TW201726885A - Color conversion composition, color conversion film, and light source unit, display and lighting system containing same - Google Patents

Abstract

A color conversion composition that is one aspect of the present invention contains component (A), component (B) and component (C), and converts incident light into light having a longer wavelength than the incident light. This color conversion composition and a color conversion film containing same can be used in a light source unit, a display and a lighting system. Component (A): at least one type of organic light-emitting material. Component (B): a binder resin. Component (C): an amine derivative having a partial structure represented by general formula (1) (R10 to R14 may be the same as, or different from, each other, and are selected from among hydrogen atoms, alkyl groups, cycloalkyl groups, aryl groups and heteroaryl groups. However, at least one of R11 and R12 and at least one of R13 and R14 are not hydrogen atoms).

Description

Color conversion composition, color conversion film, light source unit including the same, display and illumination device

The present invention relates to a color conversion composition, a color conversion film, a light source unit including the same, a display, and a lighting device.

It is actively being studied to apply a multi-coloring technique using a color conversion method to a liquid crystal display, an organic electroluminescence (EL) display, a lighting device, and the like. The color conversion means converting light from the illuminant into light having a longer wavelength, and for example, converting blue luminescence into green luminescence or red luminescence. A composition having the color conversion function (hereinafter referred to as a "color conversion composition") is formed into a film and combined with, for example, a blue light source, whereby blue, green, and red colors can be taken out from the blue light source. The primary color can be used to remove white light. A white light source in which a blue light source and a film having a color conversion function (hereinafter referred to as a "color conversion film") are combined is used as a backlight unit, and the backlight unit, the liquid crystal driving portion, and the color filter are applied. Combine to create a full color display. In addition, if there is no liquid crystal driving portion, it can be directly used as a white light source, for example, a white light source that can be used as a light emitting diode (LED) illumination or the like.

As a subject of a liquid crystal display using a color conversion method, improvement in color reproducibility can be cited. For improving color reproducibility, it is effective to reduce the half width of each of the blue, green, and red light-emitting spectra of the backlight unit, and to improve the color purity of each of the blue, green, and red colors.

As a method for solving this problem, a technique in which a quantum dot formed of inorganic semiconductor fine particles is used as a component of a color conversion composition has been proposed (for example, see Patent Document 1). The technique using quantum dots does have a narrow half-width of the green and red luminescence spectrum, and the color reproducibility is improved, but the quantum dots are not heat-resistant, moisture or oxygen in the air, and durability is not sufficient. In addition, there are also problems such as the inclusion of cadmium.

Further, a technique of using a luminescent material of an organic substance instead of a quantum dot as a component of a color conversion composition has also been proposed. As an example of a technique of using an organic light-emitting material as a component of a color conversion composition, those who use a coumarin derivative (for example, refer to Patent Document 2) and use a rhodamine derivative (for example, refer to Patent Document 3) A pyrromethylene derivative is used (for example, refer to Patent Document 4). In addition, a technique of adding a light stabilizer to prevent deterioration of the organic light-emitting material and to improve durability has been proposed (for example, refer to Patent Document 5). Prior art literature

Patent Document 1: Japanese Patent Laid-Open Publication No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. Patent Document 5: International Publication No. 2011/149028

[Problems to be Solved by the Invention] However, even if these organic light-emitting materials or light stabilizers are used, it is still insufficient from the viewpoint of coexistence of color reproducibility and durability.

For example, Patent Document 5 discloses a technique for improving durability by passivating singlet oxygen. However, a clear solution has not been made for deterioration factors other than singlet oxygen, and therefore, durability is not sufficient. Further, since the light stabilizer described in Patent Document 5 has relatively strong absorption in the visible region, it absorbs the light emission of the light-emitting material, so that there is a problem that the light-emitting efficiency is lowered.

Thus, the technique of using an organic light-emitting material having high color purity (increased color reproducibility) and high durability as a component of a color conversion composition is still insufficient.

The problem to be solved by the present invention is to enhance the color reproducibility and high durability in a color conversion composition used in a display device such as a liquid crystal display or an illumination device such as LED illumination, in particular, high-color purity illumination and high durability. Sexual coexistence. [Means for solving the problem]

The inventors have found that radicals generated by light irradiation cause deterioration of the organic light-emitting material. Moreover, it has been found that by using a specific substance as a component of the color conversion composition, the generated radical can be passivated and the durability of the organic light-emitting material can be improved.

In order to solve the above problems, and to achieve the object, the color conversion composition of the present invention is a color conversion composition that converts incident light into light having a longer wavelength than the incident light, and includes the following component (A). , (B) component and (C) component. (A) component: at least one organic light-emitting material (B) component: binder resin (C) component: an amine derivative having a partial structure represented by the general formula (1)

[Chemical 1] (R ¹⁰ to R ¹⁴ may be the same or different, and may be selected from a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a heteroaryl group. Among them, at least one of R ¹¹ and R ¹² and R ¹³ and At least one of R ¹⁴ is not a hydrogen atom)

Further, in the invention, the color conversion composition of the invention is characterized in that the component (C) is a compound having a piperidine skeleton represented by the formula (2).

[Chemical 2] (R ¹⁰ to R ¹⁴ are the same as the above formula (1))

Further, in the invention, the color conversion composition of the invention is characterized in that the component (C) is a compound represented by the formula (3).

[Chemical 3] (R ¹⁰ to R ¹⁴ are the same as those of the above formula (1). m is a natural number of 10 or less. Y is a single bond, a chain or a cyclic aliphatic hydrocarbon, an aliphatic heterocyclic ring, an aromatic hydrocarbon ring, or a fragrance. Family heterocycle, or a combination of these)

Further, in the invention, the color conversion composition of the present invention is characterized in that Y of the above formula (3) is a chain or cyclic aliphatic hydrocarbon, a benzene ring, or a combination thereof.

Further, in the invention, the color conversion composition of the invention is characterized in that the R ¹⁰ is an alkyl group.

Further, in the invention, the color conversion composition of the present invention is characterized in that the content of the component (C) is 1.0 × 10 ^-2 parts by weight or more based on 100 parts by weight of the component (B). 10 parts by weight or less.

Further, in the invention, the color conversion composition of the present invention is characterized in that the component (A) contains a compound represented by the formula (4).

[Chemical 4] (X is CR ⁷ or N. R ¹ to R ⁹ may be the same or different, and may be different from hydrogen, alkyl, cycloalkyl, heterocyclic, alkenyl, cycloalkenyl, alkynyl, hydroxy, thiol. , alkoxy, alkylthio, aryl ether, aryl sulfide, aryl, heteroaryl, halogen, cyano, aldehyde, carbonyl, carboxyl, oxycarbonyl, aminecaraki, amine, nitrate a group selected from the group consisting of a condensed ring and an aliphatic ring formed between a sulfonyl group, a decyloxy group, a boroxyl group, a phosphine oxide group, and an adjacent substituent)

Further, in the invention, the color conversion composition of the invention is characterized in that X of the formula (4) is CR ⁷ and the R ⁷ is a group represented by the formula (5).

[Chemical 5] (r is selected from hydrogen, alkyl, cycloalkyl, heterocyclic, alkenyl, cycloalkenyl, alkynyl, hydroxy, thiol, alkoxy, alkylthio, aryl ether, aryl sulfide , aryl, heteroaryl, halogen, cyano, aldehyde, carbonyl, carboxyl, oxycarbonyl, amine, mercapto, amine, nitro, decyl, decyl, boro, phosphine The group consisting of k is an integer from 1 to 3. When k is 2 or more, r may be the same or different.

Further, in the above invention, the color conversion composition of the present invention is characterized in that R ¹ , R ³ , R ⁴ and R ^{6 of} the above formula (4) are respectively the same, different, and substituted. Or unsubstituted phenyl.

Further, in the above invention, the color conversion composition of the present invention is characterized in that R ¹ , R ³ , R ⁴ and R ^{6 of} the above formula (4) are respectively the same, different, and substituted. Or unsubstituted alkyl.

Further, in the invention described above, the color conversion composition of the present invention is characterized in that the component (A) is contained at a peak wavelength of 500 by using excitation light having a wavelength of 430 nm or more and 500 nm or less. A luminescent material that is observed in a region above nm and below 580 nm.

Further, in the invention, the color conversion composition of the present invention is characterized in that the component (A) contains the following luminescent material (a) and luminescent material (b). Luminescent material (a): a luminescent material luminescent material which is observed in a region having a peak wavelength of 500 nm or more and 580 nm or less by using excitation light having a wavelength of 430 nm or more and 500 nm or less ( b): excitation is performed by at least one of excitation light having a wavelength of 430 nm or more and 500 nm or less and luminescence from the luminescent material (a), thereby exhibiting a peak wavelength of 580 nm or more and 750 nm. Luminescent luminescent materials observed in the following regions

Further, in the invention, the color conversion composition of the present invention is characterized in that the content w _a of the luminescent material (a) and the content w _b of the luminescent material (b) are w _a ≧ w _b .

Further, in the above invention, the color conversion composition of the present invention is characterized in that the excitation light having a wavelength of 430 nm or more and 500 nm or less is used to emit light having a peak wavelength of 500 nm or more and 580 nm or less. The luminescent material is a compound represented by the above formula (4).

Further, in the invention, the color conversion composition of the invention is characterized in that the luminescent material (b) is a compound represented by the above formula (4).

Further, the color conversion film of the present invention is characterized by comprising a cured layer of the color conversion composition described in any one of the inventions.

Further, the light source unit of the present invention is characterized by comprising a light source and the color conversion film described in the invention.

Further, in the above invention, the light source unit of the present invention is characterized in that the light source is a light-emitting diode having maximum light emission in a wavelength range of 430 nm or more and 500 nm or less.

Further, the display of the present invention is characterized by comprising the light source unit described in any one of the inventions.

Further, the illumination device of the present invention is characterized by comprising the light source unit described in any one of the inventions. [Effects of the Invention]

In the color conversion composition of the present invention and the color conversion film using the same, high-color purity luminescence and high durability are coexistence, so that the effect of improving color reproducibility and high durability can be obtained. Since the light source unit, the display, and the illumination device of the present invention use such a color conversion film, it is possible to achieve an effect of improving color reproducibility and high durability.

Hereinafter, a preferred embodiment of the color conversion composition, the color conversion film, the light source unit including the same, the display, and the illumination device of the present invention will be specifically described. However, the present invention is not limited to the following embodiments and may correspond to the purpose or It is implemented after various changes have been made for use.

<Color conversion composition> The color conversion composition according to the embodiment of the present invention converts incident light from a light source such as a light source into light having a longer wavelength than the incident light, and contains at least (A) component and (B) component. And (C) ingredients. In the present invention, the component (A) is at least one organic light-emitting material. The component (B) is a binder resin. The component (C) is an amine derivative having a partial structure represented by the formula (1) in a molecular structure.

[Chemical 6]

In the formula (1), R ¹⁰ to R ¹⁴ are each selected from a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group and a heteroaryl group. The R ¹⁰ to R ¹⁴ may be the same or different. Further, at least one of R ¹¹ and R ¹² and at least one of R ¹³ and R ¹⁴ are not a hydrogen atom.

<(A) component: organic light-emitting material> The color conversion composition of the embodiment of the present invention contains at least one organic light-emitting material as the component (A). Here, the luminescent material in the present invention means a material that emits light having a wavelength different from the light when a certain kind of light is irradiated. The organic light-emitting material is an organic light-emitting material.

In order to achieve high-efficiency color conversion, the luminescent material is preferably a material exhibiting luminescent properties with high luminescence quantum yield. In general, a known luminescent material such as an inorganic phosphor, a fluorescent pigment, a fluorescent dye, or a quantum dot is used as the luminescent material, but in terms of uniformity of dispersion, reduction in use amount, and reduction in environmental load, It is preferably an organic light-emitting material.

Examples of the organic light-emitting material include the following. For example, a compound having a condensed aryl ring such as naphthalene, anthracene, phenanthrene, anthracene, anthracene, fused tetraphenyl, triphenylene, fluorene, fluoranthene, anthracene or anthracene, or a derivative thereof may be mentioned as a suitable organic light-emitting material. Further, there may be mentioned furan, pyrrole, thiophene, thiophene, 9-fluorene, 9,9'-spirobifluorene, benzothiophene, benzofuran, anthracene, dibenzothiophene, dibenzofuran, imidazole And a compound having a heteroaryl ring such as pyridine, phenanthroline, pyridine, pyrazine, naphthyridine, quinoxaline or pyrrolopyridine or a derivative thereof, a borane derivative or the like is suitable as a suitable organic light-emitting material.

Further, examples thereof include 1,4-distyrylbenzene, 4,4'-bis(2-(4-diphenylaminophenyl)vinyl)biphenyl, and 4,4'-bis(N-( a stilbene derivative such as stilbene-4-yl)-N-phenylamino)stilbene, an aromatic acetylene derivative, a tetraphenylbutadiene derivative, an aldehyde nitrogen derivative, pyrrole A base derivative, a diketopyrrolo[3,4-c]pyrrole derivative or the like is suitable as a suitable organic light-emitting material. Further, examples thereof include coumarin derivatives such as coumarin 6, coumarin 7, and coumarin 153, and azole derivatives such as imidazole, thiazole, thiadiazole, oxazole, oxazole, oxadiazole, and triazole. A metal complex, a cyanine compound such as phthalocyanine, a xanthene compound such as fluorescein, eosin, or rhodamine, or a thioxan compound is used as a suitable organic light-emitting material.

Further, examples thereof include a polyphenylene compound, a naphthylimine derivative, a phthalocyanine derivative and a metal complex thereof, a porphyrin derivative and a metal complex thereof, Nile Red or Nile Blue, and the like. Oxazine-based compound, spiroene compound, N,N'-diphenyl-N,N'-bis(3-methylphenyl)-4,4'-diphenyl-1,1'-diamine An aromatic amine derivative or the like is used as a suitable organic light-emitting material. Further, as the suitable organic light-emitting, an organometallic compound such as iridium (Ir), ruthenium (Ru), rhodium (Rh), palladium (Pd), platinum (Pt), osmium (Os) or ruthenium (Re) may be mentioned. material. However, the organic light-emitting material in the present invention is not limited to the organic light-emitting material described above.

The organic light-emitting material may be a fluorescent material or a phosphorescent material, but in order to achieve high color purity, a fluorescent material is preferred. Among these, in terms of high thermal stability and high photostability, a compound having a condensed aryl ring or a derivative thereof is preferred.

Further, as the organic light-emitting material, a compound having a coordinate bond is preferred from the viewpoint of solubility or molecular structure diversity. From the viewpoint of having a small half width and efficient light emission, a boron-containing compound such as a boron fluoride complex is also preferable. Among them, a pyrrolethymethylene derivative is preferred from the viewpoint of providing high luminescence quantum yield and good durability. More preferably, it is a compound represented by the formula (4), that is, a pyrrolemethylene compound.

[Chemistry 7]

When the component (A) contains a compound represented by the formula (4) as an organic light-emitting material, in the formula (4), X is CR ⁷ or N. R ¹ to R ⁹ may be the same or different, and may be different from hydrogen, alkyl, cycloalkyl, heterocyclic, alkenyl, cycloalkenyl, alkynyl, hydroxy, thiol, alkoxy, alkylthio. , aryl ether group, aryl sulfide group, aryl group, heteroaryl group, halogen, cyano group, aldehyde group, carbonyl group, carboxyl group, oxycarbonyl group, amine methyl group, amine group, nitro group, decyl group, decane oxide The group is selected from the group consisting of a condensed ring and an aliphatic ring formed between a oxyboron group, a phosphine oxide group, and an adjacent substituent.

Hydrogen may also be ruthenium in all of the groups. The same is true for the compounds described below or their partial structures. In the following description, for example, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms means that all carbon numbers including the carbon number contained in the substituent substituted with the aryl group become 6 to 40 aryl groups. The same is true for other substituents that specify the carbon number.

Further, among all the groups, as the substituent at the time of substitution, an alkyl group, a cycloalkyl group, a heterocyclic group, an alkenyl group, a cycloalkenyl group, an alkynyl group, a hydroxyl group, a thiol group or an alkoxy group is preferred. , alkylthio, aryl ether, aryl sulfide, aryl, heteroaryl, halogen, cyano, aldehyde, carbonyl, carboxyl, oxycarbonyl, aminecarboxamidine, amine, nitro, decyl More preferably, it is a preferred substituent in the description of each substituent. Further, the substituents may be further substituted by the substituent.

"Unsubstituted" in the case of "substituted or unsubstituted" means substituted with a hydrogen atom or a halogen atom. In the case of the compound described below or a partial structure thereof, the case of "substituted or unsubstituted" is also the same as described above.

Among all the groups, the alkyl group, for example, represents a saturated aliphatic hydrocarbon group such as methyl, ethyl, n-propyl, isopropyl, n-butyl, t-butyl or t-butyl, which may have The substituent may or may not have a substituent. The additional substituent at the time of substitution is not particularly limited, and examples thereof include an alkyl group, a halogen group, an aryl group, and a heteroaryl group, which are also used in the following description. In addition, the number of carbon atoms of the alkyl group is not particularly limited, but from the viewpoint of availability and cost, it is preferably 1 or more and 20 or less, more preferably 1 or more and 8 or less.

The cycloalkyl group means, for example, a saturated alicyclic hydrocarbon group such as a cyclopropyl group, a cyclohexyl group, a norbornyl group or an adamantyl group, and may or may not have a substituent. The carbon number of the alkyl moiety is not particularly limited, but is preferably in the range of 3 or more and 20 or less.

The heterocyclic group is, for example, an aliphatic ring having an atom other than carbon in the ring such as a pyran ring, a piperidine ring or a cyclic decylamine, and may have a substituent or may have no substituent. The carbon number of the heterocyclic group is not particularly limited, but is preferably in the range of 2 or more and 20 or less.

The alkenyl group may, for example, represent a double bond-containing unsaturated aliphatic hydrocarbon group such as a vinyl group, an allyl group or a butadienyl group, and may have a substituent or may have no substituent. The carbon number of the alkenyl group is not particularly limited, but is preferably in the range of 2 or more and 20 or less.

The cycloalkenyl group may, for example, represent a double bond-containing unsaturated alicyclic hydrocarbon group such as a cyclopentenyl group, a cyclopentadienyl group or a cyclohexenyl group, and may have a substituent or may have no substituent.

The alkynyl group is, for example, an unsaturated aliphatic hydrocarbon group having a triple bond such as an ethynyl group, and may have a substituent or may have no substituent. The carbon number of the alkynyl group is not particularly limited, but is preferably in the range of 2 or more and 20 or less.

The alkoxy group may, for example, represent a functional group in which an aliphatic hydrocarbon group is bonded via an ether bond such as a methoxy group, an ethoxy group or a propoxy group, and the aliphatic hydrocarbon group may have a substituent or may have no substituent. The carbon number of the alkoxy group is not particularly limited, but is preferably in the range of 1 or more and 20 or less.

The alkylthio group means that the oxygen atom of the ether bond of the alkoxy group is substituted by a sulfur atom. The alkylthio group may have a substituent or may have no substituent. The carbon number of the alkylthio group is not particularly limited, but is preferably in the range of 1 or more and 20 or less.

The aryl ether group is, for example, a functional group in which an aromatic hydrocarbon group is bonded via an ether bond such as a phenoxy group, and the aromatic hydrocarbon group may have a substituent or may have no substituent. The carbon number of the aryl ether group is not particularly limited, but is preferably in the range of 6 or more and 40 or less.

The aryl sulfide group refers to an oxygen atom of an ether bond of an aryl ether group which is substituted by a sulfur atom. The aromatic hydrocarbon group in the aryl sulfide group may have a substituent or may have no substituent. The carbon number of the aryl sulfide group is not particularly limited, but is preferably in the range of 6 or more and 40 or less.

The aryl group means, for example, a phenyl group, a biphenyl group, a triphenylene group, a naphthyl group, an anthracenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthryl group, a fluorenyl group, a benzophenanyl group, a benzindenyl group. An aromatic hydrocarbon group such as an anthracenyl group, a fluorenyl group, a propyl [di] olefin group, a triphenylene group, a benzopropane [di] ene fluorenyl group, a dibenzofluorenyl group, a fluorenyl group or a spiroalkenyl group. Among them, a phenyl group, a biphenyl group, a biphenylene group, a naphthyl group, an anthracenyl group, a phenanthryl group, an anthracenyl group, a fluorenyl group, a propyl [di] ene fluorenyl group, and a triphenylene group are preferable. The aryl group may have a substituent or may have no substituent. The carbon number of the aryl group is not particularly limited, but is preferably 6 or more and 40 or less, more preferably 6 or more and 30 or less.

When R ¹ to R ⁹ are a substituted or unsubstituted aryl group, as the aryl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a fluorenyl group, and the like are preferable. Preferred is phenyl, biphenyl, terphenyl, naphthyl. Further, it is more preferably a phenyl group, a biphenyl group or a terphenyl group, and particularly preferably a phenyl group.

When each substituent is further substituted by an aryl group, as the aryl group, a phenyl group, a biphenyl group, a triphenylene group, a naphthyl group, an anthracenyl group, a phenanthryl group, a fluorenyl group, and more preferably a phenyl group or a biphenyl group is preferred. Base, triphenyl, naphthyl. Particularly preferred is phenyl.

By heteroaryl, for example, pyridyl, furyl, thienyl, quinolyl, isoquinolinyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, naphthyridinyl, porphyrinyl, pyridazine , quinoxaline, quinazolinyl, benzofuranyl, benzothienyl, fluorenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, benzoxazolyl, porphyrin Base, carbazolyl, benzofuranoxazolyl, benzothienooxazolyl, indanoxazolyl, benzoquinolyl, acridinyl, dibenzoacridinyl, benzene And a cyclic aromatic group having one or more atoms other than carbon in the ring, such as an imidazolyl group, an imidazopyridyl group, a benzoxazolyl group, a benzothiazolyl group, or a morpholino group. Wherein, the naphthyridinyl group means 1,5-naphthyridinyl, 1,6-naphthyridinyl, 1,7-naphthyridinyl, 1,8-naphthyridinyl, 2,6-naphthyridinyl, 2, Any of 7-naphthyridinyl. The heteroaryl group may have a substituent or may have no substituent. The carbon number of the heteroaryl group is not particularly limited, but is preferably 2 or more and 40 or less, and more preferably 2 or more and 30 or less.

When R ¹ to R ⁹ are a substituted or unsubstituted heteroaryl group, as the heteroaryl group, a pyridyl group, a furyl group, a thienyl group, a quinolyl group, a pyrimidinyl group, a triazinyl group or a benzofuran is preferred. , benzothienyl, fluorenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, benzimidazolyl, imidazopyridyl, benzoxazolyl, benzothiazolyl, phenanthroline More preferably, it is a pyridyl group, a furyl group, a thienyl group, or a quinolyl group. Particularly preferred is a pyridyl group.

When each substituent is further substituted by a heteroaryl group, as the heteroaryl group, a pyridyl group, a furyl group, a thienyl group, a quinolyl group, a pyrimidinyl group, a triazinyl group, a benzofuranyl group, a benzothienyl group, Mercapto, dibenzofuranyl, dibenzothiophenyl, carbazolyl, benzimidazolyl, imidazopyridyl, benzoxazolyl, benzothiazolyl, morpholinyl, more preferably pyridyl , furyl, thienyl, quinolyl. Particularly preferred is a pyridyl group.

The halogen means an atom selected from the group consisting of fluorine, chlorine, bromine and iodine. Further, the carbonyl group, the carboxyl group, the oxycarbonyl group or the aminecarbamyl group may have a substituent or may have no substituent. Here, examples of the substituent include an alkyl group, a cycloalkyl group, an aryl group, and a heteroaryl group, and these substituents may be further substituted.

By amine group is meant a substituted or unsubstituted amine group. The amine group may have a substituent or may have no substituent, and examples of the substituent at the time of substitution include an aryl group, a heteroaryl group, a linear alkyl group, and a branched alkyl group. The aryl group and the heteroaryl group are preferably a phenyl group, a naphthyl group, a pyridyl group or a quinolyl group. These substituents may be further substituted. The number of carbon atoms is not particularly limited, but is preferably 2 or more and 50 or less, more preferably 6 or more and 40 or less, and particularly preferably 6 or more and 30 or less.

The alkylene group, for example, represents an alkylalkyl group such as a trimethylsulfanyl group, a triethylsulfanyl group, a tert-butyldimethylsilyl group, a propyldimethylmethylalkyl group or a vinyldimethylalkylene group, or An arylalkylalkyl group such as phenyldimethylmethylalkyl, tert-butyldiphenylalkyl, triphenylsulfanyl or trinaphthylalkyl. The substituent on the oxime can be further substituted. The carbon number of the decyl group is not particularly limited, but is preferably in the range of 1 or more and 30 or less.

The oxime group is, for example, a fluorene compound group via an ether bond such as a trimethylphosphonium group. The substituent on the oxime can be further substituted. Further, the term "oxyboron group" means a substituted or unsubstituted oxygen boron group. The oxyboron group may have a substituent or may have no substituent, and examples of the substituent at the time of substitution include an aryl group, a heteroaryl group, a linear alkyl group, a branched alkyl group, an aryl ether group, and an alkoxy group. Hydroxyl and the like. Among them, an aryl group or an aryl ether group is preferred. Further, the phosphine oxide group means a group represented by -P(=O)R ¹⁰ R ¹¹ . R ¹⁰ R ^{11 is selected} from the same group as R ¹ to R ⁹ .

The condensed ring and the aliphatic ring formed between the adjacent substituents mean that any two adjacent substituents (for example, R ¹ and R ^{2 of the} general formula (4) are bonded to each other to form a conjugate or a non- Conjugated circular skeleton. The constituent elements of such a condensed ring and an aliphatic ring may contain, in addition to carbon, an element selected from the group consisting of nitrogen, oxygen, sulfur, phosphorus, and antimony. Further, the condensed rings and the aliphatic ring may be further condensed with other rings.

The compound represented by the formula (4) exhibits a high luminescence quantum yield and a small half width of the luminescence spectrum, so that both high-efficiency color conversion and high color purity can be achieved. Further, the compound represented by the formula (4) can be adjusted to various properties or physical properties such as luminous efficiency, color purity, thermal stability, photostability, and dispersibility by introducing an appropriate substituent into an appropriate position. For example, at least one of R ¹ , R ³ , R ⁴ and R ⁶ is a substituted or unsubstituted alkyl group or substituted as compared with the case where R ¹ , R ³ , R ⁴ and R ⁶ are both hydrogen. The case of an unsubstituted aryl group, a substituted or unsubstituted heteroaryl group shows better thermal stability and light stability.

When at least one of R ¹ , R ³ , R ⁴ and R ⁶ is a substituted or unsubstituted alkyl group, as the alkyl group, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, and a positive group are preferable. An alkyl group having 1 to 6 carbon atoms such as a butyl group, a second butyl group, a tert-butyl group, a pentyl group or a hexyl group. Further, the alkyl group is preferably a methyl group, an ethyl group, a n-propyl group, an isopropyl group, an n-butyl group, a second butyl group or a third butyl group from the viewpoint of excellent thermal stability. Further, from the viewpoint of preventing concentration quenching and improving luminescence quantum yield, the alkyl group is more preferably a tributyl group having a large steric bulk. Further, from the viewpoint of easiness of synthesis and easiness of obtaining raw materials, a methyl group can be preferably used as the alkyl group.

When at least one of R ¹ , R ³ , R ⁴ and R ⁶ is a substituted or unsubstituted aryl group, as the aryl group, a phenyl group, a biphenyl group, a triphenylene group, a naphthyl group is preferable. More preferably, it is a phenyl group or a biphenyl group. Particularly preferred is phenyl.

When at least one of R ¹ , R ³ , R ⁴ and R ⁶ is a substituted or unsubstituted heteroaryl group, the heteroaryl group is preferably a pyridyl group, a quinolyl group or a thienyl group, more preferably Pyridyl, quinolyl. Particularly preferred is a pyridyl group.

When R ¹ , R ³ , R ⁴ and R ⁶ are each the same or different and are substituted or unsubstituted alkyl groups, the solubility in the binder resin or the solvent is good, which is preferable. In this case, the alkyl group is preferably a methyl group from the viewpoint of easiness of synthesis and easiness of obtaining a raw material.

When R ¹ , R ³ , R ⁴ and R ⁶ are each the same or different, and are substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl, they show better. Thermal stability and light stability are preferred. In this case, it is more preferred that each of R ¹ , R ³ , R ⁴ and R ⁶ may be the same or different and is a substituted or unsubstituted aryl group.

There are also substituents that enhance a variety of properties, but the substituents that exhibit sufficient performance in all properties are limited. In particular, it is difficult to coexist with high luminous efficiency and high color purity. Therefore, by introducing a plurality of substituents to the compound represented by the formula (4), a compound having a balance between luminescent properties and color purity can be obtained.

In particular, when R ¹ , R ³ , R ⁴ and R ⁶ are each the same or different and are substituted or unsubstituted aryl groups, it is preferably, for example, R ¹ ≠R ⁴ , R ³ ≠ A variety of substituents are introduced as in R ⁶ , R ¹ ≠R ³ or R ⁴ ≠R ⁶ . Here, "≠" indicates the basis of a different structure. For example, R ¹ ≠R ⁴ represents a group in which R ¹ and R ⁴ are different structures. By introducing a plurality of substituents as described above, an aryl group which affects the color purity and an aryl group which affects the light-emitting efficiency can be simultaneously introduced, and thus fine adjustment can be performed.

Among them, R ¹ ≠R ³ or R ⁴ ≠R ^{6 is} preferable from the viewpoint of improving the luminous efficiency and the color purity in a well-balanced manner. In this case, for the compound represented by the formula (4), one or more aryl groups which affect the color purity can be introduced into the pyrrole ring on both sides, and the luminescent group can be introduced at a position other than the aryl group. The efficiency affects the aryl group, thus maximizing the two properties. Further, when R ¹ ≠R ³ or R ⁴ ≠R ⁶ , from the viewpoint of improving both heat resistance and color purity, R ¹ = R ⁴ and R ³ = R ^{6 are more} preferable.

As the aryl group which mainly affects the color purity, an aryl group substituted with an electron-donating group is preferred. The electron donating group, in organic electron theory, refers to an atomic group that supplies electrons to a substituted atomic group by an inductive effect or a resonance effect. As the electron-donating group, a negative value is used as a substituent constant (σp (para)) of the Hammett equation. The substituent constant (σp (para)) of the Hammett equation can be quoted from the Chemical Review Basics Revision 5 (page II-380).

Specific examples of the electron-donating group include an alkyl group (σp: -0.17 of methyl group) or an alkoxy group (σp: -0.27 of methoxy group), and an amine group (σp: -0.66 of -NH ₂ ) )Wait. In particular, an alkyl group having 1 to 8 carbon atoms or an alkoxy group having 1 to 8 carbon atoms is preferred, and a methyl group, an ethyl group, a third butyl group or a methoxy group is more preferred. From the viewpoint of dispersibility, it is particularly preferably a tert-butyl group or a methoxy group, and when these groups are used as the electron-donating group, in the compound represented by the formula (4), it is possible to prevent Quenching caused by the agglomeration of molecules with each other. The substitution position of the substituent is not particularly limited, but in order to improve the photostability of the compound represented by the general formula (4), it is necessary to suppress the distortion of the bond, and therefore it is preferably bonded to the pyrroxyl skeleton. Position and bond to the meta or alignment. On the other hand, as the aryl group which mainly affects the luminous efficiency, an aryl group having a bulky substituent such as a third butyl group, an adamantyl group or a methoxy group is preferable.

When R ¹ , R ³ , R ⁴ and R ⁶ are respectively the same or different and are substituted or unsubstituted aryl groups, preferably R ¹ , R ³ , R ⁴ and R ⁶ are respectively the same. It may also be different and is a substituted or unsubstituted phenyl group. In this case, R ¹ , R ³ , R ⁴ and R ^{6 are more} preferably selected from the following Ar-1 to Ar-6. In this case, as a preferable combination of R ¹ , R ³ , R ⁴ and R ⁶ , the combination shown in Table 1-1 to Table 1-11 can be mentioned, but it is not limited to these combinations.

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[Table 1-1]

[Table 1-2]

[Table 1-3]

[Table 1-4]

[Table 1-5]

[Table 1-6]

[Table 1-7]

[Table 1-8]

[Table 1-9]

[Table 1-10]

[Table 1-11]

R ² and R ^{5 are} preferably any of hydrogen, an alkyl group, a carbonyl group, an oxycarbonyl group, and an aryl group. Among them, from the viewpoint of thermal stability, hydrogen or an alkyl group is preferred, and hydrogen is more preferable from the viewpoint of easily obtaining a narrow half width in the luminescence spectrum.

R ⁸ and R ^{9 are} preferably an alkyl group, an aryl group, a heteroaryl group, a fluorine, a fluorine-containing alkyl group, a fluorine-containing heteroaryl group or a fluorine-containing aryl group. In particular, R ⁸ and R ^{9 are more} preferably fluorine or a fluorine-containing aryl group for the stabilization of the excitation light and obtaining a higher luminescence quantum yield. Further, in terms of easiness of synthesis, R ⁸ and R ^{9 are more} preferably fluorine.

Here, the fluorine-containing aryl group means a fluorine-containing aryl group, and examples thereof include a fluorophenyl group, a trifluoromethylphenyl group, and a pentafluorophenyl group. The fluorine-containing heteroaryl group means a fluorine-containing heteroaryl group, and examples thereof include a fluoropyridyl group, a trifluoromethylpyridyl group, and a trifluoropyridyl group. The fluorine-containing alkyl group means a fluorine-containing alkyl group, and examples thereof include a trifluoromethyl group and a pentafluoroethyl group.

Further, in the general formula (4), X is preferably CR ⁷ from the viewpoint of photostability. When X is CR ⁷ , the substituent R ⁷ has a large influence on the durability of the compound represented by the general formula (4), that is, the decrease in the luminous intensity of the compound over time. Specifically, when R ⁷ is hydrogen, the reactivity of the site is high, and thus the site is easily reacted with moisture or oxygen in the air. This reaction causes decomposition of the compound represented by the general formula (4). Further, when R ^{7 is,} for example, a substituent having a large degree of freedom in the movement of a molecular chain such as an alkyl group, the reactivity does decrease, but in the composition, the compounds are agglomerated with each other over time, resulting in concentration quenching. The decline in luminous intensity. Therefore, R ^{7 is} preferably a group which is rigid and has a small degree of freedom of movement and is hard to cause aggregation. Specifically, a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group is preferred. Any of them.

In view of providing a higher luminescence quantum yield and more difficult to thermally decompose, in addition, from the viewpoint of photostability, X is preferably CR ⁷ and R ⁷ is a substituted or unsubstituted aryl group. The aryl group is preferably a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group or a fluorenyl group from the viewpoint of not impairing the emission wavelength.

Further, in order to improve the photostability of the compound represented by the general formula (4), it is necessary to appropriately suppress the distortion of the carbon-carbon bond between R ⁷ and the pyrrolethymethylene skeleton. This is because if the distortion is too large, the reactivity with respect to the excitation light becomes high, and the light stability is lowered. In this regard, as R ⁷ , a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted biphenyl group, a substituted or not The substituted naphthyl group is more preferably a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted biphenyl group. Particularly preferred are substituted or unsubstituted phenyl groups.

Further, R ^{7 is} preferably a substituent having a moderately large volume. By having a certain volume of R ⁷ , the aggregation of molecules can be prevented. As a result, the luminous efficiency or durability of the compound represented by the general formula (4) is further improved.

A more preferable example of such a bulky substituent is a structure of R ⁷ represented by the following formula (5).

[Chemistry 9]

In the formula (5), r is selected from hydrogen, alkyl, cycloalkyl, heterocyclic, alkenyl, cycloalkenyl, alkynyl, hydroxy, thiol, alkoxy, alkylthio, aryl ether , aryl sulfide group, aryl group, heteroaryl group, halogen, cyano group, aldehyde group, carbonyl group, carboxyl group, oxycarbonyl group, amine methyl group, amine group, nitro group, decyl group, decyloxy group, boron boron a group consisting of a phosphine oxide group. k is an integer of 1-3. When k is 2 or more, r may be the same or different.

From the standpoint of providing a higher luminescence quantum yield, r is preferably a substituted or unsubstituted aryl group. Among the aryl groups, a phenyl group and a naphthyl group are particularly preferable. When r is an aryl group, k of the formula (5) is preferably 1 or 2, and more preferably 2 from the viewpoint of further preventing aggregation of molecules. Further, when k is 2 or more, at least one of r is preferably substituted with an alkyl group. The alkyl group in this case is a particularly preferable example from the viewpoint of thermal stability, and a methyl group, an ethyl group, and a third butyl group.

Further, in terms of controlling the fluorescence wavelength or absorption wavelength, or improving compatibility with a solvent, r is preferably a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group or Halogen is more preferably methyl, ethyl, tert-butyl or methoxy. From the viewpoint of dispersibility, it is particularly preferably a tributyl group or a methoxy group. The fact that r is a third butyl group or a methoxy group is more effective for preventing quenching caused by aggregation of molecules with each other.

Further, as another aspect of the compound represented by the formula (4), at least one of R ¹ to R ⁷ is preferably an electron-withdrawing group. In particular, it is preferred that at least one of (1) R ¹ to R ⁶ is a pull electron group, (2) R ⁷ is a pull electron group, or (3) at least one of R ¹ to R ⁶ is a pull electron. And R ⁷ is a pull electron group. By introducing an electron withdrawing group onto the pyrromethene skeleton of the compound as described above, the electron density of the pyrrolebenzyl skeleton can be drastically reduced. Thereby, the stability of the compound to oxygen is further improved, and as a result, the durability of the compound can be further improved.

The so-called electron-donating group, also called electron accepting group, refers to an atomic group that attracts electrons from a substituted atomic group by an inductive effect or a resonance effect. As the electron withdrawing group, a positive value is used as a substituent constant (σp (para)) of the Hammett equation. The substituent constant (σp (para)) of the Hammett equation can be quoted from the Chemical Review Basics Revision 5 (page II-380). Further, the phenyl group also has an example in which a positive value as described above is employed, but in the present invention, the electron-withdrawing group does not contain a phenyl group.

Examples of the electron withdrawing group include -F(σp:+0.20), -Cl(σp:+0.28), -Br(σp:+0.30), and -I(σp:+0.30). , -CO ₂ R ¹² (σp: R = ¹² when the ethyl group is +0.45), -CONH ₂ (σp: +0.38), -COR ¹² (σp: +129 when the R ¹² is methyl), -CF ₃ (σp: +0.51), -SO ₂ R ¹² (σp: +129 when R ¹² is a methyl group), -NO ₂ (σp: +0.81), or the like. R ¹² each independently represents a hydrogen atom, a substituted or unsubstituted ring to form an aromatic hydrocarbon group having 6 to 30 carbon atoms, a substituted or unsubstituted ring to form a heterocyclic group having 5 to 30 atoms, substituted or Unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl group having 1 to 30 carbon atoms. Specific examples of the respective groups include the same examples as described above.

Preferred examples of the electron withdrawing group include fluorine, fluorine-containing aryl group, fluorine-containing heteroaryl group, fluorine-containing alkyl group, substituted or unsubstituted fluorenyl group, substituted or unsubstituted ester group, and Substituted or unsubstituted guanidino, substituted or unsubstituted sulfonyl or cyano. The reason is that the groups are difficult to chemically decompose.

As a more preferred electron withdrawing group, a fluorine-containing alkyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted ester group or a cyano group can be cited. The reason for this is that the groups are related to the effect of preventing concentration quenching and increasing the quantum yield of luminescence. Particularly preferred electron withdrawing groups are substituted or unsubstituted ester groups.

As one of the particularly preferable examples of the compound represented by the formula (4), R ¹ , R ³ , R ⁴ and R ⁶ may be the same or different, and may be substituted or unsubstituted. The alkyl group, and further, X is CR ⁷ and R ⁷ is a group represented by the formula (5). In this case, R ^{7 is} particularly preferably a group represented by the formula (5) containing r as a substituted or unsubstituted phenyl group.

Further, as another example of a particularly preferable example of the compound represented by the formula (4), R ¹ , R ³ , R ⁴ and R ⁶ may be the same or different, and from the Ar It is selected from -1 to Ar-6, and further, X is CR ⁷ and R ⁷ is a group represented by the formula (5). In this case, R ^{7 is more} preferably a group represented by the formula (5) containing r as a tributyl group or a methoxy group, and particularly preferably a formula (5) containing r as a methoxy group. The base of the representation.

An example of the compound represented by the formula (4) is shown below, but the compound is not limited to these examples.

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[Chemistry 20]

[Chem. 21]

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The compound represented by the formula (4) can be synthesized, for example, by the method described in JP-A-H08-509471 or JP-A-2000-208262. That is, by reacting a pyrrolemethylene compound and a metal salt in the presence of a base, a target pyrrolethymethylene metal complex can be obtained.

In addition, regarding the synthesis of pyrrolethymethylene-boron fluoride complex, reference may be made to "J. Org. Chem.", vol. 64, No. 21, pp. 7813-7819 (1999), The method described in "Angew. Chem., Int. Ed. Engl.", vol. 36, pp. 1333-1335 (1997), etc., synthesized by the formula (4) The compound represented. For example, a method in which a compound represented by the following formula (6) and a compound represented by the formula (7) are carried out in 1,2-dichloroethane in the presence of phosphorus oxychloride After heating, a compound represented by the following formula (8) is reacted in 1,2-dichloroethane in the presence of triethylamine, whereby a compound represented by the formula (4) is obtained. . However, the present invention is not limited to this. Here, R ¹ to R ⁹ are the same as described above. J represents halogen.

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Further, a method of forming a carbon-carbon bond by a coupling reaction of a halogenated derivative with a boronic acid or a boronic acid ester derivative when introducing an aryl group or a heteroaryl group is exemplified, but the present invention is not limited thereto. Similarly, a method of forming a carbon-carbon bond by coupling a halogenated derivative under a metal catalyst such as palladium with an amine or a carbazole derivative, when introducing an amine group or a carbazole group, is exemplified. The present invention is not limited to this.

The color conversion composition of the embodiment of the present invention may optionally contain other compounds, in addition to the compound represented by the formula (4). For example, in order to further increase the energy transfer efficiency of the self-excitation light toward the compound represented by the general formula (4), an auxiliary dopant such as red fluorene may be contained. Further, when an illuminating color other than the luminescent color of the compound represented by the general formula (4) is to be added, a desired organic luminescent material such as a coumarin-based dye or a rhodamine-based dye may be added. Further, in addition to the organic light-emitting materials, a known light-emitting material such as an inorganic phosphor, a fluorescent pigment, a fluorescent dye, or a quantum dot may be added in combination.

Hereinafter, an example of the organic light-emitting material other than the compound represented by the general formula (4) is shown below, but the present invention is not particularly limited to these examples.

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The color conversion composition of the embodiment of the present invention is preferably contained in a region having a peak wavelength of 500 nm or more and 580 nm or less by using excitation light having a wavelength of 430 nm or more and 500 nm or less. A light-emitting luminescent material (hereinafter referred to as "light-emitting material (a)"). In the future, the luminescence observed in a region having a peak wavelength of 500 nm or more and 580 nm or less is referred to as "green luminescence". Generally, the greater the energy of the excitation light, the more likely it is to cause decomposition of the material. However, excitation light having a wavelength of 430 nm or more and 500 nm or less is relatively small in excitation energy. Therefore, decomposition of the luminescent material (a) in the color conversion composition is not caused, and green luminescence with good color purity can be obtained.

The color conversion composition of the embodiment of the present invention preferably contains the following luminescent material (a) and luminescent material (b). As described above, the luminescent material (a) is a luminescent material that emits light having a peak wavelength of 500 nm or more and 580 nm or less by using excitation light having a wavelength of 430 nm or more and 500 nm or less. The luminescent material (b) is excited by at least one of excitation light having a wavelength of 430 nm or more and 500 nm or less and luminescence from the luminescent material (a), thereby exhibiting a peak wavelength of 580 nm or more and 750. Luminescent luminescent material observed in the region below nm. In the future, the luminescence observed in a region having a peak wavelength of 580 nm or more and 750 nm or less is referred to as "red luminescence".

A part of the excitation light having a wavelength of 430 nm or more and 500 nm or less is partially transmitted through the color conversion film of the embodiment of the present invention. Therefore, when a blue LED having a sharp emission peak is used, the colors of blue, green, and red are used. A sharp luminescence spectrum is shown, and white light with good color purity can be obtained. As a result, especially in the display, it is possible to efficiently produce a color gamut that is more vivid and larger. Further, in the lighting use, the light-emitting characteristics of the green region and the red region are particularly improved as compared with the white LED in which the blue LED and the yellow phosphor are combined, so that the color rendering property can be improved. White light source.

As the luminescent material (a), coumarin derivatives such as coumarin 6, coumarin 7, coumarin 153, cyanine derivatives such as phthalocyanine, luciferin, luciferin isothiocyanate Fluorescent derivatives such as esters and carboxyfluorescein diacetate, phthalocyanine derivatives such as phthalocyanine green, diisobutyl-4,10-dicyanoindole-3,9-dicarboxylate, etc. Examples of the derivative include a pyrrolethymethylene derivative, a stilbene derivative, an oxazine derivative, a naphthoquinone imine derivative, a pyrazine derivative, a benzimidazole derivative, and a benzoxazole derivative. A benzothiazole derivative, an imidazopyridine derivative, an azole derivative, a compound having a condensed aryl ring such as hydrazine or a derivative thereof, an aromatic amine derivative, an organometallic compound, or the like is suitable. However, the luminescent material (a) is not particularly limited to these compounds. Among these compounds, pyrrolethymethylene derivatives are particularly suitable compounds because they provide high luminescence quantum yield and good durability. Among the pyrrolethymethylene derivatives, the compound represented by the formula (4) is preferred because it exhibits excellent light emission with high purity.

As the luminescent material (b), except for 4-cyanomethylene-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran, etc., rhodamine B, Rhodamine 6G, Rhodamine 101, sulforhodamine 101 and other rhodamine derivatives, 1-ethyl-2-(4-(p-dimethylaminophenyl)-1,3-butadienyl)- Pyridine derivative such as pyridinium-perchlorate, N,N'-bis(2,6-diisopropylphenyl)-1,6,7,12-tetraphenoxyindole-3,4,9 In addition to an anthracene derivative such as 10-bisbicarbimine, a porphyrin derivative, a pyrromethene derivative, an oxazine derivative, a pyrazine derivative, a condensed tetraphenyl or a dibenzodiazepine may be mentioned. A compound having a condensed aryl ring or a derivative thereof, an organometallic compound or the like is suitable. However, the luminescent material (b) is not particularly limited to these compounds.

Among these compounds, pyrrolethymethylene derivatives are particularly suitable compounds because they provide high luminescence quantum yield and good durability. Among the pyrrolethymethylene derivatives, the compound represented by the formula (4) is preferred because it exhibits excellent light emission with high purity.

The content of the component (A) in the color conversion composition of the embodiment of the present invention depends on the molar absorption coefficient, the luminescence quantum yield, and the absorption intensity in the excitation wavelength of the compound, and the thickness or permeation of the produced film. The ratio is usually 1.0 × 10 ^-4 parts by weight to 30 parts by weight per 100 parts by weight of the component (B). The content of the component (A) is more preferably 1.0 × 10 ^-3 parts by weight to 10 parts by weight, particularly preferably 1.0 × 10 ^-2 parts by weight to 5 parts by weight, per 100 parts by weight of the component (B).

Further, when the color conversion composition contains both the luminescent material (a) that emits green light and the luminescent material (b) that emits red light, a part of the green light is converted into a red light. , preferably the luminescent material (a), the content of w _a light emitting material (b) in relation to the content of w _b w _a ≧ w _b of. Further, the content ratio of the luminescent material (a) and the luminescent material (b) is w _a : w _b = 1000:1 to 1:1, more preferably 500:1 to 2:1, and particularly preferably 200:1. ~3:1. Here, the content w _a and the content w _b are weight percentages relative to the weight of the component (B).

<Component (B): Binder Resin> The color conversion composition of the embodiment of the present invention contains a binder resin as the component (B). The binder resin may be a material that forms a continuous phase as long as it is excellent in moldability, transparency, heat resistance, and the like. Examples of the binder resin include a photocurable resist material having a reactive vinyl group such as an acrylic resin, a methacrylic resin, a polycinnamic acid vinyl group, or a ring rubber system, and an epoxy resin or an anthracene. Ketone resin (including organic polyoxyalkylene cured product (crosslinking) such as anthrone rubber, anthrone gel), urea resin, fluororesin, polycarbonate resin, acrylic resin, urethane resin, melamine resin , polyvinyl resin, polyamide resin, phenol resin, polyvinyl alcohol resin, polyvinyl butyral resin, cellulose resin, aliphatic ester resin, aromatic ester resin, aliphatic polyolefin resin, aromatic polyolefin resin And other known people. Further, as the binder resin, these copolymer resins can also be used. By suitably designing these resins, a binder resin useful for the color conversion composition and the color conversion film of the embodiment of the present invention can be obtained.

Among these resins, the film forming process is more preferably a thermosetting resin. Among the thermosetting resins, an epoxy resin, an anthrone resin, an acrylic resin, a polyester resin or a mixture of these may be suitably used from the viewpoint of transparency, heat resistance and the like.

Further, a dispersant or a leveling agent for stabilizing the coating film may be added as an additive to the binder resin, and a bonding aid such as a decane coupling agent may be added as a modifier for the surface of the film. Further, inorganic particles such as cerium oxide particles or fluorenone fine particles may be added to the binder resin as a color conversion material precipitation inhibitor.

Further, from the viewpoint of heat resistance, the binder resin is particularly preferably an anthrone resin. Among the fluorenone resins, an addition reaction-curable fluorenone composition is preferred. The addition reaction-curable anthrone composition is heated and hardened at a normal temperature or a temperature of 50 to 200 ° C, and is excellent in transparency, heat resistance, and adhesion.

As an example, the addition reaction-curable fluorenone composition is formed by hydrogenation of a compound containing an alkenyl group bonded to a ruthenium atom with a ruthenium containing a hydrogen atom bonded to a ruthenium atom. Among such materials, examples of the "compound containing an alkenyl group bonded to a ruthenium atom" include vinyl trimethoxy decane, vinyl triethoxy decane, allyl trimethoxy decane, and propylene. Trimethoxy decane, norbornene trimethoxy decane, octenyl trimethoxy decane, and the like. Examples of the "compound containing a hydrogen atom bonded to a ruthenium atom" include methyl hydrogen polyoxy siloxane, dimethyl polyoxy siloxane - CO-methyl hydrogen polyoxy siloxane, and ethyl hydrogen polymerization. A halogenated alkane, a methyl hydrogen polyoxyalkylene-CO-methylphenyl polyoxyalkylene or the like. In addition, as an addition reaction-curable fluorene ketone composition, a well-known person as described in Japanese Laid-Open Patent Publication No. 2010-159411, for example, may be used.

Further, as the addition reaction-curable anthrone composition, a commercially available one, for example, an anthrone sealing material for general LED use can be used. Specific examples thereof include OE-6630A/B manufactured by Toray Dow Corning Corporation, OE-6336A/B, or SCR-1012A/B and SCR-1016A/B manufactured by Shin-Etsu Chemical Co., Ltd.

In the color conversion composition for producing a color conversion film according to the embodiment of the present invention, in order to suppress curing at normal temperature and to extend the pot life, it is preferred to prepare a binder for the hydrogenation reaction retardant such as acetylene alcohol as a component. In the resin. Further, in the range in which the effects of the present invention are not impaired, fine particles such as smoked ceria, glass powder, and quartz powder may be blended into the binder resin as needed, and inorganic fillers such as titanium oxide, zirconium oxide, barium titanate, and zinc oxide may be added. An agent or a pigment, a flame retardant, a heat resistant agent, an antioxidant, a dispersant, a solvent, a decane coupling agent or a titanium coupling agent or the like.

In particular, from the viewpoint of surface smoothness of the color conversion film, it is preferred to add a low molecular weight polydimethyl siloxane component, eucalyptus oil, or the like to the fluorenone resin composition for color conversion film production. The component is preferably added in an amount of from 100 ppm to 2,000 ppm, more preferably from 500 ppm to 1,000 ppm, based on the total of the fluorenone resin composition.

<(C) component: an amine derivative having a partial structure represented by the general formula (1)> The color conversion composition of the embodiment of the present invention contains an amine derivative having a partial structure represented by the general formula (1) As component (C).

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In the formula (1), R ¹⁰ to R ¹⁴ may be the same or different, and may be selected from a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a heteroaryl group. Wherein at least one of R ¹¹ and R ¹² and at least one of R ¹³ and R ¹⁴ are not a hydrogen atom.

The amine derivative having a partial structure represented by the general formula (1) prevents deterioration of the organic light-emitting material and improves durability. Therefore, the decrease in the luminescence intensity of the component (A) (one or more organic luminescent materials) over time is suppressed by the action of the amine derivative. This effect is particularly large when the organic light-emitting material as the component (A) is a compound represented by the general formula (4).

As a cause of deterioration of the organic light-emitting material, there is oxidation caused by a radical species generated by light irradiation. For example, an alkyl radical (R·) which is minutely generated by light irradiation rapidly reacts with oxygen to generate a peroxy radical (ROO·). It is considered that the peroxide (ROOH) generated from the peroxy radical is cleaved, whereby the radical species are acceleratedly increased to cause oxidative degradation of the organic light-emitting material.

The amine derivative having a partial structure represented by the general formula (1) generates a nitroxide radical by reacting with a peroxy radical. The nitroxide radical reacts with the alkyl radical to thereby produce an alkoxyamine, but the alkoxyamine reacts with the peroxy radical, thereby changing again to a nitroxide radical. It is considered that by repeating such a reaction, radical species generated by light irradiation are passivated, and thus oxidative degradation of the organic light-emitting material can be suppressed.

In the formula (1), at least one of R ¹¹ and R ¹² and at least one of R ¹³ and R ¹⁴ are not a hydrogen atom. The reason for this is that moderate stability can be imparted to the nitroxide radical by the presence of a substituent in the vicinity of the nitrogen atom.

Further, in the general formula (1), R ¹¹ to R ^{14 are more} preferably an alkyl group or a cycloalkyl group from the viewpoint of solubility or ease of synthesis. Further, it is more preferably an alkyl group, and among the alkyl groups, a methyl group is preferred.

From the viewpoint of high reactivity with a peroxy radical, R ^{10 is} preferably a hydrogen atom, an alkyl group or a cycloalkyl group, more preferably a hydrogen atom or an alkyl group. Further, from the viewpoint that the alkalinity is low, the influence on the organic light-emitting material is small, and R ^{10 is} preferably an alkyl group, and among the alkyl groups, a methyl group is preferred.

The amine derivative (component (C)) having a partial structure represented by the formula (1) is preferably a compound having a piperidine skeleton represented by the following formula (2). The reason for this is that the degree of freedom around the nitrogen atom is moderately small. The nitroxide radical is further stabilized by the moderate degree of freedom around the nitrogen atom being moderately reduced. Further, an appropriate space is ensured around the nitrogen atom, whereby the reaction between the amine moiety and the radical species proceeds easily.

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In the compound having a piperidine skeleton represented by the formula (2), R ¹⁰ to R ^{14 are the} same as R ¹⁰ to R ¹⁴ of the formula (1).

The component (C) is not particularly limited to a compound having a piperidine skeleton as described above, and is preferably a 4-hydroxypiperidine derivative or a 4-aminopiperidine derivative, from the viewpoint of easy synthesis. The -methoxypiperidine derivative or the like has a substituent at the 4-position of piperidine. Examples of the substituent include an alkyl group, a cycloalkyl group, a heterocyclic group, an alkenyl group, a cycloalkenyl group, an alkynyl group, a hydroxyl group, a thiol group, an alkoxy group, an alkylthio group, an aryl ether group, and an aryl group. Thioether, aryl, heteroaryl, halogen, cyano, aldehyde, carbonyl, carboxyl, oxycarbonyl, aminecardenyl, amine, nitro, decyl, decyloxy, oxo, oxidized Phosphine and the like. Among these, an alkyl group, a hydroxyl group, an alkoxy group, a cyano group, a carbonyl group, a carboxyl group, an oxycarbonyl group, an amine carbaryl group, and an amine group are preferable. More preferably, it is a hydroxyl group, an alkoxy group, or an oxycarbonyl group.

Among them, the component (C) is preferably a compound represented by the formula (3) because the degree of freedom of movement of the piperidine skeleton portion is increased, and peroxy radicals can be more efficiently captured.

[39]

In the general formula (3), the same R R ¹⁰ ~ R ¹⁴ in the general formula (1) is ¹⁰ ~ R ^14. m is a natural number. Y is selected from a single bond, a chain or cyclic aliphatic hydrocarbon, an aliphatic heterocyclic ring, an aromatic hydrocarbon ring, an aromatic hetero ring, or a combination thereof.

Further, in the general formula (3), m is more preferably a natural number of 2 or more. The reason for this is that when the compound represented by the general formula (3) has a plurality of piperidine skeletons in the same molecule, the efficiency of radical scavenging is improved. Further, from the viewpoint of easiness of synthesis, m is preferably a natural number of 10 or less, and more preferably a natural number of 6 or less.

Further, in the general formula (3), Y is preferably a single bond, a chain or a cyclic aliphatic hydrocarbon, an aromatic hydrocarbon ring, or a combination thereof in terms of light resistance. Further, from the viewpoint of flexibility of the molecule, Y is more preferably a chain aliphatic hydrocarbon, a cyclic aliphatic hydrocarbon, a benzene ring, or a combination thereof.

When Y is the combination, the structure of Y is not particularly limited to the following, and examples thereof include a structural unit including a chain aliphatic hydrocarbon and a structural unit containing a cyclic aliphatic hydrocarbon. A structure or a structure in which a structural unit containing a chain aliphatic hydrocarbon is bonded to a structural unit containing an aromatic hydrocarbon ring, or a structure in which two or more structural units including a chain aliphatic hydrocarbon are linked. In the structure of such Y, from the viewpoint of easiness of synthesis, it is preferred that each structural unit is linked via an ester bond or an ether bond.

Further, in the general formula (3), Y is more preferably a chain aliphatic hydrocarbon or a cyclic aliphatic hydrocarbon from the viewpoint of solubility of the solvent, and from the viewpoint of easiness of synthesis, Y Further, it is more preferably a chain aliphatic hydrocarbon. The chain aliphatic hydrocarbon is particularly preferably a saturated aliphatic hydrocarbon.

However, the Y may be substituted with a substituent other than the partial structure shown in the formula (3). Examples of the substituent include an alkyl group, a cycloalkyl group, a heterocyclic group, an alkenyl group, a cycloalkenyl group, an alkynyl group, a hydroxyl group, a thiol group, an alkoxy group, an alkylthio group, an aryl ether group, and an aryl group. Thioether, aryl, heteroaryl, halogen, cyano, aldehyde, carbonyl, carboxyl, oxycarbonyl, aminecardenyl, amine, nitro, decyl, decyloxy, oxo, oxidized Phosphine and the like.

Further, examples of Y as the general formula (3) include the following, but are not limited to these examples. Among them, the black dot of the bonding end portion in the following structural formula is bonded to the black dot of the bonding end portion in the general formula (9). Further, in the following structural formula, n is an integer of 0 or more. When a plurality of n are displayed, each n may be the same or different. In the following examples, unsubstituted Y is shown, but Y may be substituted by the substituent. Further, the same as R of formula (9) ¹⁰ ~ R ¹⁴ in the general formula (1) is R ¹⁰ ~ R ^14.

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On the other hand, when the molecular weight of the compound represented by the formula (1) is too small, diffusion or aggregation due to heat is likely to occur, and therefore it is preferably 100 or more, and more preferably 150 or more. More preferably, it is 200 or more. Further, when the molecular weight of the compound is too large, the solubility is lowered. Therefore, the molecular weight is preferably 1,000 or less, more preferably 900 or less. More preferably, it is 800 or less.

Further, from the viewpoint of not inhibiting light emission from the light source or light emission of the luminescent material, the compound represented by the general formula (1) preferably has a small absorption coefficient in the visible region. Specifically, in the entire region of the wavelength region of the wavelength of 400 nm or more and 800 nm or less, the molar absorption coefficient ε of the compound is preferably 1,000 or less, more preferably 500 or less. Further, it is more preferably 200 or less, and particularly preferably 100 or less.

The compound represented by the formula (1) is exemplified by the following examples, but is not limited to these examples.

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In the color conversion composition of the embodiment of the present invention, the content of the component (C) depends on the molar absorption coefficient, the luminescence quantum yield, and the absorption intensity in the excitation wavelength of the compound, and the color conversion film produced. The thickness or the transmittance is preferably 1.0 × 10 ^-3 parts by weight or more, more preferably 1.0 × 10 ^-2 parts by weight or more, and still more preferably 1.0 × 10 ^-1 with respect to 100 parts by weight of the component (B). More than the weight. Further, the content of the component (C) is preferably 30 parts by weight or less, and more preferably 10 parts by weight or less based on 100 parts by weight of the component (B).

<Other Additives> The color conversion composition of the embodiment of the present invention may contain light resistance such as an antioxidant, a processing, a heat stabilizer, or an ultraviolet absorber, in addition to the components (A), (B) and (C). Other additives such as stabilizers, inorganic particles such as fluorenone microparticles, and decane coupling agents.

Examples of the antioxidant include phenolic antioxidants such as 2,6-di-t-butyl-p-cresol and 2,6-di-t-butyl-4-ethylphenol, but are not particularly limited thereto. These antioxidants. Further, the antioxidants may be used singly or in combination of two or more.

Examples of the processing and heat stabilizer include phosphorus stabilizers such as tributyl phosphite, tricyclohexyl phosphite, triethylphosphine, and diphenylbutylphosphine, but are not particularly limited to the stabilizers. . Further, the stabilizers may be used singly or in combination of two or more.

Examples of the light resistance stabilizer include 2-(5-methyl-2-hydroxyphenyl)benzotriazole and 2-[2-hydroxy-3,5-bis(α,α-dimethylbenzyl). Benzene triazole such as phenyl]-2H-benzotriazole, but is not particularly limited to these light resistance stabilizers. Further, these light resistance stabilizers may be used singly or in combination of two or more.

The additives preferably have a small absorption coefficient in the visible region from the viewpoint of not hindering the light from the light source or the luminescence of the luminescent material. Specifically, in the entire region of the wavelength region of the wavelength of 400 nm or more and 800 nm or less, the molar absorption coefficient ε of the additives is preferably 1,000 or less, more preferably 500 or less. Further, it is more preferably 200 or less, and particularly preferably 100 or less.

Further, as the light resistance stabilizer, a compound having a function as a singlet oxygen quencher can be suitably used. A singlet oxygen quencher is a material that captures the oxygen species and activates the formed singlet oxygen by the energy of light. By the coexistence of the singlet oxygen quencher in the composition, the luminescent material can be prevented from deteriorating due to singlet oxygen.

Singlet oxygen is known to be produced by the exchange of electrons and energy between the triplet excited state of a pigment such as rose bengal or methylene blue and the oxygen molecules in the basal state.

In the color conversion composition according to the embodiment of the present invention, the organic light-emitting material contained therein is excited by the excitation light, and emits light having a wavelength different from that of the excitation light to perform color conversion of light. Since the cycle of the excitation-luminescence is repeated, the probability of generating singlet oxygen by the interaction between the generated excited species and the oxygen contained in the composition becomes high. Therefore, the collision probability of the organic light-emitting material and the singlet oxygen also becomes high, and the deterioration of the organic light-emitting material is easily advanced.

Compared to inorganic luminescent materials, organic luminescent materials are susceptible to singlet oxygen. In particular, the compound represented by the formula (4) has high reactivity with singlet oxygen, and the effect on durability from singlet oxygen, compared with a compound having a condensed aryl ring such as hydrazine or a derivative thereof. Big. Therefore, the generated singlet oxygen is rapidly passivated by the singlet oxygen quencher, whereby the durability of the compound represented by the general formula (4) excellent in luminescence quantum yield and color purity can be improved.

Examples of the compound having a function as a singlet oxygen quencher include a specific tertiary amine, a catechol derivative, and a nickel compound, but are not particularly limited to these compounds. Further, these compounds (light stabilizers) may be used singly or in combination of two or more.

The tertiary amine means a compound having a structure in which an N-H bond of ammonia is substituted by an N-C bond. As a substituent on a nitrogen atom, from an alkyl group, a cycloalkyl group, a heterocyclic group, an alkenyl group, a cycloalkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aldehyde group, a carbonyl group, a carboxyl group, an oxycarbonyl group, an amine formazan The condensed ring and the aliphatic ring formed between the group and the adjacent substituent are selected. Further, the substituents may be further substituted by the substituent.

As the substituent on the nitrogen atom of the tertiary amine, from the viewpoint of photostability, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, substituted or Unsubstituted aryl, substituted or unsubstituted heteroaryl. Of these, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group is more preferred.

The aryl group in this case is preferably a phenyl group or a naphthyl group, and more preferably a phenyl group, in order not to hinder light emission from the light source or light emission from the light-emitting material. Further, when the aryl group on the nitrogen atom increases, there is a concern that the absorption of light in the visible region increases. Therefore, among the three substituents on the nitrogen atom, the aryl group is preferably two or less, more preferably one or less. . When at least one of the three substituents on the nitrogen atom is a substituted or unsubstituted alkyl group, singlet oxygen can be more efficiently captured, which is preferable. Among them, it is preferred that two or more of the three substituents are substituted or unsubstituted alkyl groups.

As preferred tertiary amines, there may be mentioned triethylamine, 1,4-diazabicyclo[2.2.2]octane, tri-n-butylamine, N,N-diethylaniline, 2,2. 6,6-tetramethylpiperidine or the like, but is not particularly limited to the tertiary amines.

Further, the compound represented by the formula (2) is a tertiary amine as long as R ¹⁰ is an alkyl group. That is, the compound also functions as a singlet oxygen quencher.

The catechol derivative is a compound containing an isomer such as resorcin or hydroquinone, and having two or more hydroxyl groups on the benzene ring. These compounds can capture singlet oxygen more efficiently than phenol derivatives having one hydroxyl group on the phenyl ring.

As a substituent on the benzene ring of the catechol derivative, in addition to the hydroxyl group, it is also derived from hydrogen, an alkyl group, a cycloalkyl group, a heterocyclic group, an alkenyl group, a cycloalkenyl group, an alkynyl group, a thiol group or an alkoxy group. , alkylthio, aryl ether, aryl sulfide, aryl, heteroaryl, halogen, cyano, aldehyde, carbonyl, carboxyl, oxycarbonyl, aminecarboxamidine, amine, nitro, decyl The oxiranyl group, the boroxyl group, the phosphine oxide group, and the condensed ring formed between the adjacent substituents and the aliphatic ring are selected. Further, the substituents may be further substituted by the substituent.

Among them, from the viewpoint of photostability, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, substituted or unsubstituted is preferred. The substituted heteroaryl group, halogen, more preferably a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a halogen. In terms of small discoloration after the reaction with the singlet oxygen quencher, it is more preferably a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, or a halogen. Particularly preferred are substituted or unsubstituted alkyl groups.

The position of the hydroxyl group on the benzene ring in the catechol derivative is preferably at least two hydroxyl groups adjacent to each other. The reason for this is that it is difficult to be photooxidized compared to resorcinol (1,3-substituted) or hydroquinone (1,4-substituted). Further, since the absorption of light in the visible region is small after oxidation, discoloration of the composition can be prevented.

Preferred examples of the catechol derivative include 4-tert-butylbenzene-1,2-diol and 3,5-di-t-butylbenzene-1,2-diol, but not It is particularly limited to these catechol derivatives.

The nickel compound refers to a compound containing nickel. The nickel compound may, for example, be an inorganic salt such as nickel chloride or a complex such as acetoacetone nickel or an organic acid salt such as a nickel urinate, but is not particularly limited to these nickel compounds. Here, the organic acid means an organic compound having a carboxyl group, a sulfonyl group, a phenolic hydroxyl group, or a thiol group. Among them, as the nickel compound, a complex compound and an organic acid salt are preferred from the viewpoint of uniformly dispersing the composition.

Examples of the nickel complex which can be suitably used as the singlet oxygen quencher and the nickel salt of the organic acid include, for example, an acetonitrile acetone nickel complex and a bisdithio-α-diketone nickel complex. , a dithiolate nickel complex, an amine thiolate nickel complex, a thiocatechol nickel complex, a salicyl hydrazine nickel complex, a thiobisphenolate nickel a substance, an anisidine-based nickel compound, a carboxylic acid-based nickel salt, a sulfonic acid-based nickel salt, a phenol-based nickel salt, a urethane-based nickel salt, a dithiocarbamic acid-based nickel salt, etc., but is not particularly limited to these compounds .

Among these, the nickel compound is preferably at least one of a nickel salt of an organic acid, an acetonitrile acetone nickel complex, and a thiobisphenolate nickel complex. In particular, a nickel salt of an organic acid is preferred from the viewpoint of easiness of synthesis and low cost. Further, from the viewpoint that the molar absorption coefficient in the visible region is small and the light source or the light-emitting material is not absorbed, the sulfonic acid-based nickel salt is preferred. From the viewpoint of exhibiting a more excellent singlet oxygen quenching effect, it is more preferable that the nickel salt of the arylsulfonic acid is more preferably an alkyl group from the viewpoint of solubility of a wide variety of solvents. Nickel salt of sulfonic acid. The aryl group of the arylsulfonic acid is preferably a substituted or unsubstituted phenyl group, and more preferably an alkyl group-substituted phenyl group from the viewpoint of solubility in a solvent and dispersibility.

Further, as the nickel compound, from the viewpoint of solubility in an organic solvent and a molar absorption coefficient in a visible region, it is preferred that the acetonitrile acetone nickel complex and the thiobisphenolate nickel are misaligned. Both. The ligand on the nickel in the complexes may be alkyl, cycloalkyl, heterocyclyl, alkenyl, cycloalkenyl, alkynyl, thiol, alkoxy, alkylthio, aryl ether , aryl sulfide group, aryl group, heteroaryl group, halogen, cyano group, aldehyde group, carbonyl group, carboxyl group, oxycarbonyl group, amine methyl group, amine group, nitro group, decyl group, decyloxy group, boron boron Substituents such as a phosphine oxide group or the like are substituted. Further, the substituents may be further substituted by the substituent.

Among them, from the viewpoint of photostability, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, substituted or unsubstituted is preferred. The substituted heteroaryl group, halogen, more preferably a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a halogen. Further, in terms of small discoloration after the reaction with the singlet oxygen quencher, it is more preferably a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group or a halogen. Particularly preferred are substituted or unsubstituted alkyl groups.

The nickel compound having a molar absorption coefficient ε of 100 or less in the entire wavelength region of the wavelength range of 400 nm or more and 800 nm or less is, for example, a nickel salt of p-tolylsulfonylsulfonic acid or nickel (II) acetonitrile. Complex, hexafluoroacetone nickel(II) complex, 2,2'-thiobisphenolate-n-butylamine nickel(II) complex, [2,2'-thiobis ( 4-tert-octylphenolate]]-2-ethylhexylamine nickel (II) complex and the like. However, the nickel compound is not limited to the nickel salt or the nickel complex, and among the various nickel compounds, moiré can be used in the entire region of the wavelength region of wavelengths of 400 nm or more and 800 nm or less. The coefficient ε is 100 or less.

In the color conversion composition of the embodiment of the present invention, the content of the additives depends on the molar absorption coefficient of the compound, the luminescence quantum yield, and the absorption intensity in the excitation wavelength, and the thickness of the produced color conversion film. Or the transmittance, but it is usually 1.0 × 10 ^-3 parts by weight or more, more preferably 1.0 × 10 ^-2 parts by weight or more, and still more preferably 1.0 × 10 ^-1 with respect to 100 parts by weight of the component (B). More than the weight. Further, the content of the additives is preferably 30 parts by weight or less, more preferably 15 parts by weight or less, still more preferably 10 parts by weight or less based on 100 parts by weight of the component (B).

<Solvent> The color conversion composition of the embodiment of the present invention may contain a solvent. The solvent is not particularly limited as long as it is a viscosity of the resin in a flowable state and does not excessively affect the light emission and durability of the luminescent material. Examples of such a solvent include water, 2-propanol, ethanol, toluene, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, hexane, acetone, terpineol, 2, 2, 4-trimethyl-1,3-pentanediol monoisobutyrate (texanol), methyl cellosolve, ethyl cellosolve, butyl carbitol, butyl carbitol acetate, 1 -Methoxy-2-propanol, propylene glycol monomethyl ether acetate, and the like. Two or more of these solvents may also be used in combination. Among these solvents, in particular, toluene is not affected from the viewpoint of deterioration of the compound represented by the general formula (4), and the amount of residual solvent after drying is small.

<Method for Producing Color Conversion Composition> Hereinafter, an example of a method for producing a color conversion composition according to an embodiment of the present invention will be described. In the production method, a predetermined amount of the organic light-emitting material (component (A)), a binder resin (component (B)), an amine derivative (component (C)), a solvent, and the like are mixed. The components are mixed in a predetermined composition, and then uniformly mixed and dispersed by a stirring and kneading machine such as a homogenizer, a self-rotating mixer, a three-roll mill, a ball mill, a planetary ball mill, or a bead mill. Color conversion composition. Defoaming may also preferably be carried out under vacuum or reduced pressure during mixing or dispersion or during mixing and dispersion. Further, it is also possible to mix a specific component in advance or perform treatment such as aging. The solvent can also be removed using an evaporator to become the desired solids concentration.

<Method for Producing Color Conversion Film> In the present invention, the color conversion film is not limited as long as it includes a layer obtained by curing the color conversion composition (that is, a cured layer of the color conversion composition). As a typical structural example of a color conversion film, the following three examples are mentioned, for example.

Fig. 1 is a schematic cross-sectional view showing an example of a color conversion film according to an embodiment of the present invention. The color conversion film 1 illustrated in FIG. 1 is a laminate of the base material layer 10 and the color conversion layer 11. The color conversion layer 11 is a cured layer of the color conversion composition. In the configuration example of the color conversion film 1, the color conversion layer 11 is laminated on the base material layer 10.

Fig. 2 is a schematic cross-sectional view showing another example of the color conversion film according to the embodiment of the present invention. The color conversion film 1 illustrated in FIG. 2 is a laminated body of a plurality of base material layers 10 and color conversion layers 11. In the configuration example of the color conversion film 1, the color conversion layer 11 is sandwiched by a plurality of base material layers 10.

3 is a schematic cross-sectional view showing still another example of the color conversion film according to the embodiment of the present invention. The color conversion film 1 illustrated in FIG. 3 is a laminate of a plurality of base material layers 10, a color conversion layer 11, and a plurality of barrier films 12. In the configuration example of the color conversion film 1, the color conversion layer 11 is sandwiched by the plurality of barrier films 12, and further, the laminate of the color conversion layer 11 and the plurality of barrier films 12 is sandwiched by the plurality of substrate layers 10. . That is, in the color conversion film 1, in order to prevent deterioration of the color conversion layer 11 by oxygen, moisture, or heat, the barrier film 12 may be provided as illustrated in FIG.

(Base Material Layer) As the base material layer (for example, the base material layer 10 shown in FIGS. 1 to 3), a known metal, film, glass, ceramic, paper, or the like can be used without particular limitation. Specifically, examples of the substrate layer include aluminum (also including aluminum alloy), metal plates or foils such as zinc, copper, and iron, and cellulose acetate and polyethylene terephthalate (PET). , polyethylene, polyester, polyamide, polyimide, polyphenylene sulfide, polystyrene, polypropylene, polycarbonate, polyvinyl acetal, aromatic polyamine, fluorenone, polyolefin, thermoplastic a film of a plastic such as a fluororesin, an ethylene tetrafluoroethylene (ETFE) or the like, comprising an α-polyolefin resin, a polycaprolactone resin, an acrylic resin, an anthrone resin, and a copolymer resin with the ethylene. a plastic film, a paper laminated with the plastic, or a paper coated with the plastic, a paper laminated or vapor-deposited, a plastic film laminated or vapor-deposited with the metal, or the like . Further, when the base material layer is a metal plate, the surface may be subjected to a plating treatment such as chromium or nickel or a ceramic treatment.

Among these, a glass or a resin film can be preferably used in terms of easiness in production of a color conversion film or ease of formation of a color conversion film. Further, in order to treat the film-form substrate layer without cracking or the like, a film having high strength is preferable. In terms of such required characteristics or economical efficiency, a resin film is preferred, and among these, in terms of economy and handling, it is preferably selected from the group consisting of PET, polyphenylene sulfide, polycarbonate, and poly. A plastic film in a group consisting of propylene. In the case where the color conversion film is dried or when the color conversion film is pressure-bonded at a high temperature of 200 ° C or higher by an extruder, a polyimide film is preferable in terms of heat resistance. In terms of easiness of peeling off the film, the surface of the base material layer may be subjected to release treatment in advance.

The thickness of the base material layer is not particularly limited, but the lower limit is preferably 5 μm or more, more preferably 25 μm or more, and still more preferably 38 μm or more. Further, the upper limit is preferably 5,000 μm or less, more preferably 3,000 μm or less.

(Color Conversion Layer) Next, an example of a method of producing a color conversion layer of the color conversion film according to the embodiment of the present invention will be described. In the method for producing the color conversion layer, the color conversion composition produced by the method is applied onto a substrate such as a substrate layer or a barrier film layer, and dried. In this manner, a color conversion layer (for example, the color conversion layer 11 shown in FIGS. 1 to 3) is produced. The coating can be applied by a reverse roll coater, a blade coater, a slit die coater, a direct gravure coater, an indirect gravure coater. Offset gravure coater, kiss coater, natural roll coater, air knife coater, roll blade coater Coater), reverse roll coat coater, two stream coater, rod coater, wire bar coater, applicator (applicator), a dip coater, a curtain coater, a spin coater, a knife coater, or the like. In order to obtain film thickness uniformity of the color conversion layer, coating is preferably carried out by a slot coater or a dip coater.

The drying of the color conversion layer can be carried out using a general heating device such as a hot air dryer or an infrared dryer. As the heating of the color conversion film, a general heating device such as a hot air dryer or an infrared dryer can be used. In this case, the heating conditions are usually 40 ° C to 250 ° C for 1 minute to 5 hours, preferably 60 ° C to 200 ° C for 2 minutes to 4 hours. Further, stepwise heat curing such as stepwise curing may be performed.

After the color conversion layer is formed, the substrate layer may be changed as needed. In this case, as a simple method, for example, a method of re-sticking using a hot plate or a method using a vacuum laminator or a dry film laminator may be mentioned, but the method is not limited thereto.

The thickness of the color conversion layer is not particularly limited, but is preferably 1 μm to 1000 μm, more preferably 10 μm to 1000 μm. When the thickness of the color conversion layer is less than 1 μm, there is a problem that the strength and toughness of the color conversion film become small. When the thickness of the color conversion layer exceeds 1000 μm, cracks are likely to occur, and the color conversion film is difficult to be formed. The thickness of the color conversion layer is more preferably 5 μm to 100 μm, still more preferably 10 μm to 100 μm, and particularly preferably 15 μm to 100 μm.

The film thickness of the color conversion film in the present invention refers to the film thickness (average film thickness) measured by the method A for measuring the thickness by mechanical scanning in the plastic-film and sheet-thickness measurement method of JIS K7130 (1999). ).

(Barrier Film) The barrier film (for example, the barrier film 12 and the like shown in FIG. 3) can be suitably used for the case where the gas barrier layer is improved in gas barrier properties and the like. Examples of the barrier film include inorganic oxides such as cerium oxide, aluminum oxide, titanium oxide, cerium oxide, zinc oxide, tin oxide, indium oxide, cerium oxide, and magnesium oxide, or cerium nitride, aluminum nitride, and nitrogen. An inorganic nitride such as titanium or niobium carbonitride, or a mixture thereof, or a metal oxide film or a metal nitride film obtained by adding other elements thereto, or comprising polyvinylidene chloride or acrylic resin A film of various resins such as a polyvinyl alcohol-based resin such as a lanthanum resin, a melamine resin, a urethane resin, a fluorine resin, or a saponified product of vinyl acetate. Further, examples of the barrier film having a barrier function against moisture include polyethylene, polypropylene, nylon, polyvinylidene chloride, vinylidene chloride and vinyl chloride, and copolymers of vinylidene chloride and acrylonitrile. A film of various resins such as a polyvinyl alcohol-based resin such as a fluorine resin or a saponified product of vinyl acetate.

The barrier film may be provided on both faces of the color conversion layer 11 as in the barrier film 12 illustrated in FIG. 3, or may be provided only on one surface of the color conversion layer 11. In addition, corresponding to the function required for the color conversion film, a light diffusion layer may be further provided, and has an anti-reflection function, an anti-glare function, an anti-reflection anti-glare function, a hard coating function (friction resistance function), an antistatic function, and an antifouling function. Function, electromagnetic wave shielding function, infrared cut-off function, ultraviolet cut-off function, polarizing function, auxiliary layer of color grading function.

<Excitation Light> Any type of excitation light can be used as long as it emits light in a wavelength region that can be absorbed by a luminescent material mixed with a compound represented by the general formula (4). For example, any of the fluorescent light source such as a hot cathode tube or a cold cathode tube, an inorganic electroluminescence (EL) element, an organic EL element light source, an LED light source, a white heat source, or sunlight can be used in principle. use. In particular, light from an LED source is a suitable excitation light. In the case of display or illumination applications, from the viewpoint of improving the color purity of blue light, light from a blue LED light source having excitation light in a wavelength range of 430 nm to 500 nm is a more suitable excitation light. If the wavelength range of the excitation light is on the longer wavelength side, the blue light is absent, so that white light cannot be formed, and if the wavelength range of the excitation light is on the shorter wavelength side, it is represented by the general formula (4). An organic compound such as a luminescent material such as a compound or a binder resin is easily deteriorated by light, which is not preferable.

The excitation light may have one kind of luminescence peak, or may have two or more luminescence peaks, but in order to improve color purity, it is preferable to have one luminescence peak. Further, a plurality of excitation light sources having different types of luminescence peaks may be used arbitrarily in combination.

<Light source unit> The light source unit according to the embodiment of the present invention has at least a light source, a color conversion composition, or a color conversion film. When the light source unit includes the color conversion composition, the method of arranging the light source and the color conversion composition is not particularly limited, and a configuration in which the color conversion composition is directly applied to the light source may be employed, or the color conversion composition may be coated. The structure is formed on a film or glass separated from the light source. When the light source unit includes a color conversion film, the method of arranging the light source and the color conversion film is not particularly limited, and a configuration in which the light source and the color conversion film are adhered to each other may be employed, and a remote fluorescent powder that separates the light source from the color conversion film may be used ( Remote Phosphor) form. Further, in order to improve the color purity, the light source unit may have a configuration in which a color filter is further provided.

As described above, the excitation light in the wavelength range of 430 nm to 500 nm is a relatively small excitation energy, and decomposition of a light-emitting substance such as a compound represented by the general formula (4) can be prevented. Therefore, the light source used for the light source unit is preferably a light-emitting diode having a maximum light emission in a wavelength range of 430 nm or more and 500 nm or less. Further, the light source preferably has maximum light emission in a range of wavelengths of 450 nm or more and 470 nm or less. The light source unit in the present invention can be used for display, illumination, interior decoration, signage, signboard, etc., and can be particularly suitably used for display or lighting purposes.

<Display and Illumination Device> The display according to the embodiment of the present invention includes at least a light source unit including a light source, a color conversion film, and the like as described above. For example, in a display such as a liquid crystal display, the light source unit is used as a backlight unit. Further, the illumination device according to the embodiment of the present invention includes at least a light source unit including a light source, a color conversion film, and the like as described above. For example, the illumination device combines a blue LED light source as a light source unit and a color conversion film or a color conversion composition that converts blue light from the blue LED light source into light having a longer wavelength than the light source, and emits white light. The way it is composed. Example

Hereinafter, the present invention will be described by way of examples, but the present invention is not limited by the examples described below. In the following examples and comparative examples, the compound G-1 to the compound G-6, the compound R-1 to the compound R-3, and the compound Q-1 to the compound Q-6 are the compounds shown below.

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In addition, the evaluation methods of the structural analysis in the examples and the comparative examples are as follows.

<Measurement ¹ H- NMR (Nuclear Magnetic Resonance, NMR) of> ¹ H-NMR using compound superconducting FTNMR EX-270 (JEOL Co., Ltd.) was measured in deuterated chloroform solution.

<Measurement of Absorption Spectrum> The absorption spectrum of the compound was measured by dissolving the compound in toluene at a concentration of 1 × 10 ^-6 mol/L using a U-3200 spectrophotometer (manufactured by Hitachi, Ltd.).

<Measurement of Fluorescence Spectrum> The fluorescence spectrum of the compound was measured by dissolving the compound in toluene at a concentration of 1 × 10 ^-6 mol/L using an F-2500 spectrophotometer (manufactured by Hitachi, Ltd.). And the fluorescence spectrum at the time of excitation at a wavelength of 460 nm.

<Measurement of color conversion characteristics> In the measurement of color conversion characteristics, various color conversion films and blue LED elements (manufactured by ProLight, Model No. PM2B-3LBE-SD, emission peak wavelength: 460 nm) were mounted. A current of 10 mA was flowed into the light-emitting device, and the blue LED element was turned on, and the luminescence spectrum and the peak wavelength were measured using a spectroradiometer (CS-1000, manufactured by Konica Minolta Co., Ltd.). Luminous intensity and chromaticity. Further, the distance between each color conversion film and the blue LED element was set to 3 cm.

<Test for Light Durability> In the light durability test, a light-emitting device equipped with a color conversion film and a blue LED element (manufactured by Prolet); model PM2B-3LBE-SD, emission peak wavelength: 460 nm) was used. The current of 10 mA was flowed in, and the blue LED element was turned on, and the initial luminance was measured using a spectroradiometer (CS-1000, manufactured by Konica Minolta Co., Ltd.). Further, the distance between each color conversion film and the blue LED element was set to 3 cm. Thereafter, the light from the blue LED element was continuously irradiated at room temperature, and the time until the luminance decreased by a fixed amount was observed, thereby evaluating the light durability.

(Synthesis Example 1) Hereinafter, a method for synthesizing the compound G-1 of Synthesis Example 1 in the present invention will be described. In the synthesis method of the compound G-1, 3,5-dibromobenzaldehyde (3.0 g), 4-tert-butylphenylboronic acid (5.3 g), tetrakis(triphenylphosphine)palladium(0) ( 0.4 g), potassium carbonate (2.0 g) was added to the flask and replaced with nitrogen. Degassed toluene (30 mL) and degassed water (10 mL) were added thereto, and refluxed for 4 hours. The reaction solution was cooled to room temperature, and the organic layer was separated and washed with saturated brine. The organic layer was dried over magnesium sulfate, filtered, and the solvent was evaporated. The obtained reaction product was purified by silica gel chromatography to obtain 3,5-bis(4-t-butylphenyl)benzaldehyde (3.5 g) as a white solid.

Then, 3,5-bis(4-t-butylphenyl)benzaldehyde (1.5 g) and 2,4-dimethylpyrrole (0.7 g) were added to the reaction solution, and dehydrated dichloromethane was added ( 200 mL) and trifluoroacetic acid (1 drop) were stirred under nitrogen for 4 hours. Then, a solution of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (0.85 g) in dehydrated dichloromethane was added, followed by stirring for 1 hour. After completion of the reaction, boron trifluoride diethyl ether complex (7.0 mL) and diisopropylethylamine (7.0 mL) were added, and after stirring for 4 hours, water (100 mL) was further added and stirred, and then The organic layer was separated. The organic layer was dried over magnesium sulfate, filtered, and the solvent was evaporated. The obtained reaction product was purified by silica gel chromatography to give Compound (0.4 g) (yield: 18%). The results of ¹ H-NMR analysis of the obtained compound were shown below, and it was confirmed to be Compound G-1. ¹ H-NMR (CDCl ₃ , ppm): 7.95 (s, 1H), 7.63-7.48 (m, 10H), 6.00 (s, 2H), 2.58 (s, 6H), 1.50 (s, 6H), 1.37 ( s, 18H).

Further, the absorption spectrum of the compound G-1 was as shown in Fig. 4, and the absorption characteristics of light were exhibited in a blue excitation light source (460 nm). Further, the fluorescence spectrum of the compound G-1 became as shown in Fig. 5, and showed a sharp luminescence peak in the green region. The luminescence quantum yield showed 83%, and the compound G-1 was a compound capable of performing efficient color conversion.

(Synthesis Example 2) Hereinafter, a method for synthesizing the compound R-1 of Synthesis Example 2 in the present invention will be described. In the synthesis method of the compound R-1, 4-(4-t-butylphenyl)-2-(4-methoxyphenyl)pyrrole (300 mg), 2 at 120 ° C under a nitrogen gas stream. A mixed solution of methoxybenzamide chloride (201 mg) and toluene (10 mL) was heated for 6 hours. After the heated solution was cooled to room temperature, it was evaporated. Then, it was washed with ethanol (20 mL) and vacuum dried to obtain 2-(2-methoxybenzimidyl)-3-(4-t-butylphenyl)-5-(4-methyl Oxyphenyl)pyrrole (260 mg).

Then, under a nitrogen gas stream, 2-(2-methoxybenzylidene)-3-(4-t-butylphenyl)-5-(4-methoxyphenyl)pyrrole at 125 °C (260 mg), 4-(4-t-butylphenyl)-2-(4-methoxyphenyl)pyrrole (180 mg), methanesulfonic anhydride (206 mg) and degassed toluene (10) The mixed solution of mL) was heated for 7 hours. After the heated solution was cooled to room temperature, water (20 mL) was poured, and the organic layer was extracted with dichloromethane (30 mL). The organic layer was washed twice with water (20 mL), evaporated, and dried in vacuo to obtain a pyrromethene.

Then, diisopropylethylamine (305 mg) and boron trifluoride diethyl ether complex were added to a mixed solution of the obtained pyrrolemethylene and toluene (10 mL) under a nitrogen gas stream. (670 mg) and stirred at room temperature for 3 hours. Thereafter, water (20 mL) was poured, and the organic layer was extracted with dichloromethane (30 mL). The organic layer was washed twice with water (20 mL), dried over magnesium sulfate, and evaporated. Then, it was purified by a silica gel column chromatography and vacuum dried to obtain a purple-red powder (0.27 g). The results of ¹ H-NMR analysis of the obtained magenta powder were as follows, and it was confirmed that the magenta powder obtained in the above manner was the compound R-1. ¹ H-NMR (CDCl ₃ , ppm): 1.19 (s, 18H), 3.42 (s, 3H), 3.85 (s, 6H), 5.72 (d, 1H), 6.20 (t, 1H), 6.42-6.97 ( m, 16H), 7.89 (d, 4H).

Further, the absorption spectrum of the compound R-1 was as shown in Fig. 6, and the absorption characteristics of light were exhibited in the blue and green excitation light sources. Further, the fluorescence spectrum of the compound R-1 showed a sharp luminescence peak in the red region as shown in Fig. 7 . The luminescence quantum yield showed 90%, and the compound R-1 was a compound capable of performing efficient color conversion.

(Example 1) In Example 1 of the present invention, an oxime resin "OE-6630A/B" (manufactured by Toray Dow Corning Co., Ltd.) was used as the component (B), and 100 parts by weight of the component (B). 0.20 parts by weight of the compound G-1 as the component (A), 0.5 part by weight of a curing agent, and 1.0 part by weight of the compound Q-1 as the component (C) were mixed. Then, using a planetary stirring/deaerator "Mazerustar KK-400" (manufactured by Kurabo), the mixture was stirred and defoamed at 1000 rpm for 20 minutes. A color conversion composition as a resin liquid for film production was obtained.

Then, the resin liquid for film production was applied to "Cerapeel" BLK (manufactured by Toray Film Processing Co., Ltd.) using a slot coater, and heated at 130 ° C for 2 hours. Drying was carried out to obtain a color conversion film having a film thickness of 200 μm.

As a result of color conversion of the blue LED light by the color conversion film, if only the light-emitting region of the green light is selected, a peak wavelength of 526 nm and a half-width of the emission spectrum in the peak wavelength of 25 nm can be obtained. The color purity is green. Further, as a result of continuously irradiating light from the blue LED element at room temperature, the time during which the luminance was decreased by 5% was 105 hours. The evaluation results of the first embodiment, the components (A) and (C) are shown in Table 2 to be described later.

(Examples 2 to 8 and Comparative Examples 1 to 6) In Examples 2 to 8 of the present invention and Comparative Examples 1 to 6 of the present invention, the conditions described in Table 2 were used. The organic light-emitting material (compound G-1, compound G-2, compound G-3, and compound G-4) is used as the component (A), and the amine derivative (compound Q-1, compound Q) shown in Table 2 is suitably used. A color conversion film was produced and evaluated in the same manner as in Example 1 except that the compound Q-3, the compound Q-4, the compound Q-5, and the compound Q-6) were used as the component (C). The evaluation results of Examples 2 to 8 and Comparative Examples 1 to 6 are shown in Table 2.

(Example 9) In the ninth embodiment of the present invention, a two-component thermosetting epoxy-based acrylic resin is used as the component (B), and 0.08 parts by weight is mixed with 100 parts by weight of the component (B). The compound R-1 of the component (A), 0.5 part by weight of a curing agent, and 1.0 part by weight of the compound Q-1 as the component (C). Thereafter, the mixture was stirred at 300 rpm for 1 hour to prepare a color conversion composition.

Then, the color conversion composition was applied to an extended polyethylene terephthalic acid film (XG5P1 manufactured by Toray Advanced Materials Co., Ltd.) by a bar coating method, and then subjected to 5 minutes at 120 ° C. dry. Thereby, a coating layer having an average film thickness of 10 μm was formed. Thereafter, a diffusion film ("Texcell" (registered trademark) TDF127 manufactured by Toray Advanced Materials Co., Ltd.) was laminated on the coating layer, and then aged at 60 ° C for 1 hour. A color conversion film was obtained.

As a result of color conversion of the blue LED light by the color conversion film, if only the light-emitting region of the red light is selected, a peak wavelength of 635 nm and a half-width of the emission spectrum in the peak wavelength of 49 nm can be obtained. The color purity is red. Further, as a result of continuously irradiating light from the blue LED element at room temperature, the time during which the luminance was decreased by 2% was 400 hours. The evaluation results of Example 9, the components (A) and (C) are shown in Table 3 which will be described later.

(Examples 10 to 15 and Comparative Examples 7 to 10) In Examples 10 to 15 of the present invention and Comparative Examples 7 to 10 of the present invention, the contents described in Table 3 were used. The organic light-emitting material (compound R-1, compound R-2, and compound R-3) is used as the component (A), and the amine derivative described in Table 3 (compound Q-1, compound Q-2, compound Q) is suitably used. A color conversion film was produced and evaluated in the same manner as in Example 9 except that the compound Q-4, the compound Q-5, and the compound Q-6) were used as the component (C). The evaluation results of Examples 10 to 15 and Comparative Examples 7 to 10 are shown in Table 3.

(Example 16) In Example 16 of the present invention, a two-component thermosetting epoxy-based acrylic resin was used as the component (B), and 0.20 part by weight was mixed with 100 parts by weight of the component (B). Compound G-1 of the light-emitting material (a) of the component (A), 0.08 parts by weight of the compound R-1 as the light-emitting material (b) of the component (A), 0.5 part by weight of a curing agent, and 1.0 part by weight of ( Compound Q-1 of component C). Thereafter, the mixture was stirred at 300 rpm for 1 hour to prepare a color conversion composition.

Then, the color conversion composition was applied onto a stretched polyethylene terephthalate film (XG5P1 manufactured by Toray Advanced Materials Co., Ltd.) by a bar coating method, and then dried at 120 ° C for 5 minutes. Thereby, a coating layer having an average film thickness of 10 μm was formed. Thereafter, a diffusion film ("Texcell" (registered trademark) TDF127 manufactured by Toray Advanced Materials Co., Ltd.) was laminated on the coating layer, and then aged at 60 ° C for 1 hour. A color conversion film was obtained.

As a result of color conversion of the blue LED light by the color conversion film, if only the light-emitting region of the green light is selected, the peak wavelength is 527 nm, and the half-width of the emission spectrum in the peak wavelength is 28 nm. The color purity is green, and if only the light-emitting region of red light is selected, a high-color purity red light having a peak wavelength of 635 nm and a half-width of the light-emitting spectrum in the peak wavelength of 49 nm can be obtained. Further, as a result of continuously irradiating light from the blue LED element at room temperature, the time during which the luminance was decreased by 5% was 110 hours. The evaluation results of Example 16, the components (A) and (C) are shown in Table 4 which will be described later.

(Examples 17 to 21, Comparative Example 11, and Comparative Example 12) In Examples 17 to 21 of the present invention and Comparative Example 11 and Comparative Example 12 of the present invention, the results described in Table 4 were used. The luminescent material (a) (compound G-1, compound G-2, compound G-3, compound G-4) and the luminescent material (b) (compound R-1, compound R-2, compound R-3) are used as A color conversion film was produced in the same manner as in Example 16 except that the amine derivative (Compound Q-1, Compound Q-6) described in Table 4 was used as the component (C). Conduct an evaluation. The evaluation results of Examples 17 to 21, Comparative Example 11, and Comparative Example 12 are shown in Table 4.

(Example 22) In Example 22 of the present invention, an acrylic resin "KC-7000" (manufactured by Kyoeisha Chemical Co., Ltd.) was used as the component (B), and 100 parts by weight of the component (B) was used. 0.25 parts by weight of the compound G-5 as the component (A) and 1.0 part by weight of the compound Q-1 as the component (C) were mixed. Thereafter, the mixture was stirred at 300 rpm for 1 hour to prepare a color conversion composition.

Then, the color conversion composition was applied onto a polyethylene terephthalate film (U48 manufactured by Toray Industries, Inc.) by a bar coating method, and then dried at 120 ° C for 5 minutes. Thereby, a color conversion layer having an average film thickness of 16 μm was formed. Thereafter, a diffusion film ("Texcell" (registered trademark) TDF127 manufactured by Toray Advanced Materials Co., Ltd.) was laminated on the coating layer, and then aged at 60 ° C for 1 hour. A color conversion film was obtained.

As a result of color conversion of the blue LED light by the color conversion film, if only the light-emitting region of the green light is selected, the peak wavelength is 529 nm, and the half-width of the emission spectrum in the peak wavelength is 26 nm. The color purity is green. The luminescence intensity in the peak wavelength of Example 22 is a relative value when the luminescence intensity in Comparative Example 13 to be described later is 1.00. Specifically, in Example 22, the luminescence intensity in the peak wavelength was 1.00, and the hindrance of luminescence caused by the component (C) was not observed. Further, as a result of continuously irradiating light from the blue LED element at room temperature, the time during which the luminance was decreased by 5% was 260 hours. The evaluation results of Example 22, the components (A) and (C) are shown in Table 5 to be described later.

(Examples 23 to 25, Comparative Example 13, and Comparative Example 14) In Examples 23 to 25 of the present invention and Comparative Example 13 and Comparative Example 14 of the present invention, the results described in Table 5 were used. The organic light-emitting material (compound G-5, compound G-6) is used as the component (A), and the amine derivative (compound Q-1, compound Q-2) described in Table 5 is suitably used as the component (C). A color conversion film was produced and evaluated in the same manner as in Example 22 except for the above. The evaluation results of Examples 23 to 25, Comparative Example 13, and Comparative Example 14 are shown in Table 5. However, the luminescence intensity (relative value) in Table 5 is a relative value when the luminescence intensity in Comparative Example 13 was 1.00.

[Table 2] (Table 2)

[Table 3] (Table 3)

[Table 4] (Table 4)

[Table 5] (Table 5) [Industrial availability]

As described above, the color conversion composition, the color conversion film, the light source unit including the same, the display, and the illumination device of the present invention are useful for enhancing the color reproducibility and high durability, and are particularly suitable for high-color purity illumination and A color conversion composition, a color conversion film, a light source unit including the same, a display, and a lighting device with high durability.

1‧‧‧Color conversion film
10‧‧‧Substrate layer
11‧‧‧Color conversion layer
12‧‧‧Block film

Fig. 1 is a schematic cross-sectional view showing an example of a color conversion film according to an embodiment of the present invention. Fig. 2 is a schematic cross-sectional view showing another example of the color conversion film according to the embodiment of the present invention. 3 is a schematic cross-sectional view showing still another example of the color conversion film according to the embodiment of the present invention. 4 is a view illustrating an absorption spectrum of a compound of Synthesis Example 1 in Examples of the present invention. Fig. 5 is a graph illustrating the luminescence spectrum of the compound of Synthesis Example 1 in the examples of the present invention. Fig. 6 is a graph illustrating the absorption spectrum of the compound of Synthesis Example 2 in the examples of the present invention. Fig. 7 is a view showing the luminescence spectrum of the compound of Synthesis Example 2 in the Example of the present invention.

1‧‧‧Color conversion film

10‧‧‧Substrate layer

11‧‧‧Color conversion layer

Claims (20)

A color conversion composition that converts incident light into light having a longer wavelength than the incident light, and includes: (A) component, (B) component, and (C) component, and (A) component: at least Organic light-emitting material (B) component: binder resin (C) component: amine derivative having a partial structure represented by the general formula (1) In the formula (1), R ¹⁰ to R ¹⁴ may be the same or different and selected from a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a heteroaryl group; wherein at least R ¹¹ and R ¹² are at least One and at least one of R ¹³ and R ¹⁴ are not a hydrogen atom. The color conversion composition according to claim 1, wherein the component (C) is a compound having a piperidine skeleton represented by the formula (2), In the formula (2), R ¹⁰ to R ¹⁴ are the same as those in the above formula (1). The color conversion composition according to Item 1 or 2, wherein the component (C) is a compound represented by the formula (3), In the formula (3), R ¹⁰ to R ¹⁴ are the same as the above formula (1); m is a natural number of 10 or less; Y is a single bond, a chain or a cyclic aliphatic hydrocarbon, or an aliphatic heterocyclic ring; An aromatic hydrocarbon ring, an aromatic hetero ring, or a combination of these is selected. The color conversion composition according to claim 3, wherein Y of the formula (3) is a chain or cyclic aliphatic hydrocarbon, a benzene ring, or a combination thereof. The color conversion composition according to claim 1 or 2, wherein the R ¹⁰ is an alkyl group. The color conversion composition according to Item 1 or 2, wherein the content of the component (C) is 1.0 × 10 ^-2 parts by weight or more based on 100 parts by weight of the component (B). 10 parts by weight or less. The color conversion composition according to the first or second aspect of the invention, wherein the component (A) contains a compound represented by the formula (4), In the formula (4), X is CR ⁷ or N; and R ¹ to R ⁹ may be the same or different, and may be different from hydrogen, alkyl, cycloalkyl, heterocyclic, alkenyl, cycloalkenyl or alkynyl. , hydroxy, thiol, alkoxy, alkylthio, aryl ether, aryl sulfide, aryl, heteroaryl, halogen, cyano, aldehyde, carbonyl, carboxyl, oxycarbonyl, amine formazan A condensed ring and an aliphatic ring formed between a group, an amine group, a nitro group, a decyl group, a decyloxy group, a boron boron group, a phosphine oxide group, and a contiguous substituent are selected. The color conversion composition according to claim ⁷ , wherein X of the general formula (4) is CR ⁷ , and the R ⁷ is a group represented by the general formula (5). In the formula (5), r is selected from hydrogen, alkyl, cycloalkyl, heterocyclic, alkenyl, cycloalkenyl, alkynyl, hydroxy, thiol, alkoxy, alkylthio, aryl ether , aryl sulfide group, aryl group, heteroaryl group, halogen, cyano group, aldehyde group, carbonyl group, carboxyl group, oxycarbonyl group, amine methyl group, amine group, nitro group, decyl group, decyloxy group, boron boron a group consisting of a phosphine oxide group; k is an integer of 1-3; and when k is 2 or more, r may be the same or different. The color conversion composition according to claim 7, wherein R ¹ , R ³ , R ⁴ and R ^{6 of} the formula (4) are respectively the same or different, and are substituted or not. Substituted phenyl. The color conversion composition according to claim 7, wherein R ¹ , R ³ , R ⁴ and R ^{6 of} the formula (4) are respectively the same or different, and are substituted or not. Substituted alkyl. The color conversion composition according to the first or second aspect of the invention, wherein the component (A) contains excitation light in a range of 430 nm or more and 500 nm or less, and the peak wavelength is Luminescent luminescent materials observed in regions above 500 nm and below 580 nm. The color conversion composition according to claim 1 or 2, wherein the component (A) comprises the following luminescent material (a) and luminescent material (b), and the luminescent material (a): by using Luminescent material luminescent material (b) exhibiting luminescence in a region having a peak wavelength of 500 nm or more and 580 nm or less at a wavelength of 430 nm or more and 500 nm or less: by a wavelength of 430 nm or more At least one of excitation light in a range of 500 nm or less and luminescence from the luminescent material (a) is excited, thereby exhibiting luminescence observed in a region having a peak wavelength of 580 nm or more and 750 nm or less. Luminescent material. The color conversion composition according to claim 12, wherein the content w _a of the luminescent material (a) and the content w _b of the luminescent material (b) are w _a ≧ w _b . The color conversion composition according to claim 7, wherein the component (A) contains excitation light having a wavelength of 430 nm or more and 500 nm or less, and exhibits a peak wavelength of 500 nm or more and 580. A light-emitting luminescent material of nm or less, and the luminescent material is a compound represented by the above formula (4). The color conversion composition according to claim 7, wherein the component (A) comprises the following luminescent material (a) and luminescent material (b), and the luminescent material (b) is The compound represented by the formula (4), the luminescent material (a): is observed in a region having a peak wavelength of 500 nm or more and 580 nm or less by using excitation light having a wavelength of 430 nm or more and 500 nm or less. The emitted luminescent material luminescent material (b) is excited by at least one of excitation light having a wavelength of 430 nm or more and 500 nm or less and luminescence from the luminescent material (a), thereby being expressed by A luminescent material having a peak wavelength of 580 nm or more and 750 nm or less. A color conversion film comprising a cured product of a color conversion composition containing the following (A) component, (B) component, and (C) component and converting incident light into light having a longer wavelength than the incident light; Layer, component (A): at least one organic light-emitting material (B) component: binder resin (C) component: amine derivative having a partial structure represented by the general formula (1) In the formula (1), R ¹⁰ to R ¹⁴ may be the same or different and selected from a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a heteroaryl group; wherein at least R ¹¹ and R ¹² are at least One and at least one of R ¹³ and R ¹⁴ are not a hydrogen atom. A light source unit comprising: a light source; and a color conversion film including the following components (A), (B), and (C), and converting incident light into light having a longer wavelength than the incident light (A) component: at least one organic light-emitting material (B) component: binder resin (C) component: an amine derivative having a partial structure represented by the general formula (1) In the formula (1), R ¹⁰ to R ¹⁴ may be the same or different and selected from a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a heteroaryl group; wherein at least R ¹¹ and R ¹² are at least One and at least one of R ¹³ and R ¹⁴ are not a hydrogen atom. The light source unit according to claim 17, wherein the light source is a light-emitting diode having a maximum light emission in a wavelength range of 430 nm or more and 500 nm or less. A display comprising a light source unit, the light source unit comprising: a light source; and a color conversion film comprising the following components (A), (B), and (C), and converting the incident light into a wavelength ratio a hardened material layer of the color conversion composition of the light having a long incident light; (A) component: at least one organic light-emitting material (B) component: a binder resin (C) component: having a formula (1) Partial structure of amine derivatives In the formula (1), R ¹⁰ to R ¹⁴ may be the same or different and selected from a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a heteroaryl group; wherein at least R ¹¹ and R ¹² are at least One and at least one of R ¹³ and R ¹⁴ are not a hydrogen atom. A lighting device characterized by comprising a light source unit, the light source unit comprising: a light source; and a color conversion film comprising the following components (A), (B) and (C), and converting the incident light into a wavelength a cured layer of a color conversion composition of light longer than the incident light; (A) component: at least one organic light-emitting material (B) component: binder resin (C) component: having a formula (1) Partial structure of amine derivatives In the formula (1), R ¹⁰ to R ¹⁴ may be the same or different and selected from a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a heteroaryl group; wherein at least R ¹¹ and R ¹² are at least One and at least one of R ¹³ and R ¹⁴ are not a hydrogen atom.