Luminescent materials and their applications

Abstract

The present invention addresses the problem of easily achieving further enhancement of the degree of circular polarization of emission and the luminous intensity; and the present invention provides a light emitting material which contains a luminescent molecule or a luminescent metal complex, and at least one salt that is selected from the group consisting of an ammonium salt represented by general formula (1), a pyrrolidinium salt represented by general formula (2), an imidazolium salt represented by general formula (3) and a pyridinium salt represented by general formula (4). (In the formulae, each of R1 to R11 independently represents a linear or branched alkyl group having 1 to 20 carbon atoms, or the like; X- represents a carboxylic acid anion or the like; n represents an integer of 1 to 3; and m represents an integer of 1 to 5.)

Claims

[Claim 1] Luminescent metal complexes, At least one salt selected from the group consisting of ammonium salts represented by the following general formula (1), pyrrolidinium salts represented by the following general formula (2), imidazolium salts represented by the following general formula (3), and pyridinium salts represented by the following general formula (4), Includes, 【Chemistry 1】 (In the formula, R １ ~R １１ These represent, independently of each other, a linear or branched alkyl group having 1 to 20 carbon atoms, or an arylalkyl group having 7 to 20 carbon atoms. X － (where n represents a carboxylate anion, a fluorine-substituted alkyl carboxylate anion, a nitrate anion, a sulfonate anion, a fluorine-substituted alkyl sulfonate anion, a phosphate anion, a monoalkyl phosphate anion, a dialkyl phosphate anion, or a sulfate anion; where n is an integer from 1 to 3, and m is an integer from 1 to 5.) The luminescent metal complex is a rare earth complex represented by Ln, The ligand of the luminescent metal complex is at least one selected from the group consisting of β-diketonate ligands and ligands represented by the following general formula (5). 【Chemistry 2】 (In the formula, R12 represents a linear or branched perfluoroalkyl group having 1 to 5 carbon atoms, and each of the R13s independently represents a linear or branched alkyl group having 1 to 5 carbon atoms. Luminescent material. [Claim 2] The luminescent material according to claim 1, wherein Ln of the rare earth complex is Nd, Sm, Eu, Tb, Yb, Pr, Ce, Dy, Er, or Tm. [Claim 3] It further contains nucleic acid molecules, The nucleic acid molecule forms a lipid complex with at least one cation selected from the group consisting of an ammonium cation represented by the following general formula (1a), a pyrrolidinium cation represented by the following general formula (2a), an imidazolium cation represented by the following general formula (3a), and a pyridinium cation represented by the following general formula (4a). The luminescent material according to claim 1, comprising a composite of the luminescent metal complex, the lipid complex, and the salt. 【Transformation 3】 (In the formula, R １ ~R １１ (Each element independently represents a linear or branched alkyl group having 1 to 20 carbon atoms, or an arylalkyl group having 7 to 20 carbon atoms; n represents an integer from 1 to 3; and m represents an integer from 1 to 5.) [Claim 4] X － The luminescent material according to claim 1, wherein the carbon atom is a carboxylate anion having 10 or less carbon atoms, an alkyl carboxylate anion having 10 or less carbon atoms substituted with a fluorine atom, an alkyl sulfonate anion having 10 or less carbon atoms substituted with a fluorine atom, or a dialkyl phosphate anion. [Claim 5] The luminescent material according to claim 1, further comprising water and a solvent containing at least one linear or branched alcohol having 2 to 10 carbon atoms. [Claim 6] The light-emitting material according to claim 5, wherein the solvent is a linear or branched alcohol having 3 to 6 carbon atoms. [Claim 7] Luminescent metal complexes, A polymer anionic salt of at least one cation selected from the group consisting of ammonium cations, pyrrolidinium cations, imidazolium cations, and pyridinium cations, The luminescent metal complex is a rare earth complex represented by Ln, The ligand of the luminescent metal complex is at least one selected from the group consisting of β-diketonate ligands and ligands represented by the following general formula (5). A light-emitting material in which the polymer anion is a polyacrylate anion, a polymethacrylate anion, a polysulfate anion, or a polysulfonic acid anion. 【Chemistry 4】 (In the formula, R12 represents a linear or branched perfluoroalkyl group having 1 to 5 carbon atoms, and each of the R13s independently represents a linear or branched alkyl group having 1 to 5 carbon atoms. [Claim 8] Luminescent metal complexes, A polymer cation carboxylate, polymer cation nitrate, polymer cation sulfonate, or polymer cation sulfate is included. The luminescent metal complex is a rare earth complex represented by Ln, The ligand of the luminescent metal complex is at least one selected from the group consisting of β-diketonate ligands and ligands represented by the following general formula (5). A light-emitting material in which the polymer cation is a polycation that is a polyimine or polyamine, or a polyammonium cation. 【Transformation 5】 (In the formula, R12 represents a linear or branched perfluoroalkyl group having 1 to 5 carbon atoms, and each of the R13s independently represents a linear or branched alkyl group having 1 to 5 carbon atoms. [Claim 9] A method for manufacturing a film containing a light-emitting material, A step of preparing a precursor solution by dissolving the luminescent material according to claim 1 or 3 in a solvent, The steps of applying the precursor solution onto a substrate, and A method for manufacturing a film, comprising the step of drying the precursor solution coated on the substrate. [Claim 10] A circularly polarized light-emitting material comprising the light-emitting material according to claim 1 or 3, which is in the form of a solution or a film. [Claim 11] A security ink comprising the light-emitting material described in claim 1 or 3. [Claim 12] A printed material comprising a printed layer using the security ink described in claim 11. [Claim 13] An identification mark comprising a printed layer using the security ink described in claim 11. [Claim 14] A circularly polarizing filter comprising the circularly polarizing light-emitting material described in claim 10. [Claim 15] In luminescent metal complexes, This includes adding at least one salt selected from the group consisting of an ammonium salt represented by the following general formula (1), a pyrrolidinium salt represented by the following general formula (2), an imidazolium salt represented by the following general formula (3), and a pyridinium salt represented by the following general formula (4). 【Transformation 6】 (In the formula, R １ ~R １１ These represent, independently of each other, a linear or branched alkyl group having 1 to 20 carbon atoms, or an arylalkyl group having 7 to 20 carbon atoms. X － represents a carboxylic acid anion, an alkyl carboxylic acid anion substituted with a fluorine atom, a nitrate anion, a sulfonic acid anion, an alkyl sulfonic acid anion substituted with a fluorine atom, a phosphate anion, a monoalkyl phosphate anion, a dialkyl phosphate anion, or a sulfate anion; n represents an integer of 1 to 3; and m represents an integer of 1 to 5.) The luminescent metal complex is a rare earth complex represented by Ln, The ligand of the luminescent metal complex is at least one selected from the group consisting of β-diketonate ligands and ligands represented by the following general formula (5). 【Transformation 7】 (In the formula, R12 represents a linear or branched perfluoroalkyl group having 1 to 5 carbon atoms, and each of the R13s independently represents a linear or branched alkyl group having 1 to 5 carbon atoms. Methods for increasing luminescence intensity. [Claim 16] In luminescent metal complexes, This includes adding at least one salt selected from the group consisting of an ammonium salt represented by the following general formula (1), a pyrrolidinium salt represented by the following general formula (2), an imidazolium salt represented by the following general formula (3), and a pyridinium salt represented by the following general formula (4). 【Transformation 8】 (In the formula, R １ ~R １１ These represent, independently of each other, a linear or branched alkyl group having 1 to 20 carbon atoms, or an arylalkyl group having 7 to 20 carbon atoms. X － (where n represents a carboxylate anion, a fluorine-substituted alkyl carboxylate anion, a nitrate anion, a sulfonate anion, a fluorine-substituted alkyl sulfonate anion, a phosphate anion, a monoalkyl phosphate anion, a dialkyl phosphate anion, or a sulfate anion; where n is an integer from 1 to 3, and m is an integer from 1 to 5.) The luminescent metal complex is a rare earth complex represented by Ln, The ligand of the luminescent metal complex is at least one selected from the group consisting of β-diketonate ligands and ligands represented by the following general formula (5). 【Chemistry 9】 (In the formula, R12 represents a linear or branched perfluoroalkyl group having 1 to 5 carbon atoms, and each of the R13s independently represents a linear or branched alkyl group having 1 to 5 carbon atoms. A method for increasing the circular polarization degree of emitted light.

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