KR20210009884A - Compound, photoresist fluorescent resin composition comprising same, color conversion film, backlight unit and display apparatus - Google Patents

Abstract

The present invention relates to a compound represented by chemical formula 1, to a photosensitive fluorescent resin composition comprising the same, to a color conversion film manufactured therefrom, to a backlight unit, and to a display device. The compound has high solubility.

Description

A compound, a photosensitive fluorescent resin composition containing the same, a color conversion film, a backlight unit, and a display device TECHNICAL FIELD {COMPOUND, PHOTORESIST FLUORESCENT RESIN COMPOSITION COMPRISING SAME, COLOR CONVERSION FILM, BACKLIGHT UNIT AND DISPLAY APPARATUS}

The present specification relates to a compound, a photosensitive fluorescent resin composition including the same, a color conversion film manufactured therefrom, a backlight unit, and a display device.

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

In order to overcome this decrease in color reproduction rate and reduce production cost, a method of implementing green and red by forming a film and combining it with 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 quantum dots. In addition, quantum dots have a disadvantage in that their stability against oxygen and water is poor, and their performance is significantly deteriorated when aggregated. In addition, it is difficult to keep the size constant during the production of quantum dots, so the production cost is high.

Existing BF ₂ or B(CN) ₂ based bodiphy-structured compounds are fluorescent dyes with high light efficiency and narrow half width. They provide excellent optical properties when applied to color conversion films, but are insufficient in light resistance and heat resistance for commercialization. There is a need to develop a compound having high durability.

The present specification is to provide a compound, a photosensitive fluorescent resin composition including the same, a color conversion film manufactured therefrom, a backlight unit, and a display device.

The present specification provides a compound represented by the following formula (1).

[Formula 1]

In Formula 1,

X1 and X2 are the same as or different from each other, and each independently O; Or NR1,

A1 and A5 are the same as or different from each other, and each independently -CR2R3-; -C(=O)-; Or a substituted or unsubstituted hydrocarbon ring,

A2 and A6 are the same as or different from each other, and each independently -CR2R3-; -S-; -O-; -NR4-; Or a substituted or unsubstituted hydrocarbon ring,

A3 and A7 are the same as or different from each other, and each independently -CR2R3-; Or a substituted or unsubstituted hydrocarbon ring,

A4 and A8 are the same as or different from each other, and each independently -CR2R3-; -S-; -O-; -NR4-; -N=; =N-; =CR5-; -CR6=; -C(=O)-; Or a substituted or unsubstituted hydrocarbon ring,

R2 and R3 are the same as or different from each other, and each independently hydrogen; Halogen group; Cyano group; Hydroxy group; Nitro group; Mercapto group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or R2 and R3 are bonded to each other to form a substituted or unsubstituted ring,

R5 and R6 are the same as or different from each other, and each independently hydrogen; Halogen group; Cyano group; Hydroxy group; Nitro group; Mercapto group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

n1 to n4 are each independently 0 or 1,

R1, R4, and M1 to M20 are the same as or different from each other, and each independently hydrogen; Halogen group; Cyano group; Hydroxy group; Nitro group; Mercapto group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; Or a substituent represented by the following formula (2),

At least one selected from the group consisting of R1, R4 and M1 to M20 is each independently a substituent represented by the following formula (2),

[Formula 2]

In Chemical Formula 2,

X3 is a direct bond; O; C(=O)NH; Or NH,

L is a substituted or unsubstituted alkylene group; A substituted or unsubstituted cycloalkylene group; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,

a is an integer from 0 to 2,

l is 1 or 2,

E is a polymerizable group,

* Indicates the bonding position,

When a and l are each 2, the structures in parentheses are the same or different from each other.

In addition, the present specification is a binder resin; Polyfunctional monomers; And it provides a photosensitive fluorescent resin composition comprising the compound described above.

In addition, the present specification provides a color conversion film including the above-described compound combined with a binder resin.

In addition, the present specification provides a backlight unit including the color conversion film described above.

Further, the present specification provides a display device including the above-described backlight unit.

The compound according to an exemplary embodiment of the present specification is capable of high color reproduction.

The compound according to an exemplary embodiment of the present specification has high solubility.

The compound according to an exemplary embodiment of the present specification has high light resistance.

The compound according to an exemplary embodiment of the present specification has the advantage of not being transfected.

1 is a schematic diagram in which a color conversion film according to an exemplary embodiment of the present specification is applied to a backlight unit.
2 is a schematic diagram illustrating a structure of a display device according to an exemplary embodiment of the present specification.

Hereinafter, the present specification will be described in detail.

The present specification provides a compound represented by Chemical Formula 1.

Conventional perylene derivatives have a limitation in reproducing high color because their absorption and emission wavelengths are short. In addition, conventional perylene derivatives have disadvantages of poor migrating and light resistance.

On the other hand, the compound according to an exemplary embodiment of the present specification is capable of high color reproduction by shifting absorption and emission wavelengths to a longer wavelength compared to the conventional perylene derivatives. Specifically, the compound according to the exemplary embodiment of the present specification is capable of high color reproduction because absorption and emission wavelengths are shifted to a longer wavelength compared to the conventional perylene derivatives, thereby implementing a wider range of color coordinates.

The compound according to an exemplary embodiment of the present specification has excellent light resistance compared to a conventional perylene derivative. Specifically, the compound according to an exemplary embodiment of the present specification has excellent light resistance because it has an electron withdrawing group at the imide position compared to the conventional perylene derivative.

The compound according to an exemplary embodiment of the present specification has a reactive group capable of polymerizing with a binder in a molecule, and thus has an advantage of not being transferred by binding to a binder.

In the present specification, when a part "includes" a certain component, it means that other components may be further included rather than excluding other components unless otherwise stated.

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

In the present specification, the "adjacent" group means a substituent substituted on an atom directly connected to the atom where the corresponding substituent is substituted, a substituent positioned three-dimensionally closest to the corresponding substituent, or another substituent substituted on the atom where the corresponding substituent is substituted. I can. For example, two substituents substituted at an ortho position in a benzene ring and two substituents substituted at the same carbon in an aliphatic ring may be interpreted as "adjacent" groups to each other.

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

The term "substituted" 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 as long as the position where the hydrogen atom is substituted, that is, the position where the substituent can be substituted, and when two or more are substituted , Two or more substituents may be the same or different from each other.

In the present specification, the term "substituted or unsubstituted" refers to deuterium; Halogen group; Cyano group; Nitro group; Hydroxy group; Imide group; Amide group; A substituted or unsubstituted amine group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted haloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; Substituted with one or two or more substituents selected from the group consisting of a substituted or unsubstituted aryl group and a substituted or unsubstituted heterocyclic group, or substituted with a substituent to which two or more substituents are connected among the exemplified substituents, or do not have any substituents Means that.

In the present specification, examples of the halogen group include fluorine, chlorine, bromine, or iodine.

In the present specification, the number of carbon atoms of the imide group is not particularly limited, but it 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 the present specification, the amine group is -NH ₂ ; Monoalkylamine group; Dialkylamine group; N-alkylarylamine group; Monoarylamine group; Diarylamine group; N-arylheteroarylamine group; It may be selected from the group consisting of an N-alkylheteroarylamine group, a monoheteroarylamine group, and a diheteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30.

In the present specification, the N-alkylarylamine group refers to an amine group in which an alkyl group and an aryl group are substituted with N of the amine group.

In the present specification, the N-arylheteroarylamine group refers to an amine group in which an aryl group and a heteroaryl group are substituted with N of the amine group.

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

In the present specification, the alkyl group in the alkylamine group, N-alkylarylamine group, and N-alkylheteroarylamine group is the same as the examples of the alkyl group described later.

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 alkyl group may be a linear or branched chain, and the number of carbon atoms 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, 4-methylhexyl, 5-methylhexyl, and the like, but are not limited thereto.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 30 carbon atoms, and 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, etc., but are limited thereto. It is not.

In the present specification, a haloalkyl group represents an alkyl group in which one or more hydrogen atoms of the alkyl group are replaced with the same or different halogen groups. The haloalkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 10. Specific examples include -CH ₂ Cl, -CF ₃ , -CH ₂ CF ₃ , -CF ₂ CF ₃ , but are not limited thereto.

In the present specification, the alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but it is preferably 1 to 30 carbon atoms.

In the present specification, the alkenyl group may be a linear or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30.

In the present specification, the alkynyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30. Specific examples include an alkynyl group such as ethynyl, propynyl, 2-methyl-2propynyl, 2-butynyl, and 2-pentynyl, but are 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, the number of carbon atoms is not particularly limited, but it 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, but is preferably 10 to 30 carbon atoms. Specifically, the polycyclic aryl group may be a naphthyl group, an anthracenyl group, a phenanthryl group, a triphenyl group, a pyrenyl group, a perylenyl group, a chrysenyl group, a fluorenyl group, and the like, but is not limited thereto.

In the present specification, the fluorenyl group may be substituted, and adjacent groups may be bonded to each other to form a ring.

,

,

및

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

,

,

And

Etc. However, it is not limited thereto.

In the present specification, the heterocyclic group includes at least one atom or hetero atom other than carbon, and specifically, the hetero atom may include at least one atom selected from the group consisting of O, N, Se, and S. The number of carbon atoms is not particularly limited, but is preferably 2 to 30 carbon atoms, and the heterocyclic group may be monocyclic or polycyclic. Examples of the heterocyclic group include thiophene group, furanyl group, pyrrole group, imidazolyl group, thiazolyl group, oxazolyl group, oxadiazolyl group, pyridyl group, bipyridyl group, pyrimidyl group, triazinyl group, tria Zolyl group, acridyl 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, p Nanthrolinyl group (phenanthroline), thiazolyl group, isoxazolyl group, oxadiazolyl group, thiadiazolyl group, phenothiazinyl group, dibenzofuranyl group, and the like, but are not limited thereto.

In the present specification, the description of the heterocyclic group described above may be cited except that the heteroaryl group is an aromatic heterocyclic group.

In the exemplary embodiment of the present specification, the polymerizable group may have at least one selected from the group consisting of a substituted or unsubstituted ethylenically unsaturated group, a substituted or unsubstituted siloxane group, and a substituted or unsubstituted epoxy group.

The polymerizable group may have any one of the following structures.

In the above structure,

Z1 and Z2 are each independently hydrogen, a halogen group, or a substituted or unsubstituted alkyl group,

Z3 to Z5 are each independently a substituted or unsubstituted alkyl group,

* Indicates the bonding position.

In an exemplary embodiment of the present specification, Formula 1 may be represented by the following Formula 3.

[Formula 3]

In Chemical Formula 3, X1, X2, A1 to A8, n1 to n4, and M1 to M5 are as defined in Chemical Formula 1.

In an exemplary embodiment of the present specification, at least one selected from the group consisting of any one of M1 to M5, any one of M6 to M10, any one of M11 to M15, any one of M16 to M20, and R1 is each independently It may be a substituent represented by Chemical Formula 2.

In an exemplary embodiment of the present specification, any one of M1 to M5, any one of M6 to M10, any one of M11 to M15, and any one of M16 to M20 are each independently a substituent represented by Formula 2, and the rest Can be hydrogen.

In the exemplary embodiment of the present specification, R1 may be a substituent represented by Chemical Formula 2.

In the exemplary embodiment of the present specification, R1 and R4 may each independently be a substituent represented by Chemical Formula 2.

In the exemplary embodiment of the present specification, Formula 1 may be represented by any one of the following Formulas 4 to 6.

[Formula 4]

[Formula 5]

[Formula 6]

In Formulas 4 to 6, X1 to X2, A1 to A8, and n1 to n4 are as defined in Formula 1, and X3, L, E, l and a are as defined in Formula 2,

M1 to M5 are the same as or different from each other, and each independently hydrogen; Halogen group; Cyano group; Hydroxy group; Nitro group; Mercapto group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In the exemplary embodiment of the present specification, X1 and X2 are the same as or different from each other, and each independently O; Or NR1.

In the exemplary embodiment of the present specification, X1 and X2 are O.

In the exemplary embodiment of the present specification, X1 and X2 are NR1, R1 is the same as or different from each other, and each independently hydrogen; Halogen group; Cyano group; Hydroxy group; Nitro group; Mercapto group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; Or a substituent represented by Chemical Formula 2.

In the exemplary embodiment of the present specification, X1 and X2 are NR1, R1 is the same as or different from each other, and each independently a substituent represented by Formula 2; Hydrogen; Halogen group; Hydroxy group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

In the exemplary embodiment of the present specification, X1 and X2 are NR1, R1 is the same as or different from each other, and each independently a substituent represented by Formula 2; Hydrogen; An alkyl group unsubstituted or substituted with a substituent selected from the group consisting of an aryl group and a heteroaryl group; Haloalkyl group; Aryl group; A substituted or unsubstituted cycloalkyl group; Furanyl group; Pyridyl group; Pyrimidyl group; Or a triazinyl group.

In the exemplary embodiment of the present specification, X1 and X2 are NR1, R1 is the same as or different from each other, and each independently a substituent represented by Formula 2; Hydrogen; An alkyl group unsubstituted or substituted with a substituent selected from the group consisting of a phenyl group, a pyridyl group, a furanyl group, and a thiophenyl group; Haloalkyl group; Phenyl group; Naphthyl group; Cyclohexyl group; Cyclopentyl group; Furanyl group; Pyridyl group; Pyrimidyl group; Or a triazinyl group.

In the exemplary embodiment of the present specification, A1 and A5 are the same as or different from each other, and each independently -CR2R3-; -C(=O)-; Or a substituted or unsubstituted hydrocarbon ring, R2 and R3 are the same as or different from each other, and each independently hydrogen; Halogen group; Cyano group; Hydroxy group; Nitro group; Mercapto group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or R2 and R3 are bonded to each other to form a substituted or unsubstituted ring.

In the exemplary embodiment of the present specification, A1 and A5 are the same as or different from each other, and each independently -CR2R3-; -C(=O)-; A substituted or unsubstituted benzene ring; A substituted or unsubstituted naphthalene ring; Substituted or unsubstituted dihydroindene ring; A substituted or unsubstituted indene ring; Or a substituted or unsubstituted cyclopentadiene ring.

In the exemplary embodiment of the present specification, A2 and A6 are the same as or different from each other, and each independently -CR2R3-; -S-; -O-; -NR4-; Or a substituted or unsubstituted hydrocarbon ring, R2 and R3 are the same as or different from each other, and each independently hydrogen; Halogen group; Cyano group; Hydroxy group; Nitro group; Mercapto group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or R2 and R3 combine with each other to form a substituted or unsubstituted ring, R4 is hydrogen; Halogen group; Cyano group; Hydroxy group; Nitro group; Mercapto group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; Or a substituent represented by the following formula (2).

In the exemplary embodiment of the present specification, A2 and A6 are the same as or different from each other, and each independently -CR2R3-; -S-; -O-; -NR4-; A substituted or unsubstituted benzene ring; A substituted or unsubstituted naphthalene ring; Substituted or unsubstituted dihydroindene ring; A substituted or unsubstituted indene ring; Or a substituted or unsubstituted cyclopentadiene ring.

In the exemplary embodiment of the present specification, A3 and A7 are the same as or different from each other, and each independently -CR2R3-; Or a substituted or unsubstituted hydrocarbon ring, R2 and R3 are the same as or different from each other, and each independently hydrogen; Halogen group; Cyano group; Hydroxy group; Nitro group; Mercapto group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or R2 and R3 are bonded to each other to form a substituted or unsubstituted ring.

In the exemplary embodiment of the present specification, A3 and A7 are the same as or different from each other, and each independently -CR2R3-; A substituted or unsubstituted benzene ring; A substituted or unsubstituted naphthalene ring; Substituted or unsubstituted dihydroindene ring; A substituted or unsubstituted indene ring; Or a substituted or unsubstituted cyclopentadiene ring.

In the exemplary embodiment of the present specification, A4 and A8 are the same as or different from each other, and each independently -CR2R3-; -S-; -O-; -NR4-; -N=; =N-; =CR5-; -CR6=; -C(=O)-; Or a substituted or unsubstituted hydrocarbon ring, R2 and R3 are the same as or different from each other, and each independently hydrogen; Halogen group; Cyano group; Hydroxy group; Nitro group; Mercapto group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or R2 and R3 combine with each other to form a substituted or unsubstituted ring, and R4 is hydrogen; Halogen group; Cyano group; Hydroxy group; Nitro group; Mercapto group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; Or a substituent represented by the following formula (2), R5 and R6 are the same as or different from each other, and each independently hydrogen; Halogen group; Cyano group; Hydroxy group; Nitro group; Mercapto group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In the exemplary embodiment of the present specification, A4 and A8 are the same as or different from each other, and each independently -CR2R3-; -S-; -O-; -NR4-; -N=; =N-; =CR5-; -CR6=; -C(=O)-; A substituted or unsubstituted benzene ring; A substituted or unsubstituted naphthalene ring; Substituted or unsubstituted dihydroindene ring; A substituted or unsubstituted indene ring; Or a substituted or unsubstituted cyclopentadiene ring.

In an exemplary embodiment of the present specification, R2 and R3 are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring; A substituted or unsubstituted aromatic hydrocarbon ring; Substituted or unsubstituted aliphatic heterocycle; Or it can form a substituted or unsubstituted aromatic heterocycle.

In an exemplary embodiment of the present specification, R2 and R3 are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring; A substituted or unsubstituted aromatic hydrocarbon ring; A substituted or unsubstituted aliphatic heterocycle including N, O and S heteroelements; Or N, O, and S heteroelements may be included and a substituted or unsubstituted aromatic heterocycle may be formed.

In an exemplary embodiment of the present specification, R2 and R3 are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring; A substituted or unsubstituted aromatic hydrocarbon ring; Substituted or unsubstituted aliphatic N-containing heterocycle; Substituted or unsubstituted aliphatic O-containing heterocycle; Substituted or unsubstituted aromatic N-containing heterocycle; Or it may form a substituted or unsubstituted aromatic O-containing heterocycle. At this time, hydrogen bonded to the nitrogen of the N-containing heterocycle may be substituted with a substituent represented by Formula 2 above.

In an exemplary embodiment of the present specification, R2 and R3 are bonded to each other to form a substituted or unsubstituted cyclohexane ring; Substituted or unsubstituted cyclopentane ring; A substituted or unsubstituted piperidine ring; Substituted or unsubstituted pyrrolidine ring; A substituted or unsubstituted tetrahydrofuran ring; Or a substituted or unsubstituted spiroundecan ring may be formed. In this case, hydrogen bonded to the nitrogen of the piperidine ring or hydrogen bonded to the nitrogen of the pyrrolidine ring may be substituted with a substituent represented by Formula 2 above.

및

에서 X1 또는 X2가 위치한 방향이며, 치환기의 왼쪽은 화학식 1의 페릴렌 구조에 결합되는 탄소 방향을 의미한다.-CR2R3- in the above substituent definition; -C(=O)-; -S-; -O-; -NR4-; -N=; =N-; =CR5-; And in -CR6=, the right side of the substituent is in Formula 1

And

Is the direction in which X1 or X2 is located, and the left side of the substituent refers to the carbon direction bonded to the perylene structure of Formula 1.

및

는 각각 독립적으로 하기 구조 중 어느 하나일 수 있다. In an exemplary embodiment of the present specification, in Formula 1

And

Each independently may be any one of the following structures.

In the above structure,

B1 to B144 are the same as or different from each other, and each independently hydrogen; Halogen group; Hydroxy group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

C1 to C57 are the same as or different from each other, and each independently, a substituent represented by Formula 2; Hydrogen; Halogen group; Hydroxy group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

* Indicates the bonding position.

In the exemplary embodiment of the present specification, B1 to B144 are the same as or different from each other, and each independently hydrogen; Halogen group; Hydroxy group; A substituted or unsubstituted alkoxy group; An alkyl group unsubstituted or substituted with a substituent selected from the group consisting of an aryl group and a heteroaryl group; Haloalkyl group; Cycloalkyl group; A substituted or unsubstituted aryl group; Furanyl group; Pyridyl group; Pyrimidyl group; Or a triazinyl group.

In the exemplary embodiment of the present specification, B1 to B144 are the same as or different from each other, and each independently hydrogen; Halogen group; Hydroxy group; Alkoxy group; An alkyl group unsubstituted or substituted with a substituent selected from the group consisting of a phenyl group, a pyridyl group, a furanyl group, and a thiophenyl group; Haloalkyl group; Phenyl group; Naphthyl group; Furanyl group; Pyridyl group; Pyrimidyl group; Or a triazinyl group.

In the exemplary embodiment of the present specification, C1 to C57 are the same as or different from each other, and each independently, a substituent represented by Formula 2; Hydrogen; An alkyl group unsubstituted or substituted with a substituent selected from the group consisting of an aryl group and a heteroaryl group; Haloalkyl group; Aryl group; A substituted or unsubstituted cycloalkyl group; Furanyl group; Pyridyl group; Pyrimidyl group; Or a triazinyl group.

In the exemplary embodiment of the present specification, C1 to C57 are the same as or different from each other, and each independently, a substituent represented by Formula 2; Hydrogen; An alkyl group unsubstituted or substituted with a substituent selected from the group consisting of a phenyl group, a pyridyl group, a furanyl group, and a thiophenyl group; Haloalkyl group; Phenyl group; Naphthyl group; Cyclohexyl group; Cyclopentyl group; Furanyl group; Pyridyl group; Pyrimidyl group; Or a triazinyl group.

In the exemplary embodiment of the present specification, the compound represented by Formula 1 is point symmetric, line symmetric, or face symmetric.

In the exemplary embodiment of the present specification, the compound represented by Formula 1 may be represented by any one of the following compounds.

In the above compound, Ph is a phenyl group.

The present specification is a binder resin; Polyfunctional monomers; And it provides a photosensitive fluorescent resin composition comprising the compound described above.

The content of the compound may be 0.005% by weight to 70% by weight based on the total weight of the solid content of the photosensitive fluorescent resin composition, but is not limited thereto.

The content of the compound may be 0.001% by weight to 15% by weight based on the total weight of the photosensitive fluorescent resin composition, but is not limited thereto.

The maximum absorption wavelength (λ _max ) of the compound may be 570 to 590 nm.

As the binder resin, a copolymer resin of a monomer imparting mechanical strength and a monomer imparting alkali solubility may be used.

Monomers that impart mechanical strength of the film include unsaturated carboxylic acid esters; Aromatic vinyls; Unsaturated ethers; Unsaturated imides; And it may be any one or more of an acid anhydride.

Specific examples of the unsaturated carboxylic acid esters are benzyl (meth) acrylate, methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, dimethylaminoethyl (meth) acrylate, isobutyl ( Meth)acrylate, t-butyl (meth)acrylate, cyclohexyl (meth)acrylate, isobornyl (meth)acrylate, ethylhexyl (meth)acrylate, 2-phenoxyethyl (meth)acrylate, tetra Hydrofurpril (meth)acrylate, hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 2-hydroxy-3-chloropropyl (meth)acrylate, 4-hydroxybutyl ( Meth)acrylate, acyloctyloxy-2-hydroxypropyl (meth)acrylate, glycerol (meth)acrylate, 2-methoxyethyl (meth)acrylate, 3-methoxybutyl (meth)acrylate, ethoxy Cydiethylene glycol (meth)acrylate, methoxytriethylene glycol (meth)acrylate, methoxytripropylene glycol (meth)acrylate, poly(ethylene glycol) methyl ether (meth)acrylate, phenoxydiethylene glycol (meth) )Acrylate, p-nonylphenoxypolyethylene glycol (meth)acrylate, p-nonylphenoxypolypropylene glycol (meth)acrylate, glycidyl (meth)acrylate, tetrafluoropropyl (meth)acrylate, 1,1,1,3,3,3-hexafluoroisopropyl (meth)acrylate, octafluoropentyl (meth)acrylate, heptadecafluorodecyl (meth)acrylate, tribromophenyl (meth) ) Acrylate, methyl α-hydroxymethyl acrylate, ethyl α-hydroxymethyl acrylate, propyl α-hydroxymethyl acrylate and butyl α-hydroxymethyl acrylate, but only these It is not limited.

Specific examples of the aromatic vinyls include styrene, α-methylstyrene, (o,m,p)-vinyl toluene, (o,m,p)-methoxy styrene, and (o,m,p)-chloro styrene. It may be selected from the group consisting of, but is not limited thereto.

Specific examples of the unsaturated ethers may be selected from the group consisting of vinyl methyl ether, vinyl ethyl ether, and allyl glycidyl ether, but are not limited thereto.

Specific examples of the unsaturated imides are selected from the group consisting of N-phenyl maleimide, N-(4-chlorophenyl) maleimide, N-(4-hydroxyphenyl) maleimide, and N-cyclohexyl maleimide. It can be, but is not limited to these.

Examples of the acid anhydride include maleic anhydride, methyl maleic anhydride, and tetrahydrophthalic anhydride, but are not limited thereto.

The monomer imparting alkali solubility may be a monomer containing an acid group. The acid group-containing monomer is at least one selected from the group consisting of (meth)acrylic acid, crotonic acid, itaconic acid, maleic acid, fumaric acid, monomethyl maleic acid, isoprene sulfonic acid, styrene sulfonic acid, 5-norbornene-2-carboxylic acid, etc. It can be used, but is not limited thereto.

The content of the binder resin may be 1% by weight or more and 60% by weight or less based on the total weight of the solid content of the photosensitive fluorescent resin composition, but is not limited thereto.

The content of the binder resin may be 1% by weight or more and 30% by weight or less based on the total weight of the photosensitive fluorescent resin composition, but is not limited thereto.

The acid value of the binder resin may be 50 KOH mg/g or more and 130 KOH mg/g or less, and the weight average molecular weight may be 1,000 g/mol or more and 40,000 g/mol or less, but is not limited thereto.

The polyfunctional monomer refers to a compound having two or more polymerizable functional groups, and serves as a crosslinking agent in the photosensitive fluorescent resin composition. Here, the polymerizable functional group is not particularly limited as long as polymerization is possible, but may be, for example, an ethylenic unsaturated group, a siloxane group, a hydroxy group, and an epoxy group. Specifically, the polyfunctional monomer may include an ethylenically unsaturated bond.

The polyfunctional monomers are ethylene glycol di(meth)acrylate, polyethylene glycol di(meth)acrylate having 2 to 14 ethylene groups, trimethylolpropane di(meth)acrylate, trimethylolpropane tri(meth)acrylate, penta Erythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, propylene glycol di(meth)acrylate having 2 to 14 propylene groups, dipentaerythritol penta(meth)acrylate and dipentaerythritol hexa(meth)acrylic It may be one or more selected from among the rates, but is not limited thereto.

The content of the multifunctional monomer may be 1% by weight to 60% by weight based on the total weight of the solid content of the photosensitive fluorescent resin composition, but is not limited thereto.

The content of the multifunctional monomer may be 1% to 30% by weight based on the total weight of the photosensitive fluorescent resin composition, but is not limited thereto.

The photosensitive fluorescent resin composition may further include a photoinitiator.

In the photosensitive fluorescent resin composition according to the present invention, the photoinitiator is an acetophenone compound; Biimidazole-based compounds; Triazine compounds; And it may be any one or more selected from the oxime compound.

As the acetophenone-based compound, 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1-(4-isopropylphenyl)-2-hydroxy-2-methylpropan-1-one, 4 -(2-hydroxyethoxy)-phenyl-(2-hydroxy-2-propyl) ketone, 1-hydroxycyclohexylphenyl ketone, benzoinmethyl ether, benzoinethyl ether, benzoinisobutyl ether, benzo Phosphate ether, 2,2-dimethoxy-2-phenylacetophenone, 2-methyl-(4-methylthio)phenyl-2-morpholino-1-propan-1-one, 2-benzyl-2-dimethyl Amino-1-(4-morpholinophenyl)-butan-1-one, or 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one, etc., It is not limited to this.

As the biimidazole-based compound, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenyl biimidazole, 2,2'-bis(o-chlorophenyl)- 4,4',5,5'-tetrakis(3,4,5-trimethoxyphenyl)-1,2'-biimidazole, 2,2'-bis(2,3-dichlorophenyl)-4 ,4',5,5'-tetraphenyl biimidazole, or 2,2'-bis(o-chlorophenyl)-4,4',5,5'-tetraphenyl-1,2'-biimidazole And the like, but are not limited thereto.

As the triazine-based compound, 3-{4-[2,4-bis(trichloromethyl)-s-triazine-6-yl]phenylthio}propionic acid, 1,1,1,3,3,3 -Hexafluoroisopropyl-3-{4-[2,4-bis(trichloromethyl)-s-triazine-6-yl]phenylthio}propionate, ethyl-2-{4-[2, 4-bis(trichloromethyl)-s-triazine-6-yl]phenylthio}acetate, 2-epoxyethyl-2-{4-[2,4-bis(trichloromethyl)-s-triazine- 6-yl]phenylthio}acetate, cyclohexyl-2-{4-[2,4-bis(trichloromethyl)-s-triazine-6-yl]phenylthio}acetate, benzyl-2-{4- [2,4-bis(trichloromethyl)-s-triazine-6-yl]phenylthio}acetate, 3-{chloro-4-[2,4-bis(trichloromethyl)-s-triazine- 6-yl]phenylthio}propionic acid, 3-{4-[2,4-bis(trichloromethyl)-s-triazine-6-yl]phenylthio}propionamide, 2,4-bis(trichloro Romethyl)-6-p-methoxystyryl-s-triazine, 2,4-bis(trichloromethyl)-6-(1-p-dimethylaminophenyl)-1,3,-butadienyl- s-triazine, or 2-trichloromethyl-4-amino-6-p-methoxystyryl-s-triazine, and the like, but are not limited thereto.

Examples of the oxime-based compound include CGI-242 and CGI-124 from Shiba in Japan, but are not limited thereto.

The content of the photoinitiator may be 0.1% by weight to 20% by weight based on the total weight of the solid content of the photosensitive fluorescent resin composition, but is not limited thereto.

The content of the photoinitiator may be 0.1% to 15% by weight based on the total weight of the photosensitive fluorescent resin composition, but is not limited thereto.

The photosensitive fluorescent resin composition may further include a solvent.

The photosensitive fluorescent resin composition according to an exemplary embodiment of the present invention may further include a solvent.

The solvent is acetone, methyl ethyl ketone, methyl isobutyl ketone, methyl cellosolve, ethyl cellosolve, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, propylene glycol dimethyl ether , Propylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, chloroform, methylene chloride, 1,2-dichloroethane, 1,1,1-trichloroethane, 1 ,1,2-trichloroethane, 1,1,2-trichloroethene, hexane, heptane, octane, cyclohexane, benzene, toluene, xylene, methanol, ethanol, isopropanol, propanol, butanol, t-butanol, 2 -Ethoxy propanol, 2-methoxy propanol, 3-methoxy butanol, cyclohexanone, cyclopentanone, propylene glycol methyl ether acetate, propene glycol ethyl ether acetate, 3-methoxybutyl acetate, ethyl 3-ethoxy Propionate, ethyl cellosolve acetate, methyl cellosolve acetate, butyl acetate, propylene glycol monomethyl ether, and dipropylene glycol may be one or more selected from the group consisting of monomethyl ether, but is not limited thereto.

Based on the total weight of the photosensitive fluorescent resin composition, the total solid content may be 10 wt% to 50 wt%, and the content of the solvent may be 50 wt% to 90 wt%, but is not limited thereto.

The photosensitive composition according to an exemplary embodiment of the present invention further comprises at least one additive selected from the group consisting of a dispersant, a curing accelerator, a thermal polymerization inhibitor, a surfactant, a photosensitizer, a plasticizer, an adhesion promoter, a filler, and an adhesion aid. I can.

The photosensitizers, plasticizers, adhesion promoters, fillers, and the like may also be used any compound that can be included in the conventional photosensitive fluorescent resin composition.

The content of the additives may each independently be 0.01% by weight to 5% by weight based on the total weight of the photosensitive fluorescent resin composition, but is not limited thereto.

The content of the additives may each independently be 0.01% by weight to 5% by weight based on the total weight of the solid content of the photosensitive fluorescent resin composition, but is not limited thereto.

The present specification provides a color conversion film including the above-described compound combined with a binder resin.

In more detail, a photosensitive material in the form of a thin film is formed by applying the photosensitive fluorescent resin composition of the present invention on a substrate in an appropriate manner.

The coating method is not particularly limited, but a spray method, a roll coating method, a spin coating method, or the like may be used, and generally, a spin coating method is widely used. Further, after forming the coating film, a part of the residual solvent can be removed under reduced pressure in some cases.

Light sources for curing the photosensitive fluorescent resin composition according to the present invention include, for example, mercury vapor arcs, carbon arcs, Xe arcs, etc. that emit light having a wavelength of 250 to 450 nm, but are not limited thereto.

When curing the photosensitive fluorescent resin composition, the compound represented by Formula 1 has a polymerizable group capable of binding to a binder resin. In this case, there is an advantage of no migration in the process.

The color conversion film of the present specification has a maximum emission peak in a region of 610 nm to 640 nm, specifically, a maximum emission peak in a region of 615 nm to 640 nm, and preferably 618 nm to 640 nm. In this case, there is an advantage of high color reproduction.

The half width of the maximum emission peak of the color conversion film of the present specification is 41 nm or less, and specifically, may be 35 nm or more and 41 nm or less. The half width means the width of the emission peak at half of the maximum height from the maximum emission peak of the emitted light when light absorbed from an external light source is converted to light of a different wavelength to emit light. This is excellent.

The color conversion film may further include an additional fluorescent material in addition to the compound represented by Chemical Formula 1. When a light source emitting blue light is used, 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 a light source emitting blue light and green light is used, the color conversion film may include only a red light emitting fluorescent material. However, the present invention is not limited thereto, and even when a light source emitting blue light is used, when a separate film including a green light emitting fluorescent material is laminated, the color conversion film may include only a red light emitting compound. Conversely, even when a light source emitting blue light is used, when a separate film including a red emitting fluorescent material is stacked, the color conversion film may include only a green light emitting compound.

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

It is preferable that the material of the resin matrix is a thermoplastic polymer or a thermosetting polymer. Specifically, as the material of the resin matrix, poly(meth)acrylic type such as polymethylmethacrylate (PMMA), polycarbonate type (PC), polystyrene type (PS), polyarylene type (PAR), polyurethane type (PU) ), styrene-acrylonitrile-based (SAN), polyvinylidene fluoride-based (PVDF), modified polyvinylidene fluoride-based (modified-PVDF), and the like may be used.

According to an exemplary embodiment of the present specification, the color conversion film according to the above-described exemplary embodiment further includes light diffusing particles. By dispersing the light-diffusion particles inside the color conversion film instead of the conventional light-diffusion film to improve the luminance, compared to using a separate optical diffusion film, the attachment process can be omitted, and higher luminance can be achieved. Can be indicated.

As the light diffusion particles, particles having a resin matrix and a high refractive index may be used, for example, TiO ₂ , silica, borosilicate, alumina, sapphire, hollow beads or particles filled with air or other gas (e.g., 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-diffusion particles may be in the range of 0.1 μm to 5 μm, for example, in the range of 0.3 μm to 1 μm. The content of the light-diffusion particles may be determined as needed.

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

The color conversion film according to the above-described embodiment may include a substrate on one surface. This substrate may function as a support when manufacturing the color conversion film. The type of the substrate is not particularly limited, and it 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.

According to an exemplary embodiment of the present specification, a backlight unit including the color conversion film is provided. The backlight unit may have a configuration of a backlight unit known in the art, except for including the color conversion film. 1 shows a schematic diagram of a structure of a backlight unit according to an example. Referring to FIG. 1, a color conversion film including a compound represented by Chemical Formula 1 is provided on a surface opposite to a surface of a light guide plate that faces a reflective plate. 1 illustrates a configuration including a light source and a reflector surrounding the light source, but is not limited to such a structure, and may be modified according to a structure of a backlight unit known in the art. In addition, as the light source, not only the side chain type but also the direct type may be used, and the reflector or reflective layer may be omitted or replaced with other configurations as necessary, and additional films such as light diffusing film, condensing film, brightness enhancing film as necessary The etc. may be further provided. Preferably, on the color conversion film, a prism sheet, a multilayer reflective polarizer film, a condensing film or a luminance enhancing film is further provided.

In the configuration of the backlight unit as illustrated in FIG. 1, a scattering pattern may be provided on an upper surface or a lower surface of the light guide plate as necessary. The 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 the scattering pattern can be used to induce the non-uniform light distribution to uniform brightness. .

According to an exemplary embodiment of the present specification, a display device including the backlight unit is provided. A display device including a backlight unit is not particularly limited. For example, the display device includes a display module and a backlight unit. 2 illustrates the structure of a display device. However, the present invention is not limited thereto, and additional films, such as a light diffusion film, a condensing film, and a luminance enhancing film, may be further provided between the display module and the backlight unit if necessary.

Hereinafter, the present specification will be described in more detail through examples. However, the following examples are for illustrative purposes only and are not intended to limit the present specification.

[Example]

[Production Example 1] Synthesis of Compound A

In a reaction vessel, 1 equivalent of monomer A-1 and 6 equivalents of triethylamine (TEA) were dissolved in a solvent of dichloromethane (DCM) and stirred in an ice bath. 6 equivalents of methacryloyl chloride dissolved in dichloromethane was slowly added to this reaction vessel, and then DMAP (4-dimethylaminopyridine) was added, followed by stirring at room temperature under nitrogen. After the reaction was completed, extraction was performed using dichloromethane and water, and the separated organic layer was removed by using anhydrous magnesium sulfate (MgSO ₄ ). The organic layer from which water was removed was concentrated through distillation under reduced pressure, and then recrystallized from methyl tertiary butyl ether (TBME) and hexane to obtain Compound A by suction filtration. Compound A was dried under reduced pressure conditions at 80°C.

HR LC/MS/MS m/z calcd for C82H72N4O18 (M+): 1400.4842; found: 1400.4842

[Production Example 2] Synthesis of Compound B

In the synthesis of compound A, synthesis was carried out in the same manner as in Preparation Example 1, except that monomer B-1 was used instead of monomer A-1, and compound B was synthesized through this.

HR LC/MS/MS m/z calcd for C92H88N8O16 (M+): 1560.6318; found: 1560.6320

[Production Example 3] Synthesis of Compound C

In the synthesis of compound A, the synthesis was carried out in the same manner as in Preparation Example 1, except that monomer C-1 and epichlorohydrin were used instead of monomer A-1 and methacryloyl chloride, through which compound C was synthesized. I did.

HR LC/MS/MS m/z calcd for C86H60N4O18 (M+): 1436.3903; found: 1436.3905

[Production Example 4] Synthesis of Compound D

After dissolving 1 equivalent of monomer D-1 and a catalytic amount of dimethylformamide (DMF) in a dichloromethane (DCM) solvent in the reaction vessel, 8 equivalents of oxalyl chloride are slowly added under an ice bath. After stirring at room temperature under nitrogen, dichloromethane was evaporated using a rotary evaporator. Acyl chloride was synthesized by replacing the hydroxy group with a chlorine group in the carboxyl group of the monomer D-1.

In another reaction vessel, 8 equivalents of 2-(trimethoxysilyl)ethanol and 20 equivalents of triethylamine (TEA) are dissolved in a dichloromethane solvent, and then the acyl chloride synthesized under an ice bath is dissolved in dichloromethane and slowly added. . The mixture is stirred under nitrogen at room temperature. After the reaction was completed, extraction was performed using dichloromethane and water, and the separated organic layer was removed by using anhydrous magnesium sulfate (MgSO ₄ ). The organic layer from which water was removed was concentrated through distillation under reduced pressure, and then recrystallized from dichloromethane and hexane to obtain Compound D by suction filtration. Compound D was dried under reduced pressure at 80°C.

HR LC/MS/MS m/z calcd for C88H94N6O26Si4 (M+): 1762.5295; found: 1762.5298

[Production Example 5] Synthesis of Compound E

In the synthesis of compound D, Preparation Example 4, except that monomers E-1 and oxiran-2-ylmethanamine were used instead of monomers D-1 and 2-(trimethoxysilyl) ethanol Synthesis was proceeded in the same manner as, through which compound E was synthesized.

HR LC/MS/MS m/z calcd for C96H72N8O18 (M+): 1624.4965; found: 1624.4965

[Production Example 6] Synthesis of Compound F

In the synthesis of compound A, the synthesis was carried out in the same manner as in Preparation Example 1, except that the monomer F-1 was used instead of the monomer A-1, and compound F was synthesized through this.

HR LC/MS/MS m/z calcd for C84H80N8O14 (M+): 1424.5794; found: 1424.5791

[Production Example 7] Synthesis of Compound G

In the synthesis of compound A, the synthesis was carried out in the same manner as in Preparation Example 1, except that monomer G-1 and 12 equivalents of epichlorohydrin were used instead of monomer A-1 and methacryloyl chloride. G was synthesized.

HR LC/MS/MS m/z calcd for C112H116N8O20 (M+): 1892.8306; found: 1892.8308

[Production Example 8] Synthesis of Compound H

In the synthesis of compound A, the synthesis was carried out in the same manner as in Preparation Example 1, except that monomer H-1 and acrylyl chloride were used instead of monomer A-1 and methacryloyl chloride, through which compound H was synthesized. .

HR LC/MS/MS m/z calcd for C95H82N4O21 (M+): 1614.5472; found: 1614.5472

[Preparation Example 9] Synthesis of Compound I

In the synthesis of compound A, the synthesis was carried out in the same manner as in Preparation Example 1, except that monomer I-1 was used instead of monomer A-1, and compound I was synthesized through this.

HR LC/MS/MS m/z calcd for C88H82N6O18 (M+): 1510.5686; found: 1510.5688

[Production Example 10] Synthesis of Compound J

In the synthesis of compound A, the synthesis was performed in the same manner as in Preparation Example 1, except that monomer J-1 was used instead of monomer A-1, and compound J was synthesized through this.

HR LC/MS/MS m/z calcd for C82H70N2O20 (M+): 1402.4522; found: 1402.4522

[Production Example 11] Synthesis of Compound K

In the synthesis of compound A, synthesis was carried out in the same manner as in Preparation Example 1, except that monomer K-1 was used instead of monomer A-1, and compound K was synthesized through this.

HR LC/MS/MS m/z calcd for C98H78N6O16 (M+): 1594.5474; found: 1594.5477

[Production Example 12] Synthesis of Compound L

In the synthesis of compound A, the synthesis was carried out in the same manner as in Preparation Example 1, except that monomer L-1 and epichlorohydrin were used instead of monomer A-1 and methacryloyl chloride, through which compound L was synthesized. I did.

HR LC/MS/MS m/z calcd for C68H50N2O2 (M+): 1214.2957; found: 1214.2957

[Production Example 13] Synthesis of Compound M

In the synthesis of compound A, the synthesis was carried out in the same manner as in Preparation Example 1, except that monomer M-1 and 2-chloro acryloyl chloride were used instead of monomer A-1 and methacryloyl chloride, through which the compound M was synthesized.

HR LC/MS/MS m/z calcd for C80H62Cl4N2O20 (M+): 1510.2650; found: 1510.2654

[Production Example 14] Synthesis of Compound N

In a reaction vessel, 1 equivalent of monomer N-1 and 12 equivalents of triethylamine were dissolved in a solvent of dichloromethane, followed by stirring in an ice bath. 12 equivalents of 2-chloro acryloyl chloride dissolved in dichloromethane was slowly added to this reaction vessel, and then DMAP (4-dimethylaminopyridine) was added, followed by stirring at room temperature under nitrogen. After stirring at room temperature for 2 hours, reflux reaction was performed. After the reaction was completed, extraction was performed using dichloromethane and water, and the separated organic layer was removed by using anhydrous magnesium sulfate (MgSO ₄ ). The organic layer from which water was removed was concentrated through distillation under reduced pressure, and then recrystallized from dichloromethane and hexane to obtain Compound N by suction filtration. Compound N was dried under reduced pressure conditions at 80°C.

HR LC/MS/MS m/z calcd for C90H74Cl6N4O22 (M+): 1772.2926; found: 1772.2927

[Production Example 15] Synthesis of Compound O

In the synthesis of compound A, the synthesis was carried out in the same manner as in Preparation Example 1, except that monomer O-1 and epichlorohydrin were used instead of monomer A-1 and methacryloyl chloride, through which compound O was synthesized. I did.

HR LC/MS/MS m/z calcd for C80H72N4O18 (M+): 1376.4842; found: 1376.4842

[Production Example 16] Synthesis of Compound P

In the synthesis of compound N, in the same manner as in Preparation Example 14, except that monomer P-1 and 4 equivalents of 2-chloro acryloyl chloride were used instead of monomer N-1 and 12 equivalents of 2-chloro acryloyl chloride. Synthesis was proceeded, through which compound P was synthesized.

HR LC/MS/MS m/z calcd for C76H66Cl2N4O12 (M+): 1296.4054; found: 1296.4052

[Production Example 17] Synthesis of Compound Q

In the synthesis of compound N, the synthesis was carried out in the same manner as in Preparation Example 14, except that monomer Q-1 and 4 equivalents of epichlorohydrin were used instead of monomers N-1 and 12 equivalents of 2-chloro acryloyl chloride. And, through this, compound Q was synthesized.

HR LC/MS/MS m/z calcd for C68H56N4O16 (M+): 1184.3691; found: 1184.3691

[Production Example 18] Synthesis of Compound R

In the synthesis of compound A, the synthesis was performed in the same manner as in Preparation Example 1, except that the monomer R-1 was used instead of the monomer A-1, through which compound R was synthesized.

HR LC/MS/MS m/z calcd for C80H62N2O20 (M+): 1370.3896; found: 1370.3898

[Production Example 19] Synthesis of Compound S

In the synthesis of compound N, the synthesis was carried out in the same manner as in Preparation Example 14, except that monomer S-1 and methacryloyl chloride were used instead of the monomer N-1 and 2-chloro acryloyl chloride, through which the compound S was synthesized.

HR LC/MS/MS m/z calcd for C90H80N4O20 (M+): 1536.5366; found: 1536.5366

[Comparative Preparation Example 1] Synthesis of Compound T

In a reaction vessel, 1 equivalent of monomer T-1, 8 equivalents of phenol, and 6 equivalents of potassium carbonate were dissolved in a methylpyrrolidone (NMP) solvent, followed by stirring at 110°C. After the reaction was completed, a compound was obtained using water and obtained by suction filtration. After the obtained compound was extracted using dichloromethane and water, the separated organic layer was removed from water using anhydrous magnesium sulfate. The organic layer from which water was removed was concentrated through distillation under reduced pressure, and then recrystallized using dichloromethane and ethanol to obtain Compound T by suction filtration. Compound T was dried under reduced pressure conditions at 80°C.

HR LC/MS/MS m/z calcd for C72H58N2O8 (M+): 1078.4193; found: 1078.4195

[Comparative Preparation Example 2] Synthesis of Compound U

In the reaction vessel, 1 equivalent of monomer U-1 and 10 equivalents of ammonium acetate were dissolved in a propionic acid solvent, followed by refluxing for 24 hours. After the reaction is completed, the precipitate is collected using water. The precipitate was obtained by suction filtration and used in the next reaction without further purification. After dissolving 1 equivalent of the precipitate with a dimethylformamide (DMF) solvent, 1 equivalent of sodium methoxide was added and stirred for 4 hours. Then, 6 equivalents of 3-bromo-1-propine was added and stirred for 24 hours. After the reaction was completed, extraction was performed using water, and water was removed from the separated organic layer using anhydrous magnesium sulfate. The organic layer from which water was removed was concentrated through distillation under reduced pressure, and then recrystallized using dichloromethane and ethanol to obtain Compound U by suction filtration. Compound U was dried under reduced pressure at 80°C.

HR LC/MS/MS m/z calcd for C58H38N2O8 (M+): 890.2628; found: 890.2628

[Comparative Preparation Example 3] Synthesis of Compound V

For the synthesis of compound T, T-1 monomer and phenol instead, except that the monomers V-1 and 4-propargyl oxy-phenol (p -propargyloxyphenol), comparison was conducted for synthesis by the same method as in Production Example 1, through which Compound V was synthesized.

HR LC/MS/MS m/z calcd for C66H38N2O12 (M+): 1050.2425; found: 1050.2426

[Example 1]

1.5 parts by weight of the compound prepared in Preparation Example 1 (maximum absorption wavelength in toluene solution 579 nm, maximum emission wavelength 610 nm) 33.9 parts by weight of an acrylic binder (VS12A80, LG Chem), a polyfunctional monomer (pentaerythritol triacrylate) , Japanese explosives) 59.3 parts by weight, adhesion aid and surfactant (KBM 503, shinetsu) 2.3 parts by weight, photoinitiator (Tinuvin® 477, BASF) 3.0 parts by weight solvent PGMEA (propylene glycol monomethyl ether) so that the solid content is 21% by weight Acetate: Propylene glycol monomethyl ether acetate) to prepare a solution. After sufficiently stirring the mixed solution, a thin film was coated on a glass substrate and dried to prepare a color conversion film.

Here, a to g are each independently the number of repeating units in parentheses.

[Example 2]

Example 1 was carried out in the same manner as in Example 1, except that Compound C (maximum absorption wavelength in toluene solution 575 nm, maximum emission wavelength 609 nm) was used instead of Compound A in Example 1.

[Example 3]

Example 1 was carried out in the same manner as in Example 1, except that Compound E (maximum absorption wavelength 577 nm in toluene solution, maximum emission wavelength 611 nm) was used instead of Compound A in Example 1.

[Example 4]

Example 1 was carried out in the same manner as in Example 1, except that compound F (maximum absorption wavelength in toluene solution 573 nm, maximum emission wavelength 607 nm) was used instead of compound A.

[Example 5]

Example 1 was carried out in the same manner as in Example 1, except that Compound J (maximum absorption wavelength 578 nm in toluene solution, maximum emission wavelength 609 nm) was used instead of Compound A in Example 1.

[Example 6]

Example 1 was carried out in the same manner as in Example 1, except that Compound L (maximum absorption wavelength in toluene solution 579 nm, maximum emission wavelength 609 nm) was used instead of Compound A in Example 1.

[Example 7]

Example 1 was carried out in the same manner as in Example 1, except that Compound N (maximum absorption wavelength in toluene solution 582 nm, maximum emission wavelength 612 nm) was used instead of Compound A in Example 1.

[Example 8]

Example 1 was carried out in the same manner as in Example 1, except that compound Q (maximum absorption wavelength 581 nm in toluene solution, maximum emission wavelength 610 nm) was used instead of compound A in Example 1.

[Example 9]

In Example 1, it was carried out in the same manner as in Example 1, except that Compound S (maximum absorption wavelength 584 nm in toluene solution, maximum emission wavelength 613 nm) was used instead of Compound A.

[Comparative Example 1]

Example 1 was carried out in the same manner as in Example 1, except that Compound T (maximum absorption wavelength 572 nm in toluene solution, maximum emission wavelength 601 nm) was used instead of Compound A in Example 1.

[Comparative Example 2]

Example 1 was carried out in the same manner as in Example 1, except that compound U (maximum absorption wavelength 570 nm in toluene solution, maximum emission wavelength 599 nm) was used instead of compound A in Example 1.

[Comparative Example 3]

Example 1 was carried out in the same manner as in Example 1, except that Compound V (maximum absorption wavelength in toluene solution 573 nm, maximum emission wavelength 600 nm) was used instead of Compound A in Example 1.

[Experimental Example 1]

1) Measurement of absorption and emission spectrum of film state

The luminance spectra of the color conversion films prepared in Examples 1 to 9 and Comparative Examples 1 to 3 were measured with a spectroradiometer (TOPCON SR series). Specifically, the prepared color conversion film was laminated on one side of a light guide plate of a backlight unit including an LED blue backlight (maximum emission wavelength 450 nm) and a light guide plate, and a prism sheet and a double brightness enhancement (DBEF) film on the color conversion film After laminating, the initial value was set so that the brightness of the blue LED light was 600 nit based on the film.

2) Measurement of absorption and emission spectrum in solution state

In order to measure the absorption and emission wavelength, the sample was dissolved in a concentration of 10 ^-5 M using toluene as a solvent, and then their absorption and emission spectra were measured.

3) Check the degree of migration

Based on 100wt% of the photosensitive fluorescent resin composition, 0.63wt% (3.0wt% in solid content) of the dye to be measured (compound in Table 1), 7.37wt% of binder (VS12A80, LG Chem) and 13wt% of polyfunctional monomer (Dipentaerythritol hexaacrylate) was dissolved in 79 wt% PGMEA (Propylene glycol monomethyl ether acetate) to prepare a photosensitive fluorescent resin composition.

The prepared photosensitive fluorescent resin composition was spin-coated on a 5 cm×5 cm glass (Corning), and pre-bake at 110° C. for 70 seconds to form a coating film. Then, the distance between the coating film and the photo mask was set to 200 μm, and an exposure amount of 40 mJ/cm ² was irradiated using an exposure machine (Hoya-shott). The exposed coating film was developed in a developer (KOH, 0.04%) for 60 seconds to form a pattern layer having a pattern width and a space width of 90 μm and 180 μm, respectively.

After forming the pattern layer, the first post-bake (PB) was performed in an oven at 30° C. for 20 minutes. Thereafter, a solution in which 33wt% of a photocurable epoxy acrylic resin was dissolved in a mixture of PGMEA, MMP (Methyl-3-methoxy propionate) and MEDG (Methyl Ethyl Di Glycol) as solvents was overcoated with a negative type coating method, The color conversion film was completed by performing a second post-bake (PB) treatment in an oven at 30° C. for 30 minutes. The colorimeter value of the pattern part of the pattern layer without the overcoat layer and the colorimeter value of the pattern part after the overcoat layer was formed were measured, and the degree of migration was confirmed through the difference between the two measured values (ΔEab).

Table 1 shows the physical properties of the compounds used in Examples 1 to 9 and Comparative Examples 1 to 3 in the solution, the absorption and emission wavelengths of the thin film when applied to the color conversion film, and ΔEab values.

From Table 1 above, the compound according to the present invention has a longer wavelength of absorption and emission in a solution and a thin film than in the comparative example, and it is confirmed that the ΔEab value is 3 or less, so that it is found that migration is less than that of the comparative example. I can.

Claims (13)

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

In Formula 1,
X1 and X2 are the same as or different from each other, and each independently O; Or NR1,
A1 and A5 are the same as or different from each other, and each independently -CR2R3-; -C(=O)-; Or a substituted or unsubstituted hydrocarbon ring,
A2 and A6 are the same as or different from each other, and each independently -CR2R3-; -S-; -O-; -NR4-; Or a substituted or unsubstituted hydrocarbon ring,
A3 and A7 are the same as or different from each other, and each independently -CR2R3-; Or a substituted or unsubstituted hydrocarbon ring,
A4 and A8 are the same as or different from each other, and each independently -CR2R3-; -S-; -O-; -NR4-; -N=; =N-; =CR5-; -CR6=; -C(=O)-; Or a substituted or unsubstituted hydrocarbon ring,
R2 and R3 are the same as or different from each other, and each independently hydrogen; Halogen group; Cyano group; Hydroxy group; Nitro group; Mercapto group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or R2 and R3 are bonded to each other to form a substituted or unsubstituted ring,
R5 and R6 are the same as or different from each other, and each independently hydrogen; Halogen group; Cyano group; Hydroxy group; Nitro group; Mercapto group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
n1 to n4 are each independently 0 or 1,
R1, R4, and M1 to M20 are the same as or different from each other, and each independently hydrogen; Halogen group; Cyano group; Hydroxy group; Nitro group; Mercapto group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; Or a substituent represented by the following formula (2),
At least one selected from the group consisting of R1, R4 and M1 to M20 is each independently a substituent represented by the following formula (2),
[Formula 2]

In Chemical Formula 2,
X3 is a direct bond; O; C(=O)NH; Or NH,
L is a substituted or unsubstituted alkylene group; A substituted or unsubstituted cycloalkylene group; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,
a is an integer from 0 to 2,
l is 1 or 2,
E is a polymerizable group,
* Indicates the bonding position,
When a and l are each 2, the structures in parentheses are the same or different from each other. The method according to claim 1, wherein the polymerizable group is a substituted or unsubstituted ethylenically unsaturated group; A substituted or unsubstituted siloxane group; And a group having at least one selected from the group consisting of a substituted or unsubstituted epoxy group. The compound of claim 1, wherein the polymerizable group has any one of the following structures:

In the above structure,
Z1 and Z2 are each independently hydrogen, a halogen group, or a substituted or unsubstituted alkyl group,
Z3 to Z5 are each independently a substituted or unsubstituted alkyl group,
* Indicates the bonding position. The compound of claim 1, wherein Formula 1 is represented by the following Formula 3:
[Formula 3]

In Chemical Formula 3, X1, X2, A1 to A8, n1 to n4, and M1 to M5 are as defined in Chemical Formula 1. The method of claim 1, wherein any one of M1 to M5, any one of M6 to M10, any one of M11 to M15, any one of M16 to M20, and at least one selected from the group consisting of R1 are each independently represented by Formula 2 A compound that is a represented substituent. The compound of claim 1, wherein Formula 1 is represented by any one of the following Formulas 4 to 6:
[Formula 4]

[Formula 5]

[Formula 6]

In Formulas 4 to 6, X1 to X2, A1 to A8, and n1 to n4 are as defined in Formula 1, and X3, L, E, l and a are as defined in Formula 2,
M1 to M5 are the same as or different from each other, and each independently hydrogen; Halogen group; Cyano group; Hydroxy group; Nitro group; Mercapto group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group. The method according to claim 1, in the formula 1

And

Are each independently any one of the following structures:

In the above structure,
B1 to B144 are the same as or different from each other, and each independently hydrogen; Halogen group; Hydroxy group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
C1 to C57 are the same as or different from each other, and each independently, a substituent represented by Formula 2; Hydrogen; Halogen group; Hydroxy group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
* Indicates the bonding position. The method according to claim 7, B1 to B144 are the same as or different from each other, and each independently hydrogen; Halogen group; Hydroxy group; A substituted or unsubstituted alkoxy group; An alkyl group unsubstituted or substituted with a substituent selected from the group consisting of an aryl group and a heteroaryl group; Haloalkyl group; Cycloalkyl group; A substituted or unsubstituted aryl group; Furanyl group; Pyridyl group; Pyrimidyl group; Or a triazinyl group,
C1 to C57 are the same as or different from each other, and each independently, a substituent represented by Formula 2; Hydrogen; An alkyl group unsubstituted or substituted with a substituent selected from the group consisting of an aryl group and a heteroaryl group; Haloalkyl group; Aryl group; A substituted or unsubstituted cycloalkyl group; Furanyl group; Pyridyl group; Pyrimidyl group; Or a compound that is a triazinyl group. The compound of claim 1, wherein the compound represented by Formula 1 is represented by any one of the following compounds:

In the above compound, Ph is a phenyl group. Binder resin; Polyfunctional monomers; And A photosensitive fluorescent resin composition comprising the compound according to any one of claims 1 to 9. A color conversion film comprising the compound according to any one of claims 1 to 9 combined with a binder resin. A backlight unit comprising the color conversion film according to claim 11. A display device including the backlight unit according to claim 12.

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