KR102128151B1 - Compound containing nitrogen and color conversion film comprising the same - Google Patents

Abstract

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

Description

Nitrogen-containing cyclic compound and color conversion film comprising the 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 comprising the same, a backlight unit and a display device.

Conventional light-emitting diodes (LEDs) are obtained by mixing a green phosphor and a red phosphor with a blue light-emitting diode or by mixing a yellow phosphor and a blue-green phosphor with a UV light-emitting light-emitting diode. However, such a method is difficult to control the color, and accordingly color rendering is not good. Therefore, the color reproduction rate is poor.

In order to overcome the fall in color reproduction rate and reduce production cost, a method of implementing green and red as a method of forming a quantum dot and bonding it to a blue LED has been recently attempted. However, cadmium-based quantum dots have safety problems, and other quantum dots have significantly lower efficiency than cadmium-based. In addition, quantum dots have a disadvantage in that their stability to oxygen and water is poor and their performance is remarkably reduced when aggregated. In addition, the production cost is high because it is difficult to keep the size constant during the production of quantum dots.

Korean Patent Publication No. 2000-0011622

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

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

[Formula 1]

X1 and X2 are each independently a halogen group; Cyano group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted ester group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted aryl group; And a substituted or unsubstituted heterocyclic group.

X3 and X4 are each independently selected from the group consisting of O, S and Se,

R1 and R7 are each independently a substituted or unsubstituted aryl group; And a substituted or unsubstituted heterocyclic group.

R2 and R6 are each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted ester group; A substituted or unsubstituted aryl group; And it is any one selected from the group consisting of a heterocyclic group,

R3 and R5 are each independently a substituted or unsubstituted cycloalkyl group,

R4 is a substituted or unsubstituted aryl group; And a substituted or unsubstituted heterocyclic group.

According to another exemplary embodiment of the present specification, a 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 the exemplary embodiment of the present specification is a material having high fluorescence efficiency and excellent light resistance. Therefore, the color conversion film excellent in luminance and color reproducibility and excellent light resistance can be provided by using the compound described herein as a fluorescent material of the color conversion film.

1 is a schematic diagram of applying a color conversion film according to an exemplary embodiment of the present disclosure to a backlight.

Hereinafter, the present specification will be described in more detail.

According to the exemplary embodiment of the present specification, the compound represented by Chemical Formula 1 is provided.

In the present specification, when a part “includes” a certain component, it means that the component may further include other components, not to exclude other components, unless otherwise stated.

In this specification, when a member is said to be "on" another member, this includes not only the case where one member is in contact with the other member but also another member between the two members.

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

The term "substitution" means that the hydrogen atom bonded to the 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 the substituent can be substituted, and when two or more are substituted , 2 or more substituents may be the same or different from each other.

The term "substituted or unsubstituted" as used herein refers to deuterium; Halogen group; Nitrile group; Nitro group; Imide group; Amide group; Carbonyl group; Carboxy group (-COOH); Ether group; Ester groups; Hydroxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthioxy group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkyl sulfoxy group; A substituted or unsubstituted aryl sulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; And a substituted or unsubstituted heterocyclic group, substituted with 1 or 2 or more substituents selected from the group consisting of substituted or unsubstituted substituents, or having no substituents. For example, "a substituent having two or more substituents" 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 connected.

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

Means a site that is attached to another substituent or linkage.

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

In this specification, the number of carbon atoms of the imide group is not particularly limited, but is preferably 1 to 30 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

In the present specification, the nitrogen of the amide group may be substituted with hydrogen, a straight chain, 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.

In this specification, the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 30 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

In the present specification, the ether group is a straight chain, branched or cyclic alkyl group having 1 to 25 carbon atoms in the ether; Or it may be substituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

In the present specification, the ester group is a straight-chain, branched or cyclic alkyl group having 1 to 25 carbon atoms in the ester group; Or it may be substituted with 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 straight chain or branched chain, and carbon number is not particularly limited, but is preferably 1 to 30. Specific examples are 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 has 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. It is not.

In the present specification, the alkoxy group may be a straight chain, branched chain or cyclic chain. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 30 carbon atoms. 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, etc. It may be, but is not limited thereto.

In the present specification, the amine group is -NH ₂ ; Alkylamine groups; N-aryl alkylamine group; Arylamine group; N-aryl heteroarylamine group; It may be selected from the group consisting of N-alkylheteroarylamine groups and heteroarylamine groups, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group are methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, 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 alkenyl group may be straight chain or branched chain, and 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, steelbenyl group, styrenyl group, and the like, but are not limited thereto.

In the present specification, the alkynyl group refers to a straight-chain carbon bond having a triple bond, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30. Specific examples include 1-propene, 2-butyne, ethynylbenzene, 1-propynylbenzene, 1-ethynyl-4-nitrobenzene, 1-nitro-4-(1-propyn-1-yl)benzene, etc. There is, but is not limited to this.

In the present specification, the silyl group is specifically trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, etc. However, it 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 or different, 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; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And it may be selected from the group consisting of substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

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

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

When the aryl group is a monocyclic aryl group, the number of carbon atoms 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, or a terphenyl group, but is not limited thereto.

When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. It is preferable that it has 10 to 30 carbon atoms. Specifically, the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, triphenyl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group, 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

It can be back. However, it is not limited thereto.

In the present specification, an aryl group in an aryloxy group, an arylthioxy group, an aryl sulfoxy group, an N-aryl alkylamine group, an N-aryl heteroarylamine group, and an arylphosphine group is the same as the above-described examples of the aryl group. Specifically, aryloxy groups include phenoxy group, p-toryloxy 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, and arylthioxy groups are phenylthioxy groups, 2- Methylphenyl thioxy group, 4-tert-butylphenyl thioxy group, and the like, but aryl sulfoxy group includes benzene sulfoxy group, p-toluene sulfoxy group, but is not limited thereto.

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 or a polycyclic aryl group. The arylamine group containing two or more aryl groups may include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group simultaneously. For example, the aryl group in the arylamine group can be selected from the examples of the aryl group described above.

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

According to an exemplary embodiment of the present specification, X1 and X2 are each independently a halogen group; Cyano group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted ester group; And it is any one selected from the group consisting of a substituted or unsubstituted alkynyl group.

According to an exemplary embodiment of the present specification, X1 and X2 are each independently a fluorine group; Cyano group; A substituted or unsubstituted ester group; Or a substituted or unsubstituted alkynyl group.

According to an exemplary embodiment of the present specification, the compound of Formula 1 is selected from the following structural formula.

According to an exemplary embodiment of the present specification, the formula 1 is represented by a combination of any one of the following Table 1, Table 2, and Table 3-1 to Table 3-7. For example, the following compound is represented as Compound A-1-200.

[Table 1]

[Table 2]

[Table 3-1]

[Table 3-2]

[Table 3-3]

[Table 3-4]

[Table 3-5]

[Table 3-6]

[Table 3-7]

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 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 the 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, it is preferable that the color conversion film includes both a green light emitting fluorescent material and a red light emitting fluorescent material. In addition, when using light sources that emit blue light and green light, the color conversion film may include only red light-emitting fluorescent materials. However, the present invention is not limited thereto, and even when a light source that emits blue light is used, when a separate film containing a green light-emitting fluorescent substance is laminated, the color conversion film may include only a red light-emitting compound. Conversely, even when a light source that emits blue light is used, when a separate film containing a red light-emitting fluorescent substance is laminated, the color conversion film may include only a green light-emitting compound.

The color conversion film is a resin matrix; And an additional layer comprising 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 which emits light of a different wavelength from the compound represented by Chemical Formula 1 may also be a compound represented by Chemical Formula 1 or other known fluorescent material.

It is preferable that the material of the resin matrix is a thermoplastic polymer or a thermosetting polymer. Specifically, the material of the resin matrix is poly(meth)acrylic, polycarbonate-based (PC), polystyrene-based (PS), polyarylene-based (PAR), polyurethane-based (TPU) such as polymethyl methacrylate (PMMA). ), styrene-acrylonitrile system (SAN), polyvinylidene fluoride system (PVDF), modified polyvinylidene fluoride system (modified-PVDF), etc. may 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 inside the color conversion film instead of the conventional light-diffusion film to improve the brightness, as well as omitting the attachment process compared to using a separate optical acid film, higher luminance Can be represented.

As the light-diffusing particles, a resin matrix and particles having a high refractive index may be used, such as TiO ₂ , silica, borosilicate, alumina, sapphire, air or other gases, 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 can be used. .

The particle size of the light-diffusing particles may be in the range of 0.1 micrometer to 5 micrometer, for example, in the range of 0.3 micrometer to 1 micrometer. The content of the light-diffusing particles may be determined as necessary, for example, may be 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 exemplary embodiment may have a thickness of 2 micrometers to 200 micrometers. In particular, the color conversion film may exhibit high luminance even in a thickness of 2 to 20 micrometers. This is because the content of the fluorescent substance molecule contained on the unit volume is higher than that of the quantum dots.

The color conversion film according to the above-described exemplary 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. The type of the substrate is not particularly limited, and is not limited to the material or thickness as long as it is transparent and can function as the support. Here, transparent means that the 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 a resin solution in which the compound represented by the formula (1) is dissolved on a substrate and drying, or extruding the compound represented by the formula (1) together with the resin to form a film.

Since the compound represented by Chemical Formula 1 is dissolved in the resin solution, the compound represented by Chemical Formula 1 is homogeneously 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 the formula (1) is dissolved is not particularly limited as long as the compound represented by the formula (1) in the solution is dissolved in the resin.

According to an example, the resin solution in which the compound represented by Formula 1 is dissolved is prepared by dissolving the compound represented by Formula 1 in a solvent to prepare a first solution, and dissolving the resin in a solvent to prepare a second solution, and the first It can 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, and a method of simultaneously dissolving a compound represented by Formula 1 and a resin in a solvent, and a method of dissolving a compound represented by Formula 1 in a solvent and then adding a resin to dissolve it, and then dissolving the resin in a solvent and then formula 1 A method of dissolving by adding a compound represented by may be used.

As the resin contained in the solution, the aforementioned resin matrix material, a monomer curable with the resin matrix resin, or a mixture thereof may be used. For example, a monomer that can be cured with the resin matrix resin is a (meth)acrylic monomer, which can 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 later without adversely affecting the coating process. Non-limiting examples of the solvent include toluene, xylene, acetone, chloroform, various alcohol-based solvents, MEK (methyl ethyl ketone), MIBK (methyl isobutyl ketone), EA (ethyl acetate), butyl acetate, DMF ( Dimethyl formamide), DMAc (dimethylacetamide), DMSO (dimethyl sulfoxide), NMP (N-methyl-pyrrolidone), and the like may be used, and one or two or more of them may be used in combination. When using the first solution and the second solution, the solvent contained in each of these solutions may be the same or different. Even when different types of solvents are used for 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 Chemical Formula 1 is dissolved on a substrate may use a roll-to-roll process. For example, after unwinding the substrate from the roll on which the substrate is wound, a resin solution in which the compound represented by Chemical Formula 1 is dissolved is coated on one surface of the substrate, and after drying, it can be performed in a process of winding it back onto the roll. When using a roll-to-roll process, it is preferable to determine the viscosity of the resin solution in a range in which the process is possible, for example, it may be determined within a range of 200 to 2,000 cps.

Various known methods may be used as the coating method, 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 performed under conditions necessary to remove the solvent. For example, a color conversion including a fluorescent substance including a compound represented by Chemical Formula 1 of a desired thickness and concentration on a substrate by drying under a condition in which the solvent is sufficiently blown in an oven located adjacent to the coater in a direction in which the substrate proceeds during the coating process. You can get a film.

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

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

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, to provide a backlight unit including the above-described color conversion film. The backlight unit may have a backlight unit configuration known in the art, except that the color conversion film is included. 1 is a schematic diagram of a backlight unit structure according to an example. The backlight unit according to FIG. 1 is provided on one side of the light guide plate 101, a reflecting plate 102 surrounding the light source, a light guide plate 103 that directly emits light from the light source, or induces light reflected from the reflecting plate. It includes a reflective layer 104, and a color conversion film 105 provided on the opposite surface of the surface opposite to the reflective layer of the light guide plate. In FIG. 1, the gray portion is the light dispersion pattern 106 of the light guide plate. Light introduced into the light guide plate has a non-uniform light distribution through repetition of optical processes such as reflection, total reflection, refraction, and transmission, and a two-dimensional light dispersion pattern may be used to induce uniform brightness. However, the scope of the present invention is not limited by FIG. 1, and a light source may be used as well as a side chain type and a direct type may be used, and the reflector or the reflective layer may be omitted or replaced with other configurations as necessary, and added as necessary. A film of, for example, a light diffusion film, a light collecting film, a brightness enhancing film, and the like may be further provided.

According to one 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 laptop, and a mobile phone.

Hereinafter, the present specification will be described in detail by way of examples. The following examples are intended to illustrate the present specification, and the scope of the present specification includes the ranges and substitutions and modifications described in the following claims, and is not limited to the scope of the examples.

Compound C-26- 497 of synthesis

497a synthesis

After dissolving 10 g of dibenzofuran-2-aldehyde and 3 equivalents of pyrrole in dichloromethane, add 0.1 equivalent of trifluoroacetic acid and stir. After confirming the progress of the reaction by TLC and lowering to 0°C, 1.1 equivalent of DDQ was slowly added. After stirring for about an hour, the temperature was lowered to 0°C again, and 6 equivalents of triethylamine and 9 equivalents of trifluoroboron ethyl islate were added dropwise. After the reaction was completed, DDQ was removed using a sodium hydroxide solution and extracted with chloroform. The extracted organic layer removes water using magnesium sulfate and distills under reduced pressure to remove the solvent. Recrystallization using methanol gave 7.6 g (42%) of 497a material.

497b of synthesis

7.6 g of 497a was dissolved in dichloromethane, and then lowered to 0°C, 3 equivalents of bromine was slowly added dropwise. After confirming that the reaction panel is in progress, add water to terminate the reaction. After extraction using chloroform, the organic layer dried using magnesium sulfate is distilled under reduced pressure to remove the solvent. Column chromatography was used to obtain 5.6 g (52%) of 497b material.

497d synthesis

5.6 g of 497b was dissolved in an acetonitrile solvent, and 2.2 equivalents of 497c and 3 equivalents of potassium carbonate were added. After stirring for about an hour and confirming that the reaction is complete, extraction is performed with water and chloroform. The organic layer is dried using magnesium sulfate, and the obtained organic layer is distilled under reduced pressure and concentrated. Recrystallization with a methanol solvent gave 6.8 g (72%) of a 497 d material.

497e synthesis

6.8 g of 497 d was dissolved in a DMF solvent, 2.5 equivalents of cyclopropyl trifluoroborate potassium salt and 5 equivalents of manganese acetate dihydrate were added and stirred with heating. After about 3 hours, confirm the reaction and, when finished, cool to room temperature and add water. The mixed solution is filtered using Celite, and Celite is again dissolved in chloroform to dissolve the solid. The water is removed using magnesium sulfate and the solid is removed again by filtration. The solvent is removed through distillation under reduced pressure and the crystal is collected using methanol. 4.5g (61%) of 497e material could be obtained.

C-26- 497 of synthesis

After dissolving 497e 4.5g in dichloromethane, add 5 equivalents of chlorotrimethylsilane. After stirring for about an hour at room temperature, add 7 equivalents of trifluoroacetic acid and stir for heating. After the reaction is completed, the mixture is extracted with chloroform and water, and the organic layer is dried using magnesium sulfate. After removing the solvent through distillation under reduced pressure, a metalol is used to obtain a solid. 3.5 g (66%) of C-26-497 material could be obtained.

Compound I-17- 131 of synthesis

Of 131a synthesis

The procedure was the same as the synthesis of 497a except that 4-cyanobenzaldehyde (10 g) was used instead of dibenzofuran-2-aldehyde. 9.8 g (44%) of 131a material could be obtained.

Of 131b synthesis

The procedure was the same as the synthesis of 497b, except that 9.8a of 131a was used instead of 497a. 8.5g (57%) of 131b material could be obtained.

131c synthesis

The procedure was the same as the synthesis of 497d, except that 8.5g of 131b was used instead of 497b. 8.1 g (73%) of 131c material could be obtained.

131d synthesis

The procedure was the same as the synthesis of 497e, except that 8.1g of 131c was used instead of 497d. 4.8 g (49%) of 131d material could be obtained.

I-17- 131 of synthesis

The anhydrous THF solvent in which 2.2 equivalents of 4-nitrobenzeneethynyl was dissolved was lowered to -78°C, and 2.3 equivalents of n-butyllithium was slowly added dropwise. After stirring for about an hour, 4.8 g of 131d is added and stirred while slowly raising to room temperature. After the reaction was completed, extraction was performed using an aqueous sodium bicarbonate solution and chloroform. The extracted organic layer is dried using magnesium sulfate and concentrated by distillation under reduced pressure. The solid was filtered using methanol to obtain 2.7 g (43%) of I-17-131 material.

Compound J-30- 3 of synthesis

3a of synthesis

The procedure was the same as the synthesis of 497a, except that 10 g of dibenzothiophene-2-aldehyde was used instead of dibenzofuran-2-aldehyde. 6.8 g (39%) of 3a material could be obtained.

3b of synthesis

The procedure was the same as the synthesis of 497b, except that 6.8 g of 3a was used instead of 497a. 5.6 g (58%) of material 3b could be obtained.

3c of synthesis

The procedure was the same as the synthesis of 497d except that 3b instead of 497b and trifluorobenzene selenol were used instead of 497c. 4.7 g (55%) of material 3c could be obtained.

3d of synthesis

The procedure was the same as in the synthesis of 497e except that 3c instead of 497d and cyclopentyltrifluoroboron potassium salt were used instead of cyclopropyltrifluoroboron potassium salt. 2.7g (51%) of the material 3d was obtained,

J-30- 3 of synthesis

2.7 g of 3d was dissolved in a dichloromethane solvent, 5 equivalents of AlCl ₃ were added and stirred. Heptafluorobutanol was added, stirred with heating, and when the reaction was completed, extraction was performed with water and chloroform. The organic layer is filtered using celite to remove the remaining aluminum, and magnesium sulfate is used to remove moisture. After removing the solvent by distillation under reduced pressure, 2.0 g (56%) of J-30-3 was obtained by filtering the solid using a metalol.

Compound K-2- 1 of synthesis

1a of synthesis

The procedure was the same as the synthesis of 497a, except that 10 g of benzaldehyde was used instead of dibenzofuran-2-aldehyde. 11.3 g (45%) of material 1a was obtained.

1b of synthesis

The procedure was the same as the synthesis of 497b, except that 1a was used instead of 497a. 9.7 g (56%) of material 1b could be obtained.

1c of synthesis

The procedure was the same as the synthesis of 497d except that 1b instead of 497b and benzenecyol were used instead of 497c. 8.1 g (74%) of material 1c could be obtained.

K-2- 1 of synthesis

The procedure was the same as the synthesis of 497e, except that 1c was used instead of 497d and cyclohexyltrifluoroboron potassium salt was used instead of cyclopropyltrifluoroboron potassium salt. 6.3 g (59%) of the substance K-2-1 was obtained.

Compound K-7- 334 of synthesis

334a synthesis

The procedure was the same as the synthesis of 497a except that 10 g of 3-fluorobenzaldehyde was used instead of dibenzofuran-2-aldehyde. 9.4 g (41%) of material 334a was obtained.

Of 334b synthesis

The procedure was the same as the synthesis of 497b, except that 334a was used instead of 497a. 9.0 g (62%) of material 334b could be obtained.

334c synthesis

The procedure was the same as the synthesis of 497d except that 334b instead of 497b and 2,6-diisopropylphenol was used instead of 497c. 10.4 g (81%) of material 334c was obtained.

334d of synthesis

The procedure was the same as the synthesis of 497e, except that 334c was used instead of 497d and cyclohexyltrifluoroboron potassium salt was used instead of cyclopropyltrifluoroboron potassium salt. 7.5 g (60%) of material 334d could be obtained.

K-7- 334 of synthesis

7.5 g of 334d was dissolved in dichloromethane and then lowered to 0°C. After adding 2.2 equivalents of chlorosulfonyl isocyanate dropwise, the mixture is raised to room temperature. TLC is confirmed by removing the reaction solution and mixing it with a dimethylformamide solvent. When the reaction is over, add about 1 g of dimethylformamide and stir sufficiently. The organic layer is extracted using chloroform and water, and dried using magnesium sulfate. The solvent was removed by distillation under reduced pressure, and then recrystallized using methanol. 6.1 g (77%) of material K-7-334 could be obtained.

Compound L-13- 330 of synthesis

330a synthesis

The procedure was the same as the synthesis of 497a, except that 10 g of 2-methoxybenzaldehyde was used instead of dibenzofuran-2-aldehyde. 8.7g (40%) of material 330a was obtained.

330b synthesis

The procedure was the same as the synthesis of 497b, except that 330a was used instead of 497a. 7.7 g (58%) of material 330b could be obtained.

330c synthesis

The procedure was the same as the synthesis of 497d, except that 330b instead of 497b and 2,6-diisopropylphenol were used instead of 497c. 9.1 g (83%) of material 330c could be obtained.

330d synthesis

The procedure was the same as the synthesis of 497e, except that 330c was used instead of 497d and cyclohexyltrifluoroboron potassium salt was used instead of cyclopropyltrifluoroboron potassium salt. 6.4 g (57%) of material 330d could be obtained.

330e synthesis

6.4 g of 330e is dissolved in a dimethylformamide solvent and 2.1 equivalents of N-iodosuccinimide is added. The reaction was confirmed by heating and stirring. When the reaction was completed, an aqueous sodium cysulfate solution was added and stirred sufficiently. It is extracted using water and chloroform, and the organic layer is dried using magnesium sulfate. The solvent was removed by distillation under reduced pressure, and then recrystallized using methanol. 6.6 g (79%) of material 330e could be obtained.

L-13- 330 of synthesis

6.6 g of the substance 330e was dissolved in a dichloromethane solvent and then lowered to 0°C. 6 equivalents of trimethylsilyl cyanide and 9 equivalents of trifluoroboronethyl islate are slowly added dropwise. After dropwise addition, raise to room temperature and check the reaction. After the reaction is completed, extraction is performed with water and chloroform, and the organic layer is dried using magnesium sulfate. The solvent was removed by distillation under reduced pressure, and then recrystallized using methanol. 4.4 g (67%) of material L-13-330 could be obtained.

Compound L-36- 5 of synthesis

5a of synthesis

The procedure was the same as the synthesis of 497a, except that 15 g of 9,9-diphenylfluorene-3-carbaldehyde was used instead of dibenzofuran-2-aldehyde. 9.4 g (43%) of material 5a could be obtained.

5b of synthesis

The procedure was the same as the synthesis of 497b, except that 5a was used instead of 497a. 7.7 g (63%) of material 5b could be obtained.

5c of synthesis

The procedure was the same as the synthesis of 497d, except that 4b instead of 497b and 4-cyanobenzene selenol were used instead of 497c. 5.6 g (55%) of material 5c could be obtained.

5d of synthesis

The procedure was the same as the synthesis of 497e except that 5c was used instead of 497d and cyclohexyltrifluoroboron potassium salt was used instead of cyclopropyltrifluoroboron potassium salt. 3.8 g (59%) of material 5d could be obtained.

L-36- 5 of synthesis

The procedure was the same as the synthesis of L-13-330, except that 5d was used instead of 330e. 2.6 g (69%) of material L-36-5 could be obtained.

Compound P-1- 106 of synthesis

106a of synthesis

The procedure was the same as the synthesis of 497d except that 1b 5g instead of 497b and phenol was used instead of 497c. 4.3 g (81%) of material 106a could be obtained.

106b of synthesis

The procedure was the same as the synthesis of 497e, except that 106a was used instead of 497d and cyclohexyltrifluoroboron potassium salt was used instead of cyclopropyltrifluoroboron potassium salt. 3.5 g (60%) of material 106b could be obtained.

P-1- 106 of synthesis

The procedure was the same as the synthesis of K-7-334, except that 1.2 equivalents of 106b, chlorosulfonyl isocyanate, was used instead of 334d. 2.9 g (81%) of material P-1-106 could be obtained.

Compound P-4- 559 of synthesis

559a synthesis

The procedure was the same as the synthesis of 497a, except that 10 g of mesitylbenzaldehyde was used instead of dibenzofuran-2-aldehyde. 7.9 g (38%) of material 559a could be obtained.

559b synthesis

The procedure was the same as the synthesis of 497b, except that 559a was used instead of 497a. 7.3 g (62%) of material 559b could be obtained.

559d synthesis

The procedure was the same as the synthesis of 497d, except that 559b instead of 497b and 559c instead of 497c were used. 10.3 g (83%) of material 559d could be obtained.

559e synthesis

The procedure was the same as the synthesis of 497e except that 559d was used instead of 497d and methylcyclohexyltrifluoroboron potassium salt was used instead of cyclopropyltrifluoroboron potassium salt. 8.0 g (63%) of material 559e could be obtained.

P-4- 559 of synthesis

The procedure was the same as the synthesis of K-7-334, except that 1.2 equivalents of 559e and chlorosulfonyl isocyanate were used instead of 334d. 6.8 g (83%) of material P-4-559 was obtained.

Compound Q-1- 637 of synthesis

637b synthesis

The procedure was the same as the synthesis of 497d, except that 1b 7g instead of 497b and 637a instead of 497c were used. 14.1 g (80%) of material 637b could be obtained.

637c synthesis

The procedure was the same as the synthesis of 497e, except that 637b was used instead of 497d and methylcyclohexyltrifluoroboron potassium salt was used instead of cyclopropyltrifluoroboron potassium salt. 10.1 g (61%) of material 637c was obtained.

637d synthesis

The procedure was the same as the synthesis of K-7-334, except that 1.2 equivalents of 637c and chlorosulfonyl isocyanate were used instead of 334d. 8.0 g (78%) of material 637d could be obtained.

Q-1- 637 of synthesis

The procedure was the same as the synthesis of L-13-330, except that 637d was used instead of 330e. 5.7 g (71%) of material Q-1-637 could be obtained.

Compound Q-5- 51 of synthesis

51a of synthesis

The procedure was the same as the synthesis of 497d, except that 559b 7g instead of 497b and benzenesiol were used instead of 497c. 5.9 g (75%) of material 51a could be obtained.

51b of synthesis

The procedure was the same as in the synthesis of 497e except that 51a was used instead of 497d and methylcyclohexyltrifluoroboron potassium salt was used instead of cyclopropyltrifluoroboron potassium salt. 4.6 g (58%) of material 51b could be obtained.

51c of synthesis

The procedure was the same as the synthesis of 330e, except that 51b was used instead of 330d. 5.1 g (83%) of material 51c could be obtained.

51d of synthesis

5.1 g of 51c and 2.1 equivalents of benzene boronic acid were dissolved in a tetrahydrofuran solvent, and 4 equivalents of potassium carbonate was dissolved in water and stirred with heating. Add 0.03 equivalent of tetrakistriphenylphosphine palladium catalyst and confirm the reaction. When the reaction is complete, extraction is performed with water and chloroform, and the organic layer is dried using magnesium sulfate. After distillation under reduced pressure to remove the solvent, recrystallization using methanol. 3.5 g (78%) of material 51d could be obtained.

Q-5- 51 of synthesis

The procedure was the same as the synthesis of L-13-330, except that 51d was used instead of 330e. 2.5 g (72%) of material Q-5-51 could be obtained.

Compound Q-10- 552 of synthesis

552a synthesis

The procedure was the same as the synthesis of 497a, except that 10 g of 2-trifluoromethylbenzaldehyde was used instead of dibenzofuran-2-aldehyde. 8.2 g (43%) of material 552a could be obtained.

552b synthesis

The procedure was the same as the synthesis of 497b, except that 552a was used instead of 497a. 7.1 g (51%) of material 552b could be obtained.

552d synthesis

The procedure was the same as the synthesis of 497d, except that 552b instead of 497b and 552c instead of 497c were used. It was possible to obtain 10.3 g (82%) of substance 552d.

552e synthesis

The procedure was the same as in the synthesis of 497e except that 552d was used instead of 497d and methylcyclohexyltrifluoroboron potassium salt was used instead of cyclopropyltrifluoroboron potassium salt. 7.4 g (59%) of substance 552e could be obtained.

552f synthesis

The procedure was the same as the synthesis of 330e, except that 552e was used instead of 330d. 7.4 g (82%) of material 552f could be obtained.

552 g synthesis

Synthesis was performed in the same manner, except that 552f instead of 51c and dibenzofuranboronic acid were used instead of benzeneboronic acid. 552 g of the material, 6.4 g (82%), could be obtained.

Q-10- 552 of synthesis

The procedure was the same as the synthesis of L-13-330, except that 552g was used instead of 330e. 4.3 g (68%) of material Q-10-552 was obtained.

Compound Q-16- 444 of synthesis

Of 444b synthesis

The procedure was the same as the synthesis of 497d, except that 131b 8g instead of 497b and 444a instead of 497c were used. 11.3 g (85%) of material 444b could be obtained.

Of 444c synthesis

The procedure was the same as in the synthesis of 497e except that 444b was used instead of 497d and methylcyclohexyltrifluoroboron potassium salt was used instead of cyclopropyltrifluoroboron potassium salt. 8.8 g (62%) of material 444c could be obtained.

Of 444d synthesis

Dichloromethane is added to the supernatant filled with nitrogen and the temperature is reduced to 0°C. Add 20 equivalents of phosphorus oxychloride and 20 equivalents of dimethylformamide, slowly raise to room temperature and stir for about 1 hour. 8.8 g of 444c dissolved in dichloromethane was added to the above vial, followed by stirring under heating. TLC check is performed after treating the mixed solution with sodium bicarbonate. After the reaction is completed, cool to room temperature and lower the temperature to 0℃ to adjust the pH with an aqueous sodium bicarbonate solution. After neutralization, the organic layer is extracted with chloroform and dried using magnesium sulfate. After distillation under reduced pressure to remove the solvent, recrystallization using methanol. 6.3 g (68%) of material 444d was obtained.

Of 444e synthesis

After dissolving 444 g of 6.3 g in tetrahydrofuran, add 5 equivalents of sulfamic acid dissolved in water and stir for 30 minutes. Thereafter, 2.2 equivalents of sodium chlorite dissolved in water was added, and the reaction was confirmed after about 10 minutes. When the reaction is complete, add an aqueous sodium cysulfate solution and stir sufficiently. After extraction using chloroform, the organic layer is dried over magnesium sulfate. After distillation under reduced pressure to remove the solvent, recrystallization using ethanol. 4.0 g (63%) of substance 444e could be obtained.

Of 444f synthesis

After dissolving 4.0 g of 444e and 2.05 equivalents of coumarin in chloroform, add 1.1 equivalents of EDC-HCl and 1.1 equivalents of DMAP and stir with heating. After the reaction is completed, it is cooled to room temperature, water is added, and the resulting solid is filtered. The solid is dissolved again in chloroform to remove moisture with magnesium sulfate and distilled under reduced pressure to remove the solvent. Recrystallization using methanol afforded 3.6 g (72%) of material 444f.

Q-16- 444 of synthesis

The procedure was the same as the synthesis of L-13-330, except that 444f was used instead of 330e. 2.6g (73%) of material Q-16-444 could be obtained.

Compound Q-19- 359 of synthesis

359a synthesis

The procedure was the same as the synthesis of 497a, except that 10 g of 2-isopropylbenzaldehyde was used instead of dibenzofuran-2-aldehyde. 8.5 g (41%) of material 359a could be obtained.

359b synthesis

The procedure was the same as the synthesis of 497b, except that 359a was used instead of 497a. 7.0 g (55%) of material 359b could be obtained.

359c synthesis

The procedure was the same as the synthesis of 497d, except that 359b instead of 497b and 2,6-diisopropylphenol was used instead of 497c. 8.8 g (83%) of material 359c could be obtained.

359d of synthesis

The procedure was the same as the synthesis of 497e, except that 359c was used instead of 497d and methylcyclohexyltrifluoroboron potassium salt was used instead of cyclopropyltrifluoroboron potassium salt. 6.2g (56%) of 359d material could be obtained.

359e synthesis

The procedure was the same as the synthesis of 330e, except that 359d was used instead of 330d. 6.4 g (82%) of material 359e could be obtained.

359f of synthesis

Synthesis was performed in the same manner, except that 359e instead of 51c and 1-naphthaleneboronic acid was used instead of benzene boronic acid. 5.0 g (79%) of material 359f could be obtained.

Q-19- 359 of synthesis

The procedure was the same as the synthesis of L-13-330, except that 359f was used instead of 330e. 3.6g (72%) of material Q-19-359 could be obtained.

Compound R-1- 590 of synthesis

590b synthesis

The procedure was the same as the synthesis of 497d, except that 1b 5g instead of 497b and 590a instead of 497c were used. 10.4 g (84%) of material 590b could be obtained.

590c synthesis

The procedure was the same as the synthesis of 497e, except that 590b was used instead of 497d and methylcyclohexyltrifluoroboron potassium salt was used instead of cyclopropyltrifluoroboron potassium salt. 6.9 g (59%) of material 590c could be obtained.

590d synthesis

The procedure was the same as the synthesis of K-7-334, except that 590c was used instead of 334d. 5.9 g (83%) of material 590d could be obtained.

R-1- 590 of synthesis

The procedure was the same as the synthesis of C-26-497, except that 590d was used instead of 497e. 4.3 g (64%) of material R-1-590 could be obtained.

Compound S-19- 4 of synthesis

4a of synthesis

The procedure was the same as the synthesis of 497d, except that 359b 8g instead of 497b and 2-methoxyphenol were used instead of 497c. 76 g (81%) of material 4a could be obtained.

4b of synthesis

The procedure was the same as the synthesis of 497e except that 4a was used instead of 497d and methylcyclohexyltrifluoroboron potassium salt was used instead of cyclopropyltrifluoroboron potassium salt. 5.9 g (58%) of material 4b could be obtained.

S-19- 4 of synthesis

The procedure was the same as the synthesis of I-17-131, except that 5.9 g of 4b was used instead of 131 d. 3.6 g (46%) of material S-19-4 could be obtained.

Compound T-10- 26 of synthesis

26a of synthesis

The procedure was the same as the synthesis of 497d, except that 552b 5g instead of 497b and phenol was used instead of 497c. 4.2 g (80%) of material 26a was obtained.

26b of synthesis

The procedure was the same as the synthesis of 497e except 26a was used instead of 497d and methylcyclohexyltrifluoroboron potassium salt was used instead of cyclopropyltrifluoroboron potassium salt. 3.6 g (63%) of material 26b could be obtained.

26c of synthesis

The procedure was the same as the synthesis of K-7-334, except that 26b was used instead of 334d. 3.0 g (79%) of material 26c could be obtained.

T-10- 26 of synthesis

The procedure was the same as the synthesis of J-30-3, except that 26c was used instead of 3d. 2.3 g (53%) of the substance T-10-26 was obtained.

Compound U-4- 316 of synthesis

316a synthesis

The procedure was the same as the synthesis of 497d, except that 559b instead of 497b and 2,4-difluorophenol instead of 497c were used. Material 316a g (74%) was obtained.

U-4- 316 of synthesis

The procedure was the same as the synthesis of 497e, except that 316a was used instead of 497d and methylcyclohexyltrifluoroboron potassium salt was used instead of cyclopropyltrifluoroboron potassium salt. 4.3 g (62%) of material U-4-316 could be obtained.

Compound V-1- 489 of synthesis

489a synthesis

The procedure was the same as the synthesis of 497d except that 1b 8g instead of 497b and 2,4-di(trifluoromethyl)phenol was used instead of 497c. 11.5 g (85%) of material 489a could be obtained.

489b synthesis

The procedure was the same as the synthesis of 497e except that 489a was used instead of 497d and isopropylcyclohexyltrifluoroboron potassium salt was used instead of cyclopropyltrifluoroboron potassium salt. 9.2g (60%) of material 489b could be obtained.

489c synthesis

The procedure was the same as the synthesis of K-7-334, except that instead of 334d, 489b, 1.2 equivalents of chlorosulfonyl isocyanate was used. 7.7 g (82%) of material 489c could be obtained.

489d synthesis

Synthesis was performed in the same manner as 444d, except that instead of 444c, 489c, POCl3, and DMF were used in 5 equivalents, respectively. 5.5 g (70%) of material 489d could be obtained.

Of 489e synthesis

Synthesis was carried out in the same manner as in 444e, except that instead of 444d, 489d, 3 equivalents of sulfamic acid and 1.1 equivalents of sodium chlorite were used. 3.5 g (64%) of material 489e could be obtained.

489f synthesis

Synthesis was performed in the same manner as 444f, except that 489e instead of 444e and 1.05 equivalent of phenol instead of coumarin were used. 2.7 g (74%) of material 489f could be obtained.

V-1- 489 of synthesis

The procedure was the same as the synthesis of L-13-330, except that 489 was used instead of 330e. 1.9 g (72%) of material V-1-489 could be obtained.

Compound Y-19- 413 of synthesis

413a synthesis

The procedure was the same as the synthesis of 497d, except that 359b instead of 497b and t-butylphenol were used instead of 497c. 10.6 g (82%) of material 413a was obtained.

413b synthesis

The procedure was the same as the synthesis of 497e, except that 413a was used instead of 497d and isopropylcyclohexyltrifluoroboron potassium salt was used instead of cyclopropyltrifluoroboron potassium salt. 9.1 g (61%) of material 413b could be obtained.

413c synthesis

Synthesis was carried out in the same manner as 444d, except that 5 equivalents of 413b, POCl3 and DMF were used instead of 444c. 6.7 g (72%) of material 413c was obtained.

413d synthesis

The procedure was the same as the synthesis of 330e, except that 1.2 equivalents of 413c and N-iodosuccinimide were used instead of 330d. 5.9 g (78%) of material 413d could be obtained.

413e synthesis

Synthesis was performed in the same manner as in 444e, except that 413d instead of 444d, 3 equivalents of sulfamic acid, and 1.1 equivalents of sodium chlorite were used. 3.8 g (67%) of material 413e could be obtained.

413f synthesis

Synthesis was performed in the same manner as 444f, except that instead of 444e, 413e and 1.05 equivalents of coumarin were used. 3.1 g (73%) of material 413f could be obtained.

Y-19- 413 of synthesis

The procedure was the same as the synthesis of J-30-3, except that 413f was used instead of 3d. 2.2 g (54%) of material Y-19-413 could be obtained.

Example One

A first solution was prepared by dissolving compound C-26-497, which is an organic fluorescent substance, in a solvent xylene.

A second solution was prepared by dissolving a thermoplastic resin SAN (styrene-acrylonitrile-based) in a solvent xylene. The first solution and the second solution were mixed so that the amount of the organic phosphor was 0.5 parts by weight based on 100 parts by weight of the SAN, and homogeneously mixed. The solid content in the mixed solution was 20% by weight and the viscosity was 200 chen. This solution was coated on a PET substrate and dried to prepare a color conversion film.

The luminance spectrum of the prepared color conversion film was measured with a spectroradiometer (TOPCON SR series). Specifically, the prepared color conversion film is laminated on one side of the light guide plate of the backlight unit including the LED blue backlight (maximum light emission wavelength 450 nm) and the light guide plate, and after laminating the prism sheet and the DBEF film on the color conversion film, the film The luminance spectrum was measured. When measuring the luminance spectrum, the initial value was set so that the brightness of the blue LED light was 600 nits based on the w/o color conversion film.

Example 2

It was carried out in the same manner as in Example 1, except that Compound I-17-131 was used instead of Compound C-26-497.

Example 3

It was carried out in the same manner as in Example 1, except that Compound J-30-3 was used instead of Compound C-26-497.

Example 4

It was carried out in the same manner as in Example 1, except that Compound K-2-1 was used instead of Compound C-26-497.

Example 5

It was carried out in the same manner as in Example 1, except that Compound K-7-334 was used instead of Compound C-26-497.

Example 6

It was carried out in the same manner as in Example 1, except that Compound L-13-330 was used instead of Compound C-26-497.

Example 7

It was carried out in the same manner as in Example 1, except that Compound L-36-5 was used instead of Compound C-26-497.

Example 8

It was carried out in the same manner as in Example 1, except that Compound P-1-106 was used instead of Compound C-26-497.

Example 9

It was carried out in the same manner as in Example 1, except that Compound P-4-559 was used instead of Compound C-26-497.

Example 10

It was carried out in the same manner as in Example 1, except that Compound Q-1-637 was used instead of Compound C-26-497.

Example 11

It was carried out in the same manner as in Example 1, except that Compound Q-5-51 was used instead of Compound C-26-497.

Example 12

It was carried out in the same manner as in Example 1, except that Compound Q-10-552 was used instead of Compound C-26-497.

Example 13

It was carried out in the same manner as in Example 1, except that Compound Q-16-444 was used instead of Compound C-26-497.

Example 14

It was carried out in the same manner as in Example 1, except that Compound Q-19-359 was used instead of Compound C-26-497.

Example 15

It was carried out in the same manner as in Example 1, except that Compound R-1-590 was used instead of Compound C-26-497.

Example 16

It was carried out in the same manner as in Example 1, except that Compound S-19-4 was used instead of Compound C-26-497.

Example 17

It was carried out in the same manner as in Example 1, except that Compound T-10-26 was used instead of Compound C-26-497.

Example 18

It was carried out in the same manner as in Example 1, except that Compound U-4-316 was used instead of Compound C-26-497.

Example 19

It was carried out in the same manner as in Example 1, except that Compound V-1-489 was used instead of Compound C-26-497.

Example 20

It was carried out in the same manner as in Example 1, except that Compound Y-19-413 was used instead of Compound C-26-497.

Comparative example One

It was carried out in the same manner as in Example 1, except that the following compound diPh was used instead of Compound C-26-497.

Comparative example 2

It was carried out in the same manner as in Example 1, except that the following compound diPhO was used instead of Compound C-26-497.

compound Solution (Toluene) Film PLQY (%) Abs. Intensity
(1000h, %) _max (Abs) _max (PL) _max (PL) Example 1 C-26-497 588 606 622 81 87 Example 2 I-17-131 585 603 618 83 90 Example 3 J-30-3 604 620 634 75 92 Example 4 K-2-1 572 585 602 84 93 Example 5 K-7-334 512 528 542 92 94 Example 6 L-13-330 519 534 549 85 94 Example 7 L-36-5 606 624 639 79 97 Example 8 P-1-106 507 520 538 94 95 Example 9 P-4-559 509 522 540 95 98 Example 10 Q-1-637 507 523 540 95 96 Example 11 Q-5-51 584 600 617 86 97 Example 12 Q-10-552 508 526 544 94 96 Example 13 Q-16-444 507 524 539 93 95 Example 14 Q-19-359 513 529 546 94 98 Example 15 R-1-590 514 530 546 92 96 Example 16 S-19-4 515 531 545 90 97 Example 17 T-10-26 510 527 545 91 96 Example 18 U-4-316 503 519 533 94 98 Example 19 V-1-489 504 521 537 93 97 Example 20 Y-19-413 519 536 552 92 98 Comparative Example 1 diPh 573 605 622 90 52 Comparative Example 2 diPhO 521 537 550 32 73

According to Table 4 above, it can be seen that the compound according to the exemplary embodiment of the present specification has higher stability to light than the comparative example.

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

Claims (6)

Compound represented by the formula (1):
[Formula 1]

In Chemical Formula 1,
X1 and X2 are each independently a halogen group; Cyano group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted ester group; And a substituted or unsubstituted alkynyl group.
X3 and X4 are each independently selected from the group consisting of O, S and Se,
R1 and R7 are each independently a substituted or unsubstituted aryl group; And a substituted or unsubstituted heterocyclic group.
R2 and R6 are each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted ester group; A substituted or unsubstituted aryl group; And it is any one selected from the group consisting of a heterocyclic group,
R3 and R5 are each independently a cycloalkyl group unsubstituted or substituted with an alkyl group,
R4 is a substituted or unsubstituted phenyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted dibenzofuran group; And a substituted or unsubstituted dibenzothiophene group. The method according to claim 1, X1 and X2 are each independently a fluorine group; Cyano group; A substituted or unsubstituted ester group; Or a substituted or unsubstituted alkynyl group. The method according to claim 1, Formula 1 is a compound represented by any one of the following Table 1, Table 2, and Table 3-1 to Table 3-7:
[Table 1]

[Table 2]

[Table 3-1]

[Table 3-2]

[Table 3-3]

[Table 3-4]

[Table 3-5]

[Table 3-6]

[Table 3-7]

. Resin matrix; And a compound according to any one of claims 1 to 3 dispersed in the resin matrix. A backlight unit comprising the color conversion film according to claim 4. A display device comprising the backlight unit according to claim 5.

Images