Polymer microparticles, method for producing same, composition, optical member, light source unit, display, illumination device, and ink

Abstract

Polymer microparticles according to one embodiment of the present invention contain a resin as a main component and contain a light-emitting material or a coloring material. The polymer microparticles have a true sphericity of from 80 to 100 (inclusive). In the polymer microparticles, the resin has, in the molecular structure thereof, at least one ring structure selected from the group consisting of aliphatic hydrocarbon rings, aliphatic heterocyclic rings, and SP3-carbon-containing rings.

Description

Technical Field

[0001] The present invention relates to polymer microparticles and a method for producing the same, a composition and an optical component containing the same, and a light source unit, a display, a lighting device, and ink produced using the same. Background Art

[0002] Polymer microparticles are particles formed from polymers, typically ranging in diameter from tens of nanometers to hundreds of micrometers. Unlike polymer molded products such as films, fibers, injection molded products, and extruded products, polymer microparticles are used to modify and improve various materials by utilizing their large specific surface area and microparticle shape. Major uses for polymer microparticles include cosmetic modifiers, toner additives, optical applications such as light diffusion and light absorption, rheology modifiers for coatings, medical diagnostic test agents, additives for molded products such as automotive materials and building materials, and powder raw materials for 3D printers.

[0003] As the general manufacture method of polymer particles in the past, can be roughly classified into the bottom-up process and mechanical crushing, dissolution-extraction method etc. that take free radical polymerization as representative.As representational bottom-up process, can enumerate the free radical polymerization method (for example, referring to patent documentation 1) of vinyl polymers such as emulsion polymerization.The method that is used simply as representational top-down process is mechanical crushing method, dissolution-extraction method.Mechanical crushing method utilizes liquid nitrogen etc. to make the method for freezing and mechanically pulverizing of resin pellets etc..Dissolution-extraction method makes resin dissolution in the solvent, removes etc. by cooling, solvent and makes the solubility of this resin reduce, makes this resin be separated out and obtain the method for particulate (for example, referring to patent documentation 2) with particle shape thus.

[0004] In addition, polymer microparticles containing luminescent materials and coloring materials are being studied for use as markers for biological observation and optical components. A method for producing these polymer microparticles has been reported in which a mixture of a luminescent material and an acrylic resin is granulated using a spray drying method (e.g., see Patent Document 3).

[0005] Prior art literature

[0006] Patent Literature

[0007] Patent Document 1: Japanese Patent Application Laid-Open No. 7-133328

[0008] Patent Document 2: Japanese Patent Application Laid-Open No. 2005-054153

[0009] Patent Document 3: International Publication No. 2020 / 050144 Summary of the Invention

[0010] However, the resins studied in the bottom-up process described in Patent Document 1 are limited to certain vinyl polymers made from acrylic resins, styrene, and the like, resulting in limitations in obtaining polymer microparticles from desired resins suitable for optical applications. Furthermore, since the polymer is produced by polymerizing emulsified monomers, residual emulsifiers, polymerization initiators, and their deteriorated forms are unavoidable in the polymer microparticles after polymerization. This poses a challenge to changes in optical properties, such as coloration, caused by trace impurities during long-term use in optical applications.

[0011] On the other hand, if for top-down process, then owing to the resin with desired characteristic being processed into particle shape, therefore have the resin that can obtain the such advantage of polymer particles with optical performance excellence.In addition, owing to can directly the high-purity resin after the purification be carried out particleization, therefore also have advantage from the viewpoint that prevents trace impurities from remaining in the polymer particles.But in this mode, mechanical pulverization method need make the resin freezing, therefore have following problem: consume energy cost, and the obtained crushed material becomes amorphous shape usually.In addition, even be to put down in writing such dissolution and precipitation method among the patent documentation 2, except that obtained particulate becomes the such problem of amorphous shape usually, also exist because of these particulate become porous etc. reasons and make the such problem that the specific surface area of ​​these particulate becomes large.

[0012] In addition, in recent years, the illumination required by light sources for optical applications has increased, and the degradation of components containing luminescent materials and coloring materials has become a problem. The above-mentioned patent document 3 does disclose a technology for suppressing the spread of highly active species and the accelerated degradation of the entire component by micronizing a polymer. However, for the rapid increase in the illumination intensity of light sources, the existing technology still cannot fully solve this problem. Specifically, the design technology related to the composition and shape of polymer particles is insufficient. For example, according to the technology disclosed in the above-mentioned patent document 3, polymer particles containing luminescent materials and coloring materials can indeed be produced, but the optimization of the resin constituting the polymer particles is insufficient. In addition, since the particle shape of the obtained particles becomes amorphous, there is a problem of causing optical loss and promoting degradation.

[0013] The present invention aims to simultaneously improve the durability and reduce optical loss in polymer microparticles containing a luminescent material and a coloring material. In particular, the present invention was developed in light of these circumstances and aims to provide polymer microparticles composed of a resin suitable for long-term use in high-intensity optical applications, exhibiting high sphericity, uniformity, and excellent isotropy.

[0014] Means for solving problems

[0015] In order to solve the above-mentioned problems and achieve the purpose, the present invention adopts the structure described in any one of the following [1] to

[25] .

[0016] That is, the polymer microparticles according to the present invention [1] are polymer microparticles having a resin as a main component and containing a luminescent material or a coloring material, characterized in that the sphericity of the polymer microparticles is 80 or more and 100 or less, and the resin is a resin having at least one ring structure selected from the group consisting of an aliphatic hydrocarbon ring, an aliphatic heterocycle and a ring containing sp3 carbon in its molecular structure.

[0017] Furthermore, the polymer microparticles according to the present invention, [2] in the invention described in [1] above, are characterized in that the linseed oil absorption is from 1 mL / 100 g to 200 mL / 100 g.

[0018] In addition, regarding the polymer microparticles according to the present invention, [3] in the invention described in [1] or [2] above, it is characterized in that the ratio of D90 particle size to D10 particle size in the particle size distribution of the polymer microparticles, i.e., D90 particle size / D10 particle size, is 1 to 5.

[0019] [4] The polymer microparticles according to the present invention, in the invention described in any one of [1] to [3] above, are characterized in that the content of the solvent in the polymer microparticles is less than 1 wt%.

[0020] Furthermore, regarding the polymer microparticles according to the present invention, [5] in the invention described in any one of [1] to [4] above, the content of the polymerization initiator and its decomposition product in the polymer microparticles is less than 0.1 wt%.

[0021] [6] The polymer microparticles according to the present invention, in the invention described in any one of [1] to [5], are characterized in that the glass transition temperature of the resin is 100° C. or higher.

[0022] In addition, with respect to the polymer microparticles according to the present invention, [7] in the invention described in any one of [1] to [6] above, the resin is at least one of a resin having the ring structure in the polymer main chain and a resin in which the ring structure is directly connected to the polymer main chain.

[0023] In addition, regarding the polymer microparticles according to the present invention, [8] in the invention described in any one of [1] to [7] above, it is characterized in that the resin has a partial structure represented by the general formula (1) and a partial structure represented by the general formula (2) in its molecular structure.

[0024] [Chemical Formula 1]

[0025]

[0026] (In general formula (1), Y 1 and Y 2 They may be the same or different and are hydrogen atoms or organic groups having 1 to 20 carbon atoms. 3 ~Y 6 They may be the same or different and are hydrogen atoms or organic groups having 1 to 20 carbon atoms, and Y 3 ~Y 6 At least one of them is a group containing an aliphatic cyclic hydrocarbon structure.

[0027] Furthermore, regarding the polymer microparticles according to the present invention, [9] in the invention described in [8] above, it is characterized in that Y 3 ~Y 6 At least one of them is a substituted or unsubstituted cyclohexyl group.

[0028] Furthermore, regarding the polymer microparticles according to the present invention,

[10] in the invention described in [8] above, it is characterized in that Y 3 ~Y 6 One of them is a substituted or unsubstituted cyclohexyl group, and the other three are hydrogen atoms.

[0029] Furthermore, regarding the polymer microparticles according to the present invention,

[11] in the invention described in any one of [1] to

[10] , it is characterized in that the resin has a light transmittance of 85% or more in the wavelength range of 400 nm to 800 nm and an intrinsic birefringence of -30×10 -4 Above+30×10 -4 The following resins.

[0030] Furthermore, regarding the polymer microparticles according to the present invention,

[12] in the invention described in any one of [1] to

[11] above, it is characterized in that the light-emitting material or the coloring material is an organic pigment or an organic dye.

[0031] In addition, regarding the polymer microparticles according to the present invention,

[13] in the invention described in any one of [1] to

[12] , it is characterized in that the luminescent material or the coloring material contains at least one material having a molar absorption coefficient of 10,000 M at a maximum absorption wavelength in a wavelength range of 300 nm or more. -1 cm -1 More than organic materials.

[0032] In addition, regarding the polymer microparticles according to the present invention,

[14] in the invention described in any one of [1] to

[13] above, it is characterized in that it contains at least one of the aforementioned luminescent materials, and the half-value width of the luminescence spectrum of the aforementioned luminescent material is less than 60 nm.

[0033] Furthermore, the composition according to the present invention is characterized in that

[15] it contains a binder resin and the polymer microparticles described in any one of [1] to

[14] .

[0034] Furthermore, the optical component according to the present invention is characterized in that

[16] it comprises the polymer microparticles described in any one of [1] to

[14] .

[0035] Furthermore, the light source unit according to the present invention is characterized in that

[17] it comprises a light source and the polymer microparticles described in any one of [1] to

[14] .

[0036] In addition, the display according to the present invention is characterized in that

[18] it comprises the light source unit described in

[17] .

[0037] In addition, the lighting device according to the present invention is characterized in that

[19] it includes the light source unit described in

[17] .

[0038] Furthermore, the ink according to the present invention is characterized in that

[20] it contains the polymer microparticles described in any one of [1] to

[14] .

[0039] In addition, the method for producing polymer microparticles according to the present invention is characterized in that

[21] the following steps (a) and (b) are performed in sequence.

[0040] (a) forming an emulsion comprising two phases: a polymer phase and a poor solvent phase, wherein the polymer phase comprises an organic solvent and a resin having at least one ring structure selected from the group consisting of an aliphatic hydrocarbon ring, an aliphatic heterocycle, and a ring containing an sp3 carbon, and the poor solvent phase comprises at least one of water and an alcohol and a water-soluble polymer;

[0041] Step (b): a step of at least one of heating and reducing the pressure of the emulsion while stirring to remove a portion or all of the organic solvent contained in the emulsion to precipitate polymer microparticles

[0042] In addition, with respect to the method for producing polymer microparticles according to the present invention,

[22] in the invention described in

[21] above, it is characterized in that the water-soluble polymer is at least one selected from polyvinyl alcohol, poly(vinyl alcohol-ethylene) copolymer, polyethylene glycol, cellulose derivatives and polyvinyl pyrrolidones.

[0043] In addition, regarding the method for producing polymer microparticles according to the present invention,

[23] in the invention described in

[21] or

[22] , it is characterized in that the above-mentioned step (a) and the above-mentioned step (b) do not include a polymerization step.

[0044] In addition, with respect to the method for producing polymer microparticles according to the present invention,

[24] in the invention described in any one of

[21] to

[23] above, it is characterized in that the aforementioned resin is at least one of a resin having the aforementioned ring structure in the polymer main chain and a resin in which the aforementioned ring structure is directly connected to the polymer main chain.

[0045] Furthermore, regarding the method for producing polymer microparticles according to the present invention,

[25] in the invention described in any one of

[21] to

[24] , the resin has a light transmittance of 85% or more in the wavelength range of 400 nm to 800 nm and an intrinsic birefringence of -30×10 -4 Above+30×10 -4 The following resins.

[0046] Effects of the Invention

[0047] The polymer microparticles, compositions containing the same, and optical components according to the present invention can achieve both improved durability and reduced optical loss. Therefore, by using the polymer microparticles, light source units, displays, lighting devices, and inks can be obtained that achieve both improved durability and reduced optical loss. BRIEF DESCRIPTION OF THE DRAWINGS

[0048] [ Figure 1 ] Figure 1 This is a scanning electron microscope photograph of the polymer microparticles obtained in Example 1.

[0049] [ Figure 2 ] Figure 2 This is a scanning electron microscope photograph of the polymer microparticles obtained in Comparative Example 1.

[0050] [ Figure 3 ] Figure 3 This is a scanning electron microscope photograph of the polymer microparticles obtained in Comparative Example 2.

[0051] [ Figure 4 ] Figure 4 It is a schematic cross-sectional view showing a first example of an optical component according to an embodiment of the present invention.

[0052] [ Figure 5 ] Figure 5 It is a schematic cross-sectional view showing a second example of the optical component according to the embodiment of the present invention.

[0053] [ Figure 6 ] Figure 6 It is a schematic cross-sectional view showing a third example of the optical component according to the embodiment of the present invention. DETAILED DESCRIPTION

[0054] Preferred embodiments of the polymer microparticles, their production methods, compositions, optical components, light source units, displays and lighting devices, and inks according to the present invention are described in detail below. However, the present invention is not limited to the following embodiments and can be implemented with various modifications depending on the purpose and application.

[0055] In the present invention, "above" means the same as or greater than the numerical value shown herein. In addition, "below" means the same as or less than the numerical value shown herein. In addition, "less than / lower than" means less than the numerical value shown herein.

[0056] In all groups of the compounds or partial structures described below, hydrogen may be replaced by deuterium. In the following description, for example, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms refers to an aryl group having 6 to 40 carbon atoms, including the carbon atoms contained in the substituents substituted on the aryl group. The same applies to other substituents for which the number of carbon atoms is specified.

[0057] In the case of "substituted or unsubstituted", "unsubstituted" means a case where a hydrogen atom or a deuterium atom is substituted. In the compounds or partial structures described below, the case of "substituted or unsubstituted" is the same as above.

[0058] In all the groups described below, as the substituent in the case of being substituted, 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 mercapto group, an alkoxy group, an alkylthio group, an aryl ether group, an aryl thioether group, a halogen, a cyano group, an aldehyde group, a carbonyl group, a carboxyl group, an oxycarbonyl group, an ester group, a carbamoyl group, an amide group, a sulfonyl group, a sulfonate group, a sulfonamide group, an imino group, an amino group, a nitro group, a silyl group, a siloxane group, a boron group, or a phosphine oxide group etc. can be mentioned. In addition, these substituents may be further substituted by the above-mentioned substituents.

[0059] Alkyl represents saturated aliphatic hydrocarbon groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, and they may have a substituent and may not have a substituent. There is no particular restriction on the additional substituent in the substituted situation, for example, alkyl, halogen, aryl, heteroaryl etc. can be enumerated, and this aspect is also common in the following description. In addition, the carbon number of alkyl is not particularly limited, and from the aspect of the ease of obtaining, the cost, it is preferably the scope of more than 1 and less than 20, more preferably the scope of more than 1 and less than 8.

[0060] The cycloalkyl group represents a saturated alicyclic hydrocarbon group such as cyclopropyl, cyclohexyl, norbornyl, and adamantyl, 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 or more and 20 or less.

[0061] The heterocyclic group represents an aliphatic ring having atoms other than carbon atoms in the ring, such as a pyran ring, a piperidine ring, or a cyclic amide, and may or may not have a substituent. The number of carbon atoms in the heterocyclic group is not particularly limited, but is preferably in the range of 2 or more and 20 or less.

[0062] The alkenyl group represents an unsaturated aliphatic hydrocarbon group containing a double bond, such as vinyl, allyl, butadienyl, and the like, 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 or more and 20 or less.

[0063] The cycloalkenyl group represents an unsaturated alicyclic hydrocarbon group containing a double bond, such as cyclopentenyl, cyclopentadienyl, and cyclohexenyl, 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 or more and 20 or less.

[0064] The alkynyl group represents an unsaturated aliphatic hydrocarbon group containing a triple bond, such as an ethynyl group, and may or may not have a substituent. The number of carbon atoms in the alkynyl group is not particularly limited, but is preferably within the range of 2 or more and 20 or less.

[0065] The alkoxy group represents a functional group such as a methoxy group, an ethoxy group, or a propoxy group, to which an aliphatic hydrocarbon group is bonded via an ether bond. The aliphatic hydrocarbon group may or may not have a substituent. The number of carbon atoms in the alkoxy group is not particularly limited, but is preferably within the range of 1 or more and 20 or less.

[0066] An alkylthio group is a group in which the oxygen atom in the ether bond of an alkoxy group is replaced by a sulfur atom. The hydrocarbon group of the alkylthio group may or may not have 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.

[0067] The aryl ether group represents a functional group such as a phenoxy group to which an aromatic hydrocarbon group is bonded via an ether bond. 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 within the range of 6 or more and 40 or less.

[0068] An aryl thioether group is a group in which the oxygen atom in the ether bond of an aryl ether group is substituted with a sulfur atom. The aromatic hydrocarbon group in the aryl thioether group may or may not have a substituent. The number of carbon atoms in the aryl thioether group is not particularly limited, but is preferably in the range of 6 or more and 40 or less.

[0069] Aryl represents, for example, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, triphenylenyl, benzanthryl, The aromatic hydrocarbon groups include phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, pyrenyl, fluoranthenyl, triphenylene, benzofluoranthenyl, dibenzoanthryl, perylene, and spiroenyl. Among them, preferred are phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, pyrenyl, fluoranthenyl, and triphenylene. 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, and more preferably in the range of 6 to 30.

[0070] In addition, 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, further preferably a phenyl group, a biphenyl group, or a terphenyl group, and particularly preferably a phenyl group.

[0071] When each substituent is further substituted with an aryl group, the aryl group is preferably phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthrenyl, or anthracenyl, more preferably phenyl, biphenyl, terphenyl, or naphthyl, and particularly preferably phenyl.

[0072] The heteroaryl group represents a cyclic aromatic group having atoms other than carbon in one or more rings, such as pyridyl, furyl, thienyl, quinolyl, isoquinolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, naphthyridinyl, cinnolinyl, phthalazinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothienyl, indolyl, dibenzofuranyl, dibenzothienyl, carbazolyl, benzocarbazolyl, carbolyl, indolocarbazolyl, benzofuranocarbazolyl, benzothienocarbazolyl, dihydroindenocarbazolyl, benzoquinolyl, acridinyl, dibenzoacridinyl, benzimidazolyl, imidazopyridinyl, benzoxazolyl, benzothiazolyl, and phenanthrolinyl. Here, naphthyridinyl represents any one of 1,5-naphthyridinyl, 1,6-naphthyridinyl, 1,7-naphthyridinyl, 1,8-naphthyridinyl, 2,6-naphthyridinyl, and 2,7-naphthyridinyl. The heteroaryl group may or may not have a substituent. The number of carbon atoms in the heteroaryl group is not particularly limited, but is preferably in the range of 2 to 40, and more preferably in the range of 2 to 30.

[0073] In addition, the heteroaryl group is preferably a pyridyl group, a furyl group, a thienyl group, a quinolyl group, a pyrimidinyl 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 furyl group, a thienyl group, or a quinolyl group, and particularly preferably a pyridyl group.

[0074] When each substituent is further substituted with a heteroaryl group, the heteroaryl group is preferably a pyridyl group, a furyl group, a thienyl group, a quinolyl group, a pyrimidinyl 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 furyl group, a thienyl group, or a quinolyl group, and particularly preferably a pyridyl group.

[0075] Halogen represents an atom selected from fluorine, chlorine, bromine, and iodine. Furthermore, a carbonyl group, a carboxyl group, an oxycarbonyl group, an ester group, a carbamoyl group, an amide group, and an imino group may or may not have a substituent. Examples of substituents include alkyl groups, cycloalkyl groups, aryl groups, and heteroaryl groups, and these substituents may be further substituted.

[0076] Sulfonyl, sulfonate, and sulfonamide refer to -S(=O)2R 10 、-S(=O)2OR 10 、-S(=O)2NR 10 R 11 The group represented by R 10 、R 11 A hydrogen atom or the same group as the substituents mentioned above when substituted.

[0077] The amino group is a substituted or unsubstituted amino group. Examples of substituents in the case of substitution include aryl groups, heteroaryl groups, linear alkyl groups, and branched alkyl groups. Preferred aryl and heteroaryl groups include phenyl groups, naphthyl groups, pyridyl groups, and quinolyl groups. These substituents may be further substituted. The number of carbon atoms is not particularly limited, but is preferably in the range of 2 to 50, more preferably in the range of 6 to 40, and particularly preferably in the range of 6 to 30.

[0078] Examples of silyl groups include alkylsilyl groups such as trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, propyldimethylsilyl, and vinyldimethylsilyl; and arylsilyl groups such as phenyldimethylsilyl, tert-butyldiphenylsilyl, triphenylsilyl, and trinaphthylsilyl. Substituents on silicon may be further substituted. The number of carbon atoms in a silyl group is not particularly limited, but is preferably in the range of 1 to 30.

[0079] A siloxane group represents a silicon compound group formed via an ether bond, such as a trimethylsiloxane group. The substituent on the silicon may be further substituted. In addition, a boryl group is a substituted or unsubstituted boryl group. Examples of substituents in the case of substitution include aryl groups, heteroaryl groups, straight-chain alkyl groups, branched-chain alkyl groups, aryl ether groups, alkoxy groups, and hydroxyl groups. Among them, aryl groups and aryl ether groups are preferred.

[0080] The phosphine oxide group is composed of -P(=O)R10 R 11 The group represented by R 10 and R 11 A hydrogen atom or the same group as the substituents mentioned above when substituted.

[0081] (Polymer microparticles)

[0082] The polymer particles related to the embodiments of the present invention (hereinafter sometimes referred to as polymer particles of the present invention) are polymer particles with a resin as a main component and containing a luminescent material or a coloring material. In detail, the true sphericity of the polymer particles of the present invention, which represents true sphericity, is 80 or more and 100 or less. By making the true sphericity high, the optical loss caused by undesirable light scattering at the surface of the polymer particles and multiple reflections inside the particles can be reduced. In addition, the deterioration of the luminescent material and the coloring material caused by multiple excitation can be suppressed. The true sphericity of the polymer particles of the present invention is preferably 85 or more and 100 or less, more preferably 90 or more and 100 or less, further preferably 93 or more and 100 or less, and particularly preferably 95 or more and 100 or less.

[0083] The sphericity of the polymer microparticles of the present invention is determined by randomly observing 30 particles from a scanning electron microscope photograph and determining the sphericity based on the minor axis and major axis of each of the particles using the following mathematical formula.

[0084] [Mathematical formula 1]

[0085]

[0086] In this mathematical formula, S is the sphericity, a is the major axis, b is the minor axis, and n is the number of measurements (n=30 in this embodiment).

[0087] The polymer microparticles of the present invention preferably have a D50 particle size within the range of 0.1 μm to 100 μm. If the D50 particle size exceeds 100 μm, the particle size of the polymer microparticles will exceed the thickness of the film or other layer used in the optical material, resulting in surface roughness and deterioration of the appearance. If the D50 particle size is less than 0.1 μm, the surface area of ​​the polymer microparticles becomes excessively large, which may cause thickening when used in slurries or inks, which is undesirable.

[0088] The upper limit of the D50 particle size of the polymer microparticles of the present invention is preferably 70 μm or less, more preferably 50 μm or less, even more preferably 30 μm or less, particularly preferably 20 μm or less, significantly preferably 10 μm or less, and most preferably 5.0 μm or less. The lower limit of the D50 particle size is preferably 0.2 μm or more, more preferably 0.5 μm or more, and even more preferably 1.0 μm or more.

[0089] In the present invention, the D50 particle size of the polymer microparticles is the particle size (D50 particle size) at which the cumulative number of particles from the smaller particle size side in the particle size distribution (particle size distribution) of the polymer microparticles measured by a laser diffraction particle size distribution analyzer reaches 50%.

[0090] The particle size distribution of the polymer microparticles of the present invention is represented by the ratio of the D90 particle size to the D10 particle size in the particle size distribution, i.e., D90 particle size / D10 particle size (hereinafter referred to as D90 / D10). In the polymer microparticles of the present invention, D90 / D10 is preferably 1.0 or more and 5.0 or less. When the particle size distribution of the polymer microparticles is narrow, the difference in light scattering caused by the difference in particle size disappears, and better optical uniformity is obtained, so it is preferred. Therefore, the upper limit of D90 / D10 is more preferably 4.0 or less, and more preferably 3.0 or less. In addition, from the viewpoint of excellent filling properties in a powder state, the lower limit of D90 / D10 is more preferably 1.5 or more, and more preferably 2.0 or more.

[0091] In the present invention, D90 / D10 of polymer microparticles is a value obtained by dividing the particle size distribution of polymer microparticles measured by the laser diffraction particle size distribution analyzer, which shows a cumulative number of 90% from the smaller particle size side (D90 particle size), by the particle size distribution, which shows a cumulative number of 10% from the smaller particle size side (D10 particle size).

[0092] The smoothness of the surface of the polymer microparticles of the present invention can be expressed as the amount of linseed oil absorbed by the polymer microparticles (hereinafter referred to as linseed oil absorption). Specifically, the smoother the surface of the polymer microparticles, the fewer or no pores on the surface, and the lower the linseed oil absorption.

[0093] In the polymer microparticles of the present invention, their linseed oil absorption is preferably between 1 mL / 100 g and 200 mL / 100 g. A low linseed oil absorption of the polymer microparticles results in a smoother surface and a denser interior, which is preferred because it reduces optical losses caused by unwanted light scattering at the particle surface and multiple reflections within the particle. Furthermore, the lower the linseed oil absorption of the polymer microparticles, the more effectively they can suppress the accelerated degradation of the luminescent material and coloring material caused by multiple excitations. Furthermore, when the polymer microparticles are used in slurries or inks, thickening can be reduced. Therefore, the linseed oil absorption of the polymer microparticles is more preferably between 1 mL / 100 g and 150 mL / 100 g, more preferably between 1 mL / 100 g and 120 mL / 100 g, even more preferably between 1 mL / 100 g and 100 mL / 100 g, and particularly preferably between 1 mL / 100 g and 70 mL / 100 g. The lower limit of the linseed oil absorption is preferably as low as possible.

[0094] The linseed oil absorption of the polymer microparticles was measured in accordance with Japanese Industrial Standards (JIS) JIS K 5101 (2004) "Testing methods for pigments - Purified linseed oil method".

[0095] In addition, in the polymer particles of the present invention, the smoothness of the surface and the compactness of the interior can be represented by the BET specific surface area based on gas adsorption. In detail, the smoother the surface of the polymer particles, the smaller the BET specific surface area of ​​the polymer particles becomes, and the compacter the interior of the polymer particles, the smaller the BET specific surface area of ​​the polymer particles becomes. When the surface of the polymer particles is smooth and the interior of the polymer particles is compact, the optical loss caused by the unwanted light scattering on the particle surface and the multiple reflections inside the particles can be reduced. In addition, the degradation of the luminescent material and the coloring material caused by multiple excitation can be suppressed. In addition, the surface area of ​​the polymer particles becomes smaller and the fluidity thereof is improved, so the operability of the polymer particles is excellent. Therefore, the BET specific surface area of ​​the polymer particles is preferably smaller. Specifically, the BET specific surface area of ​​the polymer particles is preferably 10m 2 / g or less, more preferably 5m 2 / g or less, more preferably 3m 2 / g or less, particularly preferably 1m 2 When the particle size of the polymer microparticles is 100 μm, the lower limit of the BET specific surface area is theoretically 0.05 m 2 / g.

[0096] The BET specific surface area of ​​the polymer microparticles is measured in accordance with Japanese Industrial Standards (JIS) JIS R1626 (1996) “Measurement method of specific surface area by gas adsorption BET method”.

[0097] The compactness of the polymer microparticles of the present invention can also be evaluated using the following formula, which represents the ratio of the theoretical surface area calculated from the BET specific surface area and the D50 particle diameter. The closer the R value in the following formula is to 1, the more gas adsorption occurs only on the outermost surface of the particle, indicating that the polymer microparticles have smooth and compact surfaces. In the polymer microparticles of the present invention, the R value in the following formula is preferably 5 or less, more preferably 4 or less, even more preferably 3 or less, and most preferably 2 or less. The theoretical lower limit of the R value is 1.

[0098] [Mathematical formula 2]

[0099] R=ADα / 6

[0100] In this formula, R is the surface area ratio, D is the D50 particle size, α is the density of the polymer microparticles, and A is the BET specific surface area.

[0101] (resin in polymer particles)

[0102] As mentioned above, the polymer particles of the present invention are based on resin and include polymer particles of luminescent material or coloring material. In such polymer particles, as the resin constituting the particles, it is preferred to use excellent materials such as transparency and heat resistance. As the example of the kind of the resin, for example, acrylic acid, methacrylic acid, polyvinyl cinnamate, cyclic rubber, etc. can be enumerated. There are photocurable resist materials with reactive vinyl groups, 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, aromatic polyolefin resins, known resins. In addition, about the resin included as the main component in the polymer particles of the present invention, a mixture or copolymer of these resins can be used. By appropriately designing these resins, it is possible to obtain the resin useful to the polymer particles of the present invention.

[0103] Among these resins, from the perspectives of transparency and dispersibility of the luminescent material or coloring material, acrylic resins, copolymer resins containing acrylate or methacrylate moieties, polyester resins, cycloolefin resins, epoxy resins, and silicone resins are preferred. More preferred are acrylic resins, copolymer resins containing acrylate or methacrylate moieties, and polyester resins, with acrylic resins and copolymer resins containing acrylate or methacrylate moieties being particularly preferred. Furthermore, from the perspective of heat resistance, thermosetting resins and photocurable resins are preferably used.

[0104] In addition, the polymer microparticles of the present invention contain as their main component a resin having at least one ring structure selected from the group consisting of an aliphatic hydrocarbon ring, an aliphatic heterocycle, and a ring containing sp3 carbon in its molecular structure. When the resin serving as the main component contains at least one of these ring structures in its molecular structure, the molecular motion of the resin is suppressed, thereby suppressing changes in the dispersion state of the luminescent material or coloring material in the polymer microparticles and, therefore, preventing these materials from coming into proximity with each other. Furthermore, by making the ring structure in the molecular structure of the resin at least one ring structure selected from the group consisting of an aliphatic hydrocarbon ring, an aliphatic heterocycle, and a ring containing sp3 carbon, the number of π-conjugated structures in the resin is reduced, thereby reducing the generation of active species due to light absorption. This suppresses the degradation of the luminescent material or coloring material in the polymer microparticles, thereby preventing a decrease in the durability of the polymer microparticles. Here, sp3 carbon refers to a carbon atom bonded to four atoms via sp3 hybrid orbitals.

[0105] The number of atoms constituting the above-mentioned aliphatic hydrocarbon ring, aliphatic heterocycle and ring containing sp3 carbon is not particularly limited, and is usually in the range of 3 to 30, preferably in the range of 4 to 20, and more preferably in the range of 5 to 15.

[0106] Specific examples of aliphatic hydrocarbon rings, aliphatic heterocycles, and ring structures containing sp3 carbons include, for example, cyclobutane, cyclopentane, cyclohexane, norbornene, adamantane, pyrrolidine, piperidine, oxirane, oxetane, furan, tetrahydropyran, morpholine, dioxane, indane, fluorene, cyclic esters, cyclic amides, and derivatives thereof. Among these, cyclohexane, norbornene, adamantane, oxirane, fluorene, cyclic esters, cyclic amides, and derivatives thereof are preferred, cyclohexane, norbornene, adamantane, fluorene, cyclic esters, and derivatives thereof are more preferred, cyclohexane, norbornene, fluorene, cyclic esters, and derivatives thereof are further preferred, and cyclohexane, norbornene, fluorene, cyclic esters, and derivatives thereof are particularly preferred, and cyclohexane, norbornene, and derivatives thereof are particularly preferred.

[0107] In the polymer microparticles of the present invention, the resin as the main component is preferably at least one of the first resin and the second resin shown below. The first resin is a resin having at least one ring structure selected from the group consisting of aliphatic hydrocarbon rings, aliphatic heterocycles, and rings containing sp3 carbons in the polymer main chain. The second resin is a resin having at least one ring structure selected from the group consisting of aliphatic hydrocarbon rings, aliphatic heterocycles, and rings containing sp3 carbons directly connected to the polymer main chain. When the at least one ring structure is contained in the polymer main chain or is directly connected to the polymer main chain, the molecular motion of the resin can be more effectively suppressed compared to when the ring structure is introduced into the polymer side chain. As a result, changes in the dispersion state of the luminescent material or coloring material in the polymer microparticles can be suppressed.

[0108] In addition, in the polymer particles of the present invention, in order to disperse the luminescent material or coloring material well in the resin, the resin (the resin as the main component) preferably has both a partial structure with high compatibility with the luminescent material or coloring material and a partial structure with low compatibility. As a further preferred embodiment of the resin, for example, a copolymer randomly containing a partial structure with high compatibility with the luminescent material or coloring material and a partial structure with low compatibility can be mentioned.

[0109] The partial structure with high compatibility with the luminescent material or coloring material is not particularly limited, but includes moieties derived from acrylic acid, methacrylic acid, acrylates, or methacrylates, and moieties linked via ester or amide bonds. On the other hand, the partial structure with low compatibility with the luminescent material or coloring material is not particularly limited, but includes moieties derived from vinyl compounds containing only carbon atoms and vinyl compounds having aliphatic hydrocarbon rings. Therefore, the resin as the main component preferably has at least one of a moiety derived from acrylic acid, methacrylic acid, acrylates, or methacrylates, and a moiety linked via an ester or amide bond; and at least one of a moiety derived from a vinyl compound containing only carbon atoms and a moiety derived from a vinyl compound having aliphatic hydrocarbon rings.

[0110] From the perspective of ensuring compatibility between the resin as the main component and the luminescent material or coloring material and ensuring good dispersion of these materials in the resin, the content of the partial structure with high compatibility with the luminescent material or coloring material in the copolymer as the resin is preferably 30 wt% or more, more preferably 50 wt% or more, and even more preferably 70 wt% or more of the total amount of the resin. On the other hand, the content of the partial structure with low compatibility with the luminescent material or coloring material in the copolymer as the resin is preferably 70 wt% or less, more preferably 50 wt% or less, and even more preferably 30 wt% or less of the total amount of the resin.

[0111] Preferred examples of the resin as the main component are not particularly limited, but include resins having a partial structure represented by the general formula (1) and a partial structure represented by the general formula (2) in their molecular structures.

[0112] [Chemical Formula 2]

[0113]

[0114] In the general formula (1), Y 1 and Y 2 They may be the same or different and are hydrogen atoms or organic groups having 1 to 20 carbon atoms. 3 ~Y 6 They may be the same or different and are hydrogen atoms or organic groups having 1 to 20 carbon atoms, and Y 3 ~Y 6 At least one of them is a group containing an aliphatic cyclic hydrocarbon structure.

[0115] From the viewpoint of good copolymerization reactivity, Y in the general formula (1) 1 A hydrogen atom or a methyl group is preferred, and a methyl group is more preferred from the viewpoint of reducing the generation of free radicals.

[0116] From the viewpoint of improving the heat resistance of the resin, Y in the general formula (1) 2 Preferably, it is a hydrogen atom, an alkyl group, a cycloalkyl group, a heterocyclic group, an alkenyl group, a cycloalkenyl group, an alkynyl group, a hydroxyl group, a mercapto group, an alkoxy group, an alkylthio group, an aryl ether group, an aryl thioether group, an aryl group or a heteroaryl group. In addition, these groups may be further substituted with the above-mentioned substituents. Among these, Y 2 More preferably, it is a methyl group or a cycloalkyl group. 2 A methyl group is more preferred.

[0117] From the viewpoint of improving the heat resistance of the resin, Y in the general formula (2) 3 ~Y 6 Preferably, it is a hydrogen atom, an alkyl group, a cycloalkyl group, a heterocyclic group, an alkenyl group, a cycloalkenyl group, an alkynyl group, a hydroxyl group, a mercapto group, an alkoxy group, an alkylthio group, an aryl ether group, an aryl thioether group, an aryl group or a heteroaryl group. In addition, these groups may be further substituted by the above-mentioned substituents.

[0118] As mentioned above, Y in the general formula (2) 3 ~Y 6 At least one of them is a group containing an aliphatic cyclic hydrocarbon structure. From the perspective of ease of acquisition and cost, it is preferred that these Y 3 ~Y 6 At least one of Y is a substituted or unsubstituted cyclohexyl group, but there is no particular limitation. 3 ~Y 6 One of them is a substituted or unsubstituted cyclohexyl group, and the other three are hydrogen atoms.

[0119] The content of the repeating unit of the partial structure represented by general formula (1) is not particularly limited, but is preferably 30 wt% or more of the total amount of the resin as the main component, more preferably 50 wt% or more, further preferably 60 wt% or more, and particularly preferably 70 wt% or more. By ensuring that the proportion of the repeating unit of the partial structure represented by general formula (1) is within the above range, the compatibility of the resin with the luminescent material or the coloring material can be ensured, and these materials can be well dispersed in the resin.

[0120] The content of the repeating unit of the partial structure represented by general formula (1) is preferably 95 wt% or less, more preferably 90 wt% or less, and even more preferably 85 wt% or less of the total amount of the resin as the main component. By setting the ratio of the repeating unit of the partial structure represented by general formula (1) within the above range, the compatibility of the resin with the luminescent material or the coloring material can be ensured, and these materials can be well dispersed in the resin.

[0121] The content of the repeating unit of the partial structure represented by general formula (2) is preferably 5 wt% or more, more preferably 10 wt% or more, and particularly preferably 15 wt% or more of the total amount of the resin as the main component. By setting the content of the repeating unit of the partial structure represented by general formula (2) within the above range, the compatibility of the resin with the luminescent material or the coloring material can be ensured, and these materials can be well dispersed in the resin.

[0122] The content of the repeating unit of the partial structure represented by general formula (2) is preferably 70 wt% or less, more preferably 50 wt% or less, and even more preferably 30 wt% or less of the total amount of the resin as the main component. By setting the ratio of the repeating unit of the partial structure represented by general formula (2) within the above range, the compatibility of the resin with the luminescent material or the coloring material can be ensured, and these materials can be well dispersed in the resin.

[0123] In addition, in the polymer microparticles of the present invention, the lower limit of the glass transition temperature (Tg) of the resin as its main component is not particularly limited, but is preferably 80°C or above, and more preferably 100°C or above. When the Tg of the resin is 100°C or above, the molecular motion of the resin caused by the heat brought by the incident light from the light source and the driving heat of the equipment is further suppressed, and even under high temperature conditions, changes in the dispersion state of the luminescent material or coloring material in the resin can be suppressed. As the lower limit of the Tg of the resin, it is more preferably 110°C or above, and even more preferably 120°C or above. The upper limit of the Tg of the resin is not particularly limited. However, if the crystallinity of the resin is excessively high, the dispersibility of the luminescent material or coloring material in the resin deteriorates, so the upper limit of the Tg of the resin is preferably 180°C or below.

[0124] The glass transition temperature of a thermoplastic resin can be measured using a commercially available measuring instrument (e.g., a differential scanning calorimeter (trade name: DSCQ20) manufactured by TA Instruments) at a heating rate of 20°C / minute. The sample for measurement is not particularly limited as long as it can be placed in the measurement container. However, the measurement is preferably performed in a powder or fine particle form, or in a state where the resin solution has been cast and thoroughly dried to remove the solvent.

[0125] In the polymer microparticles of the present invention, the lower limit of the weight average molecular weight (Mw) of the resin serving as the main component is preferably 5,000 or more, more preferably 15,000 or more, and even more preferably 20,000 or more. Furthermore, the upper limit of the weight average molecular weight is preferably 500,000 or less, more preferably 100,000 or less, and even more preferably 50,000 or less. When the weight average molecular weight is within the above range, the uniformity of shape and particle size is improved when the particles are formed into particles.

[0126] Here, the weight average molecular weight can be measured as a weight average molecular weight in terms of polystyrene by performing GPC analysis using a commercially available measuring instrument (for example, a GPC analyzer manufactured by Tosoh Corporation (trade name HLC-8220)) in accordance with Japanese Industrial Standards (JIS standards) JIS K7252-3 (2008).

[0127] Furthermore, in the polymer microparticles of the present invention, the resin as the main component preferably has a light transmittance of 85% or higher within a wavelength range of 400 nm to 800 nm. The higher this light transmittance, the higher the transparency of the resin. When polymer microparticles containing this resin are used as a component material for light source units, etc., optical loss can be reduced. This light transmittance is preferably 87% or higher, more preferably 90% or higher, even more preferably 91% or higher, and particularly preferably 92% or higher.

[0128] The light transmittance of the resin in the wavelength range of 400 nm to 800 nm can be measured using a resin sample sheet having a film thickness of 1 μm to 100 μm using a commercially available measuring instrument (e.g., a UV-visible spectrophotometer (trade name U-3010) manufactured by Hitachi, Ltd.).

[0129] In addition, the intrinsic birefringence of the resin as the main component is preferably -30×10 -4 Above+30×10 -4 The smaller the absolute value of the intrinsic birefringence of the resin, the more light diffusion in the resin can be prevented. The intrinsic birefringence of the resin is preferably -25×10 -4 Above+25×10 -4 Below, more preferably -20×10 -4 Above+20×10 -4 Below, more preferably -15×10 -4 Above+15×10 -4 Below, more preferably -10×10 -4 Above+10×10 -4 the following.

[0130] The intrinsic birefringence of the resin can be determined by calculating the dielectric polarization difference of each bonding unit of the structural unit using a molecular orbital method such as the AM1 method or the PM3 method, and calculating the value (intrinsic birefringence value) as the volume average using the following Lorentz-Lorenz equation.

[0131] [Mathematical formula 3]

[0132] Δn0=2 / 9π×(n 2 +2) 2 / n×ΔP·d·N / M

[0133] In this formula, Δn0 is the intrinsic birefringence value, ΔP is the difference between the dielectric polarizability in the axial direction of the molecular chain and the dielectric polarizability in the direction perpendicular to the molecular chain axis, n is the refractive index, d is the density, N is the Avogadro constant, and M is the molecular weight.

[0134] Resins useful for the polymer microparticles of the present invention can be obtained, for example, by copolymerizing the raw material monomers in the presence of a polymerization initiator and a catalyst. Commercially available resins may also be used. Examples of commercially available resins include, but are not limited to, Optimas (registered trademark) 6500, Optimas (registered trademark) 7500, and Iupizeta (registered trademark) EP-5000 manufactured by Mitsubishi Gas Chemical Co., Ltd., and OKP (registered trademark) 4 and OKP (registered trademark)-A1 manufactured by Osaka Gas Chemicals Co., Ltd. Furthermore, resins disclosed in Japanese Patent Application Laid-Open Nos. 2021-162621, 2022-116643, 2022-179996, 2022-72382, 2020-180184, and 2018-53044 can also be preferably used.

[0135] (Luminescent material or coloring material)

[0136] As described above, the polymer particles of the present invention are particles having a resin as a main component and containing a luminescent material or a coloring material. Specific examples of luminescent materials or coloring materials that can be preferably used in the polymer particles of the present invention include, for example, inorganic phosphors, organic pigments, organic dyes, quantum dots, etc. The polymer particles of the present invention may contain two or more of these as the above-mentioned luminescent materials or coloring materials. Among these, organic pigments or organic dyes are more preferably used from the viewpoint of high dispersibility in the resin, reduction in usage, and reduction in environmental load. Organic dyes are further preferably used.

[0137] Suitable examples of organic pigments or organic dyes include compounds having a condensed aromatic ring or derivatives thereof, compounds having a heteroaryl ring or derivatives thereof, borane derivatives, stilbene derivatives, aromatic acetylene derivatives, tetraphenylbutadiene derivatives, aldazine derivatives, pyrromethene derivatives, diketopyrrolo[3,4-c]pyrrole derivatives, coumarin derivatives, azole derivatives and metal complexes thereof, cyanine compounds, xanthene compounds, thioxanthene compounds, polyphenylene compounds, naphthalimide derivatives, phthalocyanine derivatives and metal complexes thereof, porphyrin derivatives and metal complexes thereof, oxazine compounds, helicene compounds, aromatic amine derivatives, and organometallic complex compounds.

[0138] Examples of compounds having a condensed aromatic ring and derivatives thereof include naphthalene, anthracene, phenanthrene, pyrene, Tetracene, triphenylene, perylene, fluoranthene, fluorene, indene, etc. Examples of compounds having a heteroaryl ring and derivatives thereof include furan, pyrrole, thiophene, silole, 9-silafluorene, 9,9'-spirodisilafluorene, benzothiophene, benzofuran, indole, dibenzothiophene, dibenzofuran, imidazopyridine, phenanthroline, pyridine, pyrazine, naphthyridine, quinoxaline, and pyrrolopyridine.

[0139] Examples of stilbene derivatives include 1,4-distyrylbenzene, 4,4'-bis(2-(4-diphenylaminophenyl)vinyl)biphenyl, and 4,4'-bis(N-(stilbene-4-yl)-N-phenylamino)stilbene. Examples of coumarin derivatives include coumarin 6, coumarin 7, and coumarin 153. Examples of azole derivatives and their metal complexes include imidazole, thiazole, thiadiazole, carbazole, oxazole, oxadiazole, and triazole.

[0140] Examples of cyanine compounds include indocyanine green. Examples of xanthene compounds and thioxanthene compounds include fluorescein, eosin, and rhodamine. Examples of oxazine compounds include Nile red and Nile blue. Examples of aromatic amine derivatives include N,N'-diphenyl-N,N'-di(3-methylphenyl)-4,4'-diphenyl-1,1'-diamine. Examples of organometallic complex compounds include iridium (Ir), ruthenium (Ru), rhodium (Rh), palladium (Pd), platinum (Pt), osmium (Os), and rhenium (Re).

[0141] Among the above-mentioned organic pigments or organic dyes, more suitable examples include perylene derivatives, xanthene compounds, pyrromethene derivatives, diketopyrrolo[3,4-c]pyrrole derivatives, coumarin derivatives, phthalocyanine derivatives and metal complexes thereof, and porphyrin derivatives and metal complexes thereof, in view of their large absorption coefficient and high heat resistance.

[0142] In the polymer microparticles of the present invention, the luminescent material or the coloring material preferably contains at least one material having a molar absorption coefficient of 10,000 nm at a maximum absorption wavelength in a range of 300 nm or longer. -1 cm -1 By making the molar absorption coefficient of these materials large, they can absorb light efficiently. As the above molar absorption coefficient, it is more preferably 20,000M -1 cm -1 More than 30,000M -1 cm -1Above, particularly preferably 50,000M -1 cm -1 Examples of suitable organic materials with large molar absorption coefficients include perylene derivatives, xanthene compounds, pyrromethene derivatives, diketopyrrolo[3,4-c]pyrrole derivatives, coumarin derivatives, phthalocyanine derivatives and metal complexes thereof, and porphyrin derivatives and metal complexes thereof. However, the organic materials are not particularly limited to these.

[0143] In one embodiment of the polymer microparticles of the present invention, the polymer microparticles preferably contain at least one luminescent material, and the half-value width of the luminescence spectrum of the luminescent material is 60 nm or less. In this case, the polymer microparticles of the present invention can absorb incident light and convert the absorbed incident light into light of high color purity at a wavelength different from that of the incident light. The luminescent material is more preferably one having a half-value width of the luminescence spectrum of 50 nm or less, more preferably one having a half-value width of 40 nm or less, and particularly preferably one having a half-value width of 30 nm or less.

[0144] The light-emitting material contained in the polymer microparticles of the present invention is preferably at least one of the compound represented by general formula (3), the compound represented by general formula (4), and the compound represented by general formula (5) from the viewpoint of exhibiting light emission with high color purity.

[0145] [Chemical Formula 3]

[0146]

[0147] In the general formula (3), X is CR 7 or N. R 1 ~R 9 The substituents may be the same or different and may be selected from a hydrogen atom, 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 mercapto group, an alkoxy group, an alkylthio group, an aryl ether group, an aryl thioether group, a halogen, a cyano group, an aldehyde group, a carbonyl group, a carboxyl group, an oxycarbonyl group, an ester group, a carbamoyl group, an amide group, a sulfonyl group, a sulfonate group, a sulfonamide group, an amino group, an imino group, a nitro group, a silyl group, a siloxane group, a boron group, a phosphine oxide group, and a condensed ring and an aliphatic ring formed with an adjacent substituent.

[0148] [Chemical Formula 4]

[0149]

[0150] In general formulae (4) and (5), ring Za, ring Zb, and ring Zc are each independently a substituted or unsubstituted aryl ring having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl ring having 5 to 30 ring carbon atoms.

[0151] In general formula (4), Z 1 and Z 2 Each is independently an oxygen atom, NRa (a nitrogen atom having a substituent Ra) or a sulfur atom. 1 In the case of NRa, the substituent Ra may be bonded to the ring Za or the ring Zb to form a ring. 2 In the case of NRa, the substituent Ra may be bonded to the ring Za or the ring Zc to form a ring. E is a boron atom, a phosphorus atom, SiRa (a silicon atom having a substituent Ra), or P=O.

[0152] In general formula (5), E 1 and E 2 Each is independently BRa (boron atom having a substituent Ra), PRa (phosphorus atom having a substituent Ra), SiRa2 (silicon atom having two substituents Ra), P(=O)Ra2 (phosphine oxide having two substituents Ra) or P(=S)Ra2 (phosphine sulfide having two substituents Ra), C=O (carbonyl group), S(=O) or S(=O)2. 1 When it is BRa, PRa, SiRa2, P(=O)Ra2 or P(=S)Ra2, the substituent Ra may be bonded to the ring Za or the ring Zb to form a ring. 2 In the case of BRa, PRa, SiRa2, P(=O)Ra2 or P(=S)Ra2, the substituent Ra may be bonded to the ring Za or the ring Zc to form a ring.

[0153] The above-mentioned substituents R are each independently a substituent selected from a hydrogen atom, 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 sulfhydryl group, an alkoxy group, an alkylthio group, an aryl ether group, an aryl thioether group, a halogen, a cyano group, an aldehyde group, a carbonyl group, a carboxyl group, an oxycarbonyl group, an ester group, a carbamoyl group, an amide group, a sulfonyl group, a sulfonate group, a sulfonamide group, an amino group, an imino group, a nitro group, a silyl group, a siloxane group, a boron group, a phosphine oxide group, and a condensed ring and an aliphatic ring formed with an adjacent substituent. In addition, the substituent R may be further substituted by a substituent selected from these substituents. The substituent that replaces the substituent R may be further substituted by a substituent selected from these substituents.

[0154] In the general formula (3), the fused ring and aliphatic ring formed with adjacent substituents refer to any two adjacent substituents (for example, R 2 With R 3) are bonded to each other to form a conjugated or non-conjugated cyclic skeleton. In the compound represented by general formula (3), such a condensed ring or aliphatic ring may also be formed. As a constituent element of such a condensed ring or aliphatic ring, in addition to carbon, an element selected from nitrogen, oxygen, sulfur, phosphorus and silicon may also be contained. In addition, the above-mentioned condensed ring or aliphatic ring may be further condensed with other rings.

[0155] In the general formula (3), R 8 and R 9 Preferably, R is fluorine, a fluorine-containing alkyl group, a fluorine-containing heteroaryl group or a fluorine-containing aryl group, a fluorine-containing alkoxy group, a fluorine-containing aryloxy group, a fluorine-containing heteroaryloxy group, or a cyano group. In particular, from the perspective of being stable to the excitation light and being able to obtain a higher fluorescence quantum yield, R is preferably 8 and R 9 More preferred is fluorine or cyano.

[0156] In general formula (3), from the viewpoint of light stability, X is preferably CR 7 In addition, from the perspective of providing a higher fluorescence quantum yield and being less susceptible to thermal decomposition and from the perspective of photostability, it is preferred that X is CR 7 , and R 7 is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. Among them, since it can suppress the reduction of photostability caused by excessive increase in the torsion of the carbon-carbon bond, R is preferably 7 is a substituted or unsubstituted phenyl group.

[0157] In another embodiment of the compound represented by the general formula (3), R 1 With R 2 、R 2 With R 3 、R 4 With R 5 , and R 5 With R 6 At least one of these four groups is a ring structure represented by any one of the following general formulae (6A) to (6D). Each ring structure represented by each of the general formulae (6A) to (6D) has a double bond. Therefore, by introducing any one of the ring structures into the above-mentioned compound, conjugation can be expanded to lengthen the wavelength of luminescence. Furthermore, by utilizing the ring structure introduced into the above-mentioned compound, the double bond site can be fixed to the central skeleton with a chemical bond, thereby suppressing excessive structural relaxation in the excited state and obtaining luminescence with good color purity.

[0158] [Chemical Formula 5]

[0159]

[0160] In the general formulas (6A) to (6D), R 101 、R102 and R 201 ~R 204 and R in general formula (3) 1 ~R 7 Ar in the general formula (6D) is a substituted or unsubstituted aromatic hydrocarbon ring, or a substituted or unsubstituted aromatic heterocyclic ring. In addition, in each ring structure represented by the general formulas (6A) to (6D), R 101 With R 102 A ring may be formed. * in the general formulae (6A) to (6D) represents a linking portion to the pyrromethene skeleton.

[0161] In the ring structure represented by general formula (6D), Ar is preferably a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted phenanthrene ring, a substituted or unsubstituted pyridine ring, a substituted or unsubstituted pyrimidine ring, or a substituted or unsubstituted pyrazine ring. Furthermore, when Ar is a substituted or unsubstituted benzene ring, thermal stability and photochemical stability are improved, which is preferred.

[0162] In each ring structure represented by general formulae (6A) to (6D), R 101 With R 102 A ring can be formed. 101 With R 102 The formation of a ring suppresses structural relaxation and enables sharp luminescence. In addition, the thermal vibration of the entire molecule is suppressed, thereby improving thermal stability. 101 With R 102 A preferred example of forming a ring is when they form a spirofluorene ring. Specifically, R 101 and R 102 Both are benzene rings and they form a ring structure.

[0163] As a first preferred example of the compound represented by the general formula (3), the following can be mentioned: 1 、R 3 、R 4 and R 6 All of them may be the same or different, and are substituted or unsubstituted phenyl groups. In addition, X is CR 7 , R 7 is a substituted or unsubstituted phenyl group. In this case, R 1 、R 3 、R 4 、R 6 and R 7 At least one of them is a phenyl group substituted by a methoxy group.

[0164] As a second preferred example of the compound represented by the general formula (3), the following can be mentioned: 1 、R 3、R 4 and R 6 All of them may be the same or different and are substituted or unsubstituted alkyl groups. In addition, X is CR 7 , R 7 is a substituted or unsubstituted phenyl group. In this case, R 2 and R 5 Each group may be the same as or different, and is more preferably a substituted or unsubstituted ester group, and even more preferably a substituted or unsubstituted aryl ester group.

[0165] As a third preferred example of the compound represented by the general formula (3), the following can be mentioned: 2 and R 3 is a ring structure represented by the general formula (6D), wherein Ar in the general formula (6D) is a substituted or unsubstituted benzene ring, and R in the general formula (6D) is 101 and R 102 Each of them may be the same or different, and is a substituted or unsubstituted alkyl group, or a substituted or unsubstituted phenyl group, and X is CR 7 , R 7 is a substituted or unsubstituted phenyl group. In this case, R 4 and R 6 They may be the same or different, and are more preferably substituted or unsubstituted phenyl. 101 With R 102 Ring formation is also preferred.

[0166] In the general formula (4) and the general formula (5), examples of the substituted or unsubstituted aryl ring having 6 to 30 ring carbon atoms in ring Za, ring Zb and ring Zc include benzene ring, naphthalene ring, phenanthrene ring, Aromatic hydrocarbon rings such as anthracene rings, pyrene rings, and pyrene rings are preferred. Among these, a benzene ring is preferred from the perspective of ensuring solubility. Examples of heteroaryl rings having 5 to 30 ring carbon atoms include aromatic heteroaryl ring structures such as pyridine rings, quinoline rings, and phenanthroline rings. Among these, a pyridine ring is preferred from the perspective of ease of raw material availability and ease of synthesis.

[0167] In general formula (4) and general formula (5), the substituent Ra is preferably a group having 6 to 40 carbon atoms including the substituent. The substituent Ra is preferably a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group, and more preferably a substituted or unsubstituted aryl group. Examples of the substituted or unsubstituted aryl group include substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted naphthyl, and substituted or unsubstituted phenanthrenyl. Among these, substituted or unsubstituted phenyl is more preferred.

[0168] In the general formula (4), Z 1and Z 2 Preferably, it is an oxygen atom or NRa. The reason is that the π conjugated system of the compound represented by general formula (4) is efficiently expanded, and the light excitation efficiency is improved. Similarly, E in general formula (4) is preferably a boron atom, and E in general formula (5) is preferably a boron atom. 1 and E 2 BRa is preferred because the π-conjugated system is efficiently expanded.

[0169] In general formula (4) and general formula (5), ring Za, ring Zb, and ring Zc are preferably benzene rings because the π-conjugated system of the compound represented by general formula (4) or general formula (5) is efficiently expanded.

[0170] Regarding the compounds represented by the general formula (4) or the general formula (5), as described in the literature Adv. Mater., 2016, 28, 2777-2781, the HOMO orbital and the LUMO orbital can be separated by the multiple resonance effect by optimally arranging the electron-donating amine nitrogen atom and the electron-accepting boron atom. From the viewpoint of facilitating delayed fluorescence by clearly separating the HOMO orbital and the LUMO orbital and bringing the energy level of the excited singlet state and the energy level of the excited triplet state closer, in the general formula (4), it is preferred that E is a boron atom with strong electron-accepting property, and Z is 1 and Z 2 They are all groups with strong electron donating properties, namely NRa.

[0171] Furthermore, it is more preferable that the substituent Ra of the general formula (4) and the general formula (5) forms a structure bonded to at least one ring among ring Za, ring Zb, and ring Zc. This is because by bonding the substituent Ra to at least one ring among ring Za, ring Zb, and ring Zc, it is expected that E in the general formula (4) and E in the general formula (5) can be bonded to 1 and E 2 The steric protection effect is further improved, and the effect of inhibiting the decrease in fluorescence quantum yield is further improved.

[0172] Examples of the compound represented by general formula (3), the compound represented by general formula (4), and the compound represented by general formula (5) are shown below, but the compound is not limited to these.

[0173] [Chemical Formula 6]

[0174]

[0175] [Chemical Formula 7]

[0176]

[0177] [Chemical Formula 8]

[0178]

[0179] [Chemical Formula 9]

[0180]

[0181] [Chemical Formula 10]

[0182]

[0183] In addition, an example of organic pigment or organic dye except the compound represented by general formula (3), the compound represented by general formula (4) and the compound represented by general formula (5) is shown below.But, organic pigment or organic dye are not particularly limited to these.For example, the commercially available materials such as disclosed compound, Alexa Fluor (registered trademark) series, ATTO series in Japanese Patent Publication No. 2014-519191, Japanese Patent Publication No. 2016-534100, Japanese Patent Publication No. 2017-523124, Japanese Patent Publication No. 2019-533737, Japanese Patent Publication No. 2020-507620, Japanese Patent Publication No. 2022-540302 etc. also can preferably be used.

[0184] [Chemical Formula 11]

[0185]

[0186] In the polymer particles of the present invention, the luminescent material or coloring material may contain other compounds as needed, in addition to the compounds exemplified above. For example, an auxiliary dopant may be included to improve the efficiency of energy transfer from the excitation light to the luminescent material. Furthermore, if it is desired to add color to the luminescent material, known luminescent materials such as the aforementioned organic luminescent materials, inorganic phosphors, fluorescent pigments, fluorescent dyes, and quantum dots may be included.

[0187] (Method for producing polymer microparticles)

[0188] The method for producing polymer microparticles according to an embodiment of the present invention (hereinafter sometimes referred to as the method for producing polymer microparticles of the present invention) is not particularly limited as long as it can produce the polymer microparticles of the present invention described above. For example, the polymer microparticles of the present invention can be produced by known methods such as interfacial polymerization, W / O liquid drying, Stober method, spray drying, in situ polymerization, phase separation from aqueous solution, phase separation from organic solvent, melt dispersion cooling, and gas suspension coating.

[0189] Among the above methods, a method of producing fine particles from a resin produced by polymerization or a composition containing the resin is preferred from the viewpoint of being able to suppress the residue of emulsifiers, polymerization initiators, modified products thereof, and the like in polymer fine particles.

[0190] In particular, the method for producing polymer microparticles of the present invention is preferably a method comprising the following steps (a) and (b), and performing these steps (a) and (b) in sequence. Specifically, step (a) is a step of forming an emulsion containing two phases, the first phase and the second phase, in its molecular structure. The first phase is a polymer phase containing an organic solvent and a resin having at least one ring structure selected from the group consisting of an aliphatic hydrocarbon ring, an aliphatic heterocycle, and a ring containing sp3 carbon. The second phase is a poor solvent phase containing at least one of water and an alcohol and a water-soluble polymer. Step (b) is a step of removing a portion or all of the organic solvent contained in the emulsion by heating and reducing the pressure while stirring the emulsion obtained in the above step (a), thereby precipitating polymer microparticles.

[0191] This method involves removing the organic solvent from a homogeneous emulsion containing the first and second phases to obtain polymer microparticles. Therefore, this method can produce polymer microparticles with desired true sphericity and linseed oil absorption. Furthermore, by adjusting the viscosity ratio between the dispersed phase and the continuous phase, the interfacial tension, and the applied stirring power, polymer microparticles with a desired particle size and size distribution can be produced.

[0192] One embodiment of this method is to crosslink and cure the resin in any of the stages (a) and (b) above, either in the emulsified state, during the removal of the organic solvent, or in the fine particle state after removal. This is preferred because the heat resistance of the resulting polymer fine particles is improved.

[0193] As another embodiment of the present method, the aforementioned polymerization step is preferably not included in steps (a) and (b). In this case, impurities such as polymerization initiators, catalysts, and unreacted monomers can be prevented from remaining in the resulting polymer microparticles, thereby suppressing changes in optical properties such as coloration caused by trace amounts of impurities.

[0194] From the perspective of suppressing changes in optical properties such as coloration caused by the aforementioned trace impurities, the content of the polymerization initiator and its decomposition products in the polymer microparticles of the present invention is preferably less than 0.1 wt %, more preferably less than 0.05 wt %, even more preferably less than 0.01 wt %, and particularly preferably less than 0.001 wt %. The lower the content of the polymerization initiator and its decomposition products in the polymer microparticles, the better.

[0195] The organic solvent contained in the above-mentioned polymer phase is not particularly limited as long as it can dissolve the resin as the main component of the polymer particles and form an organic phase and separate from the aqueous phase (poor solvent phase in the above-mentioned emulsion) comprising at least one of water and alcohol and a water-soluble polymer. As such an organic solvent, it can be appropriately selected, but it is preferred to use an aprotic solvent. Specifically, as the organic solvent, hexane, cyclohexane, dioxane, toluene, ether, ethyl acetate, tetrahydrofuran, pyridine, ethylene glycol, acetonitrile, chloroform, dichloromethane, etc. can be enumerated. Among these, from the perspective of having a low boiling point and being able to selectively only remove the organic solvent in the above-mentioned (b) process, hexane, cyclohexane, ether, ethyl acetate, tetrahydrofuran, acetonitrile, chloroform, dichloromethane are more preferred. In addition, from the perspective of being less miscible with the poor solvent in the above-mentioned step (a) and being able to form a stable emulsion, hexane, cyclohexane, diethyl ether, ethyl acetate, chloroform, and dichloromethane are further preferred. From the perspective of excellent resin solubility, cyclohexane, ethyl acetate, chloroform, and dichloromethane are particularly preferred.

[0196] Furthermore, if the polymer microparticles of the present invention contain an excessive amount of solvent, the molecular motion of the resin in the polymer microparticles may be promoted, potentially accelerating changes in the dispersion state of the luminescent material or coloring material. Consequently, the durability of the polymer microparticles may deteriorate. Specifically, to suppress degradation of the durability of the polymer microparticles, it is preferable to suppress residual solvent in the polymer microparticles. The boiling point of the organic solvent is preferably 130°C or lower. This boiling point is more preferably 120°C or lower, further preferably 100°C or lower, and particularly preferably 80°C or lower. Furthermore, the solvent content in the polymer microparticles is preferably less than 1 wt%, more preferably less than 0.5 wt%, and further preferably less than 0.1 wt%.

[0197] In the method for producing polymer microparticles of the present invention, the water-soluble polymer that can be preferably used is at least one selected from the group consisting of polyvinyl alcohol, poly(vinyl alcohol-ethylene) copolymers, polyethylene glycol, cellulose derivatives, and polyvinyl pyrrolidones. Among these, polyvinyl alcohol, poly(vinyl alcohol-ethylene) copolymers, and polyethylene glycol are more preferred from the viewpoint of excellent interfacial stabilization between the dispersed phase and the continuous phase and the ability to form a homogeneous emulsion. Polyvinyl alcohol and polyethylene glycol are even more preferred from the viewpoint of high solubility in water and ease of removal by washing.

[0198] In the method for producing polymer microparticles of the present invention, the solvent forming the poor solvent phase is not particularly limited, as long as it does not dissolve the resin that is the main component of the polymer microparticles but dissolves the water-soluble polymer. For example, the solvent is at least one of water and an alcohol. Such a solvent can be appropriately selected, and examples include alcohols such as methanol, ethanol, and isopropanol, as well as water. Of these, water is preferred from the perspective of preventing voids in the molded object caused by organic solvents.

[0199] In addition, for the emulsion obtained by the above-mentioned (a) step, in the above-mentioned (b) step, at least one of heating and decompression is performed under stirring to remove a part or all of the organic solvent contained in the emulsion. Thus, the polymer particles are precipitated. There is no particular limitation as a method for selectively removing only the organic solvent from the emulsion. Specifically, as this method, there can be cited a method of observing the temperature of the distilled liquid at any degree of decompression and monitoring the vapor temperature, a method of observing the degree of decompression and the temperature of the reaction tank and judging based on the vapor pressure curve of the solvent, a method of collecting the distilled liquid and analyzing it using GC, NMR, etc. In each of the above-mentioned methods, the relationship between the temperature and vapor pressure of each solvent can be calculated by the Antoine formula (see the revised 3rd edition of Chemical Handbook Basic Edition II p111-132, edited by the Chemical Society of Japan, Maruzen Co., Ltd.). Among them, from the viewpoint of being able to observe the evaporation behavior of the solvent, the method of observing the vapor temperature is preferred.

[0200] The polymer microparticle solution thus obtained can be separated by filtration into a solid such as polymer microparticles and a liquid such as a solution by a conventional solid-liquid separation method such as filtration. The obtained solid (wet solid) can then be washed with a solvent such as water as needed and subjected to a drying step to obtain the desired dry powder (polymer microparticles).

[0201] (Composition and optical components)

[0202] As one embodiment of the present invention, polymer particles are mixed with a binder resin, a solvent, an additive, etc. to prepare a composition comprising polymer particles. The composition to which the embodiment of the present invention relates (hereinafter, sometimes referred to as the composition of the present invention) for example comprises a binder resin and polymer particles of the present invention, and can be formed into a desired shape according to the applicable parts. For example, the composition formed by mixing polymer particles with a resin is formed into a sheet, a lens, or other three-dimensional shapes, so that a desired optical component can be produced. That is, the optical component to which the embodiment of the present invention relates (hereinafter, sometimes referred to as the optical component of the present invention) is a component comprising polymer particles of the present invention. As a molding method for the above-mentioned composition, as long as it is a method capable of molding into a desired shape, it is not particularly limited, and can include a method for coating and drying using a known coating method, a method for molding using an extruder, a three-dimensional stacking molding method based on a 3D printer, etc.

[0203] As a representative structural example of the optical component of the present invention, for example, Figures 4 to 6 Example shown. Figure 4 It is a schematic cross-sectional view showing a first example of an optical component according to an embodiment of the present invention. Figure 5 It is a schematic cross-sectional view showing a second example of the optical component according to the embodiment of the present invention. Figure 6 It is a schematic cross-sectional view showing a third example of the optical component according to the embodiment of the present invention.

[0204] like Figure 4 As shown in FIG. 1 , the optical component 1A of the first example includes polymer microparticles 2a and a support 3a containing the polymer microparticles 2a. Figure 4 As shown in FIG. 3 , polymer particles 2a are dispersed inside the support 3a. The polymer particles 2a are an example of the polymer particles of the present invention. Figure 4 In the illustrated structural example, the optical component 1A has a single-layer structure in which one type of polymer microparticles 2 a are dispersed within a single-layer support 3 a .

[0205] like Figure 5 As shown, the optical component 1B of the second example comprises: two polymer particles 2a, 2b; and a support 3a containing the two polymer particles 2a, 2b. Inside the support 3a, as shown in FIG. Figure 5 As shown in FIG, polymer particles 2a and polymer particles 2b are dispersed. Polymer particles 2a and polymer particles 2b are examples of polymer particles of the present invention. Figure 5In the illustrated structural example, the optical component 1B has a single-layer structure containing two types of polymer particles 2a and 2b dispersed within a single-layer support 3a. These polymer particles 2a and 2b have different optical properties, such as different luminescent colors.

[0206] like Figure 6 As shown, the optical component 1C of the third example comprises: two types of polymer particles 2a and 2b; and two layers of supports 3a and 3b containing the two types of polymer particles 2a and 2b, respectively. In the two layers of supports 3a and 3b, one type of polymer particles 2a is dispersed inside the support 3a on one side, and another type of polymer particles 2b is dispersed inside the support 3b on the other side. It should be noted that these polymer particles 2a and polymer particles 2b are the same as those of the optical component 1B of the second example described above. Figure 6 In the illustrated structural example, the optical component 1C has a laminated structure comprising a single-layer support 3a containing dispersed polymer particles 2a and a single-layer support 3b containing dispersed polymer particles 2b different from the polymer particles 2a.

[0207] Here, as a support (for example Figures 4 to 6 The material of the support 3a, 3b, etc. shown in the figure is not particularly limited, and known metals, resins, glass, ceramics, paper, etc. can be used. However, from the perspective of transparency and processability, the support is preferably formed from a resin.

[0208] A first example of the optical component of the present invention is a color conversion component that converts incident light into light of a different wavelength. The polymer microparticles of the present invention containing a luminescent material have low optical loss and excellent durability and can therefore be preferably used.

[0209] As a second example of the optical component of the present invention, a color conversion substrate having multiple color conversion layers on a transparent substrate can be cited. In the present invention, the color conversion layers preferably include a red conversion layer and a green conversion layer. The red conversion layer is formed from a phosphor material that absorbs at least blue light and emits red light. The green conversion layer is formed from a phosphor material that absorbs at least blue light and emits green light. In addition, the color conversion substrate may be formed with partitions, and the color conversion layer is preferably arranged between the partitions (in the recess). Such a color conversion substrate can be configured such that excitation light is incident from the transparent substrate side and the luminescent color can be visually recognized from the side opposite to the transparent substrate, or such that excitation light is incident from the color conversion layer side and the luminescent color can be visually recognized from the transparent substrate side. The quantum yield of the color conversion layer is generally 0.5 or greater, preferably 0.7 or greater, more preferably 0.8 or greater, and even more preferably 0.9 or greater when blue light with a peak wavelength of 440 nm to 460 nm is irradiated onto the color conversion substrate.

[0210] (light source)

[0211] The light source involved in the embodiment of the present invention is not particularly limited. For example, in principle, any excitation light source such as a fluorescent light source such as a hot cathode tube, a cold cathode tube, an inorganic electroluminescent (EL), an organic EL element light source, an LED light source, an incandescent light source, or sunlight can be used. Among these, an LED light source is a suitable light source. For example, in display and lighting applications, from the perspective of improving the color purity of blue light, a light emitting diode (blue LED light source) having a maximum luminescence within a wavelength range of 400 nm to 500 nm is a further suitable light source. Furthermore, as the light source, a blue LED light source having a maximum luminescence within a wavelength range of 430 nm to 480 nm is more preferred, and a blue LED light source having a maximum luminescence within a wavelength range of 450 nm to 470 nm is further preferred.

[0212] The light source may have one luminescence peak or two or more luminescence peaks. In order to improve color purity, it is preferred to have one luminescence peak. Alternatively, a plurality of light sources having different luminescence peaks may be used in any combination.

[0213] (Light source unit)

[0214] A light source unit according to an embodiment of the present invention (hereinafter sometimes referred to as the light source unit of the present invention) comprises: the aforementioned light source; and the polymer microparticles of the present invention or a component containing the polymer microparticles (e.g., the composition or optical component of the present invention). The light source unit of the present invention is useful for various light sources such as space lighting and backlighting. Specifically, the light source unit of the present invention can be used in applications such as displays, lighting devices, interior decoration, signage, and billboards, and is particularly suitable for use in displays and lighting devices.

[0215] (Displays, lighting devices)

[0216] A display according to an embodiment of the present invention includes at least the light source unit including the light source and polymer microparticles as described above. For example, the light source unit described above is used as a backlight unit in displays such as liquid crystal displays.

[0217] Furthermore, an illumination device according to an embodiment of the present invention includes at least the light source unit including the light source and polymer particles as described above. For example, the illumination device is configured to emit white light by combining a blue LED light source as the light source unit with polymer particles or a color conversion member including polymer particles that convert blue light from the blue LED light source into light with a longer wavelength.

[0218] (Ink)

[0219] The polymer microparticles of the present invention can also be used in inks. The inks related to the embodiments of the present invention (hereinafter sometimes referred to as the inks of the present invention) are composed of a liquid, gel, or solid state containing at least the polymer microparticles of the present invention, and are used for recording text, etc., and coloring surfaces. The polymer microparticles of the present invention have high sphericity and uniform shape. Therefore, by being applied to the inks of the present invention, the smoothness of the printed surface using the ink can be improved, and light scattering caused by surface irregularities can be suppressed. In addition, the polymer microparticles of the present invention are also excellent in durability. Therefore, by being applied to the inks of the present invention, it is possible to achieve long-term use of printed materials using the inks.

[0220] Example

[0221] The present invention will be described below with reference to Examples, but the present invention is not limited to the following Examples. First, the measurement methods, evaluation methods, compounds, and resins in Examples and Comparative Examples will be described.

[0222] [Compounds and resins]

[0223] In the following Examples and Comparative Examples, Compounds D-1 to D-5 were used as the light-emitting material or coloring material contained in the polymer microparticles. Compounds D-1 to D-5 are the compounds shown below.

[0224] [Chemical Formula 12]

[0225]

[0226] In the following Examples and Comparative Examples, resins P-1 to P-7 were used as the main component of the polymer fine particles. Resins P-1 to P-7 are the following resins.

[0227] Resin P-1: Polymethyl methacrylate-hydrogenated styrene copolymer resin "Optimas" (registered trademark) 7500 (manufactured by Mitsubishi Gas Chemical Co., Ltd., Tg = 120°C, a resin having a partial structure represented by general formula (1) and a partial structure represented by general formula (2))

[0228] Resin P-2: Polymethyl methacrylate-isobornyl methacrylate copolymer resin (Tg = 111°C)

[0229] Resin P-3: Polymethyl methacrylate-cyclohexyl methacrylate copolymer resin (Tg = 94°C)

[0230] Resin P-4: polystyrene resin ("SIGMA-ALDRICH" (registered trademark), product number 331651, Tg = 100°C)

[0231] Resin P-5: Polymethyl methacrylate resin BR-85 (manufactured by Mitsubishi Chemical Corporation, Tg = 105°C)

[0232] Resin P-6: polymethyl methacrylate-hydrogenated styrene copolymer resin (Tg = 120°C, a resin having a partial structure represented by the general formula (1) and a partial structure represented by the general formula (2))

[0233] Resin P-7: Polymethyl methacrylate-hydrogenated styrene copolymer resin (Tg = 123°C, a resin having a partial structure represented by the general formula (1) and a partial structure represented by the general formula (2))

[0234] Resin P-2 was synthesized by mixing methyl methacrylate and isobornyl methacrylate in a molar ratio of 85:15 and free radical polymerization using azobisisobutyronitrile according to a known method. Resin P-3 was synthesized by mixing methyl methacrylate and cyclohexyl methacrylate in a molar ratio of 80:20 and free radical polymerization in the same manner as Resin P-2. After polymerization, Resins P-2 and P-3 were each purified by precipitation in methanol and thoroughly dried before use.

[0235] Resins P-6 and P-7 were synthesized by the following methods. Specifically, methyl methacrylate and styrene were mixed in a molar ratio of 77:33, and methyl methacrylate and cyclohexyl methacrylate were mixed in a molar ratio of 32:68. Free radical polymerization using tert-amyl peroxide-2-ethylhexanoate was performed according to a known method to obtain a polymethyl methacrylate-styrene copolymer resin. Subsequently, a hydrogenation reaction using Pd / C was performed according to a known method to synthesize Resins P-6 and P-7, respectively. The synthesized Resins P-6 and P-7 were purified by adsorption removal using spherical silica gel and activated carbon, then purified by precipitation in methanol and thoroughly dried before use. 1 The results of H-NMR measurement showed that the proportions of methyl methacrylate structural units in Resin P-6 and Resin P-7 were 75 mol% and 30 mol%, respectively. Furthermore, the hydrogenation reaction rates of the benzene rings in Resin P-6 and Resin P-7 were both 99%.

[0236] [Measurement and evaluation methods]

[0237] (1) D50 particle size and D90 / D10 of polymer microparticles

[0238] In this measurement and evaluation method, a dispersion (preliminarily dispersed in approximately 5 mL of deionized water, approximately 100 mg of polymer microparticles) is added to a laser diffraction particle size distribution analyzer (Microtrac MT3300EX II) manufactured by Nikkiso Co., Ltd. until a measurable concentration is reached. Ultrasonic dispersion is then applied to the dispersion within the analyzer at an output power of 30 W for 60 seconds. The particle size distribution, measured for 10 seconds, at which the cumulative number of particles from the smaller particle size side reaches 50% is defined as the D50 particle size of the target polymer microparticles. Furthermore, the particle size at which the cumulative number of particles from the smaller particle size side reaches 10% is defined as the D10 particle size, and the particle size at which the cumulative number of particles from the smaller particle size side reaches 90% is defined as the D90 particle size. The D90 / D10 of the target polymer microparticles is calculated based on the ratio of these two values. It should be noted that the refractive index used during the measurement was 1.52, and the refractive index of the medium (deionized water) was 1.333.

[0239] (2) True sphericity of polymer particles

[0240] In this measurement and evaluation method, the sphericity of polymer microparticles is calculated by randomly observing 30 polymer microparticles from a photograph taken with a scanning electron microscope (JSM-6301NF) manufactured by JEOL Ltd., and calculating the sphericity from the minor and major axes of each of the 30 polymer microparticles using the following mathematical formula.

[0241] [Formula 4]

[0242]

[0243] In the above formula, S is the true sphericity of the polymer microparticles. a is the major axis of the observed polymer microparticles, and b is the minor axis of the polymer microparticles. n is the number of polymer microparticles measured. In this measurement and evaluation method, the number of measurements was set to 30 (n = 30).

[0244] (3) Linseed oil absorption of polymer particles

[0245] In this measurement and evaluation method, approximately 300 mg of polymer microparticles were accurately weighed onto a watch glass, and purified linseed oil (manufactured by Kanto Chemical Co., Ltd.) was slowly added dropwise using a burette in accordance with JIS K5101 (2004), "Testing Methods for Pigments - Purified Linseed Oil Method." The polymer microparticles and purified linseed oil were then kneaded with a palette knife. This process of dropwise addition and kneading of the purified linseed oil was repeated until a bulk sample was formed. The point at which the paste of the polymer microparticles and purified linseed oil became smooth and hard was defined as the endpoint. The linseed oil absorption (mL / 100 g) of the target polymer microparticles was calculated based on the amount of purified linseed oil added dropwise.

[0246] (4) Light transmittance of resin

[0247] In this measurement and evaluation method, a sample sheet of a resin having a film thickness of 20 μm or less is prepared and its light transmittance is measured using a commercially available measuring instrument (e.g., a UV-visible spectrophotometer (trade name: U-3010) manufactured by Hitachi, Ltd.). Based on the measured values, the minimum transmittance within the wavelength range of 400 nm to 800 nm is determined, and this minimum value is used as the measured light transmittance value of the target resin.

[0248] (5) Glass transition temperature of resin

[0249] In this measurement and evaluation method, a differential scanning calorimeter (DSCQ20) manufactured by TA Instruments is used to raise the temperature of the resin to be measured from 30°C at a rate of 20°C / minute under a nitrogen atmosphere to a temperature 30°C higher than the endothermic peak indicating the melting point of the resin. The DSC curve of the resin is thus obtained. In the resulting DSC curve, the temperature at the point where a straight line equidistant from the vertical axis, obtained by extending the baselines of the low and high temperature sides, intersects with the curve of the step-like change portion of the glass transition is taken as the glass transition temperature of the target resin. It should be noted that if the resin to be measured is an amorphous polymer that does not exhibit an endothermic peak at a melting point, the DSC curve of the resin is obtained by raising the temperature of the resin from 30°C to 300°C. The mass of the resin required for the measurement is approximately 8 mg.

[0250] (6) Molar absorptivity

[0251] In this measurement and evaluation method, the compound to be measured is subjected to 1×10 -5 The compounds were dissolved in a solvent (toluene for compounds D-1 to D-5) at a concentration of 1 mol / L, and their absorption spectra were measured using a U-3200 spectrophotometer (manufactured by Hitachi, Ltd.). From the obtained absorption spectra, the absorbance at the maximum absorption wavelength within a wavelength range of 300 nm or longer was determined, and the molar absorptivity of the compound was calculated together with the obtained absorbance.

[0252] (7) Fluorescence spectrum

[0253] In this measurement and evaluation method, the compound to be measured by fluorescence spectrum is subjected to 1×10 -6 The compound was dissolved in a solvent (toluene for compounds D-1 to D-5) at a concentration of 1 mol / L and its fluorescence spectrum was measured using a fluorescence spectrophotometer (Fluoromax4, manufactured by Horiba, Ltd.). The half-value width of emission was determined from the obtained fluorescence spectrum.

[0254] (8) Luminescence intensity of polymer particles

[0255] In this measurement and evaluation method, polymer microparticles mixed with a luminescent material or a coloring material (hereinafter, sometimes referred to as "luminescent coloring material") are sandwiched between glass cover plates, and a fluorescence spectrophotometer (Fluoromax4, manufactured by Horiba, Ltd.) is used to measure the luminescence spectrum of the polymer microparticles when the luminescent coloring material is excited at the maximum absorption wavelength in the wavelength range of 300 nm or more. At this time, the width of the slit on the excitation light side and the slit on the light receiving side are fixed so that the intensity of the excitation light is the same. Based on the luminescence spectrum measured as described above, the luminescence intensity of the polymer microparticles to be evaluated is obtained, and the obtained luminescence intensity is converted into a relative luminescence intensity relative to the luminescence intensity of the benchmark polymer microparticles (hereinafter referred to as relative luminescence intensity) for comparative evaluation. The evaluation results of the luminescence intensity of each polymer microparticle are shown in Tables 1 to 4 described later. In Table 1, the relative luminescence intensity of the polymer microparticles is represented by a relative value when the luminescence intensity of the polymer microparticles prepared in Example 1 is set to 100. In Table 2, the relative luminescence intensity of the polymer microparticles is expressed as a relative value when the luminescence intensity of the polymer microparticles prepared in Example 4 is set to 100. In Table 3, the relative luminescence intensity of the polymer microparticles is expressed as a relative value when the luminescence intensity of the polymer microparticles prepared in Example 8 is set to 100. In Table 4, the relative luminescence intensity of the polymer microparticles is expressed as a relative value when the luminescence intensity of the polymer microparticles prepared in Example 13 is set to 100.

[0256] (9) Durability of polymer particles

[0257] In this measurement and evaluation method, a sample containing polymer microparticles sandwiched between glass cover plates is placed on a planar light-emitting device equipped with a blue LED element (ProLight; model PM2B-3LBE-SD, peak emission wavelength: 460 nm). A current of 10 mA is passed through the blue LED element to illuminate it, and the initial intensity of the light emitted from the polymer microparticles is measured using a spectroradiometer (CS-1000, Konica Minolta). Subsequently, a current of 200 mA is passed through the planar light-emitting device to illuminate the blue LED element under an environment of 50°C and 27% RH. The sample is then continuously irradiated with light from the blue LED element, and the time it takes for the light emission intensity of the polymer microparticles to decrease by 10% is measured. This time is used to evaluate the durability (light durability) of the polymer microparticles. The brightness is measured after the sample and planar light-emitting device are removed from the oven and cooled to room temperature.

[0258] (10) 1 H-NMR determination

[0259] In this measurement and evaluation method, 1H-NMR was measured using a superconducting FTNMR EX-270 (manufactured by JEOL Ltd.) in a deuterated chloroform solution.

[0260] (11) Solvent content in polymer particles

[0261] In this measurement and evaluation method, a sample is prepared by dissolving the target polymer microparticles (20 mg) in 2 mL of NMP or THF. The solvent content in the sample is measured using a Shimadzu Corporation gas chromatograph (GC-2010) under the following conditions. The solvent used to dissolve the polymer microparticles can be appropriately changed depending on the target.

[0262] <Condition>

[0263] Detector: FID

[0264] Column used: CP-Select 624CB

[0265] Detector temperature: 280°C

[0266] Carrier gas: He

[0267] Carrier gas flow rate: 6mL / min

[0268] Heating conditions: After maintaining at 40°C for 4 minutes, increase the temperature to 260°C at a heating rate of 8°C / min, and then maintain for 16 minutes

[0269] (12) Content of polymerization initiator and its decomposition products in polymer particles

[0270] In this measurement and evaluation method, a sample is prepared by dissolving the target polymer microparticles (20 mg) in 2 mL of NMP or THF. The content of the polymerization initiator and its decomposition products in the sample is measured using a Shimadzu Corporation gas chromatograph (GC-2010) under the same conditions as those for the solvent content measurement described in (11) above. The solvent in which the polymer microparticles are dissolved can be appropriately changed depending on the target object.

[0271] (13) Intrinsic birefringence of resin

[0272] In this measurement and evaluation method, the dielectric polarization difference of each bonding unit of the structural unit of the target resin is calculated using a molecular orbital method such as the AM1 method or the PM3 method, and the intrinsic birefringence value is calculated as the volume average using the following Lorentz-Lorenz equation.

[0273] [Formula 5]

[0274] Δn0=2 / 9π×(n 2 +2) 2 / n×ΔP·d·N / M

[0275] It should be noted that in the above formula, Δn0: intrinsic birefringence value, ΔP: difference between the dielectric polarizability in the axial direction of the molecular chain and the dielectric polarizability in the direction perpendicular to the molecular chain axis, n: refractive index, d: density, N: Avogadro constant, and M: molecular weight.

[0276] [Example 1]

[0277] In Example 1, 45 g of resin P-1, which is the main component of the polymer microparticles, 21 mg of compound D-1, which is the luminescent material, and 255 g of ethyl acetate, which is the solvent, were mixed to prepare a 15 wt% polymer solution. In addition, polyvinyl alcohol (GL-05, manufactured by Nippon Synthetic Chemical Co., Ltd.) (42 g) was dissolved in water (258 g) to prepare a 14 wt% polyvinyl alcohol aqueous solution. Next, the polymer solution and the polyvinyl alcohol aqueous solution were added to a 1 L tank, and the mixture was stirred at a temperature of 40°C and a speed of 300 rpm. Thus, an emulsion was obtained in the 1 L tank. Then, a diaphragm pump was used to reduce the pressure in the 1 L tank in stages to 200 hPa. After the pressure reached 200 hPa, the pressure was further reduced for 1 hour to remove the organic solvent in the emulsion, thereby obtaining a polymer microparticle slurry.

[0278] Next, the solvent and the polyvinyl alcohol aqueous solution were removed from the polymer microparticle slurry by centrifugal separation and decantation of the supernatant. Then, the slurry was made again with water, and after washing with warm water at a temperature of 80°C for 1 hour, it was filtered to remove impurities in the particles and obtain a polymer microparticle filter cake. The polymer microparticle filter cake was dried under reduced pressure, and as a result, the polymer microparticles of Example 1 were obtained. The properties (microparticle properties) and material properties of the obtained polymer microparticles are shown in Table 1. In addition, the obtained polymer microparticles were placed on a conductive tape and platinum vapor-deposited. The polymer microparticles were photographed at a magnification of 5000 times using a scanning electron microscope (JSM-6301NF) manufactured by JEOL Ltd. The photograph of the polymer microparticles of Example 1 thus obtained is shown in FIG. Figure 1 shown.

[0279] [Example 2]

[0280] In Example 2, polymer microparticles were prepared in the same manner as in Example 1, except that resin P-2 was used as the main component resin of the polymer microparticles. Table 1 shows the properties and material properties of the obtained polymer microparticles of Example 2.

[0281] [Example 3]

[0282] In Example 3, polymer microparticles were prepared in the same manner as in Example 1, except that resin P-3 was used as the main component of the polymer microparticles. Table 1 shows the properties and material properties of the obtained polymer microparticles of Example 3.

[0283] [Comparative Example 1]

[0284] In Comparative Example 1, 15 g of the resin P-1, which is the main component of the polymer microparticles, and 7.0 mg of the compound D-1, which is the luminescent material, were melt-kneaded at 270°C using a micro-kneading extruder A300 (manufactured by Imoto Manufacturing Co., Ltd.) to obtain a mixture thereof. The obtained mixture was formed into pellets and then freeze-pulverized using a freeze grinder. Thus, the polymer microparticles of Comparative Example 1 were prepared. The properties and material properties of the obtained polymer microparticles are shown in Table 1. In addition, as in Example 1, the polymer microparticles of Comparative Example 1 were photographed at a magnification of 200 times using a scanning electron microscope. The photograph of the polymer microparticles of Comparative Example 1 obtained is shown in FIG. Figure 2 shown.

[0285] [Comparative Example 2]

[0286] In Comparative Example 2, resin P-1 was used as the main component of the resin for the polymer microparticles, and compound D-1 was used as the luminescent material. Resin P-1 (15 g), compound D-1 (7.0 mg) and toluene (60 g) as the solvent were mixed. Using a planetary stirring and degassing device "MAZERUSTAR KK-400" (manufactured by Kurabo Co., Ltd.), the mixed solution was stirred and degassed at 300 rpm for 30 minutes. The mixed solution was dried by a spray drying method to prepare polymer microparticles of Comparative Example 2. The properties and material properties of the obtained polymer microparticles are shown in Table 1. In addition, as in Example 1, the polymer microparticles of Comparative Example 2 were photographed at a magnification of 5000 times using a scanning electron microscope. The photograph of the polymer microparticles of Comparative Example 2 obtained is shown in FIG. Figure 3 shown.

[0287] [Comparative Example 3]

[0288] In Comparative Example 3, polymer microparticles were prepared in the same manner as in Example 1, except that resin P-4 was used as the main component resin of the polymer microparticles. Table 1 shows the properties and material properties of the polymer microparticles obtained in Comparative Example 3.

[0289] [Comparative Example 4]

[0290] In Comparative Example 4, polymer microparticles were prepared in the same manner as in Example 1, except that resin P-5 was used as the main component resin of the polymer microparticles. Table 1 shows the properties and material properties of the obtained polymer microparticles of Comparative Example 4.

[0291] [Examples 4 to 7]

[0292] In Examples 4 to 7, polymer microparticles were prepared using the same method as in Example 1, except that compounds D-2 to D-5, respectively, were used instead of compound D-1 as the luminescent material. The amount of luminescent material added was adjusted to maintain the same mass of the resulting polymer microparticles. In each of Examples 4 to 7, polymer microparticles with high sphericity and smooth surfaces were obtained, similar to Example 1, despite the changes in the luminescent material used. The properties and material properties of the resulting polymer microparticles are shown in Table 2.

[0293] [Example 8]

[0294] In Example 8, a polymer microparticle cake was obtained in the same manner as in Example 1, except that resin P-6 was used as the main component resin of the polymer microparticles. The polymer microparticle cake was then dried under reduced pressure at 50°C for 8 hours to obtain polymer microparticles of Example 8. The properties and material properties of the obtained polymer microparticles are shown in Table 3.

[0295] [Example 9]

[0296] In Example 9, polymer microparticles were prepared in the same manner as in Example 8, except that the drying conditions for the polymer microparticle cake were changed to drying under reduced pressure at 50°C for 2 hours. The properties and material properties of the obtained polymer microparticles of Example 9 are shown in Table 3.

[0297] [Example 10]

[0298] In Example 10, polymer microparticles were prepared in the same manner as in Example 9, except that the solvent was changed to a mixed solvent of ethyl acetate and butyl acetate in a mixing ratio (ethyl acetate / butyl acetate) of 90 / 10. The properties and material properties of the obtained polymer microparticles of Example 10 are shown in Table 3.

[0299] [Example 11]

[0300] In Example 11, polymer microparticles were prepared in the same manner as in Example 8, except that 45 mg of azobisisobutyronitrile was mixed in addition to the resin, light-emitting material, and solvent. Table 3 shows the properties and material properties of the obtained polymer microparticles of Example 11.

[0301] [Example 12]

[0302] In Example 12, polymer microparticles were prepared in the same manner as in Example 11, except that 80 mg of azobisisobutyronitrile was added. Table 3 shows the properties and material properties of the obtained polymer microparticles of Example 12.

[0303] Comparison of Examples 8 to 12 reveals that the lower the content of the solvent, the content of the polymerization initiator, and the content of its decomposition product in the polymer fine particles, the better the durability of the polymer fine particles.

[0304] [Example 13]

[0305] In Example 13, polymer microparticles were prepared in the same manner as in Example 8, except that Compound D-2 was used instead of Compound D-1 as the luminescent / coloring material. The amount of Compound D-2 was adjusted so that the resulting polymer microparticles had the same mass. The properties and material properties of the resulting polymer microparticles of Example 13 are shown in Table 4.

[0306] [Example 14]

[0307] In Example 14, polymer microparticles were prepared in the same manner as in Example 13, except that resin P-7 was used as the main component resin of the polymer microparticles. Table 4 shows the properties and material properties of the obtained polymer microparticles of Example 14.

[0308] Comparing Example 13 with Example 14, it can be seen that even when the same type of structural unit resin is used, the resin with smaller intrinsic birefringence has smaller optical loss due to light diffusion and higher luminous intensity.

[0309] [Table 1]

[0310]

[0311] Table 2

[0312]

[0313] [Table 3]

[0314]

[0315] [Table 4]

[0316] (Table 4)

[0317]

[0318] Comparison between Example 1 and Comparative Examples 1 and 2 reveals that the polymer microparticles of Example 1 having a higher sphericity are superior to those of the polymer microparticles of Comparative Examples 1 and 2 in both relative luminescence intensity and durability.

[0319] Comparison of Example 1 with Comparative Example 3 shows that the polymer microparticles of Example 1, which use a resin P-1 having a molecular structure having at least one ring structure selected from the group consisting of an aliphatic hydrocarbon ring, an aliphatic heterocycle, and a ring containing sp3 carbon, have superior durability compared to the polymer microparticles of Comparative Example 3.

[0320] Furthermore, a comparison of Examples 1 to 3 reveals that the polymer microparticles of Example 1 using resin P-1, which is at least one of a resin having the aforementioned ring structure in its polymer main chain and a resin having the aforementioned ring structure directly linked to its polymer main chain, exhibit particularly excellent durability.

[0321] Industrial applicability

[0322] As described above, the polymer microparticles, the production method thereof, the composition, the optical component, the light source unit, the display and lighting device, and the ink according to the present invention are suitable for achieving both improved durability and reduced optical loss.

[0323] Description of Reference Numerals

[0324] 1A, 1B, 1C optical components

[0325] 2a, 2b polymer microparticles

[0326] 3a, 3b Support body

Claims

1. Polymer microparticles comprising a resin as a main component and containing a luminescent material or a coloring material, characterized in that: The true sphericity of the polymer particles is 80 or more and 100 or less, The resin has at least one ring structure selected from the group consisting of an aliphatic hydrocarbon ring, an aliphatic heterocycle, and a ring containing sp3 carbon in its molecular structure.

2. The polymer microparticles according to claim 1, wherein The oil absorption of linseed oil is not less than 1 mL / 100 g and not more than 200 mL / 100 g.

3. The polymer microparticles according to claim 1, wherein The ratio of the D90 particle size to the D10 particle size in the particle size distribution of the polymer fine particles, ie, D9 particle size / D10 particle size, is 1 or more and 5 or less.

4. The polymer microparticles according to claim 1, wherein The content of the solvent in the polymer microparticles is less than 1 wt %.

5. The polymer microparticles according to claim 1, wherein The content of the polymerization initiator and its decomposition products in the polymer microparticles is less than 0.1 wt %.

6. The polymer microparticles according to claim 1, wherein The resin has a glass transition temperature of 100° C. or higher.

7. The polymer microparticles according to claim 1, wherein The resin is at least one of a resin having the ring structure in a polymer main chain and a resin in which the ring structure is directly linked to a polymer main chain.

8. The polymer microparticles according to claim 1, wherein The resin is a resin having a partial structure represented by the general formula (1) and a partial structure represented by the general formula (2) in its molecular structure, [Chemical Formula 1] In the general formula (1), Y 1 and Y 2 They may be the same or different and are hydrogen atoms or organic groups having 1 to 20 carbon atoms; in the general formula (2), Y 3 ~Y 6 They may be the same or different and are hydrogen atoms or organic groups having 1 to 20 carbon atoms, and Y 3 ~Y 6 At least one of them is a group containing an aliphatic cyclic hydrocarbon structure.

9. The polymer microparticles according to claim 8, wherein Y in the general formula (2) 3 ~Y 6 At least one of them is a substituted or unsubstituted cyclohexyl group.

10. The polymer microparticles according to claim 8, wherein Y in the general formula (2) 3 ~Y 6 One of them is a substituted or unsubstituted cyclohexyl group, and the other three are hydrogen atoms.

11. The polymer microparticles according to claim 1, wherein The resin has a light transmittance of 85% or more within a wavelength range of 400 nm to 800 nm and an intrinsic birefringence of -30×10 -4 Above+30×10 -4 The following resins.

12. The polymer microparticles according to claim 1, wherein The luminescent material or the coloring material is an organic pigment or an organic dye.

13. The polymer microparticles according to claim 1, wherein The luminescent material or the coloring material includes at least one material having a molar absorption coefficient of 10,000 M at a maximum absorption wavelength in a wavelength range of 300 nm or more. -1 cm -1 More than organic materials.

14. The polymer microparticles according to claim 1, wherein Containing at least one of the luminescent materials, The half-value width of the luminescence spectrum of the luminescent material is less than 60 nm.

15. A composition characterized in that Include: binder resin; and The polymer microparticles according to any one of claims 1 to 14.

16. An optical component, characterized in that The invention comprises the polymer microparticles according to any one of claims 1 to 14.

17. A light source unit, characterized in that have: light source; and The polymer microparticles according to any one of claims 1 to 14.

18. A display, characterized in that A light source unit according to claim 17 is provided.

19. A lighting device, characterized in that A light source unit according to claim 17 is provided.

20. Ink, characterized in that The invention comprises the polymer microparticles according to any one of claims 1 to 14.

21. A method for producing polymer microparticles, characterized in that: The following steps (a) and (b) are carried out in sequence. (a) forming an emulsion comprising two phases: a polymer phase and a poor solvent phase, wherein the polymer phase comprises an organic solvent and a resin having at least one ring structure selected from the group consisting of an aliphatic hydrocarbon ring, an aliphatic heterocycle, and a ring containing an sp3 carbon, and the poor solvent phase comprises at least one of water and an alcohol and a water-soluble polymer; Step (b): a step of at least one of heating and reducing the pressure of the emulsion while stirring to remove a portion or all of the organic solvent contained in the emulsion to precipitate polymer microparticles.

22. The method for producing polymer microparticles according to claim 21, wherein: The water-soluble polymer is at least one selected from the group consisting of polyvinyl alcohol, poly(vinyl alcohol-ethylene) copolymer, polyethylene glycol, cellulose derivatives, and polyvinyl pyrrolidones.

23. The method for producing polymer microparticles according to claim 21, wherein The step (a) and the step (b) do not include a polymerization step.

24. The method for producing polymer microparticles according to claim 21, wherein The resin is at least one of a resin having the ring structure in a polymer main chain and a resin in which the ring structure is directly linked to a polymer main chain.

25. The method for producing polymer microparticles according to claim 21, wherein The resin has a light transmittance of 85% or more within a wavelength range of 400 nm to 800 nm and an intrinsic birefringence of -30×10 -4 Above+30×10 -4 The following resins.

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