TW202022084A - Color conversion composition, color conversion layer, wavelength conversion substrate, wavelength conversion substrate manufacturing method, and display - Google Patents

Abstract

Provided is a color conversion composition that achieves both preferably high color reproducibility and preferably high durability in a color conversion material for use in a micro LED display or an organic EL display. A color conversion composition according to the present invention is characterized by containing a pyrromethene derivative, a matrix resin, and inorganic particles having a refractive index of 1.7-2.8 and by not containing a photosensitive component.

Description

Color conversion composition, color conversion layer, wavelength conversion substrate, manufacturing method of wavelength conversion substrate, and display

The present invention relates to a color conversion composition containing a pyrromethene derivative and fine particles, a color conversion layer, a wavelength conversion substrate, a method for manufacturing a wavelength conversion substrate, and a display.

The application of multicolor technology of color conversion methods to liquid crystal displays, organic electroluminescence (EL) displays, lighting, etc. is being actively studied. As a problem of liquid crystal displays, improvement of color reproducibility can be cited. In order to improve color reproducibility, it is effective to increase the color purity of blue, green, and red by narrowing the full width at half maximum of each emission spectrum of blue, green, and red of the light source unit. . As a means to solve this problem, a technology using quantum dots of inorganic semiconductor fine particles as a component of a color conversion composition has been proposed. In addition, there has also been proposed a technology that uses organic light-emitting materials instead of quantum dots as components of the color conversion composition. As an example of a technique using an organic light-emitting material as a component of a color conversion composition, a pyrromethene derivative is disclosed (for example, refer to Patent Document 1). Furthermore, the problems of liquid crystal displays include slow response speed or low contrast. In order to compensate for these problems, organic EL displays or miniature light emitting diode (LED) displays use self-luminous light sources like self-luminous displays. Having attention. For example, as one of the methods for realizing multicolor light emission using a self-luminous light source, a color conversion (CCM) method has been proposed (for example, refer to Patent Document 2 and Patent Document 3). The method can use organic EL elements that emit monochromatic light, so the display is easy to manufacture, and the development of large-screen displays is also actively studied. [Prior Art Literature] [Patent Literature]

Patent Document 1: Japanese Patent Laid-Open No. 2011-241160 Patent Document 2: Japanese Patent Laid-Open No. 8-286033 Patent Document 3: International Publication No. 2010/092694

[Problems to be solved by the invention] However, a light-emitting element using the organic light-emitting material described in Patent Document 1 is still insufficient from the viewpoint of color reproducibility and durability. In particular, the technology that can achieve both color reproducibility and high durability is insufficient. Patent Document 2 and Patent Document 3 disclose the CCM method using fluorescent pigments as the luminescent material, but the excitation light spectrum and the emission spectrum of the fluorescent material have not narrow half-height widths, and the improvement in color purity is insufficient. In addition, there is a problem that the light-emitting material has low stability to light, and the chromaticity changes significantly during continuous lighting.

Therefore, the problem to be solved by the present invention is to provide a color conversion composition having both high color reproducibility and high durability in color conversion materials used in micro LED displays or organic EL displays. [Means to solve the problem]

The inventors of the present invention conducted diligent studies and found that the problem can be solved by a color conversion composition containing inorganic particles having a specific refractive index and not containing a photosensitive component. That is, the present invention has the following configuration. A color conversion composition characterized by containing a pyrromethene derivative, a matrix resin, and inorganic particles with a refractive index of 1.7 to 2.8, and containing no photosensitive component. [Effect of invention]

According to the present invention, a color conversion composition having high color reproducibility and excellent durability can be provided.

＜Color conversion composition＞ In the present invention, the color conversion composition refers to a color conversion composition that contains a pyrromethene derivative, a matrix resin, and inorganic particles, and does not contain photosensitive components such as a photopolymerizable compound or a photopolymerizable initiator. When the color conversion composition contains photosensitive components such as photopolymerizable compounds or photopolymerizable initiators, free radicals are generated during photoreaction, causing degradation of pyrromethene derivatives, resulting in color conversion efficiency and durability reduce. In addition, even with time, free radicals are generated, causing degradation of the pyrromethene derivative. As a result, the durability of the color conversion composition decreases. In addition, the color conversion composition of the present invention preferably does not contain a heat sensitive component. The thermosensitive component specifically refers to a thermally polymerizable initiator. When the color conversion composition of the present invention does not contain a thermosensitive component, it is possible to suppress the generation of free radicals caused by the thermal reaction. As a result, color conversion efficiency and durability are improved, which is preferable.

＜Inorganic particles＞ The refractive index of the inorganic particles used in the present invention is 1.7 to 2.8. If the refractive index is less than 1.7, the scattering effect for incident light and luminescence derived from the pyrromethene derivative is low, and therefore the optical path length cannot be increased. Therefore, the effect of improving the color conversion efficiency of the pyrromethene derivative is insufficient. In terms of increasing the optical path length due to the increased scattering effect and improving the color conversion efficiency, the refractive index of the inorganic particles is preferably 1.7 or more, more preferably 1.75 or more, and even more preferably 2.0 or more.

On the other hand, if the refractive index of the inorganic particles exceeds 2.8, the scattering effect becomes high, but the difference in refractive index between the color conversion composition and the air interface or glass interface increases, making it difficult to extract the color-converted light. As a result, the brightness decreases, so the refractive index of the inorganic particles is preferably 2.8 or less, more preferably 2.72 or less, and still more preferably 2.5 or less. Here, the refractive index of inorganic particles in the present invention refers to 30 randomly selected inorganic particles, using sodium D rays (589 nm) as a light source, and using an Abbe refractometer at a temperature of 25°C (Manufactured by DR-M2, Atago (stock)), the numerical average of the refractive index measured by the liquid immersion method (Baker's wire method). The shape of the inorganic particles is not particularly limited, and examples thereof include a spherical shape, an ellipsoidal shape, a needle shape, a polygonal shape, and a star shape. The surface may have irregularities or pores, or may be hollow.

(Particle size) From the viewpoint of obtaining a sufficient light scattering effect, the average particle diameter of the inorganic particles in the present invention is preferably 0.1 μm or more. In addition, from the viewpoint of obtaining sufficient color conversion efficiency, it is preferably 0.7 μm or less. From the viewpoint of color conversion efficiency, it is preferably 0.2 μm or more, more preferably 0.6 μm or less, and more preferably 0.5 μm or less. In the present invention, the average particle diameter of the inorganic particles means the median particle diameter (D50). According to the two-dimensional image obtained by observing inorganic particles with a scanning electron microscope (Scanning Electron Microscope, SEM), calculate the maximum distance between the two intersections of the straight lines that intersect the outer edge of the particle at two points, and the maximum The distance is defined as the individual particle size. The particle size was calculated for 200 observed particles, and in the particle size distribution thus obtained, the particle size at which the cumulative pass rate from the small particle size side was 50% was taken as D50. For example, in the case of measuring the particle size of the inorganic particles present in the cured film of the color conversion composition, the mechanical polishing method, the microtome method, the cross section polisher (CP) method, and the focused ion beam (Focused Ion Beam) can be used. Ion Beam, FIB) processing method, after polishing so that the cross-section of the cured film is observed, the average particle size is calculated from the two-dimensional image obtained by observing the cross-section with a scanning electron microscope (SEM) .

(species) Examples of inorganic particles include titanium dioxide, zirconium oxide, aluminum oxide, cerium oxide, tin oxide, indium oxide, iron oxide, zinc oxide, aluminum nitride, aluminum, tin, titanium or zirconium sulfide, and titanium or zirconium hydroxide. These may be used alone, or two or more of them may be used in combination. From the viewpoint of high refractive index and ease of acquisition, aluminum oxide, tin oxide, titanium dioxide, zirconium oxide, sulfides of titanium or zirconium, hydroxides of titanium or zirconium, etc. can be cited as preferred inorganic particles. Among these, it is more preferable to use at least one selected from the group consisting of aluminum oxide, zirconium oxide, and titanium dioxide in terms of refractive index adjustment of the coating film and the cured film, and particularly titanium dioxide is preferably used. As commercially available inorganic particles, alumina particles include "AKP-50", "AKP-3000" (the above are made by Sumitomo Chemical Co., Ltd.), and "Admafine A0-5" (Adu (Manufactured by Admatechs (stock) company), "AEROXIDE" Alu C (manufactured by Japan Aeroxide (stock) company), etc. Examples of zirconia particles include "UEP-100" (manufactured by Daiichi Rare Element Chemical Industry Co., Ltd.) and the like. Examples of the titanium dioxide particles include "JR-301" and "JR-805" (the above are manufactured by Tayca Co., Ltd.).

(content) In the color conversion composition of the present invention, the content of inorganic particles is preferably 3% by mass or more and 70% by mass or less. In terms of uniformly dispersing in the color conversion composition and obtaining a sufficient optical path length and improving the color conversion efficiency, the content of inorganic particles is preferably 3% by mass or more, more preferably 4% by mass or more, and still more preferably 5 Above mass%. On the other hand, in terms of improving color conversion efficiency without agglomeration or sedimentation of inorganic particles in the color conversion composition, the content of inorganic particles is preferably 70% by mass or less, more preferably 20% by mass or less, and still more preferably 15 Less than mass%. In addition, regarding the content of inorganic particles, from the viewpoint of the quantum yield of the pyrromethene group, the mass ratio of the content of the inorganic particles to the content of the pyrromethene derivative (pyrromethene derivative/inorganic particles) Preferably it is 0.01-3.33, More preferably, it is 0.15-0.8.

In the color conversion composition of the present invention, when the inorganic particles are titanium dioxide, the content of titanium dioxide is preferably 3% by mass or more and 20% by mass or less. If it is 3% by mass or more, it is uniformly dispersed in the color conversion composition, a sufficient optical path length is obtained, and the color conversion efficiency is improved, which is preferable. Preferably it is 4 mass% or more. On the other hand, if it is 20% by mass or less, it is difficult for the inorganic particles to aggregate or settle in the color conversion composition, and the color conversion efficiency is improved, which is preferable. Preferably it is 15 mass% or less. In addition, regarding the content of titanium dioxide, from the viewpoint of the quantum yield of pyrromethene, the mass ratio of the content of titanium dioxide to the content of pyrromethene derivative (pyrromethene derivative/titanium dioxide) is preferably 0.02-2.5, more preferably 0.027-1.5. If it is within the above range, the quantum yield of the pyrromethene derivative will not be reduced, but the optical path length will be increased, and therefore a very high color conversion efficiency can be obtained.

X為C-R⁷ 或N。R¹ ～R⁹ 分別可相同亦可不同，且選自氫、烷基、環烷基、雜環基、烯基、環烯基、炔基、羥基、硫醇基、烷氧基、烷硫基、芳基醚基、芳基硫醚基、芳基、雜芳基、鹵素、氰基、醛基、羰基、羧基、酯基、胺甲醯基、胺基、硝基、矽烷基、矽氧烷基、氧硼基、磺基、氧化膦基中，所述選擇的基與鄰接取代基之間亦可形成縮合環及脂肪族環。<Pyrromethene derivative> The color conversion composition of the present invention contains a pyrromethene derivative. The pyrromethene derivative is preferably a compound represented by the general formula (1). [Chem 1]

X is CR ⁷ or N. R ¹ to R ⁹ may be the same or different, and are selected from hydrogen, alkyl, cycloalkyl, heterocyclyl, alkenyl, cycloalkenyl, alkynyl, hydroxyl, thiol, alkoxy, and alkylthio Group, aryl ether group, aryl sulfide group, aryl group, heteroaryl group, halogen, cyano group, aldehyde group, carbonyl group, carboxyl group, ester group, aminomethanyl group, amine group, nitro group, silyl group, silicon In the oxyalkyl group, oxyboron group, sulfo group, and phosphine oxide group, the selected group and the adjacent substituent may also form a condensed ring and an aliphatic ring.

In all the groups, hydrogen may be deuterium. This is the same in the compounds described below or partial structures thereof. In addition, in the following description, for example, a substituted or unsubstituted aryl group having 6 to 40 carbons means that all the carbons including the number of carbons contained in the substituents substituted in the aryl group are 6 to 40 aryl groups. The same applies to other substituents whose carbon number is specified.

In addition, among all the above groups, the substituents in the case of substitution are preferably alkyl groups, cycloalkyl groups, heterocyclic groups, alkenyl groups, cycloalkenyl groups, alkynyl groups, hydroxyl groups, thiol groups, and alkyl groups. Oxy, alkylthio, aryl ether, aryl sulfide, aryl, heteroaryl, halogen, cyano, aldehyde, carbonyl, carboxy, ester, carbamoyl, amine, nitro , Silyl group, siloxyalkyl group, oxyboron group, sulfo group, phosphine oxide group, and more preferably specific substituents deemed preferable in the description of each substituent. In addition, these substituents may be further substituted with the above-mentioned substituents.

"Unsubstituted" in the case of "substituted or unsubstituted" means that a hydrogen atom or a deuterium atom is substituted. In the compounds described below or partial structures thereof, the case of "substituted or unsubstituted" is also the same as described above.

Among all the groups mentioned above, the so-called alkyl group means, for example, saturated aliphatic hydrocarbon groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, second butyl, tertiary butyl, etc., which may have The substituent may not have a substituent. In addition, the carbon number of the alkyl group is not particularly limited, but in terms of ease of acquisition and cost, it is preferably in the range of 1 or more and 20 or less, and more preferably in the range of 1 or more and 8 or less.

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

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

The alkenyl group means, for example, an unsaturated aliphatic hydrocarbon group containing a double bond, such as a vinyl group, an allyl group, and a butadienyl group, which may or may not have a substituent. The carbon number of the alkenyl group is not particularly limited, but is preferably in the range of 2 or more and 20 or less.

The cycloalkenyl group means, for example, a double bond-containing unsaturated alicyclic hydrocarbon group such as a cyclopentenyl group, a cyclopentadienyl group, and a cyclohexenyl group, which may or may not have a substituent.

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

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

The so-called alkylthio group is one in which the oxygen atom of the ether bond of the alkoxy group is substituted with a sulfur atom. The hydrocarbon group of the alkylthio group may have a substituent, and may not have a substituent. The carbon number of the alkylthio group is not particularly limited, but is preferably in the range of 1 or more and 20 or less.

The aryl ether group means, for example, a functional group such as a phenoxy group to which an aromatic hydrocarbon group is bonded with an intermediary ether bond. The aromatic hydrocarbon group may or may not have a substituent. The carbon number of the aryl ether group is not particularly limited, but is preferably in the range of 6 or more and 40 or less.

The aryl sulfide group is one 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 sulfide group may or may not have a substituent. The carbon number of the aryl sulfide group is not particularly limited, but is preferably in the range of 6 or more and 40 or less.

基、芘基、丙[二]烯合芴基（fluoranthenyl group）、三亞苯基（triphenylenyl group）、苯並丙[二]烯合芴基、二苯並蒽基、苝基、螺旋烴基（helicenyl group）等芳香族烴基。其中，較佳為苯基、聯苯基、三聯苯基、萘基、芴基、菲基、蒽基、芘基、丙[二]烯合芴基、三亞苯基。芳基可具有取代基，亦可不具有取代基。芳基的碳數並無特別限定，較佳為6以上且40以下，更佳為6以上且30以下的範圍。The aryl group means, for example, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, triphenanthryl, benzoanthryl,

Group, pyrenyl, fluoranthenyl group, triphenylenyl group, benzoprop[di] fluorenyl group, dibenzoanthracenyl group, perylene group, helicenyl group group) and other aromatic hydrocarbon groups. Among them, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, pyrenyl, prop[di]ene fluorenyl, and triphenylene are preferred. The aryl group may or may not have a substituent. The carbon number of the aryl group is not particularly limited, but is preferably 6 or more and 40 or less, and more preferably in the range of 6 or more and 30 or less.

When R ¹ to R ⁹ are substituted or unsubstituted aryl groups, the aryl group is preferably phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, More preferred are phenyl, biphenyl, terphenyl and naphthyl. Phenyl, biphenyl and terphenyl are more preferred, and phenyl is particularly preferred.

When each substituent is further substituted with an aryl group, the aryl group is preferably phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, more preferably phenyl, biphenyl Phenyl, terphenyl, naphthyl. Particularly preferred is phenyl.

The so-called heteroaryl group means, for example, pyridyl, furyl, thienyl, quinolyl, isoquinolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, naphthyridinyl, cinnolinyl, phthalazine Group, quinoxolinyl, quinazolinyl, benzofuranyl, benzothienyl, indolyl, dibenzofuranyl, dibenzothienyl, carbazolyl, benzocarbazolyl, oxoline Group (carbolinyl group), indolocarbazolyl, benzofuranocarbazolyl, benzothiphenocarbazolyl, dihydroindenocarbazolyl, benzoquinolinyl, acridinyl, dibenzo Acridinyl, benzimidazolyl, imidazopyridyl, benzoxazolyl, benzothiazolyl, and phenanthroline are equal to one or more cyclic aromatic groups having atoms other than carbon in the ring. Among them, the so-called naphthyridinyl means 1,5-naphthyridinyl, 1,6-naphthyridinyl, 1,7-naphthyridinyl, 1,8-naphthyridinyl, 2,6-naphthyridinyl, 2, Any one of 7-naphthyridinyl. The heteroaryl group may or may not have a substituent. The carbon number of a heteroaryl group is not specifically limited, Preferably it is 2 or more and 40 or less, More preferably, it is the range of 2 or more and 30 or less.

When R ¹ to R ⁹ are substituted or unsubstituted heteroaryl groups, the heteroaryl group is preferably pyridyl, furyl, thienyl, quinolinyl, pyrimidinyl, triazinyl, and benzene. Furanyl, benzothienyl, indolyl, dibenzofuranyl, dibenzothienyl, carbazolyl, benzimidazolyl, imidazopyridyl, benzoxazolyl, benzothiazolyl, The phenanthryl group is more preferably pyridyl, furyl, thienyl, or quinolyl. Pyridyl is particularly preferred.

When each substituent is further substituted with a heteroaryl group, the heteroaryl group is preferably pyridyl, furyl, thienyl, quinolinyl, pyrimidinyl, triazinyl, benzofuranyl, benzothiophene Group, indolyl, dibenzofuranyl, dibenzothienyl, carbazolyl, benzimidazolyl, imidazopyridyl, benzoxazolyl, benzothiazolyl, phenanthryl, more preferably Pyridyl, furyl, thienyl, quinolinyl. Pyridyl is particularly preferred.

The term "halogen" means an atom selected from fluorine, chlorine, bromine and iodine.

The term "ester group" means, for example, an alkyl group, a cycloalkyl group, an aryl group, a heteroaryl group, etc., a functional group bonded via an ester bond, and the substituent may be further substituted. The carbon number of the ester group is not particularly limited, but is preferably in the range of 1 or more and 20 or less. More specifically, examples include methyl ester groups such as methoxycarbonyl, ethyl ester groups such as ethoxycarbonyl, propyl ester groups such as propoxycarbonyl, butyl ester groups such as butoxycarbonyl, isopropyl Isopropyl ester groups such as oxymethoxycarbonyl, hexyl ester groups such as hexyloxycarbonyl, phenyl ester groups such as phenoxycarbonyl, and the like. In addition, a carbonyl group, a carboxyl group, an ester group, and a urethane group may have a substituent or may not have a substituent.

The so-called amine group is a substituted or unsubstituted amine group. Examples of the substituent in the case of substitution include an aryl group, a heteroaryl group, a linear alkyl group, a branched alkyl group, and the like. The aryl group and heteroaryl group are preferably phenyl, naphthyl, pyridyl, and quinolinyl. These substituents may be further substituted. The carbon number is not particularly limited, but is preferably 2 or more and 50 or less, more preferably 6 or more and 40 or less, and particularly preferably 6 or more and 30 or less.

The silyl group means, for example, an alkylsilyl group such as a trimethylsilyl group, a triethylsilyl group, a tertiary butyldimethylsilyl group, a propyldimethylsilyl group, and a vinyldimethylsilyl group, or Arylsilyl groups such as phenyldimethylsilyl group, tertiary butyldiphenylsilyl group, triphenylsilyl group and trinaphthylsilyl group. Substituents on silicon can be further substituted. The carbon number of the silyl group is not particularly limited, but is preferably in the range of 1 or more and 30 or less.

The siloxane group means, for example, a silicon compound group with an ether bond interposed, such as a trimethylsiloxy group. Substituents on silicon can be further substituted. In addition, the term “oxyboron group” refers to a substituted or unsubstituted oxyboron group. As the substituent in the case of substitution, for example, an aryl group, a heteroaryl group, a linear alkyl group, a branched alkyl group, an aryl ether group, an alkoxy group, a hydroxyl group, etc. can be mentioned. Among them, aryl groups and aryl ether groups are preferred. In addition, the so-called sulfo group means a substituted or unsubstituted sulfo group. Examples of the substituent in the case of substitution include an aryl group, a heteroaryl group, a linear alkyl group, a branched alkyl group, an aryl ether group, and an alkoxy group. Among them, linear alkyl groups and aryl groups are preferred. In addition, the phosphine oxide group means a group represented by -P(=O)R ¹⁰ R ¹¹ . R ¹⁰ R ^{11 is} selected from the same group as R ¹ to R ⁹ .

The so-called condensed ring and aliphatic ring formed between adjacent substituents means that any two adjacent substituents (for example, R ¹ and R ^{2 of} general formula (1)) are bonded to each other to form conjugated or non-coordinated The cyclic skeleton of the yoke. As constituent elements of such a condensed ring and aliphatic ring, in addition to carbon, an element selected from nitrogen, oxygen, sulfur, phosphorus, and silicon may be contained. In addition, these condensed rings and aliphatic rings may be further condensed with other rings.

The compound represented by the general formula (1) exhibits a high emission quantum yield and a small half-height width of the emission spectrum, and therefore can achieve both efficient color conversion and high color purity. Furthermore, the compound represented by the general formula (1) can adjust various characteristics or physical properties such as luminous efficiency, color purity, thermal stability, light stability, and dispersibility by introducing suitable substituents to suitable positions. For example, compared with the case where all of R ¹ , R ³ , R ⁴ and R ⁶ are hydrogen, at least one of R ¹ , R ³ , R ⁴ and R ⁶ is a substituted or unsubstituted alkyl group or a The substituted or unsubstituted aryl group and the substituted or unsubstituted heteroaryl group show better thermal stability and light stability.

When at least one of R ¹ , R ³ , R ⁴ and R ⁶ is a substituted or unsubstituted alkyl group, the alkyl group is preferably methyl, ethyl, n-propyl, isopropyl Alkyl groups with 1 to 6 carbon atoms such as butyl group, n-butyl group, second butyl group, tertiary butyl group, pentyl group and hexyl group. Furthermore, the alkyl group is preferably a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a second butyl group, and a tertiary butyl group from the viewpoint of excellent thermal stability. In addition, from the viewpoint of preventing concentration extinction and improving the emission quantum yield, the alkyl group is more preferably a three-dimensionally bulky tertiary butyl group. On the other hand, from the viewpoint of ease of synthesis and ease of obtaining raw materials, as the alkyl group, a methyl group can also be preferably used.

When at least one of R ¹ , R ³ , R ⁴ and R ⁶ is a substituted or unsubstituted aryl group, the aryl group is preferably phenyl, biphenyl, terphenyl, naphthalene The group is more preferably a phenyl group or a biphenyl group. Particularly preferred is phenyl.

In the case where at least one of R ¹ , R ³ , R ⁴ and R ⁶ is a substituted or unsubstituted heteroaryl group, the heteroaryl group is preferably pyridyl, quinolyl, and thienyl, More preferred are pyridyl and quinolinyl. Pyridyl is particularly preferred.

When all of R ¹ , R ³ , R ⁴ and R ⁶ may be the same or different, and are substituted or unsubstituted alkyl groups, the solubility in the binder resin or solvent is good, so it is more good. In this case, the alkyl group is preferably a methyl group from the viewpoints of ease of synthesis and ease of obtaining raw materials.

In the case where R ¹ , R ³ , R ⁴ and R ⁶ may be the same or different, and are substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl, it shows Better thermal stability and light stability are preferred. In this case, it is more preferable that each of R ¹ , R ³ , R ⁴ and R ⁶ may be the same or different, and is a substituted or unsubstituted aryl group.

Although there are substituents that improve multiple properties, there are a limited number of substituents that exhibit sufficient performance in all properties. In particular, it is difficult to combine high luminous efficiency with high color purity. Therefore, by introducing various substituents to the compound represented by the general formula (1), it is possible to obtain a compound that is balanced in terms of light-emitting characteristics, color purity, and the like.

In particular, when R ¹ , R ³ , R ⁴ and R ⁶ may be the same or different, and are substituted or unsubstituted aryl groups, for example, R ¹ ≠R ⁴ , R ³ ≠ R ⁶ , R ¹ ≠R ³ or R ⁴ ≠R ⁶ generally introduce various substituents. Here, "≠" represents the basis of different structures. For example, R ¹ ≠R ⁴ indicates that R ¹ and R ⁴ are groups of different structures. By introducing a variety of substituents as described above, it is possible to simultaneously introduce an aryl group that affects color purity and an aryl group that affects luminous efficiency, so fine adjustments can be made.

Among them, from the viewpoint of improving luminous efficiency and color purity with a good balance, R ¹ ≠R ³ or R ⁴ ≠R ^{6 is} preferred. In this case, with respect to the compound represented by the general formula (1), one or more aryl groups that affect the color purity can be introduced into the pyrrole rings on both sides, and the light-emitting group can be introduced in other positions. The efficiency of the aryl group affects, therefore, the properties of both can be maximized. In addition, in the case of R ¹ ≠R ³ or R ⁴ ≠R ⁶ , from the viewpoint of improving both heat resistance and color purity, R ¹ =R ⁶ and R ³ =R ⁴ are more preferable.

The aryl group that mainly affects color purity is preferably an aryl group substituted with an electron-donating group. The so-called electron-donating group, in the theory of organic electronics, refers to an atomic group that supplies electrons to the substituted atomic group through an induction effect or a resonance effect. As the electron-donating group, a negative value can be used as the substituent constant (σp (pair)) of the Hammett equation. The substituent constant (σp (pair)) of the Hammett equation can be quoted from the 5th edition of the Basics of Chemistry (page II-380).

Specific examples of the electron-donating group include, for example, an alkyl group (σp of methyl group: -0.17), an alkoxy group (σp of methoxy group: -0.27), and an amino group (σp of -NH ₂ : -0.66). Wait. Particularly, an alkyl group having 1 to 8 carbons or an alkoxy group having 1 to 8 carbons is preferable, and a methyl group, an ethyl group, a tertiary butyl group, and a methoxy group are more preferable. From the viewpoint of dispersibility, tertiary butyl and methoxy are particularly preferred. When these are used as the electron-donating group, in the compound represented by the general formula (1), Prevents the extinction caused by the aggregation of molecules. The substitution position of the substituent is not particularly limited, but in order to improve the light stability of the compound represented by the general formula (1), it is necessary to suppress the bending of the bond, so it is preferably relative to the bonding position with the pyrromethene skeleton The bond is in meta or counterpoint. On the other hand, as an aryl group that mainly affects luminous efficiency, an aryl group having bulky substituents such as a tertiary butyl group, an adamantyl group, and a methoxy group is preferable.

In the case where R ¹ , R ³ , R ⁴ and R ⁶ may be the same or different, and are substituted or unsubstituted aryl groups, it is preferable that R ¹ , R ³ , R ⁴ and R ⁶ may each be The same may be different, and it is a substituted or unsubstituted phenyl group. In this case, R ¹ , R ³ , R ⁴ and R ^{6 are more} preferably selected from the following Ar-1 to Ar-6. In this case, preferred combinations of R ¹ , R ³ , R ⁴ and R ⁶ include the combinations shown in Tables 1-1 to 1-11, but they are not limited to these combinations.

[Chem 2]

[Table 1-1] (Table 1-1)

[Table 1-2] (Table 1-2)

[Table 1-3] (Table 1-3)

[Table 1-4] (Table 1-4)

[Table 1-5] (Table 1-5)

[Table 1-6] (Table 1-6)

[Table 1-7] (Table 1-7)

[Table 1-8] (Table 1-8)

[Table 1-9] (Table 1-9)

[Table 1-10] (Table 1-10)

[Table 1-11] (Table 1-11)

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

R ⁸ and R ^{9 are} preferably alkyl, aryl, heteroaryl, alkoxy, aryl ether, fluorine, fluorine-containing alkyl, fluorine-containing heteroaryl or fluorine-containing aryl, fluorine-containing alkoxy , Fluorine-containing aryl ether group and cyano group are more preferably fluorine, cyano group or fluorine-containing aryl group in terms of being stable with respect to excitation light and obtaining higher fluorescence quantum yield. In terms of ease of synthesis, fluorine or cyano is further preferred. Furthermore, any one of R ⁸ or R ⁹ is preferably a cyano group. By introducing cyano groups, durability is improved.

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

In addition, in the general formula (1), from the viewpoint of light stability, X is preferably CR ⁷ . When X is CR ⁷ , the substituent R ⁷ greatly affects the durability of the compound represented by the general formula (1), that is, the luminescence intensity of the compound decreases with time. Specifically, when R ⁷ is hydrogen, the reactivity of this part is high, so this part easily reacts with moisture or oxygen in the air. This causes decomposition of the compound represented by the general formula (1). In addition, when R ⁷ is a substituent with a large degree of freedom of movement of a molecular chain such as an alkyl group, the reactivity is certainly reduced, but the compounds in the color conversion sheet aggregate with each other over time, resulting in concentration extinction. The luminous intensity is reduced. Therefore, R ^{7 is} preferably a group that is rigid and has a low degree of freedom of movement and is difficult to cause aggregation. Specifically, it is preferably a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group Any of them.

In terms of providing higher fluorescence quantum yield and making thermal decomposition more difficult, and in terms of light stability, it is preferable that X is CR ⁷ and R ⁷ is a substituted or unsubstituted aryl group. . The aryl group is preferably a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a phenanthryl group, and an anthracenyl group from the viewpoint of lossless emission wavelength.

Furthermore, in order to improve the light stability of the compound represented by the general formula (1), it is necessary to appropriately suppress the bending of the carbon-carbon bond between R ⁷ and the pyrromethene skeleton. The reason is that if the bending is too large, the reactivity to excitation light becomes high, and the light stability decreases. From this viewpoint, R ^{7 is} preferably substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted The substituted naphthyl group is more preferably a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, and a substituted or unsubstituted terphenyl group. Particularly preferred is substituted or unsubstituted phenyl.

In addition, R ^{7 is} preferably a suitably bulky substituent. Since R ⁷ has a large volume to some extent, aggregation of molecules can be prevented, and as a result, the luminous efficiency or durability of the compound represented by the general formula (1) is further improved.

於通式（2）中，r選自由氫、烷基、環烷基、雜環基、烯基、環烯基、炔基、羥基、硫醇基、烷氧基、烷硫基、芳基醚基、芳基硫醚基、芳基、雜芳基、鹵素、氰基、醛基、羰基、羧基、酯基、胺甲醯基、胺基、硝基、矽烷基、矽氧烷基、氧硼基、磺基、氧化膦基所組成的群組中。k為1～3的整數。於k為2以上的情況下，r分別可相同亦可不同。As a more preferable example of such a bulky substituent, the structure of R ⁷ represented by the following general formula (2) can be cited. [Chemical 3]

In the general formula (2), r is selected from hydrogen, alkyl, cycloalkyl, heterocyclyl, alkenyl, cycloalkenyl, alkynyl, hydroxyl, thiol, alkoxy, alkylthio, aryl Ether group, aryl sulfide group, aryl group, heteroaryl group, halogen, cyano group, aldehyde group, carbonyl group, carboxyl group, ester group, aminomethanyl group, amine group, nitro group, silyl group, siloxyalkyl group, In the group consisting of oxyboron group, sulfo group and phosphine oxide group. k is an integer of 1-3. When k is 2 or more, r may be the same or different.

From the viewpoint of providing a higher emission quantum yield, r is preferably a substituted or unsubstituted aryl group. Among the aryl groups, phenyl and naphthyl are particularly preferred examples. When r is an aryl group, k of the general formula (2) is preferably 1 or 2, and among them, from the viewpoint of further preventing the aggregation of molecules, 2 is more preferable. Furthermore, when k is 2 or more, at least one of r is preferably substituted with an alkyl group. As the alkyl group in this case, a methyl group, an ethyl group, and a tertiary butyl group can be cited as particularly preferable examples from the viewpoint of thermal stability.

In addition, from the viewpoint of controlling the fluorescence wavelength or absorption wavelength, or improving the compatibility with the solvent, r is preferably a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, or a halogen. , More preferably methyl, ethyl, tertiary butyl, methoxy. From the viewpoint of dispersibility, tertiary butyl and methoxy are particularly preferred. In terms of preventing the extinction caused by the aggregation of molecules, it is more effective that r is a tertiary butyl group or a methoxy group.

In addition, as another aspect of the compound represented by the general formula (1), it is preferable that at least one of R ¹ to R ⁷ is an electron withdrawing group. Particularly preferably (1) at least one of R ¹ to R ⁶ is an electron withdrawing group; (2) R ⁷ is an electron withdrawing group; or (3) at least one of R ¹ to R ⁶ is an electron withdrawing group And R ⁷ is an electron withdrawing group. By introducing an electron withdrawing group into the pyrromethene skeleton of the compound as described above, the electron density of the pyrromethene skeleton can be greatly reduced. Thereby, the stability of the compound with respect to oxygen is further improved, and as a result, the durability of the compound can be further improved.

The so-called electron withdrawing group, also known as an electron withdrawing group, is an atomic group that attracts electrons from a substituted atomic group through an induction effect or a resonance effect in organic electron theory. As the electron withdrawing group, one having a positive value as the substituent constant (σp (para position)) of Hammett's rule can be cited. The substituent constant (σp (pair)) of the Hammett equation can be quoted from the 5th edition of the Basics of Chemistry (page II-380). Furthermore, although the phenyl group also has an example of taking a positive value as described above, in the present invention, the phenyl group is not included in the electron withdrawing group.

Examples of electron withdrawing groups include -F (σp: +0.06), -Cl (σp: +0.23), -Br (σp: +0.23), -I (σp: +0.18), -CO ₂ R ¹² (σp: +0.45 when R ¹² is ethyl), -CONH ₂ (σp: +0.38), -COR ¹² (σp: +0.49 when R ¹² is methyl), -CF ₃ (σp: + 0.50), -SO ₂ R ¹² (σp: +0.69 when R ¹² is a methyl group), -NO ₂ (σp: +0.81), etc. R ¹² each independently represents a hydrogen atom, a substituted or unsubstituted ring-forming aromatic hydrocarbon group having 6 to 30 carbon atoms, a substituted or unsubstituted ring-forming heterocyclic group having 5 to 30 atoms, a substituted or Unsubstituted alkyl having 1 to 30 carbons, substituted or unsubstituted cycloalkyl having 1 to 30 carbons. As specific examples of these respective groups, the same examples as described above can be cited.

In the general formula (1), at least one of R ² and R ⁵ is preferably an electron withdrawing group. The reason is: R ² and R ⁵ of the general formula (1) are substitution positions that have a greater influence on the electron density of the pyrromethene skeleton. By introducing electron withdrawing groups to R ² and R ⁵ , it can be effectively reduced The electron density of the pyrromethene skeleton and the stability to oxygen are further improved, so the durability can be further improved.

Furthermore, in the general formula (1), R ² and R ^{5 are more} preferably electron withdrawing groups. The reason is that the stability of the compound represented by the general formula (1) to oxygen is further improved, and durability can be greatly improved. The electron withdrawing group is preferably a group containing a fluorine atom. By being a group containing a fluorine atom, the electron density of the pyrromethene skeleton can be further reduced, the stability of the compound represented by the general formula (1) to oxygen is improved, and the durability can be improved.

Preferred electron withdrawing groups include: fluorine, fluorine-containing aryl, fluorine-containing heteroaryl, fluorine-containing alkyl, substituted or unsubstituted carbonyl, substituted or unsubstituted ester group, and substituted Or unsubstituted amide group, substituted or unsubstituted sulfonamide group, substituted or unsubstituted sulfonate group, substituted or unsubstituted sulfonamide group or cyano group. The reason is that these groups are difficult to chemically decompose. More preferable electron withdrawing groups include: fluorine-containing alkyl groups, substituted or unsubstituted carbonyl groups, substituted or unsubstituted ester groups, substituted or unsubstituted amide groups, substituted or unsubstituted amide groups, and A substituted sulfonyl group, a substituted or unsubstituted sulfonate group, a substituted or unsubstituted sulfonamide group or a cyano group. The reason is that these groups have the effects of preventing concentration extinction and improving the emission quantum yield. A particularly preferred electron withdrawing group is a substituted or unsubstituted ester group.

Further preferable electron withdrawing groups include fluorine-containing carbonyl group, fluorine-containing ester group, fluorine-containing amide group, fluorine-containing sulfonamide group, fluorine-containing sulfonate group, and fluorine-containing sulfonamide group. These groups can effectively reduce the electron density of the pyrromethene boron complex skeleton. Thereby, the stability of the compound represented by general formula (1) to oxygen is improved, and as a result, durability can be further improved. Among them, since it is possible to improve durability without reducing color purity, it is preferable that at least one of R ² and R ⁵ may be the same or different, and be a substituted or unsubstituted ester group. In particular, from the viewpoint of improvement in durability, it is particularly preferable that both R ² and R ⁵ may be the same or different, and are substituted or unsubstituted ester groups.

As a preferable example of the compound represented by the general formula (1), the following cases can be cited: R ¹ , R ³ , R ⁴ and R ⁶ may be the same or different, and are substituted or unsubstituted X is CR ⁷ and R ⁷ is a group represented by general formula (2). In this case, R ^{7 is} particularly preferably a group represented by general formula (2) containing r as a substituted or unsubstituted phenyl group.

In addition, as another preferable example of the compound represented by the general formula (1), the following cases can be cited: R ¹ , R ³ , R ⁴ and R ⁶ may be the same or different, and are selected from the above Among Ar-1 to Ar-6, X is CR ⁷ and R ⁷ is a group represented by the general formula (2). In this case, R ^{7 is more} preferably a group represented by the general formula (2) containing r as a tertiary butyl group and a methoxy group, and particularly preferably a group represented by the general formula (2) containing r as a methoxy group ).

In addition, as another preferable example of the compound represented by the general formula (1), the following cases can be cited: R ¹ , R ³ , R ⁴ and R ⁶ may be the same or different, and are substituted or An unsubstituted alkyl group, and R ² and R ⁵ are the same or different, and are substituted or unsubstituted ester groups, and X is CR ⁷ and R ⁷ is a group represented by the general formula (2) . In this case, R ^{7 is} particularly preferably a group represented by general formula (2) containing r as a substituted or unsubstituted phenyl group.

In addition, as another preferable example of the compound represented by the general formula (1), the following cases can be cited: R ¹ , R ³ , R ⁴ and R ⁶ may be the same or different, and are selected from the above In Ar-1 to Ar-6, R ² and R ⁵ are the same or different, and are substituted or unsubstituted ester groups, and X is CR ⁷ and R ⁷ is represented by the general formula (2)的基。 The base. In this case, R ^{7 is more} preferably a group represented by the general formula (2) containing r as a tertiary butyl group and a methoxy group, and particularly preferably a group represented by the general formula (2) containing r as a methoxy group ).

An example of the compound represented by general formula (1) is shown below, but the compound is not limited to these. [Chem 4]

[Chemical 5]

[化6]

[化7]

[化8]

[化9]

[化10]

[Chem 11]

[化12]

[Chem 13]

[化14]

[化15]

[Chem 16]

[化17]

[Chemical 18]

[化19]

[化20]

[化21]

[化22]

[化23]

[化24]

[化25]

[化26]

[化27]

[Chem 28]

The compound represented by the general formula (1) can be synthesized by a method described in, for example, Japanese Patent Application Publication No. Hei 8-509471 or Japanese Patent Application Publication No. 2000-208262. That is, the target pyrromethene-based metal complex compound can be obtained by reacting the pyrromethene compound and the metal salt in the coexistence of a base. In addition, for the synthesis of pyrromethene-boron fluoride complexes, please refer to "Journal of Organic Chemistry (J. Org. Chem.)", vol.64, No.21, pp.7813-7819 (1999), The method described in "Applied Chemistry International Edition (English) (Angew. Chem., Int. Ed. Engl.)", vol. 36, pp. 1333-1335 (1997), etc. The synthesis is represented by the general formula (1) Represents the compound. For example, the following method can be cited: the compound represented by the following general formula (3) and the compound represented by the general formula (4) are heated in the presence of phosphorus oxychloride in 1,2-dichloroethane Then, it reacts with a compound represented by the following general formula (5) in 1,2-dichloroethane in the presence of triethylamine, thereby obtaining a compound represented by the general formula (1). However, the present invention is not limited to this. Here, R ¹ to R ⁹ are the same as the above description. J represents halogen.

[Chem 29]

Furthermore, when introducing an aryl group or a heteroaryl group, a method of forming a carbon-carbon bond by a coupling reaction of a halogenated derivative and a boric acid or a borated derivative can be mentioned, but the present invention is not limited to this. Similarly, when introducing an amine group or a carbazole group, for example, a method of forming a carbon-nitrogen bond by the coupling reaction of a halogenated derivative under a metal catalyst such as palladium and an amine or carbazole derivative can also be cited. It is not limited to this.

In addition to the compound represented by the general formula (1), the color conversion composition of the embodiment of the present invention may contain other compounds as necessary. For example, in order to further increase the energy transfer efficiency from the excitation light to the compound represented by the general formula (1), 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 (1), a desired organic luminescent material can be added, such as coumarin-based dyes, rhodamine-based dyes, etc. Organic light-emitting materials. In addition, in addition to these organic light-emitting materials, well-known light-emitting materials such as inorganic phosphors, fluorescent pigments, fluorescent dyes, and quantum dots may also be added in combination.

An example of organic light-emitting materials other than the compound represented by the general formula (1) is shown below, but the present invention is not particularly limited to these. [化30]

(Wavelength limitation, Forster) The color conversion composition of the present invention preferably contains a first luminescent material: by using excitation light having a wavelength in the range of 400 nm or more and 500 nm or less, a peak is observed in a region of 500 nm or more and less than 580 nm Wavelength of luminescence. From now on, light emission with a peak wavelength observed in the region above 500 nm and less than 580 nm is called "green light emission." In addition, the color conversion composition of the present invention preferably contains a second luminescent material that is excited by either or both of excitation light having a wavelength ranging from 400 nm to 500 nm or light emission from the first luminescent material , And the peak wavelength of luminescence is observed in the region above 580 nm and below 750 nm. From now on, light emission with a peak wavelength observed in the region above 580 nm and below 750 nm is called "red emission." Generally, the greater the energy of the excitation light, the easier it is to cause the decomposition of the material. However, the excitation light in the range of 400 nm or more and 500 nm or less has a relatively small excitation energy. Therefore, it is possible to obtain light emission with good color purity without causing decomposition of the luminescent material in the color conversion composition.

In the color conversion composition of the present invention, the first luminescent material and the second luminescent material may include only either one or both. In addition, the first luminescent material may be used alone or in combination of multiple types. Similarly, the second luminescent material may be used alone or in combination of multiple types. Part of the excitation light in the range of 400 nm or more and 500 nm or less partially transmits through the color conversion composition of the present invention, so it can be used as blue light emission. Therefore, the color conversion composition of the present invention contains a first luminescent material that emits green light and a second luminescent material that emits red light. When a blue LED with a sharp emission peak is used as blue light, it can be obtained It shows white light with a sharp emission spectrum and good color purity in each of blue, green, and red colors. As a result, especially in displays, it is possible to efficiently form more vivid colors and a larger color gamut. In addition, in lighting applications, compared with the current mainstream white LEDs composed of a combination of blue LEDs and yellow phosphors, the light emission characteristics of the green region and the red region are improved, so that the color rendering properties are improved. Excellent white light source.

Examples of the first luminescent material include coumarin derivatives such as coumarin 6, coumarin 7, and coumarin 153; cyanine derivatives such as indocyanine green; fluorescent yellow and fluorescent yellow isothiocyanate Fluorescent yellow derivatives such as acid ester, carboxyl fluorescent yellow diacetate; Phthalocyanine derivatives such as phthalocyanine green; Perylene derivatives such as diisobutyl-4,10-dicyanoperylene-3,9-dicarboxylate物; and pyrrole methylene derivatives, stilbene derivatives, oxazine derivatives, naphthalimide derivatives, pyrazine derivatives, benzimidazole derivatives, benzoxazole derivatives, benzo Suitable compounds such as thiazole derivatives, imidazopyridine derivatives, azole derivatives, anthracene, and the like, which have condensed aryl rings, or derivatives thereof, aromatic amine derivatives, organometallic complex compounds, and the like. However, the first luminescent material is not particularly limited to these compounds. Among these compounds, pyrromethene derivatives are particularly suitable compounds because they provide high emission quantum yields and have good durability. As the pyrromethene derivative, for example, the compound represented by the general formula (1) is preferable because it exhibits excellent and highly pure luminescence.

As the second luminescent material, cyanine derivatives such as 4-dicyanomethylene-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran; Rhodamine B , Rhodamine 6G, rhodamine 101, sulforhodamine 101 and other rhodamine derivatives; 1-ethyl-2-(4-(p-dimethylaminophenyl)-1,3-butyl Dienyl)-pyridinium-perchlorate and other pyridine derivatives; N,N'-bis(2,6-diisopropylphenyl)-1,6,7,12-tetraphenoxyperylene- Perylene derivatives such as 3,4:9,10-bisdicarbimines; as well as porphyrin derivatives, pyrromethene derivatives, oxazine derivatives, pyrazine derivatives, condensed tetraphenyl or dibenzobis A compound having a condensed aryl ring such as indenoperylene or a derivative thereof, an organometallic complex compound, etc. are suitable. However, the second luminescent material is not particularly limited to these compounds. Among these compounds, pyrromethene derivatives are particularly suitable compounds because they provide high emission quantum yields and have good durability. As the pyrromethene derivative, for example, the compound represented by the general formula (1) is preferable because it exhibits excellent and highly pure luminescence.

Although the content of the luminescent material in the color conversion composition of the embodiment of the present invention also depends on the molar absorption coefficient of the compound, the emission quantum yield, and the absorption intensity in the excitation wavelength, and the thickness or transmission of the color conversion layer produced However, it is usually 1.0×10 ^-4 parts by mass to 30 parts by mass relative to 100 parts by mass of the resin contained in the color conversion layer. Among them, it is more preferably 1.0×10 ^-3 parts by mass to 10 parts by mass, and particularly preferably 5.0×10 ^-3 parts by mass to 5 parts by mass. In addition, when the color conversion composition contains both a first luminescent material that emits green light and a second luminescent material that emits red light, in terms of converting part of the green light emission into red light emission, the first The ratio of the molar content n ₁ of the luminescent material to the molar content n ₂ of the second luminescent material is n ₁ :n ₂ =100:1 to 1:100, preferably 20:1 to 1:20, and further It is preferably 5:1 to 1:5, particularly preferably 0.7:1 to 1:0.7. Here, the molar content n ₁ and the molar content n ₂ are the amounts of substances contained in the matrix resin of the color conversion layer described later.

＜Matrix resin＞ The matrix resin used in the present invention is a resin that forms a continuous phase, as long as it is a material excellent in molding processability, transparency, heat resistance, and the like. In the present invention, a matrix resin that does not cause a photohardening reaction is preferable. Furthermore, in this invention, it is more preferable that it is a matrix resin which does not cause a thermosetting reaction other than a photocuring reaction. As the resin, a thermoplastic resin can be preferably used. In the case of using a thermoplastic resin, free radicals will not be generated due to light irradiation or heat, the deterioration of the pyrromethene derivative can be prevented, and the color conversion efficiency or durability can be improved, which is preferable. In addition, it is possible to prevent the generation of free radicals over time, and therefore does not cause deterioration of the pyrromethene derivative, resulting in improved durability, which is preferable.

As specific resins, for example, urea resin, fluororesin, polycarbonate resin, acrylic resin, methacrylic resin, polyimide resin, cyclic olefin resin, polyethylene terephthalate resin, polypropylene can be used. Resin, polystyrene resin, urethane resin, polyethylene resin, polyamide resin, polyvinyl alcohol resin, cellulose resin, aliphatic ester resin, aromatic ester resin, aliphatic polyolefin resin, aromatic Known persons such as polyolefin resin. In addition, these copolymer resins can also be used. Among these resins, acrylic resins, ester resins, or mixtures of these resins can be suitably used from the viewpoint of transparency. In addition to transparency, from the viewpoint of heat resistance, acrylic resins and ester resins can be more preferably used.

＜Other additives＞ The color conversion composition of the present invention may contain additives within a range that does not impair the effects of the present invention. Specific examples of additives include: dispersion stabilizers, leveling agents, antioxidants, flame retardants, defoamers, plasticizers, crosslinking agents, hardeners, ultraviolet absorbers, and other light resistance stabilizers Adhesives such as chemical agents, silane coupling agents, etc. In addition, no photopolymerizable initiator is included in the present invention. In the absence of a photopolymerizable initiator, it prevents the generation of free radicals caused by light irradiation or heat, and does not cause deterioration of the pyrromethene derivative. Therefore, color conversion efficiency or durability can be improved. In addition, since the generation of free radicals caused by time can be prevented, the deterioration of the pyrromethene derivative is not caused. As a result, durability is improved, which is preferable. In addition, the color conversion composition of the present invention preferably does not contain a thermally polymerizable initiator. In the absence of a thermally polymerizable initiator, the generation of radicals caused by thermal reactions can be suppressed. As a result, the color conversion efficiency and durability are improved, which is preferable.

＜Color conversion layer＞ The color conversion layer of the present invention is a cured product containing the color conversion composition. In order to exert a sufficient color conversion function, the film thickness of the color conversion layer is preferably 1 μm or more, more preferably 5 μm or more. On the other hand, from the viewpoint of suppressing pixel defects, it is preferably 100 μm or less, and more preferably 50 μm or less. The film thickness can be calculated by measuring the height of the step using a stylus-type film thickness measuring device. More specifically, a part of the color conversion layer is scratched with a needle or the like to expose the lower layer of the substrate, etc., and the thickness of the film can be obtained by observing the film thickness from above the color conversion layer with a stylus thickness gauge. .

＜Wavelength conversion substrate＞ The wavelength conversion substrate of the present invention has a color conversion function of converting incident light into light having a longer wavelength than the incident light, and is formed of a transparent substrate and the color conversion layer. Here, the term “transparency” means that the transmittance of light with a wavelength of 400 nm to 800 nm is all 90% or more. Examples of transparent substrates include glass plates, resin plates, and resin films. As the material of the glass plate, alkali-free glass is preferred. As the material of the resin plate and the resin film, polyester resin, acrylic resin, transparent polyimide resin, polyether resin, etc. are preferred. The thickness of the glass plate and the resin plate is preferably 1 mm or less, more preferably 0.6 mm or less. The thickness of the resin film is preferably 100 μm or less. The wavelength conversion substrate 11 of the present invention is provided with a color conversion layer on the transparent substrate 1, for example, as shown in FIGS. 1, 4 and 7, it includes a red conversion layer 3 and a green conversion layer 4. The color conversion layer preferably includes a plurality of color conversion layers, but there may be one color conversion layer. In addition, the wavelength conversion substrate 11 may be formed with a partition wall 2, and the red conversion layer 3 and the green conversion layer 4 are preferably arranged between the partition wall and the partition wall (a recess). In addition, the wavelength conversion substrate 11 preferably has color filters such as a red color filter 9, a green color filter 10, and a blue color filter 14, as shown in FIGS. 4 and 7. The excitation light may be incident from the transparent substrate 1 side and the visibility may be performed from the opposite side of the transparent substrate 1, or the excitation light may be incident from the color conversion layer side and the visibility may be performed from the transparent substrate 1 side. Regarding the measurement of the quantum yield when the wavelength conversion substrate is used as a sample, when the color conversion substrate is irradiated with blue light with a peak wavelength of 440 nm to 460 nm, it is usually 0.5 or more, preferably 0.7 or more, more preferably 0.8 or more, and further Preferably, it is 0.9 or more.

<Concave portion> The recessed portion of the wavelength conversion substrate 11 of the present invention refers to a region partitioned by arranging the partition wall 2 in a pattern corresponding to a plurality of light sources. In FIGS. 1 to 3, the area partitioned by the partition wall 2 arranged in a pattern on the transparent substrate 1 corresponds to a concave portion. The material that can be used for the partition wall 2 can be either photosensitive resin or non-photosensitive resin. Specifically, epoxy resin, acrylic resin, silicone polymer resin, polyimide resin can be preferably used. Wait. The partition wall 2 can also be used to form a predetermined thin film by wet coating methods such as spin coating, dip coating, roll coating, gravure coating, dispenser, etc., and further include resist coating, prebaking, exposure, development, etc. Photolithography methods such as post-baking, etching, and resist removal are used to create patterns. In addition, when solid materials such as LiF and MgF ₂ are used to form the partition wall, the film can be formed by a dry process such as vacuum vapor deposition and sputtering, and then a predetermined dry process such as photolithography or etching can be used to form the film. pattern. The film thickness of the partition wall 2 is preferably greater than the film thickness of the color conversion layer, and is preferably in the range of 0.5 μm to 50 μm. In addition, the pattern of the partition wall 2 may be sufficient to prevent color mixing with the color conversion layer formed in the adjacent recess, and is preferably formed in a width of 1 μm to 20 μm, and more preferably in a width of 5 μm to 15 μm. .

＜How to make color conversion composition＞ Hereinafter, an example of the method of producing the color conversion composition of the present invention will be described. In addition, the manufacturing method described below is an example, and the manufacturing method of a color conversion composition is not limited to this. A predetermined amount of the pyrromethene derivative, matrix resin, inorganic particles having a refractive index of 1.7 to 2.8, additives, solvents, and the like are mixed as necessary. After the ingredients are mixed so as to have a predetermined composition, the mixture is homogeneously mixed and dispersed by a homogenizer, a rotating mixer, a three-roller, a ball mill, a planetary ball mill, a bead mill, and other mixing and kneading machines. Thereby, a color conversion composition can be obtained. After mixing and dispersing, or in the process of mixing and dispersing, it is also preferable to perform defoaming under vacuum or reduced pressure. In addition, a certain specific component may be mixed in advance, or treatment such as aging may be applied to the color conversion composition produced. An evaporator can also be used to remove the solvent from the mixture after mixing and dispersion to adjust to a desired solid content concentration.

The color conversion composition of the present invention preferably has a high viscosity. When the color conversion composition has a high viscosity, the pyrromethene derivative and the inorganic particles can be uniformly dispersed. Therefore, when applied to a wavelength conversion substrate, good color conversion efficiency can be obtained. The color conversion composition of the present invention preferably has a viscosity at 25°C of 0.2 Pa·s or more and 50 Pa·s or less. If the viscosity of the color conversion composition at 25° C. is 0.2 Pa·s or more, the sedimentation of inorganic particles can be suppressed and the optical path length can be increased, so the color conversion efficiency of the pyrromethene derivative can be improved. From the viewpoint of improving the color conversion efficiency, it is preferably 0.2 Pa·s or more, more preferably 2 Pa·s or more, and still more preferably 10 Pa·s or more. In addition, if the viscosity of the color conversion composition at 25°C is 50 Pa·s or less, the dispersion of inorganic particles becomes easier, and therefore the aggregation of inorganic particles can be suppressed and the optical path length can be increased, thereby increasing the pyrromethene derivative The color conversion efficiency of objects.

＜How to make the color conversion layer＞ The color conversion composition is coated on a substrate and dried to prepare a color conversion layer. Coating can use reverse roll coater, knife coater, slot die coater, direct gravure coater, offset gravure coater, kiss coater, forward roll coater (natural roll coater) coater), air knife coater, roller blade coater, two-stream coater (two-stream coater), bar coater, wire bar coater, applicator, dip coater, curtain coating Machine, spin coater, knife coater, etc. The color conversion layer can be dried using a general heating device such as a hot air dryer or an infrared dryer. In this case, the drying conditions are usually 1 minute to 5 hours at 40°C to 250°C, preferably 2 minutes to 4 hours at 60°C to 200°C. In addition, staged drying such as step cure can also be performed.

<Method for manufacturing wavelength conversion substrate> Hereinafter, an example of the manufacturing method of the wavelength conversion substrate of the present invention will be described. In addition, the manufacturing method described below is an example, and the manufacturing method of a wavelength conversion board|substrate is not limited to this. The wavelength conversion substrate of the present invention includes the color conversion layer. As a method of manufacturing the wavelength conversion substrate, the following method can be preferably used: a method of making the color conversion composition and patterning the color conversion layer using inkjet printing or screen printing, or coating by slit die A method of pattern formation by cloth or nozzle coating. The wavelength conversion substrate of the present invention can cope with coating solutions of various color conversion compositions ranging from low viscosity to high viscosity. In order to obtain thicker or uniform thickness of the color conversion layer, it is preferable to coat by a slit die Or nozzle coating to pattern the color conversion layer. In particular, in order to pattern ultra-fine patterns with high precision, it is preferable to use nozzle coating or slit die coating using a slit die after microprocessing. In addition, the drying of the wavelength conversion substrate can be performed using a general heating device such as a hot air dryer or an infrared dryer. In this case, the drying conditions are usually 1 minute to 5 hours at 40°C to 250°C, preferably 2 minutes to 4 hours at 60°C to 200°C. In addition, staged drying such as stage hardening is also possible.

＜Color filter＞ Furthermore, the wavelength conversion substrate of the present invention preferably has the color conversion layer and the color filter of the present invention. As the color filter, as illustrated in FIGS. 4 to 9, a red color filter 9, a green color filter 10, and a blue color filter 14 can be used. The color filter is a layer for transmitting a specific wavelength region of visible light, setting the transmitted light to a desired hue, and improving the color purity of the transmitted light. By using a color filter for the wavelength conversion substrate 11, it is possible to selectively cut off only the blue light from the excitation light source and extract only the converted light. As a result, the color purity is improved. The color filter used in the present invention can be formed using materials used in flat panel displays such as liquid crystal displays. As the material, a pigment dispersion type material in which a pigment is dispersed in a photoresist has been frequently used in recent years. As the color filter, it is preferable to use a blue color filter that transmits light in a wavelength range of 400 nm or more and 550 nm or less, and a green color filter that transmits light in a wavelength range of 500 nm or more and 600 nm or less. A light sheet, a yellow color filter that transmits light in a wavelength range of 500 nm or more, or a red color filter that transmits light in a wavelength range of 600 nm or more. In addition, the color filter can be laminated separately from the color conversion layer, or can be laminated integrally. In addition, a color filter can be formed on the wavelength conversion substrate, or a color filter substrate can be fabricated separately from the wavelength conversion substrate, and the wavelength conversion substrate and the color filter substrate can be overlapped and used. The color conversion layer and the color filter are preferably laminated in order from the light source.

As the color filter used in the present invention, a cured product of a color filter forming composition containing a color material and a binder resin can be preferably used, and more preferably a color material, a binder resin, and a reactive monomer can be used. It is a cured product of the composition for forming a color filter with a photopolymerization initiator and a photopolymerization initiator. As a color material, a pigment, a dye, etc. are mentioned. Examples of pigments include organic pigments and inorganic pigments. The color material may contain two or more of these. Among these, organic pigments and dyes are preferred. In this case, the light transmittance of the color filter can be improved. As the organic pigment of the red color material, for example, CI Pigment Red 9, 48, 97, 122, 123, 144, 149, 166, 168, 177, 179, 180, 192, 209, 215, 216, 217, 220, 223,224,226,227,228,240,254,255,256,257,258,260,261,264,266,267,268,269,273,274,291 etc. Examples of organic pigments for the yellow color material include CI Pigment Yellow 12, 13, 17, 20, 24, 83, 86, 93, 95, 109, 110, 117, 125, 129, 137, 138, 139, 147, 148 , 150, 153, 154, 166, 168, 180, 185, 231, etc. Examples of color materials of other colors include orange pigments such as C.I. Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, and 71.

Examples of dyes include oil-soluble dyes, acid dyes, direct dyes, basic dyes, and acid mordant dyes. The dye can be laked or used as a salt-forming compound between the dye and a nitrogen-containing compound. Specifically, for example, azo dyes, benzoquinone dyes, naphthoquinone dyes, anthraquinone dyes, xanthene dyes, cyanine dyes, squarylium dyes, crotonium dyes, Merocyanine dyes, stilbene dyes, diarylmethane dyes, triarylmethane dyes, Fluoran dyes, spiropyran dyes, phthalocyanine dyes, indigo dyes , Fulgide dyes, nickel complex dyes, azulene dyes, etc. As the color material used in the green color filter, for example, CI Pigment Green 1, 2, 4, 7, 8, 10, 13, 14, 15, 17, 18, 19, 26, 36, 45, 48, 50, 51, 54, 55, 58, 59, or CI Pigment Yellow 1, 1: 1, 2, 3, 4, 5, 6, 9, 10, 12, 13, 14, 16, 17, 24, 31, 32, 34, 35, 35: 1, 36, 36: 1, 37, 37: 1, 40, 41, 42, 43, 48, 53, 55, 61, 62, 62: 1, 63, 65, 73, 74, 75, 81, 83, 87, 93, 94, 95, 97, 100, 101, 104, 105, 108, 109, 110, 111, 116, 117, 119, 120, 126, 127, 127: 1, 128, 129, 133, 134, 136, 138, 139, 142, 147, 148, 150, 151, 153, 154, 155, 157, 158, 159, 160, 161, 162, 163, 164, 165, 166, 167, 168, 169, 170, 172, 173, 174, 175, 176, 180, 181, 182, 183, 184, 185, 188, 189, 190, 191, 191-1, 192, 193, 194, 195, 196, 197, 198, 199, 200, 202, 203, 204, 205, 206, 207, 211, 213, 218, 220, 221, 228, CI Pigment Blue 15, 15:1, 15:2, 15:3 , 15:4, 15:5, 15:6, 16, 60 and other pigments.

As the color material used in the blue color filter, for example, blue pigments such as CI Pigment Blue 15, 15:3, 15:4, 15:6, 16, 22, 60, 64, CI Pigment Violet 19, Violet pigments such as 23, 29, 30, 32, 37, 40, 50, acid red 59, 289, color materials shown in Japanese Patent Laid-Open No. 2011-032298, etc. These color materials can be dissolved in the composition for forming a color filter or dispersed in the form of particles. Among these color materials, from the viewpoint of further improving brightness, the color filter (especially the red color filter) preferably includes a red color material and a yellow color material. Furthermore, the yellow color material is more preferably at least one of C.I. Pigment Yellow 138, C.I. Pigment Yellow 139, C.I. Pigment Yellow 150, C.I. Pigment Yellow 180, C.I. Pigment Yellow 185, and C.I. Pigment Yellow 231.

The wavelength conversion substrate of the present invention increases the light intensity in a specific wavelength region by absorbing light of a color other than a specific color by the color conversion layer. Therefore, when the wavelength conversion substrate includes the color material, the wavelength selectivity of the color converted by the color conversion layer can be improved, and the color purity can be further improved.

As the binder resin, a resin that can prevent aggregation of color materials and uniformly disperse color materials and the like in the color filter layer is preferred. Specifically, as the binder resin, the resins exemplified previously as the resin contained in the color conversion layer can be cited. The thickness of each layer of the color filter and the color conversion layer can be calculated by measuring the height of the step using a stylus type film thickness measuring device. More specifically, the color filter layer or a part of the color conversion layer is scratched with a needle or the like to expose the lower layer of the substrate, etc., and the stylus film is used vertically from above the color filter layer or the color conversion layer By observing with a thickness gauge, the thickness of the target layer can be obtained.

In the present invention, when the line width of the color filter layer is W1 and the line width of the color conversion layer is W2, W1-W2 is preferably 1 μm or more and 30 μm or less. By setting W1-W2 to 1 μm or more, the influence of the color conversion layer on the light passing through the colored layer of other colors when viewed from an oblique direction can be suppressed, and the color purity or brightness can be further improved. On the other hand, by setting W1-W2 to 30 μm or less, the ratio of light passing through the color conversion layer and passing through the color filter can be increased, and the brightness or color purity can be further improved. The line width of each layer of the color filter and the color conversion layer can be measured by observing the pattern of the color filter layer or the color conversion layer at a magnification of 100 times using an optical microscope.

In addition, the wavelength conversion substrate of the present invention may further include: a resin black matrix provided between color filters of different colors; and an overcoat layer covering each component such as the color filter on the substrate. Examples of the overcoat layer include epoxy resin, acrylic epoxy resin, acrylic resin, silicone resin, polyimide resin, silicon-containing polyimide resin, polyimide silicone resin, etc. Film etc. Examples of materials that form the resin black matrix include materials containing binder resins such as acrylic resins and polyimide resins, and black pigments. Examples of black pigments include C.I. Pigment Black 7, carbon black, graphite, iron oxide, manganese oxide, titanium black, and the like. The resin black matrix may contain two or more of these, and may further contain pigments of other colors. Black pigments can be surface treated. The thickness of the resin black matrix is preferably 0.5 μm or more and 2 μm or less.

＜Display＞ The display of the present invention includes a light source that emits blue light or blue-green light, and at least the color conversion substrate of the present invention. The light source used in the present invention includes a plurality of light sources and is a partially driven self-luminous light source. As long as the light source can emit blue light or blue-green light that can excite the pyrromethene derivative of the color conversion layer, any light source can be used. For example, hot cathode tubes, cold cathode tubes, fluorescent light sources such as inorganic electroluminescence, organic EL element light sources, light-emitting diodes (hereinafter referred to as LED) light sources, incandescent light sources, or sunlight. In principle Can be used.

In FIGS. 2, 5, and 8, the micro LED 5 corresponds to a light source, and in FIGS. 3, 6 and 9, the organic EL element 7 corresponds to a light source. The excitation light may have one luminescence peak or two or more luminescence peaks, but in order to improve color purity, it is preferable to have one luminescence peak. In addition, a plurality of light sources with different types of emission peaks may be used in any combination.

The light source of the display of the present invention preferably has a maximum wavelength as blue light or blue-green light in the wavelength range of 430 nm to 500 nm, and the emission spectrum can be a single peak or a double peak. In addition, those having a maximum wavelength in the wavelength range of 430 nm to 500 nm also include YAG LEDs having the first peak in the wavelength range of 430 nm to 500 nm and the first peak in the wavelength range of 500 nm to 700 nm. In the case of 2 peaks, from the viewpoint of improving the color purity of blue, it is preferable not to have a maximum wavelength at 500 nm to 700 nm. In addition, it is more suitable for excitation light to have a peak in the wavelength range of 430 nm to 500 nm. The excitation light in the wavelength range of 430 nm to 500 nm has a small excitation energy and can prevent the decomposition of the luminescent substance of the pyrromethene derivative. Therefore, the light source used in the present invention is preferably a light source having extremely high luminescence in the wavelength range of 430 nm or more and 500 nm or less. Furthermore, the light source preferably has extremely high luminescence in a wavelength range of 440 nm or more and 470 nm or less.

The self-luminous light source used in the present invention is preferably an LED. If the light source is an LED, multiple light sources can be arranged with high precision, so a high-resolution display can be realized. In addition, the luminous intensity of the light-emitting diode is high, so a high-brightness display can be realized. In addition, in terms of improving the color purity of blue light, it is preferable that the LED has a gallium nitride-based compound semiconductor. Since the LED is a gallium nitride compound semiconductor, the luminescence of the excitation light can be made clear, and the color purity can be improved. The type of LED used in the present invention is not particularly limited. As far as it is used in the pixels of a display, micro LEDs (size 100 μm to 500 μm) and micro LEDs (<100 μm) are preferably used. ).

In addition, the self-luminous light source used in the present invention is preferably an organic EL element that has an organic layer between an anode and a cathode and emits light by electric energy. If the light source is an organic EL element that has an organic layer between an anode and a cathode and emits light by electric energy, not only a high-resolution display can be realized, but also a thinner display can be realized, so the display itself can be thinned.

As a representative example of the display of the present invention, a micro LED display is provided with a partially driven blue micro LED light source and a wavelength conversion substrate including the color conversion layer of the present invention. In an organic EL display, a partially driven type A light source for a blue organic electroluminescence element, a wavelength conversion substrate including the color conversion layer of the present invention, and the like.

Here, the color conversion layer in the wavelength conversion substrate of the present invention is preferably arranged in parallel with the light-emitting surface of the self-luminous light source, and the distance between the surface of the color conversion layer on the self-luminous light source side and the light-emitting surface of the self-luminous light source It is less than 10 μm. If the distance from the light-emitting surface is 10 μm or less, the pyrromethene derivative contained in the color conversion layer easily absorbs the blue light emitted by the light source, and the scattering effect of inorganic particles is also increased, so the pyrrole can be maximized Color conversion efficiency of methyl derivatives. The distance between the color conversion layer of the present invention and the light-emitting surface of the light source is more preferably 5 μm or less. Furthermore, it is preferable that the color conversion layer is in close contact with the light emitting surface of the light source. [Example]

Hereinafter, specific examples are used to illustrate the present invention and its effects, but the examples do not limit the scope of application of the present invention.

＜Inorganic particles＞ R1: Alumina particles "AKP-3000" (manufactured by Sumitomo Chemical Co., Ltd., average particle size 0.5 μm, refractive index 1.76) R2: Zirconia particles "UEP-100" (manufactured by Daiichi Rare Element Chemical Industry Co., Ltd., average particle diameter 0.6 μm, refractive index 2.4) R3: Titanium dioxide particles "JR-301" (manufactured by Tayca Co., Ltd., average particle size 0.3 μm, refractive index 2.7) R4: Titanium dioxide particles "JA-1" (manufactured by Tayca (stock), average particle size 0.18 μm, refractive index 2.5) R5: Magnesium oxide particles "SMO-0.4" (manufactured by Sakai Chemical Industry Co., Ltd., average particle size 0.4 μm, refractive index 1.72) R6: Zinc oxide particles "FINEX (FINEX)-30W-LP2" (manufactured by Sakai Chemical Industry Co., Ltd., average particle size 0.35 μm, refractive index 1.95) R7: Silicon dioxide particles "SO-E2" (manufactured by Admatechs (stock), average particle size 0.5 μm, refractive index 1.45) R8: Barium sulfate particles "B-30" (manufactured by Sakai Chemical Industry Co., Ltd., average particle size 0.3 μm, refractive index 1.64) R9: Titanium dioxide particles "JR-1000" (manufactured by Tayca (stock), average particle diameter 1.0 μm, refractive index 2.7) R10: Titanium dioxide particles "JR-405" (manufactured by Tayca Co., Ltd., average particle size 0.21 μm, refractive index 2.7)

<Luminescent agent> RD-1, GD-1 to 4, DCJTB, and G-303 are the compounds shown below. [化31]

[化32]

<Viscosity measurement> For the color conversion composition produced in the Examples and Comparative Examples described later, the viscosity measurement was performed under the following conditions. Measuring device: B-type viscometer model (Model) RVDVII+ (manufactured by BROOKFIELD) Measuring temperature: 25℃ Speed: 50 rpm Timing of measurement: 1 minute after the start of rotor stirring

<Evaluation of color conversion efficiency> The display produced in the following Examples and Comparative Examples was driven at 100 mA/cm ² for red and green, and the peak intensity of each color was measured with a spectroradiometer SR-LEDW manufactured by Topcon . For red, measure the peak intensity at a wavelength of 600 nm to 700 nm, and for green, measure the peak intensity at a wavelength of 500 nm to 550 nm. The peak intensity of Comparative Example 1 is set to 1.0, and the relative value of the peak intensity is shown. The larger the relative value, the better the color conversion efficiency. A: The relative value value is 4.0 or more, and the color conversion efficiency is very effective. B: The relative value value is 2.0 or more and less than 4.0. The color conversion efficiency is greatly improved. C: The relative value value is 1.3 or more and less than 2.0. There is an effect of improving color conversion efficiency D: The relative value is less than 1.3 There is no effect of improving color conversion efficiency.

＜Durability evaluation＞ The chromaticity change of the displays produced in the following Examples and Comparative Examples at all lighting (white) was measured, and the time from the initial value of CIEu'v' to the change of ±0.01 was used for durability evaluation. The longer the time to change, the better the durability. A: More than 400 hours, extremely durable B: 200 hours or more but less than 400 hours, good durability C: More than 100 hours and less than 200 hours, there is no problem in durability in actual use D: Less than 100 hours, poor durability.

＜Measurement of film thickness＞ After using a needle to scratch part of the color conversion layer to expose the glass coated with the color conversion composition, a stylus-type film thickness meter (SURFCOM (SURFCOM) 1400d, Tokyo Precision Co., Ltd. ) Manufacturing) The height of the surface of the color conversion layer and the glass substrate is measured as the film thickness.

＜Evaluation of film thickness uniformity＞ After using a needle to scratch any part of the produced 5 cm×5 cm color conversion layer to expose the glass coated with the color conversion composition, a stylus-type film thickness meter (Suochem SURFCOM) 1400d, manufactured by Tokyo Precision Co., Ltd.) The height of the surface of the color conversion layer and the glass substrate was measured as the film thickness. Measure 10 points from the part scratched by the needle at 2 mm intervals, and find the maximum, minimum, and average film thickness of each color conversion layer (additional average of the 10-point measurement results). The film thickness deviation B is obtained by the following formula. Film thickness deviation B (%)={|(Maximum film thickness deviation*-average film thickness)|/average film thickness}×100 *The maximum film thickness deviation value selects the largest difference between the maximum film thickness and the minimum film thickness and the average film thickness. |(Maximum film thickness deviation value*-average film thickness)| is an absolute value. A: The film thickness deviation B (%) is less than 3%, and the film thickness uniformity is good. B: The film thickness deviation B (%) is 3% or more and less than 5%. The film thickness uniformity is practically no problem C: Film thickness deviation B (%) is 5% or more. Film thickness uniformity is poor.

(Example 1) Hereinafter, a production example of the wavelength conversion substrate of the present invention and an LED display using the wavelength conversion substrate will be described. The LED display is formed with a pixel number of 160×120×RGB and a pixel pitch of 0.33 mm.

＜Production of wavelength conversion substrate＞ ·Making of separation wall Spin-coating VPA204/P5.4-2 (manufactured by Nippon Steel Chemical & Materials Co., Ltd.) on a transparent substrate (Corning 1737 glass: 50×50×1.1 mm) as a partition wall material, forming a grid pattern between them The mask is exposed to ultraviolet rays, developed with a 2% sodium carbonate aqueous solution, and then baked at 200°C to form a pattern of transparent partition walls (film thickness 25 μm). A line pattern with a line width of 0.1 mm, a pitch of 0.3 mm, and a film thickness of 20 μm was produced. ·Making of red transform layer Using a polyethylene container with a volume of 100 ml, add 37.5 g of butyl acetate, 0.04 g of the red pyrromethene derivative RD-1, 0.04 g of the green pyrromethene derivative GD-1, and polymethyl as the matrix resin. Methyl acrylate (PARAPET GHS; manufactured by Kuraray) 9.51 g and inorganic particles R1 2.91 g were mixed. Then, using a planetary stirring and degassing device, stirring and degassing at 1000 rpm for 40 minutes, to produce a red color conversion composition. The viscosity of the red conversion composition was measured and the result was 0.4 Pa·s. The produced red conversion composition was coated on the substrate using a nozzle coating method, heated at 120° C. for 40 minutes and dried to obtain a red conversion layer with an average film thickness of 15 μm. ·Making of green conversion layer (green) Using a polyethylene container with a volume of 100 ml, add 37.5 g of butyl acetate, 0.04 g of the green pyrromethene derivative GD-1, and polymethyl methacrylate (PARAPET) GHS as the matrix resin; 9.55 g of Kuraray (manufactured by Kuraray) and 2.91 g of inorganic particles R1 were mixed. Then, using a planetary stirring and defoaming device, stirring and defoaming at 1000 rpm for 40 minutes, to produce a green conversion composition. The viscosity of the green conversion composition was measured and the result was 0.4 Pa·s. The produced green conversion composition was coated on the substrate using a nozzle coating method, heated at 120° C. for 40 minutes and dried to obtain a green conversion layer with an average film thickness of 15 μm. In this way, the following wavelength conversion substrate was produced: a line pattern with a line width of 0.1 mm, a pitch of 0.3 mm, and a film thickness of 10 μm, and pixels that transmit blue light, pixels including a red conversion layer, and a green conversion layer Of pixels.

·The production of LED display Corresponding to the patterned pixel shape on the wavelength conversion substrate produced by the above, a micro-flip chip (Mini-Flip Chip) 0510 (micro LED; Kyrgyzstan) is mounted on the Thin Film Transistor (TFT) substrate. Nite (GeneLite)) to produce a self-luminous LED substrate that can be partially driven. The wavelength conversion substrate and the LED substrate were bonded so that the distance between the color conversion layer in the wavelength conversion substrate and the light-emitting surface of the LED in the LED substrate became 10 μm to produce an LED display. ·Evaluation results Table 2 shows the results of measuring the peak intensity of each color using this LED display. Red has a relative value of 3.0, and green has a relative value of 3.0, and good color conversion efficiency is obtained. In addition, the chromaticity change at the time of all lighting (white) was measured. As a result, the time from the initial value of CIEu'v' to the change of ±0.01 was 350 hours, and good durability was obtained.

(Example 2 to Example 5) (Types of inorganic particles) Except changing to the inorganic particles shown in Table 2 and Table 3, a wavelength conversion substrate was produced by the same operation as in Example 1, and then an LED display was produced, and each measurement and evaluation were performed. The results are shown in Table 2 and Table 3. As shown in Table 2 and Table 3, it can be seen from the evaluation results of Examples 2 to 5 that if it is the color conversion composition of the embodiment of the present invention, the color conversion efficiency and durability are good.

[Table 2] (Table 2)

[Table 3] (Table 3)

(Comparative example 1) (Types of inorganic particles) Except that the color conversion composition was produced by the following method, a wavelength conversion substrate was produced by the same operation as in Example 1, and then an LED display was produced, and each measurement and evaluation were performed. The results are shown in Table 3. As shown in Table 3, in Comparative Example 1, practically no problem can be obtained in durability. ·Making of red transform layer Using a polyethylene container with a volume of 100 ml, add 37.5 g of butyl acetate, 0.04 g of the red pyrromethene derivative RD-1, 0.04 g of the green pyrromethene derivative GD-1, and polymethyl as the matrix resin. 12.42 g of methyl acrylate (PARAPET GHS; manufactured by Kuraray) was mixed. Then, using a planetary stirring and degassing device, stirring and degassing at 1000 rpm for 40 minutes, to produce a red color conversion composition. The viscosity of the red conversion composition was measured and the result was 0.3 Pa·s. The produced red conversion composition was coated on the substrate using a nozzle coating method, heated at 120° C. for 40 minutes and dried to obtain a red conversion layer with an average film thickness of 15 μm. ·The production of green transformation layer Using a polyethylene container with a volume of 100 ml, add 37.5 g of butyl acetate, 0.04 g of the green pyrromethene derivative GD-1, and polymethyl methacrylate (PARAPET) GHS as the matrix resin; Kuraray (made by Kuraray) 12.46 g is mixed. Then, using a planetary stirring and defoaming device, stirring and defoaming at 1000 rpm for 40 minutes, to produce a green conversion composition. The viscosity of the green conversion composition was measured and the result was 0.3 Pa·s. The produced green conversion composition was coated on the substrate using a nozzle coating method, heated at 120° C. for 40 minutes and dried to obtain a green conversion layer with an average film thickness of 15 μm.

(Comparative example 2, Comparative example 3) (Types of inorganic particles) Except changing to the inorganic particles shown in Table 3, a wavelength conversion substrate was produced by the same operation as in Example 1, and then an LED display was produced, and each measurement and evaluation were performed. The results are shown in Table 3. As shown in Table 3, in Comparative Example 2 and Comparative Example 3, although there is no practical problem in durability, the color conversion efficiency is not improved.

(Example 6 to Example 9) (Content of inorganic particles) Except changing to the color conversion composition shown in Table 4, a wavelength conversion substrate was produced by the same operation as in Example 1, and then an LED display was produced, and each measurement and evaluation were performed. The results are shown in Table 4. As shown in Table 4, based on the evaluation results of Examples 6 to 9, it can be seen that the color conversion composition of the embodiment of the present invention has good color conversion efficiency and durability.

[Table 4] (Table 4)

(Example 10 to Example 13) (Type of luminescent agent) Except for changing to the luminescent agent shown in Table 5, a wavelength conversion substrate was produced by the same operation as in Example 1, and then an LED display was produced, and each measurement and evaluation were performed. The results are shown in Table 5. As shown in Table 5, it can be seen from the evaluation results of Examples 10 to 13 that the color conversion composition according to the embodiment of the present invention has very good color conversion efficiency and durability.

[Table 5] (Table 5)

(Comparative Example 4, Comparative Example 5) (Type of luminescent agent) Except for changing to the luminescent agent shown in Table 5, a wavelength conversion substrate was produced by the same operation as in Example 1, and then an LED display was produced, and each measurement and evaluation were performed. The results are shown in Table 5. As shown in Table 5, in Comparative Example 4 and Comparative Example 5, the color conversion efficiency was improved to some extent, but the durability was reduced.

(Example 14, Example 15) (Type of matrix resin) Except changing to the matrix resin shown in Table 6, the wavelength conversion substrate was produced by the same operation as in Example 1, and then an LED display was produced, and each measurement and evaluation were performed. The results are shown in Table 6. As shown in Table 6, the evaluation results of Example 14 and Example 15 show that the color conversion composition according to the embodiment of the present invention has good color conversion efficiency and durability.

[Table 6] (Table 6)

(Comparative Example 6) (Type of matrix resin) Except that the color conversion composition was produced by the following method, a wavelength conversion substrate was produced by the same operation as in Example 1, and then an LED display was produced, and each measurement and evaluation were performed. The results are shown in Table 6. As shown in Table 6, in Comparative Example 6, the color conversion efficiency was improved to some extent, but the durability was reduced. ·Making of red transform layer Using a polyethylene container with a volume of 100 ml, add 37.5 g of propylene glycol methyl ether acetate (PMA), 0.04 g of the red pyrromethene derivative RD-1, and GD of the green pyrromethene derivative. -1 0.04 g, KAYARAD DPHA (monomer; manufactured by Nippon Kayaku) 4.98 g, A0502 (photopolymerization initiator; manufactured by Tokyo Chemical Industry) 0.25 g, Z254F (acrylic oligomer; contest Mix 7.22 g of Lu hydrogen (manufactured by DAICEL ALLNEX) and 2.87 g of inorganic particles R1. Then, using a planetary stirring and degassing device, stirring and degassing at 1000 rpm for 40 minutes, to produce a red color conversion composition. The viscosity of the red conversion composition was measured, and the result was 0.1 Pa·s. The produced red conversion composition was coated on the substrate using a nozzle coating method, heated at 120° C. for 40 minutes and dried to obtain a red conversion layer with an average film thickness of 15 μm. ·The production of green transformation layer Using a polyethylene container with a volume of 100 ml, add 37.5 g butyl acetate, 0.04 g green pyrromethene derivative GD-1, KAYARAD DPHA (monomer; manufactured by Nippon Kayaku) 4.98 g, A0502 (photopolymerization initiator; manufactured by Tokyo Chemical Industry) 0.25 g, Z254F (acrylic oligomer; manufactured by DAICEL ALLNEX) 7.26 g, and 2.87 g of inorganic particles R1 were mixed. Then, using a planetary stirring and defoaming device, stirring and defoaming at 1000 rpm for 40 minutes, to produce a green conversion composition. The viscosity of the green conversion composition was measured, and the result was 0.1 Pa·s. The produced green conversion composition was coated on the substrate using a nozzle coating method, heated at 120° C. for 40 minutes and dried to obtain a green conversion layer with an average film thickness of 15 μm.

(Example 16, Example 17) (The distance between the cured film and the light-emitting surface) Except that the distance between the color conversion layer of the wavelength conversion substrate and the light-emitting surface of the LED substrate was changed to the value shown in Table 6, an LED display was produced by the same operation as in Example 1, and each measurement and evaluation were performed. The results are shown in Table 7. As shown in Table 7, the evaluation results of Example 15 and Example 16 show that if the distance between the surface of the color conversion layer on the side close to the light source and the light emitting surface is 10 μm or less, the color conversion efficiency and durability are good.

[Table 7] (Table 7)

(Embodiment 18) (Combination with color filter) Hereinafter, a production example of the wavelength conversion substrate of the present invention and an LED display using the wavelength conversion substrate will be described. The LED display is formed with a pixel number of 160×120×RGB and a pixel pitch of 0.3 mm. ＜Production of wavelength conversion substrate＞ ·Making of separation wall Spin-coating VPA204/P5.4-2 (manufactured by Nippon Steel Chemical & Materials Co., Ltd.) on a transparent substrate (Corning 1737 glass: 50×50×1.1 mm) as a partition wall material, forming a grid pattern between them The mask is exposed to ultraviolet rays, developed with a 2% sodium carbonate aqueous solution, and then baked at 200°C to form a pattern of transparent partition walls (film thickness 25 μm). A line pattern with a line width of 0.1 mm, a pitch of 0.3 mm, and a film thickness of 20 μm was produced. ·Production of color filter For the transparent substrate on which the partition wall is made, spin coating is used to coat the red color filter material (manufactured by Fujifilm Electronic Materials (Stock): color mosaic CR-7001). The formed coating film was patterned by photolithography. In this way, a red color filter having a line pattern with a line width of 0.1 mm, a pitch of 0.3 mm, and a film thickness of 2 μm was produced. Secondly, in addition to using the green color filter material (manufactured by Fujifilm Electronic Materials Co., Ltd.: color mosaic (color mosaic) CG-7001), the green color filter was produced using the same method as the red color filter. . The produced green color filter had a line pattern with a line width of 0.1 mm, a pitch of 0.3 mm, and a film thickness of 2 μm, similarly to the red color filter.

·Making of red transform layer Using a polyethylene container with a volume of 100 ml, add 37.5 g of butyl acetate, 0.04 g of the red pyrromethene derivative RD-1, 0.04 g of the green pyrromethene derivative GD-1, and polymethyl as the matrix resin. Methyl acrylate (PARAPET GHS; manufactured by Kuraray) 9.51 g and inorganic particles R1 2.91 g were mixed. Then, using a planetary stirring and degassing device, stirring and degassing at 1000 rpm for 40 minutes, to produce a red color conversion composition. The viscosity of the red conversion composition was measured and the result was 0.4 Pa·s. The produced red conversion composition was coated on the red color filter using a nozzle coating method, heated at 120° C. for 40 minutes and dried to obtain a color conversion layer with an average film thickness of 15 μm. ·The production of green transformation layer Using a polyethylene container with a volume of 100 ml, add 37.5 g of butyl acetate, 0.04 g of the green pyrromethene derivative GD-1, and polymethyl methacrylate (PARAPET) GHS as the matrix resin; 9.55 g of Kuraray (manufactured by Kuraray) and 2.91 g of inorganic particles R1 were mixed. Then, using a planetary stirring and defoaming device, stirring and defoaming at 1000 rpm for 40 minutes, to produce a green conversion composition. The viscosity of the green conversion composition was measured and the result was 0.4 Pa·s. The produced green conversion composition was coated on the green color filter using a nozzle coating method, heated at 120° C. for 40 minutes and dried to obtain a color conversion layer with an average film thickness of 15 μm. In this way, a color conversion substrate having pixels that transmit blue light, pixels having a red color filter on the red conversion layer, and pixels having a green color filter on the green conversion layer was produced.

·The production of LED display Corresponding to the patterned pixel shape on the wavelength conversion substrate produced by the above, a Mini-Flip Chip 0510 (micro LED; manufactured by GeneLite) is mounted on the TFT substrate. This produced a partially driven self-luminous LED substrate. The wavelength conversion substrate and the LED substrate were bonded so that the distance between the color conversion layer in the wavelength conversion substrate and the light-emitting surface of the LED in the LED substrate became 10 μm to produce an LED display. ·Evaluation results Table 8 shows the results of measuring the peak intensity of each color using this LED display. Red is a relative value of 4.6, and green is a relative value of 4.6, and good color conversion efficiency is obtained. In addition, the chromaticity change at the time of all lighting (white) was measured. As a result, the time from the initial value of CIEu'v' to the change of ±0.01 was 350 hours, and good durability was obtained.

[Table 8] (Table 8)

(Example 19 to Example 44) (Type and content of inorganic particles) In addition to changing the matrix resin to the acrylic copolymer resin (coponyl N-6593; manufactured by Mitsubishi Chemical Co., Ltd.) shown in Table 9 to Table 15 and the type and blending amount of inorganic particles, the blending amount of luminescent material and matrix resin Except for changing to the composition described in the table, a wavelength conversion substrate was produced by the same operation as in Example 1, and then an LED display was produced, and each measurement and evaluation were performed. The results are shown in Table 9-15. As shown in Tables 9 to 15, the evaluation results of Examples 19 to 44 show that the color conversion composition according to the embodiment of the present invention has good color conversion efficiency and durability.

[Table 9] (Table 9)

[Table 10] (Table 10)

[Table 11] (Table 11)

[Table 12] (Table 12)

[Table 13] (Table 13)

[Table 14] (Table 14)

[Table 15] (Table 15)

(Example 45 to Example 49) (Effect of viscosity) Except for adjusting the amount of the solvent to be blended and changing to the color conversion composition having the viscosity shown in Table 16, the wavelength conversion substrate was produced by the same operation as in Example 1, and then an LED display was produced, and each measurement and evaluation were performed. The results are shown in Table 16. As shown in Table 16, from the evaluation results of Examples 45 to 49, it can be seen that the color conversion composition according to the embodiment of the present invention has good color conversion efficiency and durability.

[Table 16] (Table 16)

(Example 50, Example 51) (Coating method) Except having changed to the coating method shown in Table 17, the LED display was produced by the same operation as Example 1, and each measurement and evaluation were performed. The results are shown in Table 17. As shown in Table 17, from the evaluation results of Example 50 and Example 51, it can be seen that the coating method of the present invention has good color conversion efficiency and durability, and also good film thickness uniformity.

[Table 17] (Table 17)

(Example 52 to Example 55) (Type of luminescent agent) The matrix resin was changed to the acrylic copolymer resin shown in Table 18 (coponyl N-6593; manufactured by Mitsubishi Chemical), and the addition amount of the luminescent agent, inorganic particles, and inorganic particles shown in Table 18 was changed to use The color conversion composition was produced in the same manner as in Example 1. Then, a wavelength conversion substrate was produced by the same operation as in Example 1, and an LED display was produced, and each measurement and evaluation were performed. The results are shown in Table 18. As shown in Table 18, from the evaluation results of Examples 52 to 55, it can be seen that the color conversion composition according to the embodiment of the present invention has very good color conversion efficiency and durability.

[Table 18] (Table 18)

(Comparative Example 7, Comparative Example 8) (Type of luminescent agent) The matrix resin was changed to the acrylic copolymer resin shown in Table 18 (coponyl N-6593; manufactured by Mitsubishi Chemical), and the addition amount of the luminescent agent, inorganic particles, and inorganic particles shown in Table 18 was changed to use The color conversion composition was produced in the same manner as in Example 1. Then, a wavelength conversion substrate was produced by the same operation as in Example 1, and an LED display was produced, and each measurement and evaluation were performed. The results are shown in Table 18. As shown in Table 18, in Comparative Example 7 and Comparative Example 8, the color conversion efficiency and durability were reduced.

[表20] （表20）

(Example 56 to Example 63) (Type of luminescent agent, content of titanium dioxide) The matrix resin was changed to the acrylic copolymer resin shown in Table 19 and Table 20 (coponyl N-6593; manufactured by Mitsubishi Chemical) The addition amount of the luminescent agent, inorganic particles, and inorganic particles shown in Table 19 and Table 20 was changed, and the color conversion composition was produced by the same operation as in Example 1. Then, a wavelength conversion substrate was produced by the same operation as in Example 1, and an LED display was produced, and each measurement and evaluation were performed. The results are shown in Table 19 and Table 20. As shown in Table 19 and Table 20, the evaluation results of Examples 56 to 63 show that the color conversion composition according to the embodiment of the present invention has good color conversion efficiency and durability. [Table 19] (Table 19)

[Table 20] (Table 20)

1: Transparent substrate 2: separation wall 3: Red transformation layer 4: Green transformation layer 5: Micro LED 6: substrate 7: Organic EL element 8: Sealing layer 9: Red color filter 10: Green color filter 11: Wavelength conversion substrate 12: LED substrate 13: Organic EL substrate 14: Blue color filter 20: Display using wavelength conversion substrate (micro LED) 21: Displays using wavelength conversion substrates (organic EL elements)

Fig. 1 is a schematic cross-sectional view showing an example of a wavelength conversion substrate using a color conversion composition according to an embodiment of the present invention. Fig. 2 is an example of a display using the color conversion composition of the embodiment of the present invention. Fig. 3 is an example of a display using the color conversion composition of the embodiment of the present invention. 4 is a schematic cross-sectional view showing an example of a wavelength conversion substrate using the color conversion composition of the embodiment of the present invention. Fig. 5 is an example of a display using the color conversion composition of the embodiment of the present invention. Fig. 6 is an example of a display using the color conversion composition of the embodiment of the present invention. Fig. 7 is a schematic cross-sectional view showing an example of a wavelength conversion substrate using the color conversion composition of the embodiment of the present invention. Fig. 8 is an example of a display using the color conversion composition of the embodiment of the present invention. Fig. 9 is an example of a display using the color conversion composition of the embodiment of the present invention.

Claims (26)

A color conversion composition characterized by containing a pyrromethene derivative, a matrix resin, and inorganic particles having a refractive index of 1.7 to 2.8, and containing no photosensitive component. The color conversion composition described in item 1 of the scope of patent application does not contain heat-sensitive components. The color conversion composition according to the first item of the scope of patent application, wherein the content of the inorganic particles is 3% by mass or more and 70% by mass or less. The color conversion composition according to the first item of the scope of patent application, wherein the content of the inorganic particles is 3% by mass or more and 20% by mass or less. The color conversion composition according to the first item of the scope of patent application, wherein the average particle diameter of the inorganic particles is 0.1 μm or more and 0.7 μm or less. The color conversion composition according to item 1 of the scope of patent application, wherein the inorganic particles contain at least one selected from the group consisting of alumina, zirconia, and titania. The color conversion composition described in item 1 of the scope of patent application, wherein the pyrromethene derivative is a compound represented by the general formula (1),

X is CR ⁷ or N, R ¹ to R ⁹ may be the same or different, and are selected from hydrogen, alkyl, cycloalkyl, heterocyclyl, alkenyl, cycloalkenyl, alkynyl, hydroxyl, thiol , Alkoxy, alkylthio, aryl ether, aryl sulfide, aryl, heteroaryl, halogen, cyano, aldehyde, carbonyl, carboxyl, ester, aminomethyl, amine, Among the nitro group, silyl group, siloxy group, oxyboron group, sulfo group, and phosphine oxide group, the selected group and the adjacent substituent may also form a condensed ring and an aliphatic ring. The color conversion composition described in item 7 of the scope of patent application, wherein in the general formula (1), X is CR ⁷ , and R ⁷ is the group represented by the general formula (2),

r is selected from hydrogen, alkyl, cycloalkyl, heterocyclyl, alkenyl, cycloalkenyl, alkynyl, hydroxyl, thiol, alkoxy, alkylthio, aryl ether, aryl sulfide , Aryl, heteroaryl, halogen, cyano, aldehyde, carbonyl, carboxyl, ester, carboxamide, amine, nitro, silyl, siloxyalkyl, oxyboron, sulfo, oxide In the group consisting of phosphine groups; k is an integer of 1 to 3; when k is 2 or more, r may be the same or different. The color conversion composition according to item 7 of the scope of patent application, wherein in the general formula (1), R ¹ , R ³ , R ⁴ and R ⁶ may be the same or different, and are substituted or unsubstituted Substituted alkyl. The color conversion composition according to item 7 of the scope of patent application, wherein in the general formula (1), R ¹ , R ³ , R ⁴ and R ⁶ may be the same or different, and are substituted or unsubstituted Substituted aryl. The color conversion composition according to item 7 of the scope of patent application, wherein in the general formula (1), at least one of R ¹ to R ⁶ is an electron withdrawing group. The color conversion composition according to item 11 of the scope of patent application, wherein in the general formula (1), the electron withdrawing group is a group containing a fluorine atom. The color conversion composition according to item 11 of the scope of patent application, wherein in the general formula (1), the electron withdrawing groups are each independently selected from a fluorine-containing carbonyl group, a fluorine-containing ester group, and a fluorine-containing amine group , Fluorine-containing sulfonyl groups, fluorine-containing sulfonate groups and fluorine-containing sulfonamide groups. The color conversion composition according to item 7 of the scope of patent application, wherein in the general formula (1), at least one of R ⁸ or R ⁹ is a cyano group. The color conversion composition according to any one of items 1 to 14 in the scope of the patent application, wherein the pyrromethene derivative comprises the following pyrromethene derivative: displayed in 500 by using excitation light The peak wavelength of light emission is observed in the region above nm and below 580 nm. The color conversion composition according to any one of items 1 to 14 in the scope of patent application, wherein the pyrromethene derivative comprises the following pyrromethene derivative: displayed in 580 by using excitation light Luminescence of the peak wavelength is observed in the region from nm to 750 nm. The color conversion composition according to any one of items 1 to 14 of the scope of patent application, wherein the color conversion composition contains the following first luminescent material and second luminescent material, the first luminescent material or the second luminescent material At least one of the luminescent materials is the pyrromethene derivative, (A) The first luminescent material, by using excitation light, emits light with a peak wavelength observed in the region above 500 nm and less than 580 nm (B) The second luminescent material is excited by at least one of the excitation light or the luminescence from the first luminescent material to exhibit luminescence with a peak wavelength observed in a region above 580 nm and below 750 nm. The color conversion composition described in any one of items 1 to 14 of the scope of patent application contains a solvent and has a viscosity of 0.2 Pa·s or more and 50 Pa·s or less. A color conversion layer includes the color conversion composition as described in any one of items 1 to 18 in the scope of patent application. A wavelength conversion substrate includes the color conversion layer as described in item 19 of the scope of patent application. The wavelength conversion substrate described in item 20 of the scope of patent application further includes a color filter. A method for manufacturing a wavelength conversion substrate includes a step of patterning a color conversion layer by coating the color conversion composition as described in any one of items 1 to 18 in the scope of the patent application through a nozzle. A method for manufacturing a wavelength conversion substrate includes a step of patterning a color conversion layer by coating the color conversion composition according to any one of items 1 to 18 in the scope of the patent application by a slit die. A display that uses the wavelength conversion substrate described in item 20 or item 21 of the scope of patent application and a partially driven self-luminous light source that emits blue light or blue-green light in pixels. The display according to item 24 of the scope of patent application, wherein the color conversion layer in the wavelength conversion substrate is arranged parallel to the light emitting surface of the self-luminous light source, and the distance between the color conversion layer and the light emitting surface is 10 μm the following. The display according to item 24 or item 25 of the scope of patent application, wherein the self-luminous light source is a micro light-emitting diode or an organic electroluminescence element.

Images