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a monocyclic heteroaryl group and a polycyclic heteroaryl group at the same time. For example, the heteroaryl group in the heteroarylamine group may be selected from the examples of the heteroaryl group described above.

In the present specification, examples of the heteroaryl group in the N-arylheteroarylamine group and the N-alkylheteroarylamine group are the same as the examples of the heteroaryl group described above.

In the present specification, the heterocyclic group may be monocyclic or polycyclic, may be aromatic, aliphatic or a condensed ring of aromatic and aliphatic, and may be selected from examples of the heteroaryl group.

In the present specification, the description of the alkyl group described above may be applied except that the alkylene group is a divalent group.

According to an exemplary embodiment of the present specification, the compound of Formula 1 may be represented by one of the following formula (2 to 4).

[Formula 2]

[Formula 3]

[Formula 4]

In Chemical Formulas 2 to 4, the definition of the substituent is as defined in Chemical Formula 1.

According to an exemplary embodiment of the present disclosure, R1 to R5 is hydrogen or deuterium.

According to an exemplary embodiment of the present disclosure, R6 to R9 is hydrogen; heavy hydrogen; Or a substituted or unsubstituted alkyl group.

According to an exemplary embodiment of the present specification, R6 to R9 is an alkyl group having 1 to 6 carbon atoms.

According to an exemplary embodiment of the present specification, L1 and L2 are a direct bond or an alkylene group having 1 to 6 carbon atoms.

According to an exemplary embodiment of the present specification, R10 and R11 is a halogen group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.

According to an exemplary embodiment of the present specification, R10 and R11 is a halogen group, an alkyl group having 1 to 6 carbon atoms, or an aryl group having 6 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, Z1 and Z2 are the same as or different from each other and are each a halogen group.

According to an exemplary embodiment of the present specification, Z1 and Z2 are the same as or different from each other and are each a fluorine group.

According to an exemplary embodiment of the present specification, one or more of R6 to R9 is an aryl group unsubstituted or substituted with alkyl having 4 or more carbon atoms.

According to an exemplary embodiment of the present specification, when X1 and X2 are C, Y1 and Y2 are NH, R6 to R9 is an aryl group unsubstituted or substituted with alkyl having 4 or more carbon atoms.

According to an exemplary embodiment of the present specification, Chemical Formula 1 is represented by the following structural formula.

According to an exemplary embodiment of the present specification, the compound of Chemical Formula 1 has a maximum emission peak within 460 nm to 550 nm.

According to an exemplary embodiment of the present specification, the compound of Formula 1 has a maximum absorption peak within 450 nm to 540 nm.

According to an exemplary embodiment of the present specification, the resin matrix; And it provides a color conversion film comprising a compound represented by the formula (1) dispersed in the resin matrix.

The content of the compound represented by Chemical Formula 1 in the color conversion film may be in the range of 0.001 to 10% by weight.

The color conversion film may include one type of compound represented by Formula 1, or may include two or more types.

The color conversion film may further include an additional fluorescent material in addition to the compound represented by Chemical Formula 1. When using a light source that emits blue light, the color conversion film preferably includes both a green light emitting phosphor and a red light emitting phosphor. In addition, when using a light source that emits blue light and green light, the color conversion film may include only a red light emitting fluorescent material. However, the present invention is not limited thereto, and in the case of using a light source that emits blue light, when laminating a separate film including a green light emitting fluorescent substance, the color conversion film may include only a red light emitting compound. On the contrary, even when using a light source that emits blue light, when laminating a separate film containing a red light-emitting fluorescent substance, the color conversion film may include only a green light emitting compound.

The color conversion film is a resin matrix; And an additional layer including a compound dispersed in the resin matrix and emitting light having a wavelength different from that of the compound represented by Chemical Formula 1. The compound emitting light of a wavelength different from that of the compound represented by Chemical Formula 1 may also be a compound represented by Chemical Formula 1, or may be another known fluorescent substance.

It is preferable that the material of the said resin matrix is a thermoplastic polymer or a thermosetting polymer. Specifically, the material of the resin matrix is a poly (meth) acrylic, polycarbonate (PC), polystyrene (PS), polyarylene (PAR), polyurethane (TPU) such as polymethyl methacrylate (PMMA) ), Styrene-acrylonitrile (SAN), polyvinylidene fluoride (PVDF), modified polyvinylidene fluoride (modified-PVDF) and the like can be used.

According to one embodiment of the present specification, the color conversion film according to the above-described embodiment further includes light diffusing particles. By dispersing the light-diffusing particles into the color conversion film instead of the light-diffusion film conventionally used to improve the brightness, it is possible to omit the attaching process and to achieve higher brightness as compared to using a separate optical-diffusion film. Can be represented.

As the light diffusing particles, a resin matrix and particles having high refractive index may be used, such as TiO ₂ , silica, borosilicate, alumina, sapphire, air or other gas, air- or gas-filled hollow beads or particles (eg, , Air / gas-filled glass or polymer); Polymer particles including polystyrene, polycarbonate, polymethylmethacrylate, acrylic, methyl methacrylate, styrene, melamine resin, formaldehyde resin, or melamine and formaldehyde resin, or any suitable combination thereof may be used. .

The particle diameter of the light diffusing particles may be in the range of 0.1 micrometers to 5 micrometers, such as in the range of 0.3 micrometers to 1 micrometer. The content of the light diffusing particles may be determined as needed, and may be, for example, in the range of about 1 to 30 parts by weight based on 100 parts by weight of the resin matrix.

The color conversion film according to the above-described embodiment may have a thickness of 2 micrometers to 200 micrometers. In particular, the color conversion film may exhibit high luminance even at a thin thickness of 2 micrometers to 20 micrometers. This is because the content of the fluorescent substance molecules contained in the unit volume is higher than that of the quantum dots.

The color conversion film according to the above-described embodiment may be provided with a substrate on one surface. This substrate can function as a support in the production of the color conversion film. It does not specifically limit as a kind of base material, As long as it is transparent and can function as the said support body, it is not limited to the material and thickness. Here, transparent means that visible light transmittance is 70% or more. For example, a PET film may be used as the substrate.

The above-described color conversion film may be prepared by coating and drying a resin solution in which the compound represented by Chemical Formula 1 is dissolved on a substrate and drying the film, or by extruding the compound represented by Chemical Formula 1 together with the resin to form a film.

Since the compound represented by Formula 1 is dissolved in the resin solution, the compound represented by Formula 1 is uniformly distributed in the solution. This is different from the manufacturing process of the quantum dot film that requires a separate dispersion process.

The resin solution in which the compound represented by Chemical Formula 1 is dissolved is not particularly limited as long as the compound represented by Chemical Formula 1 is dissolved in a solution.

According to an example, the resin solution in which the compound represented by Chemical Formula 1 is dissolved may be prepared by dissolving the compound represented by Chemical Formula 1 in a solvent to prepare a first solution, and then prepare a second solution by dissolving the resin in solvent. It may be prepared by a method of mixing the solution and the second solution. When mixing the first solution and the second solution, it is preferable to mix homogeneously. However, the present invention is not limited thereto, but the method of dissolving the compound represented by the formula (1) and the resin at the same time to dissolve, the method of dissolving the compound represented by the formula (1) in the solvent, followed by the addition of the resin to dissolve, the resin in the solvent and then the formula (1) A method of adding and dissolving a compound represented by the above may be used.

As the resin contained in the solution, the above-mentioned resin matrix material, a monomer curable with this resin matrix resin, or a mixture thereof can be used. For example, the monomer curable with the resin matrix resin includes a (meth) acrylic monomer, which may be formed of a resin matrix material by UV curing. When using such a curable monomer, an initiator necessary for curing may be further added as necessary.

The solvent is not particularly limited and is not particularly limited as long as it can be removed by drying without adversely affecting the coating process. Non-limiting examples of the solvent include toluene, xylene, acetone, chloroform, various alcohol solvents, MEK (methyl ethyl ketone), MIBK (methyl isobutyl ketone), EA (ethyl acetate), butyl acetate, DMF ( Dimethylformamide), DMAc (dimethylacetamide), DMSO (dimethylsulfoxide), NMP (N-methyl-pyrrolidone) and the like can be used, and one or two or more thereof can be used in combination. When using the said 1st solution and a 2nd solution, the solvent contained in each of these solutions may be the same, and may differ. Even when different kinds of solvents are used in the first solution and the second solution, it is preferable that these solvents have compatibility so that they can be mixed with each other.

The process of coating the resin solution in which the compound represented by Formula 1 is dissolved on a substrate may use a roll-to-roll process. For example, after the substrate is unrolled from the roll on which the substrate is wound, a surface of the substrate may be coated with a resin solution in which the compound represented by Formula 1 is dissolved, dried, and then wound on a roll. When using a roll-to-roll process, it is preferable to determine the viscosity of the said resin solution to the range in which the said process is possible, for example, it can determine within the range of 200-2,000 cps.

As the coating method, various known methods may be used. For example, a die coater may be used, and various bar coating methods such as a comma coater and a reverse comma coater may be used.

After the coating, a drying process is performed. The drying process can be carried out under the conditions necessary to remove the solvent. For example, in the direction in which the substrate proceeds during the coating process, the solvent is dried under conditions such that the solvent is sufficiently blown in an oven located adjacent to the coater, and a color conversion method including a fluorescent material including a compound represented by Chemical Formula 1 having a desired thickness and concentration on the substrate. A film can be obtained.

When the monomer curable with the resin matrix resin is used as the resin contained in the solution, curing such as UV curing may be performed before or simultaneously with the drying.

When extruding the compound represented by Chemical Formula 1 together with the resin to form a film, extrusion methods known in the art may be used. For example, the compound represented by Chemical Formula 1 may be polycarbonate-based (PC) or poly (meth). A color conversion film can be manufactured by extruding together resins, such as an acryl-type and a styrene- acrylonitrile-type (SAN).

According to an exemplary embodiment of the present specification, the color conversion film may be provided with a protective film or a barrier film on at least one surface. As the protective film and the barrier film, those known in the art may be used.

According to an exemplary embodiment of the present specification, a backlight unit including the color conversion film described above is provided. The backlight unit may have a backlight unit configuration known in the art except for including the color conversion film. 1 illustrates a schematic diagram of a backlight unit structure according to an example. The backlight unit according to FIG. 1 includes a side chain type light source 101, a reflector 102 surrounding the light source, a light guide plate 103 that emits light directly from the light source, or guides light reflected from the reflector, and is provided on one surface of the light guide plate. And a color conversion film 105 provided on a surface opposite to a surface of the light guide plate that faces the reflective layer. In FIG. 1, the gray area is the light dispersion pattern 106 of the light guide plate. The light introduced into the light guide plate has non-uniform light distribution due to the repetition of optical processes such as reflection, total reflection, refraction, and transmission. A two-dimensional light dispersion pattern may be used to guide the light to uniform brightness. However, the scope of the present invention is not limited by FIG. 1, and the light source may be a direct chain type as well as a side chain type, and a reflecting plate or a reflective layer may be omitted or replaced with another configuration as necessary, and may be additionally added as necessary. Film, for example, a light diffusing film, a light collecting film, a brightness enhancing film and the like may be further provided.

According to an exemplary embodiment of the present specification, a display device including the backlight unit is provided. The display device including the backlight unit is not particularly limited and may be included in a TV, a computer monitor, a notebook computer, a mobile phone, and the like.

Comparative Example [1]

Compound [1]

Difluoro {2- [1- (3,5-dimethyl-2H-pyrrole-2-yridine-N) ethyl] -3,5-dimethyl-1H-pyrrolato-N} boron (CAS No : 121207-31-6) was used to prepare a film.

Film production method of compound [1]

Using [Compound 1], it was used for producing a green light emitting color conversion film. Specifically, 0.2 wt% of [Compound 1], which is a green luminescent material, is added to 100 wt% of the SAN polymer, and 3 wt% of diffuser particles are added to the PET film using a solution of 30% solids in a normal butyl acetate solvent. The coating proceeds to produce a green light-emitting color conversion film. With the green conversion film prepared, a backlight unit of 160 mm × 90 mm was manufactured using a blue LED light source. Optical properties were confirmed in the manufactured backlight unit, and the manufactured backlight unit was continuously driven in a chamber at a 60 degree temperature to evaluate light resistance of the green light emitting film.

Example [1]

Compound [2]

Method for Preparation of Compound [2]

3.2 g of ethyl 2,4-dimethylpyrrole-3-carboxylate was dissolved in dichloromethane and then 1 ml of benzaldehyde was added. After stirring for 15 minutes, 1 to 2 drops of trifluoroacetic acid were added thereto, followed by stirring at room temperature for 12 hours. After stirring, 2.18 g of 2,3-dichloro-5,6-dicyano-p-benzoquinone was added, followed by further stirring for 15 minutes. 6.57 ml of triethylamine was added to the stirred mixture, and then 7.7 ml of boron trifluoride-ethyl ether complex was slowly added and stirred for an additional 5 hours. After the stirring was completed, the reaction was terminated with water, extracted with dichloromethane, and the extracted material was concentrated to obtain I-0 by column chromatography.

1 H NMR (500 MHz, CDCl 3) ppm 7.55 (m, 3H), 7.29 (m, 2H), 4.29 (q, 4H), 2.84 (s, 6H), 1.66 (s, 6H), 1.33 (t, 6H) mass : 468.3105

0.3 g of prepared I-0 was dissolved in methanol, and 0.15 g of potassium hydroxide was added thereto, followed by stirring at 60 ° C. for 12 hours. After stirring, the mixture was washed with water and extracted with dichloromethane. The extracted solution was concentrated, dissolved in dimethylformamide solvent, and about 1 ml of TEA was added. After adding 0.6 ml of benzylamine, the mixture was stirred at room temperature for 5 hours. After stirring, the mixture was washed with water and extracted with dichloromethane. The extracted solution was concentrated and compound [2] was prepared by column chromatography.

1 H NMR (500 MHz, CDCl 3) ppm 7.53 (m, 9H), 7.37-7.24 (m, 6H), 5.82 (br, 2H), 4.58 (s, 2H), 2.85 (s, 6H), 1.66 (s, 6H mass: 590.48

Film Production Method Using [Compound 2]

It was used to prepare a green light emitting color conversion film using [Compound 2]. Specifically, 0.2 wt% of [Compound 2], which is a green luminescent material, is added to 100 wt% of the SAN polymer, and 3 wt% of diffuser particles are added to the PET film using a 30% solids solution in a normal butyl acetate solvent. The coating proceeds to produce a green light-emitting color conversion film. With the green conversion film prepared, a backlight unit of 160 mm × 90 mm was manufactured using a blue LED light source. Optical properties were confirmed in the manufactured backlight unit, and the manufactured backlight unit was continuously driven in a chamber at 60 ° C. to evaluate the light resistance of the green light emitting film.

Example [2]

Compound [3]

Method for Preparation of Compound [3]

0.3 g of I-0 prepared in Example 1 was dissolved in methanol, and 0.15 g of potassium hydroxide was added thereto, followed by stirring at 60 ° C. for 12 hours. After stirring, the mixture was washed with water and extracted with dichloromethane. The extracted solution was concentrated, dissolved in dimethylformamide solvent, and about 1 ml of triethylamine was added. After adding 1 ml of ethyl amine, the mixture was stirred at room temperature for 5 hours. After stirring, the mixture was washed with water and extracted with dichloromethane. The extracted solution was concentrated and compound [3] was prepared by column chromatography.

1 H NMR (500 MHz, CDCl 3) ppm 7.53 (m, 3H), 7.37-7.24 (m, 2H), 5.82 (br, 2H), 4.58 (s, 4H), 2.85 (s, 6H), 1.66 (s, 6H ), 1.45 (m, 6H) mass: 590.48

Film production method using [Compound 3]

It was used to prepare a green light emitting color conversion film using [Compound 3]. Specifically, 0.2 wt% of [Compound 3], which is a green light emitting material, is added to 100 wt% of the SAN polymer, and 3 wt% of diffuser particles are added to the PET film using a 30% solids solution in a normal butyl acetate solvent. The coating proceeds to produce a green light-emitting color conversion film. With the green conversion film prepared, a backlight unit of 160 mm × 90 mm was manufactured using a blue LED light source. Optical properties were confirmed in the manufactured backlight unit, and the manufactured backlight unit was continuously driven in a chamber at 60 ° C. to evaluate the light resistance of the green light emitting film.

Example [3]

Compound [4]

Method for Preparation of Compound [4]

[Compound 1] After dissolving 0.5g in acetonitrile solvent 3ml of chlorosulphonic acid was added and stirred. After stirring for 5 hours at room temperature, the reaction was terminated with water and extracted with dichloromethane. After extraction, the resultant was concentrated and dissolved in acetonitrile again. 0.4 ml of triethylamine was added thereto, followed by stirring for 15 minutes. After stirring, 0.3 ml of an aqueous 70% ethylamine solution was added, followed by further stirring for 4 hours. After stirring, the mixture was diluted with water, extracted with dichloromethane, and concentrated. The concentrated solution was separated using column chromatography to prepare [Compound 6].

1 H NMR (500 MHz, CDCl 3) ppm 6.34 (br s, 2H), 2.82 (6H), 2.75 (6H), 2.72 (3H), 2.62 (4H), 2.51 (6H) mass: 476.36

Film production method using [Compound 4]

Using [Compound 4] was used in the production of green light emitting color conversion film. Specifically, 0.2 wt% of [Compound 4], which is a green light emitting material, is added to 100 wt% of the SAN polymer, and 3 wt% of diffuser particles are added to the PET film by using a solution of 30% solids in a normal butyl acetate solvent. The coating proceeds to produce a green light-emitting color conversion film. With the green conversion film prepared, a backlight unit of 160 mm × 90 mm was manufactured using a blue LED light source. Optical properties were confirmed in the manufactured backlight unit, and the manufactured backlight unit was continuously driven in a chamber at 60 ° C. to evaluate the light resistance of the green light emitting film.

Example [4]

Compound [5]

Method for Preparation of Compound [5]

4.5 g of 2,4-dimethylpyrrole was dissolved in dichloromethane, and 2.5 g of benzaldehyde was added thereto, followed by stirring for 15 minutes. After stirring, 1-2 drops of trifluoroacetic acid were added thereto, followed by stirring at room temperature for 12 hours. Thereafter, 5.45 g of 2,3-dichloro-5,6-dicyano-p-benzoquinone was added, followed by further stirring for 15 minutes. 16.42 ml of triethylamine was added to the stirred mixture, after which 19.2 ml of boron trifluoride-ethylether complex was slowly added and stirred for an additional 5 hours. After stirring was complete, the reaction was terminated with water, extracted with dichloromethane, and the extracted material was concentrated to prepare a substance I-1 by column chromatography.

1 H NMR (500 MHz, CDCl 3) ppm 7.47 (m, 3H), 7.27 (m, 2H), 5.98 (s, 2H), 2.55 (s, 6H), 1.37 (s, 6H) mass: 324.18

0.5 g of the prepared I-1 material was dissolved in acetonitrile solvent, and 3 ml of chlorosulphonic acid was added thereto, followed by stirring. After stirring for 5 hours at room temperature, the reaction was terminated with water and extracted with dichloromethane. Extracted and concentrated. The concentrated solution was separated by column chromatography to prepare [Compound 5].

1 H NMR (500 MHz, CDCl 3) ppm 7.66 (m, 3H), 7.31 (m, 2H), 2.95 (s, 6H), 1.98 (s, 6H) mass: 521.1807

Film Production Method Using [Compound 5]

It was used to prepare a green light emitting color conversion film using [Compound 5]. Specifically, 0.2 wt% of [Compound 5], which is a green light emitting material, is added to 100 wt% of the SAN polymer, and 3 wt% of diffuser particles are added to the PET film using a solution of 30% solids in a normal butyl acetate solvent. The coating proceeds to produce a green light emitting color conversion film. With the green conversion film prepared, a backlight unit of 160 mm × 90 mm was manufactured using a blue LED light source. Optical properties were confirmed in the manufactured backlight unit, and the manufactured backlight unit was continuously driven in a chamber at 60 ° C. to evaluate the light resistance of the green light emitting film.

Example [5]

Compound [6]

Method for preparing compound [6]

[Compound 5] After dissolving 0.5 g in acetonitrile solvent, 0.4 ml of triethylamine was added and stirred for 15 minutes. After stirring, 0.25 ml of an aqueous 70% ethylamine solution was added, followed by further stirring for 4 hours. After stirring, the mixture was diluted with water, extracted with dichloromethane, and concentrated. The concentrated solution was separated using column chromatography to prepare [Compound 6].

1 H NMR (500 MHz, CDCl 3) ppm 7.66 (m, 3H), 7.31 (m, 2H), 3.01 (m, 4H) 2.86 (s, 6H), 1.66 (s, 6H), 1.15 (s, 6H) mass: 538.4404

Film Production Method Using [Compound 6]

It was used to prepare a green light emitting color conversion film using [Compound 6]. Specifically, 0.2 wt% of [Compound 6], which is a green light emitting material, is added to 100 wt% of the SAN polymer, and 3 wt% of diffuser particles are added to the PET film using a 30% solids solution in a normal butyl acetate solvent. The coating proceeds to produce a green light emitting color conversion film. With the green conversion film prepared, a backlight unit of 160 mm × 90 mm was manufactured using a blue LED light source. Optical properties were confirmed in the manufactured backlight unit, and the manufactured backlight unit was continuously driven in a chamber at 60 ° C. to evaluate the light resistance of the green light emitting film.

The optical properties of the films prepared from Comparative Example 1 and Examples 1 to 5 are compared and shown in Table 1 and FIG. 2.

Comparative Example 1 Example 1 Example 2 Example 3 Example 4 Example 5 Max intensity Blue 0.1982 0.3115 0.294 0.1125 0.1847 0.3726 Green 0.1604 0.1355 0.1513 0.1263 0.069 0.1194 Max wavelength Blue 449 450 450 450 449 450 Green 536 533 534 539 542 527 FWHM Blue Width (nm) 18 19 19 20 18 18 Green Width (nm) 44 40 39 46 55 37

The light resistance results of the films prepared from Comparative Example 1 and Examples 1 to 5 are shown in Table 2 below.

Evaluation time % Green Intensity Comparative Example 1 Example 1 Example 2 Example 3 Example 4 Example 5 24hr 70% 86% 96% 75% 76% 99% 100hr 51% 71% 88% 72% 71% 95% 250hr 38% 53% 78% 50% 53% 87% 500hr 21% 43% 63% 39% 43% 81% 750 hr 15% 29% 60% 33% 29% 76% 1000hr 7% 57% 57% 29% 20% 67%

101: side chain light source
102: reflector
103: light guide plate
104: reflective layer
105: color conversion film
106: light dispersion pattern

Claims (13)

A compound represented by any one of the following Formulas 2 to 4:
[Formula 2]

[Formula 3]

[Formula 4]

In Chemical Formulas 2 to 4,
L1 and L2 are the same as or different from each other, and each independently an alkylene group or a direct bond,
R1 to R9 are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted alkyl group,
R10 and R11 are the same as or different from each other, and each independently halogen; Substituted or unsubstituted C2 or more alkyl group; Or a substituted or unsubstituted aryl group, n and m are each 1 or 2,
Z1 and Z2 are the same as or different from each other, and each independently halogen; Nitrile group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Or a substituted or unsubstituted aryl group, or Z1 and Z2 combine with each other to form a substituted or unsubstituted ring. delete The compound of claim 1, wherein R 6 to R 9 are alkyl groups having 1 to 6 carbon atoms. The compound of claim 1, wherein at least one of R 6 to R 9 is an aryl group unsubstituted or substituted with alkyl having 4 or more carbon atoms. The compound according to claim 1, wherein in Formula 2, R6 to R9 is an aryl group unsubstituted or substituted with alkyl having 4 or more carbon atoms. The compound of claim 1, wherein L 1 and L 2 are a direct bond or an alkylene group having 1 to 6 carbon atoms. delete The compound according to claim 1, wherein the compound is represented by the following structural formula:

The compound of claim 1, wherein the maximum emission peak is within 460 nm to 550 nm. The compound of claim 1, wherein the maximum absorption peak is present within 450 nm to 540 nm. Resin matrix; And a compound according to any one of claims 1, 3 to 6 and 8 to 10 dispersed in the resin matrix. A backlight unit comprising the color conversion film according to claim 11. Display device comprising a backlight unit according to claim 12.

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