CN118272073A

CN118272073A - Luminescent organic nanoparticle, composition for color conversion film comprising same, color conversion film prepared from same, display device, and light-emitting diode device

Info

Publication number: CN118272073A
Application number: CN202311296091.3A
Authority: CN
Inventors: 权章赫; 奇京珉; 金省呼; 徐康一; 蔡美荣; 郑映勋
Original assignee: Ke Laipeng Co ltd; Endi Materials Co ltd
Current assignee: Ke Laipeng Co ltd; Endi Materials Co ltd
Priority date: 2022-12-30
Filing date: 2023-10-08
Publication date: 2024-07-02
Also published as: KR20240108856A

Abstract

Provided are luminescent organic nanoparticles, a composition for a color conversion film comprising the same, and a color conversion film, a display device, and a light-emitting diode device produced by the same, wherein the luminescent organic nanoparticles comprise an organic phosphor having a luminous efficiency of 80% or more, have an average particle diameter of 100-170 nm, and have a standard deviation of 500nm or less.

Description

Luminescent organic nanoparticle, composition for color conversion film comprising same, color conversion film prepared from same, display device, and light-emitting diode device

Technical Field

The present invention relates to luminescent organic nanoparticles, a composition for a color conversion film comprising the same, and a method for producing the same

The color conversion film, the display device and the light emitting diode device thus prepared.

Background

In order to prepare white light using a light emitting diode as a light source, the following method is mainly used: blue to be blue

Color light emitting diodes are used as light sources using color conversion formed of phosphors, organic dyes, quantum dots, etc

The film-changing converts the light source emitted from the blue light emitting diode into white light. Material of color conversion film at this time

In order to have a high color rendering index, full WIDTH AT HALF Maximum, FWHM

Wide and has good heat resistance to bear the heat of the light emitting diode. In contrast, the light source emits light twice

Different from the polar tube, the material of the color conversion film used in the display should have good color purity, because

This mainly uses fluorescence, phosphorescence, quantum dots, etc. showing small full width half maximum emission characteristics.

Blue Light Emitting Diode (LED) and yellow phosphor, which are most widely used among light emitting diodes, are used

The method of (2) has a low color rendering index and a yellow phosphor emits little red light, and thus has a high correlation color

A warm disadvantage. In the case where an organic dye is used for the color conversion layer, the property of aggregation upon light emission is exhibited,

Therefore, there is a problem that a extinction phenomenon occurs and photochemical stability is low.

Quantum Dot (QD) using inorganic substances has photoluminescence Quantum yield (P)

Hotoluminescence Quantum Yield PLQY) is good, the reaction time is fast, and the reliability is high

But is weak to moisture and has heat resistance lower than 100 ℃, so that it is not good and is difficult to be used as a light emitting diode

And the use of heavy metals such as cadmium, arsenic, lead. In particular, lead, cadmium,

The high in vivo accumulation of heavy metals such as mercury, chromium, arsenic, etc. is a great public health problem. Body

The absorbed heavy metals are accumulated in hair and organs and tissues in the body by blood, and heavy metals are absorbed in the body

The residence time is short in blood or urine but in the case of hair, it lasts longer. In general, the number of the devices used in the system,

In vivo accumulation of heavy metals is formed by chain food chains, and predators show a body compared to the predators

Higher inner concentration is the bioconcentration property. In particular, cadmium used as a fluorescent substance causes serious damage to the stomach, lung, and bones.

In order to apply the organic material or the organic nanoparticle to a display device or the like, it cannot be used alone, and it should be prepared and used in a thin film form. The film prepared directly using the organic substance has poor photostability as compared to the film prepared using the organic nanoparticle. In order to prepare organic nanoparticles into a thin film, it is necessary to satisfy the conditions that the organic nanoparticles are inconvenient to maintain in terms of their properties, have good dispersibility in resins, do not deteriorate in terms of their properties even when exposed to incident light for a long period of time, and have good room temperature stability.

Prior art literature

Patent literature

Patent document 1: korean patent No. 10-2081481

Patent document 2: korean laid-open patent No. 10-2020-0034949

Disclosure of Invention

Technical problem

One of the objects of the present invention is to provide organic nanoparticles obtained from a light-emitting organic substance, a composition for a color conversion film comprising the same, a color conversion film, a display device, and a light-emitting diode device each of which is excellent in color conversion efficiency, has thermal stability, and does not use heavy metals.

Technical proposal

According to one aspect of the present invention, there is provided a luminescent organic nanoparticle comprising an organic fluorescent material having a luminous efficiency of 80% or more, an average particle diameter of 100nm to 170nm, and a standard deviation of the particle diameter of 500nm or less.

In one embodiment, the organic fluorescent material may have a core-shell structure in which the organic fluorescent material is surrounded by a surfactant.

In one embodiment, the organic phosphor may be a Delayed fluorescent material (Delayed fluorescent ESCENCE MATERIAL).

In one embodiment, the delayed fluorescent material may be a compound represented by chemical formula 1 below.

Chemical formula 1:

(in the above chemical formula 1,

L is one selected from the group consisting of aryl, arylene, and carbon-nitrogen single bond,

When L is an aryl group, A is a cyano group substituted with the above aryl group 1 or 2, D is a substituent substituted with the above aryl group 4 or 5, each of the above substituents is independently a heteroaryl group having a nitrogen atom substituted or unsubstituted with a hydrocarbon group having 1 to 10 carbon atoms,

When L is an arylene group, A is a substituted or unsubstituted triazinyl group, D is a substituted or unsubstituted multiple parallel ring comprising conjugated or unconjugated five-or six-sided rings containing a nitrogen atom bonded to the arylene group, wherein the multiple parallel ring is a ring-forming element which may contain 1 to 9 nitrogen atoms or 1 group 16 element in addition to the nitrogen atom bonded to the arylene group,

When L is a carbon-nitrogen single bond, D is a carbon-nitrogen single bond, a conjugated or unconjugated five-or six-sided ring containing a nitrogen atom of the above L, a ring in which the conjugated or unconjugated five-or six-sided ring is substituted or unsubstituted, a ring in which a group 16 element is a ring-forming element, 1 or 2 nitrogen atoms are a ring-forming element, a is a heterocyclic ring having a carbon number of 10 to 40, an aryl group containing a carbon atom bonded to the above L, wherein the above heterocyclic ring contains a ring structure forming a ring with an aryl group containing a carbon atom bonded to the above L, wherein the above ring structure is a ring structure containing a boron atom and an oxygen atom as ring-forming elements, or a five-or six-sided ring structure containing 2 nitrogen atoms conjugated. )

In an embodiment, the compound represented by the above chemical formula 1 may be one or more selected from the group consisting of the following compounds T-1 to T-28.

In one embodiment, the organic phosphor may be a boron compound represented by the following chemical formula 2.

Chemical formula 2:

(in the above chemical formula 2,

R ₁ to R ₅ are each independently at least one member selected from the group consisting of hydrogen, deuterium, halogen, hydroxy, cyano, nitro, substituted or unsubstituted amino, amidino, hydrazino, hydrazono, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted alkoxy, substituted or unsubstituted cycloalkyl, substituted or unsubstituted cycloalkenyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted heterocycloalkenyl, substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, substituted or unsubstituted heteroaryl and substituted or unsubstituted heteroaryloxy,

X ₁ to X ₄ are each independently hydrogen, hydroxy, or substituted or unsubstituted alkyl,

N1 and n4 are each independently integers from 1 to 4,

N2, n3 and n5 are each independently integers from 1 to 3,

In the case where n1 to n5 are 2 or more, the structures in brackets may be the same or different from each other,

R ₁ to R ₅ and X ₁ to X ₄ may form a substituted or unsubstituted ring by bonding with adjacent substituents. )

In an embodiment, the boron compound represented by the above chemical formula 2 may be one or more selected from the group consisting of the following compounds D-1 to D-30.

In one embodiment, the organic phosphor may be a boron compound represented by the following chemical formula 3.

Chemical formula 3:

(in the above-mentioned chemical formula 3,

C ₁ to C ₃ have a five-sided or six-sided ring structure respectively,

R ₅₁ and R ₅₂ are each independently one selected from the group consisting of hydrogen, deuterium, halogen, hydroxy, cyano, nitro, substituted or unsubstituted amino, amidino, hydrazino, hydrazono, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted alkoxy, substituted or unsubstituted thioether, substituted or unsubstituted cycloalkyl, substituted or unsubstituted cycloalkenyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted heterocycloalkenyl, substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, substituted or unsubstituted heteroaryl and substituted or unsubstituted heteroaryloxy, which may form a substituted or unsubstituted ring by bonding with an adjacent substituent,

R ₅₃ corresponds to one selected from the group consisting of hydrogen, deuterium, halo, hydroxy, cyano, nitro, amino, amidino, hydrazino, hydrazono, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted alkoxy, substituted or unsubstituted cycloalkyl, substituted or unsubstituted cycloalkenyl, substituted or unsubstituted thioether, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted heterocycloalkenyl, substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, substituted or unsubstituted heteroaryl, and substituted or unsubstituted heteroaryloxy,

Y ₁ and Y ₂ are each independently fluorine or alkoxy,

A and b are each independently integers from 1 to 4,

In the case where a and b are 2 or more, the structures in brackets may be the same or different from each other,

R ₅₁ to R ₅₂ may form a substituted or unsubstituted ring by bonding with an adjacent substituent. )

In one embodiment, the boron compound represented by the above chemical formula 3 may be one or more light-emitting organic nanoparticles selected from the group consisting of the following compounds B-1 to B-33.

In one embodiment, the surfactant may be at least one selected from the group consisting of anionic surfactants, cationic surfactants, zwitterionic surfactants and nonionic surfactants.

According to still another aspect of the present invention, there is provided a composition for a color conversion film, which comprises the above-described luminescent organic nanoparticle and a water-soluble polymer resin.

In one embodiment, the composition for a color conversion film may include 1 to 20 parts by weight of the luminescent organic nanoparticle based on 100 parts by weight of the water-soluble polymer resin.

In one embodiment, the composition for a color conversion film may contain 0.01 to 20 parts by weight of a crosslinking agent based on 100 parts by weight of the water-soluble polymer resin.

In one embodiment, the composition for a color conversion film may contain 1 to 20 parts by weight of a light scattering agent based on 100 parts by weight of the water-soluble polymer resin.

In one embodiment, the water-soluble polymer resin has a weight average molecular weight of 5000g/mol to 100000g/mol and a hydration degree of 70% to 100% and is one or more polymers or copolymers selected from the group consisting of nonionic water-soluble polymers, anionic water-soluble polymers and cationic water-soluble polymers.

In an embodiment, the nonionic water-soluble polymer may be one or more polymers or copolymers selected from the group consisting of polyvinyl alcohol (Polyvinyl alcohol, PVA), polyethylene oxide (Polyethylene oxide, PEO), polyacrylamide (Polyacrylamide, PAM) and polyvinylpyrrolidone (Polyvinylpyrrolidone, PVP).

In one embodiment, the anionic water-soluble polymer may be one or more selected from the group consisting of Polyacrylic acid (PAA) and derivatives thereof, polystyrene sulfonic acid (Poly (styrene sulfonic acid), PSSA), polysilicic acid (Poly (sil icic acid), PSiA), polyphosphoric acid (Poly (phosphoric acid), PPA), polyethylene sulfinic acid (Poly (ethylenesulfinic acid), PESA), poly [3- (ethyleneoxy) propane-1-sulfonic acid ] (Poly [3- (vinyloxy) propane-1-sulfonic acid ]), poly (4-vinyl phenol) (Poly (4-vinylphenol)), poly (4-vinyl phenol sulfuric acid) (Poly (4-vinylphenol sulfuric acid)), poly (ethylene phosphoric acid) (Poly (ethylenephosphoric acid)), poly (maleic acid) (Poly (maleic acid)), poly (2-methyl ethylene oxide-1-sulfonic acid) (Poly (2-methacryloxyethane-1-sulfonic acid)), poly (3-methacryloxypropane-1-sulfonic acid) (Poly (3-methacryloyloxypropane-1-sulfonic acid)), and Poly (4-vinyl benzoic acid) (Poly (4-vinylbenzoic acid)).

In one embodiment, the cationic water-soluble polymer may be one or more polymers or copolymers selected from the group consisting of polyethyleneimine (Polyethyleneimine, PEI), polyamine (Polyamines), polyamidoamine (Polyamideamine, PAMAM), polydienedimethylammonium chloride (Poly (diallyldimethyl ammoniumchloride), PDADMAC), poly (4-vinylbenzyltrimethylammonium salt) (Poly (4-vinylbenzyltrimethylammonium salt)), poly [ (dimethylimino) trimethylene (dimethylimino) hexamethylenedibromo ] (Poly [ (dimethylimino) TRIMETHYLENE (DIMETHYLIMINO) hexamethylenedibromide ], polybrene), poly (2-vinylpiperidine salt) (Poly (2-VINYLPI PERIDINE SALT)), poly (vinylamine salt) (Poly (vinylamine salt)), and Poly (2-vinylpyridine) (Poly (2-VINYLPYRIDINE)) and derivatives thereof.

In an embodiment, the crosslinking agent may be one or more selected from the group consisting of glutaraldehyde (gluteraldehydes), glyoxal (glyoxal), maleic acid (MALEIC ACID), citric acid (CITRIC ACID), sodium trimetaphosphate (trisodium trimetaphosphate), sodium hexametaphosphate (sodium hexa metaphosphate), dianhydride (DIANHYDRIDES), succinic acid (succinic acid), suberic acid (suberic acid), sulfosuccinic acid (sulfosuccinic acid), and K ₂S₂O₈.

In an embodiment, the light scattering agent may be one or more inorganic metal oxide particles selected from the group consisting of TiO ₂、ZnO、Fe₃O₄、CeO₂、MoO₂、Ag₂ O, cuO and NiO.

In one embodiment, the average particle size of the inorganic metal oxide particles may be 200nm to 400nm.

According to another aspect of the present invention, there is provided a color conversion film prepared using the above-described composition for a color conversion film.

According to still another aspect of the present invention, there is provided a display device or a light emitting diode device including the above color conversion film.

Effects of the invention

According to the present invention, the luminescent organic nanoparticle can provide a color conversion film having excellent optical stability, high color conversion efficiency, high heat resistance, excellent film hardness characteristics of the film, high uniformity, and long-term retention of performance. In particular, the color conversion film of the present invention uses luminescent organic nanoparticles that do not use quantum dots, and thus, can prevent environmental pollution problems.

The effects of the present invention are not limited to the above-described effects, and should be understood to include all effects that can be deduced from the description of the invention of the present specification or the features described in the claims.

Drawings

FIG. 1 shows ¹ H-NMR data for Ttrz-DI.

Part (a) of fig. 2 shows UV-Vi s, room temperature photoluminescence (Room temperature photoluminescence, RTPL) and low temperature photoluminescence (Low tempe rature photoluminescence, LTPL) spectra of Ttrz-DI in toluene, and part (b) of fig. 2 shows time resolved photoluminescence (Time resolved photoluminescence, TRPL) of Ttrz-DI in solvent.

Fig. 3a is a graph showing the size of particles and the emission wavelength according to the state of Ttrz-DI in the case of using Triton X-100 (Triton X-100) as a surfactant, and fig. 3b is a graph showing the size of particles and the emission wavelength according to the state of Ttrz-DI in the case of using TBAOleate as a surfactant.

FIG. 4a is a graph showing the results of measuring the transparency of the base film of preparation example 2-2 after the base film was left at room temperature (25 ℃) for 1 hour at 130 ℃, 180℃and 200℃respectively, and FIG. 4b is a graph showing the base film of preparation example 2-2 after the base film was left at 200℃for 1 hour.

Fig. 5a is a picture taken after pencil hardness was measured for preparation example 2-1, and fig. 5b is a picture taken after pencil hardness was measured for comparative preparation example 2-1.

Fig. 6 is a diagram showing optical characteristics and Color Conversion Efficiency (CCE) calculation methods of the color conversion film of preparation example 3-1.

FIG. 7 is a graph showing the evaluation results of light resistance after 120 hours of exposure to UV in preparation example 3-1 and comparative preparation example 3-2.

Fig. 8 is a graph showing the luminous intensity (Emission intensity) of the wavelengths of the color conversion films according to preparation examples 4-1 to 4, and fig. 9 is a graph showing the light intensity (Radiant power) of the wavelengths of the color conversion films according to preparation examples 4-1 to 4.

Fig. 10 is a graph showing absorbance of the color conversion films of preparation examples 4-4 to 4-6, fig. 11 is a graph showing light intensity of the thin films prepared by preparing the color conversion films of preparation examples 4-4 to 4-6 as a single layer, and fig. 12 is a graph showing light intensity of the thin films prepared by laminating 2 sheets of the color conversion films of preparation examples 4-4 to 4-6.

Fig. 13 is a graph of absorbance of the color conversion films of reference examples 1 to 3, fig. 14 is a graph of photoluminescence intensity (Photoluminescence Intensity) of the color conversion films of reference examples 1 to 3, fig. 15 is a graph of light intensity (RADIANT INTENSITY) of the color conversion films of reference examples 1 to 3, and fig. 16 is a graph of light intensity of the color conversion films of preparation examples 4 to 5.

Fig. 17 is a graph showing the results of constant temperature and humidity evaluation for the color conversion films of reference example 2, and fig. 18 is a graph showing the results of constant temperature and humidity evaluation for the color conversion films of preparation examples 4 to 5.

Fig. 19 is a graph showing the results of light fastness evaluation for the color conversion films of reference example 2, and fig. 20 is a graph showing the results of light fastness evaluation for the color conversion films of production examples 4 to 5.

Fig. 21 is a graph showing absorbance of the color conversion films of preparation examples 5-1 to 5-4, fig. 22 is a graph showing light intensity for the thin films prepared by laminating 2 sheets of the color conversion films of preparation examples 5-1 to 5 as a single layer, and fig. 23 is a graph showing light intensity for the thin films prepared by laminating 2 sheets of the color conversion films of preparation examples 5-4 and 5-5.

Detailed Description

Before explaining the present application in detail, it should be understood that terms or words used in the present specification and claims described below should not be interpreted as being limited to general or dictionary meanings, but interpreted based on the principle that the inventor describes his own application in an optimal manner and can appropriately define the concept of terms in conformity with the technical ideas of the present application. Therefore, the embodiments described in the present specification and the configurations shown in the drawings are only the most preferable embodiments of the present application, and do not represent the whole technical ideas of the present application, and therefore, in the aspect of the present application, there are various equivalent technical solutions and modifications that can replace these.

Throughout this specification, when a portion is referred to as "comprising" a structural element, unless expressly stated to the contrary, it is intended that the portion also comprises other structural elements, rather than excluding other structural elements. Also, unless specifically mentioned otherwise, singular forms also include plural forms.

When numerical ranges are recited in this specification, unless a specific range is stated otherwise, the values thereof have the precision of the significant figures provided according to standard rules in chemistry for the significant figures. For example, 10 includes a range of 5.0 to 14.9, and the number 10.0 includes a range of 9.50 to 10.49.

Luminescent organic nanoparticles

According to one aspect of the present invention, there is provided a luminescent organic nanoparticle comprising an organic phosphor having a luminous efficiency of 80% or more.

The average particle diameter of the luminescent organic nanoparticles is 100nm to 170nm, preferably 110nm to 160nm, more preferably 120nm to 150nm.

The standard deviation of the particle diameter of the luminescent organic nanoparticles may be 500nm or less, preferably 450nm or less, more preferably 400nm or less, still more preferably 350nm or less, still more preferably 300nm or less, and most preferably 280nm or less.

The color conversion film using the luminescent organic nanoparticles having the average particle diameter and standard deviation of the particle diameter in the ranges as described above has excellent advantages of color conversion efficiency, UV stability, normal temperature stability, and the like.

Organic fluorescent material

The organic phosphor may be one or more selected from the group consisting of green phosphor, blue phosphor and red phosphor, and various phosphors known in the art to which the present invention pertains may be used as long as the luminous efficiency is 80% or more.

In the case of using the light emitting type organic nanoparticle as a light emitting diode, it should have a wide full width at half maximum, and thus, it is preferable to use a delayed fluorescent material (Delayed Fluorescence Material).

The delayed fluorescent material is a material that can improve internal quantum efficiency, preferably a thermally activated delayed fluorescent material (THERMALLY ACTIVATED DELAYED Fluorescence, TADF), which is a material that uses heat to move 3 triplet exciton particles, which are particles disappeared by heat or vibration, at a single exciton level and fluoresce.

The delayed fluorescent material having such characteristics is not particularly limited, but may be exemplified by a compound represented by the following chemical formula 1.

Chemical formula 1:

(in the above chemical formula 1,

When L is an aryl group, A is a cyano group substituted in the above aryl group 1 or 2, D is a substituent substituted in the above aryl group 4 or 5, each of the above substituents is independently a heteroaryl group containing a nitrogen atom substituted or unsubstituted with a hydrocarbon group having 1 to 10 carbon atoms,

When L is an arylene group, A is a substituted or unsubstituted triazinyl group, D is a substituted or unsubstituted multiple parallel ring comprising conjugated or unconjugated five-or six-sided rings containing a nitrogen atom bonded to the arylene group, wherein the multiple parallel ring is a ring-forming element which may contain 1 to 9 nitrogen atoms or1 group 16 element in addition to the nitrogen atom bonded to the arylene group,

When L is a carbon-nitrogen single bond, D is a carbon-nitrogen single bond, a conjugated or unconjugated five-or six-sided ring containing a nitrogen atom of the above L, a substituted or unsubstituted ring in which the conjugated or unconjugated five-or six-sided ring is a substituted or unsubstituted ring, a group 16 element is a ring-forming element, 1 or 2 nitrogen atoms are a ring-forming element, a is a heterocyclic ring having a carbon number of 10 to 40, an aryl group containing a carbon atom bonded to the above L is contained, a ring structure in which the above heterocyclic ring contains a ring formed with the aryl group containing a carbon atom bonded to the above L, in which the above ring structure contains a boron atom and an oxygen atom as ring-forming elements, or a five-or six-sided ring structure contains conjugated 2 nitrogen atoms. )

The compound represented by the above chemical formula 1 may represent, for example, one of the following chemical formulas 1A to 1D:

Chemical formula 1A:

(in the above chemical formula 1A,

R ₁₁ and R ₁₂ are each independently one selected from the group consisting of hydrogen, deuterium, halogen, hydroxy, cyano, nitro, substituted or unsubstituted amino, amidino, hydrazino, hydrazono, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted alkoxy, substituted or unsubstituted thioether, substituted or unsubstituted cycloalkyl, substituted or unsubstituted cycloalkenyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted heterocycloalkenyl, substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, substituted or unsubstituted heteroaryl and substituted or unsubstituted heteroaryloxy, which may form a substituted or unsubstituted ring by bonding with an adjacent substituent,

S is an integer of 1 or 2,

T is an integer of 4 or 5,

N11 and n12 are each independently integers from 1 to 4,

When n11 and n12 are 2 or more, the structures in brackets may be the same or different from each other,

R ₁₁ and R ₁₂ may form a substituted or unsubstituted ring by bonding with adjacent substituents. )

Chemical formula 1B:

(in the above chemical formula 1B,

X is a single bond, CR ₂₆R₂₇、NR₂₈, O or S,

R ₂₁ to R ₂₈ are each independently one selected from the group consisting of hydrogen, deuterium, halogen, hydroxyl, cyano, nitro, substituted or unsubstituted amino, amidino, hydrazino, hydrazono, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted alkoxy, substituted or unsubstituted thioether, substituted or unsubstituted cycloalkyl, substituted or unsubstituted cycloalkenyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted heterocycloalkenyl, substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, substituted or unsubstituted heteroaryl and substituted or unsubstituted heteroaryloxy, which may form a substituted or unsubstituted ring by bonding with an adjacent substituent,

N23 to n25 are each independently integers of 1 to 4,

In the case where n23 to n25 are 2 or more, the structures in brackets may be the same or different from each other,

R ₂₃ to R ₂₈ may form a substituted or unsubstituted ring by bonding with an adjacent substituent. )

Chemical formula 1C:

(in the above chemical formula 1C,

Y is a single bond, CR ₃₆R₃₇、NR₃₈, O or S,

R ₃₁ to R ₃₈ are each independently one selected from the group consisting of hydrogen, deuterium, halogen, hydroxyl, cyano, nitro, substituted or unsubstituted amino, amidino, hydrazino, hydrazono, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted alkoxy, substituted or unsubstituted thioether, substituted or unsubstituted cycloalkyl, substituted or unsubstituted cycloalkenyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted heterocycloalkenyl, substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, substituted or unsubstituted heteroaryl and substituted or unsubstituted heteroaryloxy, which may form a substituted or unsubstituted ring by bonding with an adjacent substituent,

Z ₁ and Z ₂ are each independently selected from one of the group consisting of hydrogen, hydroxyl and substituted or unsubstituted alkyl, or form a ring by bonding,

N31, n32, n34 and n35 are each independently integers from 1 to 4,

N33 is an integer of 1 to 2,

In the case where n31 to n35 are 2 or more, the structures in brackets may be the same or different from each other,

R ₃₁ to R ₃₈ may form a substituted or unsubstituted ring by bonding with an adjacent substituent. )

Chemical formula 1D:

(in the above chemical formula 1D,

Z is a single bond, CR ₄₅R₄₆、NR₄₇, O or S,

R ₄₁ to R ₄₇ are each independently one selected from the group consisting of hydrogen, deuterium, halogen, hydroxyl, cyano, nitro, substituted or unsubstituted amino, amidino, hydrazino, hydrazono, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted alkoxy, substituted or unsubstituted thioether, substituted or unsubstituted cycloalkyl, substituted or unsubstituted cycloalkenyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted heterocycloalkenyl, substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, substituted or unsubstituted heteroaryl and substituted or unsubstituted heteroaryloxy, which may form a substituted or unsubstituted ring by bonding with an adjacent substituent,

N41 is an integer of 1 to 2,

N42 is an integer of 1 to 3,

N43 and n44 are each independently integers from 1 to 4,

In the case where n41 to n44 are 2 or more, the structures in brackets may be the same or different independently from each other,

R ₄₁ to R ₄₇ may form a substituted or unsubstituted ring by bonding with an adjacent substituent. )

The compound represented by chemical formula 1 may be, for example, one or more selected from the group consisting of the following compounds T-1 to T-28, but is not limited thereto.

In the case of applying the luminescent type organic nanoparticle to the use of a display, it is preferable to use a boron compound having a narrower full width at half maximum for higher color purity.

The boron compound suitable for use in a display is not particularly limited, and may be, for example, a boron compound represented by the following chemical formula 2.

Chemical formula 2:

(in the above chemical formula 2,

N1 and n4 are each independently integers from 1 to 4,

N2, n3 and n5 are each independently integers from 1 to 3,

The boron compound represented by chemical formula 2 may be one or more of the group consisting of the following compounds D-1 to D-30, for example, but is not limited thereto.

Further, the boron compound suitable for use in a display may be a boron compound as represented by the following chemical formula 3.

Chemical formula 3:

(in the above-mentioned chemical formula 3,

C ₁ to C ₃ have a five-sided or six-sided ring structure respectively,

Y ₁ and Y ₂ are each independently fluorine or alkoxy,

A and b are each independently integers from 1 to 4,

The compound represented by the above chemical formula 3 may be represented by, for example, the following chemical formula 3A:

chemical formula 3A:

(in chemical formula 3A, R ₅₁ to R ₅₃、Y₁ and Y ₂ may be defined as above, and a and b are each independently integers of 1 to 3).

The boron compound represented by chemical formula 3 may be, for example, one or more selected from the group consisting of the following compounds B-1 to B-33, but is not limited thereto.

The organic nanoparticle may have a core-shell structure in which an organic phosphor is surrounded by a surfactant, in which case the organic nanoparticle has the following advantages: the shape and size become uniform, thereby increasing the yield of the organic nanoparticles, and the size of the luminescent organic nanoparticles can be adjusted by adjusting the concentration of the surfactant, and the characteristics of the color conversion film can be improved, but is not limited thereto.

The surfactant may be one or more selected from the group consisting of anionic surfactants, cationic surfactants, zwitterionic surfactants, and nonionic surfactants, but is not limited thereto.

The anionic surfactant means that the hydrophilic group of the anionic surfactant is one or more selected from the group consisting of carboxylate, sulfate, sulfonate and phosphate when dissolved in water, but is not limited thereto.

The cationic surfactant is a surfactant having a hydrophilic group and a cation when dissolved in water, and may include a nitrogen atom having a positive charge, and specifically may be tetrabutylammonium oleate (Tetrabutylammonium oleate, TBAOleate), but is not limited thereto.

The term "zwitterionic surfactant" refers to a surfactant which, when dissolved in water, has the properties of an anionic surfactant in the alkaline region and a cationic surfactant in the acidic region.

The nonionic surfactant is a surfactant having a hydrophilic group that is not ionized when dissolved in water, and is a surfactant that is not charged even when dissolved in water, and may be, for example, triton X100 (Triton X100) having a hydrophilic polyethylene oxide chain and a lipophilic or hydrophobic aromatic hydrocarbon group, but is not limited thereto.

In the present invention, the method of preparing the light emitting type organic nanoparticle is not particularly limited, and for example, the light emitting type organic nanoparticle may be prepared by including the steps of: a step (S1) of preparing a first mixture by mixing an organic phosphor and a surfactant; a step (S2) of adding an antisolvent (anti-solvent) for the organic fluorescent material to the first mixture to prepare a dispersion liquid; and (S3) dialyzing the dispersion, and drying the dialyzed dispersion.

Step (S1)

The description of the organic phosphor and the surfactant constituting the first mixture of step (S1) is as described above.

In step (S1), the mixing ratio (molar ratio) of the organic phosphor and the surfactant may be 1:20 to 1:1000, preferably 1:200 to 1:800, more preferably 1:400 to 1:600, but is not limited thereto. When the mixing ratio (molar ratio) of the organic fluorescent material and the surfactant satisfies the above range, uniform light-emitting organic nanoparticles having a particle size can be obtained.

If the concentration of the surfactant is not less than the critical micelle concentration, the hydrophobic portion of the surfactant surrounds the organic nanoparticle to form micelles, and the micelles are dispersed in the solvent. This makes the shape and size of the luminescent organic nanoparticle uniform, thereby improving the yield of the luminescent organic nanoparticle. In addition, the particle size of the light-emitting organic nanoparticles can be adjusted by adjusting the concentration of the surfactant, and thus, the characteristics of the color conversion film can be further improved.

Step (S2)

The antisolvent added in step (S2) may be one or more selected from the group consisting of an aqueous solvent, an alcohol-based solvent, a ketone-based solvent, an ether-based solvent, a sulfoxide-based solvent, and an ester-based solvent, but is not limited thereto.

The aqueous solvent may be, for example, one of water, aqueous hydrochloric acid and aqueous sodium hydroxide, the alcohol solvent may be, for example, one or more selected from the group consisting of methanol, ethanol, isopropanol, n-propanol and 1-methoxy-2-propanol, the ketone solvent may be, for example, one or more selected from the group consisting of acetone, methyl ethyl ketone, methyl isobutyl ketone and cyclohexanone, the ether solvent may be, for example, one or more selected from the group consisting of dimethyl ether, diethyl ether and tetrahydrofuran, the sulfoxide solvent may be, for example, dimethyl sulfoxide, and the ester solvent may be, for example, alkyl ester, but is not limited thereto.

Step (S3)

Step (S3) is a step of removing excess surfactant from the dispersion to increase the yield of the luminescent organic nanoparticles.

The dialysis apparatus used in step (S3) may be, for example, a dialysis tube composed of cellulose acetate, but is not limited thereto.

The drying of the dispersion dialyzed in step (S3) may be, but is not limited to, concentrating the dispersion under vacuum for 10 to 12 hours.

Composition for color conversion film

According to still another aspect of the present invention, there is provided a composition for a color conversion film, comprising the aforementioned luminescent organic nanoparticle and a water-soluble polymer resin.

The water-soluble polymer resin may have a weight average molecular weight of 5000g/mol to 100000g/mol and a hydration degree of 70% to 100%, and in this case, exhibits an appropriate surface activity, whereby the characteristics of the color conversion film may be further improved, but is not limited thereto.

The water-soluble polymer resin may be one or more selected from the group consisting of nonionic water-soluble polymers, anionic water-soluble polymers and cationic water-soluble polymers, but is not limited thereto.

The nonionic water-soluble polymer may be, for example, one or more polymers or copolymers selected from the group consisting of polyvinyl alcohol, polyethylene oxide, polyacrylamide and polyvinylpyrrolidone, the anionic water-soluble polymer may be, for example, one or more polymers or copolymers selected from the group consisting of polyacrylic acid and derivatives thereof, polystyrene sulfonic acid, polysilicic acid, polyphosphoric acid, polyethylene sulfinic acid, poly [3- (vinyloxy) propane-1-sulfonic acid ], poly (4-vinylphenol), poly (4-vinylphenol sulfuric acid), poly (vinylphosphoric acid), poly (maleic acid), poly (2-methyl ethylene oxide-1-sulfonic acid), poly (3-methacryloxypropane-1-sulfonic acid) and poly (4-vinylbenzoic acid), the cationic water-soluble polymer may be, for example, one or more polymers or copolymers selected from the group consisting of polyethyleneimine, polyamine, polyamidoamine, polydienyl dimethyl ammonium chloride, poly (4-vinylbenzyl trimethyl ammonium salt), poly [ (dimethylimino) hexamethylenedibromo ], poly (2-vinyl piperidine), a salt of poly (2-vinyl piperidine) and a copolymer thereof, but not limited thereto.

The explanation about the luminescent organic nanoparticle is as described above.

The content of the light-emitting organic nanoparticles may be 1 to 20 parts by weight with respect to 100 parts by weight of the water-soluble polymer resin, but is not limited thereto. In the case where the amount of the luminescent organic nanoparticles is too small, the color conversion efficiency may be lowered, whereas in the case where the content of the organic nanoparticles is too large, the aggregation property between the nanoparticles may be enhanced, resulting in an increase in the particle size and occurrence of a extinction phenomenon.

In order to secure high thermal stability of the color conversion film, discoloration (decrease in transmittance) caused by heat is prevented, and the composition for a color conversion film may further include a crosslinking agent, but is not limited thereto.

The crosslinking agent may be, for example, one or more selected from the group consisting of glutaraldehyde, glyoxal, maleic acid, citric acid, sodium trimetaphosphate, sodium hexametaphosphate, dianhydride, succinic acid, suberic acid, sulfosuccinic acid, and K ₂S₂O₈ as a radical crosslinking agent, but is not limited thereto.

In the case where the water-soluble polymer resin is PVA, in order to improve thermal stability and transmittance retention, suberic acid or K ₂S₂O₈ as a radical crosslinking agent is preferably used as a crosslinking agent, but is not limited thereto.

The content of the crosslinking agent may be 0.01 to 20 parts by weight with respect to 100 parts by weight of the water-soluble polymer resin, but is not limited thereto.

The composition for a color conversion film further includes a light scattering agent in order to increase light absorption efficiency by generating a light scattering effect, improve dispersibility, and ensure high thermal stability and flame retardancy, but is not limited thereto.

The light scattering agent is, for example, one or more inorganic oxide particles selected from the group consisting of TiO ₂,ZnO,Fe₃O₄,CeO₂,MoO₂,Ag₂ O, cuO, and NiO, and may be inorganic oxide particles having an average particle size of 200nm to 400nm, but is not limited thereto.

The content of the light scattering agent may be 1 to 20 parts by weight with respect to 100 parts by weight of the water-soluble polymer resin, but is not limited thereto.

Color conversion film

According to another aspect of the present invention, there is provided a color conversion film prepared using the aforementioned composition for a color conversion film.

For the color conversion film, the aforementioned composition for a color conversion film can be prepared as a color conversion film by a bar coating method, a sol-gel method, an inkjet printing method, a roll coating method, a spin coating method, a drop casting method, or the like.

For example, in the case of preparing a color conversion film by a bar coating method, the composition for a color conversion film is sprayed on a glass substrate, and then a thin film is formed by a bar coating method, and annealing is performed in an oven at 50 to 70 ℃ for several hours to remove a solvent, whereby the color conversion film can be prepared, but the present invention is not limited thereto.

The thickness of the color conversion film may be 200 μm or less, preferably 180 μm or less, more preferably 150 μm, but is not limited thereto.

Display device

According to still another aspect of the present invention, there is provided a display device including the foregoing color conversion film.

The display device of the present invention includes a Liquid crystal display device (Liquid CRYSTAL DISPLAY DEVICE), an organic light emitting display device, a micro LED display, and the like.

The organic phosphor for a display device has a full width at half maximum for higher color purity. Accordingly, the organic fluorescent material used for the display device may be the aforementioned boron compound having a luminous efficiency of 80% or more, but is not limited thereto.

In general, a liquid crystal display device includes 2 substrates. Specifically, the method comprises the following steps: a lower substrate having a switching element including a thin film transistor; an upper substrate having a common electrode, the upper substrate being opposite to the lower substrate; and liquid crystal injected between the upper substrate and the lower substrate.

In contrast, in the organic light emitting device, micro LEDs may be formed on 1 substrate. A switching element including a thin film transistor is formed at a lower portion, and an organic light emitting element or a micro LED turned off/on by the switching element may be formed at an upper portion of the switching element. In the case of an organic light emitting element or a micro LED, it is possible to use a single substrate, but it is usual to provide an upper substrate, and an antireflection film or the like is formed on the upper substrate.

In the display device of the present invention, the upper substrate may be formed by generally including a base film, an antireflection film, and a color conversion film, and the color conversion film may be formed using the light-emitting organic nanoparticle of the present invention.

In the case of a liquid crystal display device, a light source emitted from a backlight is converted into three primary colors by a color conversion film, and in the case of a display device employing an organic light emitting element or a micro LED, a single-color organic light emitting element or a micro LED is applied and is emitted in three primary colors by the color conversion film of the present invention.

Light emitting diode device

According to still another aspect of the present invention, there is provided a light emitting diode device including the foregoing color conversion film.

The light emitting diode device is a light emitting element that emits light by applying a voltage to a PN junction diode of a compound semiconductor, and corresponds to a light emitting element that emits light by energy generated when holes and electrons move and combine between p-n, and is understood to include the concept of an organic light emitting element.

The full width half maximum shadow width of the organic phosphor for the light emitting diode device to achieve a high color rendering index. Accordingly, the organic phosphor used for the light emitting diode device may be the aforementioned delayed fluorescent material having a luminous efficiency of 80% or more, but is not limited thereto.

Generally, light emitting diode devices are classified into chip LEDs having high brightness, ultra-small size and thin type characteristics, top LEDs, ultra-high brightness, high humidity resistance and heat resistance outdoor displays, lamp LEDs for electronic screens and the like, according to the purpose of use.

The light emitting diode device of the present invention may include a substrate and an LED chip disposed on the substrate. The color conversion film of the present invention can absorb light emitted from the above-described LED chip (or LED backlight) and convert it into light of other long wavelength using the light-emitting organic nanoparticle of the present invention.

Hereinafter, embodiments of the present specification are described in more detail. However, the following experimental results are merely representative experimental results in the above examples, and the scope and content of the present specification should not be interpreted by narrowing down or limiting the examples and the like. Various effects of the various examples of the present specification itself, which are not explicitly set forth below, are specifically described in the corresponding sections.

Preparation example: preparation of organic fluorescent material

< Preparation example 1: preparation of Compound T-3 ]

(1) Synthesis of Compound T-3

To a mixture of tris (dibenzylideneacetone) dipalladium (tris (dibenzylideneacetone) dipalladium) (0) (Pd ₂(dba)₃, 0.08 mmol), tris-tert-butylphosphine (tri-tert-butylphosphine) (t-Bu) 3P,1.86 mmol), sodium tert-butoxide (NaOt-Bu, 5.15 mmol) and anhydrous o-xylene (anhydrous o-xylene) were added 2- (4-bromophenyl) -4,6-diphenyl-1,3,5-triazine (2- (4-bromophenyl) -4,6-diphenyl-1,3, 5-triazine) (Trz, 8.85 mmol) and 10, 15-dihydro-5H-diindo [3,2-A:3',2' -C ] carbazole (10, 15-dihydro-5H-di indolo [3,2-a:3',2' -C ] carbazole) (molten carbazole (fuzed carbazole) in a molar ratio of 3:1, respectively. The mixture with Trz and melted carbazole added was flushed with nitrogen and a non-reactive atmosphere was created under vacuum. After that, the mixture was refluxed at 135℃for 12 hours, and a certain reaction was carried out. The mixture after completion of the above reaction was washed several times with methylene chloride and deionized water. In the washed mixture, the water was discarded and the dichloromethane layer was dried over anhydrous sodium sulfate. The mixture subjected to the above-mentioned drying process was filtered using a filter, and the remaining solvent was evaporated using a rotary evaporator, thereby synthesizing the final product 5, 10, 15-tris (4- (4, 6-diphenyl-1,3, 5-triazin-2-yl) phenyl) -10, 15-dihydro-5H-diindolo [3,2-a:3',2' -c ] carbazole (5,10,15-tris(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-10,15-dihydro-5H-diindolo[3,2-a:3',2'-c]carbazole)( or less, hereinafter referred to as "Ttrz-DI") purified by silica gel column chromatography.

The reaction for synthesizing the final product was summarized as follows.

(2) Monohydronuclear magnetic resonance (¹ H-NMR) data for Compound T-3

FIG. 1 shows hydrogen nuclear magnetic resonance data of Ttrz-DI. The above-mentioned hydrogen nuclear magnetic resonance data were measured by using a 400MHz brookfield nuclear magnetic resonance spectrometer.

Referring to FIG. 1, it was confirmed that Trz and molten carbazole were reacted in a molar ratio of 3:1, respectively, to synthesize Ttrz-DI.

(3) Analysis of photophysical Properties of Compound T-3

Part (a) of FIG. 2 shows UV-Vis, room temperature photoluminescence and low temperature photoluminescence spectra of Ttrz-DI in toluene.

Referring to part (a) of FIG. 2, the initial value of RTPL shows 2.83eV in on-set in the singlet state (SINGL ET STATE) of Ttrz-DI, and the initial value of LTPL shows 2.80eV in on-set in the triplet state (TRIPLET STATE) of Ttrz-DI in 77K toluene solution. Therefore, the difference between the energy in the triplet state and the energy in the singlet state of Ttrz-DI corresponds to 0.03eV.

Part (b) of fig. 2 shows time resolved photoluminescence of Ttrz-DI in a solvent. The solvent is toluene (Tol) or Methylene Chloride (MC).

Referring to part (b) of fig. 2, ttrz-DI has two decays (decay) of transient decay (decay) and delayed decay (DELAYED DECAY), which can be confirmed, showing a Thermally Activated Delayed Fluorescence (TADF) characteristic.

< Preparation example 2: preparation of Compound T-9)

Referring to Nature 492, pp.234-238 (2012) synthesizes a compound T-9 (hereinafter, referred to as "4 CzIPN") having the following chemical formula.

< Preparation example 3: preparation of Compound D-23>

(1) Synthetic intermediates

A mixture of 1,3, 5-tribromobenzene (1 g,3.18 mmol), di (naphthalen-2-yl) amine (2.74 g,10.17 mmol), P (t-Bu) ₃ (0.8 mL,3.17 mmol) and NaOBut (1.84 g,19.15 mmol) in anhydrous toluene (60 mL) was replaced with argon, pd ₂(dba)₃ (0.26 g,0.28 mmol) was charged and stirred at 160℃for 18 hours. After the completion of the reaction, the compound was filtered, washed with dichloromethane and hexane, concentrated, and recrystallized from dichloromethane and hexane to obtain the following intermediate (2.6 g, 93%).

The reactions for synthesizing the above intermediates are summarized as follows.

(2) Synthesis of Compound D-23

After substituting a mixture of intermediate (1 g,1.14 mmol) in o-dichlorobenzene (15 ml) with argon, BBr ₃ (0.31 ml,2.5 mmol) was slowly added dropwise at room temperature. After 10 minutes, the reaction was refluxed at a temperature of 200 ℃ for 20 hours. When the reaction was completed, the reaction was diluted with toluene and concentrated by filtration through a pad of silica gel. For the residue, hexane and methylene chloride were purified by column chromatography to obtain compound D-23 (0.2 g, 20%).

The reaction for synthesizing the above-mentioned compound D-23 (hereinafter referred to as "TANP") is summarized as follows.

< Preparation example 4: preparation of Compound D-13 ]

Referring to Angew.chem.int.ed.57, pp 11316-11320 (2018), a compound D-13 (hereinafter, referred to as "CzDABNA") having the following chemical formula was synthesized.

< Preparation example 5: preparation of Compound B-23)

Compound B-23 (hereinafter, referred to as "4 tBuMB") having the following chemical formula was synthesized with reference to ACS appl. Mater. Interfaces 13, pp 17882-17891 (2021).

< Preparation example 6: preparation of Compound B-33 ]

Compound B-33 (hereinafter, referred to as "tPhBODIPY") having the following chemical formula was synthesized with reference to adv.optical mate.8, 2000483 (2020).

Preparation example 1: preparation of luminescent organic nanoparticles

< Preparation example 1-1>

Ttrz-DI was dissolved in tetrahydrofuran to prepare a solution (0.5 mM). A solution (0.1M) was prepared by dissolving a nonionic surfactant (triton X-100) in additional tetrahydrofuran as well. A first mixture was prepared by adding the surfactant solution (0.36 mL) and tetrahydrofuran (0.14 mL) to the Ttrz-DI solution (0.10 mL). A dispersion was prepared by mixing the above first mixture with 5.40mL of deionized water. The above dispersion was dialyzed using a cellulose acetate tube for 12 hours to remove residual surfactant, and the solvent was concentrated in vacuo to prepare green organic nanoparticles (hereinafter, referred to as "Ttrz-DI NP").

< Preparation examples 1 to 2>

Green Ttrz-DI NP was prepared by the same method as in preparation example 1-1, except that tert-butylammonium oleate (tert-butyl ammonium oleate, TBAOleate) was used as a surfactant instead of triton X-100.

< Preparation examples 1 to 3>

Green organic nanoparticles were prepared by the same method as in preparation example 1-1, except that 4CzIPN was used as an organic phosphor instead of Ttrz-DI.

< Preparation examples 1 to 4>

Green organic nanoparticles were prepared by the same method as in preparation example 1-1, except that TNAP was used as an organic phosphor instead of Ttrz-DI.

< Preparation examples 1 to 5>

Green organic nanoparticles were prepared by the same method as in preparation example 1-1, except that tPhBODIPY was used as an organic phosphor instead of Ttrz-DI.

< Preparation examples 1 to 6>

Blue organic nanoparticles were prepared by the same method as in preparation example 1-1, except that CzDABNA was used as an organic phosphor instead of Ttrz-DI.

< Preparation examples 1 to 7>

Blue organic nanoparticles were prepared by the same method as in preparation examples 1 to 6, except that TBAOleate was used as a surfactant instead of the triton X-100.

< Preparation examples 1 to 8>

Red organic nanoparticles were prepared by the same method as in preparation example 1-1, except that 4tBuMB was used as an organic phosphor instead of Ttrz-DI.

< Preparation examples 1 to 9>

Red organic nanoparticles were prepared by the same method as in preparation examples 1 to 8, except that TBAOleate was used as a surfactant instead of triton X-100.

Comparative preparation examples 1 to 1]

Green Ttrz-DI NP was prepared by the same method as in preparation example 1-1, except that the surfactant solution was not mixed.

Comparative preparation examples 1-2 ]

Blue organic nanoparticles were prepared by the same method as in preparation examples 1 to 6, except that the surfactant solution was not mixed.

Comparative preparation examples 1 to 3]

Red organic nanoparticles were prepared by the same method as in preparation examples 1 to 8, except that the surfactant solution was not mixed.

Experimental example 1: particle size of organic nanoparticles

The particle size was measured with respect to the organic nanoparticles prepared according to the above preparation example 1, and the results thereof are shown in table 1 below.

TABLE 1

	Average (mu m)	Standard deviation (μm)	Minimum (mu m)	Maximum (mum)
					PREPARATION EXAMPLE 1-1	0.12	0.08	0.05	0.48
PREPARATION EXAMPLES 1-2	0.14	0.12	0.11	0.59
					Preparation examples 1 to 6	0.13	0.24	0.05	1.53
Preparation examples 1 to 7	0.13	0.25	0.05	1.57
					Preparation examples 1 to 8	0.16	0.07	0.04	0.41
Preparation examples 1 to 9	0.17	0.10	0.06	0.52
					Comparative preparation example 1-1	14.14	10.99	1.62	98.22
Comparative preparation examples 1 to 2	15.24	11.50	1.65	99.89
					Comparative preparation examples 1 to 3	17.38	4.25	10.70	32.34

As is clear from table 1, since the fluorescent material is aggregated without using the surfactant, the average particle diameter is increased by about 100 times or more as compared with the case of using the surfactant, and thus the organic particles of the micron unit are obtained, whereas in the case of using the surfactant, the organic particles are more uniform and smaller.

Experimental example 2: evaluation of particle diameter and optical Properties based on the State of organic nanoparticles

Fig. 3a is a graph showing the size and emission wavelength of particles according to the state change of Ttrz-DI in the case of using the triton X-100 as a surfactant, and fig. 3b is a graph showing the size and emission wavelength of particles according to the state change of Ttrz-DI in the case of using TBAOleate as a surfactant. Referring to fig. 3, it can be seen that the positions of the emission spectrum peaks become different according to what state Ttrz-DI is. This difference is caused by the change in the particle diameter of the phosphor particles. Specifically, when Ttrz-DI is in a solution state, the organic phosphor particles haveThe size distribution of the units increases because the particles form large aggregates (aggregation) in the bulk film state, and the emission spectrum shifts to the long wavelength side. In contrast, when Ttrz-DI is a dispersion, the particle size is uniformly distributed on the μm to nm scale, and the peak of the luminescence spectrum is located between the solution state and the thin film state.

After preparing a solution in which 50mg to 100mg of the organic nanoparticles prepared according to preparation example 1 and green QD were dispersed in octene (1 ml), optical characteristics and average particle diameters were measured, and the results thereof are shown in table 2 below. At this time, the normal-temperature photoluminescence spectrum was measured by using a JASCO-FP 8500 apparatus, and the average particle diameter was measured by an optical microscope for the absolute photoluminescence quantum yield (Photoluminescence Quantum Yield, PLQY) value by using an integrating sphere incorporated in the JASCO-FP 8500 apparatus.

TABLE 2

As can be seen from table 2, the average particle size of the phosphor particles prepared using the surfactant has a size of 10 times greater than that of the green QD particles.

Preparation example 2: preparation of base film

< Preparation example 2-1>

A mixed solution was prepared by mixing 0.49g of polyvinyl alcohol (PVA, weight average molecular weight 13000g/mol to 23000g/mol, hydration degree 87% -89%) and 0.01g of Suberic Acid (SA) in 5.0mL of deionized water, and heating at 80℃for 2 hours. After cooling the mixed solution, 1mL of the solution was sprayed on the glass substrate, and a thin film was formed by a bar coating method. To remove the solvent, the base film was prepared by storing in an oven at 60℃for 4 hours and performing a crosslinking reaction at 120℃for 2 hours. The thickness of the film prepared by Alpha-step measurement was 10.0. Mu.m.

< Preparation example 2-2>

A base film was produced in the same manner as in production example 2-1 except that 1.0g of PVA and 0.05g of SA were used. The thickness of the film prepared by Alpha-step measurement was 10.0. Mu.m.

< Preparation examples 2 to 3>

A base film was produced in the same manner as in production example 2-1, except that 0.4g of PVA,0.1g of polyvinylpyrrolidone, and 0.01g of SA were mixed with 3.0mL of deionized water to prepare a mixed solution. The thickness of the film prepared by Alpha-step measurement was 10.0. Mu.m.

< Preparation examples 2 to 4>

A base film was prepared by the same method as in preparation example 2-1, except that a mixed solution was prepared by mixing 0.4g of PVA,0.2g of PVP, and 0.01g of SA in 3.5mL of deionized water. The thickness of the film prepared by Alpha-step measurement was 10.0. Mu.m.

< Preparation examples 2 to 5>

A base film was produced by the same method as in production example 2-1, except that 1.0g of PVA,1.0g of PVP, and 0.05g of SA were mixed with 5.0mL of deionized water to prepare a mixed solution. The thickness of the film prepared by Alpha-step measurement was 10.0. Mu.m.

< Preparation examples 2 to 6>

A base film was produced by the same method as in production example 2-1, except that a mixed solution was prepared by mixing 0.5g of PVA,1.0g of PVP, and 0.05g of SA in 5.0mL of deionized water. The thickness of the film prepared by Alpha-step measurement was 10.0. Mu.m.

< Preparation examples 2 to 7>

A base film was produced in the same manner as in production example 2-1 except that 0.5g of PVA,0.5g of PVP, and 0.001g of radical crosslinking agent K ₂S₂O₈ were mixed with 5.0mL of deionized water to prepare a mixed solution. The thickness of the film prepared by Alpha-step measurement was 10.0. Mu.m.

Comparative preparation example 2-1 ]

A base film was produced by the same method as in production example 2-1, except that a mixed solution was prepared by mixing 2.0g of PVA with 10mL of deionized water. The thickness of the film prepared by Alpha-step measurement was 10.0. Mu.m.

Experimental example 3: evaluation of clarity of base film

The transparency of the base film prepared in preparation example 2 was measured after being left at room temperature (25 ℃) for 1 hour at 130 ℃,180 ℃ and 200 ℃ respectively, and the results are shown in table 3 below.

TABLE 3 Table 3

As can be seen from table 3, the base film prepared using SA as the crosslinking agent is excellent in heat stability and transmittance retention ability as compared with the base film without using the crosslinking agent. In particular, in the cases of preparation examples 2-2 and preparation examples 2-7, the heat stability and transmittance retention ability shown were the most excellent, and almost no color change of the film occurred after leaving for 1 hour at a temperature of 200 ℃. FIG. 4a is a graph showing the result of measuring the transparency of the base film of preparation 2-2 after the base film was left at room temperature (25 ℃) for 1 hour at 130℃and at 180℃and at 200℃respectively, and FIG. 4b is a graph showing the result of the base film of preparation 2-2 after the base film was left at 200℃for 1 hour.

Experimental example 4: evaluation of hardness of base film

The pencil hardness was measured with respect to the base film prepared in the above preparation example 2, and was evaluated as "o" when no scratch was found, as "Δ" when a weak scratch was found, and as "x" when a scratch was found to be deep. The results are shown in table 4 below.

TABLE 4 Table 4

Referring to table 4, it is apparent that in the base film prepared using SA as the crosslinking agent, almost no film damage occurred at the hardness 2B and 2H, but only weak damage occurred at the hardness 4H, whereas in the base film not using the crosslinking agent, film damage occurred not only at the hardness 4H but also at the hardness 2H. From this, it is found that the hardness of the base film can be improved by the crosslinking agent. Fig. 5a is a photograph taken after pencil hardness was measured for preparation example 2-1, and fig. 5b is a photograph taken after pencil hardness was measured for comparative preparation example 2-1.

Preparation example 3: preparation of color conversion film (1)

< Preparation example 3-1>

1G of PVA (weight average molecular weight 13000g/mol to 23000g/mol, hydration degree 87% -89%) was dissolved in 9g of deionized water to prepare a 10 weight percent aqueous PVA solution. Ttrz-DI NP (0.3 g dispersion) of preparation 1-1 above was mixed with the aqueous PVA solution (2.7 g) above. After spraying about 1mL of the mixed solution onto a glass substrate, a thin film was formed by a bar coating method. To remove the solvent, an oven anneal at 60 ℃ was performed for 4 hours, thereby preparing a color conversion film.

< Preparation example 3-2>

A color conversion film was prepared by the same method as in preparation example 3-1, except that 4CzIPN organic nanoparticles of preparation example 1-3 were used instead of Ttrz-DI NP of preparation example 1-1.

< Preparation example 3-3>

A color conversion film was prepared by the same method as in preparation example 3-1, except that TNAP organic nanoparticles of preparation example 1-4 were used instead of Ttrz-DI NP of preparation example 1-1.

< Preparation examples 3 to 4>

A color conversion film was prepared by the same method as in preparation example 3-1, except that 4tBuMB organic nanoparticles of preparation example 1-8 were used instead of Ttrz-DI NP of preparation example 1-1.

Comparative preparation example 3-1 ]

Polymethyl methacrylate (PMMA, weight average molecular weight 120000g/mol,5 g) was dissolved in 5mL of chloroform to prepare a 10w% PMMA aqueous solution. To this solution (2.7 g), a Quantum Dot (QD) solution (1 mM/chloroform, 0.3 g) of InP/ZnSe/ZnS series as inorganic green light-emitting particles was mixed. After spraying 1mL of the mixed solution onto a glass substrate, a thin film was formed by a bar coating method. To remove the solvent, the solvent was removed in an oven at 40 ℃ for 3 hours, thereby preparing a color conversion film.

Comparative preparation example 3-2 ]

A color conversion film was prepared by the same method as in preparation example 3-1, except that the same amount of Ttrz-DI was dissolved in THF instead of Ttrz-DI NP of preparation example 1-1.

Experimental example 5: evaluating optical properties of color conversion film

The evaluation of optical characteristics was performed with the color conversion film of preparation example 3 as an object, specifically, UV-Vis absorption spectrum was measured using JASCO V-750, and normal temperature photoluminescence spectrum was measured using JASCO-FP 8500 equipment. The photoluminescence quantum yield (PLQY) value and Color Conversion Efficiency (CCE) were measured using an integrating sphere incorporated in the JASCO-FP 8500 apparatus, and the results are shown in table 5 below. Among them, a blue LED having an emission wavelength of 400nm was used as excitation light to excite and measure each color conversion film. The color conversion efficiency measurement method will be described in more detail with reference to fig. 6. Fig. 6 shows the optical characteristics and the color conversion efficiency calculation method of the color conversion film of production example 3-1, with the proportion (%) of the green light-emitting region (B) corresponding to the color conversion efficiency based on the blue light-emitting region (a) which is the blue incident light absorbed by the color conversion film, and the green light-emitting region (B) which is the green release region released by the color conversion film.

TABLE 5

As can be seen from a comparison of table 5 and table 2, PLQY of the color conversion films of preparation examples 3-1 to 3-4 showed a tendency to be further improved in solution, whereas PLQY of the color conversion film of preparation example 3-1 showed a tendency to be significantly reduced in solution. This is due to the large QD-QD quenching that occurs.

Experimental example 6: assessing UV stability of color conversion films

The color conversion film of preparation example 3 was subjected to continuous exposure to UV (wavelength: 365 nm) for 120 hours, and then the luminescence intensity was measured by a normal temperature luminescence spectrum using a JASCO-FP 8500 apparatus. The results are shown in table 6 below.

TABLE 6

As can be seen from table 6, the color conversion film prepared using the organic nanoparticles of the present invention has excellent UV stability compared to the conventional QD film. Further, as is clear from a comparison of preparation example 3-1 and comparative preparation example 3-2, the UV stability of the color conversion film prepared using the organic nanoparticles of the present invention was increased by about 1.6 times as compared to the color conversion film prepared using the organic substance itself. FIG. 7 is a graph showing the results of evaluation of light resistance after 120 hours of UV exposure in preparation example 3-1 and comparative preparation example 3-2.

Experimental example 7: evaluating the ambient temperature stability of the color conversion film

The color conversion film of preparation example 3 was used as a target, and after leaving for 1 month at normal temperature, the amount of change in Color Conversion Efficiency (CCE) was measured. The results are shown in table 7 below.

TABLE 7

As is clear from table 7, the color conversion efficiency of the color conversion film prepared using the organic nanoparticles of the present invention changed by 1% or less, and the color conversion efficiency was extremely excellent in persistence as compared with the conventional QD film.

Preparation example 4: preparation of color conversion film (2)

PREPARATION EXAMPLE 4-1

After PVA and SA were mixed with deionized water at a weight ratio of 49:1, thereby preparing a 15 weight percent aqueous polyvinyl alcohol solution (PVA-SA, 15 wt%) and heated at a temperature of 80℃for 3 hours. 4tBuMB organic nanoparticles (4.0 wt% dispersion, 0.08 mL) and TiO ₂ solution (6.0 wt% aqueous solution, 0.05 mL) of preparation examples 1-8 above were mixed with the PVA-SA aqueous solution (15 wt%,1.0 mL) above. After spraying about 1mL of the mixed solution onto a glass substrate, a thin film was formed by a bar coating method. To remove the solvent, the film was stored in an oven at 60 ℃ for 4 hours, and a crosslinking reaction was performed at a temperature of 120 ℃ for 2 hours, thereby preparing a color conversion film.

< Preparation example 4-2>

A color conversion film was produced by the same method as in production example 4-1, except that the TiO ₂ solution was not used.

< Preparation example 4-3>

A color conversion film was produced in the same manner as in production example 4-1, except that 0.19mL of the organic nanoparticle and 0.10mL of the TiO ₂ solution were mixed with the PVA-SA aqueous solution (15 wt%,1.0 mL) described above.

< Preparation example 4-4>

A color conversion film was produced in the same manner as in production example 4-1, except that 0.19mL of the organic nanoparticle and 0.17mL of the TiO ₂ solution were mixed with the PVA-SA aqueous solution (15 wt%,1.0 mL) described above.

< Preparation examples 4 to 5>

A color conversion film was produced in the same manner as in production example 4-1, except that 0.35mL of the organic nanoparticle and 0.18mL of the TiO ₂ solution were mixed with the PVA-SA aqueous solution (15 wt%,1.0 mL) described above.

< Preparation examples 4 to 6>

A color conversion film was produced in the same manner as in production example 4-1, except that 0.46mL of the organic nanoparticle and 0.18mL of the TiO ₂ solution were mixed with the PVA-SA aqueous solution (15 wt%,1.0 mL) described above.

Experimental example 8: comparison of optical Properties according to the light scattering agent

The blue light reduction rate and Color Conversion Efficiency (CCE) were measured by using a blue LED having an emission wavelength of 450nm as excitation light and exciting each color conversion film with respect to the color conversion film of preparation example 4. The results are shown in table 8 below. The method for measuring the color conversion efficiency is described in experimental example 5, and the method for measuring the blue light reduction rate is specifically described with reference to fig. 6. In fig. 6, the blue light emitting region (a) refers to blue incident light absorbed by the color conversion film, and coincides with the blue light reduction rate.

TABLE 8

Fig. 8 is a graph showing the luminous intensity (Emission intensity) of the wavelengths of the color conversion films according to preparation examples 4-1 to 4, and fig. 9 is a graph showing the light intensity (Radiant power) of the wavelengths of the color conversion films according to preparation examples 4-1 to 4. As confirmed in table 8, fig. 8 and 9, the light scattering agent increases the light absorption efficiency by producing the light scattering effect, with the result that the color conversion efficiency is improved. Under the same conditions, the color conversion efficiency of preparation example 4-1 using TiO ₂ was improved by about 1.9 times as compared with preparation example 4-2 without using TiO ₂. And, the blue light reduction rate of preparation example 4-1 using TiO ₂ was improved by about 1.3 times as compared with preparation example 4-2 not using TiO ₂ under the same conditions.

Experimental example 9: comparing optical characteristics of the laminate according to the color conversion film

The blue light reduction rate and the color conversion efficiency were measured for the case (1L) in which 1 color conversion film was formed as a single layer and the case (2L) in which 2 color conversion films were laminated, with the color conversion film of preparation example 4 as an object. The results are shown in table 9 below. In table 9 below, 1L shows a case where 1 color conversion film is formed as a single layer, and 2L shows a case where 2 color conversion films are laminated.

TABLE 9

Fig. 10 is a graph showing absorbance of the color conversion films of preparation examples 4-4 to 4-6, fig. 11 is a graph showing light intensity of thin films prepared by laminating the color conversion films of preparation examples 4-4 to 4-6 in a single layer, and fig. 12 is a graph showing light intensity of thin films prepared by laminating the color conversion films of preparation examples 4-4 to 4-6 in 2 sheets. As can be seen from table 9, when the content of the organic nanoparticles was increased in a state where the content of the light scattering agent was fixed at 6.0%, the color conversion efficiency was increased, and when the laminate (2L) was formed, the color conversion efficiency was decreased as compared with the case where the laminate was formed as a single layer (1L). However, the reduction rate of blue light was better when the laminate (2L) was formed than when it was formed as a single layer (1L). Both the single layer (1L) and the laminate (2L) showed the most excellent blue light shielding effect at the content of the organic nanoparticles of 8.0%.

Experimental example 10: comparing the luminescence characteristic with the commercial color conversion film and the color conversion film characteristic

The color conversion films of preparation examples 4 to5 and commercial quantum dot films IS22E73001 (hybrid, reference example 1), IS22E131003 (hybrid, reference example 2) and IS22E273002 (InP, reference example 3) sold by InnoQD were measured for the light emission characteristics and the color conversion film characteristics. The results are shown in tables 10 and 11 below.

Table 10

TABLE 11

Fig. 13 is an absorbance chart showing the color conversion films of reference examples 1 to 3, fig. 14 is a photoluminescence intensity chart of the color conversion films of reference examples 1 to 3, fig. 15 is a light intensity chart of the color conversion films of reference examples 1 to 3, and fig. 16 is a light intensity chart of the color conversion films of preparation examples 4 to 5. As can be seen from tables 10 and 11, fig. 13 to 16, the color conversion film of the present invention can be formed with a very thin thickness as compared with a commercial film. In particular, in the case of a commercial film, the use of quantum dot materials is weak to oxygen and moisture, and thus a separator is applied, and as a result, there is a limit in reducing the thickness of the film.

As can be confirmed from tables 10 and 11, the color conversion film of the present invention was formed at a thin thickness, but still showed a high blue light shielding characteristic of 35%, and also showed a relatively high characteristic of red light emission intensity.

Also, as confirmed in table 11, the color conversion film prepared according to the present invention showed a full width at half maximum of red light and similar color conversion efficiency at a level similar to that of the commercial thin film reference example 3 formed of the quantum dot substance.

Experimental example 11: constant temperature and humidity characteristics compared to commercial color conversion films

To evaluate the constant temperature and humidity characteristics, the photoluminescence intensity was measured after 480 hours of exposure at 90% relative humidity (Relative Humidity, RH) at 60 ℃ and after 480 hours of exposure at 85% RH at 85 ℃. Fig. 17 and 18 show this. Specifically, fig. 17 is a graph showing the results of the constant temperature and humidity evaluation of the color conversion film of reference example 2, and fig. 18 is a graph showing the results of the constant temperature and humidity evaluation of the color conversion films of preparation examples 4 to 5.

As can be seen from fig. 17 and 18, the color conversion film of the present invention is formed with a very thin thickness, and shows constant temperature and humidity characteristics at the same or similar level as that of reference example 2 to which the separator is applied, even if the separator is not applied.

Experimental example 12: light resistance characteristics compared to commercial color conversion films

To evaluate the light resistance, after UV light additional exposure for 312 hours, the photoluminescence intensity was measured and the reduction was compared, except for 168 hours of UV light exposure.

Fig. 19 is a graph showing the light fastness evaluation results of the color conversion films of reference example 2, and fig. 20 is a graph showing the light fastness evaluation results of the color conversion films of preparation examples 4 to 5.

As can be seen from fig. 19 and 20, even if the color conversion film of the present invention is formed in a very thin thickness, it has good light resistance for 200 hours or more.

Preparation example 5: preparation of color conversion film (3)

< Preparation example 5-1>

After PVA and SA were mixed with deionized water at a weight ratio of 49:1, thereby preparing a 20 weight percent aqueous polyvinyl alcohol solution (PVA-SA, 20 wt%) and heated at a temperature of 80℃for 3 hours. tPhBODIPY organic nanoparticles (2.13 wt% dispersion, 0.10 mL) and TiO ₂ solution (15.0 wt% aqueous solution, 0.01 mL) of preparation examples 1-5 above were mixed with PVA-SA aqueous solution (20.0 wt%,0.51 mL) above. After spraying the mixed solution on a glass substrate, a thin film was formed by a bar coating method. To remove the solvent, the film was stored in an oven at 60 ℃ for 4 hours, and a crosslinking reaction was performed at a temperature of 120 ℃ for 2 hours, thereby preparing a color conversion film.

< Preparation example 5-2>

A color conversion film was produced in the same manner as in production example 5-1, except that 0.12mL of the organic nanoparticle and 0.017mL of the TiO ₂ solution were mixed with the PVA-SA aqueous solution (20.0 wt%,0.5 mL).

< Preparation example 5-3>

A color conversion film was produced in the same manner as in production example 5-1, except that 0.16mL of the organic nanoparticle and 0.033mL of the TiO ₂ solution were mixed with the PVA-SA aqueous solution (20.0 wt%,0.51 mL) described above.

< Preparation examples 5 to 4>

A color conversion film was produced in the same manner as in production example 5-1, except that 0.23mL of the organic nanoparticle and 0.04mL of the TiO ₂ solution were mixed with the PVA-SA aqueous solution (20.0 wt%,0.51 mL) described above.

< Preparation examples 5 to 5>

A color conversion film was produced in the same manner as in production example 5-1, except that 0.32mL of the organic nanoparticle and 0.05mL of the TiO ₂ solution were mixed with the PVA-SA aqueous solution (20.0 wt%,0.6 mL) described above.

Experimental example 13: comparing optical properties

The blue light reduction rate and the Color Conversion Efficiency (CCE) were measured for the color conversion film of preparation example 5. The results are shown in table 12 below.

Table 12

Fig. 21 is a graph showing absorbance of the color conversion films of preparation examples 5-1 to 5-4, fig. 22 is a graph showing light intensity of thin films prepared by laminating the color conversion films of preparation examples 5-1 to 5 in a single layer, and fig. 23 is a graph showing light intensity of thin films prepared by laminating the color conversion films of preparation examples 5-4 and 5-5 in 2 sheets.

Referring to table 12, in case of the green thin film, preparation example 5-1 using 2.0 weight percent of organic nanoparticles and 1.4 weight percent of TiO ₂ shows the highest color conversion efficiency (92%). Referring to preparation examples 5 to 4 and 5 to 5, as in the case of the red thin film, the color conversion efficiency was reduced in the case of using the bilayer, but the blue light reduction rate was increased to 78.6%. In the case of an OLED or micro LED using RGB trichromatic light, since the blue light itself is reduced more and less, it is preferable that the blue light remains 50% in the LCD using the blue LED, and the color conversion film of the present invention can be applied to various applications according to the need.

The foregoing description of the present specification is merely exemplary, and it will be understood by those skilled in the art to which the present specification pertains that other specific forms of modification may be readily adopted without altering the technical ideas or essential features described in the present specification. It is therefore to be understood that the above described embodiments are illustrative only and not limiting in all respects. For example, each component described as a single type may be implemented in a distributed manner, and similarly, components described as a distributed type may be implemented in a combined manner.

The scope of the present specification is indicated by the appended claims, and all changes or modifications that come within the meaning and range of equivalency of the claims are intended to be embraced therein.

Claims

1. A luminescent organic nanoparticle comprising an organic fluorescent material having a luminous efficiency of 80% or more,

The average particle diameter is 100nm to 170nm, and the standard deviation of the particle diameter is below 500 nm.

2. The luminescent organic nanoparticle as claimed in claim 1, wherein,

The core-shell structure has a morphology in which the organic fluorescent material is surrounded by a surfactant.

3. The luminescent organic nanoparticle as claimed in claim 1, wherein,

The organic phosphor is a delayed fluorescent material.

4. The luminescent organic nanoparticle as claimed in claim 3, wherein,

The delayed fluorescent material is a compound represented by the following chemical formula 1:

chemical formula 1:

In the above-mentioned chemical formula 1,

When L is a carbon-nitrogen single bond, D is a carbon atom-number 10 to 40 parallel ring comprising a conjugated or unconjugated five-or six-sided ring containing a nitrogen atom of the above L, wherein the conjugated or unconjugated five-or six-sided ring is a substituted or unsubstituted ring, comprising or not comprising a group 16 element as a ring-forming element, comprising 1 or 2 nitrogen atoms as a ring-forming element, a is a heterocyclic ring having a carbon atom number 10 to 40, comprising an aryl group containing a carbon atom bonded to the above L, wherein the above heterocyclic ring comprises a ring structure forming a parallel ring with an aryl group containing a carbon atom bonded to the above L, wherein the above ring structure is a ring structure containing a boron atom and an oxygen atom as ring-forming elements, or a five-or six-sided ring structure containing conjugated 2 nitrogen atoms.

5. The luminescent organic nanoparticle as claimed in claim 4, wherein,

The compound represented by the above chemical formula 1 is one or more selected from the group consisting of the following compounds T-1 to T-28:

6. The luminescent organic nanoparticle as claimed in claim 1, wherein,

The organic phosphor is a boron compound represented by the following chemical formula 2:

Chemical formula 2:

In the above-mentioned chemical formula 2,

N1 and n4 are each independently integers from 1 to 4,

N2, n3 and n5 are each independently integers from 1 to 3,

R ₁ to R ₅ and X ₁ to X ₄ may form a substituted or unsubstituted ring by bonding with adjacent substituents.

7. The luminescent organic nanoparticle as claimed in claim 6, wherein,

The boron compound represented by the above chemical formula 2 is one or more selected from the group consisting of the following compounds D-1 to D-30:

8. the luminescent organic nanoparticle as claimed in claim 1, wherein,

The organic phosphor is a boron compound represented by the following chemical formula 3:

Chemical formula 3:

in the above-mentioned chemical formula 3, a compound represented by formula 1,

C ₁ to C ₃ have a five-sided or six-sided ring structure respectively,

Y ₁ and Y ₂ are each independently fluorine or alkoxy,

A and b are each independently integers from 1 to 4,

R ₅₁ to R ₅₂ may form a substituted or unsubstituted ring by bonding with an adjacent substituent.

9. The luminescent organic nanoparticle as claimed in claim 8, wherein,

The boron compound represented by the above chemical formula 3 is one or more selected from the group consisting of the following compounds B-1 to B-33:

10. The luminescent organic nanoparticle as claimed in claim 2, wherein,

The surfactant is at least one selected from the group consisting of anionic surfactants, cationic surfactants, zwitterionic surfactants and nonionic surfactants.

11. A composition for a color conversion film, characterized in that,

Comprising the luminescent organic nanoparticle according to claim 1 and a water-soluble polymer resin.

12. The composition for a color conversion film according to claim 11,

The luminescent organic nanoparticle is contained in an amount of 1 to 20 parts by weight based on 100 parts by weight of the water-soluble polymer resin.

13. The composition for a color conversion film according to claim 11,

The water-soluble polymer resin further comprises 0.01 to 20 parts by weight of a crosslinking agent based on 100 parts by weight of the water-soluble polymer resin.

14. The composition for a color conversion film according to claim 11,

The light scattering agent is contained in an amount of 1 to 20 parts by weight based on 100 parts by weight of the water-soluble polymer resin.

15. The composition for a color conversion film according to claim 11,

The water-soluble polymer resin has a weight average molecular weight of 5000g/mol to 100000g/mol and a hydration degree of 70% to 100%, and is one or more polymers or copolymers selected from the group consisting of nonionic water-soluble polymers, anionic water-soluble polymers and cationic water-soluble polymers,

The nonionic polymer is at least one polymer or copolymer selected from the group consisting of polyvinyl alcohol, polyethylene oxide, polyacrylamide and polyvinylpyrrolidone,

The anionic water-soluble polymer is at least one polymer or copolymer selected from the group consisting of polyacrylic acid and its derivatives, polystyrene sulfonic acid, polysilicic acid, polyphosphoric acid, polyethylene sulfinic acid, poly [3- (ethyleneoxy) propane-1-sulfonic acid ], poly (4-vinylphenol), poly (4-vinylphenol sulfuric acid), poly (ethylenephosphoric acid), poly (maleic acid), poly (2-methyl ethylene oxide-1-sulfonic acid), poly (3-methacryloxypropane-1-sulfonic acid) and poly (4-vinylbenzoic acid),

The cationic water-soluble polymer is one or more polymers or copolymers selected from the group consisting of polyethyleneimine, polyamine, polyamidoamine, polydienyl dimethyl ammonium chloride, poly (4-vinylbenzyl trimethyl ammonium salt), poly [ (dimethylamino) trimethylene (dimethylimino) hexamethylene dibromo ], poly (2-vinylpiperidine salt), poly (vinylamine salt), poly (2-vinylpyridine) and derivatives thereof, and a composition for a color conversion film.

16. The composition for a color conversion film according to claim 13,

The crosslinking agent is at least one selected from glutaraldehyde, glyoxal, maleic acid, citric acid, sodium trimetaphosphate, sodium hexametaphosphate, dianhydride, succinic acid, suberic acid, sulfosuccinic acid and K ₂S₂O₈.

17. The composition for a color conversion film according to claim 14,

The light scattering agent is at least one kind of inorganic metal oxide particles selected from the group consisting of TiO ₂、ZnO、Fe₃O₄、CeO₂、MoO₂、Ag₂ O, cuO and NiO,

The average particle size of the inorganic metal oxide particles is 200nm to 400nm.

18. A color conversion film, characterized in that,

Prepared using the composition for color conversion film according to any one of claims 11 to 17.

19. A display device, which is characterized in that,

A color conversion film comprising the color conversion film of claim 18.

20. A light-emitting diode device is characterized in that,

A color conversion film comprising the color conversion film of claim 18.