Color conversion composition, color conversion sheet, light source unit, display device, and illumination device

Abstract

A color conversion composition according to one embodiment of the present invention contains the following component (A), component (B), and component (C). Component (A): a luminescent material. Component (B): a binder resin. Component (C): a compound represented by general formula (1) (In general formula (1), X1 and X2 are each independently O or S. Ra to Rc are each independently selected from the group consisting of a hydrogen atom, an alkyl group, a cycloalkyl group, a heterocyclic group, an alkenyl group, an alkynyl group, a hydroxyl group, an alkoxy group, a thiol group, an alkylthio group, an aryl ether group, an aryl sulfide group, an aryl group, a heteroaryl group, a halogen, a cyano group, an aldehyde group, an oxycarbonyl group, a carbamoyl group, an amino group, a nitro group, a silyl group, a siloxane group, a boryl group, a phosphine oxide group,-C (= O) R101,-S (= O) R102R103,-S (= O) R104, and-S (= O) 2R105; and fused rings or aliphatic rings formed between adjacent substituents. R101 to R105 are substituents, and R102 and R103 may be fused together to form a ring. In this connection, at least one of Ra-Rc represents an electron-withdrawing group. And n represents an integer of 1-4). # imgabs0 #

Description

Technical Field

[0001] The present invention relates to a color conversion composition, a color conversion sheet, a light source unit, a display device, and a lighting device. Background Art

[0002] Active research is underway to apply color conversion technology to liquid crystal displays, organic EL displays, lighting devices, etc. Color conversion refers to converting light from a light emitter into light with a longer wavelength, such as converting blue light into green or red light.

[0003] By forming a composition having the color conversion function (hereinafter referred to as the color conversion composition) into a sheet and combining it with a blue light source, for example, the three primary colors of blue, green, and red can be obtained from the blue light source, that is, white light can be obtained. By using such a white light source composed of a blue light source and a sheet having a color conversion function (hereinafter referred to as a color conversion sheet) as a light source unit such as a backlight unit, and combining the light source unit, a liquid crystal drive unit, and a color filter, a full-color display can be produced. In addition, the white light source combined with the blue light source and the color conversion sheet can also be directly used as a white light source (illumination device) such as LED lighting.

[0004] As a subject of liquid crystal displays using a color conversion method, the improvement of color reproducibility and durability can be cited. For the improvement of color reproducibility, it is effective to narrow the half-value width of each emission spectrum of blue, green, and red of the light source unit and improve the color purity of each color of blue, green, and red. As an example of a means to solve this problem, a color conversion material containing a pyrromethene compound is proposed (for example, see patent documents 1 to 2). In addition, as an example of a technology for improving durability, a technology of adding a light stabilizer is proposed (for example, see patent documents 3 to 4).

[0005] Prior art literature

[0006] Patent Literature

[0007] Patent Document 1: Japanese Patent Application Publication No. 2010-61824

[0008] Patent Document 2: Japanese Patent Application Publication No. 2014-136771

[0009] Patent Document 3: International Publication No. 2017 / 014068

[0010] Patent Document 4: International Publication No. 2021 / 192795 Summary of the invention

[0011] Problems to be solved by the invention

[0012] However, even if the color conversion composition is prepared using the organic light-emitting materials described in Patent Documents 1 to 3, it is still insufficient from the perspective of improving color reproducibility and durability (light durability). In addition, the technology described in Patent Document 4 has problems in terms of moisture resistance, and there is a problem that the fluorescence quantum yield is significantly reduced under high temperature and high humidity.

[0013] Therefore, an object of the present invention is to provide a color conversion composition, a color conversion sheet, a light source unit, a display device, and a lighting device that are excellent in light durability and moisture resistance.

[0014] Means for solving problems

[0015] In order to solve the above problems and achieve the purpose, the present invention has the configuration described in any one of the following [1] to

[15] .

[0016] That is, the color conversion composition according to the present invention is characterized by [1] containing the following components (A), (B), and (C).

[0017] (A) Ingredients: Luminescent material

[0018] (B) Component: Binder resin

[0019] Component (C): a compound represented by the following general formula (1)

[0020] [Chemical formula 1]

[0021]

[0022] (In general formula (1), X 1 and X 2 Each independently is O or S. R a ~R c each independently selected from a hydrogen atom, an alkyl group, a cycloalkyl group, a heterocyclic group, an alkenyl group, an alkynyl group, a hydroxyl group, an alkoxy group, a thiol group, an alkylthio group, an aryl ether group, an aryl thioether group, an aryl group, a heteroaryl group, a halogen group, a cyano group, an aldehyde group, an oxycarbonyl group, a carbamoyl group, an amino group, a nitro group, a silyl group, a siloxane group, a boron group, a phosphine oxide group, -C(=O)R 101 、-S(=O)R 102 R 103 、-S(=O)R 104 、-S(=O)2R 105 and a group consisting of a condensed ring or an aliphatic ring formed with adjacent substituents. 101 ~R 105 is a substituent, R 102 With R 103 can be fused together to form a ring. a ~R cAt least one of them is an electron withdrawing group. n is an integer of 1 to 4.)

[0023] Furthermore, the color conversion composition according to the present invention is characterized in that [2] in the invention described in the above [1], the electron withdrawing group is a group containing a fluorine atom.

[0024] The color conversion composition according to the present invention is characterized in that [3] in the invention described in [1] or [2] above, the electron withdrawing group is a group having 4 or more fluorine atoms.

[0025] In addition, the color conversion composition according to the present invention is characterized in that [4] in the invention described in any one of [1] to [3] above, the electron withdrawing group is a perfluoroalkyl group having 2 or more carbon atoms.

[0026] In addition, the color conversion composition of the present invention is characterized in that [5] in the invention described in any one of [1] to [4] above, R in the general formula (1) b A hydrogen atom.

[0027] In addition, the color conversion composition of the present invention is characterized in that: [6] in the invention described in any one of [1] to [5], X in the general formula (1) 1 and X 2 Both are O.

[0028] The color conversion composition according to the present invention is characterized in that [7] in the invention described in any one of [1] to [6] above, the component (A) contains a compound represented by the following general formula (2).

[0029] [Chemical formula 2]

[0030]

[0031] (In general formula (2), X is CR 7 or N. R 1 ~R 9 They may be the same as or different from each other 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, a halogen group, a cyano group, an aldehyde group, a carbonyl group, a carboxyl group, an oxycarbonyl group, a carbamoyl group, an amino group, a nitro group, a silyl group, a siloxane group, a boron group, a phosphine oxide group, and a condensed ring or an aliphatic ring formed with an adjacent substituent.)

[0032] In addition, the color conversion composition of the present invention is characterized in that [8] in the invention described in [7] above, R in the general formula (2) 1 ~R6 At least one of them is an electron withdrawing group, and X in the general formula (2) is CR 7 , the R 7 It is a group represented by the following general formula (3).

[0033] [Chemical formula 3]

[0034]

[0035] (In the general formula (3), r is 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, a halogen, a cyano group, an aldehyde group, a carbonyl group, a carboxyl group, an oxycarbonyl group, a carbamoyl group, an amino group, a nitro group, a silyl group, a siloxane group, a boron group, and a phosphine oxide group. k is an integer of 1 to 3. When k is 2 or more, r may be the same as or different from each other.)

[0036] In addition, the color conversion composition according to the present invention is characterized in that [9] in the invention described in any one of [1] to [8] above, the component (A) contains at least one of the following luminescent materials (a) and (b).

[0037] Luminescent material (a): A luminescent material that emits light with a peak wavelength observed in a region of 500 nm to less than 580 nm by using excitation light with a wavelength in the range of 400 nm to 500 nm.

[0038] Luminescent material (b): A luminescent material that is excited by at least one of excitation light having a wavelength in the range of 400 nm to 500 nm and luminescence from the luminescent material (a), thereby exhibiting luminescence with a peak wavelength observed in the region of 580 nm to 750 nm.

[0039] The color conversion composition according to the present invention is characterized in that

[10] in the invention described in any one of [1] to [9] above, the component (B) is a thermoplastic resin.

[0040] In addition, the color conversion sheet according to the present invention is characterized by

[11] comprising the color conversion composition or a cured product thereof according to any one of [1] to

[10] .

[0041] Furthermore, the light source unit according to the present invention is characterized in that

[12] it includes a light source and the color conversion composition according to any one of [1] to

[10] .

[0042] In addition, the light source unit according to the present invention is characterized in that

[13] in the invention described in the above

[12] , the light source is a light emitting diode having a maximum light emission within a wavelength range of not less than 400 nm and not more than 500 nm.

[0043] In addition, the display device according to the present invention is characterized in that

[14] it includes the light source unit described in

[12] or

[13] .

[0044] In addition, the lighting device according to the present invention is characterized in that

[15] includes the light source unit described in

[12] or

[13] .

[0045] Effects of the Invention

[0046] The color conversion composition and the color conversion sheet using the same according to the present invention can achieve an effect of improving durability and moisture resistance. BRIEF DESCRIPTION OF THE DRAWINGS

[0047] [ Figure 1 ] Figure 1 This is a schematic cross-sectional view showing a first example of a color conversion sheet according to an embodiment of the present invention.

[0048] [ Figure 2 ] Figure 2 This is a schematic cross-sectional view showing a second example of the color conversion sheet according to the embodiment of the present invention.

[0049] [ Figure 3 ] Figure 3 This is a schematic cross-sectional view showing a third example of the color conversion sheet according to the embodiment of the present invention.

[0050] [ Figure 4 ] Figure 4 This is a schematic cross-sectional view showing a fourth example of the color conversion sheet according to the embodiment of the present invention. DETAILED DESCRIPTION

[0051] Preferred embodiments of the color conversion composition, color conversion sheet, light source unit, display device, and lighting device according to the present invention are described below in detail. However, the present invention is not limited to the following embodiments and can be implemented with various modifications depending on the purpose and application.

[0052] <Color conversion composition>

[0053] The color conversion composition according to an embodiment of the present invention (hereinafter, sometimes referred to as the color conversion composition of the present invention) contains the components (A), (B) and (C) described below. In the present invention, the component (A) is a luminescent material, the component (B) is a binder resin, and the component (C) is a compound represented by the general formula (1) described below.

[0054] <(A) Component: Luminescent Material>

[0055] The color conversion composition according to an embodiment of the present invention contains at least one light emitting material as component (A). Here, the light emitting material in the present invention refers to a material that emits light of a wavelength different from that of a certain light when irradiated with the light.

[0056] As the luminescent material, for example, inorganic phosphors, fluorescent pigments, fluorescent dyes, quantum dots, etc. can be cited. The color conversion composition of the present invention may contain two or more of these luminescent materials as component (A). In order to achieve efficient color conversion, component (A) is preferably a luminescent material that exhibits luminescent properties with high quantum yield. For example, as component (A), quantum dots and organic luminescent materials are preferred, among which organic luminescent materials are more preferred.

[0057] Examples of the organic light-emitting material include the following materials. For example, preferred organic light-emitting materials include naphthalene, anthracene, phenanthrene, pyrene, Compounds having condensed aromatic rings such as naphthacene, triphenylene, perylene, fluoranthene, fluorene, indene, and derivatives thereof. In addition, preferred organic light-emitting materials include compounds having heteroaromatic rings such as furan, pyrrole, thiophene, thiole, 9-silafluorene, 9,9'-spirodisilafluorene, benzothiophene, benzofuran, indole, dibenzothiophene, dibenzofuran, imidazopyridine, phenanthroline, pyridine, pyrazine, naphthyridine, quinoxaline, pyrrolopyridine, and derivatives thereof, and borane derivatives thereof.

[0058] In addition, suitable organic light-emitting materials include stilbene derivatives such as 1,4-distyrylbenzene, 4,4'-bis(2-(4-diphenylaminophenyl)vinyl)biphenyl, 4,4'-bis(N-(stilbene-4-yl)-N-phenylamino)stilbene, aromatic acetylene derivatives, tetraphenylbutadiene derivatives, aldazine derivatives, pyrrole methylene derivatives, diketopyrrolo[3,4-c]pyrrole derivatives, etc. In addition, suitable organic light-emitting materials include coumarin derivatives such as coumarin 6, coumarin 7, and coumarin 153, azole derivatives such as imidazole, thiazole, thiadiazole, carbazole, oxazole, oxadiazole, and triazole, and metal complexes thereof, cyanine compounds such as indocyanine green, xanthene compounds such as fluorescein, eosin, and rhodamine, and thioxanthene compounds.

[0059] In addition, as suitable organic light-emitting materials, polyphenylene compounds, naphthalimide derivatives, phthalocyanine derivatives and metal complexes thereof, porphyrin derivatives and metal complexes thereof, 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, etc. can be cited. In addition, as suitable organic light-emitting materials, organic metal complex compounds such as iridium (Ir), ruthenium (Ru), rhodium (Rh), palladium (Pd), platinum (Pt), osmium (Os), and rhenium (Re) can be cited. However, the organic light-emitting materials in the present invention are not limited to the above materials.

[0060] The organic light-emitting material may be a fluorescent material or a phosphorescent material. In order to achieve high color purity, a fluorescent material is preferred. Among them, from the perspective of imparting a high fluorescence quantum yield and better durability, a pyrromethene derivative may be suitably used as the above-mentioned organic light-emitting material. A more preferred organic light-emitting material is a compound represented by the general formula (2).

[0061] [Chemical formula 4]

[0062]

[0063] When the component (A) contains a compound represented by the general formula (2) as an organic light-emitting material, in the general formula (2), X is CR 7 or N. R 1 ~R 9 The substituents may be the same as or different from each other 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, a halogen, a cyano group, an aldehyde group, a carbonyl group, a carboxyl group, an oxycarbonyl group, a carbamoyl group, an amino group, a nitro group, a silyl group, a siloxane group, a boron group, a phosphine oxide group, and a condensed ring or an aliphatic ring formed with an adjacent substituent.

[0064] In all the above groups, hydrogen may be deuterium. This also applies to the compounds described below or their partial structures. In the following description, for example, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms refers to an aryl group having 6 to 40 carbon atoms, including the number of carbon atoms contained in the substituent substituted on the aryl group. The same applies to other substituents with specified carbon atoms.

[0065] In addition, among all the above groups, as the substituent in the case of being substituted, preferably, 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, a halogen group, a cyano group, an aldehyde group, a carbonyl group, a carboxyl group, an oxycarbonyl group, a carbamoyl group, an amino group, a nitro group, a silyl group, a siloxane group, a boron group, a phosphine oxide group, and further, the preferred specific substituents in the description of each substituent are preferred. In addition, these substituents may be further substituted by the above substituents.

[0066] The term "unsubstituted" in the case of "substituted or unsubstituted" means substitution with a hydrogen atom or a deuterium atom. The same applies to the case of "substituted or unsubstituted" in the compounds or partial structures described below.

[0067] In all the above groups, alkyl represents saturated aliphatic hydrocarbon groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, etc., which may have a substituent or may not have a substituent. There is no particular restriction on the additional substituent in the case of being substituted, for example, alkyl, halogen, aryl, heteroaryl, etc. can be cited, and this aspect is also the same in the following description. In addition, the carbon number of the alkyl is not particularly limited, and from the aspect of the ease of obtaining and the cost, it is preferably in the range of 1 to 20, more preferably in the range of 1 to 8.

[0068] The cycloalkyl group represents a saturated alicyclic hydrocarbon group such as cyclopropyl, cyclohexyl, norbornyl, adamantyl, etc., which may or may not have a substituent. The number of carbon atoms in the alkyl part is not particularly limited, but is preferably in the range of 3 or more and 20 or less.

[0069] The heterocyclic group represents an aliphatic ring having atoms other than carbon in the ring, such as a pyran ring, a piperidine ring, and a cyclic amide, and may or may not have a substituent. The number of carbon atoms in the heterocyclic group is not particularly limited, but is preferably in the range of 2 or more and 20 or less.

[0070] The alkenyl group represents an unsaturated aliphatic hydrocarbon group containing a double bond, such as a vinyl group, an allyl group, and a butadienyl group, and these may or may not have a substituent. The number of carbon atoms in the alkenyl group is not particularly limited, but is preferably in the range of 2 or more and 20 or less.

[0071] The cycloalkenyl group represents an unsaturated alicyclic hydrocarbon group containing a double bond, such as cyclopentenyl, cyclopentadienyl, and cyclohexenyl, and may or may not have a substituent. The number of carbon atoms in the cycloalkenyl group is not particularly limited, but is preferably in the range of 3 or more and 20 or less.

[0072] The alkynyl group represents an unsaturated aliphatic hydrocarbon group containing a triple bond, such as an ethynyl group, and may or may not have a substituent. The number of carbon atoms in the alkynyl group is not particularly limited, but is preferably in the range of 2 or more and 20 or less.

[0073] The alkoxy group represents a functional group such as methoxy, ethoxy, propoxy, etc., to which an aliphatic hydrocarbon group is bonded via an ether bond, and the aliphatic hydrocarbon group may or may not have a substituent. The number of carbon atoms in the alkoxy group is not particularly limited, but is preferably in the range of 1 or more and 20 or less.

[0074] The alkylthio group is a group in which the oxygen atom of the ether bond of the alkoxy group is replaced by a sulfur atom. The hydrocarbon group of the alkylthio group may or may not have a substituent. The number of carbon atoms in the alkylthio group is not particularly limited, but is preferably in the range of 1 to 20.

[0075] The aryl ether group represents a functional group to 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 a substituent. The number of carbon atoms in the aryl ether group is not particularly limited, but is preferably in the range of 6 or more and 40 or less.

[0076] The aryl thioether group is a group in which the oxygen atom of the ether bond of the aryl ether group is substituted with a sulfur atom. The aromatic hydrocarbon group in the aryl thioether group may or may not have a substituent. The number of carbon atoms in the aryl thioether group is not particularly limited, but is preferably in the range of 6 or more and 40 or less.

[0077] The aryl group represents, for example, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, triphenylenyl, benzanthryl, The aromatic hydrocarbon groups include phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, pyrenyl, fluoranthenyl, triphenylene, benzofluoranthenyl, dibenzoanthryl, perylene, spiroenyl, etc. Among them, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, pyrenyl, fluoranthenyl, triphenylene. The aryl group may or may not have a substituent. The number of carbon atoms in the aryl group is not particularly limited, and is preferably in the range of 6 to 40, and more preferably in the range of 6 to 30.

[0078] R 1 ~R 9 In the case of a substituted or unsubstituted aryl group, the aryl group is preferably phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, more preferably phenyl, biphenyl, terphenyl, naphthyl, further preferably phenyl, biphenyl, terphenyl, particularly preferably phenyl.

[0079] When each substituent is further substituted with an aryl group, the aryl group is preferably a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a phenanthryl group, or an anthracenyl group, more preferably a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group, and particularly preferably a phenyl group.

[0080] The heteroaryl group represents a cyclic aromatic group having atoms other than carbon in one or more rings, for example, pyridyl, furyl, thienyl, quinolyl, isoquinolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, naphthyridinyl, cinnolinyl, phthalazinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothienyl, indolyl, dibenzofuranyl, dibenzothienyl, carbazolyl, benzocarbazolyl, carbolyl, indolecarbazolyl, benzofuranocarbazolyl, benzothiophenocarbazolyl, dihydroindenocarbazolyl, benzoquinolyl, acridinyl, dibenzoacridinyl, benzimidazolyl, imidazopyridinyl, benzoxazolyl, benzothiazolyl, phenanthrolinyl, etc. Among them, naphthyridinyl represents any one of 1,5-naphthyridinyl, 1,6-naphthyridinyl, 1,7-naphthyridinyl, 1,8-naphthyridinyl, 2,6-naphthyridinyl, and 2,7-naphthyridinyl. The heteroaryl group may or may not have a substituent. The number of carbon atoms in the heteroaryl group is not particularly limited, but is preferably in the range of 2 to 40, and more preferably in the range of 2 to 30.

[0081] In R 1 ~R 9 In the case of a substituted or unsubstituted heteroaryl group, the heteroaryl group is preferably a pyridyl group, a furyl group, a thienyl group, a quinolyl group, a pyrimidinyl group, a triazine group, a benzofuranyl group, a benzothienyl group, an indolyl group, a dibenzofuranyl group, a dibenzothienyl group, a carbazolyl group, a benzimidazolyl group, an imidazopyridyl group, a benzoxazolyl group, a benzothiazolyl group, a phenanthroline group, more preferably a pyridyl group, a furyl group, a thienyl group, a quinolyl group, and particularly preferably a pyridyl group.

[0082] When each substituent is further substituted by a heteroaryl group, the heteroaryl group is preferably a pyridyl group, a furyl group, a thienyl group, a quinolyl group, a pyrimidinyl group, a triazine group, a benzofuranyl group, a benzothienyl group, an indolyl group, a dibenzofuranyl group, a dibenzothienyl group, a carbazolyl group, a benzimidazolyl group, an imidazopyridyl group, a benzoxazolyl group, a benzothiazolyl group, or a phenanthroline group, more preferably a pyridyl group, a furyl group, a thienyl group, or a quinolyl group. A pyridyl group is particularly preferred.

[0083] Halogen represents an atom selected from fluorine, chlorine, bromine and iodine. In addition, carbonyl, carboxyl, oxycarbonyl and carbamoyl may or may not have a substituent. Here, as a substituent, for example, an alkyl group, a cycloalkyl group, an aryl group, a heteroaryl group and the like can be cited, and these substituents may be further substituted.

[0084] The amino group is a substituted or unsubstituted amino group. The amino group may or may not have a substituent, and as the substituent in the case of substitution, for example, an aryl group, a heteroaryl group, a straight-chain alkyl group, a branched-chain alkyl group, etc. can be cited. As the aryl group and the heteroaryl group, phenyl, naphthyl, pyridyl, and quinolyl are preferred. 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 in the range of 6 to 40, and particularly preferably in the range of 6 to 30.

[0085] The silyl group includes, for example, alkyl silyl groups such as trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, propyldimethylsilyl, and vinyldimethylsilyl; and aryl silyl groups such as phenyldimethylsilyl, tert-butyldiphenylsilyl, triphenylsilyl, and trinaphthylsilyl. The substituent 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.

[0086] The siloxane group represents a silicon compound group formed via an ether bond, such as a trimethylsiloxane group. The substituent on silicon may be further substituted. In addition, the boryl group is a substituted or unsubstituted boryl group. The boryl group may or may not have a substituent, and as the substituent in the case of substitution, for example, an aryl group, a heteroaryl group, a straight-chain alkyl group, a branched-chain alkyl group, an aryl ether group, an alkoxy group, a hydroxyl group, etc. can be cited. Among them, an aryl group and an aryl ether group are preferred. In addition, the phosphine oxide group is -P(=O)R 10 R 11 Represents a group. 10 R 11 Selected from R 1 ~R 9 Same group.

[0087] In addition, the fused ring or aliphatic ring formed between adjacent substituents means that any two adjacent substituents (for example, R 1 and R 2 ) are bonded to each other to form a conjugated or non-conjugated cyclic skeleton. As the constituent elements of such condensed rings or aliphatic rings, in addition to carbon, elements selected from nitrogen, oxygen, sulfur, phosphorus and silicon may also be included. In addition, the above-mentioned condensed rings or aliphatic rings may be further condensed with other rings.

[0088] The compound represented by the general formula (2) exhibits a high fluorescence quantum yield and a small half-peak width of the emission spectrum, and thus can achieve both efficient color conversion and high color purity, and can further improve durability.

[0089] In addition, for the compound represented by general formula (2), various characteristics and properties such as luminous efficiency, color purity, thermal stability, light stability and dispersibility can be adjusted by introducing appropriate substituents into appropriate positions. 1 , R 3 , R 4 and R 6 Compared with the case where all atoms are hydrogen, R 1 , R 3 , R 4 and R 6 When at least one of them is a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, better thermal stability and photostability are exhibited.

[0090] R 1 , R 3 , R 4 and R 6 Preferred examples of are methyl, ethyl, isopropyl, tert-butyl, phenyl, biphenyl, terphenyl, naphthyl, pyridyl, and quinolyl. 1 , R 3 , R 4 and R 6 They can be the same or different from each other.

[0091] R 2 and R 5 Preferred are hydrogen atoms, alkyl groups, carbonyl groups, oxycarbonyl groups, and aryl groups. Among them, alkyl groups and hydrogen atoms are preferred from the viewpoint of thermal stability, and hydrogen atoms are more preferred from the viewpoint of easily obtaining a narrow half-value width in the emission spectrum.

[0092] R 8 and R 9 Preferably, R is an alkyl group, an aryl group, a heteroaryl group, a fluorine group, a fluorine-containing alkyl group, a fluorine-containing heteroaryl group or a fluorine-containing aryl group. 8 and R 9 More preferably, it is fluorine or fluorine-containing aromatic group. 8 and R 9 When the compound is a fluorine or fluorine-containing aromatic group, the electron-donating property of the compound represented by the general formula (2) becomes weak, thereby suppressing the electron interaction with the component (C), and achieving a high fluorescence quantum yield.

[0093] In addition, from the viewpoint of suppressing the decrease in the fluorescence quantum yield of the component (A) caused by the component (C), R 1 ~R 7At least one of them is preferably a substituent with a moderately large volume. The color conversion composition according to an embodiment of the present invention contains component (A) and component (C) in the same layer. Therefore, in the layer of the color conversion composition, the collision between component (A) and component (C) occurs due to thermal diffusion. It is believed that when component (C) collides with an excited luminescent material, the excitation energy of the luminescent material is transferred to the molecule of component (C), thereby deactivating the luminescent material in the excited state, and thus the fluorescence quantum yield of component (A) decreases. In the present invention, X in general formula (2) is CR 7 In this case, by making R 1 ~R 7 At least one of the substituents is a substituent with a moderately large volume, thereby being able to suppress the decrease in the fluorescence quantum yield of the component (A). 2 , R 5 and R 7 At least one of them is a substituent with a moderately large volume, and R is particularly preferred. 2 , R 5 and R 7 All are moderately bulky substituents.

[0094] As R 2 and R 5 The substituent having a moderately large volume may be, for example, an alkyl group, a cycloalkyl group, a heterocyclic group, an alkenyl group, a cycloalkenyl group, an alkynyl group, an alkoxy group, an alkylthio group, an aryl ether group, an aryl thioether group, an aryl group, a heteroaryl group, a carbonyl group, a carboxyl group, an oxycarbonyl group, an ester group, a carbamoyl group, an amino group, a nitro group, a silyl group, a siloxane group, a boron group, a phosphine oxide group, etc. Among them, an alkyl group, a cycloalkyl group, an aryl group, and an ester group are more preferred.

[0095] In addition, as R 7 An example of a substituent having a moderately large volume is preferably a structure represented by the following general formula (3). That is, X in the general formula (2) is CR 7 In the case of R 7 Preferred are groups represented by the general formula (3).

[0096] [Chemical formula 5]

[0097]

[0098] In the general formula (3), r is 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, a halogen, a cyano group, an aldehyde group, a carbonyl group, a carboxyl group, an oxycarbonyl group, a carbamoyl group, an amino group, a nitro group, a silyl group, a siloxane group, a boron group, and a phosphine oxide group. k is an integer of 1 to 3. When k is 2 or more, each r may be the same or different.

[0099] In the general formula (3), r is preferably a substituted or unsubstituted aryl group. Among the aryl groups, phenyl and naphthyl can be particularly mentioned as preferred examples. These aryl groups may be substituted by one or more groups selected from the group consisting of an alkyl group, a heterocyclic group, an alkenyl group, a hydroxyl group, an alkoxy group, an aryl ether group, an aryl group, a heteroaryl group, a halogen group, a cyano group, a carboxyl group, an ester group, an oxycarbonyl group and an alkoxy group.

[0100] In the general formula (3), at least one of r is preferably substituted with an alkyl group or an aryl group. In this case, particularly preferred examples of the alkyl group include a methyl group, an ethyl group, and a tert-butyl group.

[0101] When r in the general formula (3) is an aryl group, k in the general formula (3) is preferably 1 or 2, more preferably 2, from the viewpoint of further suppressing a decrease in the fluorescence quantum yield of the component (A) caused by the component (C).

[0102] In addition, from the viewpoint of controlling the fluorescence wavelength, the absorption wavelength or improving the compatibility with the solvent, r in the general formula (3) is preferably a substituted or unsubstituted alkyl, a substituted or unsubstituted alkoxy, or a halogen. Among them, methyl, ethyl, tert-butyl, and methoxy are more preferred. From the viewpoint of dispersibility, tert-butyl and methoxy are particularly preferred as r. In this case, quenching caused by the aggregation of molecules can be prevented.

[0103] In addition, as another embodiment of the compound represented by the general formula (2), R 1 ~R 7 At least one of is an electron withdrawing group. It is particularly preferred that (1) R 1 ~R 6 At least one of R is an electron withdrawing group; (2) R 7 is an electron-withdrawing group; or (3) R 1 ~R 6 At least one of them is an electron withdrawing group and R 7 It is an electron withdrawing group.

[0104] There are two reasons for this. First, the first reason is to further improve the light durability improvement effect of the color conversion composition brought by the (C) component. That is, by introducing an electron-withdrawing group into the pyrromethene skeleton, the electron density of the pyrromethene skeleton can be greatly reduced, and the reaction rate of the compound having the pyrromethene skeleton and singlet oxygen can be reduced. As a result, the reaction rate of singlet oxygen being deactivated by the (C) component is faster than the reaction rate of singlet oxygen oxidation of the (A) component, and as a result, the light durability improvement effect of the color conversion composition brought by the (C) component becomes more significant.

[0105] The second reason is to suppress the formation of a charge transfer complex between component (A) and component (C). That is, component (C) used in the color conversion composition of the present invention has an electron-withdrawing group, so it is easy to act as an acceptor, and therefore sometimes interacts with an electron-donating compound to cause charge transfer. As the influence caused by charge transfer, there can be cited a decrease in color reproducibility due to the emission wavelength obtained by color conversion using the light-emitting material becoming a long wavelength; a decrease in the fluorescence quantum yield of the light-emitting material due to a decrease in emission intensity; etc. In order to suppress these, it is effective to introduce an electron-withdrawing group on the light-emitting material side. As a result, it is possible to prevent component (A) as a light-emitting material from approaching component (C) by electrostatic repulsion, and to reduce the energy level of the HOMO (Highest occupied molecular orbital) of the light-emitting material to suppress the charge transfer from component (A) to component (C).

[0106] The so-called electron-withdrawing group, also known as an electron-accepting group, is an atomic group that uses the inductive effect and the resonance effect to attract electrons from the substituted atomic group in the organic electronic theory. As the electron-withdrawing group, there can be cited a group that takes a positive value as the substituent constant (σp(para)(σp(para))) of the Hammett equation. The substituent constant (σp(para)) of the Hammett equation can be cited from the fifth edition of the revised version of the basic version of the Chemical Handbook (II-380 pages) (Chemical Handbook Basic Version Revised Version 5 (II-380 pages)). It should be noted that there are also examples where the phenyl group also takes a positive value as mentioned above, but the electron-withdrawing group of the present invention does not include the phenyl group.

[0107] Examples of electron withdrawing groups include: -F (σp: +0.20), -Cl (σp: +0.28), -Br (σp: +0.30), -I (σp: +0.30), -CO2R 12 (σp:R 12 +0.45 for ethyl), -CONH 2 (σp:+0.38)、-COR 12 (σp:R 12 +0.49 for methyl), -CF3 (σp: +0.51), -SO2R 12 (σp:R 12 When it is a methyl group, it is +0.69), -NO2 (σp: +0.81), etc. 12 Each independently represents a hydrogen atom, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 1 to 30 carbon atoms. Specific examples of these groups include the same examples as described above.

[0108] Preferred electron-withdrawing groups include fluorine, fluorine-containing aryl groups, fluorine-containing heteroaryl groups, fluorine-containing alkyl groups, substituted or unsubstituted acyl groups, substituted or unsubstituted ester groups, substituted or unsubstituted amide groups, substituted or unsubstituted sulfonyl groups or cyano groups, because these groups are not easily chemically decomposed.

[0109] As more preferred electron-withdrawing groups, fluorinated alkyl groups, substituted or unsubstituted acyl groups, substituted or unsubstituted ester groups or cyano groups can be cited. The reason is that these groups can prevent concentration quenching and improve the quantum yield of luminescence. Particularly preferred electron-withdrawing groups are substituted or unsubstituted ester groups.

[0110] Among the compounds represented by the general formula (2), R 1 ~R 6 At least one of them is an electron withdrawing group, X is CR 7 , the R 7 It is a group represented by the general formula (3).

[0111] An example of the compound represented by the general formula (2) is shown below, but the compound is not limited thereto.

[0112] [Chemical formula 6]

[0113]

[0114] [Chemical formula 7]

[0115]

[0116] [Chemical formula 8]

[0117]

[0118] [Chemical formula 9]

[0119]

[0120] [Chemical formula 10]

[0121]

[0122] [Chemical formula 11]

[0123]

[0124] [Chemical formula 12]

[0125]

[0126] [Chemical formula 13]

[0127]

[0128] [Chemical formula 14]

[0129]

[0130] The compound represented by the general formula (2) can be synthesized by the method described in, for example, Japanese Patent Publication No. 8-509471 and Japanese Patent Publication No. 2000-208262. That is, by reacting a pyrromethene compound with a metal salt in the presence of a base, a pyrromethene metal complex as the target can be obtained. In addition, regarding the synthesis of pyrromethene-boron fluoride complexes, reference can be made 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. to synthesize the compound represented by the general formula (2). For example, the following method can be used: in the presence of phosphorus oxychloride, a compound represented by the following general formula (4) and a compound represented by the following general formula (5) are heated in 1,2-dichloroethane, and then in the presence of triethylamine, a compound represented by the following general formula (6) is reacted in 1,2-dichloroethane to obtain a compound represented by the general formula (2). However, the present invention is not limited thereto. Here, R 1 ~R 9 The same as the above description. J represents a halogen.

[0131] [Chemical formula 15]

[0132]

[0133] In addition, when introducing an aryl group or a heteroaryl group, a method of generating a carbon-carbon bond by a coupling reaction of a halogenated derivative with a boric acid or a boronate derivative can be cited, but the present invention is not limited thereto. Similarly, when introducing an amino group or a carbazole group, a method of generating a carbon-nitrogen bond by a coupling reaction of a halogenated derivative with an amine or a carbazole derivative in the presence of a metal catalyst such as palladium can also be cited, but the present invention is not limited thereto.

[0134] In addition to the compound represented by the general formula (2), the color conversion composition according to the embodiment of the present invention may contain other compounds as needed. For example, in order to improve the energy transfer efficiency from the excitation light to the compound represented by the general formula (2), an auxiliary dopant such as rubrene may be contained. In addition, when it is desired to add a luminescent color other than the luminescent color of the compound represented by the general formula (2), the above-mentioned organic luminescent materials, inorganic phosphors, fluorescent pigments, fluorescent dyes, quantum dots and other known luminescent materials may also be contained.

[0135] Examples of organic light-emitting materials other than the compound represented by the general formula (2) are shown below, but the present invention is not particularly limited to these.

[0136] [Chemical formula 16]

[0137]

[0138] In the color conversion composition according to the embodiment of the present invention, the component (A) preferably contains a luminescent material (hereinafter referred to as "luminescent material (a)") that exhibits luminescence with a peak wavelength observed in a region of 500 nm to less than 580 nm by using excitation light with a wavelength in the range of 400 nm to 500 nm. Hereinafter, luminescence with a peak wavelength observed in a region of 500 nm to less than 580 nm is referred to as "green luminescence". Generally speaking, the greater the energy of the excitation light, the easier it is to cause decomposition of the material. However, the excitation light with a wavelength in the range of 400 nm to 500 nm has a relatively small excitation energy. Therefore, green luminescence with good color purity can be obtained without causing decomposition of the luminescent material (a) in the color conversion composition.

[0139] In addition, in the color conversion composition according to an embodiment of the present invention, the component (A) preferably contains at least one of the following luminescent materials (a) and luminescent materials (b). As described above, the luminescent material (a) is a luminescent material that exhibits luminescence with a peak wavelength of 500 nm or more and less than 580 nm by using excitation light with a wavelength in the range of 400 nm or more and 500 nm or less. The luminescent material (b) is a luminescent material that exhibits luminescence with a peak wavelength observed in a region of 580 nm or more and 750 nm or less by being excited by at least one of the excitation light with a wavelength in the range of 400 nm or more and 500 nm or the luminescence from the luminescent material (a). Hereinafter, luminescence with a peak wavelength observed in a region of 580 nm or more and 750 nm or less is referred to as "red luminescence".

[0140] A portion of the excitation light in the wavelength range of 400 nm to 500 nm partially transmits the color conversion sheet of the embodiment of the present invention. Therefore, when a blue LED with a sharp emission peak is used, a sharp emission spectrum is exhibited for each of the blue, green, and red colors, and white light with good color purity can be obtained. As a result, a more vivid and larger color gamut can be efficiently formed, especially in displays. In addition, in lighting applications, compared with the currently mainstream white LED obtained by combining a blue LED with a yellow phosphor, the emission characteristics in the green and red regions are improved, and therefore, a preferred white light source with improved color rendering can be obtained.

[0141] Examples of the light-emitting material (a) include coumarin derivatives such as coumarin 6, coumarin 7, and coumarin 153, cyanine derivatives such as indocyanine green, fluorescein, fluorescein isothiocyanate, and fluorescein derivatives such as carboxyfluorescein diacetate, phthalocyanine derivatives such as phthalocyanine green, perylene derivatives such as diisobutyl-4,10-dicyanoperylene-3,9-dicarboxylate, pyrromethene derivatives, stilbene derivatives, oxazine derivatives, naphthalimide derivatives, pyrazine derivatives, benzimidazole derivatives, benzoxazole derivatives, benzothiazole derivatives, imidazopyridine derivatives, azole derivatives, compounds having a condensed aromatic ring such as anthracene, derivatives thereof, aromatic amine derivatives, and organic metal complex compounds. Component (A) may contain two or more of these as the light-emitting material (a).

[0142] Among these compounds, pyrromethene derivatives are particularly preferred because they can provide high fluorescence quantum yields and have good durability of color purity. Among pyrromethene derivatives, compounds represented by the general formula (2) are preferred because they emit light with high color purity.

[0143] Examples of the light-emitting material (b) include cyanine derivatives such as 4-dicyanomethylidene-2-methyl-6-(p-dimethylaminophenylvinyl)-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, and compounds having a condensed aromatic ring such as porphyrin derivatives, pyrromethene derivatives, oxazine derivatives, pyrazine derivatives, tetracene, dibenzodiindenoperylene, derivatives thereof, and organic metal complex compounds. Component (A) may contain two or more of these as the light-emitting material (b).

[0144] Among these compounds, pyrromethene derivatives are particularly preferred because they can provide high fluorescence quantum yields and have good durability of color purity. Among pyrromethene derivatives, compounds represented by the general formula (2) are preferred because they emit light with high color purity.

[0145] In addition, as the organic light-emitting material contained in the component (A), a compound that emits delayed fluorescence can also be preferably used. Compounds that emit delayed fluorescence are explained in "The Most Advanced Organic EL" (edited by Chiba Ya Andachi and Hiroshi Fujimoto, published by CMC) on pages 87 to 103. In this document, the following description is made: By making the energy levels of the excited singlet state and the excited triplet state of the light-emitting material close, the reverse energy transfer from the excited triplet state with a low transition probability to the excited singlet state occurs efficiently, showing thermally activated delayed fluorescence (Thermally Activated delayed Fluorescence, TADF). In addition, Figure 5 in this document illustrates the generation mechanism of delayed fluorescence. The luminescence of delayed fluorescence can be confirmed by transition PL (Photo Luminescence) measurement.

[0146] Generally, fluorescence is emitted from an excited singlet state generated after the luminescent material is excited by light, and the excited triplet state of the luminescent material generated by intersystem crossing is thermally deactivated at room temperature. Therefore, no fluorescence is emitted from the excited triplet state of the luminescent material. On the other hand, as described above, even if the compound emitting delayed fluorescence generates an excited triplet state, it emits fluorescence after being quickly converted to an excited singlet state. Therefore, the excited triplet state that cannot contribute to luminescence in a conventional fluorescent luminescent material can also contribute to fluorescent luminescence. Therefore, high-efficiency luminescence can be obtained. In addition, the excited triplet state of the compound emitting delayed fluorescence is quickly converted to an excited singlet state. Therefore, singlet oxygen is not easily generated, and as a result, it can be expected that the durability of the color conversion composition containing the compound is also improved. It should be noted that the generation of excited triplet states and singlet oxygen of the luminescent material and their relationship with durability are described in detail in the item <(C) component: compound represented by general formula (1)>.

[0147] The compound emitting delayed fluorescence needs to make the energy level of the excited singlet state close to the energy level of the excited triplet state. As a molecular design to achieve this, the electron-donating skeleton is bonded to the electron-accepting skeleton in the same molecule, thereby separating the HOMO (Highest occupied molecular orbital) orbit from the LUMO (Lowest unoccupied molecular orbital) orbit in the molecule, which is effective. The electron-donating skeleton and the electron-accepting skeleton can be directly bonded or bonded via a linking group. As a linking group in this case, it is preferably a skeleton comprising an aromatic hydrocarbon.

[0148] As the electron-donating skeleton, for example, a skeleton having an amine nitrogen atom can be cited. Among them, a skeleton containing diarylamine, triarylamine, a skeleton containing carbazole, a skeleton containing benzocarbazole, a skeleton containing indolecarbazole, a skeleton containing phenoxazine, or a skeleton containing phenothiazine is preferred. Among them, a skeleton containing carbazole, a skeleton containing benzocarbazole, a skeleton containing indolecarbazole, or a skeleton containing phenoxazine is more preferred, and a skeleton containing carbazole or a skeleton containing phenoxazine is further preferred.

[0149] On the other hand, as electron accepting skeleton, generally can enumerate the skeleton comprising the substituent (i.e. electron withdrawing group) with electron withdrawing.In the skeleton comprising electron withdrawing group, preferably comprising the skeleton of heteroaryl with partial structure formed by carbon atom and nitrogen atom being bonded by double bond, comprising the skeleton of fluorinated substituent, comprising cyano, comprising carbonyl, comprising sulfoxide or disulfoxide skeleton or comprising phosphine oxide skeleton etc..Wherein, from the viewpoint of the stability of compound, more preferably comprising the skeleton of heteroaryl with partial structure formed by carbon atom and nitrogen atom being bonded by double bond, comprising the skeleton of fluorinated substituent or comprising cyano skeleton etc.

[0150] Among the skeletons of heteroaryl groups having a partial structure in which a carbon atom and a nitrogen atom are bonded by double bonds, specifically, skeletons containing pyridine, pyrimidine, pyrazine, triazine, quinoline, quinoxaline, quinazoline, or phenanthroline are preferred. Among them, skeletons containing pyrimidine, triazine, quinoxaline, or quinazoline are more preferred, and skeletons containing triazine are further preferred.

[0151] In the skeleton comprising a fluorinated substituent, a skeleton comprising a fluorinated aryl or fluoroalkyl is more preferably included. As the skeleton comprising a fluorinated aryl, a fluorinated benzene ring is preferably included, specifically, a skeleton comprising fluorobenzene, difluorobenzene, trifluorobenzene, tetrafluorobenzene or pentafluorobenzene is more preferably included. As the skeleton comprising a fluoroalkyl, a skeleton comprising a benzene ring substituted with trifluoromethyl is preferably included, wherein a skeleton comprising mono(trifluoromethyl)benzene or bis(trifluoromethyl)benzene is more preferably included.

[0152] Among the skeletons having a cyano group, a skeleton containing cyanobenzene, dicyanobenzene, or tricyanobenzene is more preferred.

[0153] An example of a compound in which the electron-donating skeleton and the electron-accepting skeleton are bonded is shown below, but the compound is not particularly limited thereto. It is noted that the compound shown here is known to emit delayed fluorescence from prior literature.

[0154] [Chemical formula 17]

[0155]

[0156] As the compound emitting delayed fluorescence, in addition to the compound in which the electron donating skeleton and the electron accepting skeleton are bonded to each other, the compound represented by the following general formula (11) and the compound represented by the general formula (12) can be more preferably used.

[0157] [Chemical formula 18]

[0158]

[0159] [Chemical formula 19]

[0160]

[0161] In the general formula (11) or (12), Ring Za, Ring Zb and Ring Zc are each independently a substituted or unsubstituted aromatic ring having 6 to 40 ring carbon atoms, or a substituted or unsubstituted heteroaromatic ring having 6 to 40 ring carbon atoms.

[0162] In the general formula (11), Z 1 and Z 2 Each is independently an oxygen atom, NRa (a nitrogen atom having a substituent Ra) or a sulfur atom. 1 In the case of NRa, the substituent Ra may be bonded to the ring Za or the ring Zb to form a ring, or may not form a ring. 2 In the case of NRa, the substituent Ra may be bonded to the ring Za or the ring Zc to form a ring. E is a boron atom, a phosphorus atom, SiRa (silicon atom having a substituent Ra), P=O or P=S.

[0163] In the general formula (12), E 1 and E 2 Each is independently BRa (boron atom having substituent Ra), PRa (phosphorus atom having substituent Ra), SiRa2 (silicon atom having two substituent Ra), P(=O)Ra2 (phosphine oxide having two substituent Ra) or P(=S)Ra2 (phosphine sulfide having two substituent Ra), C=O (carbonyl), S(=O) or S(=O)2. 1 In the case of BRa, PRa, SiRa2, P(=O)Ra2 or P(=S)Ra2, the substituent Ra may be bonded to the ring Za or the ring Zb to form a ring. 2 In the case of BRa, PRa, SiRa2, P(=O)Ra2 or P(=S)Ra2, the substituent Ra may be bonded to the ring Za or the ring Zc to form a ring.

[0164] The above-mentioned substituents Ra are each independently selected from hydrogen atoms, 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, aryl thioether groups, halogen, cyano groups, aldehyde groups, carbonyl groups, carboxyl groups, oxycarbonyl groups, ester groups, carbamoyl groups, amide groups, sulfonyl groups, sulfonate groups, sulfonamide groups, amino groups, imino groups, nitro groups, silyl groups, siloxane groups, boron groups, phosphine oxide groups, perfluoroalkyl groups, and condensed rings and aliphatic rings formed between adjacent substituents. In addition, the substituents Ra can be further substituted by substituents selected from these. The substituents substituted by the substituents Ra can be further substituted by substituents selected from these.

[0165] Among all the above-mentioned groups, as the substituent in the case of being substituted, there can be mentioned an alkyl group, a cycloalkyl group, a heterocyclic group, an alkenyl group, a cycloalkenyl group, an alkynyl group, an aryl group, a heteroaryl group, a hydroxyl group, a thiol group, an alkoxy group, an alkylthio group, an aryl ether group, an aryl thioether group, a halogen, a cyano group, an aldehyde group, a carbonyl group, a carboxyl group, an oxycarbonyl group, a perfluoroalkyl group, an amide group, a sulfonyl group, a sulfonate group, a sulfonamide group, an amino group, an imino group, a nitro group, a silyl group, a siloxane group, a boron group or a phosphine oxide group, etc. In addition, these substituents may be further substituted by the above-mentioned substituents.

[0166] Examples of the substituted or unsubstituted aromatic ring having 6 to 40 ring carbon atoms in the ring Za, ring Zb and ring Zc include a benzene ring, a naphthalene ring, a phenanthrene ring, Aromatic hydrocarbon rings such as anthracene ring, pyrene ring, etc. are preferably used. Among them, from the viewpoint of ensuring solubility, a benzene ring is preferred. In addition, as a heteroaromatic ring having 6 to 40 ring carbon atoms, an aromatic heteroaromatic ring structure such as a pyridine ring, a quinoline ring, and a phenanthroline ring can be cited. Among them, from the viewpoint of the ease of obtaining the raw materials and the difficulty of synthesis, a pyridine ring is preferred.

[0167] In addition, in the general formula (11) and the general formula (12), the substituent Ra is preferably a group having 6 to 40 carbon atoms including the substituent. The substituent Ra is more preferably a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group. Examples of the substituted or unsubstituted aryl group include substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, etc. Among them, substituted or unsubstituted phenyl is more preferred.

[0168] In addition, the luminescence spectrum of the compound represented by the general formula (11) or the general formula (12) is sharper than that of the compound formed by bonding the electron-donating skeleton to the electron-accepting skeleton due to the multiple resonance effect of the compound. Therefore, by making the compound emitting delayed fluorescence a compound represented by the general formula (11) or the general formula (12), luminescence with high color purity can be obtained. That is, the compound represented by the general formula (11) or the general formula (12) is conducive to improving the color gamut of the display, and is therefore preferably used as a compound emitting delayed fluorescence. In addition, with respect to the compound represented by the general formula (11) or the general formula (12), since ring Za, ring Zb, and ring Zc are present around the E atom in the general formula (11) or the general formula (12) where the LUMO orbit is mainly locally present, it is possible to protect the E atom, i.e., most of the LUMO orbit. Therefore, the electronic interaction caused by the collision between the compound represented by the general formula (11) or the general formula (12) and the (C) component can be suppressed. Thus, the high fluorescence quantum yield originally possessed by the compound represented by the general formula (11) or the general formula (12) can be maintained, and the effect of improving durability brought by the (C) component can be exerted. Based on this point, the compound represented by the general formula (11) or the general formula (12) is preferably used as a compound emitting delayed fluorescence. It should be noted that the above-mentioned E atom is an atom of E in the general formula (11), and is an atom of E in the general formula (12). 1 and E 2 of each atom.

[0169] Furthermore, it is more preferred that the substituent Ra in each of the general formula (11) and the general formula (12) forms a structure that is bonded to at least one of the rings Za, Zb, and Zc. This is because by bonding the substituent Ra to at least one of the rings Za, Zb, and Zc, it is expected that E in the general formula (11) and E in the general formula (12) will be 1 and E 2 The stereoprotection effect is further improved, and the effect of inhibiting the decrease in fluorescence quantum yield is further improved.

[0170] An example of the compound represented by the general formula (11) or (12) is shown below. However, the compound is not particularly limited thereto.

[0171] [Chemical formula 20]

[0172]

[0173] The content of the component (A) in the color conversion composition according to the embodiment of the present invention can be selected based on the molar absorption coefficient, fluorescence quantum yield and absorption intensity at the excitation wavelength of the compound, as well as the thickness and transmittance of the sheet to be produced. Here, the content of the component (A) refers to the total content thereof when the color conversion composition of the present invention contains two or more components (A). The content of the component (A) is preferably 1.0×10 -2 Parts by weight to 5 parts by weight.

[0174] In addition, when the color conversion composition of the present invention contains both the light-emitting material (a) that emits green light and the light-emitting material (b) that emits red light, part of the green light is converted into red light. Therefore, it is preferred that the content of the light-emitting material (a) is less than 1:1. a , and the content of luminescent material (b) w b w a ≥w b In addition, the content ratio w of these luminescent materials (a) and luminescent materials (b) is a :w b The preferred ratio is 200:1 to 3:1. a And content w b It is a weight percentage relative to the weight of (B) component.

[0175] <Component (B): Binder Resin>

[0176] The color conversion composition of the present invention contains a binder resin as the component (B). The binder resin is a substance that forms a continuous phase, and any material having excellent molding processability, transparency, heat resistance, etc. may be used. Examples of the binder resin include the following known substances: photocurable resist materials having reactive vinyl groups such as acrylic acid, methacrylic acid, polyvinyl cinnamate, and ring rubber, epoxy resins, silicone resins (including organic polysiloxane 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, aromatic polyolefin resins, and the like. In addition, copolymerized resins thereof may also be used as the binder resin. By appropriately designing these resins, a binder resin useful for the color conversion composition and color conversion sheet of the present invention can be obtained.

[0177] Among these resins, thermoplastic resins are more preferred from the perspective of easy molding processes such as sheeting. Among thermoplastic resins, epoxy resins, silicone resins, acrylic resins, ester resins, olefin resins or mixtures thereof can be preferably used from the perspectives of transparency and heat resistance. In addition, from the perspective of durability, particularly preferred thermoplastic resins are acrylic resins, ester resins, and cycloolefin resins.

[0178] Specific examples of suitable binder resins include binder resins described in International Publication No. 2016 / 190283, International Publication No. 2017 / 61337, International Publication No. 2018 / 43237, International Publication No. 2019 / 21813, and International Publication No. 2019 / 188019.

[0179] In addition, the binder resin may be added with dispersants and leveling agents for stabilizing the coating film as additives, and may be added with bonding aids such as silane coupling agents as modifiers for the sheet surface. In addition, inorganic particles such as silica particles and organosilicon microparticles may be added to the binder resin as a color conversion material sedimentation inhibitor.

[0180] <Component (C): Compound represented by general formula (1)>

[0181] In order to prevent the degradation of the luminescent material contained as the component (A) and to suppress the change in chromaticity over time to improve durability, the color conversion composition according to an embodiment of the present invention contains a compound represented by the general formula (1) described below as the component (C). The component (C) has a function as a singlet oxygen quencher.

[0182] A singlet oxygen quencher is a compound that captures and deactivates singlet oxygen formed by activation of ground state oxygen molecules using excitation energy. The presence of a singlet oxygen quencher in a color conversion composition can prevent the luminescent material in the color conversion composition from being oxidatively degraded by singlet oxygen. The following describes the generation mechanism of singlet oxygen and the deactivation mechanism of singlet oxygen using a singlet oxygen quencher.

[0183] First, the generation mechanism of singlet oxygen is described. It is believed that singlet oxygen is not easily generated by directly photoexciting triplet oxygen in the ground state. The reason is that the transition from triplet oxygen in the ground state to singlet oxygen in the excited state is a spin-forbidden transition, so the transition probability is very low. Therefore, it is believed that the generation of singlet oxygen in the color conversion composition of the present invention is caused by the sensitization of the pigment.

[0184] That is, it is believed that singlet oxygen is produced by the exchange of electrons and energy between the luminescent material in the excited triplet state and the triplet oxygen molecule in the ground state. It is believed that its generation mechanism is as follows. First, by light excitation, the luminescent material becomes an excited singlet state from the singlet ground state, and then, by intersystem crossing, a part of the luminescent material becomes an excited triplet state from the excited singlet state. The transition from the excited triplet state of the generated luminescent material to the singlet ground state is a spin-forbidden transition, and therefore, the transition probability is usually low. However, in the case of coexistence of triplet oxygen in the ground state, by being accompanied by the excitation of the triplet oxygen from the ground state to the singlet oxygen in the excited state, the spin prohibition is released, and the luminescent material can be rapidly deactivated from the excited triplet state to the singlet ground state.

[0185] This mechanism is called the Dexter mechanism (electron exchange mechanism). In order for the Dexter mechanism to proceed, electron exchange via the overlap of wave functions between molecules is required. Therefore, it is believed that direct collision between energy donor molecules (in this case, luminescent materials in the excited triplet state) and energy acceptor molecules (in this case, triplet oxygen in the ground state) is required.

[0186] The following is an explanation of the deactivation mechanism of singlet oxygen using a singlet oxygen quencher. The transition from excited singlet oxygen to ground triplet oxygen is a spin-forbidden transition, and therefore, the transition probability is generally low. Here, in the presence of a singlet oxygen quencher, similarly to the above-mentioned singlet oxygen generation mechanism, the spin-forbidden transition is released by the excitation of the singlet oxygen quencher from the ground state to the triplet oxygen quencher in the excited state, and the singlet oxygen can be rapidly deactivated to ground triplet oxygen.

[0187] In order for a certain compound to function as a singlet oxygen quencher, it is preferred that the compound be excited with energy smaller than the excitation energy of singlet oxygen. In the present invention, the compound represented by the general formula (1), which is the component (C) in the color conversion composition, functions as a singlet oxygen quencher, thereby improving the durability of the luminescent material, which is the component (A) in the color conversion composition. Preferred specific examples of the compound represented by the general formula (1) are shown below.

[0188] [Chemical formula 21]

[0189]

[0190] As described above, the compound represented by the general formula (1) is an organic acid salt of copper. Organic acid salts of copper can efficiently absorb the excitation energy of singlet oxygen. Therefore, it is believed that the compound represented by the general formula (1) effectively acts as a singlet oxygen quencher. On the other hand, even if a metal other than copper, such as nickel, is used as a singlet oxygen quencher, it is not possible to efficiently absorb the excitation energy of singlet oxygen, so the durability of the luminescent material is insufficient.

[0191] Generally, it is known that metal complexes undergo ligand exchange, and the speed of the ligand exchange depends on multiple factors such as the size of the activation energy barrier between the metal complexes, the ligand-field stabilization energy (LFSE), and the electrostatic effect. Therefore, when considering the stability of metal complexes, these multiple factors need to be considered. As for the classification of hard acid / base and soft acid / base (hard acid, hard base; soft acid, soft base, HSAB), they are empirically divided into acids and bases according to the stability of the complex. Since hard acids tend to bond with hard bases, and soft acids tend to bond with soft bases, these bonding tendencies are particularly useful for predicting the stability of metal complexes. Hard acids that are not easily polarized form complexes with highly electron-donating hard bases that are mainly composed of ionic interactions, which are much more important than soft acids that are easily polarized and soft bases that form covalent bonds.

[0192] Cu is stable as copper (Cu) ions 2+ Classified as an intermediate acid, Cu 1+ It is classified as a soft acid. Usually, in order to obtain a Cu complex with high stability, it is preferred that the coordinating atoms to the central metal are N, S, P, and C. However, the color of the Cu complex is mostly black to dark blue when the coordinating atoms are N and P. Therefore, when the Cu complex is used as a singlet oxygen quencher, the Cu complex absorbs the excitation light and the color-converted light. This leads to a decrease in the fluorescence quantum yield. Therefore, a singlet oxygen quencher of a stable Cu complex coordinated by O atoms and S atoms is required.

[0193] In the compound represented by the above general formula (1), X 1 and X 2 Each independently is O or S. R a ~R c each independently selected from a hydrogen atom, an alkyl group, a cycloalkyl group, a heterocyclic group, an alkenyl group, a cycloalkenyl group, an alkynyl group, a hydroxyl group, an alkoxy group, a thiol group, an alkylthio group, an aryl ether group, an aryl thioether group, an aryl group, a heteroaryl group, a halogen group, a cyano group, an aldehyde group, an oxycarbonyl group, a carbamoyl group, an amino group, a nitro group, a silyl group, a siloxane group, a boron group, a phosphine oxide group, -C(=O)R 101 、-S(=O)R 102 R 103 、-S(=O)R 104 、-S(=O)2R 105 , and a group consisting of a condensed ring or an aliphatic ring formed with adjacent substituents. 101 ~R 105 is a substituent, R 102 and R 103can be fused to each other to form a ring. a ~R c At least one of them is an electron withdrawing group. n is an integer of 1-4.

[0194] In the compound represented by the general formula (1), each substituent has the same meaning as described in the above-mentioned section <Component (A): light-emitting material>, and is additionally described below.

[0195] By making R a ~R c At least one of the electron-withdrawing groups is an electron-withdrawing group, which can reduce the electron-donating property of the coordinating atom close to the electron-withdrawing group. As a result, the bonding between Cu and the ligand in the general formula (1) can be stabilized. a ~R c The remaining groups except the electron withdrawing group are not particularly limited, even if they are electron donating groups such as butyl groups, as long as they can ensure stability sufficient to obtain good moisture resistance.

[0196] For example, acetylacetone, a multidentate ligand containing an O atom, is a typical hard base, and its bond with Cu is relatively weak. Therefore, in a high temperature and high humidity environment, the ligand falls off due to excess water, and black Cu is formed by decomposition. In order to prevent this, for the compound represented by the general formula (1), by a ~R c By controlling the electron-donating property to Cu by using at least one of the electron-withdrawing groups in the ligand, the bonding between Cu and the ligand can be stabilized. Therefore, the reaction between the ligand and water in a high humidity environment is suppressed, so a singlet oxygen quencher with high humidity resistance can be obtained.

[0197] Cu may have a valence of 1 to 4. That is, in the compound represented by the general formula (1), n ​​is an integer of 1 to 4, preferably an integer of 1 to 3, and more preferably an integer of 1 to 2. This is because Cu 2+ It is classified as an intermediate acid, Cu 1+ It is classified as a soft acid. In the general formula (1), R 101 ~R 105 There are no particular limitations, but it may be an electron-donating group such as a butyl group or an electron-withdrawing group such as a perfluoroalkyl group. It is preferred that the solubility of the singlet oxygen quencher be improved by these groups.

[0198] The electron withdrawing group in the compound represented by the general formula (1) is preferably selected from the group of electron withdrawing groups shown in the above-mentioned <(A) component: light-emitting material>, wherein a group containing fluorine atoms that interacts less with Cu is more preferred, and a group having 4 or more fluorine atoms is further preferred. Furthermore, the group having 4 or more fluorine atoms is particularly preferably a perfluoroalkyl group. In order to improve the solubility of the singlet oxygen quencher, the perfluoroalkyl group as the electron withdrawing group is preferably a group having 2 or more carbon atoms.

[0199] In addition, from the viewpoint that singlet oxygen and the singlet oxygen quencher are easily accessible, in the general formula (1), R a ~R c At least one of them is a hydrogen atom, and more preferably R b A hydrogen atom.

[0200] Furthermore, in the general formula (1), X, which is an atom coordinated to Cu, 1 and X 2 It is preferably an atom with unpaired electrons to make the bond with Cu strong. 1 and X 2 Each independently is O or S. In particular, considering the advantage of the singlet oxygen quencher itself having a light color, X 1 and X 2 Preferably both are O.

[0201] In the compound represented by the general formula (1), R a ~R c At least one of them is an electron-withdrawing group as described above. The electron-withdrawing group is preferably a group containing fluorine atoms, more preferably a group having 4 or more fluorine atoms, and further preferably a perfluoroalkyl group having 2 or more carbon atoms. Furthermore, R is particularly preferably a ~R c R b is a hydrogen atom, X 1 and X 2 Both are O.

[0202] Preferred specific examples of the compound represented by the general formula (1) are shown below.

[0203] [Chemical formula 22]

[0204]

[0205] <Other additives>

[0206] The color conversion composition according to the embodiment of the present invention may contain fillers, antioxidants, processing and heat stabilizers, light resistance stabilizers such as ultraviolet absorbers, dispersants for stabilizing the coating film, leveling agents, scattering agents, plasticizers, crosslinking agents such as epoxy compounds, curing agents such as amines, acid anhydrides, and imidazoles, pigments, and other additives such as silane coupling agents as film surface modifiers, in addition to the above-mentioned components (A), (B), and (C).

[0207] Examples of fillers include fine particles such as fumed silica, glass powder, and quartz powder, titanium oxide, zirconium oxide, barium titanate, zinc oxide, and silicone fine particles. The color conversion composition of the present invention may contain one or more of these as fillers.

[0208] Examples of the antioxidant include phenolic antioxidants such as 2,6-di-tert-butyl-p-cresol and 2,6-di-tert-butyl-4-ethylphenol. The color conversion composition of the present invention may contain one or more of these antioxidants as an antioxidant.

[0209] Examples of the processing and heat stabilizers include phosphorus stabilizers such as tributyl phosphite, tricyclohexyl phosphite, triethylphosphine, and diphenylbutylphosphine. The color conversion composition of the present invention may contain one or more of these as processing and heat stabilizers.

[0210] Examples of the light resistance stabilizer include benzotriazoles such as 2-(5-methyl-2-hydroxyphenyl)benzotriazole and 2-[2-hydroxy-3,5-bis(α,α-dimethylbenzyl)phenyl]-2H-benzotriazole. The color conversion composition of the present invention may contain one or more of these as the light resistance stabilizer.

[0211] The content of these additives in the color conversion composition according to the embodiment of the present invention can also be set according to the molar absorption coefficient, fluorescence quantum yield and absorption intensity at the excitation wavelength of the compound, and the thickness and transmittance of the prepared sheet. The content of the additives is preferably 1.0×10 -1 More than 10 parts by weight and less than 10 parts by weight.

[0212] <Solvent>

[0213] The color conversion composition according to the embodiment of the present invention may further contain a solvent in addition to the above-mentioned components (A), (B) and (C). As the solvent, it is preferred that the viscosity of the resin in the flowing state be adjusted and that the luminescence and durability of the luminescent material be not excessively affected. As such a solvent, for example, water, 2-propanol, ethanol, toluene, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, hexane, acetone, ethyl acetate, butyl acetate, terpineol, Texanol, methyl cellosolve, ethyl cellosolve, butyl carbitol, butyl carbitol acetate, 1-methoxy-2-propanol, propylene glycol monomethyl ether acetate, etc. may be cited. The color conversion composition of the present invention may contain one or more of these as a solvent. Among these solvents, ethyl acetate is particularly preferred because it does not affect the deterioration of the compound represented by the general formula (2) and has a small amount of residual solvent after drying.

[0214] <Method for producing color conversion composition>

[0215] An example of a method for producing a color conversion composition according to an embodiment of the present invention is described below. In this production method, the above-mentioned components (A) to (C), optional additives, solvents, etc. are mixed in a manner to form a prescribed composition, and then uniformly mixed or kneaded using a stirring / kneading machine to obtain a color conversion composition. Examples of stirring / kneading machines include homogenizers, rotation-revolutionary mixers, three-roll mills, ball mills, planetary ball mills, bead mills, and the like. After mixing or dispersing, or during mixing or dispersing, it is also preferred to degas under vacuum or reduced pressure conditions. In addition, certain specific components may be pre-mixed and subjected to treatments such as aging. The solvent may also be removed using an evaporator to achieve the desired solid content concentration.

[0216] <Color conversion sheet>

[0217] The color conversion sheet according to an embodiment of the present invention (hereinafter, sometimes referred to as the color conversion sheet of the present invention) preferably includes a color conversion layer as a layer formed from the above-mentioned color conversion composition or a cured product thereof. The cured product of the color conversion composition is preferably included in the color conversion sheet as a layer obtained by curing the color conversion composition (a layer formed from a cured product of the color conversion composition). As representative structural examples of the color conversion sheet of the present invention, for example, the following four can be cited.

[0218] Figure 1 Schematic cross-sectional view showing a first example of a color conversion sheet according to an embodiment of the present invention. Figure 1 As shown, the color conversion sheet 1A of the first example is a single-layer sheet composed of a color conversion layer 11. The color conversion layer 11 is a layer formed from the color conversion composition of the present invention or a cured product thereof.

[0219] Figure 2 2 is a schematic cross-sectional view showing a second example of a color conversion sheet according to an embodiment of the present invention. Figure 2 As shown in FIG. 1 , the color conversion sheet 1B of the second example is a laminate of a base material layer 10 and a color conversion layer 11. In the structural example of the color conversion sheet 1B, the color conversion layer 11 is laminated on the base material layer 10.

[0220] Figure 3 2 is a schematic cross-sectional view showing a third example of a color conversion sheet according to an embodiment of the present invention. Figure 3 As shown in FIG. 1 , the color conversion sheet 1C of the third example is a laminate of a plurality of base layers 10 and a color conversion layer 11. In the structural example of the color conversion sheet 1C, the color conversion layer 11 is sandwiched between the plurality of base layers 10.

[0221] Figure 4 2 is a schematic cross-sectional view showing a fourth example of a color conversion sheet according to an embodiment of the present invention. Figure 4 As shown in FIG. 1 , the color conversion sheet 1D of the fourth example is a laminate of a plurality of substrate layers 10, a color conversion layer 11, and a plurality of barrier films 12. In the structural example of the color conversion sheet 1D, the color conversion layer 11 is sandwiched by a plurality of barrier films 12, and further, the laminate of the color conversion layer 11 and the plurality of barrier films 12 is sandwiched by a plurality of substrate layers 10. That is, in order to prevent the color conversion layer 11 from being deteriorated by oxygen, moisture, and heat, as shown in FIG. Figure 4 As shown, the color conversion sheet 1D may have a barrier film 12 .

[0222] The thickness of the color conversion sheet involved in the embodiment of the present invention is preferably 30 μm or more and 300 μm or less. Here, the thickness of the color conversion sheet refers to the total thickness of all layers included in the color conversion sheet, which is the film thickness (average film thickness) obtained by measuring the thickness by mechanical scanning method A in JIS K7130 (1999) Plastics-Film and Sheet-Thickness Measurement Method. By making the thickness of the color conversion sheet of the present invention greater than 30 μm, the toughness of the color conversion sheet can be improved. In addition, by making the thickness of the color conversion sheet of the present invention less than 300 μm, cracks in the color conversion sheet can be suppressed.

[0223] (Base material layer)

[0224] As the base material layer (for example Figures 2 to 4The substrate layer 10 shown in the figure may be, for example, glass, resin film, etc. As the resin film, preferably, a film of plastic such as polyethylene terephthalate (PET), polyphenylene sulfide, polycarbonate, polypropylene, polyimide, etc. From the perspective of the ease of film peeling, the surface of the substrate film may be subjected to a demolding treatment in advance. The thickness of the substrate layer is not particularly limited, but as a lower limit, it is preferably 25 μm or more, and more preferably 38 μm or more. In addition, as an upper limit, it is preferably 5000 μm or less, and more preferably 3000 μm or less.

[0225] (Barrier Film)

[0226] The barrier film (e.g. Figure 4 The barrier film 12 shown in the figure can be used appropriately in the case of improving the gas barrier property of the color conversion layer. As the barrier film (also referred to as the barrier layer), it is preferable to use a film that inhibits the intrusion of oxygen, moisture, heat, etc. into the color conversion layer. The color conversion sheet of the present invention may have two or more layers of such barrier films. For example, the color conversion sheet of the present invention may be as follows: Figure 4 Although barrier films are provided on both sides of the color conversion layer like the barrier film 12 shown as an example, a barrier film may be provided on only one side of the color conversion layer.

[0227] As barrier films with gas barrier properties, for example, 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 films formed by adding other elements to them, metal nitride films, or films containing various resins such as polyvinylidene chloride, acrylic resin, silicone resin, melamine resin, urethane resin, fluorine resin, and polyvinyl alcohol resins such as saponified products of vinyl acetate. The barrier film may contain two or more of these. In addition, as barrier films with a barrier function for moisture, for example, films containing various resins such as polyethylene, polypropylene, nylon, polyvinylidene chloride, copolymers of vinyl chloride and vinyl chloride, copolymers of vinyl chloride and acrylonitrile, fluorine resins, and polyvinyl alcohol resins such as saponified products of vinyl acetate can be cited.

[0228] The color conversion sheet of the present invention can further have: a light diffusion layer, an adhesive layer, an auxiliary layer with anti-reflection function, anti-glare function, anti-reflection and anti-glare function, a hard coating function (friction resistance function), an anti-static function, an anti-fouling function, an electromagnetic wave shielding function, an infrared cutting function, an ultraviolet cutting function, a polarizing function, a color adjustment function, etc. according to the required functions.

[0229] (Other films)

[0230] The color conversion sheet according to the embodiment of the present invention may further include a polarizing reflective film, a diffuser, a prism sheet, a wavelength selective reflective film, etc. Suitable specific examples of wavelength selective reflective films include films described in International Publication No. 2017 / 164155 and Japanese Patent Application Publication No. 2018-81250.

[0231] <Method for Manufacturing Color Conversion Sheet>

[0232] Next, an example of a method for manufacturing a color conversion sheet according to an embodiment of the present invention is described. In the method for manufacturing the color conversion sheet, the color conversion composition prepared by the above method is applied to a substrate layer, a barrier layer, or the like, and dried. Thus, a color conversion layer is formed. When the binder resin contained in the color conversion composition is a thermosetting resin, the color conversion layer can be formed by heat curing after the color conversion composition is applied to a substrate layer or the like. When the binder resin contained in the color conversion composition is a photocurable resin, the color conversion layer can be formed by light curing after the color conversion composition is applied to a substrate layer or the like.

[0233] The color conversion composition can be applied by a reverse roll coater, a knife coater, a comma coater, a slot die coater, a direct gravure coater, an offset gravure coater, a kiss coater, a natural roll coater, an air knife coater, a roll knife coater, a two stream coater, a rod coater, a wire bar coater, an applicator, a dip coater, a curtain coater, a spin coater, a knife coater, etc. In order to obtain uniform film thickness of the color conversion layer, it is preferably applied by a slot die coater, a comma coater, or a dip coater.

[0234] The color conversion layer can be dried using a common 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. Alternatively, the color conversion layer can be cured by heat in stages by a method such as step curing.

[0235] When the color conversion layer is formed by heat curing, a heating device may be a hot air oven or the like. The heating conditions for heat curing the color conversion layer may 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.

[0236] When the color conversion layer is formed by photocuring, it is preferred that the color conversion layer be irradiated with high energy light such as ultraviolet rays. The light irradiation conditions for the photocuring of the color conversion layer can be selected according to the binder resin. For example, the wavelength of the irradiated light is preferably 200nm to 500nm, and the irradiation amount of the light is preferably 10mJ / cm 2~10J / cm 2 .

[0237] After the color conversion layer is formed, the base material layer may be changed as needed. In this case, simple methods include, for example, a method of pasting and replacing using a hot plate, a method of using a vacuum laminator, or a dry film laminator.

[0238] <Light source unit>

[0239] The light source unit involved in the embodiment of the present invention (hereinafter, sometimes referred to as the light source unit of the present invention) comprises at least a light source and the above-mentioned color conversion composition or color conversion sheet. The light source provided in the light source unit of the present invention is a source for generating the above-mentioned excitation light. There is no particular limitation on the configuration method of these light sources and the color conversion sheet. The light source and the color conversion sheet may be closely fitted or remote phosphors may be separated from the color conversion sheet. In addition, in order to improve color purity, the light source unit of the present invention may be further provided with a color filter.

[0240] (light source)

[0241] The type of light source that the light source unit of the present invention has can use any light source as long as it shows light emission in the wavelength region that the compound (organic light-emitting material) that emits delayed fluorescence can absorb. For example, fluorescent light sources such as hot cathode tubes, cold cathode tubes, inorganic electroluminescence (EL), organic EL element light sources, LED light sources, incandescent light sources, or any light source of excitation light such as sunlight can be used in principle. Among these, LED light sources are suitable light sources. For example, light-emitting diodes that have a maximum light emission in the range of wavelengths of more than 400nm and less than 500nm are more preferred LED light sources. In display devices and lighting applications, from the aspect of improving the color purity of blue light, a blue LED light source that has a maximum light emission in the range of wavelengths of more than 400nm and less than 500nm is a more suitable light source.

[0242] The light source may have one luminescence peak or two or more luminescence peaks, but preferably has one luminescence peak in order to improve color purity. In addition, a plurality of light sources having different luminescence peaks may be used in any combination.

[0243] The light source unit of the present invention is useful for various light sources such as space lighting and backlighting. Specifically, the light source unit of the present invention can be used for display devices, lighting devices, interior decoration, signs, billboards, etc., and is particularly suitable for display devices and lighting devices.

[0244] <Display device, lighting device>

[0245] A display device according to an embodiment of the present invention includes at least the above-mentioned light source unit. For example, in a display device such as a liquid crystal display, a light source unit including the above-mentioned light source and a color conversion sheet can be used as a backlight unit. In addition, a lighting device according to an embodiment of the present invention includes at least the above-mentioned light source unit. For example, the lighting device is configured as follows: a blue LED light source as a light source unit is combined with a color conversion sheet that converts blue light from the blue LED light source into light with a longer wavelength to emit white light.

[0246] Example

[0247] Hereinafter, the present invention will be described with reference to Examples, but the present invention is not limited to the following Examples. First, the evaluation methods in Examples and Comparative Examples will be described.

[0248] <Light durability evaluation>

[0249] In the evaluation of light durability, a light-emitting device equipped with a color conversion sheet and a blue LED element (manufactured by USHIOEPITEX; model SMBB450H-1100, peak wavelength of light emission: 450nm) as the evaluation object was used. The color conversion sheet as the evaluation object was prepared in the examples and comparative examples, respectively, and was changed and arranged in the light-emitting device according to each example and each comparative example. A current of 30mA was passed through the light-emitting device to light up the blue LED element, and the luminous intensity at the peak wavelength of the initial color-converted light was measured using a spectroradiometer (CS-1000, manufactured by Konica Minolta). It should be noted that the distance between the color conversion sheet and the blue LED element in the light-emitting device was 3cm. Then, after continuous irradiation with light from the blue LED element in an environment of 50°C, the time until the peak intensity of the light from the color conversion sheet decreased by a certain amount was observed, thereby evaluating the light durability of the color conversion sheet.

[0250] <Moisture resistance evaluation>

[0251] In the moisture resistance evaluation, the color conversion sheets prepared in the examples and comparative examples were cut into 8 mm squares to prepare samples, and the prepared samples were excited with excitation light of a wavelength of 450 nm using the absolute fluorescence quantum yield measuring device Quantaurus-QY manufactured by Hamamatsu Photonics to measure the initial fluorescence quantum yield. Next, the color conversion sheets prepared in the examples and comparative examples were cut into 10 cm squares to prepare samples, and the prepared samples were stored in an environment of 85°C and 85% RH for 800 hours, and then the fluorescence quantum yield was measured in the same manner as above. The moisture resistance of the color conversion sheet was evaluated by calculating the difference between the initial fluorescence quantum yield obtained in this way and the fluorescence quantum yield after storage for 800 hours (fluorescence quantum yield difference). In the results of the moisture resistance evaluation, the smaller the fluorescence quantum yield difference, the better the moisture resistance.

[0252] The materials used in the following examples and comparative examples are as follows. Compounds G-1, G-2 and compound R-1 are examples of component (A) (luminescent material). Compounds Q-1 to Q-6 are examples of component (C) (compounds represented by general formula (1)). Compounds X-1 to X-3 are examples of metal complexes other than component (C).

[0253] [Chemical formula 23]

[0254]

[0255] [Chemical formula 24]

[0256]

[0257] (Example 1)

[0258] In Example 1, 0.40 parts by weight of the compound G-1 as the component (A), 0.003 parts by weight (0.0287 equivalents to the compound G-1) as the component (C), and 300 parts by weight of ethyl acetate as the solvent were mixed with respect to 100 parts by weight of the binder resin (BR-85) as the component (B). Then, the mixture was stirred and degassed at 1000 rpm for 20 minutes using a planetary stirring and degassing device "MAZERUSTAR" (registered trademark) KK-400 (manufactured by Kurabo Co., Ltd.), thereby obtaining a green color conversion composition as a resin solution for preparing a green color conversion layer.

[0259] Next, "Vylon" 630 as a binder resin of component (B) was used, and 300 parts by weight of ethyl acetate as a solvent was mixed with 100 parts by weight of the component (B). Then, the mixture was stirred and degassed at 300 rpm for 20 minutes using a planetary stirring and degassing device "MAZERUSTAR" (registered trademark) KK-400 (manufactured by Kurabo Co., Ltd.), thereby obtaining a resin composition for an adhesive layer.

[0260] Next, the green color conversion composition was applied onto a polyester film "Lumirror" (registered trademark) U48 (manufactured by Toray Industries, Ltd., thickness 50 μm) using a slot die coater and dried by heating at 120° C. for 20 minutes to form a green color conversion layer having an average film thickness of 20 μm.

[0261] Similarly, the red color conversion composition was applied to the PET substrate layer side of the light diffusion film "Chemicalmatte" 125PW (manufactured by Kimoto Co., Ltd., thickness 138 μm) using a slot die coater and dried by heating at 120° C. for 20 minutes. Thus, a red color conversion layer with an average film thickness of 20 μm was formed.

[0262] Furthermore, the above-mentioned adhesive layer resin composition was applied onto the above-mentioned red color conversion layer formed on the PET base layer side of the light diffusion film "Chemical Matte" 125PW (manufactured by Kimoto Co., Ltd., thickness 138 μm) using a slot die coater, and heated and dried at 120° C. for 20 minutes. Thus, an adhesive layer with an average film thickness of 10 μm was formed on the red color conversion layer.

[0263] Then, the green color conversion layer and the red color conversion layer were bonded via the adhesive layer to produce a color conversion sheet. The color conversion sheet produced in this way was used to convert the color of blue light. As a result, when only the luminous area of ​​green light was cut, green luminescence with a peak wavelength of 529nm and a half-value width of the luminous spectrum at the peak wavelength of 27nm was obtained. In addition, the light durability evaluation and moisture resistance evaluation of the color conversion sheet were performed by the above method. The components contained in Example 1 and the evaluation results are shown in Table 1 described below.

[0264] (Examples 2 to 10, Comparative Examples 1 to 6)

[0265] In Examples 2 to 10, the types of the components (A) and (C) used were set as shown in Table 1, and the amount of the component (C) added was changed to 0.0287 of the amount of the component (A). The color conversion sheet was prepared by the same method as in Example 1. It should be noted that in Comparative Examples 1 to 3, compounds X-1 to X-3, which are other metal complexes, were added instead of the component (C). In Comparative Examples 4 to 6, the component (C) was not added. For these Examples 2 to 10 and Comparative Examples 1 to 6, the light durability and moisture resistance of the color conversion sheets prepared were evaluated. The components contained in Examples 2 to 10 and Comparative Examples 1 to 6 and the evaluation results are shown in Table 1.

[0266] [Table 1]

[0267]

[0268] Comparison between Examples 1 to 10 and Comparative Examples 4 to 6 revealed that the light durability of each of Examples 1 to 10 was improved compared to Comparative Examples 4 to 6 in which neither the component (C) nor other metal complexes were added.

[0269] In addition, by comparing Examples 1 to 10 with Comparative Examples 1 to 3, it can be seen that the moisture resistance of Examples 1 to 10 is greatly improved compared to Comparative Examples 1 to 3 in which other metal complexes are added instead of component (C). According to this result, the copper complex having a ligand with an electron-withdrawing group exhibits good moisture resistance. According to the comparison results of Example 1 and Comparative Example 2, in the complex having a ligand with an electron-withdrawing group, the bond between copper as an intermediate acid and the ligand is stronger than that between scandium as a hard acid, which is the central metal.

[0270] In addition, according to the comparison results of Examples 1, 3 to 6 with Example 2, it can be seen that compared with Example 2 in which the electron withdrawing group of the (C) component does not contain a fluorine atom, the moisture resistance of Examples 1, 3 to 6 using a ligand having an electron withdrawing group containing a fluorine atom in the (C) component is further improved.

[0271] In addition, referring to Table 1, it can be seen that compared with Example 3 and Example 5 in which the (C) component does not contain an electron-withdrawing group with 4 or more fluorine atoms, the initial fluorescence quantum yield in Example 1, Example 4 and Examples 6 to 10 using a ligand having an electron-withdrawing group with 4 or more fluorine atoms in the (C) component shows a good value, and the light durability is also improved to more than 500 hours.

[0272] In addition, by comparing Examples 1 and 6 with Example 4, it can be seen that the moisture resistance of Examples 1 and 6 using a ligand having a perfluoroalkyl group with a carbon number of 2 or more as an electron-withdrawing group in the component (C) is further improved compared to Example 4 which does not have the above-mentioned perfluoroalkyl group as the electron-withdrawing group in the component (C).

[0273] In addition, when comparing Examples 1, 3 to 6 with Example 2, it can be seen that compared with Example 2, the R b The light durability in Examples 1 and 3 to 6 in which the ligand was a hydrogen atom was further improved.

[0274] In addition, by comparing Example 3 with Example 5, it can be seen that compared with Example 5, the X in the general formula (1) used in the component (C) is 1 and X 2 The initial fluorescence quantum yield in Example 3, in which all ligands are O, shows a better value.

[0275] Furthermore, from the comparison results between Examples 1 and 6 and Examples 7 and 8, it can be seen that when the light-emitting material as the component (A) has an electron-withdrawing group, the decrease in the initial fluorescence quantum yield can be suppressed.

[0276] Industrial Applicability

[0277] As described above, the color conversion composition, color conversion sheet, light source unit, display device, and lighting device according to the present invention are useful in improving light durability and moisture resistance, and are particularly suitable for a color conversion composition, color conversion sheet, light source unit, display device, and lighting device having excellent light durability and moisture resistance.

[0278] Reference numerals

[0279] 1A, 1B, 1C, 1D Color conversion sheets

[0280] 10. Base material layer

[0281] 11 Color conversion layers

[0282] 12 Barrier film

Claims

1. A color conversion composition, characterized in that Containing the following components (A), (B) and (C), (A) Ingredients: luminescent material; (B) component: binder resin; Component (C): a compound represented by the following general formula (1), [Chemical formula 1] In the general formula (1), X 1 and X 2 Each independently is O or S; R a ~R c each independently selected from a hydrogen atom, an alkyl group, a cycloalkyl group, a heterocyclic group, an alkenyl group, a cycloalkenyl group, an alkynyl group, a hydroxyl group, an alkoxy group, a thiol group, an alkylthio group, an aryl ether group, an aryl thioether group, an aryl group, a heteroaryl group, a halogen group, a cyano group, an aldehyde group, an oxycarbonyl group, a carbamoyl group, an amino group, a nitro group, a silyl group, a siloxane group, a boron group, a phosphine oxide group, -C(=O)R 101 、-S(=O)R 102 R 103 、-S(=O)R 104 、-S(=O)2R 105 and a group consisting of a condensed ring or an aliphatic ring formed with adjacent substituents; R 101 ~R 105 is a substituent, R 102 With R 103 can be fused together to form a ring; wherein R a ~R c At least one of them is an electron withdrawing group; n is an integer of 1-4.

2. The color conversion composition according to claim 1, characterized in that The electron withdrawing group is a group containing a fluorine atom.

3. The color conversion composition according to claim 1, characterized in that The electron withdrawing group is a group having 4 or more fluorine atoms.

4. The color conversion composition according to claim 1, characterized in that The electron withdrawing group is a perfluoroalkyl group having 2 or more carbon atoms.

5. The color conversion composition according to claim 1, characterized in that In the general formula (1), R b A hydrogen atom.

6. The color conversion composition according to claim 1, characterized in that X in the general formula (1) 1 and X 2 All are O.

7. The color conversion composition according to claim 1, characterized in that The component (A) contains a compound represented by the following general formula (2): [Chemical formula 2] In the general formula (2), X is CR 7 or N; R 1 ~R 9 The substituents may be the same as or different from each other 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, a halogen, a cyano group, an aldehyde group, a carbonyl group, a carboxyl group, an oxycarbonyl group, a carbamoyl group, an amino group, a nitro group, a silyl group, a siloxane group, a boron group, a phosphine oxide group, and a condensed ring or an aliphatic ring formed with an adjacent substituent.

8. The color conversion composition according to claim 7, characterized in that In the general formula (2), R 1 ~R 6 At least one of is an electron withdrawing group, X in the general formula (2) is CR 7 , The R 7 is a group represented by the following general formula (3), [Chemical formula 3] In the general formula (3), r is 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, a halogen group, a cyano group, an aldehyde group, a carbonyl group, a carboxyl group, an oxycarbonyl group, a carbamoyl group, an amino group, a nitro group, a silyl group, a siloxane group, a boron group, and a phosphine oxide group; k is an integer from 1 to 3; when k is 2 or more, r may be the same as or different from each other.

9. The color conversion composition according to claim 1, characterized in that The component (A) contains at least one of the following luminescent materials (a) and (b), Luminescent material (a): a luminescent material that emits light having a peak wavelength observed in a region of 500 nm to less than 580 nm by using excitation light having a wavelength in the range of 400 nm to 500 nm; Luminescent material (b): A luminescent material that is excited by at least one of excitation light having a wavelength in the range of 400 nm to 500 nm and luminescence from the luminescent material (a), thereby exhibiting luminescence with a peak wavelength observed in the region of 580 nm to 750 nm.

10. The color conversion composition according to claim 1, characterized in that The component (B) is a thermoplastic resin.

11. A color conversion sheet, characterized in that: The invention comprises the color conversion composition according to any one of claims 1 to 10 or a cured product thereof.

12. A light source unit, characterized in that It has: a light source; and The color conversion composition according to any one of claims 1 to 10.

13. The light source unit according to claim 12, characterized in that: The light source is a light emitting diode having a maximum light emission within a wavelength range of 400 nm to 500 nm.

14. A display device, characterized in that A light source unit according to claim 12 is provided.

15. A lighting device, characterized in that A light source unit according to claim 12 is provided.

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