Color conversion composition, cured product, color conversion member, light source unit, display, and lighting device including same, and pyrromethene boron complex

Abstract

Provided is a color conversion member that achieves both high color purity light emission and high light emission efficiency. This color conversion composition comprises at least one light-emitting material and a binder resin. The at least one light-emitting material contains a compound having a structure represented by general formula (1).

Description

Color conversion composition, cured product, color conversion member, light source unit containing the same, display and lighting device, and pyrometenboron complex

[0001] The present invention relates to a color conversion composition, a cured product, a color conversion member, a light source unit containing the same, a display and an illumination device, and a pyrometenboron complex.

[0002] There is much research into applying multi-color technology using color conversion methods to liquid crystal displays, organic EL displays, lighting devices, and other applications. Color conversion refers to the process of converting light emitted from a light source into longer wavelength light, such as converting blue light to green or red light.

[0003] By forming this color-converting composition into a sheet and combining it with, for example, a blue light source, it becomes possible to obtain the three primary colors—blue, green, and red—from the blue light source, i.e., to obtain white light. This white light source, which combines a blue light source with a color-converting sheet, can be used as a light source unit such as a backlight unit. By combining this light source unit with a liquid crystal drive unit and a color filter, it becomes possible to manufacture a full-color display. Furthermore, the white light source, which combines a blue light source with a color-converting sheet, can also be used as a white light source such as LED lighting.

[0004] One of the challenges of displays utilizing color conversion methods is improving color reproducibility and durability. To improve color reproducibility, it is effective to narrow the full width at half maximum of the blue, green, and red emission spectra of the light source unit and increase the color purity of each color. As a means of solving this, for example, color conversion materials containing organic fluorescent materials have been proposed (see, for example, Patent Documents 1 and 2). Furthermore, as techniques for improving durability, techniques such as adding light stabilizers (see, for example, Patent Document 3) and techniques for improving durability with oxygen barriers (see, for example, Patent Document 4) have been proposed.

[0005] Japanese Patent Publication No. 2010-61824, Japanese Patent Publication No. 2014-136771, Japanese Patent Publication No. 2019-50381, International Publication No. 2017 / 057287

[0006] According to the techniques described in Patent Documents 1 to 4, a color conversion composition excellent in color reproducibility and relatively excellent in durability can be obtained. However, in recent years, along with high definition such as 4K and 8K, high dynamic range (HDR), and high contrast achieved by local dimming, the illuminance required for light source units of displays has increased, and higher durability is also required for color conversion members.

[0007] The problem to be solved by the present invention is to achieve both improved color reproducibility and high luminance in a color conversion member used for displays and lighting devices, and in order to achieve these, an object of the present invention is to provide a color conversion member that achieves both particularly high-purity color light emission and high luminous efficiency.

[0008] In order to solve the above-described problems and achieve the object, the present invention has a configuration described in any one of the following. [1] A color conversion composition comprising at least one light-emitting material and a binder resin, wherein the at least one light-emitting material contains a compound having a structure represented by general formula (1).

[0009]

[0010] (In general formula (1), X is C-R ７ or N. R １ to R ７ may each be the same or different, and are selected from the group consisting of a hydrogen atom, 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, an aryl thioether group, an aryl group, a heteroaryl group, halogen, a cyano group, an aldehyde group, a carboxyl group, an ester group, an amide group, an acyl group, a sulfonyl group, a sulfonic acid ester group, a sulfonamide group, a nitro group, a silyl group, a siloxanyl group, a boryl group, and a phosphine oxide group. R １ and R ２ and R ２ and R ３ one of the two pairs may be a ring structure represented by the following general formula (4). R １ to R ７At least one of them is a group represented by the following general formula (2): R ８ and R ９ These groups may be the same or different, and are selected from the group consisting of alkyl groups, cycloalkyl groups, heterocyclic groups, alkenyl groups, cycloalkenyl groups, alkynyl groups, hydroxyl groups, thiol groups, alkoxy groups, alkylthio groups, aryl ether groups, arylthioether groups, aryl groups, heteroaryl groups, halogens, and cyano groups.

[0011]

[0012] (In general formula (2), X １０１ ~X １０４ These may be the same or different, C-R １０１ Or it is N. １０１ is a hydrogen atom or substituent. Adjacent substituents may have a ring structure. * indicates a linkage to the pyromethene skeleton.

[0013]

[0014] (In general formula (4), R ２０１ and R ２０２ These may be the same or different, and are selected from the group consisting of hydrogen atoms, alkyl groups, cycloalkyl groups, heterocyclic groups, alkenyl groups, cycloalkenyl groups, alkynyl groups, hydroxyl groups, thiol groups, alkoxy groups, alkylthio groups, aryl ether groups, arylthioether groups, aryl groups, heteroaryl groups, halogens, cyano groups, aldehyde groups, carboxyl groups, ester groups, amide groups, acyl groups, sulfonyl groups, sulfonic acid ester groups, sulfonamide groups, nitro groups, silyl groups, siloxanyl groups, boryl groups, and phosphine oxide groups. Ar is a substituted or unsubstituted aromatic hydrocarbon ring, or a substituted or unsubstituted aromatic heterocycle. Also, R ２０１ and R ２０２ This may form a ring. * indicates a connection with the pyromethene skeleton.) [2] X in the general formula (2) １０１ ~X １０４ At least one of them is CR １０１ And R １０１The color conversion composition according to [1], wherein R in the general formula (2) is an electron-withdrawing group. [3] １０１ The color conversion composition according to [2], wherein X is a fluorine atom, a fluorine-containing aryl group, a fluorine-containing heteroaryl group, a fluorine-containing alkyl group, a substituted or unsubstituted acyl group, a substituted or unsubstituted ester group, a substituted or unsubstituted amide group, a substituted or unsubstituted sulfonyl group, or a cyano group. [4] In the general formula (2), X １０１ ~X １０４ The color conversion composition according to [1], wherein one of them is N. [5] In the general formula (2), X １０１ If N and X １０３ CR １０１ The color conversion composition according to any one of [1] to [4]. [6] In the general formula (2), X １０１ If N and X １０２ and X １０３ CR １０１ The color conversion composition according to any one of [1] to [5]. [7] In the general formula (1), R ３ and R ６ A color conversion composition according to any one of [1] to [6], wherein at least one of the groups is represented by the general formula (2) [8] R in the general formula (1) ８ and R ９ A color conversion composition according to any one of [1] to [7], wherein at least one of the atoms is a fluorine atom. [9] A color conversion composition according to any one of [1] to [8], wherein the light-emitting material exhibits emission observed in the region of 580 nm or more and less than 750 nm when excitation light is used.

[10] A cured product of the color conversion composition according to any one of [1] to [9].

[11] A color conversion member comprising the color conversion composition according to any one of [1] to [9] or its cured product.

[12] A light source unit comprising a light source and the color conversion member according to

[11] .

[13] A display comprising the light source unit according to

[12] .

[14] A lighting device comprising the light source unit according to

[12] .

[15] A pyrometenboron complex represented by the following general formula (3).

[0015]

[0016] (In general formula (3), X is C-R７ Or it is N. １ ~R ７ These may be the same or different, and are selected from the group consisting of hydrogen atoms, alkyl groups, cycloalkyl groups, heterocyclic groups, alkenyl groups, cycloalkenyl groups, alkynyl groups, hydroxyl groups, thiol groups, alkoxy groups, alkylthio groups, aryl ether groups, arylthioether groups, aryl groups, heteroaryl groups, halogens, cyano groups, aldehyde groups, carboxyl groups, ester groups, amide groups, acyl groups, sulfonyl groups, sulfonic acid ester groups, sulfonamide groups, nitro groups, silyl groups, siloxanyl groups, boryl groups, and phosphine oxide groups. １ and R ２ and R ２ and R ３ One of the two sets is a ring structure represented by the following general formula (4). ４ ~R ７ At least one of them is a group represented by the following general formula (5): R ８ and R ９ These groups may be the same or different, and are selected from the group consisting of alkyl groups, cycloalkyl groups, heterocyclic groups, alkenyl groups, cycloalkenyl groups, alkynyl groups, hydroxyl groups, thiol groups, alkoxy groups, alkylthio groups, aryl ether groups, arylthioether groups, aryl groups, heteroaryl groups, halogens, and cyano groups.

[0017]

[0018] (In general formula (4), R ２０１ and R ２０２These may be the same or different, and are selected from the group consisting of hydrogen atoms, alkyl groups, cycloalkyl groups, heterocyclic groups, alkenyl groups, cycloalkenyl groups, alkynyl groups, hydroxyl groups, thiol groups, alkoxy groups, alkylthio groups, aryl ether groups, arylthioether groups, aryl groups, heteroaryl groups, halogens, cyano groups, aldehyde groups, carboxyl groups, ester groups, amide groups, acyl groups, sulfonyl groups, sulfonic acid ester groups, sulfonamide groups, nitro groups, silyl groups, siloxanyl groups, boryl groups, and phosphine oxide groups. Ar is a substituted or unsubstituted aromatic hydrocarbon ring, or a substituted or unsubstituted aromatic heterocycle. Also, R ２０１ and R ２０２ This may form a ring. (* indicates the connection point with the pyromethene skeleton.)

[0019]

[0020] (In general formula (5), X １０１ ~X １０４ These may be the same or different, C-R １０１ Or it is N. １０１ R is a hydrogen atom or substituent. Adjacent substituents may have a ring structure. * indicates a linkage with the pyromethene skeleton.)

[16] In the above general formula (3), R ６ The pyrometenboron complex according to

[15] , wherein is the group represented by the general formula (5).

[17] The pyrometenboron complex according to

[15] or

[16] , wherein Ar in the general formula (4) is a substituted or unsubstituted benzene ring.

[18] The pyrometenboron complex according to

[15] or

[16] , wherein X in the general formula (5) １０１ ~X １０４ The pyrometenboron complex according to any one of

[15] to

[17] , wherein at least one of them is N.

[19] R in the general formula (3) ４ However, R is a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, and ６ A pyrometenboron complex according to any one of

[15] to

[18] , wherein R is a group represented by the general formula (5).

[20] In the general formula (3), ８ and R ９A pyrometenboron complex according to any one of

[15] to

[19] , wherein at least one of the atoms is a fluorine atom.

[21] A pyrometenboron complex according to any one of

[15] to

[20] , which exhibits emission observed in the region of 580 nm to less than 750 nm when excitation light is used.

[0021] The color conversion composition of the present invention and the color conversion member using the same achieve both high color purity emission and high luminous efficiency, making it possible to achieve both high color reproducibility and high brightness.

[0022] A schematic cross-sectional view showing an example of the color conversion member of the present invention.

[0023] The embodiments of the present invention will be described in detail below, but the present invention is not limited to the embodiments described below and can be modified in various ways depending on the purpose and application. Furthermore, matters listed as preferred examples in a particular embodiment or embodiment can also be applied to other embodiments or embodiments.

[0024] <Luminescent Material> The color conversion composition according to the embodiment of the present invention includes at least one luminescent material. Here, the luminescent material in the present invention refers to a material that emits light of a different wavelength from the light when irradiated with some light.

[0025] Examples of luminescent materials include inorganic phosphors, fluorescent pigments, fluorescent dyes, and quantum dots. Two or more of these may be included. To achieve highly efficient color conversion, materials exhibiting high quantum yield luminescence characteristics are preferred, and quantum dots and organic luminescent materials are preferred. Furthermore, from the viewpoint of dispersion uniformity, reduction in usage, and reduction of environmental impact, the use of organic luminescent materials is even more preferred.

[0026] Examples of organic luminescent materials include compounds having condensed aryl rings such as naphthalene, anthracene, phenanthrene, pyrene, chrysene, naphthalene, triphenylene, perylene, fluorantene, fluorene, and indene, as well as their derivatives; furan, pyrrole, thiophene, silole, 9-silafluorene, 9,9'-spirobicilafluorene, benzothiophene, benzofuran, indole, dibenzothiophene, dibenzofuran, imidazopyridine, phenanthroline, pyridine, pyrazol Compounds having heteroaryl rings such as din, naphthyridine, quinoxaline, and pyrrolopyridine, and their derivatives; borane derivatives; stilbene derivatives such as 1,4-distyrylbenzene, 4,4'-bis(2-(4-diphenylaminophenyl)ethenyl)biphenyl, and 4,4'-bis(N-(stilbene-4-yl)-N-phenylamino)stilbene; aromatic acetylene derivatives, tetraphenylbutadiene derivatives, aldazine derivatives, pyromethene derivatives, diketopyrrolo[3,4-c]pyro Coumarin derivatives; coumarin derivatives such as coumarin 6, coumarin 7, and coumarin 153; azole derivatives such as imidazole, thiazole, thiadiazole, carbazole, oxazole, oxadiazole, and triazole, and their metal complexes; cyanine compounds such as indocyanine green; xanthene compounds such as fluorescein, eosin, and rhodamine, and thioxanthene compounds; polyphenylene compounds, naphthalimide derivatives, phthalocyanine derivatives, and their metal complexes, porphyri Suitable examples include amine derivatives and their metal complexes; oxazine compounds such as Nile Red and Nile Blue; helicene compounds; aromatic amine derivatives such as N,N'-diphenyl-N,N'-di(3-methylphenyl)-4,4'-diphenyl-1,1'-diamine; and organometallic complex compounds such as iridium (Ir), ruthenium (Ru), rhodium (Rh), palladium (Pd), platinum (Pt), osmium (Os), europium (Eu), and rhenium (Re).

[0027] The organic light-emitting material may be either a fluorescent material or a phosphorescent material, but a fluorescent material is preferred in order to achieve high color purity.

[0028] As mentioned above, in order to improve color reproduction, it is preferable that the full width at half maximum of the emission spectra of each color (blue, green, and red) be small. Therefore, it is preferable that the full width at half maximum of the emission spectrum at the emission peak wavelength of the light-emitting material be 50 nm or less, and more preferably 40 nm or less.

[0029] In the color conversion composition according to an embodiment of the present invention, the light-emitting material contains a compound having a structure represented by general formula (1).

[0030]

[0031] In general formula (1), X is C-R ７ Or it is N. １ ~R ７ These may be the same or different, and are selected from the group consisting of hydrogen atoms, alkyl groups, cycloalkyl groups, heterocyclic groups, alkenyl groups, cycloalkenyl groups, alkynyl groups, hydroxyl groups, thiol groups, alkoxy groups, alkylthio groups, aryl ether groups, arylthioether groups, aryl groups, heteroaryl groups, halogens, cyano groups, aldehyde groups, carboxyl groups, ester groups, amide groups, acyl groups, sulfonyl groups, sulfonic acid ester groups, sulfonamide groups, nitro groups, silyl groups, siloxanyl groups, boryl groups, and phosphine oxide groups. １ and R ２ and R ２ and R ３ One of the two sets may be a ring structure represented by the following general formula (4). １ ~R ７ At least one of them is a group represented by the following general formula (2): R ８ and R ９ These may be the same or different, and are selected from the group consisting of alkyl groups, cycloalkyl groups, heterocyclic groups, alkenyl groups, cycloalkenyl groups, alkynyl groups, hydroxyl groups, thiol groups, alkoxy groups, alkylthio groups, aryl ether groups, arylthioether groups, aryl groups, heteroaryl groups, halogens, and cyano groups.

[0032]

[0033] In general formula (2), X１０１ ~X １０４ These may be the same or different, C-R １０１ Or it is N. １０１ is a hydrogen atom or substituent. Adjacent substituents may have a ring structure. * indicates a linkage with the pyromethene skeleton.

[0034]

[0035] In general formula (4), R ２０１ and R ２０２ These may be the same or different, and are selected from the group consisting of hydrogen atoms, alkyl groups, cycloalkyl groups, heterocyclic groups, alkenyl groups, cycloalkenyl groups, alkynyl groups, hydroxyl groups, thiol groups, alkoxy groups, alkylthio groups, aryl ether groups, arylthioether groups, aryl groups, heteroaryl groups, halogens, cyano groups, aldehyde groups, carboxyl groups, ester groups, amide groups, acyl groups, sulfonyl groups, sulfonic acid ester groups, sulfonamide groups, nitro groups, silyl groups, siloxanyl groups, boryl groups, and phosphine oxide groups. Ar is a substituted or unsubstituted aromatic hydrocarbon ring, or a substituted or unsubstituted aromatic heterocycle. Also, R ２０１ and R ２０２ This may form a ring. * indicates the connection to the pyromethene skeleton.

[0036] In all of the above groups, hydrogen may be replaced with deuterium. The same applies to the compounds or substructures described below.

[0037] Furthermore, in the following explanation, for example, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms refers to an aryl group whose total carbon number, including the carbon atoms in the substituents substituted on the aryl group, is 6 to 40. The same applies to other substituents that specify the number of carbon atoms.

[0038] In the phrase "substituted or unsubstituted," "unsubstituted" means that a hydrogen atom or a deuterium atom has been substituted. The same applies to the phrase "substituted or unsubstituted" in the compounds or substructures described below.

[0039] In all of the above groups, possible substituents include alkyl groups, cycloalkyl groups, heterocyclic groups, alkenyl groups, cycloalkenyl groups, alkynyl groups, aryl groups, heteroaryl groups, hydroxyl groups, thiol groups, alkoxy groups, alkylthio groups, aryl ether groups, arylthioether groups, halogens, cyano groups, aldehyde groups, carbonyl groups, carboxyl groups, oxycarbonyl groups, ester groups, carbamoyl groups, amide groups, sulfonyl groups, sulfonic acid ester groups, sulfonamide groups, imino groups, amino groups, nitro groups, silyl groups, siloxanyl groups, boryl groups, or phosphine oxide groups. Furthermore, these substituents may be further substituted with the substituents mentioned above.

[0040] Alkyl groups refer to saturated aliphatic hydrocarbon groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, and tert-butyl groups, and may or may not have substituents. There are no particular restrictions on additional substituents when substitution occurs; for example, alkyl groups, halogens, aryl groups, heteroaryl groups, etc., can be used, and this point is also common to the following description. Furthermore, the number of carbon atoms in the alkyl group is not particularly limited, but from the standpoint of availability and cost, it is preferably in the range of 1 to 20, more preferably 1 to 8.

[0041] A cycloalkyl group refers to a saturated alicyclic hydrocarbon group such as a cyclopropyl group, cyclohexyl group, norbornyl group, or adamantyl group, and may or may not have substituents. The number of carbon atoms in the alkyl group is not particularly limited, but is preferably in the range of 3 to 20.

[0042] A heterocyclic group refers to an aliphatic ring having atoms other than carbon within the ring, such as a pyran ring, a piperidine ring, or a cyclic amide, and may or may not have substituents. The number of carbon atoms in the heterocyclic group is not particularly limited, but is preferably in the range of 2 to 20.

[0043] An alkenyl group refers to an unsaturated aliphatic hydrocarbon group containing a double bond, such as a vinyl group, an allyl group, or a butadienyl group, and may or may not have substituents. The number of carbon atoms in the alkenyl group is not particularly limited, but is preferably in the range of 2 to 20.

[0044] A cycloalkenyl group refers to an unsaturated alicyclic hydrocarbon group containing a double bond, such as a cyclopentenyl group, cyclopentadienyl group, or cyclohexenyl group, which may or may not have substituents. The number of carbon atoms in the cycloalkenyl group is not particularly limited, but is preferably in the range of 3 to 20.

[0045] An alkynyl group refers to an unsaturated aliphatic hydrocarbon group containing a triple bond, such as an ethynyl group, and may or may not have substituents. The number of carbon atoms in the alkynyl group is not particularly limited, but is preferably in the range of 2 to 20.

[0046] An alkoxy group refers to a functional group in which an aliphatic hydrocarbon group is bonded via an ether linkage, such as a methoxy group, ethoxy group, or propoxy group. This aliphatic hydrocarbon group may or may not have substituents. The number of carbon atoms in the alkoxy group is not particularly limited, but is preferably in the range of 1 to 20.

[0047] An alkylthio group is a group in which the oxygen atom of the ether bond of an alkoxy group is replaced by a sulfur atom. The hydrocarbon group of the alkylthio group may or may not have substituents. The number of carbon atoms in the alkylthio group is not particularly limited, but is preferably in the range of 1 to 20.

[0048] An aryl ether group refers to 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 or may not have substituents. The number of carbon atoms in the aryl ether group is not particularly limited, but is preferably in the range of 6 to 40.

[0049] An arylthioether group is an aryl ether group in which the oxygen atom in the ether bond is replaced by a sulfur atom. The aromatic hydrocarbon group in the arylthioether group may or may not have substituents. The number of carbon atoms in the arylthioether group is not particularly limited, but is preferably in the range of 6 to 40.

[0050] The aryl group refers to aromatic hydrocarbon groups such as phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, benzophenanthryl, benzoanthracenyl, chrysenyl, pyrenyl, fluoranthenyl, triphenylenyl, benzofluoranthenyl, dibenzoanthracenyl, perilenyl, and hericenyl groups. Among these, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, pyrenyl, fluoranthenyl, and triphenylenyl groups are preferred. The aryl group may or may not have substituents. The number of carbon atoms in the aryl group is not particularly limited, but is preferably in the range of 6 to 40, more preferably 6 to 30.

[0051] Furthermore, preferred aryl groups are phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthryl, and anthracenyl groups, with phenyl, biphenyl, terphenyl, and naphthyl groups being more preferred. Even more preferred are phenyl, biphenyl, and terphenyl groups, with phenyl being particularly preferred.

[0052] When each substituent is further substituted with an aryl group, the aryl group is preferably a phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, phenanthryl group, or anthracenyl group, and more preferably a phenyl group, biphenyl group, terphenyl group, or naphthyl group. Particularly preferred is a phenyl group.

[0053] Heteroaryl groups include, for example, pyridyl, furanyl, thienyl, quinolinyl, isoquinolinyl, pyrazinyl, pyrimidyl, pyridadinyl, triazinyl, naphthilidinyl, synnolinyl, phthalazinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothienyl, indolyl, dibenzofuranyl, dibenzothienyl, carbazolyl, and benzocarbazolyl. This refers to cyclic aromatic groups having one or more non-carbon atoms in the ring, such as a carbonyl group, indrocarbazolyl group, benzoflocarbazolyl group, benzothienocarbazolyl group, dihydroindenocarbazolyl group, benzoquinolinyl group, acridinyl group, dibenzoacridinyl group, benzimidazolyl group, imidazopyridyl group, benzoxazolyl group, benzothiazolyl group, and phenanthrolinyl group. However, naphthilidinyl group refers to any of 1,5-naphthilidinyl group, 1,6-naphthilidinyl group, 1,7-naphthilidinyl group, 1,8-naphthilidinyl group, 2,6-naphthilidinyl group, or 2,7-naphthilidinyl group. Heteroaryl groups may or may not have substituents. The number of carbon atoms in the heteroaryl group is not particularly limited, but is preferably in the range of 2 to 40, more preferably 2 to 30.

[0054] Furthermore, preferred heteroaryl groups include pyridyl, furanyl, thienyl, quinolinyl, pyrimidyl, triazinyl, benzofuranyl, benzothienyl, indolyl, dibenzofuranyl, dibenzothienyl, carbazolyl, benzimidazolyl, imidazopyridyl, benzoxazolyl, benzothiazolyl, and phenanthrolinyl groups, with pyridyl, furanyl, thienyl, and quinolinyl groups being more preferred. Particularly preferred is the pyridyl group.

[0055] When each substituent is further substituted with a heteroaryl group, preferred examples of the heteroaryl group include pyridyl group, furanyl group, thienyl group, quinolinyl group, pyrimidyl group, triazinyl group, benzofuranyl group, benzothienyl group, indolyl group, dibenzofuranyl group, dibenzothienyl group, carbazolyl group, benzimidazolyl group, imidazopyridyl group, benzoxazolyl group, benzothiazolyl group, and phenanthrolinyl group, with pyridyl group, furanyl group, thienyl group, and quinolinyl group being more preferred. Pyridyl group is particularly preferred.

[0056] Halogen refers to an atom selected from fluorine, chlorine, bromine and iodine.

[0057] A carbonyl group, carboxy group, oxycarbonyl group, ester group, carbamoyl group, amide group, or imino group may or may not have a 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.

[0058] A sulfonyl group, a sulfonic acid ester group, and a sulfonamide group are respectively -S(=O) ２ R １０ , -S(=O) ２ OR １０ , -S(=O) ２ NR １０ R １１ which is a group represented by, and R １０ , R １１ is selected from hydrogen or the same group of substituents as mentioned above for the case of substitution.

[0059] An amino group is a substituted or unsubstituted amino group. Examples of the substituent in the case of substitution include an aryl group, a heteroaryl group, a linear alkyl group, and a branched alkyl group. Preferred examples of the aryl group and heteroaryl group include a phenyl group, a naphthyl group, a pyridyl group, and a quinolinyl group. These substituents may be further substituted. The number of carbon atoms is not particularly limited, but is preferably in the range of 2 to 50, more preferably 6 to 40, and particularly preferably 6 to 30.

[0060] The silyl group refers to alkylsilyl groups such as trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, propyldimethylsilyl, and vinyldimethylsilyl groups, as well as arylsilyl groups such as phenyldimethylsilyl, tert-butyldiphenylsilyl, triphenylsilyl, and trinaphthylsilyl groups. The substituents on silicon may be further substituted. The number of carbon atoms in the silyl group is not particularly limited, but is preferably in the range of 1 to 30.

[0061] A siloxanyl group refers to a silicon compound group via an ether bond, such as a trimethylsiloxanyl group. Substituents on the silicon may be further substituted.

[0062] A boryl group is a substituted or unsubstituted boryl group. Examples of substituents include aryl groups, heteroaryl groups, linear alkyl groups, branched alkyl groups, aryl ether groups, alkoxy groups, and hydroxyl groups, with aryl groups and aryl ether groups being preferred.

[0063] A phosphine oxide group is -P(=O)R １０ R １１ It is a group represented by R. １０ and R １１ This is selected from the same group as hydrogen atoms or substituents in the case of substitution described above.

[0064] Furthermore, any two adjacent substituents may bond to each other to form a conjugated or unconjugated fused ring. The constituent elements of the fused ring may include elements selected from nitrogen, oxygen, sulfur, phosphorus, and silicon, in addition to carbon. The fused ring may also condense with another ring.

[0065] Compounds having the structure represented by general formula (1) possess a pyrometenboron complex skeleton. Because the pyrometenboron complex skeleton is a robust and highly planar skeleton, it exhibits a high fluorescence quantum yield, and because the full width at half maximum of the emission spectrum at the peak emission wavelength is small, efficient color conversion and high color purity can be achieved.

[0066] Generally, when a BODIPY (boron-dipyrromethene) complex is used to emit light in a wavelength region longer than that of green light, conjugation of the BODIPY complex is extended by directly bonding a group having a double bond to the BODIPY complex skeleton, so as to shift the emission wavelength to a longer wavelength. However, if the group having a double bond is only simply bonded to the BODIPY complex skeleton, the BODIPY complex transforms into a plurality of stable structures in its excited state (this phenomenon is hereinafter referred to as "structural relaxation"), and thus is deactivated accompanied by light emission from various energy states. In this case, the emission spectrum becomes broad, the half-width increases, and the color purity decreases. That is, in order to achieve a longer emission wavelength using a BODIPY complex, ingenuity in molecular design is required.

[0067] The BODIPY complex used in the composition of the present invention is a compound having a structure represented by general formula (1), which has a substituent represented by general formula (2) on the BODIPY complex skeleton.

[0068] The substituent represented by general formula (2) is a nitrogen-containing 5-membered ring, and an interaction such as intramolecular hydrogen bonding occurs between the substituent and the BODIPY complex skeleton. This can suppress excessive structural relaxation in the excited state of the compound represented by general formula (1), thereby making the emission spectrum of the compound represented by general formula (1) sharp. When this compound is used as a light-emitting material, light emission with high color purity can be obtained. That is, when the compound represented by general formula (1) is used in a color conversion composition, a larger color gamut can be efficiently formed, and color reproducibility is improved. In addition, since intramolecular motion is suppressed, rigidity is improved, and luminous efficiency (luminance) can be improved.

[0069] In general formula (1), R １ to R ６ other than the group represented by general formula (1) may each be the same or different, and are preferably a hydrogen atom, an alkyl group, a cycloalkyl group, a heterocyclic group, an alkenyl group, an alkynyl group, a thiol group, an alkoxy group, an aryl group, a heteroaryl group, a halogen, a cyano group, an aldehyde group, a carboxyl group, an ester group, an amide group, an acyl group, a sulfonyl group, a nitro group, and a phosphine oxide group.

[0070] In general formula (1), R １ and R ２ The combination and R ２ and R ３ One of the two pairs, the pair and the other, may be a ring structure represented by general formula (4).

[0071] In general formula (4), Ar is preferably a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted phenanthrene ring, a substituted or unsubstituted pyridine ring, a substituted or unsubstituted pyrimidine ring, or a substituted or unsubstituted pyrazine ring. Furthermore, if Ar is a substituted or unsubstituted benzene ring, it is particularly preferred because it improves thermal and electrical stability. In other words, it is preferable that Ar in general formula (4) is a substituted or unsubstituted benzene ring.

[0072] In general formula (1), R ７ If it is a group other than the group represented by general formula (2), it is preferably the group represented by the following general formula (6).

[0073]

[0074] In general formula (6), r is selected from the group consisting of hydrogen atom, alkyl group, cycloalkyl group, heterocyclic group, alkenyl group, cycloalkenyl group, alkynyl group, hydroxyl group, thiol group, alkoxy group, alkylthio group, aryl ether group, arylthioether group, aryl group, heteroaryl group, halogen, cyano group, aldehyde group, carbonyl group, carboxyl group, oxycarbonyl group, carbamoyl group, amino group, nitro group, silyl group, siloxanyl group, boryl group, and phosphine oxide group. k is an integer from 1 to 3. If k is 2 or greater, r may be the same or different.

[0075] In general formula (6), r is selected from the group consisting of hydrogen atom, alkyl group, cycloalkyl group, heterocyclic group, alkenyl group, cycloalkenyl group, alkynyl group, hydroxyl group, thiol group, alkoxy group, alkylthio group, aryl ether group, arylthioether group, aryl group, heteroaryl group, halogen, cyano group, aldehyde group, carbonyl group, carboxyl group, oxycarbonyl group, carbamoyl group, amino group, nitro group, silyl group, siloxanyl group, boryl group, and phosphine oxide group. k is an integer from 1 to 3. If k is 2 or greater, r may be the same or different.

[0076] In general formula (6), r is preferably a substituted or unsubstituted aryl group. Among such aryl groups, phenyl and naphthyl groups are particularly preferred examples. When r is an aryl group, k in general formula (6) is preferably 1 or 2, and more preferably 2. Furthermore, at least one of r is preferably substituted with an alkyl group or an aryl group. In this case, methyl, ethyl, and tert-butyl groups are particularly preferred examples of alkyl groups. Also, when r is an aryl group, phenyl and naphthyl groups are preferred as aryl groups. These aryl groups may be further substituted with alkyl groups, heterocyclic groups, alkenyl groups, hydroxyl groups, alkoxy groups, aryl ether groups, aryl groups, heteroaryl groups, halogens, cyano groups, carboxyl groups, ester groups, oxycarbonyl groups, or alkoxy groups.

[0077] In general formula (2), R １０１ If the substituent is an alkyl group or an electron-withdrawing group, it is preferable that the substituent be an alkyl group or an electron-withdrawing group.

[0078] In general formula (2), X １０１ ~X １０４ At least one of them is CR １０１ And R １０１ It is preferable that the group is an electron-withdrawing group, from the viewpoint of further increasing the compound's durability against light.

[0079] Electron-withdrawing groups, also called electron-accepting groups, are groups of atoms in organic electron theory that attract electrons from the substituted atomic group through inductive or resonance effects. Examples of electron-withdrawing groups include those whose substituent constant (σp (para)) in Hammett's rule takes a positive value. The substituent constant (σp (para)) in Hammett's rule can be quoted from the Chemical Handbook, Basic Edition, 5th Revised Edition (II-380).

[0080] Examples of electron-withdrawing groups include -F (σp: +0.06), -Cl (σp: +0.23), -Br (σp: +0.23), -I (σp: +0.18), and -CO. ２ R １２ (σp:R １２ When it is an ethyl group, it is +0.45), -CONH ２ (σp: +0.38), -COR １２ (σp:R １２ When it is a methyl group, +0.49), -CF ３ (σp: +0.50), -SO ２ R １２ (σp:R １２ When it is a methyl group, it is +0.69), -NO ２ Examples include (σp: +0.81). １２ Each of these independently represents a hydrogen atom, a substituted or unsubstituted ring-forming aromatic hydrocarbon group with 6 to 30 carbon atoms, a substituted or unsubstituted heterocyclic group with 5 to 30 ring-forming atoms, a substituted or unsubstituted alkyl group with 1 to 30 carbon atoms, and a substituted or unsubstituted cycloalkyl group with 1 to 30 carbon atoms. Specific examples of each of these groups are the same as those given above.

[0081] In particular, R in general formula (2) １０１ However, it is more preferable that the group is a fluorine atom, a fluorine-containing aryl group, a fluorine-containing heteroaryl group, a fluorine-containing alkyl group, a substituted or unsubstituted acyl group, a substituted or unsubstituted ester group, a substituted or unsubstituted amide group, a substituted or unsubstituted sulfonyl group, or a cyano group. Furthermore, from the viewpoint of controlling fluorescence wavelength and absorption wavelength and improving compatibility with the solvent, R １０１ It is even more preferable that the group is a substituted or unsubstituted ester group or a halogen. Furthermore, from the viewpoint of suppressing free rotation and improving luminous efficiency, R１０１ It is even more preferable that the group is an aryl group having an electron-withdrawing group at the ortho position.

[0082] From the perspective of increasing the rigidity of the molecular skeleton and improving the skeletal stability of the compound, X １０１ ~X １０４ It is preferable that one of them is N. The X is the adjacent position that bonds to the pyrometenboron complex skeleton. １０１ ~X １０４ One of these atoms is N, which allows the substituent of general formula (2) to interact with the pyrometenboron complex skeleton.

[0083] From the perspective of increasing the rigidity of the molecular skeleton and improving the skeletal stability of the compound, X １０１ If N and X １０３ CR １０１ It is preferable that the X is at an adjacent position to the pyrometenboron complex skeleton. １０１ The fact that is N allows the substituent in general formula (2) to interact with the pyrometenboron complex skeleton. Also, from the standpoint of the difficulty of synthesis, the X in general formula (2) １０１ It is preferable that X in general formula (2) １０３ CR １０１ This is preferable because steric hindrance moderately reduces the planarity of the molecular skeleton, thereby improving its dispersibility in the binder resin.

[0084] Furthermore, from the perspective of the difficulty of synthesis, X １０１ N is N, and X in general formula (2) １０２ and X １０３ CR １０１ It is preferable that this be the case.

[0085] From the viewpoint of increasing the rigidity of the molecular skeleton and improving the skeletal stability of the compound, R in general formula (1) ３ and R ６ Preferably, at least one of the groups is a group represented by general formula (2).

[0086] In general formula (1), R ８ and R ９Preferably, at least one of them is a fluorine atom. This can lower the electron density of the pyrometenboron complex framework. X in general formula (2) １０４ When the relationship is C-H, the rigidity of the molecular skeleton increases, and from the viewpoint of increasing the skeletal stability of the compound, R in general formula (1) ８ and R ９ It is particularly preferable that at least one of them is a fluorine atom. Near the fluorine atom is X in general formula (2). １０４ When the interaction is C-H, it works efficiently, suppressing excessive structural relaxation in the excited state and resulting in emission with higher color purity.

[0087] Based on the above, the compound represented by general formula (1) has a group represented by general formula (2) in its pyrometenboron complex framework, which makes it possible to achieve both high color purity and high brightness. Furthermore, the compound represented by general formula (1) exhibits a high emission quantum yield and a small peak full width at half maximum of the emission spectrum, thus enabling efficient color conversion and high color purity.

[0088] Furthermore, compounds having the structure represented by general formula (1) can have various properties and physical characteristics such as luminescence efficiency, color purity, thermal stability, photostability, and dispersibility adjusted by introducing appropriate substituents at appropriate positions.

[0089] Examples of compounds having the structure represented by general formula (1) are shown below, but are not limited to these.

[0090]

[0091]

[0092] Compounds having the structure represented by general formula (1) include compounds in which some of the hydrogen atoms in these structures are substituted with substituted or unsubstituted alkyl groups, substituted or unsubstituted diphenylamino groups, substituted or unsubstituted carbazolyl groups, or substituted or unsubstituted phenyl groups. In particular, these compounds may be compounds in which some of the hydrogen atoms in these structures are substituted with tert-butyl groups, alkyl-substituted diphenylamino groups, alkyl-substituted carbazolyl groups, or alkyl-substituted phenyl groups.

[0093] Regarding the synthesis of pyrometenboron complexes, the compound represented by general formula (1) can be synthesized by referring to the methods described in J. Org. Chem., Vol. 64, No. 21, pp. 7813-7819 (1999), Angew. Chem., Int. Ed. Engl., vol. 36, pp. 1333-1335 (1997), etc. For example, one method involves heating the compound represented by general formula (6) and the compound represented by general formula (7) in 1,2-dichloroethane in the presence of phosphorus oxychloride, and then reacting the compound represented by general formula (8) in 1,2-dichloroethane in the presence of triethylamine to obtain the compound represented by general formula (1). However, the pyrometenboron complex used in the composition of the present invention is not limited to this. Here, R １ ~R 8 The explanation is the same as above. J represents halogen.

[0094]

[0095] Furthermore, when introducing aryl or heteroaryl groups, one method is to generate a carbon-carbon bond using a coupling reaction between a halogenated derivative and a boronic acid or boronic acid esterified derivative, but the pyrometenboron complex used in the composition of the present invention is not limited to this. Similarly, when introducing amino or carbazolyl groups, one method is to generate a carbon-nitrogen bond using a coupling reaction between a halogenated derivative and an amine or carbazole derivative under a metal catalyst such as palladium, but the pyrometenboron complex used in the composition of the present invention is not limited to this.

[0096] The pyrometenboron complex used in the composition of the present invention preferably exhibits emission observed in the region of peak wavelength between 580 nm and less than 750 nm when excited with excitation light. Hereafter, emission observed in the region of peak wavelength between 580 nm and less than 750 nm may be referred to as "red emission." Generally, the higher the energy of the excitation light, the more likely it is to cause decomposition of the luminescent material. However, excitation light in the wavelength range of 430 nm to 500 nm has a relatively low excitation energy. Therefore, red emission with good color purity can be obtained without causing decomposition of the luminescent material. As a method for measuring the fluorescence spectrum, one example is to dissolve the compound in an organic solvent such as toluene and measure the fluorescence spectrum when the compound is excited with excitation light in the wavelength range of 430 nm to 500 nm.

[0097] A color conversion composition according to an embodiment of the present invention is a color conversion composition that converts incident light into light with a longer wavelength than the incident light, and comprises a pyrometenboron complex used in the composition of the present invention and a binder resin. The color conversion composition of the present invention preferably includes (a) a light-emitting material that exhibits emission with a peak wavelength of 500 nm to less than 580 nm when excitation light in the wavelength range of 400 nm to 500 nm is used (hereinafter referred to as "light-emitting material (a)") or a light-emitting material that exhibits emission observed in the region of 580 nm to less than 750 nm when excitation light in the wavelength range of 400 nm to 500 nm is used (hereinafter referred to as "light-emitting material (b)"). Hereafter, emission observed in the region of 580 nm to less than 750 nm with a peak wavelength will be referred to as "red emission". Generally, the higher the energy of the excitation light, the more likely it is to cause decomposition of the material, but since excitation light in the wavelength range of 400 nm to 500 nm has a relatively small excitation energy, green emission with good color purity can be obtained without causing decomposition of the light-emitting material in the color conversion composition.

[0098] Furthermore, the color conversion composition according to the embodiment of the present invention preferably includes (a) a light-emitting material that exhibits emission with a peak wavelength of 500 nm to less than 580 nm when excited by excitation light in the wavelength range of 400 nm to 500 nm, and (b) a light-emitting material that exhibits emission observed in the region of 580 nm to 750 nm when excited by either or both excitation light in the wavelength range of 400 nm to 500 nm or emission from light-emitting material (a). Hereafter, emission observed in the region of 500 nm to 580 nm will be referred to as "green emission".

[0099] Since a portion of the excitation light in the wavelength range of 400 nm to 500 nm partially passes through the color conversion composition or color conversion member of the present invention, when a blue LED with a sharp emission peak is used, it exhibits a sharp emission spectrum in each of the blue, green, and red colors, and white light with good color purity can be obtained. As a result, especially in displays, a wider color gamut with more vivid colors can be efficiently created. Furthermore, in lighting applications, compared to white LEDs that combine blue LEDs and yellow phosphors, which are currently mainstream, the emission characteristics in the green and red regions are improved, resulting in improved color rendering and making it a desirable white light source.

[0100] Examples of the luminescent material (a) include coumarin derivatives such as coumarin 6, coumarin 7, and coumarin 153; cyanine derivatives such as indocyanine green; fluorescein derivatives such as fluorescein, fluorescein isothiocyanate, and carboxyfluorescein diacetate; phthalocyanine derivatives such as phthalocyanine green; perylene derivatives such as diisobutyl-4,10-dicyanoperylene-3,9-dicarboxylate; pyromethene derivatives; stilbene derivatives; oxazine derivatives; naphthalimide derivatives; pyrazine derivatives; benzimidazole derivatives; benzoxazole derivatives; benzothiazole derivatives; imidazopyridine derivatives; azole derivatives; compounds having a condensed aryl ring such as anthracene and their derivatives; aromatic amine derivatives; and organometallic complex compounds. Among these compounds, pyromethene derivatives are particularly preferred because they give a high fluorescence quantum yield and exhibit luminescence with high color purity. Two or more of these may be included.

[0101] Examples of luminescent materials (b) include cyanine derivatives such as 4-dicyanomethylene-2-methyl-6-(p-dimethylaminostyllyl)-4H-pyran, rhodamine derivatives such as rhodamine B, rhodamine 6G, rhodamine 101, and sulforhodamine 101, pyridine derivatives such as 1-ethyl-2-(4-(p-dimethylaminophenyl)-1,3-butadienyl)-pyridinium-perchlorate, perylene derivatives such as N,N'-bis(2,6-diisopropylphenyl)-1,6,7,12-tetraphenoxyperylene-3,4:9,10-bisdicarboimide, as well as porphyrin derivatives, pyromethene derivatives, oxazine derivatives, pyrazine derivatives, compounds having condensed aryl rings such as naphthacene and dibenzodiindenoperylene and their derivatives, and organometallic complex compounds. Compounds having the structure represented by the above-mentioned general formula (1) are also preferred because they exhibit luminescence with high color purity. Among these compounds, pyromethene derivatives are particularly suitable because they give a high fluorescence quantum yield and exhibit luminescence with high color purity. In particular, compounds having the structure represented by the general formula (1) described above are preferred because their durability is dramatically improved. Two or more of these may be included.

[0102] One embodiment of the color conversion composition according to the present invention is a compound having a structure represented by general formula (1) that is a light-emitting material exhibiting emission with a peak wavelength of 500 nm or more and less than 580 nm. In this case, high-purity green emission is obtained, and the color reproducibility in the green region is improved, which is preferable.

[0103] Another embodiment of the color conversion composition according to the embodiment of the present invention is a luminescent material in which the compound having the structure represented by general formula (1) exhibits luminescence with a peak wavelength of 580 nm or more and less than 750 nm. In this case, a red emission with high color purity is obtained, and the color reproducibility in the red region is improved, which is preferable.

[0104] As mentioned above, in order to improve color reproducibility, it is preferable that the full width at half maximum (FWHM) of the emission spectra of blue, green, and red be small, and in particular, small FWHMs of the emission spectra of green and red light are effective in improving color reproducibility. For example, the FWHM of the emission spectrum of luminescent material (a) is preferably 50 nm or less, more preferably 40 nm or less, even more preferably 35 nm or less, and particularly preferably 30 nm or less. The FWHM of the emission spectrum of luminescent material (b) is preferably 60 nm or less, more preferably 50 nm or less, even more preferably 40 nm or less, even more preferably 35 nm or less, and particularly preferably 30 nm or less.

[0105] The content of the luminescent material in the color conversion composition according to the embodiment of the present invention can be selected according to the molar extinction coefficient of the compound, the fluorescence quantum yield and absorption intensity at the excitation wavelength, and the thickness and transmittance of the film to be made. Here, the content of the luminescent material refers to the total content when two or more types of luminescent materials are included. The content of the luminescent material is 1.0 × 10⁶ per 100 parts by weight of the binder resin. －２ Parts by weight to 5 parts by weight are preferred.

[0106] Furthermore, when the color conversion composition contains both a light-emitting material (a) that emits green light and a light-emitting material (b) that emits red light, a portion of the green light is converted to red light, so the amount of the light-emitting material (a) w ａ And the content of the luminescent material (b) w ｂ But, lol ａ ≧w ｂ It is preferable that the relationship be such that the content ratio of each material is w ａ :w ｂ The ratio is preferably 200:1 to 3:1. However, w ａ and w ｂ This is a weight percentage relative to the weight of the binder resin.

[0107] The color conversion composition according to the embodiment of the present invention may contain, as necessary, other compounds in addition to the compounds exemplified above as luminescent materials. For example, an assist dopant may be included to increase the energy transfer efficiency from excitation light to the luminescent material. Furthermore, if it is desired to consider the emission color, the composition may further contain known luminescent materials such as the aforementioned organic luminescent materials, inorganic phosphors, fluorescent pigments, fluorescent dyes, and quantum dots.

[0108] Examples of organic light-emitting materials other than compounds represented by general formula (1) are shown below, but the material is not limited to these.

[0109]

[0110] <Binder Resin> The color conversion composition according to the embodiment of the present invention includes a binder resin in addition to at least one light-emitting material as described above. Preferably, the binder resin is a material with excellent moldability, transparency, heat resistance, etc. Examples of binder resins include, for example, photocurable resist materials having reactive vinyl groups such as acrylic acid-based, methacrylic acid-based, polyvinyl cinnamate-based, and ring rubber-based materials; epoxy resins; silicone resins (including organopolysiloxane cured products (crosslinked products) such as silicone rubber and silicone gel); urea resins; fluororesins; polycarbonate resins; acrylic resins; urethane resins; melamine resins; polyvinyl resins; polyamide resins; phenolic resins; polyvinyl alcohol resins; cellulose resins; aliphatic ester resins; aromatic ester resins; aliphatic polyolefin resins; and aromatic polyolefin resins. Furthermore, mixtures or copolymers of these resins may be used as the binder resin. By appropriately designing these resins, a binder resin useful for the color conversion material according to the embodiment of the present invention can be obtained.

[0111] Among these resins, from the viewpoint of transparency and dispersibility of luminescent materials, it is preferable to use acrylic resin, copolymer resins containing acrylic acid ester or methacrylic acid ester moieties, polyester resins, cycloolefin resins, epoxy resins, or silicone resins. Furthermore, from the viewpoint of heat resistance, hydrogenated styrene resins, resins having a fluorene skeleton, and copolymer resins containing these resins can also be suitably used.

[0112] Examples of binder resins include thermosetting resins, photocurable resins, and thermoplastic resins. Thermoplastic resins are suitable because they have few reactive functional groups and few reactive impurities such as polymerization initiators and crosslinking agents, and therefore do not easily inhibit the luminescence of the light-emitting material. Furthermore, from the viewpoint of heat resistance, thermosetting resins and photocurable resins can be suitably used.

[0113] When the binder resin is a thermoplastic resin, the glass transition temperature (Tg) of the resin is not particularly limited, but is preferably 30°C to 180°C. When Tg is 30°C or higher, the molecular motion of the binder resin due to heat from incident light from a light source and the operating heat of the equipment is suppressed, and the deterioration of durability can be prevented by suppressing changes in the dispersion state of the light-emitting material. When Tg is 180°C or lower, flexibility can be ensured when molded into a sheet or the like. The Tg of the binder resin is more preferably 50°C to 170°C, even more preferably 70°C to 160°C, and particularly preferably 90°C to 150°C. Here, the glass transition temperature of the thermoplastic resin can be measured using a commercially available measuring instrument (for example, a differential scanning calorimeter manufactured by Seiko Electronics Industries Ltd. (product name DSC6220, heating rate 0.5°C / min)).

[0114] The binder resin is a polymer or hydrogenated product of at least one monomer selected from the group consisting of acrylic acid esters, methacrylic acid esters, and styrene, and preferably has a Tg of 100°C or higher. In this case, a Tg of 110°C or higher is more preferable, and 120°C or higher is particularly preferable. These resins can be obtained by known methods, such as copolymerizing each raw material monomer in the presence of a polymerization initiator, or by performing structural transformation after polymerization through chemical reactions such as addition reactions, substitution reactions, or oxidation-reduction reactions. Commercially available products can also be used.

[0115] <Additives> In addition to the light-emitting material and binder resin, the color conversion composition according to the embodiment of the present invention may optionally contain other components (additives), such as fillers, light stabilizers, antioxidants, processing and heat stabilizers, light-resistant stabilizers such as ultraviolet absorbers, dispersants and leveling agents for stabilizing the coating film, scattering agents, plasticizers, crosslinking agents such as epoxy compounds, curing agents such as amines, acid anhydrides, and imidazoles, pigments, and adhesion aids such as silane coupling agents as modifiers for the film surface.

[0116] Examples of fillers include fumed silica, glass powder, quartz powder, and other fine particles, as well as titanium dioxide, zirconia oxide, barium titanate, zinc oxide, and silicone fine particles. Two or more of these may be included.

[0117] Examples of light stabilizers include, but are not limited to, complexes or salts with organic acids containing tertiary amines, catechol derivatives, and at least one transition metal selected from the group consisting of nickel (Ni), scandium (Sc), vanadium (V), manganese (Mn), iron (Fe), cobalt (Co), copper (Cu), yttrium (Y), zirconium (Zr), molybdenum (Mo), silver (Ag), and lanthanides. Furthermore, these light stabilizers may be used individually or in combination.

[0118] Examples of antioxidants include phenolic antioxidants such as 2,6-di-tert-butyl-p-cresol and 2,6-di-tert-butyl-4-ethylphenol, but the product is not limited to these. These antioxidants may be used individually or in combination.

[0119] Examples of processing and heat stabilizing agents include phosphorus-based stabilizers such as tributyl phosphite, tricyclohexyl phosphite, triethylphosphine, and diphenylbutylphosphine, but are not limited to these. These stabilizers may be used individually or in combination.

[0120] Examples of light-resistant stabilizers include benzotriazoles such as 2-(5-methyl-2-hydroxyphenyl)benzotriazole and 2-[2-hydroxy-3,5-bis(α,α-dimethylbenzyl)phenyl]-2H-benzotriazole, but are not limited to these. These light-resistant stabilizers may be used alone or in combination.

[0121] Preferably, the scattering particles are inorganic particles with a refractive index of 1.7 to 2.8, such as titania, zirconia, alumina, ceria, tin oxide, indium oxide, iron oxide, zinc oxide, aluminum nitride, aluminum, tin, titanium or zirconium sulfides, titanium or zirconium hydroxides, etc.

[0122] In the color conversion composition according to the embodiment of the present invention, the content of these additives can be set according to the molar extinction coefficient, fluorescence quantum yield, and absorption intensity at the excitation wavelength of the compound, as well as the size, thickness, and transmittance of the color conversion member to be produced. The content of the additive is 1.0 × 10 per 100 parts by weight of the binder resin. －３ Preferably, it is 1.0 × 10 parts by weight or more. －２ It is more preferably 1.0 × 10 parts by weight or more. －１It is even more preferable that the amount be parts by weight or more. Furthermore, the content of these additives is preferably 30 parts by weight or less, more preferably 15 parts by weight or less, and even more preferably 10 parts by weight or less, per 100 parts by weight of the binder resin.

[0123] <Solvent> The color conversion composition according to the embodiment of the present invention may further contain a solvent. Preferably, the solvent can adjust the viscosity of the resin in a fluid state and does not excessively affect the luminescence and durability of the luminescent material. Examples include water, 2-propanol, ethanol, toluene, methyl acetate, ethyl acetate, propyl acetate, butyl acetate, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, hexane, cyclohexane, tetrahydrofuran, acetone, terpineol, texanol, 1,2-dimethoxyethane, methyl cellsolve, ethyl cellsolve, butyl carbitol, butyl carbitol acetate, 1-methoxy-2-propanol, propylene glycol monomethyl ether acetate, etc. It is also possible to use a mixture of two or more of these solvents. Among these solvents, toluene, methyl ethyl ketone, methyl acetate, ethyl acetate, and tetrahydrofuran are preferably used because they leave little residual solvent after drying.

[0124] The amount of residual solvent in the color conversion layer after drying is preferably 3.0% by mass or less, more preferably 1.0% by mass or less, and even more preferably 0.5% by mass or less, from the viewpoint of further improving the durability of the color conversion member. The amount of residual solvent in the color conversion layer can be measured by gas chromatography.

[0125] <Method for Manufacturing a Color-Changing Composition> An example of a method for manufacturing a color-changing composition according to an embodiment of the present invention is described below. After mixing the aforementioned light-emitting material, binder resin, and other additives and solvents as needed to a predetermined composition, the color-changing composition can be obtained by homogeneously mixing or kneading using a stirrer / kneader. Examples of stirrers / kneaders include homogenizers, orbital stirrers, three-roller stirrers, ball mills, planetary ball mills, bead mills, etc. Degassing under vacuum or reduced pressure conditions is also preferably performed after mixing or dispersion, or during the mixing or dispersion process. In addition, certain components may be mixed in advance, or treatments such as aging may be performed. It is also possible to remove the solvent using an evaporator to obtain the desired solid content concentration.

[0126] <Color Conversion Member> The color conversion member according to the embodiment of the present invention includes the color conversion composition or a cured product thereof. The shape of the color conversion member is not particularly limited and can be, for example, layered, granular, or fibrous. One embodiment of the color conversion member according to the embodiment of the present invention is a color conversion sheet that includes a color conversion composition or a color conversion layer formed by curing the same.

[0127] When the color conversion member according to an embodiment of the present invention has a plurality of color conversion layers, each color conversion layer may be directly laminated, or it may be laminated via an intermediate layer such as an adhesive layer.

[0128] The color conversion member according to the embodiment of the present invention may have a base material and a barrier layer as needed, and may have two or more of these layers.

[0129] There are no particular restrictions on the substrate material; known metals, films, glass, ceramics, paper, etc., can be used. Among these, glass and resin films are preferred. As for the resin film, films made of resins such as polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polyphenylene sulfide, polycarbonate, polypropylene, polyimide, aramid, and silicone are preferred. For ease of peeling the sheet, the surface of the substrate layer may be pre-treated for release. Similarly, to improve interlayer adhesion, the surface of the substrate layer may be pre-treated for easy adhesion.

[0130] When the substrate is in film form, there are no particular restrictions on its thickness, but a lower limit of 12 μm or more is preferred, and 38 μm or more is more preferred. Furthermore, an upper limit of 5000 μm or less is preferred, and 3000 μm or less is more preferred.

[0131] Furthermore, materials such as barrier films, light guide plates, diffusers, diffusion films, prism sheets, reflective polarizing films, wavelength-selective reflective films, wavelength-selective transmitting films, and wavelength-selective absorbing films can also be used as substrates.

[0132] The barrier layer is preferably one that suppresses the penetration of oxygen, moisture, heat, etc., into the color conversion layer, and may have two or more barrier layers. The barrier layer may be on both sides of the light conversion layer, or on one side.

[0133] In one embodiment of the color conversion member according to the present invention, it is preferable that the color conversion member has an oxygen barrier layer. This is preferable because it can suppress oxidative degradation of the light-emitting material by singlet oxygen generated by a dye sensitization mechanism or the like.

[0134] Examples of oxygen barrier layers include inorganic oxides such as silicon oxide, aluminum oxide, titanium oxide, tantalum oxide, zinc oxide, tin oxide, indium oxide, yttrium oxide, and magnesium oxide; inorganic nitrides such as silicon nitride, aluminum nitride, titanium nitride, and silicon carbide nitride; metal oxide thin films or metal nitride thin films with other elements added to these; or films containing various resins such as polyvinylidene chloride, acrylic resins, silicone resins, melamine resins, urethane resins, fluororesins, and polyvinyl alcohol resins such as saponified vinyl acetate. Two or more of these may be included.

[0135] As typical structural examples of color conversion members, Figures 1 to 6 show schematic cross-sectional views of an example of a color conversion sheet, which is a color conversion member according to an embodiment of the present invention. The color conversion sheet shown in Figure 1 has a laminated structure of a base layer 10 and a color conversion layer 11. The color conversion sheet shown in Figure 2 has a laminated structure in which the color conversion layer 11 is sandwiched between a plurality of base layers 10A and 10B. The color conversion sheet shown in Figure 3 has a laminated structure in which the color conversion layer 11 is sandwiched between a plurality of barrier films 12A and 12B and base layers 10A and 10B. The color conversion sheet shown in Figure 4 has a laminated structure in which a plurality of color conversion layers 11A and 11B are sandwiched between a plurality of base layers 10A and 10B. The color conversion sheet shown in Figure 5 has a laminated structure in which an intermediate layer 13 is included between a plurality of color conversion layers 11A and 11B and is sandwiched between a plurality of base layers 10A and 10B. The color conversion sheet shown in Figure 6 has a laminated structure in which an intermediate layer 13 is included between multiple color conversion layers 11A, 11B, and is sandwiched between multiple barrier films 12A, 12B and multiple substrate layers 10A, 10B. However, each layer of the laminated structure shown in Figures 1 to 6 may be in direct contact with the others, or they may be laminated with an adhesive layer in between.

[0136] Furthermore, another embodiment of the color conversion member according to the embodiment of the present invention is a color conversion substrate comprising a plurality of color conversion layers on a substrate. The color conversion layers on the color conversion substrate can also be arranged between partitions (recesses).

[0137] The color conversion member according to the embodiment of the present invention may further have an auxiliary layer having a light diffusion layer, an adhesive layer, an anti-reflective function, an anti-glare function, an anti-reflective anti-glare function, a hard coat function (abrasion resistance function), an anti-static function, an anti-fouling function, an electromagnetic wave shielding function, an infrared cut function, an ultraviolet cut function, a polarization function, a color tuning function, etc., depending on the required function.

[0138] <Method for Manufacturing Color-Changing Members> The method for manufacturing color-changing members according to embodiments of the present invention is not particularly limited as long as it is a method that can mold the color-changing composition according to embodiments of the present invention into a desired shape. For example, one method is to apply the color-changing composition onto a substrate and dry it to form a color-changing layer. If the binder resin is a thermosetting resin, the color-changing composition may be applied to a substrate or the like and then heated and cured to form a color-changing layer. If the binder resin is a photocurable resin, the color-changing composition may be applied to a substrate and then photocured to form a color-changing layer. Other methods include kneading the color-changing composition while heating it and molding it using an extruder, or placing the color-changing composition in a mold and molding it by heating, cooling, drying, etc.

[0139] Coating can be performed using, but is not limited to, reverse roll coaters, blade coaters, comma coaters, slit die coaters, direct gravure coaters, offset gravure coaters, kiss coaters, natural roll coaters, air knife coaters, roll blade coaters, two-stream coaters, rod coaters, wire bar coaters, applicators, dip coaters, curtain coaters, spin coaters, knife coaters, etc.

[0140] The color-changing material can be dried using a general heating device such as a hot air dryer or an infrared dryer. In this case, the heating temperature is preferably 60 to 200°C, and the heating time is preferably 2 minutes to 4 hours. It is also possible to heat-cur the material in stages using methods such as step curing.

[0141] When forming a color conversion layer by heat curing, a hot air oven or the like is used as the heating device. The heating conditions can be selected according to the binder resin. For example, the heating temperature is preferably 100°C to 300°C, and the heating time is preferably 1 minute to 2 hours.

[0142] When forming a color conversion layer by photocuring, it is preferable to irradiate with high-energy light such as ultraviolet light. The light irradiation conditions can be selected according to the binder resin. For example, the wavelength of the irradiated light is preferably 200 nm to 500 nm, and the irradiation dose is 10 mJ / cm². ２ ~10 J / cm ２ It is preferable.

[0143] After creating the color conversion layer, it is possible to change the substrate as needed. In this case, simple methods include replacing the substrate using a hot plate, or using a vacuum laminator or dry film laminator.

[0144] <Light Source Unit> The light source unit according to an embodiment of the present invention comprises at least a light source and the above-mentioned color conversion composition or color conversion member. When the light source unit of the present invention includes a color conversion composition, the arrangement of the light source and the color conversion composition is not particularly limited, and the color conversion composition may be applied directly to the light source, or the color conversion composition may be applied to a film or glass separated from the light source. Furthermore, when the light source unit of the present invention includes a color conversion member, the arrangement of the light source and the color conversion member is not particularly limited, and the light source and the color conversion member may be in close contact, or a remote phosphor configuration may be used with the light source and color conversion member separated. In addition, a color filter may be included for the purpose of increasing color purity, and optical members such as a prism sheet, a reflective polarizing film, or a diffusion film may be included for the purpose of improving brightness or homogenizing the emitted light.

[0145] One embodiment of the light source unit according to the present invention is a configuration that includes a color conversion sheet as shown in Figure 5, with the light source located below Figure 5 and a prism sheet and a reflective polarizing film laminated above Figure 5. A diffuser plate may be provided between the light source and Figure 5, and a reflector plate may be provided below the light source.

[0146] Another embodiment of the light source unit according to the present invention includes a light source and a light guide plate, and a color conversion layer formed by directly applying a color conversion composition to the light-emitting side of the light guide plate is laminated. A light diffusion layer or a wavelength-selective transmission layer may be further formed on the color conversion layer.

[0147] The light source unit of the present invention is useful for various light sources such as spatial illumination and backlighting, and can be used specifically in applications such as displays, lighting, interiors, signs, and billboards, but is particularly suitable for use in displays and lighting applications.

[0148] <Light Source> Any light source that emits light in a wavelength range absorbable by the light-emitting material used in this invention can be used. For example, any light source such as a hot cathode tube, cold cathode tube, fluorescent light source such as an inorganic EL, an organic electroluminescent element light source, an LED light source, an incandescent light source, or sunlight can be used in principle. Among these, LEDs or organic electroluminescent elements are preferred in terms of color purity, and LEDs are more preferred.

[0149] For display and lighting applications, light sources having maximum emission in the 400-500 nm range are preferred because they can enhance the color purity of blue light. Furthermore, blue LEDs having maximum emission in the wavelength range of 430 nm to 480 nm are more preferred, and blue LEDs having maximum emission in the wavelength range of 445 nm to 470 nm are even more preferred.

[0150] The light source may have one type of emission peak or two or more types of emission peaks, but to improve color purity, a light source with one type of emission peak is preferable. It is also possible to use multiple light sources with different types of emission peaks in any combination.

[0151] <Display, Lighting Device> The display according to the embodiment of the present invention comprises at least a light source unit including a light source and a color conversion material composition or color conversion member, as described above. For example, the above-described light source unit is used as a backlight unit in a display such as a liquid crystal display.

[0152] Furthermore, the lighting device according to the embodiment of the present invention comprises at least a light source unit including a light source and a color conversion material composition or color conversion member, as described above. For example, this lighting device is configured to emit white light by combining a blue LED light source as a light source unit with a color conversion material composition or color conversion member that converts the blue light from the blue LED light source into light with a longer wavelength.

[0153] <Compounds> Compounds having the structure represented by general formula (3) will be described in detail.

[0154]

[0155] In general formula (3), X is C-R ７ Or it is N. １ ~R ７ These may be the same or different, and are selected from the group consisting of hydrogen atom, alkyl group, cycloalkyl group, heterocyclic group, alkenyl group, cycloalkenyl group, alkynyl group, hydroxyl group, thiol group, alkoxy group, alkylthio group, aryl ether group, arylthioether group, aryl group, heteroaryl group, halogen, cyano group, aldehyde group, carboxyl group, ester group, amide group, acyl group, sulfonyl group, sulfonic acid ester group, sulfonamide group, nitro group, silyl group, siloxanyl group, boryl group, and phosphine oxide group. １ and R ２ and R ２ and R ３ One of the two sets is a ring structure represented by the following general formula (4). ４ ~R ７ At least one of them is a group represented by the following general formula (5): R ８ and R ９ These groups may be the same or different, and are selected from the group consisting of alkyl groups, cycloalkyl groups, heterocyclic groups, alkenyl groups, cycloalkenyl groups, alkynyl groups, hydroxyl groups, thiol groups, alkoxy groups, alkylthio groups, aryl ether groups, arylthioether groups, aryl groups, heteroaryl groups, halogens, and cyano groups.

[0156]

[0157] In general formula (4), R ２０１ and R ２０２ These may be the same or different, and are selected from the group consisting of hydrogen atoms, alkyl groups, cycloalkyl groups, heterocyclic groups, alkenyl groups, cycloalkenyl groups, alkynyl groups, hydroxyl groups, thiol groups, alkoxy groups, alkylthio groups, aryl ether groups, arylthioether groups, aryl groups, heteroaryl groups, halogens, cyano groups, aldehyde groups, carboxyl groups, ester groups, amide groups, acyl groups, sulfonyl groups, sulfonic acid ester groups, sulfonamide groups, nitro groups, silyl groups, siloxanyl groups, boryl groups, and phosphine oxide groups. Ar is a substituted or unsubstituted aromatic hydrocarbon ring, or a substituted or unsubstituted aromatic heterocycle. Also, R ２０１ and R ２０２ This may form a ring. * indicates the connection to the pyromethene skeleton.

[0158]

[0159] In general formula (5), X １０１ ~X １０４ These may be the same or different, C-R １０１ Or it is N. １０１ is a hydrogen atom or substituent. Adjacent substituents may have a ring structure. * indicates a linkage with the pyromethene skeleton.

[0160] The pyrometenboron complex of the present invention is a compound represented by general formula (3), and has a ring structure represented by general formula (4) on its pyrometenboron complex skeleton. The ring structure of general formula (4) all has a double bond, and this double bond is always chemically bonded to the pyrometenboron complex skeleton by a carbon atom. This suppresses excessive structural relaxation in the excited state, resulting in a sharper emission spectrum for the compound represented by general formula (3). When this compound is used as an luminescent material, emission with good color purity can be obtained. That is, when the compound represented by general formula (3) is used in a color conversion composition, it becomes possible to efficiently create a wider color gamut, improving color reproducibility.

[0161] Furthermore, in the pyrometenboron complex of the present invention, R in general formula (3) ４ ~R ７ At least one of these groups has a group represented by the general formula (5) described above. The group represented by general formula (5) has an N-containing five-membered ring structure and is fixed to the pyrometenboron complex skeleton by hydrogen bonding. This suppresses excessive structural relaxation in the excited state, resulting in a sharper emission spectrum for the compound represented by general formula (3). When this compound is used as an luminescent material, emission with good color purity can be obtained. In other words, when the compound represented by general formula (3) is used in a color conversion composition, it becomes possible to efficiently create a larger color gamut and improve color reproducibility.

[0162] Furthermore, unlike the base ring structure represented by general formula (4), the group represented by general formula (5) does not have a fused ring structure with the pyrometenboron complex skeleton, thus extending conjugation and preventing a significant shift to longer wavelengths in emission. In addition, because the pyrometenboron complex has the group represented by general formula (5), intramolecular motion is suppressed, improving rigidity and thus increasing luminescence efficiency (brightness).

[0163] In compounds represented by general formula (3), R １ and R ２ The combination and R ２ and R ３ One of the two pairs, R, is a ring structure represented by general formula (4), ４ ~R ６ Because at least one of these is a base structure represented by general formula (5), the pyrometenboron complex of the present invention controls the emission wavelength and has high color reproducibility, high brightness, and high durability.

[0164] X in general formula (5) １０１ ~X １０４ These may be the same or different, C-R １０１ Or it is N. １０１ is a hydrogen atom or a substituent.

[0165] From the standpoint of color reproducibility and ease of synthesis, R ６It is preferable that the group is represented by general formula (5). This allows the group structure represented by general formula (5) and the pyrometenboration complex skeleton to interact efficiently.

[0166] From the standpoint of skeletal stability and color reproduction, X in general formula (5) １０１ ~X １０４ It is preferable that at least one of them is N. Among them, X １０１ and X １０４ It is particularly preferable that one of the two atoms is N. N, which can form an intramolecular hydrogen bond with the hydrogen atoms of the pyrometenboron complex skeleton, can interact more efficiently when it is located closer to the pyrometenboron complex skeleton. Also, from a similar viewpoint, R in general formula (3) ５ It is particularly preferable that R is a hydrogen atom. From the viewpoint of photostability, １０１ It is preferable that it is an electron-withdrawing group.

[0167] In general formula (4), Ar is preferably a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted phenanthrene ring, a substituted or unsubstituted pyridine ring, a substituted or unsubstituted pyrimidine ring, or a substituted or unsubstituted pyrazine ring. Furthermore, if Ar is a substituted or unsubstituted benzene ring, it is particularly preferred because it improves thermal and electrical stability. In other words, it is preferable that Ar in general formula (4) is a substituted or unsubstituted benzene ring.

[0168] R in general formula (3) ４ However, R is a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, and ６ It is preferable that the group is represented by the general formula (5) above.

[0169] In general formula (3), R ８ and R ９Preferably, one of the atoms is a fluorine atom. This lowers the electron density of the pyrometenboron complex skeleton, further improving the oxygen stability of the compound represented by general formula (3), and as a result, significantly improving the durability of the compound. Furthermore, when the compound represented by general formula (3) is used in a color conversion composition, the color reproducibility is further improved.

[0170] Also, R ８ and R ９ When any one of them is a fluorine atom, X in general formula (5) １０１ and X １０４ When the bond is C-H, an intramolecular hydrogen bond between H and F is formed, which is preferable because it can suppress excessive structural relaxation in the excited state.

[0171] Based on the above, the compound represented by general formula (3) has a pyrometenboron complex skeleton with a ring structure represented by general formula (4) and a group represented by general formula (5), making it possible to achieve high color purity, high brightness, and high durability simultaneously. Furthermore, the compound represented by general formula (3) exhibits a high emission quantum yield and has a small peak half-width of the emission spectrum, thus enabling efficient color conversion and high color purity.

[0172] Furthermore, compounds having the structure represented by general formula (3) can have various properties and physical characteristics such as luminescence efficiency, color purity, thermal stability, photostability, and dispersibility adjusted by introducing appropriate substituents at appropriate positions.

[0173] Examples of compounds represented by general formula (3) are shown below, but are not limited to these.

[0174]

[0175] The present invention will be described below with reference to examples, but the present invention is not limited to these examples. First, the evaluation method in the examples will be explained.

[0176] <Measurement of Emission Spectra> For the measurement of emission spectra, the color conversion sheets prepared in each example and comparative example were measured using a fluorescence spectrophotometer (Fluoromax 4, manufactured by Horiba, Ltd.). The peak wavelength and full width at half maximum were determined from the obtained emission spectra. The results are shown in Table 1.

[0177] <Measurement of Fluorescence Quantum Yield> In measuring the fluorescence quantum yield, a color conversion sheet prepared using the color conversion composition was cut into an 8 mm square in each example and comparative example to prepare a sample of the color conversion sheet. This prepared sample was excited with excitation light at a wavelength of 540 nm using the Quantaurus-QY absolute fluorescence quantum yield analyzer manufactured by Hamamatsu Photonics, and the fluorescence quantum yield at that time was measured. The results are shown in Table 1.

[0178] <Evaluation of Light Durability> In the evaluation of light durability, for each example and comparative example, a light-emitting device equipped with the fabricated color conversion material and a blue LED (USHIO EPITEX; model number SMBB450H-1100, emission peak wavelength: 450 nm) was subjected to a current of 500 mA to light up the blue LED, and the initial emission peak intensity was measured using a spectroradiometer (CS-1000, Konica Minolta). The distance between the color conversion material and the blue LED element was set to 3 cm. Subsequently, the light from the blue LED element was continuously irradiated in a 70°C environment, and the time until the emission peak intensity decreased by 5% was observed to evaluate the light durability of the color conversion material.

[0179] (Synthesis Example 1) Synthesis Method of Compound R-1 A mixed solution of pyrrole (10.06 g), 3,5-dichlorobenzoyl chloride (47.12 g), and toluene (75 mL) was heated and stirred under a nitrogen stream for 6 hours. Then, after the mixed solution was cooled to room temperature, methanol (75 mL) was added, and the precipitated solid was filtered and vacuum dried. This yielded (3,5-dichlorophenyl)(pyrrole-2-yl)methanone (14.40 g).

[0180] A mixed solution of (3,5-dichlorophenyl)(pyrrole-2-yl)methanone (12.00 g), spirofluoreneindenopyrrole (16.80 g), methanesulfonic anhydride (17.42 g), and degassed toluene (250 mL) was heated under a nitrogen stream at 50°C for 20 hours. Next, diisopropylethylamine (26.13 mL) and boron trifluoride diethyl ether complex (37.68 mL) were added, and the mixture was stirred at 50°C for 1 hour. Subsequently, water (250 mL) was added to the stirred mixed solution, and the organic layer was extracted. The obtained organic layer was washed twice with water (100 mL), dried over magnesium sulfate, and the solvent was removed from the organic layer using an evaporator. The residue was purified by silica gel column chromatography and vacuum dried to obtain dichloropyrmethene (7.19 g).

[0181] Dichloropyrrometene (6.90 g), 4-(methoxycarbonyl)phenylboronic acid (6.48 g), 1 MNa ２ CO ３ Aq. (36 mL) was placed in a flask, THF (120 mL) and PdXPhosG3 (0.30 g) were added, and the mixture was stirred at 60°C for 4 hours under a nitrogen atmosphere. After the reaction was complete, water (40 mL) was added and the mixture was stirred, and the organic layer was separated. This organic layer was dried over magnesium sulfate, filtered, and the solvent was removed by distillation. The resulting reaction product was purified by silica gel chromatography and vacuum-dried to obtain bis(methoxycarbonyl)phenylpyrometene (8.32 g).

[0182] 3.87 g of bis(methoxycarbonyl)phenylpyrometene, 4.24 g of 4-(4-trifluoromethylphenyl)pyrazole, and 3.34 g of silver oxide were placed in a flask, 100 mL of DMSO was added, and the mixture was stirred at 80°C for 4 hours under a nitrogen atmosphere. After the reaction was complete, 20 mL of water was added and the mixture was stirred, and the organic layer was separated. The organic layer was dried over magnesium sulfate, filtered, and the solvent was removed by distillation. The resulting reaction product was purified by silica gel chromatography and vacuum-dried to obtain 0.49 g of compound R-1. １H-NMR (CDCl3, ppm): δ3.98 (s, 6H), 6.29 (s, 1H), 6.65 (d, 1H), 6.80-7.05 (m, 9H), 7 .08-7.51 (m, 5H), 7.54-7.91 (m, 8H), 7.99-8.21 (m, 6H), 8.36 (s, 1H), 9.31 (s, 1H).

[0183] Compounds other than those mentioned above can also be easily synthesized by changing various starting materials such as pyrrole and benzoyl chloride.

[0184] <Luminescent Material> In the following examples and comparative examples, compounds R-1 to R-8 and R-101 are the compounds shown below.

[0185]

[0186] <Scattering material> Titanium dioxide particles JR-301 (manufactured by Teika Co., Ltd.) were used as the scattering material.

[0187] Example 1 PMMA resin BR-85 (manufactured by Mitsubishi Chemical Corporation) was used as the binder resin. 100 parts by weight of the binder resin was mixed with 0.03 parts by weight of compound R-1 as a light-emitting material, 1 part by weight of JR-301 as a scattering material, and 300 parts by weight of ethyl acetate as a solvent. The mixture was then stirred and defoamed at 1000 rpm for 20 minutes using a planetary stirring and defoaming device "Mazelstar" (registered trademark) KK-400 (manufactured by Kurabo Corporation) to obtain a resin composition for producing a color conversion layer.

[0188] Next, a resin solution for creating a color conversion layer was applied to "Therapiel" BLK (manufactured by Toray Film Processing Co., Ltd.) using a film applicator, and heated and dried at 120°C for 20 minutes to form a color conversion layer with an average film thickness of 16 μm. When the light durability of this sheet-like color conversion member was evaluated using the method described above, the time required for the emission peak intensity to decrease by 5% was 2654 hours, which is approximately 3.8 times more durable than Comparative Example 1 described later.

[0189] Examples 2-8: Sheet-like color-converting members were manufactured in the same manner as in Example 1, except that the luminescent material was changed to one of those listed in Table 1, and the amount of luminescent material mixed was adjusted to be the same as the amount of substance in R-1 of Example 1. The results are shown in Table 1.

[0190] Comparative Example 1: A sheet-like color-converting member was prepared in the same manner as in Example 1, except that the light-emitting material was changed to one of those listed in Table 1, and the amount of light-emitting material mixed was adjusted to be the same as the amount of substance in R-1 of Example 1. The results are shown in Table 1.

[0191] In Examples 1 to 8, a narrow full width at half maximum (FMAX) was obtained in the wavelength range of 600 to 635 nm, providing a color conversion member that achieved both high color purity and high fluorescence quantum yield. In particular, Example 1 achieved both high color purity emission with a FMAX of 35 nm or less and high fluorescence quantum yield, while also exhibiting high photodurability. On the other hand, Comparative Example 1 had a broad emission wavelength with a FMAX of 40 nm or more, and was inferior in terms of color purity, fluorescence quantum yield, and photodurability.

[0192]

[0193] 1. Color conversion sheet 10, 10A, 10B; Substrate layer 11, 11A, 11B; Color conversion layer 12, 12A, 12B; Barrier film 13. Intermediate layer

Claims

1. A color conversion composition comprising at least one light-emitting material and a binder resin, wherein said at least one light-emitting material contains a compound having a structure represented by general formula (1). (In general formula (1), X is C-R ７ or N. R １ to R ７ may each be the same or different and are selected from the group consisting of a hydrogen atom, 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, an aryl thioether group, an aryl group, a heteroaryl group, halogen, a cyano group, an aldehyde group, a carboxyl group, an ester group, an amide group, an acyl group, a sulfonyl group, a sulfonic acid ester group, a sulfonamide group, a nitro group, a silyl group, a siloxanyl group, a boryl group, and a phosphine oxide group. R １ and R ２ and R ２ and R ３ one of the two pairs may be a ring structure represented by the following general formula (4). At least one of R １ to R ７ is a group represented by the following general formula (2). R ８ and R ９ may each be the same or different and are selected from the group consisting of 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, an aryl thioether group, an aryl group, a heteroaryl group, halogen, and a cyano group.) (In general formula (2), X １０１ to X １０４ may each be the same or different, and are C-R １０１ or N. R １０１ is a hydrogen atom or a substituent. Adjacent substituents may have a ring structure. * indicates a bonding site to the pyrromethene skeleton.) (In general formula (4), R ２０１ and R ２０２ These may be the same or different, and are selected from the group consisting of hydrogen atoms, alkyl groups, cycloalkyl groups, heterocyclic groups, alkenyl groups, cycloalkenyl groups, alkynyl groups, hydroxyl groups, thiol groups, alkoxy groups, alkylthio groups, aryl ether groups, arylthioether groups, aryl groups, heteroaryl groups, halogens, cyano groups, aldehyde groups, carboxyl groups, ester groups, amide groups, acyl groups, sulfonyl groups, sulfonic acid ester groups, sulfonamide groups, nitro groups, silyl groups, siloxanyl groups, boryl groups, and phosphine oxide groups. Ar is a substituted or unsubstituted aromatic hydrocarbon ring, or a substituted or unsubstituted aromatic heterocycle. Also, R ２０１ and R ２０２ This may form a ring. (* indicates the connection point with the pyromethene skeleton.) 2. X in the general formula (2) １０１ ~X １０４ At least one of them is CR １０１ And R １０１ The color conversion composition according to claim 1, wherein is an electron-withdrawing group.

3. R ​​in the general formula (2) １０１ The color conversion composition according to claim 2, wherein the member is a fluorine atom, a fluorine-containing aryl group, a fluorine-containing heteroaryl group, a fluorine-containing alkyl group, a substituted or unsubstituted acyl group, a substituted or unsubstituted ester group, a substituted or unsubstituted amide group, a substituted or unsubstituted sulfonyl group, or a cyano group.

4. In the general formula (2) above, X １０１ ~X １０４ The color conversion composition according to claim 1, wherein one of them is N.

5. In the general formula (2) above, X １０１ If N and X １０３ CR １０１ The color conversion composition according to claim 1.

6. In the general formula (2) above, X １０１ If N and X １０２ and X １０３ CR １０１ The color conversion composition according to claim 1.

7. In the general formula (1) above, R ３ and R ６ The color conversion composition according to claim 1, wherein at least one of the groups is a group represented by the general formula (2).

8. In the general formula (1) above, R ８ and R ９ The color conversion composition according to claim 1, wherein at least one of the atoms is a fluorine atom.

9. The color conversion composition according to claim 1, wherein the light-emitting material exhibits emission observed in the region of 580 nm or more and less than 750 nm when excitation light is used.

10. A cured product of the color conversion composition according to any one of claims 1 to 9.

11. A color-converting member comprising a color-converting composition or a cured product thereof according to any one of claims 1 to 9.

12. A light source unit comprising a light source and a color conversion member as described in claim 11.

13. A display comprising the light source unit described in claim 12.

14. A lighting device comprising the light source unit described in claim 12.

15. A pyrometenboron complex represented by the following general formula (3). (In general formula (3), X is C-R ７ Or it is N. １ ~R ７ These may be the same or different, and are selected from the group consisting of hydrogen atoms, alkyl groups, cycloalkyl groups, heterocyclic groups, alkenyl groups, cycloalkenyl groups, alkynyl groups, hydroxyl groups, thiol groups, alkoxy groups, alkylthio groups, aryl ether groups, arylthioether groups, aryl groups, heteroaryl groups, halogens, cyano groups, aldehyde groups, carboxyl groups, ester groups, amide groups, acyl groups, sulfonyl groups, sulfonic acid ester groups, sulfonamide groups, nitro groups, silyl groups, siloxanyl groups, boryl groups, and phosphine oxide groups. １ and R ２ and R ２ and R ３ One of the two sets is a ring structure represented by the following general formula (4): R ４ ~R ７ At least one of them is a group represented by the following general formula (5): R ８ and R ９ These groups may be the same or different, and are selected from the group consisting of alkyl groups, cycloalkyl groups, heterocyclic groups, alkenyl groups, cycloalkenyl groups, alkynyl groups, hydroxyl groups, thiol groups, alkoxy groups, alkylthio groups, aryl ether groups, arylthioether groups, aryl groups, heteroaryl groups, halogens, and cyano groups. (In general formula (4), R ２０１ and R ２０２ These may be the same or different, and are selected from the group consisting of hydrogen atoms, alkyl groups, cycloalkyl groups, heterocyclic groups, alkenyl groups, cycloalkenyl groups, alkynyl groups, hydroxyl groups, thiol groups, alkoxy groups, alkylthio groups, aryl ether groups, arylthioether groups, aryl groups, heteroaryl groups, halogens, cyano groups, aldehyde groups, carboxyl groups, ester groups, amide groups, acyl groups, sulfonyl groups, sulfonic acid ester groups, sulfonamide groups, nitro groups, silyl groups, siloxanyl groups, boryl groups, and phosphine oxide groups. Ar is a substituted or unsubstituted aromatic hydrocarbon ring, or a substituted or unsubstituted aromatic heterocycle. Also, R ２０１ and R ２０２ This may form a ring. (* indicates the connection point with the pyromethene skeleton.) (In general formula (5), X １０１ ~X １０４ These may be the same or different, C-R １０１ Or it is N. １０１ is a hydrogen atom or substituent. Adjacent substituents may have a ring structure. * indicates a linkage to the pyromethene skeleton.

16. In the above general formula (3), R ６ The pyrometenboron complex according to claim 15, wherein is a group represented by the general formula (5).

17. The pyrometenboron complex according to claim 15, wherein Ar in the general formula (4) is a substituted or unsubstituted benzene ring.

18. In the above general formula (5), X １０１ ~X １０４ The pyrometenboron complex according to claim 15, wherein at least one of the members is N.

19. R in the general formula (3) ４ However, R is a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, and ６ The pyrometenboron complex according to claim 15, wherein is the group represented by the general formula (5).

20. In the above general formula (3), R ８ and R ９ The pyrometenboron complex according to claim 15, wherein at least one of the atoms is a fluorine atom.

21. A pyrometenboron complex according to any one of claims 15 to 20, which exhibits emission observed in the region of peak wavelength between 580 nm and 750 nm when excitation light is used.

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