Color conversion material, color conversion film, three-dimensional structure including the same, light source unit, display, and illumination device

Abstract

To provide a color conversion film for use in displays and illumination devices, which offers both improved color reproducibility and durability, in particular, light emission with high color purity and durability.SOLUTION: A compound represented by the general formula (1) below is provided.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a color conversion material, a color conversion film, and a three-dimensional structure, a light source unit, a display and a lighting device each including the same. [Background technology]

[0002] There is active research into applying multi-color technology using color conversion methods to liquid crystal displays, organic EL displays, lighting devices, etc. Color conversion refers to converting light emitted from an illuminant into light with a longer wavelength, such as converting blue light into green or red light.

[0003] By forming this composition with color conversion functionality into a sheet and combining it with, for example, a blue light source, it is possible to obtain the three primary colors of blue, green, and red from the blue light source, i.e., white light. By using a white light source that combines such a blue light source with a sheet with color conversion functionality as a light source unit such as a backlight unit, and combining this light source unit with a liquid crystal driver and a color filter, it is possible to produce a full-color display. Furthermore, a white light source that combines a blue light source with a sheet with color conversion functionality can also be used directly as a white light source for LED lighting, etc.

[0004] Issues facing displays that utilize color conversion technology include improving color reproducibility and durability. To improve color reproducibility, it is effective to narrow the half-width of the blue, green, and red emission spectra of the light source unit and increase the color purity of each color. To address this issue, color conversion materials containing organic fluorescent materials have been proposed (see, for example, Patent Documents 1 and 2). Furthermore, proposed technologies for improving durability include adding a light stabilizer (see, for example, Patent Document 3), improving durability by using an oxygen barrier (see, for example, Patent Document 4), molding a composition containing a matrix resin and a light-emitting material into particles and dispersing it in a support (see, for example, Patent Document 5), and incorporating an organic light-emitting material into a silica matrix to form nanoparticles (see, for example, Patent Document 6). [Prior art documents] [Patent documents]

[0005] [Patent Document 1] Japanese Patent Application Laid-Open No. 2010-61824 [Patent Document 2] Japanese Patent Application Laid-Open No. 2014-136771 [Patent Document 3] Japanese Patent Application Publication No. 2019-50381 [Patent Document 4] International Publication No. 2017 / 057287 [Patent Document 5] International Publication No. 2020 / 050144 [Patent Document 6] Japanese Patent Application Publication No. 2019-525379 Summary of the Invention [Problem to be solved by the invention]

[0006] Color-converting compositions with excellent color reproducibility and relatively excellent durability can be obtained by the techniques described in Patent Documents 1 to 6. However, in recent years, with the trend toward higher definition such as 4K and 8K, high dynamic range (HDR), and higher contrast due to local dimming, the illuminance required for display light source units has increased, and higher durability has also been required for color-converting films.

[0007] The problem that the present invention aims to solve is to achieve both improved color reproducibility and durability in color conversion films used in displays and lighting devices, and in particular, the object is to provide a color conversion film that achieves both high color purity light emission and durability. [Means for solving the problem]

[0008] In order to solve the above problems and achieve the object, the present invention has the following configuration. [1] A compound represented by the following general formula (1):

[0009] [ka]

[0010] (R 1 ~R 6 and R 11 ~R 15 each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted alkynyl group, a hydroxyl group, a thiol group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted aryl ether group, a substituted or unsubstituted aryl thioether group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a halogen atom, a cyano group, an aldehyde group, a substituted or unsubstituted carbonyl group, a carboxyl group, a methyl ... and n is 0 or 1. The substituent is selected from the group consisting of a carboxyl group, a substituted or unsubstituted oxycarbonyl group, a substituted or unsubstituted carbamoyl group, a substituted or unsubstituted ester group, a substituted or unsubstituted amido group, a substituted or unsubstituted acyl group, a substituted or unsubstituted sulfonyl group, a substituted or unsubstituted sulfonate ester group, a substituted or unsubstituted sulfonamido group, an amino group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkoxysilyl group, a substituted or unsubstituted silanol group, a substituted or unsubstituted siloxanyl group, a substituted or unsubstituted boryl group, and a substituted or unsubstituted phosphine oxide group.

[0011] R 7 and R 8are each independently selected from the group consisting of a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted alkynyl group, a hydroxyl group, a thiol group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted aryl ether group, a substituted or unsubstituted aryl thioether group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a halogen atom, and a cyano group.

[0012] However, R 1 ~R 8 and R 11 ~R 15 At least one of them contains a structure represented by the following general formula (2).

[0013] [ka]

[0014] L 1 is a single bond, an oxygen atom, a sulfur atom, a carbonyl group, -C(=O)O-, -OC(=O)-, or -SiR c R d -It is.

[0015] L 2 is a substituted or unsubstituted alkylene group, a substituted or unsubstituted alkyleneoxy group, a substituted or unsubstituted alkylenethio group, a substituted or unsubstituted cycloalkylene group, a substituted or unsubstituted arylene group, a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted heteroarylene group.

[0016] R a is a hydrogen atom or a linear or branched alkyl group, and R b is a hydrogen atom, a halogen, a linear or branched alkyl group, a substituted or unsubstituted cycloalkyl group, or a substituted or unsubstituted aryl group.

[0017] R c and R d are each independently selected from the group consisting of a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkoxysilyl group, and a silanol group, and n is an integer of 1 to 3.

[0018] However, the compound represented by general formula (1) satisfies either the following (A) or (B): (A)R 11 ~R 15 At least one of the groups is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. (B)R 2 and R 5 is a hydrogen atom.) [2] The compound represented by general formula (1) satisfies (A), and R 11 ~R 15 At least two of the groups are substituted or unsubstituted aryl groups or substituted or unsubstituted heteroaryl groups. [3] The compound according to [1] or [2], wherein the compound represented by general formula (1) satisfies (A) and is a compound represented by general formula (3) or (4).

[0019] [ka]

[0020] (In general formula (3) or (4), R 1 ~R 8 and R 11 ~R 15 The definition of R is the same as in general formula (1). 21 ~R 40each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted alkynyl group, a hydroxyl group, a thiol group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted aryl ether group, a substituted or unsubstituted aryl thioether group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a halogen atom, a cyano group, an aldehyde group, a substituted or unsubstituted carbonyl group, a carboxyl group, a methyl ... and n is 0 or 1. The substituent is selected from the group consisting of a carboxyl group, a substituted or unsubstituted oxycarbonyl group, a substituted or unsubstituted carbamoyl group, a substituted or unsubstituted ester group, a substituted or unsubstituted amido group, a substituted or unsubstituted acyl group, a substituted or unsubstituted sulfonyl group, a substituted or unsubstituted sulfonate ester group, a substituted or unsubstituted sulfonamido group, an amino group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkoxysilyl group, a substituted or unsubstituted silanol group, a substituted or unsubstituted siloxanyl group, a substituted or unsubstituted boryl group, and a substituted or unsubstituted phosphine oxide group. However, in the general formula (3), R 11 , R 13 , R 15 and R 21 ~R 30 At least one of the formulas (2) contains a structure represented by general formula (4), and in general formula (4), R 12 ~R 14 and R 31 ~R 40 At least one of the above contains a structure represented by general formula (2). [4] In the general formula (3), R 11 , R 13 , R 15 and R 21 ~R 30 At least two of the general formula (4) contain a structure represented by general formula (2), and in general formula (4), R 12 ~R 14 and R 31 ~R 40The compound according to [3], wherein at least two of the above formulas contain a structure represented by general formula (2). [5] The compound according to [3] or [4], wherein the compound represented by general formula (3) is a compound represented by general formula (5), and the compound represented by general formula (4) is a compound represented by general formula (6).

[0021] [ka]

[0022] (L in general formula (5) or general formula (6) 1 , L 2 , R 1 ~R 8 , R 11 ~R 15 , R 21 ~R 40 , R a , R b and n is defined as in general formula (2), general formula (3), or general formula (4). [6] In the general formula (5) or (6), R 2 and R 5 are each independently selected from the group consisting of a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a halogen atom, and a substituted or unsubstituted silyl group. [7] In the general formula (5) or (6), R 2 and R 5 The compound according to [5] or [6], wherein [8] The compound represented by general formula (1) satisfies (B), and R 11 ~R 15 At least one of the groups is a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, or a halogen. [9] The compound represented by the general formula (1) satisfies (B), and R11 ~R 15 At least one of the groups is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group.

[10] The compound represented by general formula (1) satisfies (B), and R 11 ~R 15 The compound according to any one of [1], [8], and [9], wherein at least two of the groups are substituted or unsubstituted aryl groups or substituted or unsubstituted heteroaryl groups.

[11] The compound represented by the general formula (1) satisfies (B), and R 11 and R 15 , or R 12 and R 14 is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group.

[12] In the partial structure represented by general formula (2), L 1 is a single bond, an oxygen atom, a carbonyl group, -C(=O)O-, -OC(=O)-, or -SiR c R d - is selected from a candidate set consisting of L 2 The compound according to any one of [1] to

[11] , wherein represents a substituted or unsubstituted alkylene group or a substituted or unsubstituted alkyleneoxy group, and n is 2 or 3.

[13] The compound represented by the general formula (1) is the compound according to any one of [1] to

[12] , which exhibits luminescence with a peak wavelength observed in the region of 500 nm or more and 580 nm or less when excited with excitation light.

[14] A color-converting composition that converts incident light into light with a longer wavelength than the incident light, the color-converting composition comprising the compound according to any one of [1] to

[13] and a binder resin.

[15] A three-dimensional structure formed by a covalent bond between an element M and an oxygen atom, wherein the element M is an element selected from the group consisting of Si, Ti, and Al, and characterized in that it contains a partial structure represented by general formula (7).

[0023] [ka]

[0024] (In general formula (7), · represents a bonding point with the three-dimensional structure.

[0025] R 101 ~R 106 and R 111 ~R 115 are each independently, L 3 or a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted alkynyl group, a hydroxyl group, a thiol group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted aryl ether group, a substituted or unsubstituted aryl thioether group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a halogen atom, a cyano group, an aldehyde group, a substituted or unsubstituted carbonyl group, It is selected from the group consisting of a carboxyl group, a substituted or unsubstituted oxycarbonyl group, a substituted or unsubstituted carbamoyl group, a substituted or unsubstituted ester group, a substituted or unsubstituted amide group, a substituted or unsubstituted acyl group, a substituted or unsubstituted sulfonyl group, a substituted or unsubstituted sulfonate ester group, a substituted or unsubstituted sulfonamide group, an amino group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkoxysilyl group, a substituted or unsubstituted silanol group, a substituted or unsubstituted siloxanyl group, a substituted or unsubstituted boryl group, and a substituted or unsubstituted phosphine oxide group.

[0026] R 107 and R 108 are each independently, L 3or is selected from the group consisting of a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted alkynyl group, a hydroxyl group, a thiol group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted aryl ether group, a substituted or unsubstituted aryl thioether group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a halogen, and a cyano group.

[0027] However, R 101 ~R 108 and R 111 ~R 115 At least one of the 3 or a single bond connecting to L 3 has a substituent that bonds to

[0028] L 3 is a single bond, an oxygen atom, a sulfur atom, a carbonyl group, -C(=O)O-, -OC(=O)-, or -SiR f R g -It is. L 4 is a substituted or unsubstituted alkylene group, a substituted or unsubstituted alkyleneoxy group, a substituted or unsubstituted alkylenethio group, a substituted or unsubstituted cycloalkylene group, a substituted or unsubstituted arylene group, a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted heteroarylene group.

[0029] However, R f and R g are each independently selected from the group consisting of a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkoxysilyl group, and a silanol group.

[0030] R eis selected from a hydrogen atom, a halogen atom, a linear or branched alkyl group, a substituted or unsubstituted cycloalkyl group, and a substituted or unsubstituted aryl group. m is an integer of 1 to 3.

[0031] However, the partial structure represented by general formula (7) satisfies either the following (C) or (D). (C)R 111 ~R 115 At least one of the groups is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. (D)R 102 and R 105 is a hydrogen atom.

[16] In the partial structure represented by general formula (7), L 3 is a single bond, an oxygen atom, a sulfur atom, a carbonyl group, -C(=O)O-, -OC(=O)-, or -SiR f R g - and L 4 is a substituted or unsubstituted alkylene group or a substituted or unsubstituted alkyleneoxy group, and m is 2 or 3.

[17] The three-dimensional structure according to

[15] or

[16] , wherein the partial structure represented by general formula (7) is a partial structure represented by general formula (8) or (9).

[0032] [ka]

[0033] [ka]

[0034] In the general formulae (8) and (9), the symbol represents a bonding point to the three-dimensional structure.

[0035] R 102 and R 105 is a hydrogen atom.

[0036] R101 , R 103 , R 104 , R 106 , R 111 ~R 115 and R 131 ~R 140 each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted alkynyl group, a hydroxyl group, a thiol group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted aryl ether group, a substituted or unsubstituted aryl thioether group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a halogen atom, a cyano group, an aldehyde group, a substituted or unsubstituted carbonyl group, a carboxyl group, a methyl ... and n is 0 or 1. The substituent is selected from the group consisting of a carboxyl group, a substituted or unsubstituted oxycarbonyl group, a substituted or unsubstituted carbamoyl group, a substituted or unsubstituted ester group, a substituted or unsubstituted amido group, a substituted or unsubstituted acyl group, a substituted or unsubstituted sulfonyl group, a substituted or unsubstituted sulfonate ester group, a substituted or unsubstituted sulfonamido group, an amino group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkoxysilyl group, a substituted or unsubstituted silanol group, a substituted or unsubstituted siloxanyl group, a substituted or unsubstituted boryl group, and a substituted or unsubstituted phosphine oxide group.

[0037] R 107 and R 108are each independently selected from the group consisting of a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted alkynyl group, a hydroxyl group, a thiol group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted aryl ether group, a substituted or unsubstituted aryl thioether group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a halogen atom, and a cyano group.

[18] The three-dimensional structure according to any one of

[15] to

[17] , wherein the element M is Si.

[19] The three-dimensional structure according to any one of

[15] to

[17] , wherein the element M is Ti.

[20] A color-converting composition that converts incident light into light with a longer wavelength than the incident light, the color-converting composition comprising the three-dimensional structure according to any one of

[15] to

[19] and a binder resin.

[21] The color-changing composition according to any one of

[15] to

[20] , wherein the three-dimensional structures are in the form of particles.

[22] A color converting film comprising a layer made of the color converting composition according to

[14] or

[20] or a cured product thereof.

[23] A light source unit comprising a light source and the color conversion film according to

[22] .

[24] The light source unit according to

[23] , wherein the light source is a light-emitting diode having a maximum emission wavelength in the range of 430 nm to 500 nm.

[25] A display comprising the color conversion film according to

[23] .

[26] A lighting device comprising the color conversion film according to

[23] . [Effects of the Invention]

[0038] The color conversion material of the present invention and the color conversion film using the same have both high color purity and durability, and therefore it is possible to achieve both color reproducibility and durability. [Brief explanation of the drawings]

[0039] [Figure 1] FIG. 1 is a schematic cross-sectional view showing an example of the color conversion film of the present invention. [Figure 2] FIG. 1 is a schematic cross-sectional view showing an example of the color conversion film of the present invention. [Figure 3] FIG. 1 is a schematic cross-sectional view showing an example of the color conversion film of the present invention. DETAILED DESCRIPTION OF THE INVENTION

[0040] The following describes in detail the embodiments of the present invention, but the present invention is not limited to the following embodiments and can be modified in various ways depending on the purpose and application. Furthermore, the matters cited as preferred examples in specific embodiments and embodiments can also be applied to other embodiments and embodiments.

[0041] <Compound> The compound according to the embodiment of the present invention is a compound having a structure represented by general formula (1).

[0042] [ka]

[0043] In general formula (1), R 1 ~R 6 and R 11 ~R 15each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted alkynyl group, a hydroxyl group, a thiol group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted aryl ether group, a substituted or unsubstituted aryl thioether group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a halogen atom, a cyano group, an aldehyde group, a substituted or unsubstituted carbonyl group, a carboxyl group, a methyl ... and n is 0 or 1. The substituent is selected from the group consisting of a carboxyl group, a substituted or unsubstituted oxycarbonyl group, a substituted or unsubstituted carbamoyl group, a substituted or unsubstituted ester group, a substituted or unsubstituted amido group, a substituted or unsubstituted acyl group, a substituted or unsubstituted sulfonyl group, a substituted or unsubstituted sulfonate ester group, a substituted or unsubstituted sulfonamido group, an amino group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkoxysilyl group, a substituted or unsubstituted silanol group, a substituted or unsubstituted siloxanyl group, a substituted or unsubstituted boryl group, and a substituted or unsubstituted phosphine oxide group.

[0044] R 7 and R 8 are each independently selected from the group consisting of a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted alkynyl group, a hydroxyl group, a thiol group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted aryl ether group, a substituted or unsubstituted aryl thioether group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a halogen atom, and a cyano group.

[0045] In the present invention, "equal to or greater than" means equal to or greater than the indicated numerical value. "equal to or less than" means equal to or less than the indicated numerical value. "greater than" means greater than the indicated numerical value. "less than" means less than the indicated numerical value.

[0046] In all of the above groups, hydrogen may be replaced with deuterium. The same applies to the compounds or partial structures thereof described below.

[0047] In the following description, for example, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms means an aryl group having 6 to 40 carbon atoms, including the number of carbon atoms contained in a substituent substituted on the aryl group. The same applies to other substituents that specify the number of carbon atoms.

[0048] The term "unsubstituted" in the context of "substituted or unsubstituted" means that a hydrogen atom or a deuterium atom has been substituted. The same applies to the term "substituted or unsubstituted" in the compounds or partial structures thereof described below.

[0049] In all of the above groups, examples of the substituent when substituted include an alkyl group, a cycloalkyl group, a heterocyclic group, an alkenyl group, a cycloalkenyl group, an alkynyl group, an aryl group, a heteroaryl group, a hydroxyl group, a thiol group, an alkoxy group, an alkylthio group, an aryl ether group, an aryl thioether group, a halogen atom, a cyano group, an aldehyde group, a carbonyl group, a carboxy group, an oxycarbonyl group, an ester group, a carbamoyl group, an amide group, a sulfonyl group, a sulfonate ester group, a sulfonamide group, an imino group, an amino group, a nitro group, a silyl group, an alkoxysilyl group, a silanol group, a siloxanyl group, a boryl group, or a phosphine oxide group. These substituents may be further substituted with the above-mentioned substituents.

[0050] The alkyl group refers to a saturated aliphatic hydrocarbon group such as a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, or a tert-butyl group, which may or may not have a substituent. When substituted, the additional substituent is not particularly limited, and examples thereof include an alkyl group, a halogen atom, an aryl group, and a heteroaryl group. This also applies to the following description. The number of carbon atoms in the alkyl group is not particularly limited, but is preferably 1 to 20, more preferably 1 to 8, in terms of availability and cost. As the alkyl group, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, or a tert-butyl group is preferred from the viewpoint of excellent thermal stability. A sterically bulky tert-butyl group is more preferred from the viewpoint of preventing concentration quenching and improving luminescence quantum yield. A methyl group is also preferably used from the viewpoint of ease of synthesis and availability of raw materials.

[0051] The cycloalkyl group refers to a saturated alicyclic hydrocarbon group, such as a cyclopropyl group, a cyclohexyl group, a norbornyl group, an adamantyl group, or the like, which may or may not have a substituent. The number of carbon atoms in the alkyl group is not particularly limited, but is preferably in the range of 3 to 20.

[0052] The heterocyclic group refers to an aliphatic ring having atoms other than carbon atoms in the ring, such as a pyran ring, a piperidine ring, or a cyclic amide, which may or may not have a substituent. The number of carbon atoms in the heterocyclic group is not particularly limited, but is preferably in the range of 2 to 20.

[0053] The alkenyl group refers to an unsaturated aliphatic hydrocarbon group containing a double bond, such as a vinyl group, an allyl group, or a butadienyl group, which may or may not have a substituent. The number of carbon atoms in the alkenyl group is not particularly limited, but is preferably in the range of 2 to 20.

[0054] The cycloalkenyl group refers to an unsaturated alicyclic hydrocarbon group containing a double bond, such as a cyclopentenyl group, a cyclopentadienyl group, or a cyclohexenyl group, which may or may not have a substituent. The number of carbon atoms in the cycloalkenyl group is not particularly limited, but is preferably in the range of 3 to 20.

[0055] The alkynyl group refers to an unsaturated aliphatic hydrocarbon group containing a triple bond, such as an ethynyl group, which may or may not have a substituent. The number of carbon atoms in the alkynyl group is not particularly limited, but is preferably in the range of 2 to 20.

[0056] The alkoxy group refers to a functional group in which an aliphatic hydrocarbon group is bonded via an ether bond, such as a methoxy group, an ethoxy group, or a propoxy group, and this aliphatic hydrocarbon group may or may not have a substituent. The number of carbon atoms in the alkoxy group is not particularly limited, but is preferably in the range of 1 to 20.

[0057] An alkylthio group is an alkoxy group in which the oxygen atom of the ether bond is replaced with a sulfur atom. The hydrocarbon group of the alkylthio group may or may not have a substituent. The number of carbon atoms in the alkylthio group is not particularly limited, but is preferably in the range of 1 to 20.

[0058] The aryl ether group refers to a functional group, such as a phenoxy group, to which an aromatic hydrocarbon group is bonded via an ether bond, and the aromatic hydrocarbon group may or may not have a substituent. The number of carbon atoms in the aryl ether group is not particularly limited, but is preferably in the range of 6 to 40.

[0059] An aryl thioether group is an aryl ether group in which the oxygen atom of the ether bond is substituted with a sulfur atom. The aromatic hydrocarbon group in the aryl thioether group may or may not have a substituent. The number of carbon atoms in the aryl thioether group is not particularly limited, but is preferably in the range of 6 to 40.

[0060] The aryl group refers to an aromatic hydrocarbon group such as a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthryl group, an anthracenyl group, a benzophenanthryl group, a benzanthracenyl group, a chrysenyl group, a pyrenyl group, a fluoranthenyl group, a triphenylenyl group, a benzofluoranthenyl group, a dibenzoanthracenyl group, a perylenyl group, or a helicenyl group. Among these, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a phenanthryl group, an anthracenyl group, a pyrenyl group, a fluoranthenyl group, or a triphenylenyl group is preferred. The aryl group may or may not have a substituent. The number of carbon atoms in the aryl group is not particularly limited, but is preferably in the range of 6 to 40, more preferably 6 to 30.

[0061] The aryl group is preferably a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a phenanthryl group, or an anthracenyl group, more preferably a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group, even more preferably a phenyl group, a biphenyl group, or a terphenyl group, and particularly preferably a phenyl group.

[0062] When each of the substituents is further substituted with an aryl group, the aryl group is preferably a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a phenanthryl group, or an anthracenyl group, more preferably a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group, and particularly preferably a phenyl group.

[0063] Examples of heteroaryl groups include pyridyl, furanyl, thienyl, quinolinyl, isoquinolinyl, pyrazinyl, pyrimidyl, pyridazinyl, triazinyl, naphthyridinyl, cinnolinyl, phthalazinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothienyl, indolyl, dibenzofuranyl, dibenzothienyl, carbazolyl, and benzocarbazolyl. It refers to a cyclic aromatic group having one or more atoms other than carbon in the ring, such as a carbolinyl group, an indolocarbazolyl group, a benzofurocarbazolyl group, a benzothienocarbazolyl group, a dihydroindenocarbazolyl group, a benzoquinolinyl group, an acridinyl group, a dibenzoacridinyl group, a benzimidazolyl group, an imidazopyridyl group, a benzoxazolyl group, a benzothiazolyl group, or a phenanthrolinyl group. Here, the naphthyridinyl group refers to a 1,5-naphthyridinyl group, a 1,6-naphthyridinyl group, a 1,7-naphthyridinyl group, a 1,8-naphthyridinyl group, a 2,6-naphthyridinyl group, or a 2,7-naphthyridinyl group. The heteroaryl group may or may not have a substituent. The number of carbon atoms in the heteroaryl group is not particularly limited, but is preferably in the range of 2 or more and 40 or less, and more preferably 2 or more and 30 or less.

[0064] As the heteroaryl group, a pyridyl group, a furanyl group, a thienyl group, a quinolinyl group, a pyrimidyl group, a triazinyl group, a benzofuranyl group, a benzothienyl group, an indolyl group, a dibenzofuranyl group, a dibenzothienyl group, a carbazolyl group, a benzimidazolyl group, an imidazopyridyl group, a benzoxazolyl group, a benzothiazolyl group, or a phenanthrolinyl group is preferred, and a pyridyl group, a furanyl group, a thienyl group, or a quinolinyl group is more preferred, and a pyridyl group is particularly preferred.

[0065] When each substituent is further substituted with a heteroaryl group, the heteroaryl group is preferably a pyridyl group, a furanyl group, a thienyl group, a quinolinyl group, a pyrimidyl group, a triazinyl group, a benzofuranyl group, a benzothienyl group, an indolyl group, a dibenzofuranyl group, a dibenzothienyl group, a carbazolyl group, a benzimidazolyl group, an imidazopyridyl group, a benzoxazolyl group, a benzothiazolyl group, or a phenanthrolinyl group, more preferably a pyridyl group, a furanyl group, a thienyl group, or a quinolinyl group, and particularly preferably a pyridyl group.

[0066] Halogen refers to an atom selected from fluorine, chlorine, bromine and iodine.

[0067] The carbonyl group, carboxyl group, oxycarbonyl group, and carbamoyl group may or may not have a substituent. Examples of the substituent include an alkyl group, a cycloalkyl group, an aryl group, and a heteroaryl group, and these substituents may be further substituted.

[0068] The ester group refers to a functional group in which, for example, an alkyl group, a cycloalkyl group, an aryl group, a heteroaryl group, or the like is bonded via an ester bond, and this substituent may be further substituted. The number of carbon atoms in the ester group is not particularly limited, but is preferably in the range of 1 to 20. More specific examples of the ester group include methyl ester groups such as a methoxycarbonyl group, ethyl ester groups such as an ethoxycarbonyl group, propyl ester groups such as a propoxycarbonyl group, butyl ester groups such as a butoxycarbonyl group, isopropyl ester groups such as an isopropoxymethoxycarbonyl group, hexyl ester groups such as a hexyloxycarbonyl group, and phenyl ester groups such as a phenoxycarbonyl group.

[0069] The amide group refers to a functional group in which a substituent such as an alkyl group, a cycloalkyl group, an aryl group, or a heteroaryl group is bonded via an amide bond, and this substituent may be further substituted. The number of carbon atoms in the amide group is not particularly limited, but is preferably in the range of 1 to 20. More specific examples of the amide group include a methylamide group, an ethylamide group, a propylamide group, a butylamide group, an isopropylamide group, a hexylamide group, and a phenylamide group.

[0070] The acyl group refers to a functional group in which a substituent such as an alkyl group, a cycloalkyl group, an aryl group, or a heteroaryl group is bonded via a carbonyl bond, and this substituent may be further substituted. The number of carbon atoms in the acyl group is not particularly limited, but is preferably in the range of 1 to 20. More specifically, examples of the acyl group include an acetyl group, a propionyl group, a benzoyl group, and an acrylyl group.

[0071] The sulfonyl group, sulfonate group, and sulfonamide group are each represented by -S(=O)R 201 , -S(=O)2OR 201 , -S(=O)2NR 201 R 202 is a group represented by R 201 , R 202 is hydrogen or selected from the same group as the substituents when substituted as described above.

[0072] The amino group is a substituted or unsubstituted amino group. In the case of substitution, examples of the substituent include an aryl group, a heteroaryl group, a linear alkyl group, and a branched alkyl group. Preferred aryl and heteroaryl groups are a phenyl group, a naphthyl group, a pyridyl group, and a quinolinyl group. These substituents may be further substituted. The number of carbon atoms is not particularly limited, but is preferably in the range of 2 to 50, more preferably 6 to 40, and particularly preferably 6 to 30.

[0073] The silyl group refers to, for example, alkylsilyl groups such as trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, propyldimethylsilyl, and vinyldimethylsilyl, and arylsilyl groups such as phenyldimethylsilyl, tert-butyldiphenylsilyl, triphenylsilyl, and trinaphthylsilyl. The substituent on the silicon atom may be further substituted. The number of carbon atoms in the silyl group is not particularly limited, but is preferably in the range of 1 to 30.

[0074] Examples of the alkoxysilyl group include a trimethoxysilyl group, a triethoxysilyl group, a tripropoxysilyl group, a triisopropoxysilyl group, a tributoxysilyl group, a methoxydimethylsilyl group, an ethoxydimethylsilyl group, an isopropoxydimethylsilyl group, and an ethoxydiethylsilyl group. Of these, a trimethoxysilyl group, a triethoxysilyl group, a triisopropoxysilyl group, a methoxydimethylsilyl group, an ethoxydimethylsilyl group, and an isopropoxydimethylsilyl group are preferred.

[0075] The silanol group refers to a silicon compound group substituted with a hydroxyl group, such as a dimethylsilanol group or a diphenylsilanol group. The substituent on the silicon may be further substituted.

[0076] The siloxanyl group refers to a silicon compound group bonded via an ether bond, such as a trimethylsiloxanyl group, etc. The substituent on the silicon may be further substituted.

[0077] The boryl group is a substituted or unsubstituted boryl group. When substituted, examples of the substituent include an aryl group, a heteroaryl group, a linear alkyl group, a branched alkyl group, an aryl ether group, an alkoxy group, and a hydroxyl group, and among these, an aryl group and an aryl ether group are preferred.

[0078] The phosphine oxide group is -P(=O)R 201 R 202 R 201 and R 202is a hydrogen atom or is selected from the same group as the substituents when substituted as described above.

[0079] Any two adjacent substituents may be bonded to each other to form a conjugated or non-conjugated fused ring. The fused ring may contain, in addition to carbon, an element selected from nitrogen, oxygen, sulfur, phosphorus, and silicon. The fused ring may further be fused with another ring.

[0080] The compound represented by general formula (1) has a pyrromethene boron complex skeleton. The pyrromethene boron complex skeleton is a strong and highly planar skeleton. Therefore, the compound having the pyrromethene boron complex skeleton exhibits a high luminescence quantum yield and the peak half-width of the emission spectrum of the compound is small. Therefore, the compound represented by general formula (1) can achieve highly efficient color conversion and high color purity.

[0081] R 1 , R 3 , R 4 and R 6 Compared to when all hydrogen atoms are present, R 1 , R 3 , R 4 and R 6 When at least one of the groups is a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, the compound exhibits better thermal stability and light stability.

[0082] R 1 , R 3 , R 4 and R 6 may all be the same or different, and are preferably substituted or unsubstituted alkyl groups because they provide good solubility in matrix resins and solvents. As the alkyl group, a sterically bulky tert-butyl group is preferred from the viewpoint of preventing concentration quenching and improving the luminescence quantum yield. Furthermore, a methyl group is also preferred from the viewpoint of ease of synthesis and availability of raw materials.

[0083] R 7 and R8 is preferably an alkyl group, an aryl group, a heteroaryl group, fluorine, a fluorine-containing alkyl group, a fluorine-containing heteroaryl group or a fluorine-containing aryl group, or a cyano group. In particular, R is preferred because it is stable to excitation light and can provide a higher fluorescence quantum yield. 7 and R 8 is more preferably fluorine, a fluorine-containing aryl group or a cyano group.

[0084] Here, the fluorine-containing aryl group is an aryl group containing fluorine, such as a fluorophenyl group, a trifluoromethylphenyl group, and a pentafluorophenyl group. The fluorine-containing heteroaryl group is a heteroaryl group containing fluorine, such as a fluoropyridyl group, a trifluoromethylpyridyl group, and a trifluoropyridyl group. The fluorine-containing alkyl group is an alkyl group containing fluorine, such as a trifluoromethyl group and a pentafluoroethyl group.

[0085] By reducing the electron density on the boron atom, the stability of the compound represented by general formula (1) against oxygen is further improved, and as a result, the durability of the compound can be further improved. Therefore, fluorine or a cyano group is more preferred. 7 and R 8 When at least one of R is a cyano group, the electron density on the boron atom is lowered, which is preferable. On the other hand, in terms of obtaining a high fluorescence quantum yield and ease of synthesis, R 7 and R 8 is also preferably fluorine.

[0086] In general formula (1), R 1 ~R 8 and R 11 ~R 15 At least one of them contains a structure represented by the following general formula (2).

[0087] [ka]

[0088] L 1 is a single bond, an oxygen atom, a sulfur atom, a carbonyl group, -C(=O)O-, -OC(=O)- or -SiR c R d -It is.

[0089] L 2 is a substituted or unsubstituted alkylene group, a substituted or unsubstituted alkyleneoxy group, a substituted or unsubstituted alkylenethio group, a substituted or unsubstituted cycloalkylene group, a substituted or unsubstituted arylene group, a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted heteroarylene group.

[0090] R a is a hydrogen atom or a straight-chain or branched alkyl group.

[0091] R b is a hydrogen atom, a halogen, a linear or branched alkyl group, a substituted or unsubstituted cycloalkyl group, or a substituted or unsubstituted aryl group.

[0092] R c and R d are each independently selected from the group consisting of a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkoxysilyl group, and a silanol group.

[0093] n is an integer of 1 to 3.

[0094] In the compound represented by general formula (1), R 1 ~R 8 and R 11 ~R 15When at least one of the above contains a structure represented by general formula (2), it becomes possible to form a bond with the three-dimensional structure described below, thereby obtaining a three-dimensional structure containing a pyrromethene boron complex. As a result, the three-dimensional structure has luminescence properties, and since a matrix of the three-dimensional structure exists around the pyrromethene boron complex, a luminescent three-dimensional structure with excellent durability can be obtained.

[0095] Here, for example, "R 1 The term "contains a structure represented by general formula (2)" means that R 1 may itself be a structure represented by general formula (2), 1 may be a substituent containing a structure represented by general formula (2).

[0096] The alkylene group refers to a divalent or higher group derived from a saturated aliphatic hydrocarbon group such as a methyl group or an ethyl group, which may or may not have a substituent. Preferred alkylene groups include a methylene group, an ethylene group, an n-propylene group, an isopropylene group, an n-butylene group, a pentylene group, and a hexylene group. The number of carbon atoms in the alkylene group portion is not particularly limited, but is preferably in the range of 1 to 20, more preferably 1 to 6. One end of the alkylene group is L 1 and the other end is bonded to the silicon atom of general formula (2).

[0097] Furthermore, an oxyalkylene group, alkyleneoxy group, thioalkylene group, or alkylenethio group may be present between the alkylene group and the silicon atom, and among these, an oxyalkylene group having 1 to 4 carbon atoms and a thioalkylene group having 1 to 4 carbon atoms are preferred.

[0098] The alkyleneoxy group is a group in which an oxygen atom is bonded to an alkylene group, and one end of the alkylene group is L. 1and the other end is bonded to an oxygen atom. The oxygen atom is bonded to the silicon atom of general formula (2). The alkyleneoxy group may or may not have a substituent. Preferred alkylene groups in the alkyleneoxy group include methylene, ethylene, n-propylene, isopropylene, n-butylene, pentylene, and hexylene. The number of carbon atoms in the alkylene group portion is not particularly limited, but is preferably in the range of 1 to 20, more preferably 1 to 6.

[0099] Furthermore, an alkylene group, an alkyleneoxy group, or an alkylenethio group may be present between the oxygen atom in the alkyleneoxy group and the silicon atom of general formula (2), and among these, an alkylene group having 1 to 4 carbon atoms and an alkyleneoxy group having 1 to 4 carbon atoms are preferred.

[0100] An alkylenethio group is an alkyleneoxy group in which the oxygen atom bonded to the alkylene group is replaced with a sulfur atom. The alkylenethio group may or may not have a substituent. Preferred alkylene groups in the alkylenethio group include methylene, ethylene, n-propylene, isopropylene, n-butylene, pentylene, and hexylene. The number of carbon atoms in the alkylene group is not particularly limited, but is preferably in the range of 1 to 20, more preferably 1 to 6.

[0101] In addition, an alkylene group, an alkyleneoxy group, or an alkylenethio group may be present between the acid sulfur atom in the alkylenethio group and the silicon atom of general formula (2), and among these, an alkylene group having 1 to 4 carbon atoms and an alkyleneoxy group having 1 to 4 carbon atoms are preferred.

[0102] The cycloalkylene group refers to a divalent or higher group derived from a saturated alicyclic hydrocarbon group such as a cyclopropyl group or a cyclohexyl group, which may or may not have a substituent. Preferred cycloalkylene groups include saturated alicyclic hydrocarbon groups such as a cyclopropylene group, a cyclohexylene group, a norbornylene group, and an adamantylene group. The number of carbon atoms in the cycloalkylene group portion is not particularly limited, but is preferably in the range of 3 to 20.

[0103] The arylene group refers to a divalent or higher group derived from an aromatic hydrocarbon group such as benzene, naphthalene, biphenyl, terphenyl, fluorene, or phenanthrene, and may or may not have a substituent. A divalent or trivalent arylene group is preferred. Specific examples of the arylene group include a phenylene group, a biphenylene group, and a naphthylene group. The number of carbon atoms in the arylene group is not particularly limited, but is preferably in the range of 1 to 30.

[0104] The heteroarylene group refers to a divalent or higher group derived from an aromatic group having one or more atoms other than carbon in the ring, such as pyridine, quinoline, pyrimidine, pyrazine, triazine, quinoxaline, quinazoline, dibenzofuran, or dibenzothiophene, and may or may not have a substituent. A divalent or trivalent heteroarylene group is preferred. The number of carbon atoms in the heteroarylene group is not particularly limited, but is preferably in the range of 2 to 30. Specific examples of the heteroarylene group include a 2,6-pyridylene group, a 2,5-pyridylene group, a 2,4-pyridylene group, a 3,5-pyridylene group, a 3,6-pyridylene group, a 2,4,6-pyridylene group, a 2,4-pyrimidinylene group, a 2,5-pyrimidinylene group, a 4,6-pyrimidinylene group, a 2,4,6-pyrimidinylene group, a 2,4,6-triazinylene group, a 4,6-dibenzofuranylene group, a 2,6-dibenzofuranylene group, a 2,8-dibenzofuranylene group, and a 3,7-dibenzofuranylene group.

[0105] R ais preferably a methyl group, an ethyl group, or an isopropyl group, from the viewpoint of easily forming a bond with the three-dimensional structure described later and suppressing the formation of a bond between the general formula (1). Among these, a methyl group or an ethyl group is more preferred, from the viewpoint of rapid hydrolysis and easier formation of a bond with the three-dimensional structure.

[0106] R b is preferably a hydrogen atom, a linear or branched alkyl group, or a substituted or unsubstituted aryl group, and more preferably a linear or branched alkyl group, or a substituted or unsubstituted aryl group.

[0107] R c and R d is preferably a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted silyl group, and more preferably a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group.

[0108] Regarding n, the larger the number of n, the more bonding points there are between the three-dimensional structure described below and the compound represented by general formula (1), and the easier it is for the compound represented by general formula (1) to be incorporated into the three-dimensional structure. From this point of view, n is preferably 2 or 3, and more preferably 3.

[0109] -L 1 -L 2 The structural moiety of L is a bonding group that connects the compound represented by general formula (1) with the silicon atom in the partial structure represented by general formula (2). It is preferable that the structure is stable and that it is less susceptible to decomposition by hydrolysis. 1 is a single bond, an oxygen atom, a sulfur atom, a carbonyl group, or -SiR c R d - is preferable. 1 -L 2 When the structural portion of L- has a long chain or a bulky structure, quenching due to aggregation of the compounds represented by general formula (1) is suppressed. 2is preferably a substituted or unsubstituted alkylene group, a substituted or unsubstituted alkyleneoxy group, or a substituted or unsubstituted alkylenethio group, and more preferably a substituted or unsubstituted alkylene group.

[0110] In particular, L 1 is a single bond, an oxygen atom, a carbonyl group, -C(=O)O-, -OC(=O)-, or -SiR c R d - is selected from a candidate set consisting of L 2 is a substituted or unsubstituted alkylene group or a substituted or unsubstituted alkyleneoxy group, and n is preferably 2 or 3.

[0111] Furthermore, the compound represented by general formula (1) satisfies either the following (A) or (B): (A)R 11 ~R 15 At least one of the groups is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. (B)R 2 and R 5 is a hydrogen atom.

[0112] When the compound represented by general formula (1) satisfies (A) or (B), durability can be improved when incorporated into a three-dimensional structure.

[0113] (When the compound represented by general formula (1) satisfies (A)) When the compound represented by general formula (1) satisfies (A), the bulkiness of the compound represented by general formula (1) is improved, and molecular aggregation can be prevented. As a result, the luminous efficiency and durability of the compound represented by general formula (1) are improved. Furthermore, when the compound represented by general formula (1) satisfies (A), the carbon-carbon bond between the phenyl group and the pyrromethene boron complex skeleton in the compound represented by general formula (1) can be appropriately twisted, thereby improving photostability.

[0114] In the compound represented by general formula (1), R 11~R 15 Preferably, at least two of the groups are substituted or unsubstituted aryl groups or substituted or unsubstituted heteroaryl groups. By having the above structure, the carbon-carbon bond between the phenyl group and the pyrromethene boron complex skeleton in the compound represented by general formula (1) can be appropriately twisted, and the rotational motion of the phenyl group can be further suppressed, making it possible to obtain a higher luminescence quantum yield.

[0115] When the compound represented by general formula (1) satisfies (A), it is more preferably a compound represented by general formula (3) or (4).

[0116] [ka]

[0117] In general formula (3) or (4), R 1 ~R 8 and R 11 ~R 15 The definition of R is the same as in general formula (1). 21 ~R 40each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted alkynyl group, a hydroxyl group, a thiol group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted aryl ether group, a substituted or unsubstituted aryl thioether group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a halogen atom, a cyano group, an aldehyde group, a substituted or unsubstituted carbonyl group, a carboxyl group, a methyl ... and n is 0 or 1. The substituent is selected from the group consisting of a carboxyl group, a substituted or unsubstituted oxycarbonyl group, a substituted or unsubstituted carbamoyl group, a substituted or unsubstituted ester group, a substituted or unsubstituted amido group, a substituted or unsubstituted acyl group, a substituted or unsubstituted sulfonyl group, a substituted or unsubstituted sulfonate ester group, a substituted or unsubstituted sulfonamido group, an amino group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkoxysilyl group, a substituted or unsubstituted silanol group, a substituted or unsubstituted siloxanyl group, a substituted or unsubstituted boryl group, and a substituted or unsubstituted phosphine oxide group. However, in the general formula (3), R 11 , R 13 , R 15 and R 21 ~R 30 At least one of the formulas (2) contains a structure represented by general formula (4), and in general formula (4), R 12 ~R 14 and R 31 ~R 40 At least one of them contains a structure represented by general formula (2).

[0118] When the compound represented by general formula (1) is a compound represented by general formula (3) or (4), the torsion of the carbon-carbon bond between the phenyl group and the pyrromethene boron complex skeleton in the compound represented by general formula (1) can be increased, making it possible to obtain a higher luminescence quantum yield. In addition, the bulkiness of the structure of the compound represented by general formula (1) can be increased, preventing molecular aggregation, resulting in further improved luminescence efficiency and durability of the compound represented by general formula (1).

[0119] In addition, in the general formula (3), R 11 , R 13 , R 15 and R 21 ~R 30 At least two of the general formula (4) contain a structure represented by general formula (2), and in general formula (4), R 12 ~R 14 and R 31 ~R 40 It is more preferable that at least two of them contain a structure represented by general formula (2). When the compound represented by general formula (3) or general formula (4) satisfies the above, it is possible to improve the incorporation efficiency into the three-dimensional structure while maintaining a high luminescence quantum yield. The greater the number of reaction sites between the three-dimensional structure and the compound represented by general formula (3) or general formula (4), the higher the incorporation efficiency into the three-dimensional structure. 11 , R 13 , R 15 and R 21 ~R 30 , R 12 ~R 14 and R 31 ~R 40 It is preferable that at least two of the above contain a partial structure represented by general formula (2), which can improve the efficiency of incorporation into the three-dimensional structure.

[0120] Also, R 11 , R 13 , R 15 and R 21 ~R 30 , R 12 ~R 14 and R 31 ~R40 When the compound contains the structure represented by general formula (2), twisting or distortion is unlikely to occur in the pyrromethene boron complex skeleton, allowing high planarity to be maintained. In addition, the compound can be efficiently incorporated into a three-dimensional structure while maintaining the twist of the carbon-carbon bond between the phenyl group and the pyrromethene boron complex skeleton, thereby making it possible to suppress molecular aggregation during the incorporation process and maintain high luminescence properties.

[0121] It is more preferable that the compound represented by general formula (3) is a compound represented by general formula (5), and that the compound represented by general formula (4) is a compound represented by general formula (6).

[0122] [ka]

[0123] L in general formula (5) or general formula (6) 1 , L 2 , R 1 ~R 8 , R 11 ~R 15 , R 31 ~R 40 , R a , R b and n is defined as in general formula (2), general formula (3) or general formula (4).

[0124] The compound represented by general formula (5) or general formula (6) is a compound having a structure represented by general formula (1) and a partial structure (-L 1 -L 2 -Si(OR a ) n R b 3-n ) are positioned apart from each other. This makes it possible for the compound represented by general formula (5) or general formula (6) to be efficiently incorporated into a three-dimensional structure while maintaining the inherent high luminescence properties and high durability of the structure represented by general formula (1), which is preferable in that a three-dimensional structure with higher luminescence efficiency and durability can be obtained.

[0125] In general formula (5) or general formula (6), R 2 and R 5 are each independently selected from the group consisting of a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a halogen atom, and a substituted or unsubstituted silyl group. Among these, from the viewpoints of thermal stability and stability against light, a hydrogen atom, an alkyl group, or an aryl group is more preferred, and a hydrogen atom is particularly preferred because of its particularly excellent stability against light. Furthermore, from the viewpoint of easily obtaining a narrow half-width in the emission spectrum, R 2 and R 5 is preferably a hydrogen atom.

[0126] (When the compound represented by general formula (1) satisfies (B)) When the compound represented by general formula (1) satisfies (B), the stability of the compound represented by general formula (1) against heat and light is improved and the half-width of the emission spectrum is narrowed, which makes it possible to improve the luminescence properties and durability of the compound represented by general formula (1).

[0127] In addition to the compound represented by general formula (1) satisfying (B), R 11 ~R 15 At least one of the groups is preferably a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, or a halogen atom.

[0128] R 11 ~R 15When at least one of the groups is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group, the bulkiness of the compound is increased, preventing molecular aggregation. As a result, the luminous efficiency and durability of the compound represented by general formula (1) are further improved. Furthermore, in the compound represented by general formula (1), the carbon-carbon bond between the phenyl group and the pyrromethene boron complex skeleton is appropriately twisted, further improving photostability.

[0129] Also, R 11 ~R 15 When at least one of R is a substituted or unsubstituted alkyl group or a substituted or unsubstituted alkoxy group, the compatibility of the compound represented by general formula (1) with the solvent is increased, and the luminous efficiency is further improved. 11 ~R 15 At least one of these is more preferably a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, or a methoxy group, and from the viewpoints of improving dispersibility and preventing quenching due to aggregation of molecules, a tert-butyl group or a methoxy group is particularly preferred.

[0130] Also, R 11 ~R 15 When at least one of the groups is a halogen, the stability of the compound represented by general formula (1) against oxygen is improved, and durability is further improved. Among halogens, a fluorine atom, which has strong electron-withdrawing properties, is preferred.

[0131] Among these, from the viewpoint of further improving the luminous efficiency and durability of the compound represented by general formula (1), R 11 ~R 15 At least one of R is preferably a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group, 11 ~R 15It is more preferable that at least two of the groups be substituted or unsubstituted aryl groups or substituted or unsubstituted heteroaryl groups. By having the above structure, the carbon-carbon bond between the phenyl group and the pyrromethene boron complex skeleton in the compound represented by general formula (1) can be appropriately twisted, and the rotational motion of the phenyl group can be further suppressed, making it possible to obtain a higher luminescence quantum yield.

[0132] The compound represented by general formula (1) satisfies (B) and R 11 and R 15 , or R 12 and R 14 is particularly preferably a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. The above structure increases the twist of the carbon-carbon bond between the phenyl group and the pyrromethene boron complex skeleton, resulting in a higher luminescence quantum yield. Furthermore, the bulkiness of the structure of the compound represented by general formula (1) increases, preventing molecular aggregation. As a result, the luminescence efficiency and durability of the compound represented by general formula (1) are improved.

[0133] Examples of the compound represented by general formula (1) are shown below, but the compound is not limited to these.

[0134] [ka]

[0135] [ka]

[0136] [ka]

[0137] [ka]

[0138]

change

[0139]

change

[0140]

change

[0141]

change

[0142]

change

[0143]

change

[0144]

change

[0145]

change

[0146]

change

[0147]

change

[0148] The compound represented by the general formula (1) can be synthesized by the method described in, for example, JP-A-8-509471 or JP-A-2000-208262. The compound is reacted with a metal salt in the presence of a base to give the desired pyrromethene metal complex. You get a body.

[0149] Furthermore, the synthesis of pyrromethene-boron fluoride complexes can be carried out with reference to methods described in J. Org. Chem., vol. 64, No. 21, pp. 7813-7819 (1999), Angew. Chem., Int. Ed. Engl., vol. 36, pp. 1333-1335 (1997), etc., to synthesize compounds represented by general formula (1). For example, a compound represented by the following general formula (10) and a compound represented by the following general formula (11) are heated in 1,2-dichloroethane in the presence of phosphorus oxychloride, and then a compound represented by the following general formula (12) is reacted in 1,2-dichloroethane in the presence of triethylamine to obtain the compound represented by general formula (1). However, the present invention is not limited to this method. Here, R 1 ~R 8 , R 11 ~R 15 is the same as explained above. J represents a halogen.

[0150] [ka]

[0151] Furthermore, when introducing an aryl group or a heteroaryl group, a method of forming a carbon-carbon bond using a coupling reaction between a halogenated derivative and a boronic acid or a boronate ester derivative can be used, but the present invention is not limited thereto. Similarly, when introducing an amino group or a carbazolyl group, a method of forming a carbon-nitrogen bond using a coupling reaction between a halogenated derivative and an amine or a carbazole derivative in the presence of a metal catalyst such as palladium can be used, but the present invention is not limited thereto.

[0152] Furthermore, the compound represented by general formula (1) containing the structure represented by general formula (2) can be synthesized by synthesizing a pyrromethene metal complex by the known method described above, followed by bonding a siloxane-containing group. Methods for bonding a siloxane-containing group include, but are not limited to, hydrosilylation of an aliphatic unsaturated group using a siloxane having a Si-H bond.

[0153] An example of a method for producing the compound represented by general formula (1) is a method in which an olefin compound represented by the following general formula (13) is reacted with a siloxane compound having a Si-H bond represented by the following general formula (14) in the presence of a platinum catalyst.

[0154] [ka]

[0155] In general formula (13), R 1 ~R 8 and R 11 ~R 15 The definition of is the same as in general formula (1), but R 1 ~R 6 and R 11 ~R 15 at least one of which is a substituted or unsubstituted alkynyl group or a substituted or unsubstituted alkenyl group having an aliphatic carbon-carbon unsaturated bond at a terminal, and is selected from the group consisting of an oxygen atom, a sulfur atom, a carbonyl group, -C(=O)O-, -OC(=O)-, and -SiR c R d -, or a combination thereof, provided that oxygen and sulfur heteroatoms are not adjacent to each other. c and R d The definition of is the same as in general formula (1).

[0156] Specific examples of these include alkenyl groups such as a vinyl group, an isopropenyl group, an allyl group, a 1-methylpropenyl group, a 3-butenyl group, a 4-pentenyl group, a 5-hexenyl group, a 6-heptenyl group, a 7-octenyl group, an 8-nonenyl group, a 9-decenyl group, a 10-undecenyl group, an 11-dodecenyl group, a 12-tridecenyl group, a 13-tetradecenyl group, a 14-pentadecenyl group, a 15-hexadecenyl group, a 16-heptadecenyl group, a 17-octadecenyl group, an 18-nonadecenyl group, and a 19-icosenyl group; an ethynyl group; Examples of suitable alkenyl groups include alkynyl groups such as propargyl, 3-butynyl, 4-pentynyl, 5-hexynyl, 6-heptynyl, 7-octynyl, 8-nonynyl, 9-decynyl, 10-undecynyl, and 11-dodecynyl groups; and alkenyl groups containing heteroatoms such as allyloxy, 2-oxa-4-pentenyl, 3-oxa-2-methyl-4-pentenyl, 3-oxa-5-hexenyl, 3-oxa-2-methyl-5-hexenyl, 3,6-dioxa-7-octenyl, and 3-thia-4-pentenyl groups.

[0157] [ka]

[0158] In general formula (14), R a , R b The definitions of and n are the same as in general formula (1). In addition, the compound represented by general formula (14) has a Si-H bond that is subject to a hydrosilylation reaction.

[0159] Specific examples of the compound represented by general formula (14) include trimethoxysilane, triethoxysilane, triisopropoxysilane, dimethoxymethylsilane, diethoxymethylsilane, diisopropoxymethylsilane, dimethoxyphenylsilane, diethoxyphenylsilane, diisopropoxyphenylsilane, etc., with trimethoxysilane, triethoxysilane, and triisopropoxysilane being preferred, and trimethoxysilane and triethoxysilane being more preferred because they have many bonding points with the three-dimensional structure, hydrolysis is rapid, and they are more likely to form bonds with the three-dimensional structure. Furthermore, dimethoxymethylsilane and diethoxymethylsilane are also preferred from the viewpoint of the synthesis yield in the reaction of the olefin compound represented by general formula (13) with the siloxane compound represented by general formula (14).

[0160] In the production method of the present invention, an olefin compound represented by general formula (13) and a siloxane compound represented by general formula (14) are reacted in the presence of a platinum catalyst to produce the compound. Specific examples of platinum catalysts include platinum compounds such as chloroplatinic acid, platinum(0) divinyltetramethyldisiloxane complex, platinum(0) tetravinyltetramethylcyclotetrasiloxane complex, tetrakistriphenylphosphine platinum, dichlorobistriphenylphosphine platinum, dichlorobisacetonitrile platinum, dichlorobisbenzonitrile platinum, and dichlorocyclooctadiene platinum, as well as solid-supported platinum such as platinum supported on activated carbon and platinum supported on silica gel. The amount of platinum catalyst used is not particularly limited, but is preferably 0.000001 to 0.01 moles, particularly 0.00001 to 0.001 moles, per mole of the olefin compound of general formula (13).

[0161] The compounding ratio of the olefin compound represented by general formula (13) to the siloxane compound represented by general formula (14) is not particularly limited, but from the viewpoints of reactivity and productivity, the amount of the compound of general formula (14) used per mole of the compound of general formula (13) is preferably 0.5 to 3 moles, particularly preferably 1.0 to 2.0 moles.

[0162] The reaction temperature for the above reaction is preferably 0 to 200°C, particularly 20 to 100°C, and the reaction time is preferably 0.1 to 20 hours, particularly 1 to 10 hours. The reaction temperature and time can be appropriately determined by those skilled in the art. Preferred solvents include ether-based and hydrocarbon-based solvents, and aprotic polar solvents, such as pentane, hexane, diethyl ether, tetrahydrofuran, dioxane, toluene, xylene, acetonitrile, N,N-dimethylformamide, and mixed solvents thereof.

[0163] As a synthesis method other than the above, it can also be produced by reacting a pyrromethene metal complex having a substituent containing a Si-H group at its terminal with a siloxane compound containing an aliphatic carbon-carbon unsaturated bond at its terminal in the presence of a platinum catalyst.

[0164] A method for synthesizing a pyrromethene metal complex having a substituent containing a Si-H group includes a method for generating a carbon-carbon bond using a coupling reaction between a halogenated derivative and a boronic acid or boronic acid ester derivative having a substituent containing a Si-H group, but the present invention is not limited to this method.

[0165] Examples of siloxane compounds having an aliphatic carbon-carbon unsaturated bond at a terminal include vinyltrimethoxysilane, vinyltriisopropoxysilane, allyltrimethoxysilane, vinyltriethoxysilane, allyltriethoxysilane, vinyltris(2-methoxyethoxy)silane, trimethoxy(7-octen-1-yl)silane, dimethoxymethylvinylsilane, and diethoxymethylvinylsilane. Of these, trialkoxysilanes having an aliphatic carbon-carbon unsaturated bond at a terminal, such as vinyltrimethoxysilane, vinyltriisopropoxysilane, allyltrimethoxysilane, vinyltriethoxysilane, allyltriethoxysilane, vinyltris(2-methoxyethoxy)silane, and trimethoxy(7-octen-1-yl)silane, are preferred.

[0166] The compound represented by general formula (1) preferably emits light with a peak wavelength observed in the range of 500 nm to less than 580 nm when using excitation light with a wavelength in the range of 400 nm to 500 nm. Hereinafter, emission with a peak wavelength in the range of 500 nm to less than 580 nm will be referred to as "green emission." Generally, the greater the energy of excitation light, the more likely it is that the material will be decomposed. However, excitation light with a wavelength in the range of 400 nm to 500 nm has a relatively small excitation energy, so that green emission with good color purity can be obtained without decomposing the compound represented by general formula (1).

[0167] As described above, in order to improve color reproducibility, it is preferable that the half width of the emission spectrum of each of blue, green, and red is small, and in particular, a small half width of the emission spectrum of green light is effective for improving color reproducibility. For example, the half width of the emission spectrum of the compound represented by general formula (1) is preferably 50 nm or less, more preferably 40 nm or less, even more preferably 35 nm or less, and particularly preferably 30 nm or less.

[0168] As described above, the compound represented by general formula (1) can achieve both high luminous efficiency and high durability, and therefore can be used not only in color conversion filters but also as a dye for dye-sensitized solar cells, a photoelectric conversion dye for organic solar cells and the like, a luminescent dye for organic electroluminescence and dye lasers and the like, a dye for agricultural and horticultural films, a coloring material for pigments and the like.

[0169] <3D structure> The three-dimensional structure according to an embodiment of the present invention is constituted by a covalent bond between an element M and an oxygen atom, the element M being an element selected from the group consisting of Si, Ti, and Al, and including a partial structure represented by general formula (7).

[0170] [ka]

[0171] In the general formula (7), the symbol represents a bonding point with the three-dimensional structure.

[0172] R 101 ~R 106 and R 111 ~R 115 are each independently, L 3 or a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted alkynyl group, a hydroxyl group, a thiol group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted aryl ether group, a substituted or unsubstituted aryl thioether group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a halogen atom, a cyano group, an aldehyde group, a substituted or unsubstituted carbonyl group, It is selected from the group consisting of a carboxyl group, a substituted or unsubstituted oxycarbonyl group, a substituted or unsubstituted carbamoyl group, a substituted or unsubstituted ester group, a substituted or unsubstituted amide group, a substituted or unsubstituted acyl group, a substituted or unsubstituted sulfonyl group, a substituted or unsubstituted sulfonate ester group, a substituted or unsubstituted sulfonamide group, an amino group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkoxysilyl group, a substituted or unsubstituted silanol group, a substituted or unsubstituted siloxanyl group, a substituted or unsubstituted boryl group, and a substituted or unsubstituted phosphine oxide group.

[0173] R 107 and R 108 are each independently, L 3or is selected from the group consisting of a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted alkynyl group, a hydroxyl group, a thiol group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted aryl ether group, a substituted or unsubstituted aryl thioether group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a halogen, and a cyano group.

[0174] However, R 101 ~R 108 and R 111 ~R 115 At least one of the 3 or a single bond connecting to L 3 has a substituent that bonds to

[0175] L 3 is a single bond, an oxygen atom, a sulfur atom, a carbonyl group, -C(=O)O-, -OC(=O)-, or -SiR f R g -It is. L 4 is a substituted or unsubstituted alkylene group, a substituted or unsubstituted alkyleneoxy group, a substituted or unsubstituted alkylenethio group, a substituted or unsubstituted cycloalkylene group, a substituted or unsubstituted arylene group, a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted heteroarylene group.

[0176] However, R f and R g are each independently selected from the group consisting of a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkoxysilyl group, and a silanol group.

[0177] R eis selected from a hydrogen atom, a halogen atom, a linear or branched alkyl group, a substituted or unsubstituted cycloalkyl group, and a substituted or unsubstituted aryl group. m is an integer of 1 to 3.

[0178] However, the partial structure represented by general formula (7) satisfies either the following (C) or (D). (C)R 111 ~R 115 At least one of the groups is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. (D)R 102 and R 105 is a hydrogen atom.

[0179] The three-dimensional structure according to the embodiment of the present invention is preferably formed by a covalent bond between an element M and an oxygen atom, and the element M is an element selected from the group consisting of Si, Ti, and Al. That is, the three-dimensional structure is an organic-inorganic hybrid material that is formed by a partial structure of an organic substance represented by general formula (7) and an inorganic oxide formed by a covalent bond between the element M and an oxygen atom. When the element M is Si, the inorganic oxide is preferably a silicon oxide (SiO ) such as silica. x ), and when element M is Al, aluminum oxide such as alumina (Al n O m ), and when element M is Ti, titanium oxide (TiO y )

[0180] Among these, the element M is preferably Si or Al from the viewpoint of low permeability to oxygen and water vapor, and more preferably Si from the viewpoint of availability of raw materials and ease of forming a three-dimensional network.

[0181] The partial structure represented by general formula (7) and the element M contained in the three-dimensional structure according to the embodiment of the present invention may each be of one type or two or more types.

[0182] The definitions of alkyl group, cycloalkyl group, heterocyclic group, alkenyl group, cycloalkenyl group, alkynyl group, hydroxyl group, thiol group, alkoxy group, alkylthio group, aryl ether group, aryl thioether group, aryl group, heteroaryl group, halogen, cyano group, aldehyde group, carbonyl group, carboxyl group, oxycarbonyl group, carbamoyl group, ester group, amide group, acyl group, sulfonyl group, sulfonate ester group, sulfonamide group, amino group, nitro group, silyl group, alkoxysilyl group, silanol group, siloxanyl group, boryl group, and phosphine oxide group are the same as those for the compound represented by general formula (1).

[0183] The partial structure represented by general formula (7) has a pyrromethene boron complex skeleton. The pyrromethene boron complex skeleton is a strong and highly planar skeleton. Therefore, the partial structure having the pyrromethene boron complex skeleton exhibits a high luminescence quantum yield, and the peak half-width of the emission spectrum of the compound is small. Therefore, the partial structure represented by general formula (7) can achieve highly efficient color conversion and high color purity.

[0184] R 101 , R 103 , R 104 and R 106 Compared to when all hydrogen atoms are present, R 101 , R 103 , R 104 and R 106 When at least one of the groups is a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, the compound exhibits better thermal stability and light stability.

[0185] R 101 , R 103 , R 104 and R 106may all be the same or different, and are preferably substituted or unsubstituted alkyl groups because they provide good solubility in matrix resins and solvents. In this case, the alkyl group is preferably a sterically bulky tert-butyl group from the viewpoint of preventing concentration quenching and improving the luminescence quantum yield. Furthermore, a methyl group is also preferred from the viewpoints of ease of synthesis and availability of raw materials.

[0186] R 108 and R 109 is preferably an alkyl group, an aryl group, a heteroaryl group, fluorine, a fluorine-containing alkyl group, a fluorine-containing heteroaryl group or a fluorine-containing aryl group, or a cyano group. In particular, R is preferred because it is stable to excitation light and can provide a higher fluorescence quantum yield. 108 and R 109 is more preferably a fluorine atom, a fluorine-containing aryl group, or a cyano group. The explanation of these groups is as above.

[0187] By reducing the electron density on the boron atom, the stability of the partial structure represented by general formula (7) against oxygen is further improved, and as a result, the durability of the compound can be further improved. Therefore, fluorine or a cyano group is more preferred. 108 and R 109 When at least one of R is a cyano group, the electron density on the boron atom is lowered, which is preferable. On the other hand, in terms of obtaining a high fluorescence quantum yield and ease of synthesis, R 108 and R 109 is also preferably fluorine.

[0188] Among the partial structures represented by general formula (7), R 101 ~R 108 and R 111 ~R 115 At least one of the 3 or a single bond connecting to L 3 has a substituent that bonds to

[0189] R 101 ~R 108 and R 111~R 115 At least one of the 3 or a single bond connecting to L 3 By having a substituent bonded to the group, the three-dimensional structure can include a partial structure represented by general formula (7). This allows the three-dimensional structure to have luminescence properties, and since an inorganic oxide matrix consisting of the three-dimensional structure is present around the partial structure represented by general formula (7), a luminescent three-dimensional structure with excellent durability can be obtained.

[0190] In the partial structure represented by general formula (7), R 111 ~R 115 At least one of the 3 or a single bond connecting to L 3 In this case, twisting or distortion is unlikely to occur in the pyrromethene boron complex skeleton, and high planarity can be maintained, and the twist of the carbon-carbon bond between the phenyl group and the pyrromethene boron complex skeleton can be maintained, resulting in a three-dimensional structure with superior luminous efficiency and luminous properties.

[0191] The higher the content of the partial structure represented by general formula (7) in the three-dimensional structure, the better the light-emitting property. 111 ~R 115 At least two of the 3 or a single bond connecting to L 3 It is more preferred that the aryl group has a substituent that bonds to the aryl group.

[0192] In addition, from the viewpoint of increasing the photostability of the partial structure represented by general formula (7), R 111 ~R 115 R is preferably a moderately bulky substituent. This can prevent aggregation of the partial structure represented by general formula (7) in the three-dimensional structure, and can improve the luminous efficiency and durability of the partial structure represented by general formula (7). 111 ~R 115Preferred substituents in include a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted heteroaryl group, and among these, a substituted or unsubstituted phenyl group or a substituted or unsubstituted heteroaryl group is more preferred.

[0193] In the partial structure represented by general formula (7), L 3 is a single bond, an oxygen atom, a sulfur atom, a carbonyl group, -C(=O)O-, -OC(=O)-, or -SiR f R g -It is. L 3 is preferably a stable structure, and is preferably a single bond, an oxygen atom, a sulfur atom, a carbonyl group, or -SiR from the viewpoint of being less susceptible to decomposition by hydrolysis. f R g - is preferred.

[0194] In the partial structure represented by general formula (7), L 4 L is a substituted or unsubstituted alkylene group, a substituted or unsubstituted alkyleneoxy group, a substituted or unsubstituted alkylenethio group, a substituted or unsubstituted cycloalkylene group, a substituted or unsubstituted arylene group, a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted heteroarylene group. 4 When L has a long chain or a bulky structure, quenching due to aggregation of the partial structures represented by general formula (7) is suppressed. 4 is preferably a substituted or unsubstituted alkylene group, a substituted or unsubstituted alkyleneoxy group, or a substituted or unsubstituted alkylenethio group, and particularly preferably a substituted or unsubstituted alkylene group or a substituted or unsubstituted alkyleneoxy group.

[0195] R e is selected from a hydrogen atom, a halogen atom, a linear or branched alkyl group, a substituted or unsubstituted cycloalkyl group, and a substituted or unsubstituted aryl group.

[0196] R f and Rg is preferably a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted silyl group, and more preferably a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group.

[0197] m is an integer of 1 to 3. As the number of m increases, the number of bonding points between the inorganic oxide matrix in the three-dimensional structure and the partial structure represented by general formula (7) increases, making it possible to increase the content of the partial structure represented by general formula (7). Therefore, m is preferably 2 or 3, and more preferably 3.

[0198] In the partial structure represented by general formula (7), L 3 is a single bond, an oxygen atom, a sulfur atom, a carbonyl group, -C(=O)O-, -OC(=O)-, or -SiR f R g - and L 4 is a substituted or unsubstituted alkylene group or a substituted or unsubstituted alkyleneoxy group, and m is more preferably 2 or 3.

[0199] The partial structure represented by general formula (7) satisfies either the following (C) or (D). (C)R 111 ~R 115 At least one of the groups is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. (D)R 102 and R 105 is a hydrogen atom.

[0200] When the partial structure represented by general formula (7) satisfies the above (C) or (D), the durability of the partial structure represented by general formula (7) can be improved.

[0201] When the partial structure represented by general formula (7) satisfies (C), the bulkiness of the partial structure represented by general formula (7) is improved, and molecular aggregation can be prevented. As a result, the luminous efficiency and durability of the partial structure represented by general formula (7) can be further improved. In addition, when the partial structure represented by general formula (7) satisfies (C), the carbon-carbon bond between the phenyl group and the pyrromethene boron complex skeleton in the partial structure represented by general formula (7) can be appropriately twisted, thereby improving photostability.

[0202] In the partial structure represented by general formula (7), R 111 ~R 115 Among these, at least two are preferably substituted or unsubstituted aryl groups or substituted or unsubstituted heteroaryl groups. By having the above structure, the carbon-carbon bond between the phenyl group and the pyrromethene boron complex skeleton in the partial structure represented by general formula (7) can be twisted appropriately, and the rotational motion of the phenyl group is further suppressed, making it possible to obtain a higher luminescence quantum yield. In particular, from the viewpoint of obtaining higher photostability, it is preferable to use R 111 and R 115 , or R 112 and R 114 is more preferably a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group.

[0203] When the partial structure represented by general formula (7) satisfies (D), the stability against heat and light is improved, and the durability of the partial structure represented by (7) can be improved. In addition, from the viewpoint of easily obtaining a narrow half-width in the emission spectrum, R 102 and R 105 is preferably a hydrogen atom.

[0204] The partial structure represented by general formula (7) is more preferably a partial structure represented by general formula (8) or (9).

[0205] [ka]

[0206] [ka]

[0207] In the general formulae (8) and (9), the symbol represents a bonding point to the three-dimensional structure.

[0208] R 102 and R 105 is a hydrogen atom.

[0209] R 101 , R 103 , R 104 , R 106 , R 111 ~R 115 and R 131 ~R 140 each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted alkynyl group, a hydroxyl group, a thiol group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted aryl ether group, a substituted or unsubstituted aryl thioether group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a halogen atom, a cyano group, an aldehyde group, a substituted or unsubstituted carbonyl group, a carboxyl group, a methyl ... and n is 0 or 1. The substituent is selected from the group consisting of a carboxyl group, a substituted or unsubstituted oxycarbonyl group, a substituted or unsubstituted carbamoyl group, a substituted or unsubstituted ester group, a substituted or unsubstituted amido group, a substituted or unsubstituted acyl group, a substituted or unsubstituted sulfonyl group, a substituted or unsubstituted sulfonate ester group, a substituted or unsubstituted sulfonamido group, an amino group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkoxysilyl group, a substituted or unsubstituted silanol group, a substituted or unsubstituted siloxanyl group, a substituted or unsubstituted boryl group, and a substituted or unsubstituted phosphine oxide group.

[0210] R107 and R 108 are each independently selected from the group consisting of a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted alkynyl group, a hydroxyl group, a thiol group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted aryl ether group, a substituted or unsubstituted aryl thioether group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a halogen atom, and a cyano group.

[0211] The partial structure represented by general formula (8) or general formula (9) is a pyrromethene boron complex skeleton that is responsible for light emission and -L 3 -L 4 This structure is such that the structural moiety represented by —Si(O—·)3 is separated from the structural moiety represented by general formula (8). This makes it possible to efficiently incorporate the partial structure represented by general formula (8) or general formula (9) into a three-dimensional structure while maintaining the inherent high luminescence properties and high durability of the partial structure represented by general formula (7), which is preferable in that it allows for the production of a three-dimensional structure with higher luminescence efficiency and durability.

[0212] The three-dimensional structure according to the embodiment of the present invention is preferably particulate in the color-converting composition described below. Hereinafter, such a form will be referred to as a "particulate color-converting material." The particulate color-converting material preferably has an average particle size of 0.010 μm to 100 μm, more preferably 0.010 μm to 30 μm, and even more preferably 0.010 μm to 10 μm. The average particle size is determined by measuring the particle size distribution using microscopy or laser diffraction scattering, but in principle, microscopy is used. However, if the measurement result using laser diffraction scattering is 1 μm or less, the particle size measured using laser diffraction scattering is used. Furthermore, in the case of microscopy, although not particularly limited, the particle size can be determined by measuring the particle size of approximately 100 isolated particles and calculating the average value.

[0213] <Method of manufacturing three-dimensional structures> The three-dimensional structure according to the embodiment of the present invention can be fabricated using a sol-gel method. Specifically, it can be fabricated by condensation polymerization of a mixture of a compound represented by general formula (1) and an organometallic compound having a structure represented by MX1 or MX3 in an appropriate organic solvent under hydrolysis conditions. Here, M is preferably an element selected from the group consisting of Si, Ti, and Al, and X is preferably an alkoxy group having 1 to 18 carbon atoms. Among these, the three-dimensional structure is preferably fabricated by the "Stober method," which is described in Journal of Colloid and Interface Science, 26, 62-69 (1968), and involves hydrolysis of a silicon-containing alkoxide compound such as tetraethoxysilane under alkaline conditions using aqueous ammonia or the like.

[0214] Specific examples of the organometallic compound when the element M is Si include tetraalkoxysilanes such as tetramethoxysilane (TMOS), tetraethoxysilane (TEOS), tetra-n-propoxysilane, and tetra-n-butoxysilane; dialkyl-tetraalkoxydisilanes such as tetrakis(methoxyethoxy)silane, tetrakis(ethoxyethoxy)silane, tetrakis(methoxyethoxyethoxy)silane, tetrakis(methoxypropoxy)silane, tetrakis(2-methylhexoxy)silane, and dimethyltetraethoxydisiloxane; tetraacyloxysilanes such as tetraacetoxysilane; tetraalkenyloxysilanes such as tetraallyloxysilane; and mixtures thereof, with TEOS, TMOS, or mixtures thereof being preferred. When the element M is Ti, examples thereof include tetraalkoxy titanates such as tetra-n-butyl titanate, tetraethoxytitanate, tetramethoxytitanate, and tetraisoproxytitanate, and when the element M is Al, examples thereof include trialkoxy aluminates such as tri-n-propoxyaluminate, triisopropoxyaluminate, and tri-n-butoxyaluminate.

[0215] Examples of organic solvents include alcohols such as ethanol, methanol, 1-propanol, 2-propanol, 1-methoxy-2-propanol, and mixtures thereof. However, the present invention is not limited thereto, and an appropriate solvent can be used taking into consideration the solubility of the compound represented by general formula (1), and a mixed solvent consisting of multiple solvents may also be used. Ethanol is preferred as an alcoholic solvent, and ethyl acetate, tetrahydrofuran, dichloromethane, and toluene are preferred as solvents that have excellent solubility for the compound represented by general formula (1).

[0216] To create hydrolysis conditions, an acid or a base must be added, and examples of acids include formic acid, phosphoric acid, hydrochloric acid, sulfuric acid, acetic acid, trifluoroacetic acid, methanesulfonic acid, trifluoromethanesulfonic acid, and p-toluenesulfonic acid. Examples of bases include sodium hydroxide, potassium hydroxide, ammonia, dimethylamine, and diethylamine. Hydrolysis is preferably carried out under basic conditions, and the base used is preferably ammonia or diethylamine, with ammonia being particularly preferred.

[0217] The concentration of the compound represented by general formula (1) is in the range of 0.05 to 1 mol / L, preferably 0.05 to 0.8 mol / L, more preferably 0.05 to 0.5 mol / L, based on the amount of the solvent.

[0218] The duration of the hydrolysis polycondensation reaction is in the range of 1 hour to 48 hours, preferably 1 hour to 24 hours, and more preferably 2 hours to 12 hours.

[0219] <Color-changing composition> A color-converting composition according to an embodiment of the present invention converts incident light into light with a longer wavelength than the incident light. This color-converting composition preferably contains a compound represented by general formula (1) or a three-dimensional structure containing a partial structure represented by general formula (7), and a binder resin. The compound represented by general formula (1) or the three-dimensional structure containing a partial structure represented by general formula (7) functions as a light-emitting material in the color-converting composition that converts incident light into light with a longer wavelength than the incident light.

[0220] The content of the compound represented by general formula (1) in the color-changing composition according to the embodiment of the present invention depends on the molar absorption coefficient, fluorescence quantum yield, and absorption intensity at the excitation wavelength of the compound, as well as the thickness and transmittance of the film to be produced, but is usually 1.0 × 10 -4 parts by weight to 30 parts by weight, 1.0 × 10 -3 It is more preferable that the content is 1.0×10 to 10 parts by weight. -2 Particularly preferably, the amount is from 1 part by weight to 5 parts by weight.

[0221] The content of the three-dimensional structure containing the partial structure represented by general formula (7) in the color-changing composition according to the embodiment of the present invention depends on the molar absorption coefficient of general formula (7) contained in the three-dimensional structure, the fluorescence quantum yield, the absorption intensity at the excitation wavelength, as well as the thickness and transmittance of the film to be produced, but is usually 1.0 × 10 relative to 100 parts by weight of the binder resin. -3 parts by weight to 50 parts by weight, 1.0 × 10 -2 It is more preferable that the content is 1.0×10 to 30 parts by weight. -1 Particularly preferably, the amount is from 1 part by weight to 20 parts by weight.

[0222] The color-converting composition according to the embodiment of the present invention may further contain, as a light-emitting material, a compound represented by general formula (1) or a three-dimensional structure containing a partial structure represented by general formula (7), (a) a light-emitting material (hereinafter referred to as "light-emitting material (a)") that emits light having a peak wavelength of 500 nm or more and less than 580 nm when excited with excitation light having a wavelength in the range of 400 nm or more and 500 nm or less.

[0223] Examples of the light-emitting material (a) include coumarin derivatives such as coumarin 6, coumarin 7, and coumarin 153; cyanine derivatives such as indocyanine green; fluorescein derivatives such as fluorescein, fluorescein isothiocyanate, and carboxyfluorescein diacetate; phthalocyanine derivatives such as phthalocyanine green; perylene derivatives such as diisobutyl-4,10-dicyanoperylene-3,9-dicarboxylate; pyrromethene derivatives; stilbene derivatives; oxazine derivatives; naphthalimide derivatives; pyrazine derivatives; benzimidazole derivatives; benzoxazole derivatives; benzothiazole derivatives; imidazopyridine derivatives; azole derivatives; compounds having fused aryl rings such as anthracene and their derivatives; aromatic amine derivatives; and organometallic complex compounds. Compounds having a structure represented by the general formula (1) are also suitable because they exhibit high color purity. Two or more of these compounds may be used.

[0224] Furthermore, the color-converting composition according to an embodiment of the present invention preferably contains, in addition to the compound represented by general formula (1), the three-dimensional structure containing the partial structure represented by general formula (7), and luminescent material (a), (b) a luminescent material (hereinafter referred to as "luminescent material (b)") that, upon being excited by either or both of excitation light having a wavelength in the range of 400 nm to 500 nm and the emission from the compound represented by general formula (1) or the luminescent material (a), exhibits luminescence whose peak wavelength is observed in the range of 580 nm to 750 nm. Hereinafter, luminescence whose peak wavelength is observed in the range of 580 nm to 750 nm will be referred to as "red luminescence."

[0225] Examples of the light-emitting material (b) include cyanine derivatives such as 4-dicyanomethylene-2-methyl-6-(p-dimethylaminostillyl)-4H-pyran, rhodamine derivatives such as rhodamine B, rhodamine 6G, rhodamine 101, and sulforhodamine 101, pyridine derivatives such as 1-ethyl-2-(4-(p-dimethylaminophenyl)-1,3-butadienyl)-pyridinium perchlorate, perylene derivatives such as N,N'-bis(2,6-diisopropylphenyl)-1,6,7,12-tetraphenoxyperylene-3,4:9,10-bisdicarboimide, porphyrin derivatives, pyrromethene derivatives, oxazine derivatives, pyrazine derivatives, compounds having fused aryl rings such as naphthacene and dibenzodiindenoperylene, and derivatives thereof, and organometallic complex compounds. Two or more of these may be used.

[0226] The color-converting composition according to the present invention comprises a compound represented by general formula (1), a three-dimensional structure containing a partial structure represented by general formula (7), and a light-emitting material (a), in addition to the light-emitting material (b). This enables the emission of white light when using excitation light with a wavelength in the range of 400 nm to 500 nm. Because a portion of the excitation light in the wavelength range of 400 nm to 500 nm is partially transmitted through the color-converting composition or component of the present invention, when a blue LED with a sharp emission peak is used, the composition exhibits a sharply shaped emission spectrum in each of the blue, green, and red colors, resulting in an emission spectrum with excellent color purity. As a result, a wider color gamut with more vivid colors can be efficiently produced, particularly in displays. Furthermore, in lighting applications, the composition exhibits improved emission characteristics, particularly in the green and red regions, compared to white LEDs that combine a blue LED with a yellow phosphor, which is currently the mainstream, resulting in improved color rendering and making it a desirable white light source.

[0227] The content of the luminescent material in the color-changing composition according to the embodiment of the present invention can be selected depending on the absorption coefficient, fluorescence quantum yield, and absorption intensity at the excitation wavelength of each compound or three-dimensional structure, as well as the thickness and transmittance of the film to be produced. Here, the content of the luminescent material refers to the total content when two or more luminescent materials are contained. The content of the luminescent material is 1.0 × 10 per 100 parts by weight of the binder resin. -2 The content of the three-dimensional structure refers to the total content when two or more types of three-dimensional structure are contained. The content of the three-dimensional structure is preferably 1.0 × 10 to 100 parts by weight of the binder resin. -1 Parts by weight to 20 parts by weight are preferred.

[0228] When the color-changing composition contains both a compound that emits green light (a compound represented by general formula (1), a three-dimensional structure represented by general formula (7), or a light-emitting material (a)) and a compound that emits red light (light-emitting material (b)), part of the green light is converted to red light, so the content w of the compound that emits green light or the three-dimensional structure a and the content of the compound that emits red light w b But, w a ≧w b The relationship between the content ratio of each material is preferably a :w b is preferably 200:1 to 3:1. a and w b is the weight percent relative to the weight of the binder resin.

[0229] In addition to the compound represented by general formula (1) or the three-dimensional structure containing the partial structure represented by general formula (7), the color-converting composition according to the embodiment of the present invention may contain other compounds as needed. For example, an assist dopant such as rubrene may be added to further enhance the efficiency of energy transfer from excitation light to the compound represented by general formula (1) or the three-dimensional structure containing the partial structure represented by general formula (7). Furthermore, if an emission color other than that of the compound represented by general formula (1) or the three-dimensional structure containing the partial structure represented by general formula (7) is desired, a desired organic light-emitting material, such as a coumarin-based dye or a rhodamine-based dye, can be added. In addition to these organic light-emitting materials, known light-emitting materials such as inorganic phosphors, fluorescent pigments, fluorescent dyes, and quantum dots can also be added in combination.

[0230] Examples of organic light-emitting materials other than the compound represented by general formula (1) and the three-dimensional structure containing the partial structure represented by general formula (7) are shown below, but are not particularly limited thereto.

[0231] [ka]

[0232] <Method of manufacturing color-changing composition> An example of a method for producing a color-changing composition according to an embodiment of the present invention is described below. The aforementioned compounds, three-dimensional structures, binder resin, and, if necessary, other additives and solvents are mixed to a predetermined composition, and then the color-changing composition is obtained by homogenizing or kneading the mixture using a stirrer / kneader. Examples of stirrers / kneaders include homogenizers, planetary stirrers, three-roller stirrers, ball mills, planetary ball mills, and bead mills. After mixing or dispersing, or during the mixing or dispersing process, degassing under vacuum or reduced pressure conditions is also preferred. It is also acceptable to premix certain components or to perform aging or other treatments. The desired solids concentration can also be achieved by removing the solvent using an evaporator.

[0233] <Binder resin> The color-changing composition according to the embodiment of the present invention may contain a binder resin in addition to the above-described compounds and three-dimensional structures. Materials with excellent moldability, transparency, heat resistance, and the like are preferably used as the binder resin. Examples of binder resins include known materials such as photocurable resist materials having reactive vinyl groups, such as acrylic acid-based, methacrylic acid-based, polyvinyl cinnamate-based, and cyclic rubber-based materials, epoxy resins, silicone resins (including organopolysiloxane cured products (crosslinked products) such as silicone rubber and silicone gel), urea resins, fluororesins, polycarbonate resins, acrylic resins, urethane resins, melamine resins, polyvinyl resins, polyamide resins, phenolic resins, polyvinyl alcohol resins, cellulose resins, aliphatic ester resins, aromatic ester resins, aliphatic polyolefin resins, and aromatic polyolefin resins. Furthermore, mixtures or copolymers of these resins may also be used as the binder resin. By appropriately designing these resins, binder resins useful for the color-changing material according to the embodiment of the present invention can be obtained.

[0234] Among these resins, from the viewpoints of transparency and dispersibility of the light-emitting material, any of acrylic resins, copolymer resins containing an acrylic acid ester or methacrylic acid ester moiety, polyester resins, cycloolefin resins, epoxy resins, and silicone resins is preferable. Also, from the viewpoint of heat resistance, hydrogenated styrene-based resins, resins having a fluorene skeleton, and copolymer resins containing these resins can be suitably used.

[0235] Examples of binder resins include thermosetting resins, photocurable resins, and thermoplastic resins. Thermoplastic resins have few reactive functional groups and contain few reactive impurities such as polymerization initiators and crosslinking agents, so they are less likely to inhibit the luminescence of the luminescent material and are therefore suitable for use. From the viewpoint of heat resistance, thermosetting resins and photocurable resins are suitable for use.

[0236] When the binder resin is a thermoplastic resin, the glass transition temperature (Tg) of the resin is not particularly limited, but is preferably 30°C or higher and 180°C or lower. A Tg of 30°C or higher suppresses molecular motion of the binder resin due to heat from incident light from a light source or heat generated by the device's operation, thereby suppressing changes in the dispersion state of the luminescent material and preventing deterioration of durability. Furthermore, a Tg of 180°C or lower ensures flexibility when molded into a sheet or the like. The Tg of the binder resin is more preferably 50°C or higher and 170°C or lower, even more preferably 70°C or higher and 160°C or lower, and particularly preferably 90°C or higher and 150°C or lower. The glass transition temperature of the thermoplastic resin can be measured using a commercially available measuring instrument (e.g., a differential scanning calorimeter manufactured by Seiko Electronics Industries Co., Ltd. (trade name: DSC6220, heating rate: 0.5°C / min)).

[0237] The binder resin is preferably a polymer or hydrogenation product of at least one monomer selected from the group consisting of acrylic acid esters, methacrylic acid esters, and styrene, and has a Tg of 100°C or higher. In this case, a Tg of 110°C or higher is more preferable, and a Tg of 120°C or higher is particularly preferable. These resins can be obtained by known methods, such as copolymerizing the raw material monomers in the presence of a polymerization initiator, or by polymerizing and then converting the structure through a chemical reaction such as an addition reaction, a substitution reaction, or a redox reaction. Commercially available products can also be used.

[0238] <Additives> In addition to the light-emitting material and binder resin, the color-converting composition according to the embodiment of the present invention may contain other components (additives) as necessary, such as fillers, light stabilizers, antioxidants, processing and heat stabilizers, light resistance stabilizers such as UV absorbers, dispersants and leveling agents for stabilizing the coating film, scattering agents, plasticizers, crosslinking agents such as epoxy compounds, curing agents such as amines, acid anhydrides, and imidazoles, pigments, and adhesion aids such as silane coupling agents as film surface modifiers.

[0239] Examples of fillers include fine particles of fumed silica, glass powder, quartz powder, titanium oxide, zirconia oxide, barium titanate, zinc oxide, and silicone fine particles. Two or more of these may be contained.

[0240] Examples of light stabilizers include, but are not limited to, tertiary amines, catechol derivatives, complexes containing at least one transition metal selected from the group consisting of nickel (Ni), scandium (Sc), vanadium (V), manganese (Mn), iron (Fe), cobalt (Co), copper (Cu), yttrium (Y), zirconium (Zr), molybdenum (Mo), silver (Ag), and lanthanoids, and salts with organic acids. These light stabilizers may be used alone or in combination.

[0241] Examples of the antioxidant include, but are not limited to, phenolic antioxidants such as 2,6-di-tert-butyl-p-cresol and 2,6-di-tert-butyl-4-ethylphenol. These antioxidants may be used alone or in combination.

[0242] Examples of processing and heat stabilizers include, but are not limited to, phosphorus-based stabilizers such as tributyl phosphite, tricyclohexyl phosphite, triethyl phosphine, and diphenylbutyl phosphine. These stabilizers may be used alone or in combination.

[0243] Examples of the light resistance stabilizer include, but are not limited to, benzotriazoles such as 2-(5-methyl-2-hydroxyphenyl)benzotriazole and 2-[2-hydroxy-3,5-bis(α,α-dimethylbenzyl)phenyl]-2H-benzotriazole. These light resistance stabilizers may be used alone or in combination.

[0244] As the scattering particles, inorganic particles having a refractive index of 1.7 to 2.8 are preferred, and examples thereof include titania, zirconia, alumina, ceria, tin oxide, indium oxide, iron oxide, zinc oxide, aluminum nitride, aluminum, tin, titanium or zirconium sulfide, and titanium or zirconium hydroxide.

[0245] In the color-changing composition according to the embodiment of the present invention, the content of these additives can be set according to the size, thickness, and transmittance of the color-changing film to be produced. The content of the additives is 1.0×10 -3 It is preferable that the amount is 1.0×10 parts by weight or more. -2 It is more preferable that the amount is 1.0×10 parts by weight or more. -1 The content of these additives is preferably 30 parts by weight or less, more preferably 15 parts by weight or less, and even more preferably 10 parts by weight or less, relative to 100 parts by weight of the binder resin.

[0246] <Solvent> The color-changing composition according to the present invention may further contain a solvent. A solvent that can adjust the viscosity of the resin in a fluid state and that does not excessively affect the luminescence and durability of the luminescent material is preferred. Examples of solvents include water, 2-propanol, ethanol, toluene, methyl acetate, ethyl acetate, propyl acetate, butyl acetate, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, hexane, cyclohexane, tetrahydrofuran, acetone, terpineol, Texanol, 1,2-dimethoxyethane, methyl cellosolve, ethyl cellosolve, butyl carbitol, butyl carbitol acetate, 1-methoxy-2-propanol, and propylene glycol monomethyl ether acetate. Two or more of these solvents can also be mixed and used. Among these solvents, toluene, methyl ethyl ketone, methyl acetate, ethyl acetate, and tetrahydrofuran are preferred because they leave little residual solvent after drying.

[0247] From the viewpoint of further improving the durability of the color conversion film, the amount of solvent remaining in the color conversion layer after drying is preferably 3.0% by mass or less, more preferably 1.0% by mass or less, and even more preferably 0.5% by mass or less. The amount of solvent remaining in the color conversion layer can be measured by gas chromatography.

[0248] <Color conversion film> The color conversion film according to the embodiment of the present invention contains the color conversion composition described above or a cured product thereof. The shape of the color conversion film is not particularly limited, and examples thereof include layered, particulate, and fibrous forms. One aspect of the color conversion film according to the embodiment of the present invention is a color conversion sheet containing the color conversion composition or a color conversion layer formed by curing the color conversion composition.

[0249] When the color conversion film according to the embodiment of the present invention has multiple color conversion layers, the color conversion layers may be laminated directly or via an intermediate layer such as an adhesive layer.

[0250] The color conversion film according to the embodiment of the present invention may have a substrate or a barrier layer as needed, and may have two or more of these layers.

[0251] The substrate is not particularly limited, and known metals, films, glass, ceramics, paper, etc. can be used. Among these, glass and resin films are preferably used. As the resin film, films made of resins such as polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polyphenylene sulfide, polycarbonate, polypropylene, polyimide, aramid, and silicone are preferred. To facilitate peeling of the sheet, the surface of the substrate layer may be previously subjected to a release treatment. Similarly, to improve adhesion between layers, the surface of the substrate layer may be previously subjected to an easy-adhesion treatment.

[0252] When the substrate is in the form of a film, its thickness is not particularly limited, but the lower limit is preferably 12 μm or more, more preferably 38 μm or more, and the upper limit is preferably 5000 μm or less, more preferably 3000 μm or less.

[0253] Furthermore, members such as a barrier film, a light guide plate, a diffusion plate, a diffusion film, a prism sheet, a reflective polarizing film, a wavelength-selective reflection film, a wavelength-selective transmission film, and a wavelength-selective absorption film can also be used as the substrate.

[0254] The barrier layer is preferably one that prevents oxygen, moisture, heat, etc. from penetrating into the color conversion layer, and two or more barrier layers may be provided. A barrier layer may be provided on both sides or one side of the light conversion layer.

[0255] In one aspect of the color conversion film according to the embodiment of the present invention, the color conversion film preferably has an oxygen barrier layer. This is preferable because it can prevent the oxidative degradation of the light-emitting material caused by singlet oxygen generated by a dye-sensitization mechanism or the like. Furthermore, when the compound represented by general formula (1) emits delayed fluorescence, it exhibits significantly better durability than conventional organic light-emitting materials in the absence of oxygen, so it is more preferable for the color conversion film to have an oxygen barrier layer. This is because light-emitting materials that emit delayed fluorescence have a long life and can quickly convert a triplet excited state, which is prone to react with surrounding molecules, to a singlet excited state, making it less susceptible to degradation due to reactions between this triplet excited state and surrounding molecules.

[0256] Examples of oxygen barrier layers include inorganic oxides such as silicon oxide, aluminum oxide, titanium oxide, tantalum oxide, zinc oxide, tin oxide, indium oxide, yttrium oxide, and magnesium oxide, inorganic nitrides such as silicon nitride, aluminum nitride, titanium nitride, and silicon carbonitride, metal oxide thin films or metal nitride thin films obtained by adding other elements to these, and films containing various resins such as polyvinylidene chloride, acrylic resins, silicone resins, melamine resins, urethane resins, fluorine resins, and polyvinyl alcohol resins such as saponified vinyl acetate. Two or more of these may be used.

[0257] Representative structural examples of color conversion films according to embodiments of the present invention are shown in FIGS. 1 to 3. FIGS. 1 to 3 are schematic cross-sectional views showing examples of color conversion films according to embodiments of the present invention. As shown in FIG. 1, color conversion film 1, an example of this embodiment, has a structure in which three-dimensional structures 2 containing a compound represented by general formula (1) or a partial structure represented by general formula (7) are dispersed within support 3. As shown in FIG. 2, color conversion film 1A, an example of this embodiment, has a structure in which three-dimensional structures 2a containing a compound represented by general formula (1) or a partial structure represented by general formula (7) and three-dimensional structures 2b containing a compound represented by general formula (1) or a partial structure represented by general formula (7) are dispersed within support 3. As shown in FIG. 3, color conversion film 1B, an example of this embodiment, has a laminated structure in which support 3a, in which three-dimensional structures 2a containing a compound represented by general formula (1) or a partial structure represented by general formula (7) are dispersed, and support 3b, in which three-dimensional structures 2b containing a compound represented by general formula (1) or a partial structure represented by general formula (7) are dispersed within. Furthermore, the color conversion film according to the embodiment of the present invention may have a structure in which other three-dimensional structures or luminescent materials are contained within the support 3, 3a, or 3b in Figures 1 to 3, and it is preferable that other three-dimensional structures or luminescent materials are dispersed within the support 3, 3a, or 3b. The compound added to the color conversion film 1, 1A, or 1B preferably has a structure represented by general formula (1), more preferably a structure represented by general formula (5) or (6). Furthermore, the three-dimensional structure added to the color conversion film 1, 1A, or 1B preferably has a structure represented by general formula (7), more preferably a structure represented by general formula (8) or (9).

[0258] The color conversion film according to the embodiment of the present invention may further have an auxiliary layer having a light diffusion layer, an adhesive layer, an anti-reflection function, an anti-glare function, an anti-reflection and anti-glare function, a hard coat function (abrasion resistance function), an anti-static function, an anti-fouling function, an electromagnetic wave shielding function, an infrared ray blocking function, an ultraviolet ray blocking function, a polarizing function, a color-tuning function, or the like, depending on the required functions.

[0259] <Manufacturing method of color conversion film> The method for producing the color conversion film according to the embodiment of the present invention is not particularly limited as long as it can mold the color conversion composition according to the embodiment of the present invention into a desired shape. For example, a method can be used in which the color conversion composition is applied to a substrate and dried to form a color conversion layer. When the binder resin is a thermosetting resin, the color conversion composition can be applied to a base such as a substrate and then heat-cured to form a color conversion layer. When the binder resin is a photocurable resin, the color conversion composition can be applied to a substrate and then photocured to form a color conversion layer. Other examples include a method in which the color conversion composition is kneaded while heating and then molded using an extruder, and a method in which the color conversion composition is placed in a mold and molded by heating, cooling, drying, etc.

[0260] The application can be carried out using a reverse roll coater, blade coater, comma coater, slit die coater, direct gravure coater, offset gravure coater, kiss coater, natural roll coater, air knife coater, roll blade coater, two-stream coater, rod coater, wire bar coater, applicator, dip coater, curtain coater, spin coater, knife coater, etc., but is not limited to these.

[0261] The color conversion film can be dried using a common heating device such as a hot air dryer or an infrared dryer. In this case, the heating temperature is preferably 60 to 200°C, and the heating time is preferably 2 minutes to 4 hours. It is also possible to heat and cure the film in stages using a method such as step curing.

[0262] When the color conversion layer is formed by heat curing, a hot air oven or the like can be used as the heating device. The heating conditions can be selected depending on the binder resin. For example, the heating temperature is preferably 100°C to 300°C, and the heating time is preferably 1 minute to 2 hours.

[0263] When forming a color conversion layer by photocuring, it is preferable to irradiate with high-energy light such as ultraviolet light. The light irradiation conditions can be selected depending on the binder resin. For example, the wavelength of the irradiated light is preferably 200 nm to 500 nm, and the irradiation dose is 10 mJ / cm. 2 ~10J / cm 2 is preferred.

[0264] After the color conversion layer is produced, the substrate can be changed as needed. In this case, simple methods include a method of replacing the substrate using a hot plate, or a method using a vacuum laminator or a dry film laminator.

[0265] <Light source unit> A light source unit according to an embodiment of the present invention is configured to include at least a light source and the above-described color conversion composition or color conversion film. When the light source unit of the present invention includes a color conversion composition, the arrangement of the light source and the color conversion composition is not particularly limited. The color conversion composition may be applied directly to the light source, or the color conversion composition may be applied to a film or glass separated from the light source. When the light source unit of the present invention includes a color conversion film, the arrangement of the light source and the color conversion film is not particularly limited. The light source and the color conversion film may be in close contact with each other, or a remote phosphor type in which the light source and the color conversion film are separated from each other may be used. Furthermore, a color filter may be further included to increase color purity, and optical components such as a prism sheet, a reflective polarizing film, or a diffusion film may be included to improve brightness and uniformity of emitted light.

[0266] One aspect of the light source unit according to the embodiment of the present invention includes a color conversion film having any of the configurations shown in Figures 1 to 3, with a light source located below the color conversion film and a prism sheet and a reflective polarizing film stacked above the color conversion film. A diffusion plate may be provided between the light source and the color conversion film, and a reflector may be provided below the light source.

[0267] Another aspect of the light source unit according to the embodiment of the present invention is a configuration in which a light source and a light guide plate are provided, and a color conversion layer formed by directly applying a color conversion composition is laminated on the light output side of the light guide plate. A light diffusion layer or a wavelength selective transmission layer may be further formed on the color conversion layer.

[0268] The light source unit of the present invention is useful for various light sources such as spatial lighting and backlighting, and specifically can be used for applications such as displays, lighting, interiors, signs, and billboards, but is particularly suitable for use in displays and lighting.

[0269] <Light source> Any light source can be used as long as it emits light in a wavelength range that can be absorbed by the light-emitting material used in the present invention. For example, any light source can in principle be used, such as a hot cathode tube, a cold cathode tube, a fluorescent light source such as an inorganic EL, an organic electroluminescence element light source, an LED light source, an incandescent light source, or sunlight. Among these, an LED or an organic electroluminescence element is preferred in terms of color purity, and an LED is more preferred.

[0270] For display and lighting applications, a light source having a maximum emission wavelength in the range of 430 nm to 500 nm is preferred because it can enhance the color purity of blue light. Furthermore, a blue LED having a maximum emission wavelength in the range of 430 nm to 480 nm is more preferred, and a blue LED having a maximum emission wavelength in the range of 445 nm to 470 nm is even more preferred.

[0271] The light source may have one emission peak or two or more emission peaks, but in order to improve color purity, it is preferable to have one emission peak. It is also possible to use any combination of multiple light sources with different emission peaks.

[0272] <Displays, lighting equipment> A display according to an embodiment of the present invention includes at least a light source unit including a light source and a color-converting material composition or a color-converting film as described above. For example, in a display such as a liquid crystal display, the light source unit described above is used as a backlight unit.

[0273] Furthermore, an illumination device according to an embodiment of the present invention includes at least a light source unit including a light source and a color conversion material composition or a color conversion film as described above. For example, this illumination device is configured to emit white light by combining a blue LED light source as the light source unit with a color conversion material composition or a color conversion film that converts blue light from the blue LED light source to light with a longer wavelength. [Example]

[0274] The present invention will be described below with reference to examples, but the present invention is not limited to these examples.

[0275] <Light-emitting materials> (compound) In the following examples and comparative examples, compounds G-1 to G-4, G-101, and G-102 are the compounds shown below.

[0276] [ka]

[0277] (Synthesis Example 1) [Synthesis of Intermediate 1A] 3,5-Dibromobenzaldehyde (13.2 g), 2,4-dimethylpyrrole (10.0 g), and toluene (330 mL) were added to a 1000 mL recovery flask and cooled to 0°C while stirring. Then, trifluoroacetic acid (0.80 g) diluted in 10 mL of toluene was added over 5 minutes, and the mixture was stirred at 0°C for 3 hours. After completion of the reaction, water was added to the flask to stop the reaction, and the organic layer was separated and extracted. The solvent was removed using an evaporator, and the residue was purified using a silica gel column to obtain Intermediate 1A.

[0278] [Synthesis of Intermediate 2A] Intermediate 1A (23.4 g) and dichloromethane (450 mL) were added to a 1000 mL recovery flask and cooled to 0°C with stirring. 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (13.6 g) was then added over 10 minutes and stirred at 0°C for 4 hours. After the reaction was complete, boron trifluoride diethyl ether complex (40 mL) and diisopropylethylamine (25 mL) were added and stirred for 4 hours. Water was then added to quench the reaction. The solid components in the reaction solution were removed by filtration through Celite. Water was added to the filtrate, and the organic layer was separated. This organic layer was dried over magnesium sulfate, filtered, and the solvent was removed using an evaporator. The resulting reaction product was washed with methanol to obtain Intermediate 2A.

[0279] [Synthesis of Intermediate 3A] Intermediate 2A (2.8 g), 4-vinylphenylboronic acid (1.9 g), bis(triphenylphosphine)palladium(II) dichloride (0.16 g), sodium carbonate (2.6 g), 1,2-dimethoxyethane (40 mL), and water (15 mL) were added to a 200 mL recovery flask and stirred at 80°C for 4 hours in a nitrogen atmosphere. After completion of the reaction, the solid components in the reaction solution were removed by filtration through Celite, and ethyl acetate and water were added to the filtrate to separate the organic layer. The solvent in the organic layer was removed using an evaporator, and the residue was purified using a silica gel column to obtain Intermediate 3A.

[0280] [Synthesis of G-1] Intermediate 3A (1.0 g), triethoxysilane (0.93 g), and toluene (7 mL) were added to a 100 mL recovery flask and stirred at room temperature. Two drops of platinum(0)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex solution (Pt ~ 2%, xylene solution) were added, and the mixture was stirred at 70 °C for 3 hours under a nitrogen atmosphere. After the reaction was completed, the solvent was removed using an evaporator and the residue was purified using a silica gel column to obtain G-1.

[0281] [ka]

[0282] (Synthesis Example 2) [Synthesis of Intermediate 3B] Intermediate 3B was obtained in the same manner as in Synthesis Example 1, except that 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol was used instead of 4-vinylphenylboronic acid used in the synthesis of Intermediate 3A.

[0283] [Synthesis of Intermediate 4B] Intermediate 3B (2.1 g), allyl bromide (2.0 g), potassium carbonate (2.3 g), and acetone (40 mL) were added to a 200 mL recovery flask and stirred at 60°C under a nitrogen atmosphere for 3 hours. After the reaction was completed, the solvent was removed using an evaporator, ethyl acetate and water were added to the flask, and the organic layer was separated. The extracted organic layer was washed with water and the solvent was removed again using an evaporator. The mixture was purified using a silica gel column to obtain Intermediate 4B.

[0284] [Synthesis of G-2] G-2 was synthesized in the same manner as in Synthesis Example 1, except that intermediate 3A in the synthesis of G-1 was changed to intermediate 4B.

[0285] [ka]

[0286] (Synthesis Example 3) [Synthesis of G-3] G-3 was synthesized in the same manner as in Synthesis Example 2, except that in the synthesis of G-2, the starting material 2,4-dimethylpyrrole was changed to 3-ethyl-2,4-dimethylpyrrole.

[0287] (Synthesis Example 4) [Synthesis of G-4] G-4 was synthesized in the same manner as in Synthesis Example 2, except that triethoxysilane in the synthesis of G-2 was changed to diethoxymethylsilane.

[0288] Compounds G-101 and G-102 other than those described above were synthesized with reference to JP-A-2020-500325 and Inorganic Chemistry, 2011, 50, 9201-9203, respectively.

[0289] Tables 1 and 2 show the yield of the hydrosilylation reaction, which is the final step of the synthesis, for each luminescent material.

[0290] (3D structure) The methods for producing the three-dimensional structures PG-1 to PG-4, PG-1-2 to PG-4-2, PG-101 to PG-102, and PG-101-2 to PG-102-2 in the following examples and comparative examples are shown below.

[0291] [Production Example 1] (Fabrication of three-dimensional structure PG-1 (when element M is Si)) A reaction solution was prepared by adding 30 mL of ethanol, 3.2 mL of water, and 0.4 mL of 28% aqueous ammonia to a 200 mL three-neck flask and stirring at room temperature. Next, a 0.04 mol / L ethanol solution of G-1 was prepared by dissolving 6.5 mg of compound G-1 in 5.8 mL of ethanol and slowly adding it to the reaction solution. While vigorously stirring the reaction solution, 1.4 mL of TEOS was slowly added and the mixture was stirred at room temperature for 2 hours. Then, 0.7 mL of TEOS was added three times every 2 hours. Two hours after the third addition, 27 mL of TEOS and 3.8 mL of 28% aqueous ammonia were slowly added and the mixture was stirred overnight at room temperature. The particles were collected from the resulting suspension by filtration, washed with ethyl acetate and ethanol, and dried in a vacuum oven at 60 °C for 5 hours to obtain the three-dimensional structure PG-1.

[0292] The other three-dimensional structures PG-2 to PG-4, PG-101, and PG-102 were also prepared in the same manner as above, except that compound G-1 was replaced with G-2 to G-4, G-101, and G-102, respectively, and the concentration of the luminescent material relative to TEOS was adjusted to 0.05 mol%.

[0293] (Fabrication of three-dimensional structure PG-1-2 (when element M is Ti)) 20 mL of ethanol and 10 mL of tetraisoproxi titanate were added to a 300 mL three-neck flask and stirred at room temperature for 15 minutes. Next, a 0.04 mol / L ethanol solution of G-1 was prepared by dissolving 6.5 mg of compound G-1 in 5.8 mL of ethanol. This solution was slowly added to the reaction solution and stirred at room temperature for an additional 30 minutes. In a separate 200 mL beaker, 50 mL of ethanol, 10 mL of water, and 1 mL of concentrated hydrochloric acid were added and stirred at room temperature for 15 minutes to prepare ethanolic hydrochloric acid. The prepared ethanolic hydrochloric acid was slowly added to the reaction solution and stirred at room temperature for 1 hour. The particles were collected from the resulting suspension by filtration, washed with ethyl acetate and ethanol, and dried in an oven at 180 °C for 5 hours to obtain the three-dimensional structure P-G1-2.

[0294] The other three-dimensional structures PG-2-2 to PG-4-2, PG-101-2, and PG-102-2 were also prepared in the same manner as above, except that compound G-1 was replaced with G-2 to G-4, G-101, and G-102, respectively, and the concentration of the ethanol solution of the luminescent material was adjusted to 0.04 mol%.

[0295] <Calculation of compound incorporation rate into three-dimensional structures> The absorption spectra of the reaction solution before and after the addition of TEOS or tetraisoproxy titanate were measured, and the amount of compound incorporated into the three-dimensional structure was estimated from the ratio of absorbance at the absorption maximum wavelength based on the following equation. It was assumed that all of the TEOS or tetraisoproxy titanate was hydrolyzed, and that 4 equivalents of ethanol were produced relative to TEOS, and 4 equivalents of 2-propanol were produced relative to tetraisoproxy titanate. The absorbance was corrected to account for the dilution of the concentration of the filtrate after the reaction by the volume of the ethanol and 2-propanol produced.

[0296] Incorporation rate of compounds into 3D structures = (absorbance at the maximum absorption wavelength of the filtrate after the reaction) / (absorbance at the absorption maximum wavelength of the reaction solution before adding TEOS or tetraisoproxil titanate) × 100 The absorption spectrum was measured using a Hitachi U-3200 spectrophotometer, and the reaction solution and filtrate were diluted 10 times with ethanol before measurement.

[0297] <Scatter material> Titanium dioxide particles JR-301 (manufactured by Teika Co., Ltd.) were used as scattering materials. Next, the evaluation methods used in the examples will be described.

[0298] <Measurement of Emission Spectrum> Each color conversion sheet and prism sheet was placed on a surface light-emitting device equipped with a blue LED element with an emission peak wavelength of 450 nm. A current of 10 mA was passed through the surface light-emitting device to light up the blue LED element, and the emission spectrum was measured using a spectroradiometer (CS-1000, manufactured by Konica Minolta).

[0299] <Light durability evaluation> A light-emitting device equipped with the color conversion film and blue LED (USHIO EPITEX; model number SMBB450H-1100, peak emission wavelength: 450 nm) prepared in each example and comparative example was run through it. A current of 100 mA was passed through the device to lighten the blue LED, and the initial peak emission intensity was measured using a spectroradiometer (Konica Minolta CS-1000). The distance between the color conversion film and the blue LED element was 3 cm. The color conversion film was then continuously irradiated with light from the blue LED element in an environment of 50°C, and the light durability of the color conversion film was evaluated by observing the time until the peak emission intensity decreased by 5%.

[0300] Example 1 An acrylic resin was used as the binder resin, and 100 parts by weight of the binder resin were mixed with 5 parts by weight of the three-dimensional structure PG-1 as the luminescent material, 0.5 parts by weight of JR-301 as the scattering material, and 300 parts by weight of ethyl acetate as the solvent.The mixture was then stirred and degassed at 1000 rpm for 20 minutes using a planetary stirring and degassing device "Mazerustar" (registered trademark) KK-400 (manufactured by Kurabo Industries, Ltd.) to obtain a resin composition for producing a color conversion layer.

[0301] Next, the resin liquid for preparing the color conversion layer was applied using a film applicator onto the substrate layer, "Lumirror" (registered trademark) U48 (manufactured by Toray Industries, Inc., thickness 50 μm), and heated at 100°C for 20 minutes and dried to form a color conversion layer with an average thickness of 17 μm, thereby obtaining a color conversion film.

[0302] When blue LED light was converted using this color conversion film, high-color-purity green light was obtained with a peak wavelength of 520 nm and a half-width of the emission spectrum at the peak wavelength of 32 nm, when only the green light emission region was extracted. Furthermore, when light from a blue LED element was continuously irradiated in an environment of 50°C, the time until the emission peak intensity decreased by 5% was 750 hours, which was about 7.5 times better than Comparative Example 1 described below and about 19 times better than Comparative Example 2.

[0303] Examples 2 to 8 A color conversion film was produced in the same manner as in Example 1, except that the three-dimensional structure was changed to one shown in Tables 1 and 2. The results are shown in Tables 1 and 2.

[0304] Comparative Examples 1 to 4 A color conversion film was produced in the same manner as in Example 1, except that the three-dimensional structure was changed to one shown in Tables 1 and 2. The results are shown in Tables 1 and 2.

[0305] In Examples 1 to 8, light emission with a narrow half-width in the wavelength range of 515 to 540 nm was obtained, and the light durability was also excellent, so that a color conversion film was provided which achieved both high color purity light emission and durability.On the other hand, in Comparative Examples 1 to 4, high color purity light emission with a half-width of 40 nm or less was exhibited, but light durability was poor.

[0306] [Table 1]

[0307] [Table 2]

[0308] Furthermore, when looking at the hydrosilylation yield of each compound, G-4, in which the reactive site with the three-dimensional structure is a dialkoxysilyl group, has a high yield, while compounds other than G-4, in which the reactive site with the three-dimensional structure is a trialkoxysilyl group, have low yields, indicating that dialkoxysilyl groups have a superior hydrosilylation reaction yield. On the other hand, the incorporation rate of the compound into the three-dimensional structure is superior for trialkoxysilyl groups due to the greater number of reactive sites, and the more reactive sites required for bonding to the three-dimensional structure, the higher the incorporation rate. Although compound G-4 of Example 4, which has a dialkoxysilyl group, is inferior to compounds G-1 to G-3 of Examples 1 to 3, which have trialkoxysilyl groups, in terms of the incorporation rate of the compound into the three-dimensional structure, PG-4, in which the element M is Si, has excellent optical properties and high light durability similar to PG-1 to PG-3, and this is also true for the three-dimensional structure PG-4-2, in which the element M is Ti. These results indicate that by using a three-dimensional structure incorporating a compound having a dialkoxysilyl group or a trialkoxysilyl group, it is possible to obtain a color conversion film that combines high color purity luminescence with durability.

[0309] Furthermore, when comparing the cases where element M is Si and Ti, it is clear that the compound incorporation rate into the 3D structure is higher when element M is Si than when it is Ti. This is thought to be because the condensation reaction between titanium alkoxides is faster than the condensation reaction between the compound and titanium alkoxide, making it difficult for the compound to be incorporated into the 3D structure. Furthermore, when focusing on light durability, it is clear that element M is Si than when it is Ti. When element M is Ti, the 3D structure obtained by filtration needs to be fired at a high temperature of 250-300°C. However, due to concerns about degradation of the luminescent material, it was fired at 180°C. This is thought to be because the -Ti-O-Ti- network formation was not successful, and -O-Ti-OH moieties were partially present in the 3D structure, resulting in a sparse 3D structure. On the other hand, whether element M is Si or Ti, both the compound incorporation rate and light durability were superior to the 3D structure of the comparative example. It is clear that the 3D structure composed of compounds G-1 to G-4 allows for the production of a color conversion film that combines high color purity luminescence with durability. [Explanation of symbols]

[0310] 1, 1A, 1B color conversion film 2, 2a, 2b Compounds or 3D structures 3, 3a, 3b Support

Claims

1. A compound represented by the following general formula (1): 【Chemistry 1】 (R １ ~R ６ and R １１ ~R １５ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted alkynyl group, a hydroxyl group, a thiol group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted aryl ether group, a substituted or unsubstituted aryl thioether group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a halogen atom, a cyano group, an aldehyde group, a substituted or unsubstituted carbonyl group, a carboxyl group, a methyl ... and n is 0 or 1. The substituent is selected from the group consisting of a carboxyl group, a substituted or unsubstituted oxycarbonyl group, a substituted or unsubstituted carbamoyl group, a substituted or unsubstituted ester group, a substituted or unsubstituted amido group, a substituted or unsubstituted acyl group, a substituted or unsubstituted sulfonyl group, a substituted or unsubstituted sulfonate ester group, a substituted or unsubstituted sulfonamido group, an amino group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkoxysilyl group, a substituted or unsubstituted silanol group, a substituted or unsubstituted siloxanyl group, a substituted or unsubstituted boryl group, and a substituted or unsubstituted phosphine oxide group. R ７ and R ８ are each independently selected from the group consisting of a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted alkynyl group, a hydroxyl group, a thiol group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted aryl ether group, a substituted or unsubstituted aryl thioether group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a halogen atom, and a cyano group. However, R １ ~R ８ and R １１ ~R １５ At least one of the above contains a structure represented by the following general formula (2). 【Chemistry 2】 L １ represents a single bond, an oxygen atom, a sulfur atom, a carbonyl group, —C(═O)O—, —OC(═O)—, or —SiR ｃ R ｄ - is. L ２ is a substituted or unsubstituted alkylene group, a substituted or unsubstituted alkyleneoxy group, a substituted or unsubstituted alkylenethio group, a substituted or unsubstituted cycloalkylene group, a substituted or unsubstituted arylene group, a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted heteroarylene group. R ａ is a hydrogen atom or a linear or branched alkyl group, and R ｂ is a hydrogen atom, a halogen, a linear or branched alkyl group, a substituted or unsubstituted cycloalkyl group, or a substituted or unsubstituted aryl group. R ｃ and R ｄ are each independently selected from the group consisting of a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkoxysilyl group, and a silanol group, and n is an integer of 1 to 3. However, the compound represented by general formula (1) satisfies either the following (A) or (B): (A)R １１ ~R １５ At least one of the groups is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. (B) R ２ and R ５ is a hydrogen atom.)

2. The compound represented by general formula (1) satisfies (A), and R １１ ~R １５ The compound according to claim 1, wherein at least two of the groups are substituted or unsubstituted aryl groups or substituted or unsubstituted heteroaryl groups.

3. The compound according to claim 1 or 2, wherein the compound represented by general formula (1) satisfies (A) and is a compound represented by general formula (3) or (4). 【Transformation 3】 (In general formula (3) or (4), R １ ~R ８ and R １１ ~R １５ The definition of R is the same as in general formula (1). ２１ ~R ４０ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted alkynyl group, a hydroxyl group, a thiol group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted aryl ether group, a substituted or unsubstituted aryl thioether group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a halogen atom, a cyano group, an aldehyde group, a substituted or unsubstituted carbonyl group, a carboxyl group, a methyl ... and n is 0 or 1. The substituent is selected from the group consisting of a carboxyl group, a substituted or unsubstituted oxycarbonyl group, a substituted or unsubstituted carbamoyl group, a substituted or unsubstituted ester group, a substituted or unsubstituted amido group, a substituted or unsubstituted acyl group, a substituted or unsubstituted sulfonyl group, a substituted or unsubstituted sulfonate ester group, a substituted or unsubstituted sulfonamido group, an amino group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkoxysilyl group, a substituted or unsubstituted silanol group, a substituted or unsubstituted siloxanyl group, a substituted or unsubstituted boryl group, and a substituted or unsubstituted phosphine oxide group. However, in the general formula (3), R １１ , R １３ , R １５ and R ２１ ~R ３０ At least one of the formulas (1) and (2) contains a structure represented by general formula (2), and in general formula (4), R １２ ~R １４ and R ３１ ~R ４０ At least one of the above contains a structure represented by general formula (2).

4. In general formula (3), R １１ , R １３ , R １５ and R ２１ ~R ３０ At least two of the general formula (4) contain a structure represented by general formula (2), and in general formula (4), R １２ ~R １４ and R ３１ ~R ４０ The compound according to claim 3, wherein at least two of the above formulas contain a structure represented by general formula (2).

5. The compound according to claim 3, wherein the compound represented by general formula (3) is a compound represented by general formula (5), and the compound represented by general formula (4) is a compound represented by general formula (6). 【Chemistry 4】 (L in general formula (5) or general formula (6) １ , L ２ , R １ ~R ８ , R １１ ~R １５ , R ３１ ~R ４０ , R a , R ｂ and n is defined as in general formula (2), general formula (3), or general formula (4).

6. In the general formula (5) or (6), R ２ and R ５ are each independently selected from the group consisting of a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a halogen atom, and a substituted or unsubstituted silyl group.

7. In the general formula (5) or (6), R ２ and R ５ The compound according to claim 5 , wherein is a hydrogen atom.

8. The compound represented by general formula (1) satisfies (B), and R １１ ~R １５ and at least one of the groups is a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, or a halogen atom.

9. The compound represented by general formula (1) satisfies (B), and R １１ ~R １５ The compound according to claim 1 , wherein at least one of

10. The compound represented by general formula (1) satisfies (B), and R １１ ~R １５ The compound according to claim 1 , wherein at least two of

11. The compound represented by the general formula (1) satisfies (B), and R １１ and R １５ , or R １２ and R １４ The compound according to claim 1 , wherein is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group.

12. In the partial structure represented by general formula (2), L １ represents a single bond, an oxygen atom, a carbonyl group, —C(═O)O—, —OC(═O)—, or —SiR ｃ R ｄ - is selected from a candidate group consisting of L ２ The compound according to claim 1 , 2 or 8 , wherein: is a substituted or unsubstituted alkylene group or a substituted or unsubstituted alkyleneoxy group; and n is 2 or 3.

13. The compound according to claim 1, wherein the compound represented by the general formula (1) emits light with a peak wavelength observed in the region of 500 nm or more and 580 nm or less when excited with light.

14. A color-changing composition that converts incident light into light with a longer wavelength than the incident light, comprising the compound according to claim 1 and a binder resin.

15. A three-dimensional structure formed by a covalent bond between an element M and an oxygen atom, wherein the element M is an element selected from the group consisting of Si, Ti, and Al, and the three-dimensional structure includes a partial structure represented by general formula (7). 【Transformation 5】 (In general formula (7), " represents a bonding point to the three-dimensional structure. R １０１ ~R １０６ and R １１１ ~R １１５ are each independently L ３ or a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted alkynyl group, a hydroxyl group, a thiol group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted aryl ether group, a substituted or unsubstituted aryl thioether group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a halogen atom, a cyano group, an aldehyde group, a substituted or unsubstituted carbonyl group, It is selected from the group consisting of a carboxyl group, a substituted or unsubstituted oxycarbonyl group, a substituted or unsubstituted carbamoyl group, a substituted or unsubstituted ester group, a substituted or unsubstituted amide group, a substituted or unsubstituted acyl group, a substituted or unsubstituted sulfonyl group, a substituted or unsubstituted sulfonate ester group, a substituted or unsubstituted sulfonamide group, an amino group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkoxysilyl group, a substituted or unsubstituted silanol group, a substituted or unsubstituted siloxanyl group, a substituted or unsubstituted boryl group, and a substituted or unsubstituted phosphine oxide group. R １０７ and R １０８ are each independently L ３ or is selected from the group consisting of a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted alkynyl group, a hydroxyl group, a thiol group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted aryl ether group, a substituted or unsubstituted aryl thioether group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a halogen, and a cyano group. However, R １０１ ~R １０８ and R １１１ ~R １１５ At least one of ３ or a single bond bonding to L ３ has a substituent that bonds to L ３ represents a single bond, an oxygen atom, a sulfur atom, a carbonyl group, —C(═O)O—, —OC(═O)—, or —SiR ｆ R ｇ - is. ４ is a substituted or unsubstituted alkylene group, a substituted or unsubstituted alkyleneoxy group, a substituted or unsubstituted alkylenethio group, a substituted or unsubstituted cycloalkylene group, a substituted or unsubstituted arylene group, a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted heteroarylene group. However, R ｆ and R ｇ are each independently selected from the group consisting of a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkoxysilyl group, and a silanol group. R ｅ is selected from the group consisting of a hydrogen atom, a halogen atom, a linear or branched alkyl group, a substituted or unsubstituted cycloalkyl group, and a substituted or unsubstituted aryl group. m is an integer of 1 to 3. However, the partial structure represented by the general formula (7) satisfies either the following (C) or (D). (C)R １１１ ~R １１５ At least one of the groups is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. (D)R １０２ and R １０５ is a hydrogen atom.

16. In the partial structure represented by general formula (7), L ３ represents a single bond, an oxygen atom, a sulfur atom, a carbonyl group, —C(═O)O—, —OC(═O)—, or —SiR ｆ R ｇ - and L ４ The three-dimensional structure according to claim 15, wherein m is a substituted or unsubstituted alkylene group or a substituted or unsubstituted alkyleneoxy group, and m is 2 or 3.

17. The three-dimensional structure according to claim 16, wherein the partial structure represented by general formula (7) is a partial structure represented by general formula (8) or (9). 【Transformation 6】 【Transformation 7】 In the general formulae (8) and (9), the symbol "-" represents a bonding point to the three-dimensional structure. R １０２ and R １０５ is a hydrogen atom. R １０１ , R １０３ , R １０４ , R １０６ , R １１１ ~R １１５ and R １３１ ~R １４０ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted alkynyl group, a hydroxyl group, a thiol group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted aryl ether group, a substituted or unsubstituted aryl thioether group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a halogen atom, a cyano group, an aldehyde group, a substituted or unsubstituted carbonyl group, a carboxyl group, a methyl ... and n is 0 or 1. The substituent is selected from the group consisting of a carboxyl group, a substituted or unsubstituted oxycarbonyl group, a substituted or unsubstituted carbamoyl group, a substituted or unsubstituted ester group, a substituted or unsubstituted amido group, a substituted or unsubstituted acyl group, a substituted or unsubstituted sulfonyl group, a substituted or unsubstituted sulfonate ester group, a substituted or unsubstituted sulfonamido group, an amino group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkoxysilyl group, a substituted or unsubstituted silanol group, a substituted or unsubstituted siloxanyl group, a substituted or unsubstituted boryl group, and a substituted or unsubstituted phosphine oxide group. R １０７ and R １０８ are each independently selected from the group consisting of a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted alkynyl group, a hydroxyl group, a thiol group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted aryl ether group, a substituted or unsubstituted aryl thioether group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a halogen atom, and a cyano group.

18. The three-dimensional structure according to claim 15, wherein the element M is Si.

19. The three-dimensional structure according to claim 15, wherein the element M is Ti.

20. A color-changing composition that converts incident light into light with a longer wavelength than the incident light, the color-changing composition comprising the three-dimensional structure according to claim 15 and a binder resin.

21. The color-changing composition of claim 20 , wherein the three-dimensional structures are particulate.

22. A color-changing film comprising a layer comprising the color-changing composition according to claim 14 or 20, or a cured product thereof.

23. A light source unit comprising a light source and the color conversion film according to claim 22.

24. 24. The light source unit according to claim 23, wherein the light source is a light emitting diode having a maximum emission wavelength in the range of 430 nm to 500 nm.

25. A display comprising the color conversion film according to claim 23.

26. A lighting device comprising the color conversion film according to claim 23.

Images