Aggregation-induced light-emitting mixture and use thereof

Abstract

An aggregation-induced light-emitting mixture, which comprises an organic compound H having an aggregation-induced light-emitting property and a light-emitting body E having a narrow light-emitting spectrum, wherein the organic compound H has a relatively high aggregation-state fluorescence luminescence efficiency. In addition, the present invention further relates to an organic light-emitting device comprising a color conversion layer, and the color conversion layer comprises the induction light-emitting mixture, wherein the organic compound H absorbs light of an excitation light source and transfers energy to the light-emitting body E, and the light-emitting body E emits emergent light having a relatively narrow half-peak width after absorbing the energy of the organic compound H. The light-emitting device having a narrow half-peak width can be used for manufacturing a display device having a high color gamut.

Description

A mixture and its application in the photoelectric field Technical Field

[0001] The present invention relates to the technical field of organic optoelectronic materials and devices, and in particular to a mixture, a composition containing the mixture, an organic functional material film, a optoelectronic device, an organic light-emitting device and applications thereof in the optoelectronic field. Background Art

[0002] According to the principles of colorimetry, the narrower the half-width at half-maximum of light entering the human eye, the higher the color purity and the brighter the color. Display devices made with red, green, and blue primary colors with narrow half-width at half-maximum display a wide color gamut, realistic images, and high-quality images.

[0003] Currently, there are two mainstream methods for achieving full-color displays. The first involves display devices actively emitting light in the three primary colors of red, green, and blue, a typical example being RGB-OLED displays. The currently mature technology uses vacuum evaporation with fine metal masks to produce three-color light-emitting devices. This process is complex, costly, and difficult to achieve high-resolution displays exceeding 600ppi. The second method uses a color converter to convert the single-color light emitted by the light-emitting device into multiple colors, thereby achieving full-color display. For example, Samsung's blue OLED combined with red and green quantum dot (QD) films acts as a color converter. The light-emitting device in this method features simple manufacturing processes and high yield rates. Furthermore, the color converter can be implemented through various technologies, such as evaporation, inkjet printing, transfer printing, and photolithography. This allows for applications in display products with varying resolution requirements, ranging from as low as 50ppi for large-screen TVs to over 3000ppi for silicon-based microdisplays.

[0004] Currently, there are two main types of color-conversion materials used in mainstream color converters. One is inorganic nanocrystals, commonly known as quantum dots. These are nanoparticles (specifically quantum dots) of inorganic semiconductor materials (such as InP, CdSe, CdS, and ZnSe) with diameters ranging from 2nm to 8nm. Due to the limitations of current quantum dot synthesis and separation technologies, the half-width (FWHM) of the emission peak of Cd-containing quantum dots is currently between 25nm and 40nm, with color purity that meets NTSC display requirements. The FWHM of Cd-free quantum dots is between 35nm and 75nm. However, due to the generally low extinction coefficient of quantum dots, thicker films—typically over 10 microns—are required to achieve adequate absorption of blue light. This poses a significant challenge to mass production, particularly for Samsung's blue OLED technology with red and green quantum dots. The second type is organic dyes, including various organic conjugated small molecules with chromophores. These organic dyes generally have higher extinction coefficients than quantum dots, but due to intramolecular thermal relaxation and the high vibrational energy within the organic molecules, the emission peaks of these materials are broader, typically exceeding 60nm. In addition, organic dyes generally suffer from concentration quenching, which causes the quantum efficiency of organic dyes to drop sharply at high concentrations.

[0005] Previous patent applications by the present inventors have disclosed color converters with a host-guest combination, where the host has a high extinction coefficient and the guest has a narrow luminescence spectrum. This provides a new design approach for developing thinner color converters. However, the luminescence efficiency of the aggregated state of the host material still needs to be significantly improved. Summary of the Invention

[0006] Based on this, the object of the present invention is to provide a mixture and its application in the optoelectronic field.

[0007] The specific technical solutions are as follows:

[0008] The present invention provides a mixture comprising an organic compound H and a luminophore E, wherein 1) the organic compound H is an aggregation-induced emission material, and its emission spectrum is on the short-wavelength side of the absorption spectrum of the luminophore E and at least partially overlaps with each other; 2) the full width at half maximum (FWHM) of the emission spectrum of the luminophore E is less than or equal to 55 nm.

[0009] In the above mixture, the organic compound H contained therein comprises at least one structure selected from the group consisting of chemical formulas (I-1) to (I-5):

[0010] in:

[0011] R1-R4, R8 are substituents, up to 5 on each benzene ring, which may be the same or different at each occurrence and are selected from linear alkyl, alkenyl, haloalkyl, alkoxy or thioalkoxy groups having 1 to 20 carbon atoms, or branched or cyclic alkyl, haloalkyl, alkoxy, thioalkoxy or silyl groups having 3 to 20 carbon atoms, or keto groups having 1 to 20 carbon atoms, or alkoxycarbonyl groups having 2 to 20 carbon atoms, or aromatic hydrocarbons having 4 to 20 carbon atoms. an oxycarbonyl group, or a cyano group, a carbamoyl group, a haloformyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, a CF3 group, a Cl group, a Br group, a F group, an I group, a crosslinkable group, or a substituted or unsubstituted aromatic or heteroaromatic ring system having 5 to 40 ring atoms, or an aryloxy group or heteroaryloxy group having 5 to 40 ring atoms, or an arylamine group or heteroarylamine group having 5 to 40 ring atoms, a disubstituted unit at any position of the above groups, or a combination of these groups.

[0012] R5-R7, at each occurrence, may be identical or different and be selected from H, D, or a linear alkyl, alkenyl, haloalkyl, alkoxy or thioalkoxy group having 1 to 20 carbon atoms, or a branched or cyclic alkyl, haloalkyl, alkoxy, thioalkoxy or silyl group having 3 to 20 carbon atoms, or a keto group having 1 to 20 carbon atoms, or an alkoxycarbonyl group having 2 to 20 carbon atoms, or an aryloxycarbonyl group having 4 to 20 carbon atoms , or cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, CF3, Cl, Br, F, I, a crosslinkable group, or a substituted or unsubstituted aromatic or heteroaromatic ring system having 5 to 40 ring atoms, or an aryloxy or heteroaryloxy group having 5 to 40 ring atoms, or an arylamine or heteroarylamine group having 5 to 40 ring atoms, a disubstituted unit at any position of the above groups, or a combination of these groups;

[0013] n is selected from integers of 0-5, and m is selected from integers of 0-4.

[0014] The present invention also provides a composition comprising a mixture as described above, and at least one organic resin and / or a solvent.

[0015] The present invention also provides an organic functional material film, which comprises a mixture as described above, or is prepared using a composition as described above.

[0016] The present invention also provides a photoelectric device comprising the above-mentioned mixture or organic functional material film.

[0017] The present invention also provides an organic light-emitting device, which comprises, from bottom to top, a first electrode, an organic light-emitting layer, a second electrode, a color conversion layer and an encapsulation layer, wherein the second electrode is at least partially transparent, and the color conversion layer at least partially absorbs light emitted by the organic light-emitting layer that passes through the second electrode; the color conversion layer comprises a mixture as described above, or is prepared using a composition as described above.

[0018] Advantageous Effects: According to the mixture of the present invention, the organic compound H exhibits aggregation-induced emission (AIE) and has a high fluorescence quantum efficiency (PLQY) in the aggregated state. Simultaneously, the luminophore E has a narrow emission spectrum, thereby realizing a high-efficiency, narrow-spectrum color conversion device. BRIEF DESCRIPTION OF THE DRAWINGS

[0019] Figure 1: Schematic diagram of a red, green, and blue color display device;

[0020] Figure 2: Absorption and emission spectra of toluene solution of compound 1;

[0021] Figure 3: Absorption and emission spectra of a thin film of compound 1;

[0022] Figure 4: Absorption and emission spectra of a toluene solution of compound E1;

[0023] Figure 5: (a) Emission spectra of compound 1 in H2O / THF solvents with different H2O volume fractions; (b) Relationship between the emission peak intensity of compound 1 solution and H2O volume fraction; (c) Images of compound 1 in H2O / THF solvents with different H2O volume fractions under UV illumination;

[0024] Figure 6: Absorption attenuation of toluene solution of compound 1 after UV irradiation;

[0025] Figure 7: Absorption attenuation of a toluene solution of compound E1 after UV irradiation;

[0026] Figure 8: Spectrum of top-emitting blue OLED + red CCL resin. DETAILED DESCRIPTION

[0027] To facilitate understanding of the present invention, the present invention will be described more fully below with reference to the accompanying drawings. Preferred embodiments of the present invention are shown in the accompanying drawings. However, the present invention may be implemented in many different forms and is not limited to the embodiments described herein. Rather, these embodiments are provided to provide a more thorough and comprehensive understanding of the present disclosure.

[0028] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by those skilled in the art to which this invention pertains. The terms used herein in the specification of the present invention are for the purpose of describing specific embodiments only and are not intended to limit the present invention. The term "and / or" as used herein includes any and all combinations of one or more of the associated listed items.

[0029] In the description of the embodiments of the present invention, a numerical range represented by “~” refers to a range that includes the numerical values ​​described before and after “~” as the lower limit and the upper limit.

[0030] In the description of the embodiments of the present invention, a substituent may be further substituted by a substituent, and "substituted group a" may refer to group a being substituted by a substituent, and the substituent may be substituted by at least one further substituent or may be unsubstituted.

[0031] In the present invention, "at least one" means one or more, and "plurality" means two or more. "At least one of the following" or similar expressions refers to any combination of these items, including any combination of single items or plural items. For example, "at least one of a, b, or c" or "at least one of a, b, and c" can all mean: a, b, c, ab (i.e., a and b), ac, bc, or abc, where a, b, and c can each be single or plural.

[0032] It should be understood that in various embodiments of the present invention, the size of the serial numbers of the above-mentioned processes does not mean the order of execution. Some or all of the steps can be executed in parallel or sequentially. The execution order of each process should be determined by its function and internal logic, and should not constitute any limitation on the implementation process of the embodiments of the present invention.

[0033] The terms used in the embodiments of the present invention are only for the purpose of describing specific embodiments and are not intended to limit the present invention. The singular forms "a", "an", "the" and "the" used in the embodiments of the present invention and the appended claims are also intended to include plural forms unless the context clearly indicates otherwise.

[0034] The term "OLED" is an abbreviation for "Organic Light Emitting Diode," which stands for organic electroluminescent diode, also known as organic electric laser display or organic light-emitting semiconductor (Organic Electroluminescence Display, OLED). OLED is a current-type organic light-emitting device that emits light through the injection and recombination of carriers, and the luminous intensity is proportional to the injected current. Under the action of the electric field, the holes generated by the anode and the electrons generated by the cathode will move, and are injected into the hole transport layer and the electron transport layer respectively, and migrate to the light-emitting layer. When the two meet in the light-emitting layer, energy excitons are generated, which excite the light-emitting molecules and ultimately produce visible light.

[0035] In the present invention, main body material, matrix material, host material and matrix material have the same meaning and can be interchanged.

[0036] In the present invention, metal organic complex, metal organic complex and organometallic complex have the same meaning and can be used interchangeably.

[0037] In the present invention, printing ink, ink and ink have the same meaning and can be interchanged.

[0038] In the present invention, "substituted" means that a hydrogen atom in a compound is replaced by a substituent.

[0039] In the present invention, "substituted or unsubstituted" means that the defined group may be substituted or unsubstituted. When the defined group is substituted, it should be understood that the defined group may be substituted by one or more substituents R, wherein R is selected from but not limited to: deuterium atom, cyano group, isocyano group, nitro group or halogen, alkyl group containing 1 to 20 C atoms, heterocyclic group containing 3 to 20 ring atoms, aromatic group containing 6 to 20 ring atoms, heteroaromatic group containing 5 to 20 ring atoms, -NR'R", silane group, carbonyl group, alkoxycarbonyl group, aryloxycarbonyl group, carbamoyl group, haloformyl group, formyl group, isocyanate group, thiocyanate group, isothiocyanate group, hydroxyl group, trifluoromethyl group, and the above groups may be further substituted by substituents acceptable in the art; it is understood that R' and R" in -NR'R" are independently selected from but not limited to: H, deuterium atom, thiocyanate group, isothiocyanate group, hydroxyl group, trifluoromethyl group, and the above groups may be further substituted by substituents acceptable in the art; it is understood that R' and R" in -NR'R" are independently selected from but not limited to: H, deuterium atom, thiocyanate group, isothiocyanate group, hydroxyl group, trifluoromethyl group, Preferably, R is selected from, but not limited to, a deuterium atom, a cyano group, an isocyano group, a nitro group or a halogen group, an alkyl group containing 1 to 10 carbon atoms, a heterocyclic group containing 3 to 20 ring atoms, an aromatic group containing 6 to 20 ring atoms, or a heteroaromatic group containing 5 to 20 ring atoms, a deuterium atom, a cyano group, an isocyano group, a nitro group or a halogen group, an alkyl group containing 1 to 10 carbon atoms, a heterocyclic group containing 3 to 10 ring atoms, an aromatic group containing 6 to 20 ring atoms, or a heteroaromatic group containing 5 to 20 ring atoms, a silane group, a carbonyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, a carbamoyl group, a haloformyl group, a formyl group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, and a trifluoromethyl group, and the above groups may be further substituted with substituents acceptable in the art.

[0040] In the present invention, the "number of ring atoms" refers to the number of atoms in the atoms that constitute the ring itself of a structural compound (e.g., a monocyclic compound, a condensed ring compound, a cross-linked compound, a carbocyclic compound, or a heterocyclic compound) formed by atoms bonded together to form a ring. When the ring is substituted with a substituent, the atoms contained in the substituent are not included in the ring atoms. The "number of ring atoms" described below also applies unless otherwise specified. For example, the number of ring atoms of a benzene ring is 6, the number of ring atoms of a naphthalene ring is 10, and the number of ring atoms of a thienyl group is 5.

[0041] An aromatic group refers to a hydrocarbon group containing at least one aromatic ring. A heteroaromatic group refers to an aromatic hydrocarbon group containing at least one heteroatom. The heteroatom is preferably selected from Si, N, P, O, S and / or Ge, and is particularly preferably selected from Si, N, P, O and / or S. A fused ring aromatic group refers to an aromatic group having two or more rings, wherein two carbon atoms are shared by two adjacent rings, i.e., a fused ring. A fused heterocyclic aromatic group refers to a fused heterocyclic aromatic hydrocarbon group containing at least one heteroatom. For the purposes of the present invention, aromatic or heteroaromatic groups include not only aromatic ring systems but also non-aromatic ring systems. Thus, groups such as pyridine, thiophene, pyrrole, pyrazole, triazole, imidazole, oxazole, oxadiazole, thiazole, tetrazole, pyrazine, pyridazine, pyrimidine, triazine, and carbene are also considered aromatic or heterocyclic aromatic groups for the purposes of this invention. For the purposes of the present invention, fused aromatic or fused heteroaromatic ring systems include not only systems containing aromatic or heteroaromatic groups, but also systems in which multiple aromatic or heteroaromatic groups are interrupted by short non-aromatic units (<10% non-H atoms, preferably less than 5% non-H atoms, such as C, N or O atoms). Thus, groups such as 9,9'-spirobifluorene, 9,9-diarylfluorene, triarylamines, diaryl ethers, etc. are also considered aromatic ring systems for the purposes of this invention.

[0042] The present invention provides a mixture comprising an organic compound H and a luminophore E, wherein 1) the organic compound H is an aggregation-induced emission material, and its emission spectrum is on the short-wavelength side of the absorption spectrum of the luminophore E and at least partially overlaps with each other; 2) the Full Width (FWHM) of the emission spectrum of the luminophore E is less than or equal to 55 nm.

[0043] In certain preferred embodiments, when the organic compound H is in an aggregated state, the wavelength of the peak of its light emission spectrum is less than or equal to the wavelength of the peak of the absorption spectrum of the luminophore E.

[0044] In some preferred embodiments, the luminophore E is as disclosed in the patent application with international publication number WO2022213993A1, the entire content of which is hereby incorporated herein by reference.

[0045] In another preferred embodiment, the luminescent body E is not an aggregation-induced emission material.

[0046] In certain preferred embodiments, the luminescence spectrum of the luminophore E is similar in solution and in aggregated state; so-called similarity means that the difference in the peak of the luminescence spectrum is no more than 5 nm, preferably no more than 4 nm, more preferably no more than 3 nm, particularly preferably no more than 2 nm, and most preferably no more than 1 nm.

[0047] In some preferred embodiments, the FWHM of the light emission spectrum of the luminophore E is ≤50 nm, preferably ≤40 nm, more preferably ≤35 nm, and most preferably ≤30 nm.

[0048] In other preferred embodiments, the luminescent body E has a fluorescence quantum efficiency (PLQY) of ≥50%, preferably ≥60%, more preferably ≥70%, and most preferably ≥80%.

[0049] In some particularly preferred embodiments, the luminophore E comprises a structural unit represented by chemical formula (1), (2), (3), or (4):

[0050] Where: Ar 1 -Ar 3 The same or different aromatic or heteroaromatic groups are selected from 5 to 24 ring atoms; Ar 4 -Ar 5 The same or different aromatic or heteroaromatic groups are selected from empty or aromatic groups having 5 to 24 ring atoms; when Ar 4 -Ar 5 When not empty, X a and X b Independently selected from N, CR at each occurrence 6 、SiR 6 , Y a and Y b In each occurrence, independently selected from B, P=O, CR 6 、SiR 6 ; when Ar 4 or Ar 5 When it is empty, X b Selected from N, CR 6 、SiR 6 , Y a Selected from B, P=O, CR 6 、SiR 6 , X a and Y b Independently selected from NR at each occurrence 6 , CR 6 R 7 、SiR 6 R 7 、C=O、O、C=N(R 6 ), C=C(R 6 R 7 ), PR 6 、P(=O)R 6 , S, S=O or SO2; X 1 、X 2 are independently selected from empty or a bridging group;

[0051] R 1 -R 7 and D, which may be identical or different on each occurrence, or a linear alkyl, haloalkyl, alkoxy or thioalkoxy radical having 1 to 20 C atoms, or a branched or cyclic alkyl, haloalkyl, alkoxy, thioalkoxy or silyl radical having 3 to 20 C atoms, or a keto radical having 1 to 20 C atoms, or an alkoxycarbonyl radical having 2 to 20 C atoms, or an aryloxycarbonyl radical having 4 to 20 C atoms, or a cyano, carbamoyl, haloformyl, formyl, isocyano, Isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, CF3, Cl, Br, F, I, a crosslinkable group, or a substituted or unsubstituted aromatic or heteroaromatic ring system having 5 to 40 ring atoms, or an aryloxy or heteroaryloxy group having 5 to 40 ring atoms, or an arylamine or heteroarylamine group having 5 to 40 ring atoms, a disubstituted unit at any position of the above groups or a combination of these groups, wherein one or more groups can form a monocyclic or polycyclic aliphatic or aromatic ring system with each other and / or the ring to which the groups are bonded.

[0052] In some preferred embodiments, R 1 -R 7 and D, which may be identical or different on each occurrence, or a linear alkyl, haloalkyl, alkoxy or thioalkoxy radical having 1 to 10 C atoms, or a branched or cyclic alkyl, haloalkyl, alkoxy, thioalkoxy or silyl radical having 3 to 10 C atoms, or a keto radical having 1 to 10 C atoms, or an alkoxycarbonyl radical having 2 to 10 C atoms, or an aryloxycarbonyl radical having 6 to 10 C atoms, or a cyano, carbamoyl, haloformyl, formyl, isocyano, Isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, CF3, Cl, Br, F, I, a crosslinkable group, or a substituted or unsubstituted aromatic or heteroaromatic ring system having 5 to 20 ring atoms, or an aryloxy or heteroaryloxy group having 5 to 20 ring atoms, or an arylamine or heteroarylamine group having 5 to 20 ring atoms, a disubstituted unit at any position of the above groups or a combination of these groups, wherein one or more groups can form a monocyclic or polycyclic aliphatic or aromatic ring system with each other and / or the ring to which the groups are bonded.

[0053] In some preferred embodiments, the luminophore E comprises a structural unit represented by the following chemical formula (1a) or (2a) or (3a) or (4a):

[0054] Among them, Ar 1 -Ar 5 、X1 、X 2 、R 1 -R 5 The definition of is the same as above.

[0055] In some preferred embodiments, X 1 and X 2 are independently selected from O or S; in some more preferred embodiments, X 1 and X 2 All are O.

[0056] In some preferred embodiments, X 1 、X 2 At least one is empty; particularly preferably, both are empty, and the luminophore E comprises a structural unit represented by the following chemical formula (1b) or (2b) or (3b) or (4b):

[0057] Among them, Ar 1 -Ar 5 、R 1 -R 5 The definition of is the same as above.

[0058] In some preferred embodiments, X 1 、X 2 At least one is a single bond; particularly preferably, both are single bonds, and the luminophore E comprises a structural unit represented by the following chemical formula (1c) or (2c) or (3c) or (4c):

[0059] Among them, Ar 1 -Ar 5 、R 1 -R 5 The definition of is the same as above.

[0060] In certain preferred embodiments, X 1 、X 2 In each occurrence, the same or different two-bridge groups are present. Preferred two-bridge groups are:

[0061] Wherein: R1, R2, R3 and R4 are defined as above 1 ; Dashed bonds represent bonds to adjacent structural units.

[0062] For the purposes of the present invention, aromatic ring systems contain 6 to 20 carbon atoms in the ring system, and heteroaromatic ring systems contain 1 to 20 carbon atoms and at least one heteroatom in the ring system, provided that the total number of carbon atoms and heteroatoms is at least 5. The heteroatoms are preferably selected from Si, N, P, O, S and / or Ge, particularly preferably from Si, N, P, O and / or S. For the purposes of the present invention, aromatic or heteroaromatic ring systems include not only systems of aromatic or heteroaromatic groups, but also systems in which multiple aromatic or heteroaromatic groups are interrupted by short non-aromatic units (<10% non-H atoms, preferably less than 5% non-H atoms, such as C, N or O atoms). Thus, groups such as 9,9′-spirobifluorene, 9,9-diarylfluorene, triarylamines, diaryl ethers, etc. are also considered aromatic ring systems for the purposes of this invention.

[0063] For the purpose of the present invention, any H atom of the organic compound H or the luminophore E may be replaced by R 10 Group substitution, R 10 The definition of R is the same as above 1 , preferably, (1) C1-C10 alkyl, particularly preferably refers to the following groups: methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclobutyl, 2-methylbutyl, n-pentyl, n-hexyl, cyclohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-methylheptyl, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, vinyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl , heptenyl, cycloheptenyl, octenyl, cyclooctenyl, ethynyl, propynyl, butynyl, pentynyl, hexynyl and octynyl; (2) C1-C10 alkoxy, particularly preferably methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy or 2-methylbutoxy; (3) C2-C10 aryl or heteroaryl, which may be monovalent or divalent depending on the application and may in each case also be replaced by the above-mentioned radicals R 10Substituted and bonded to the aromatic or heteroaromatic ring via any desired position, particularly preferably the following radicals are meant: benzene, naphthalene, anthracene, pyrene, dihydropyrene, chrysene, fluoranthene, butacene, pentacene, benzopyrene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole, indole, isoindole, carbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo-5,6-quinoline, benzo-6,7-quinoline, benzo-7,8-quinoline, phenothiazine, phenoxazine, pyrazole, indazole, imidazole, benzimidazole, naphthimidazole, phenanthromidiazole, pyridimidazole, pyrazinoimidazole, quinoxalinoimidazole, oxazole, benzoxazole, naphthioxazole, anthraquinoxazole, phenanthromidiazole, isoxazole, 1,2- Thiazole, 1,3-thiazole, benzothiazole, pyridazine, benzopyridazine, pyrimidine, benzopyrimidine, quinoxaline, pyrazine, diazaanthracene, 1,5-naphthyridine, nitrogen carbazole, benzocarboline, phenanthroline, 1,2,3-triazole, 1,2,4-triazole, benzotriazole, 1,2,3-oxadiazole, 1,2,4-oxadiazole, 1,2,5-oxadiazole, 1,3,4- The present invention also includes oxadiazole, 1,2,3-thiadiazole, 1,2,4-thiadiazole, 1,2,5-thiadiazole, 1,3,4-thiadiazole, 1,3,5-triazine, 1,2,4-triazine, 1,2,3-triazine, tetrazole, 1,2,4,5-tetrazine, 1,2,3,4-tetrazine, 1,2,3,5-tetrazine, purine, pteridine, indolizine and benzothiadiazole. For the purposes of the present invention, aromatic and heteroaromatic ring systems are taken to mean, in addition to the aryl and heteroaryl radicals mentioned above, biphenylene, terphenylene, fluorene, spirobifluorene, dihydrophenanthrene, tetrahydropyrene and cis- or trans-indenofluorene.

[0064] In certain preferred embodiments, in the luminophore E, Ar 1 -Ar 5 The same or different groups are selected from aromatic and heteroaromatic groups having 5 to 20 ring atoms at each occurrence; preferably selected from aromatic and heteroaromatic groups having 5 to 18 ring atoms; more preferably selected from aromatic and heteroaromatic groups having 5 to 15 ring atoms; most preferably selected from aromatic and heteroaromatic groups having 5 to 10 ring atoms; they may be unsubstituted or substituted with one or two R 10 Preferred aryl or heteroaryl groups include benzene, naphthalene, anthracene, phenanthrene, pyridine, benzofuran, pyrene or thiophene.

[0065] In some preferred embodiments, Ar 1 -Ar 5 At each occurrence, independently selected from the following structural formula:

[0066] Where: X0 is CR 11 or N; Y0 is selected from NR 11 , CR 12 R13 、SiR 14 R 15 , C(=O), S or O; R 11 、R 12 、R 13 、R 14 、R 15 The definition of R is the same as above 1 .

[0067] Further, Ar 1 -Ar 5 Each occurrence is independently selected from one or a combination of the following chemical formulae, and may be further substituted with any other:

[0068] In a particularly preferred embodiment, Ar 1 -Ar 5 It is phenyl.

[0069] In some preferred embodiments, Ar 4 、Ar 5 At least one is empty; particularly preferably, both are empty, and the luminophore E comprises a structural unit represented by the following chemical formula (1d) or (2d) or (1e) or (2e) or (3d) or (4d1) or (4d2):

[0070] Among them, Ar 1 -Ar 3 、Ar 4 -Ar 5 、X 1 、X 2 、X a 、Y a 、Y b 、R 1 -R 5 The definition of is as above.

[0071] Preferably, X in formula (1d) and (1e) a The same or different are independently selected from NR 6 , CR 6 R 7 、SiR 6 R 7 , O or S.

[0072] Preferably, Y in formula (2d) and (2e) b The same or different are independently selected from C=O, O, S, P(=O)R 6 , S═O or SO2; particularly preferably selected from C═O.

[0073] Preferably, X in chemical formulas (3d), (4d1) and (4d2) a The same or different are independently selected from NR 6 , CR 6 R 7 、SiR 6 R 7 , O or S.

[0074] In some other preferred embodiments, the luminophore E comprises the structural units represented by the following chemical formulas (1f) to (1i):

[0075] where Y c which may be the same or different and are selected from O or S; Ar 1 -Ar 3 、X a 、R 3 -R 5 The definition of is the same as above.

[0076] In a particularly preferred embodiment, the above-mentioned Ar 2 、Ar 3 It is preferably selected from the following structural units and can be further substituted arbitrarily:

[0077] In certain preferred embodiments, in the structural units according to chemical formulas (1)-(1i), (2)-(2e), (3)-(3d), and (4)-(4d2), wherein R 1 -R 5 When it occurs multiple times, it may contain the following structural units or their combinations, which may be the same or different:

[0078] Where n0 is 1 or 2 or 3 or 4.

[0079] In a preferred embodiment, the luminous body E has the following structure:

[0080] Where: Y c The definition of R is as above; 21 -R 25R is H, D, or a linear alkyl, alkoxy or thioalkoxy group having 1 to 20 carbon atoms, or a branched or cyclic alkyl, alkoxy, thioalkoxy or silyl group having 3 to 20 carbon atoms, or a keto group having 1 to 20 carbon atoms, or an alkoxycarbonyl group having 2 to 20 carbon atoms, or an aryloxycarbonyl group having 4 to 20 carbon atoms, or a cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, CF3, Cl, Br, F, a crosslinkable group, or a substituted or unsubstituted aromatic or heteroaromatic ring system having 5 to 40 ring atoms, or an aryloxy or heteroaryloxy group having 5 to 40 ring atoms, or a combination of these groups, wherein one or more of the groups can form a monocyclic or polycyclic aliphatic or aromatic ring system with each other and / or the ring to which they are bonded; and R 21 -R 25 At least one of them contains an alcohol-soluble or water-soluble group; w and v are independently selected from any integer from 0 to 4; o and q are independently selected from any integer from 0 to 5; and p is independently selected from any integer from 0 to 3.

[0081] Preferably, R 21 -R 25 It can be H, D, or a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 10 C atoms, or a branched or cyclic alkyl, alkoxy, thioalkoxy or silyl group having 3 to 10 C atoms, or a keto group having 1 to 10 C atoms, or an alkoxycarbonyl group having 2 to 10 C atoms, or an aryloxycarbonyl group having 6 to 10 C atoms, or a cyano group, a carbamoyl group, a haloformyl group, a formyl group, an isocyanate group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, CF3, Cl, Br, F, a crosslinkable group, or a substituted or unsubstituted aromatic or heteroaromatic ring system having 5 to 20 ring atoms, or an aryloxy or heteroaryloxy group having 5 to 20 ring atoms, or a combination of these groups, where one or more of the groups can form a monocyclic or polycyclic aliphatic or aromatic ring system with each other and / or the ring to which the groups are bonded.

[0082] In the embodiment of the present invention, the triplet energy level (T1), the singlet energy level (S1), the HOMO, the LUMO, and the resonance factor strength f play a key role in the energy level structure of the organic material. The determination of these parameters is introduced below.

[0083] HOMO and LUMO energy levels can be measured by photoelectric effects, such as XPS (X-ray photoelectron spectroscopy) and UPS (ultraviolet photoelectron spectroscopy), or by cyclic voltammetry (CV). Recently, quantum chemical methods, such as density functional theory (DFT), have also become effective methods for calculating molecular orbital energy levels.

[0084] The triplet energy level T1 of an organic material can be measured by low-temperature time-resolved luminescence spectroscopy or obtained by quantum simulation calculations (e.g., by time-dependent DFT), such as using the commercial software Gaussian 09W (Gaussian Inc.). The specific simulation method is described below. The singlet energy level S1 of an organic material can be determined by absorption or emission spectroscopy, or obtained by quantum simulation calculations (e.g., time-dependent DFT). The resonance factor intensity f can also be obtained by quantum simulation calculations (e.g., time-dependent DFT).

[0085] It should be noted that the absolute values ​​of HOMO, LUMO, T1, and S1 depend on the measurement or calculation method used. Even for the same method, different evaluation methods, such as the starting point and peak point on the CV curve, can give different HOMO / LUMO values. Therefore, reasonable and meaningful comparisons should be made using the same measurement and evaluation methods. In the description of the embodiments of the present invention, the values ​​of HOMO, LUMO, T1, and S1 are based on time-dependent DFT simulations, but this does not affect the application of other measurement or calculation methods.

[0086] In certain preferred embodiments, the luminophore E according to the present invention has (S1-T1) ≤ 0.30 eV, preferably ≤ 0.25 eV, more preferably ≤ 0.20 eV, even more preferably ≤ 0.15 eV, and most preferably ≤ 0.10 eV.

[0087] In certain embodiments, in the mixture, the luminophore E is a small molecule or a polymer.

[0088] In some embodiments, the luminophore E has good solubility in the resin or resin prepolymer.

[0089] In certain preferred embodiments, the organic compound H has good solubility in the resin or resin prepolymer.

[0090] In a preferred embodiment, the organic compound H and / or the luminophore E contain at least one alcohol-soluble or water-soluble group, as disclosed in the patent application with international publication number WO2022078434A1, the entire contents of which are hereby incorporated herein by reference.

[0091] In some preferred embodiments, the organic compound H and / or the luminophore E contain at least two alcohol-soluble or water-soluble groups.

[0092] In other preferred embodiments, the organic compound H and / or the luminophore E contain at least three alcohol-soluble or water-soluble groups.

[0093] In a preferred embodiment, the alcohol-soluble or water-soluble groups of the organic compound H and / or the luminophore E are selected from alcohols, aldehydes, acids, crown ethers, polyethers, primary amines and the like.

[0094] Preferably, the alcohol-soluble or water-soluble group is selected from the following structure:

[0095] Where: R 31 -R 37 It can be a straight-chain alkyl, alkoxy or thioalkoxy group with 1 to 20 C atoms, or a branched or cyclic alkyl, alkoxy, thioalkoxy or silyl group with 3 to 20 C atoms, or a substituted keto group with 1 to 20 C atoms, or an alkoxycarbonyl group with 2 to 20 C atoms, or an aryloxycarbonyl group with 4 to 20 C atoms, or a cyano group, carbamoyl, haloformyl, formyl, isocyano group, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, CF3, Cl, Br, F, a crosslinkable group, or a substituted or unsubstituted aromatic or heteroaromatic ring system with 5 to 40 ring atoms, or an aryloxy or heteroaryloxy group with 5 to 40 ring atoms, or a combination of these groups, wherein one or more of the groups can form a monocyclic or polycyclic aliphatic or aromatic ring system with each other and / or the ring to which the group is bonded; t is an integer greater than 0.

[0096] Furthermore, in the present invention, individual H atoms or CH2 groups may be substituted by the above-mentioned groups or groups R0. R0 is selected from alkyl groups having 1 to 40 C atoms, preferably from the following groups: methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclobutyl, methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, n-hexyl, cyclohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, ethylhexyl, trifluoromethyl, pentafluoroethyl, trifluoroethyl, vinyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl, ethynyl, propynyl, butynyl, pentynyl, hexynyl or octynyl; alkoxy groups having 1 to 40 C atoms, such as methoxy, trifluoromethoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy or methylbutoxy.

[0097] Examples of luminophore E are given below, but are not limited thereto, and may be further substituted arbitrarily:

[0098] In other embodiments, the organic compound H and / or the luminophore E contain at least one cross-linkable group, as disclosed in the patent application with international publication number WO2022078431A1, the entire contents of which are hereby incorporated herein by reference; the advantage of this is that when the resin prepolymer undergoes copolymerization or homopolymerization, the luminophore E may at least partially participate in the polymerization.

[0099] In some preferred embodiments, the organic compound H and / or the luminophore E contain at least two cross-linkable groups.

[0100] In some other preferred embodiments, the organic compound H and / or the luminophore E contain at least three cross-linkable groups.

[0101] In certain preferred embodiments, the organic compound H can be polymerized to form a polymer. That is, the mixture according to the present invention comprises the organic compound H and the luminophore E, or comprises the polymer and the luminophore E, or comprises the organic compound H, the polymer, and the luminophore E. Preferably, the polymer is a side chain polymer.

[0102] In certain embodiments, the luminophore E is a polymer comprising at least one repeating structural unit represented by chemical formula (1), (2), (3), or (4). Preferably, the polymer is a side chain polymer, as disclosed in patent application International Publication No. WO2022078456A1, the entire contents of which are hereby incorporated herein by reference.

[0103] In certain preferred embodiments, for the purpose of the present invention, the luminophore E may be further selected from compounds (derivatives of fluoroborane (Bodipy)) having the following structural formula:

[0104] Where: X is CR 19 or N; R 11 -R 19are each independently selected from H, alkyl, cycloalkyl, heterocyclyl, alkenyl, cycloalkenyl, alkynyl, hydroxyl, thiol, alkoxy, alkylthio, arylether, arylthioether, aryl, heteroaryl, halogen, cyano, aldehyde, carbonyl, carboxyl, oxycarboxyl, carbamoyl, amino, nitro, silyl, siloxane, borane or phosphine oxide, and R 11 -R 19 It can form a condensed ring or an aliphatic ring with adjacent substituents.

[0105] Examples of suitable Bodipy derivatives include, but are not limited to:

[0106] According to the present invention, organic compound H is an aggregation-induced emission material. Aggregation-induced emission (AIE) is a unique photophysical phenomenon in which molecules that are non-luminescent or weakly luminescent in solution exhibit significantly enhanced luminescence when aggregated or in the solid state. This phenomenon contrasts sharply with the weakening or quenching of luminescence by traditional fluorescent molecules when aggregated. Suitable AIE materials can be used in the present invention, as long as their luminescence spectrum matches the absorption spectrum of the luminophore E.

[0107] In certain preferred embodiments, the organic compound H comprises at least one structure selected from the group consisting of chemical formulas (I-1) to (I-5):

[0108] wherein: R1-R4, R8 are substituents which, on each occurrence, may be identical or different and are selected from a linear alkyl, alkenyl, haloalkyl, alkoxy or thioalkoxy group having 1 to 20 carbon atoms, or a branched or cyclic alkyl, haloalkyl, alkoxy, thioalkoxy or silyl group having 3 to 20 carbon atoms, or a keto group having 1 to 20 carbon atoms, or an alkoxycarbonyl group having 2 to 20 carbon atoms, or an aryloxycarbonyl group having 4 to 20 carbon atoms, or Cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, CF3, Cl, Br, F, I, a crosslinkable group, or a substituted or unsubstituted aromatic or heteroaromatic ring system having 5 to 40 ring atoms, or an aryloxy or heteroaryloxy group having 5 to 40 ring atoms, or an arylamine or heteroarylamine group having 5 to 40 ring atoms, a disubstituted unit at any position of the above groups or a combination of these groups, which may be further substituted.

[0109] R5-R7, at each occurrence, may be identical or different and be selected from H, D, or a linear alkyl, alkenyl, haloalkyl, alkoxy or thioalkoxy group having 1 to 20 carbon atoms, or a branched or cyclic alkyl, haloalkyl, alkoxy, thioalkoxy or silyl group having 3 to 20 carbon atoms, or a keto group having 1 to 20 carbon atoms, or an alkoxycarbonyl group having 2 to 20 carbon atoms, or an aryloxycarbonyl group having 4 to 20 carbon atoms, or a cyano group. , carbamoyl, haloformyl, formyl, isocyanate, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, CF3, Cl, Br, F, I, a cross-linkable group, or a substituted or unsubstituted aromatic or heteroaromatic ring system having 5 to 40 ring atoms, or an aryloxy or heteroaryloxy group having 5 to 40 ring atoms, or an arylamine or heteroarylamine group having 5 to 40 ring atoms, a disubstituted unit at any position of the above groups or a combination of these groups, which may be further substituted.

[0110] n is selected from integers of 0-5, and m is selected from integers of 0-4.

[0111] In certain embodiments, R5-R7 are selected from H or D.

[0112] In some preferred embodiments, R1-R7 and R8, when they appear each time, may be the same or different and selected from a linear alkyl, alkenyl, haloalkyl, alkoxy or thioalkoxy group having 1 to 10 carbon atoms, or a branched or cyclic alkyl, haloalkyl, alkoxy, thioalkoxy or silyl group having 3 to 10 carbon atoms, or a keto group having 1 to 10 carbon atoms, or an alkoxycarbonyl group having 2 to 10 carbon atoms, or an aryloxy group having 4 to 10 carbon atoms. The invention also includes but is not limited to: a hydroxyl group, a nitro group, a hydroxyl group, a hydroxyl group, a hydroxyl group, a hydroxyl group, a hydroxyl group, a hydroxyl group, a hydroxyl group, a hydroxyl group, a hydroxyl group, a hydroxyl group, a hydroxyl group, a hydroxyl group, a hydroxyl group, a hydroxyl group, a hydroxyl group, a hydroxyl group, a hydroxyl group, a hydroxyl group, a hydroxyl group, a hydroxyl group, a hydroxyl group, a hydroxyl group, a hydroxyl group, a hydroxyl group, a hydroxyl group, a hydroxyl group, a hydroxyl group, a hydroxyl group, a hydroxyl group, a hydroxyl group, a hydroxyl group, a hydroxyl group, a hydroxyl group, a hydroxyl group, a hydroxyl group, a hydroxyl group, a hydroxyl group, a hydroxyl group, a hydroxyl group

[0113] In some preferred embodiments, in the organic compound H, R1-R7 and R8 contain at least one electron-withdrawing group.

[0114] In some preferred embodiments, the organic compound H contains two electron-withdrawing groups.

[0115] In certain preferred embodiments, suitable electron withdrawing groups include, but are not limited to, F, Cl, cyano, a partially or fully fluorinated alkyl chain, or one of the following groups, which may be further substituted:

[0116] Where: n1 is 1, 2 or 3; X1-X 10 Selected from CR 43 Or N, and at least one is N, but two adjacent Xs cannot be N at the same time; M 1 、M 2 、M 3 Each independently represents NR 43 , CR 43 R 44 、SiR 43 R 44 、O、C=N(R 43 ), C=CR 43 R 44 PR 43 、P(=O)R 43 , S, S=O, SO2 or none; R 41 、R 42 、R 43 、R 44 The meaning is the same as above R5.

[0117] In some preferred embodiments, R1-R7 and R8 in chemical formulas (I-1)-(I-5) are selected from the following groups, which may be further substituted:

[0118] In some preferred embodiments, the organic compound H is selected from the following structures:

[0119] wherein R2, R3, R4, R8, m, and n are substituents on the benzene ring, and their definitions are as above.

[0120] According to the mixture of the present invention, the organic compound H has a high extinction coefficient. The extinction coefficient is also called the molar extinction coefficient, which refers to the absorption coefficient when the concentration is 1 mol / L, represented by the symbol ε, and the unit is Lmol -1 cm -1 , the preferred extinction coefficient: ε≥1*10 3 ; More preferred: ε≥1*10 4 More preferably, ε≥2*10 4 More preferably: ε≥3*10 4 ; Particularly preferred: ε≥5*10 4; Most preferred: ε≥1*10 5 Preferably, the extinction coefficient refers to the extinction coefficient at the wavelength corresponding to the absorption peak.

[0121] In certain embodiments, the absorption spectrum of the organic compound H in an aggregated state is between 380 nm and 520 nm.

[0122] In some preferred embodiments, the luminescence spectrum of the organic compound H in an aggregated state is between 460 nm and 520 nm.

[0123] In other preferred embodiments, the luminescence spectrum of the organic compound H in the aggregated state is between 500 nm and 520 nm.

[0124] In another preferred embodiment, the organic compound H has a fluorescence quantum efficiency (PLQY) of ≥50% when in an aggregated state, preferably ≥60%, more preferably ≥70%, particularly preferably ≥80%, and most preferably ≥90%.

[0125] In a preferred embodiment, the organic compound H has a high solubility in the organic solvent. Preferably, the solubility of the organic compound H in toluene is generally ≥10 mg / mL, preferably ≥20 mg / mL, more preferably ≥40 mg / mL, even more preferably ≥70 mg / mL, particularly preferably ≥100 mg / mL, and most preferably ≥150 mg / mL.

[0126] Some examples of suitable organic compounds H are listed below (but are not limited to), which may be further optionally substituted:

[0127] According to the mixture of the present invention, the absorption spectrum of the luminophore E and the emission spectrum of the organic compound H have a large overlap, and a relatively efficient energy transfer can be achieved between them ( resonance energy transfer (FRET)).

[0128] In certain preferred embodiments, the luminescence spectrum of the mixture is completely derived from the luminophore E, that is, complete energy transfer is achieved between the luminophore E and the organic compound H.

[0129] In certain embodiments, the mixture comprises two or more organic compounds H.

[0130] In certain embodiments, the organic compound H is selected from one of the chemical formulas (1)-(1e) or (2)-(2e).

[0131] In a preferred embodiment, in the mixture, the weight ratio of the organic compound H to the luminophore E is from 50:50 to 99:1, preferably from 60:40 to 98:2, more preferably from 70:30 to 97:3, and most preferably from 80:20 to 95:5.

[0132] In a more preferred embodiment, at least one of the organic compound H and the luminophore E in the mixture according to the present invention is partially H-deuterated, preferably ≥10% H-deuterated, more preferably ≥20% H-deuterated, very preferably ≥30% H-deuterated, and most preferably ≥40% H-deuterated.

[0133] The invention also relates to a composition comprising a mixture according to the invention and an organic resin and / or a solvent.

[0134] Organic resins suitable for the present invention include, but are not limited to, polystyrene, polyacrylate, polymethacrylate, polycarbonate, polyurethane, polyvinyl pyrrolidone, polyvinyl acetate, polybutylene, polyethylene glycol, polysiloxane, epoxy resin, polyvinyl alcohol, polyacrylonitrile, polyvinylidene chloride (PVDC), polystyrene-acrylonitrile (SAN), polybutylene terephthalate (PBT), polyethylene terephthalate (PET), polyvinyl butyrate (PVB), polyvinyl chloride (PVC), polyamide, polyoxymethylene, polyimide, polyetherimide, or mixtures thereof.

[0135] Furthermore, organic resins suitable for the present invention include but are not limited to those formed by homopolymerization or copolymerization of the following monomers (resin prepolymers): styrene derivatives, acrylate derivatives, acrylonitrile derivatives, acrylamide derivatives, vinyl ester derivatives, vinyl ether derivatives, maleimide derivatives, and conjugated diene derivatives.

[0136] Examples of styrene derivatives include alkylstyrenes such as α-methylstyrene, o-, m- and p-methylstyrene, p-butylstyrene, especially p-tert-butylstyrene, and alkoxystyrenes such as p-methoxystyrene, p-butoxystyrene and p-tert-butoxystyrene.

[0137] Examples of acrylate derivatives include methyl acrylate, methyl methacrylate, ethyl acrylate, ethyl methacrylate, n-propyl acrylate, n-propyl methacrylate, isopropyl acrylate, isopropyl methacrylate, n-butyl acrylate, n-butyl methacrylate, isobutyl acrylate, isobutyl methacrylate, sec-butyl acrylate, sec-butyl methacrylate, tert-butyl acrylate, tert-butyl methacrylate, 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl acrylate, 2-hydroxypropyl methacrylate, 3-hydroxypropyl acrylate, 3-hydroxypropyl methacrylate, 2-hydroxyethyl acrylate, 2-hydroxypropyl methacrylate, 2-hydroxypropyl acrylate, 2-hydroxypropyl methacrylate, 2-hydroxypropyl acrylate, 2-hydroxypropyl methacrylate, 2-hydroxyethyl acrylate, 2-hydroxypropyl methacrylate, 2-hydroxypropyl acrylate, 2-hydroxypropyl methacrylate, 2-hydroxypropyl acrylate, 2-hydroxypropyl methacrylate, 2-hydroxyethyl acrylate, 2-hydroxypropyl methacrylate, 2-hydroxypropyl acrylate, 2-hydroxypropyl methacrylate, 2-hydroxypropyl acrylate, 2-hydroxypropyl methacrylate, 2-hydroxyethyl acrylate, 2-hydroxypropyl methacrylate, 2-hydroxypropyl acrylate, 2-hydroxypropyl methacrylate, 2-hydroxypropyl methacrylate, 2-hydroxypropyl acrylate, 2-hydroxypropyl methacrylate, 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate, 2-hydroxypropyl meth ...ethyl acrylate, 2-hydroxypropyl acrylate 2-Hydroxybutyl methacrylate, 2-Hydroxybutyl methacrylate, 3-Hydroxybutyl acrylate, 3-Hydroxybutyl methacrylate, 4-Hydroxybutyl acrylate, 4-Hydroxybutyl methacrylate, Allyl acrylate, Allyl methacrylate, Benzyl acrylate, Benzyl methacrylate, Cyclohexyl acrylate, Cyclohexyl methacrylate, Phenyl acrylate, Phenyl methacrylate, 2-Methoxyethyl acrylate, 2-Methoxyethyl methacrylate, 2-Phenoxyethyl acrylate, 2-Phenoxyethyl methacrylate, Methoxydiglycol acrylate, Methoxydiglycol methacrylate, Methoxytriglycol acrylate, Methoxy Oxytriethylene glycol methacrylate, methoxypropylene glycol acrylate, methoxypropylene glycol methacrylate, methoxydipropylene glycol acrylate, methoxydipropylene glycol methacrylate, isobornyl acrylate, isobornyl methacrylate, dicyclopentadienyl acrylate, dicyclopentadienyl methacrylate, adamantyl (meth)acrylate, norbornyl (meth)acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-hydroxy-3-phenoxypropyl methacrylate, glyceryl monoacrylate and glyceryl monomethacrylate; 2-aminoethyl acrylate, 2-aminoethyl methacrylate, 2-dimethylaminoethyl acrylate Methylaminoethyl acrylate, 2-dimethylaminoethyl methacrylate, N,N-dimethylaminoethyl (meth)acrylate, N,N-diethylaminoethyl (meth)acrylate, 2-aminopropyl acrylate, 2-aminopropyl methacrylate, 2-dimethylaminopropyl acrylate, 2-dimethylaminopropyl methacrylate, 3-aminopropyl acrylate, 3-aminopropyl methacrylate, N,N-dimethyl-1,3-propylenediamine benzyl (meth)acrylate, 3-dimethylaminopropyl acrylate, 3-dimethylaminopropyl methacrylate, glycidyl acrylate and glycidyl methacrylate.

[0138] Examples of the acrylonitrile derivatives are acrylonitrile, methacrylonitrile, α-chloroacrylonitrile and vinylidene cyanide.

[0139] Examples of the acrylamide derivatives are acrylamide, methacrylamide, α-chloroacrylamide, N-2-hydroxyethylacrylamide and N-2-hydroxyethylmethacrylamide.

[0140] Examples of vinyl ester derivatives are vinyl acetate, vinyl propionate, vinyl butyrate and vinyl benzoate.

[0141] Examples of the vinyl ether derivatives are vinyl methyl ether, vinyl ethyl ether and allyl glycidyl ether.

[0142] Examples of maleimide derivatives include maleimide, benzylmaleimide, N-phenylmaleimide and N-cyclohexylmaleimide.

[0143] Examples of conjugated diene derivatives are 1,3-butadiene, isoprene and chloroprene.

[0144] The homopolymer or copolymer can be prepared by, for example, free radical polymerization, cationic polymerization, anionic polymerization or organometallic catalytic polymerization (such as Ziegler-Natta catalysis). The polymerization process can be suspension polymerization, emulsion polymerization, solution polymerization or bulk polymerization.

[0145] The organic resin generally has an average molar mass Mn (determined by GPC) of 10,000 g / mol to 1,000,000 g / mol, preferably 20,000 g / mol to 750,000 g / mol, more preferably 30,000 g / mol to 500,000 g / mol.

[0146] In some preferred embodiments, the organic resin is a thermosetting resin or an ultraviolet (UV) curable resin.In some embodiments, the organic resin is cured using a method that will facilitate roll-to-roll processing.

[0147] Thermosetting resins require curing, during which they undergo irreversible molecular crosslinking, which renders the resin infusible. In some embodiments, the thermosetting resin is an epoxy resin, a phenolic resin, a vinyl resin, a melamine resin, a urea-formaldehyde resin, an unsaturated polyester resin, a polyurethane resin, an allyl resin, an acrylic resin, a polyamide resin, a polyamide-imide resin, a phenolamine polycondensation resin, a urea-melamine polycondensation resin, or a combination thereof.

[0148] In some embodiments, the thermosetting resin is an epoxy resin. Epoxy resins cure easily without volatile emissions or byproducts from a wide range of chemicals. Epoxy resins are also compatible with most substrates and tend to wet surfaces easily. See Boyle, MA et al., "Epoxy Resins," Composites, Vol. 21, ASM Handbook, pages 78-89 (2001).

[0149] In some embodiments, the organic resin is a silicone thermosetting resin. In some embodiments, the silicone thermosetting resin is 0E6630A or 0E6630B (Dow Corning Corporation (Auburn, Michigan)).

[0150] In some embodiments, a thermal initiator is used. In some embodiments, the thermal initiator is AIBN [2,2'-azobis(2-methylpropionitrile)] or benzoyl peroxide.

[0151] UV curable resin is a polymer that will solidify and harden quickly when exposed to light of a specific wavelength. In certain embodiments, the UV curable resin is a resin having a free radical polymerization group or a cationic polymerizable group as a functional group. The free radical polymerization group is, for example, a (meth)acryloyloxy group, a vinyloxy group, a styryl group, or a vinyl group; The cationic polymerizable group is, for example, an epoxy group, a thioepoxy group, a vinyloxy group, or an oxetane group. In certain embodiments, the UV curable resin is a polyester resin, a polyether resin, a (meth)acrylic resin, an epoxy resin, a polyurethane resin, an alkyd resin, a spiroacetal resin, a polybutadiene resin, or a thioolefin resin.

[0152] In some embodiments, the UV curable resin is selected from polyurethane acrylate, allyloxylated cyclohexyl diacrylate, bis(acryloyloxyethyl)hydroxyisocyanurate, bis(acryloyloxyneopentyl glycol) adipate, bisphenol A diacrylate, bisphenol A dimethacrylate, 1,4-butanediol diacrylate, 1,4-butanediol dimethacrylate, 1,3-butanediol diacrylate, 1,3-butanediol dimethacrylate, dicyclopentyl diacrylate, diethylene glycol diacrylate, diethylene glycol dimethacrylate, dipentaerythritol hexaacrylate, dipentaerythritol monohydroxypentaacrylate, di(trimethylolpropane) tetraacrylate, triethylene glycol dimethacrylate, glyceryl methacrylate, 1,6-hexanediol diacrylate, neopentyl glycol dimethacrylate, neopentyl glycol hydroxypivalic acid diacrylate, pentaerythritol triacrylate, pentaerythritol tetraacrylate. Acrylates, phosphoric acid dimethacrylate, polyethylene glycol diacrylate, polypropylene glycol diacrylate, tetraethylene glycol diacrylate, tetrabromobisphenol A diacrylate, triethylene glycol divinyl ether, triglycerol diacrylate, trimethylolpropane triacrylate, tripropylene glycol diacrylate, tris(acryloyloxyethyl) isocyanurate, phosphoric acid triacrylate, phosphoric acid diacrylate, monopropyl acrylate, vinyl-terminated polydimethylsiloxane, vinyl-terminated diphenylsiloxane-dimethylsiloxane copolymer, vinyl-terminated polyphenylmethylsiloxane, vinyl-terminated difluoromethylsiloxane-dimethylsiloxane copolymer, vinyl-terminated diethylsiloxane-dimethylsiloxane copolymer, vinylmethylsiloxane, monomethacryloxypropyl-terminated polydimethylsiloxane, monovinyl-terminated polydimethylsiloxane, monoallyl-monotrimethylsiloxy-terminated polyethylene oxide, and combinations thereof.

[0153] In some embodiments, the UV curable resin is a thiol functional compound that can be cross-linked with an isocyanate, an epoxy resin, or an unsaturated compound under UV curing conditions. In some embodiments, the thiol functional compound is a polythiol. In some embodiments, the polythiol is pentaerythritol tetrakis (3-mercaptopropionate) (PETMP); trimethylolpropane tris (3-mercaptopropionate) (TMPMP); ethylene glycol di (3-mercaptopropionate) (GDMP); tris [25- (3-mercapto-propionyloxy) ethyl] isocyanurate (TEMPIC); dipentaerythritol hexa (3-mercaptopropionate) (Di-PETMP); ethoxylated trimethylolpropane tris (3-mercaptopropionate) (ETTMP 1300 and ETTMP 700); polycaprolactone tetrakis (3-mercaptopropionate) (PCL4MP1350); pentaerythritol tetrakis mercaptoacetate (PETMA); trimethylolpropane tris mercaptoacetate (TMPMA); or ethylene glycol dimercaptoacetate (GDMA). These compounds are commercially available from Bruno Bock (Malschacht, Germany) under the trade name sell.

[0154] In some embodiments, the UV curable resin further comprises a photoinitiator. The photoinitiator initiates a crosslinking and / or curing reaction of the photosensitive material during exposure to light. In some embodiments, the photoinitiator is an acetophenone-based, benzoin-based, or thioxanthone-based compound that can initiate polymerization, crosslinking, and curing of the monomer.

[0155] In some embodiments, the UV curable resin comprises a mercapto functional compound and a methacrylate, an acrylate, an isocyanate, or a combination thereof. In some embodiments, the UV curable resin comprises a polythiol and a methacrylate, an acrylate, an isocyanate, or a combination thereof.

[0156] In some embodiments, the photoinitiator is MINS-311RM (Minuta Technology Co., Ltd (Korea)).

[0157] In some embodiments, the photoinitiator is 127. 184. 184D, 2022, 2100, 250, 270, 2959, 369, 369EG, 379, 500, 651, 754, 784, 819, 819DW, 907, 907FF, OxeOl, TPO-L, 1173, 1173D, 4265, BP or MBF (BASF Corporation (Wyandotte, Michigan)). In some embodiments, the photoinitiator is TPO (2,4,6-trimethylbenzoyl-diphenyl-phosphine oxide) or MBF (methyl benzoylformate).

[0158] In some embodiments, the organic resin is present in an amount by weight (weight / weight) of about 20% to about 99%, about 20% to about 95%, about 20% to about 90%, about 20% to about 85%, about 20% to about 80%, about 20% to about 70%, about 20% to about 60%, about 40% to about 99%, about 40% to about 95%, about 40% to about 90%, about 40% to about 85%, about 40% to about 80%, about 40% to about 70%, about 70% to about 99%, about 70% to about 95%, about 70% to about 90%, about 70% to about 85%, about 70% to about 80%, about 80% to about 99%, about 80% to about 95%, about 80% to about 90%, about 80% to about 85%, about 85% to about 99%, about 85% to about 95%, about 85% to about 90%, about 90% to about 99%, about 90% to about 95%, or about 95% to about 99%.

[0159] The present invention also relates to a composition comprising at least one solvent. In a preferred embodiment, the composition according to the present invention is a solution.

[0160] In another preferred embodiment, the composition according to the present invention is a suspension.

[0161] The composition in the embodiment of the present invention may include 0.01 wt % to 20 wt % of the luminophore E, preferably 0.1 wt % to 20 wt %, more preferably 0.2 wt % to 20 wt %, and most preferably 2 wt % to 15 wt % of the luminophore E.

[0162] The composition of the present invention can be used to form a color conversion layer using methods such as inkjet printing, transfer printing, and photolithography. In this case, the organic compound H (i.e., the color conversion material) is dissolved alone or in combination with other materials in a resin (prepolymer) and / or solvent to form an ink. The mass concentration of the organic compound H (i.e., the color conversion material) in the ink is not less than 0.1 wt%. The color conversion capability of the color conversion layer can be improved by adjusting the concentration of the color conversion material in the ink and the thickness of the color conversion layer. Generally speaking, a higher concentration of the color conversion material or a greater thickness of the color conversion material results in a higher color conversion efficiency of the color conversion layer.

[0163] In some preferred embodiments, the solvent is selected from water, alcohol, ester, aromatic ketone or aromatic ether, aliphatic ketone or aliphatic ether, or inorganic ester compounds such as borate or phosphate, or a combination of two or more solvents.

[0164] In other embodiments, suitable and preferred solvents are aliphatic, cycloaliphatic or aromatic hydrocarbons, amines, thiols, amides, nitriles, esters, ethers, polyethers, alcohols, diols or polyols.

[0165] In other embodiments, alcohols represent a suitable class of solvents. Preferred alcohols include alkylcyclohexanols, particularly methylated aliphatic alcohols, naphthols, and the like.

[0166] Other examples of suitable alcohol solvents include: dodecanol, phenyl tridecanol, benzyl alcohol, ethylene glycol, ethylene glycol methyl ether, glycerol, propylene glycol, propylene glycol ethyl ether and the like.

[0167] The solvent can be used alone or as a combination of two or more organic solvents.

[0168] Further, examples of organic solvents include (but are not limited to): methanol, ethanol, 2-methoxyethanol, dichloromethane, chloroform, chlorobenzene, o-dichlorobenzene, tetrahydrofuran, anisole, morpholine, toluene, o-xylene, m-xylene, p-xylene, 1,4-dioxane, acetone, methyl ethyl ketone, 1,2-dichloroethane, 3-phenoxytoluene, 1,1,1-trichloroethane, 1,1,2,2-tetrachloroethane, ethyl acetate, butyl acetate, dimethylformamide, dimethylacetamide, dimethyl sulfoxide, tetralin, decalin, indene and / or combinations thereof.

[0169] In some preferred embodiments, according to a composition of the present invention, the solvent is selected from aromatic or heteroaromatic compounds, esters, aromatic ketones or aromatic ethers, aliphatic ketones or aliphatic ethers, alicyclic or olefinic compounds, or inorganic ester compounds such as borate or phosphate esters, or a combination of two or more solvents.

[0170] Examples of aromatic or heteroaromatic solvents according to the present invention include, but are not limited to: 1-tetralone, 3-phenoxytoluene, acetophenone, 1-methoxynaphthalene, p-diisopropylbenzene, pentylbenzene, tetralin, cyclohexylbenzene, chloronaphthalene, 1,4-dimethylnaphthalene, 3-isopropylbiphenyl, p-methylisopropylbenzene, dipentylbenzene, o-diethylbenzene, m-diethylbenzene, p-diethylbenzene, 1,2,3,4-tetramethylbenzene, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, butylbenzene, dodecylbenzene, 1-methylnaphthalene, 1,2,4 -Trichlorobenzene, 1,3-dipropoxybenzene, 4,4-difluorodiphenylmethane, diphenyl ether, 1,2-dimethoxy-4-(1-propenyl)benzene, diphenylmethane, 2-phenylpyridine, 3-phenylpyridine, 2-phenoxymethyl ether, 2-phenoxytetrahydrofuran, ethyl-2-naphthyl ether, N-methyldiphenylamine, 4-isopropylbiphenyl, α,α-dichlorodiphenylmethane, 4-(3-phenylpropyl)pyridine, benzyl benzoate, 1,1-bis(3,4-dimethylphenyl)ethane, 2-isopropylnaphthalene, dibenzyl ether, etc.

[0171] In other embodiments, suitable and preferred solvents are aliphatic, alicyclic or aromatic hydrocarbons, amines, thiols, amides, nitriles, esters, ethers, polyethers.

[0172] The solvent may be a cycloalkane, such as decalin.

[0173] In other preferred embodiments, a composition according to the present invention comprises at least 50 wt% of an alcohol solvent, preferably at least 80 wt% of an alcohol solvent, and particularly preferably at least 90 wt% of an alcohol solvent.

[0174] In some preferred embodiments, the solvents particularly suitable for the present invention are solvents having a Hansen solubility parameter within the following ranges:

[0175] δ d (Dispersion force) at 17.0 MPa 1 / 2 -23.2MPa 1 / 2 range, especially at 18.5MPa 1 / 2 -21.0MPa 1 / 2 scope;

[0176] δ p (Polar force) at 0.2MPa 1 / 2 -12.5MPa 1 / 2 range, especially at 2.0MPa 1 / 2 -6.0MPa 1 / 2 scope;

[0177] δ h (Hydrogen bond force) at 0.9MPa 1 / 2 -14.2MPa 1 / 2 range, especially at 2.0MPa 1 / 2 -6.0MPa 1 / 2 range.

[0178] In the composition of the present invention, the solvent should be selected based on its boiling point. In the present invention, the boiling point of the solvent is ≥150°C; preferably ≥180°C; more preferably ≥200°C; even more preferably ≥250°C; and most preferably ≥275°C or ≥300°C. Boiling points within these ranges are beneficial for preventing nozzle clogging in inkjet printheads. The solvent can be evaporated from the solvent system to form a film containing the functional material.

[0179] In some preferred embodiments, the compositions according to the present invention:

[0180] 1) Its viscosity @25℃ is in the range of 1cps to 100cps, and / or

[0181] 2) Its surface tension @25℃ is in the range of 19 dyne / cm to 50 dyne / cm.

[0182] In the composition of the present invention, the surface tension parameters of the resin (prepolymer) or solvent should be considered when selecting. The appropriate surface tension parameters are tailored to the specific substrate and printing method. For example, for inkjet printing, in a preferred embodiment, the surface tension of the resin (prepolymer) or solvent at 25°C is approximately in the range of 19 dyne / cm to 50 dyne / cm; more preferably, in the range of 22 dyne / cm to 35 dyne / cm; and most preferably, in the range of 25 dyne / cm to 33 dyne / cm.

[0183] In a preferred embodiment, the surface tension of the composition according to the present invention at 25°C is in the range of about 19 dyne / cm to 50 dyne / cm; more preferably in the range of 22 dyne / cm to 35 dyne / cm; and most preferably in the range of 25 dyne / cm to 33 dyne / cm.

[0184] According to the composition of the present invention, the viscosity parameters of the ink need to be considered when selecting the resin (prepolymer) or solvent. The viscosity can be adjusted by different methods, such as by selecting a suitable resin (prepolymer) or solvent and the concentration of the functional material in the ink. In a preferred embodiment, the viscosity of the resin (prepolymer) or solvent is less than 100 cps; more preferably less than 50 cps; and most preferably 1.5 cps to 20 cps. The viscosity here refers to the viscosity at the ambient temperature during printing, generally 15°C to 30°C, preferably 18°C ​​to 28°C, more preferably 20°C to 25°C, and most preferably 23°C to 25°C. The composition thus formulated will be particularly suitable for inkjet printing.

[0185] In a preferred embodiment, the composition according to the present invention has a viscosity at 25°C in the range of about 1 cps to 100 cps; more preferably in the range of 1 cps to 50 cps; and most preferably in the range of 1.5 cps to 20 cps.

[0186] The ink obtained from the resin (prepolymer) or solvent that satisfies the above-mentioned boiling point, surface tension parameters, and viscosity parameters can form a functional material film with uniform thickness and composition properties.

[0187] The present invention further relates to an organic functional material film, comprising a mixture as described above, or prepared using a composition as described above.

[0188] The present invention also provides a method for preparing the organic functional material thin film, comprising the following steps:

[0189] 1) Prepare a composition according to the invention.

[0190] 2) coating the composition on a substrate to form a thin film by printing or coating, wherein the printing or coating method is selected from inkjet printing, nozzle printing, letterpress printing, screen printing, dip coating, spin coating, doctor blade coating, roller printing, twist roller printing, offset printing, flexographic printing, rotary printing, spraying, brushing or pad printing, and slot extrusion coating.

[0191] 3) The obtained film is heated to at least 50° C. or exposed to ultraviolet light to cause a cross-linking reaction and solidify the film.

[0192] The thickness of the organic functional material film is generally 50nm to 100μm, preferably 100nm to 50μm, more preferably 300nm to 30μm, even more preferably 300nm to 10μm, and most preferably 300nm to 4μm.

[0193] The present invention also provides applications of the composition and the organic functional material film in optoelectronic devices.

[0194] In some embodiments, the optoelectronic device may be selected from a color converter, an organic light emitting diode (OLED), an organic photovoltaic cell (OPV), an organic light emitting cell (OLEEC), an organic light emitting field effect transistor, and an organic laser.

[0195] Furthermore, the present invention provides a photoelectric device comprising the above mixture or composition or organic functional material film.

[0196] Preferably, the optoelectronic device is an electroluminescent device, such as a color converter, an organic light-emitting diode (OLED), an organic light-emitting cell (OLEEC), an organic light-emitting field-effect transistor (OLED), a perovskite light-emitting diode (PeLED), and a quantum dot light-emitting diode (QD-LED), wherein a functional layer comprises a thin film of one of the above-mentioned organic functional materials. The functional layer can be selected from a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, a light-emitting layer, a cathode passivation layer (CPL), or a translucent encapsulation layer (TFE).

[0197] In a preferred embodiment, the optoelectronic device is an electroluminescent device comprising two electrodes, and the functional layer is located on the same side of the two electrodes.

[0198] In another preferred embodiment, the optoelectronic device comprises a light-emitting unit and a color conversion layer (functional layer), wherein the color conversion layer comprises one of the above-mentioned mixtures or compositions or a thin film of an organic functional material.

[0199] In certain embodiments, the color conversion layer absorbs ≤60%, preferably ≤50%, more preferably ≤40%, and most preferably ≤30% or more of the light from the light-emitting units. In these embodiments, the color conversion layer can produce multi-color light, or even white light. In a preferred embodiment, the color conversion layer absorbs 95% or more, preferably 97% or more, more preferably 99% or more, and most preferably 99.9% or more of the light from the light-emitting units.

[0200] In certain preferred embodiments, the light-emitting unit is selected from a solid-state light-emitting device. The solid-state light-emitting device is preferably selected from an LED, an organic light-emitting diode (OLED), an organic light-emitting cell (OLEEC), an organic light-emitting field-effect transistor, a perovskite light-emitting diode (PeLED), a quantum dot light-emitting diode (QD-LED), or a nanorod LED (nanorod LED, see DOI: 10.1038 / srep28312).

[0201] In a preferred embodiment, the light emitting unit emits blue light, which is converted into green light or red light by the color conversion layer.

[0202] In another preferred embodiment, the light emitting unit emits green light, which is converted into yellow light or red light by the color conversion layer.

[0203] The present invention further relates to a display comprising at least three types of pixels: red, green, and blue. As shown in FIG1 , the blue pixel comprises a blue light emitting unit, and the red and green pixels comprise a blue light emitting unit and corresponding red and green color conversion layers.

[0204] The present invention further relates to an organic light-emitting device comprising, from bottom to top, a first electrode, an organic light-emitting layer, a second electrode, a color conversion layer, and an encapsulation layer (e.g., the outermost encapsulation layer). The second electrode is at least partially transparent, and the color conversion layer at least partially absorbs light emitted by the organic light-emitting layer that passes through the second electrode. The color conversion layer comprises a mixture as described above, or is prepared using a composition as described above. Preferably, the emission spectrum of the organic compound H is on the short-wavelength side of the absorption spectrum of the luminophore E, and at least partially overlaps with it. Preferably, the full width at half maximum (FWHM) of the emission spectrum of the luminophore E is less than or equal to 55 nm. The luminescent layer may comprise an organic material, quantum dots, or a perovskite material as the luminescent material.

[0205] The organic light-emitting device may further include a substrate, which may be located below the first electrode or above the second electrode.

[0206] The organic compound H and the luminophore E and their preferred embodiments are as described above.

[0207] In some embodiments, the color conversion layer absorbs ≤60%, preferably ≤50%, more preferably ≤40%, and most preferably ≤30% or more of the light emitted by the organic light emitting layer that passes through the second electrode.

[0208] In a preferred embodiment, the color conversion layer can absorb 95% or more, preferably 97% or more, more preferably 99% or more, and most preferably 99.9% or more of the light emitted by the organic light-emitting layer and transmitted through the second electrode.

[0209] In some embodiments, the thickness of the color conversion layer is between 100 nm and 20 μm, preferably between 150 nm and 10 μm, more preferably between 200 nm and 8 μm, and most preferably between 200 nm and 6 μm.

[0210] In other embodiments, the thickness of the color conversion layer is between 200 nm and 4 μm, preferably between 200 nm and 3 μm, more preferably between 200 nm and 2.5 μm, and most preferably between 200 nm and 2 μm.

[0211] In a preferred embodiment, the organic light emitting device is an OLED. More preferably, the first electrode is an anode and the second electrode is a cathode. Particularly preferably, the organic light emitting device is a top emission OLED.

[0212] The substrate can be opaque or transparent. A transparent substrate can be used to make a transparent light-emitting device. For example, see Bulovic et al. Nature 1996, 380, p29, and Gu et al., Appl. Phys. Lett. 1996, 68, p2606. The substrate can be rigid or elastic. The substrate can be plastic, metal, semiconductor wafer or glass. It is best if the substrate has a smooth surface. Substrates without surface defects are particularly ideal. In a preferred embodiment, the substrate is flexible and can be selected from a polymer film or plastic with a glass transition temperature (Tg) of above 150°C, preferably above 200°C, more preferably above 250°C, and most preferably above 300°C. Examples of suitable flexible substrates are polyethylene terephthalate (PET) and polyethylene glycol (2,6-naphthalene) (PEN).

[0213] The anode may comprise a conductive metal or metal oxide, or a conductive polymer. The anode can readily inject holes into the hole injection layer (HIL), hole transport layer (HTL), or light-emitting layer. In a preferred embodiment, the absolute value of the difference between the work function of the anode and the HOMO energy level or valence band energy level of the light-emitting material in the light-emitting layer or the p-type semiconductor material serving as the HIL, HTL, or electron blocking layer (EBL) is less than 0.5 eV, preferably less than 0.3 eV, and most preferably less than 0.2 eV. Examples of anode materials include, but are not limited to, Al, Cu, Au, Ag, Mg, Fe, Co, Ni, Mn, Pd, Pt, ITO, aluminum-doped zinc oxide (AZO), and the like. Other suitable anode materials are known and can be readily selected for use by one of ordinary skill in the art. The anode material can be deposited using any suitable technique, such as a suitable physical vapor deposition method, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), and the like. In certain embodiments, the anode is patterned. Patterned ITO conductive substrates are commercially available and can be used to prepare the organic light emitting device according to the present invention.

[0214] The cathode can include a conductive metal or metal oxide. The cathode can easily inject electrons into the EIL or ETL or directly into the light-emitting layer. In a preferred embodiment, the absolute difference between the work function of the cathode and the LUMO energy level or conduction band energy level of the luminophore in the light-emitting layer or the n-type semiconductor material serving as the electron injection layer (EIL), electron transport layer (ETL), or hole blocking layer (HBL) is less than 0.5 eV, preferably less than 0.3 eV, and most preferably less than 0.2 eV. In principle, all materials that can be used as cathodes in OLEDs can be used as cathode materials for the organic light-emitting device of the present invention. Examples of cathode materials include, but are not limited to, Al, Au, Ag, Ca, Ba, Mg, LiF / Al, MgAg alloys, BaF2 / Al, Cu, Fe, Co, Ni, Mn, Pd, Pt, ITO, and the like. The cathode material can be deposited using any suitable technique, such as a suitable physical vapor deposition method, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), and the like. In a preferred embodiment, the cathode has a transmittance of ≥40% in the range of 400 nm to 680 nm, preferably ≥45%, more preferably ≥50%, and most preferably ≥60%. A Mg:Ag alloy of 10 nm to 20 nm in thickness can be used as the transparent cathode, with a Mg:Ag ratio ranging from 2:8 to 0.5:9.5.

[0215] When the organic light-emitting device is an OLED, the light-emitting layer preferably comprises a blue fluorescent host and a blue fluorescent guest. In another preferred embodiment, the light-emitting layer comprises a blue phosphorescent host and a blue phosphorescent guest. The OLED may further comprise other functional layers, such as a hole injection layer (HIL), a hole transport layer (HTL), an electron blocking layer (EBL), an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL). Materials suitable for use in these functional layers are described in detail above and in WO2010135519A1, US20090134784A1, and WO2011110277A1. The entire contents of these three patent documents are hereby incorporated herein by reference.

[0216] Furthermore, the organic light emitting device may further include a cathode capping layer (CPL for short).

[0217] In a preferred embodiment, the CPL is located between the second electrode and the color conversion layer.

[0218] In another preferred embodiment, the CPL is located above the color conversion layer.

[0219] Materials used for CPL generally need to have a higher refractive index n, such as n ≥ 1.95 @ 460nm, preferably n ≥ 1.90 @ 520nm, and even better n ≥ 1.85 @ 620nm. Examples of materials used for CPL include:

[0220] More examples of further CPL materials can be found in the following patent documents: KR20140128653A, KR20140137231A, KR20140142021A, KR20140142923A, KR20140143618A, KR20140145370A, KR20150004099A, KR20150012835A, US9496520B2, US2015069350A1, CN10382 8485B, CN104380842B, CN105576143A, TW201506128A, CN103996794A, CN103996795A, CN104744450A, CN104752619A, CN101944570A, US2016308162A1, US9095033B2, US2014034942A1, WO2017014357A1; the above patent documents are hereby incorporated into this document for reference.

[0221] In a preferred embodiment, the color conversion layer comprises one of the aforementioned CPL materials. In a particularly preferred embodiment, the color conversion layer is formed by co-evaporation of one of the aforementioned CPL materials, the organic compound H, and the luminophore E. In certain embodiments, the weight ratio of the organic compound H is 50%-20%, and the weight ratio of the luminophore E is 3%-15%.

[0222] Preferably, in the above-mentioned organic light-emitting device, the encapsulation layer is a thin film encapsulation (TFE).

[0223] The present invention further relates to a display panel, wherein at least one pixel comprises the above-mentioned organic light-emitting device.

[0224] The organic light-emitting device may be selected from, but is not limited to, a color converter, an organic light-emitting diode (OLED), an organic photovoltaic cell (OPV), an organic light-emitting cell (OLEEC), an organic field-effect transistor (OFET), an organic light-emitting field-effect transistor, an organic laser, an organic spintronic device, an organic sensor, and an organic plasmon emitting diode (Organic Plasmon Emitting Diode), etc., and is particularly preferably an organic electroluminescent device, such as an OLED, an OLEEC, and an organic light-emitting field-effect transistor.

[0225] Example

[0226] The present invention will be described below in conjunction with preferred embodiments, but the present invention is not limited to the following embodiments. It should be understood that the appended claims summarize the scope of the present invention. Under the guidance of the concept of the present invention, those skilled in the art should realize that certain changes made to the various embodiments of the present invention will be covered by the spirit and scope of the claims of the present invention.

[0227] Example 1: Compound Synthesis Example

[0228] 1. Synthesis of Compound 1

[0229] 6-Bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (65.44 g, 245.1 mmol), N,N-diphenyl-1,4-phenylenediamine (63.73 g, 245.1 mmol), palladium acetate (0.56 g, 2.45 mmol), sodium tert-butoxide (47.06 g, 490.2 mmol), and 500 mL of toluene were added to a 1000 mL dry, clean three-necked flask. The mixture was evacuated and filled with nitrogen three times, and then heated to 100°C and refluxed for 5 hours. After the reaction was completed, the mixture was cooled to room temperature and extracted three times with ethyl acetate and saturated brine. The organic phase was concentrated and passed through a short silica gel column (eluent: dichloromethane:n-hexane = 1:10). The product was collected and concentrated to obtain 45 g of solid intermediate 1a in a yield of 93.7%.

[0230] Intermediate 1a (88.00 g, 197.3 mmol), 9,10-dibromoanthracene (16.2 g, 48.3 mmol), Pd-132 (0.62 g, 0.97 mmol), sodium tert-butoxide (16.8 g, 175.3 mmol), and 1 L of xylene were added to a 2000 mL dry, clean three-necked flask. After three cycles of evacuation and nitrogen refilling, the mixture was heated to 140°C and refluxed for 12 hours. After the reaction, the mixture was cooled to room temperature and extracted three times with ethyl acetate and saturated brine. The organic phase was concentrated, and the product was dissolved in hot toluene and passed through an insulated silica gel column while still hot. The filtrate was collected, concentrated, slurried with n-hexane, and filtered. The filter cake was rinsed with n-hexane to obtain 5.1 g of crude product. The crude product was slurried with tetrahydrofuran and filtered while still hot to obtain 1 g of solid powdered compound 1, with a yield of 12.1%.

[0231] 2. Synthesis of Compound 2

[0232] 1-(4-bromophenyl)-2-(4-methoxyphenyl)-1,2-phenylene (107.84 g, 245.1 mmol), nBuLi (47.06 g, 490.2 mmol), and 500 mL of DMF were added to a 1000 mL dry, clean three-necked flask. The mixture was evacuated and nitrogen-filled for three cycles. The liquid nitrogen was cooled to -78°C and refluxed for 5 hours. After the reaction, the mixture was warmed to room temperature and extracted three times with ethyl acetate and saturated brine. The organic phase was concentrated and passed through a short silica gel column (eluent: dichloromethane:n-hexane = 1:10). The product was collected and concentrated to obtain the solid intermediate 2.

[0233] Intermediate 2 (19.62 g, 50.3 mmol), CH2(CN)2 (3.2 g, 48.3 mmol), Et3N (1.61 mmol) and 500 mL of ethanol were added to a 1000 mL dry, clean three-necked flask. After vacuuming and nitrogen filling for three cycles, the reaction was allowed to proceed at room temperature for 12 hours. After the reaction was completed, ethyl acetate and saturated brine were added and extracted three times. The organic phase was concentrated, and the product was dissolved in hot toluene and passed through an insulated silica gel column while hot. The filtrate was collected and rotary evaporated to obtain compound 2 as a solid powder.

[0234] 3. Synthesis of Compound 3

[0235] Using the same reaction steps as compound 2, compound 3 was obtained by replacing 1-(4-bromophenyl)-2-(4-methoxyphenyl)-1,2-phenylethylene with 1-(4-bromophenyl)-2,2-di(4-methoxyphenyl)-1-phenylethylene.

[0236] 4. Synthesis of Compound 4

[0237] Using the same reaction steps as compound 2, compound 4 was obtained by replacing 1-(4-bromophenyl)-2-(4-methoxyphenyl)-1,2-phenylethylene with [1-(4-bromophenyl)-1,2,2-tri(4-methoxyphenyl)]ethylene.

[0238] 5. Synthesis of Compound 5

[0239] 2,3-bis(4-bromophenyl)-2-butene dicarbonitrile (300 mg, 0.77 mmol), carbazole (283 g, 1.69 mmol) and dry toluene (80 mL) were mixed in a round-bottom flask with a stirring bar, and then Pd(OAc)2(3%), P(t-Bu)3(7%), and Cs2CO3(990 mg, 3.04 mmol) were added. After three cycles of vacuum and nitrogen filling, the mixture was heated to 110°C and refluxed for 30 hours. After the reaction was completed, the mixture was cooled to room temperature, extracted three times with ethyl acetate and saturated brine, and the organic phase was concentrated. The product was dissolved in hot toluene and passed through a heat-insulated silica gel column while hot. The filtrate was collected and rotary evaporated to obtain compound 5 as a solid powder.

[0240] 6. Synthesis of Compound 6

[0241] The same reaction steps as compound 5 were used to obtain compound 6 by replacing carbazole with N-phenyl-1-naphthylamine.

[0242] 7. Synthesis of Compound 7

[0243] The same reaction steps as compound 5 were used to obtain compound 7 by replacing carbazole with 1-(4-phenylboronic acid pinacol ester)-1,2,2-triphenylethylene.

[0244] 8. Synthesis of Compound 8

[0245] Diphenylamine (500 mg, 2.96 mmol), 1,6-dibromopyrene (520 mg, 1.44 mmol), Pd-132 (90 mg, 0.13 mmol), X-Phos (0.27 mg, equivalent to the catalyst), sodium tert-butoxide (1 g, 10.42 mmol), and 500 mL of xylene were added to a 1000 mL dry, clean three-necked flask. After three cycles of evacuation and nitrogen filling, the mixture was heated to 140°C and refluxed for 12 hours. After the reaction was completed, the mixture was cooled to room temperature and extracted three times with dichloromethane and saturated brine. The organic phase was concentrated and the product was dissolved in hot toluene and passed through an insulated silica gel column while hot. The filtrate was rotary evaporated to obtain intermediate 8-1 as a solid powder.

[0246] Intermediate 8-1 (750 mg, 1.4 mmol), liquid bromine (672 mg, 4.2 mmol), iodine (1.07 g, 4.2 mmol), and 500 mL of DCM were added to a 1000 mL dry, clean three-necked flask. After three cycles of vacuum and nitrogen filling, the mixture was allowed to react at room temperature for 12 hours. After the reaction, dichloromethane and saturated brine were added and extracted three times. The organic phase was concentrated and the product was dissolved in hot toluene and passed through an insulated silica gel column while hot. The filtrate was rotary evaporated to obtain intermediate 8-2 as a solid powder.

[0247] The intermediate 8-2 (900 mg, 1.3 mmol), 1-(4-phenylboronic acid pinacol ester)-1,2,2-triphenylethylene (1000 mg, 3.02 mmol), Pd(PPh3)4 (0.13 mmol), K2CO3 (10.42 mmol), and 500 mL of toluene were added to a 1000 mL dry, clean three-necked flask. After vacuuming and nitrogen filling for three cycles, the mixture was heated to 140 ° C and refluxed for 24 hours. After the reaction was completed, the mixture was cooled to room temperature, extracted three times with dichloromethane and saturated brine, and the organic phase was concentrated. The product was dissolved in hot toluene and passed through an insulated silica gel column while hot. The filtrate was rotary evaporated to obtain compound 8 as a solid powder.

[0248] 9. Synthesis of Compound 9

[0249] 1-(4-Bromophenyl)-1,2,2-phenylethylene (700 mg, 1.71 mmol), naphthylamine (270 mg, 1.89 mmol), Pd2(dba)3 (3%), P(t-Bu)3 (7%), potassium tert-butoxide (5.67 mmol), and 500 mL of toluene were added to a round-bottom flask with a stirring bar and mixed. After three cycles of vacuum evacuation and nitrogen filling, the mixture was heated to 140°C and refluxed for 30 hours. After the reaction was completed, the mixture was cooled to room temperature and extracted three times with ethyl acetate and saturated brine. The organic phase was concentrated, and the product was dissolved in hot toluene and passed through an insulated silica gel column while hot. The filtrate was collected and rotary evaporated to obtain the crude intermediate 9.

[0250] Intermediate 9 (800 mg, 1.69 mmol), 4,7-bis(4-bromophenyl)benzo[C][1,2,5]thiadiazole (343 mg, 0.77 mmol), Pd(OAc)2(3%), P(t-Bu)3(7%), Cs2CO3(3.04 mmol) and 100 mL of toluene were added to a round-bottom flask. After three cycles of vacuum and nitrogen filling, the mixture was heated to 140°C and refluxed for 30 hours. After the reaction was completed, the mixture was cooled to room temperature and extracted three times with ethyl acetate and saturated brine. The organic phase was concentrated and the product was dissolved in hot toluene and passed through an insulated silica gel column while hot. The filtrate was collected and rotary evaporated to obtain compound 9 as a solid powder.

[0251] 10. Synthesis of Compound 10

[0252] Bis(phenylethynyl)dimethylsilane (2600 mg, 10 mmol), lithium naphthalene (3225 mg, 25 mmol), and 1000 mL of THF were added to a round-bottom flask with a stir bar. After three cycles of vacuum and nitrogen filling, the mixture was allowed to react at room temperature for 12 hours. After completion of the reaction, the mixture was filtered to obtain a crude intermediate 10-1.

[0253] Intermediate 10-1 (1600 mg, 5.84 mmol), dichloro(N,N,N',N'-tetramethylethylenediamine)zinc (3780 mg, 15 mmol), and 1000 mL of THF were added to a round-bottom flask with a stir bar. The mixture was vacuumed and filled with nitrogen three times, and then reacted at room temperature for 12 hours. After the reaction, the mixture was extracted three times with ethyl acetate and saturated brine. The organic phase was concentrated and the product was dissolved in hot THF and passed through an insulated silica gel column while hot. The filtrate was collected and rotary evaporated and dried to obtain the crude product of intermediate 10-2.

[0254] Intermediate 10-2 (1800 mg, 3.9 mmol), 2-(4-bromophenyl)-1,3-dioxolane (2290 mg, 10 mmol), and 500 mL of THF were added to a round-bottom flask with a stir bar. After three cycles of vacuum and nitrogen filling, the mixture was heated and refluxed for 24 hours. After the reaction was completed, the mixture was cooled to room temperature and extracted three times with ethyl acetate and saturated brine. The organic phase was concentrated and the product was dissolved in hot THF and passed through an insulated silica gel column while hot. The filtrate was collected and rotary evaporated and dried to obtain the crude intermediate 10-3.

[0255] Intermediate 10-3 (1400 mg, 2.98 mmol), CH2(CN)2 (530 mg, 8.03 mmol) and 500 mL of ethanol were added to a round-bottom flask. After three cycles of vacuum and nitrogen filling, the temperature was raised and refluxed for 24 hours. After the reaction was completed, the mixture was cooled to room temperature and extracted three times with ethyl acetate and saturated brine. The organic phase was concentrated and the product was dissolved in hot toluene and passed through an insulated silica gel column while hot. The filtrate was collected and rotary evaporated and dried to obtain compound 10 as a solid powder.

[0256] The structure of E1 as a red light guest is as follows. The synthesis of E1 can be found in Yue Wang, et al., Angew. Chem., 2023, 135, e202216473. The structure of E2 as a green light guest is as follows. The synthesis of E2 can be found in the prior patent application with application number CN202211429395.8.

[0257] Example 2: Energy level structure of the compound

[0258] The energy levels of organic materials can be calculated through quantum calculations, such as using TD-DFT (time-dependent density functional theory) with Gaussian 09W (Gaussian Inc.). For detailed simulation methods, see WO2011141110. The molecular geometry is first optimized using the density functional theory method "Ground State / DFT / Default Spin / B3LYP" with the basis set "6-31G(d)" (Charge 0 / Spin Singlet). The energy structure of the organic molecule is then calculated using the TD-DFT (time-dependent density functional theory) method "TD-SCF / DFT / Default Spin / B3PW91" with the basis set "6-31G(d)" (Charge 0 / Spin Singlet). The HOMO and LUMO energy levels are calculated using the following calibration formulas, with S1 and T1 used directly.

[0259] HOMO(eV)=((HOMO(G)×27.212)-0.9899) / 1.1206

[0260] LUMO(eV)=((LUMO(G)×27.212)-2.0041) / 1.385

[0261] The HOMO (G) and LUMO (G) are directly calculated using Gaussian 09W, with units in Hartree. The results are shown in Table 1 below.

[0262] Table 1

[0263] Example 3: Solubility of Compounds

[0264] The solubility of the compound in toluene was determined as follows:

[0265] 1. Place 1000 mg of toluene solution in a clear glass sample bottle.

[0266] 2. Weigh a certain amount of compound and dissolve it in toluene. Shake and let it stand until it is completely dissolved.

[0267] 3. After the compound is completely dissolved, continue to weigh a certain amount of compound and dissolve it in toluene, shake and let it stand.

[0268] 4. Repeat the above steps until a precipitate appears and the compound no longer dissolves.

[0269] 5. Record the total mass of compound added and calculate the solubility.

[0270] The solubilities of Compounds 1-10 and E1-E2 in toluene are shown in Table 2 below.

[0271] Table 2

[0272] Example 4: Absorption and emission spectra, molar absorption coefficient, and fluorescence quantum yield PLQY of the compound (comparison of solution and film)

[0273] The molar absorption coefficient of the compound and its absorption and emission spectra and PLQY in solution were determined as follows:

[0274] 1. Use a volumetric flask to prepare a toluene solution of the compound with a certain molar concentration.

[0275] 2. Use a UV-visible spectrophotometer (Puxi T9s) to measure the absorption spectrum of the solution and obtain the absorption peak position.

[0276] 3. The absorbance of the maximum absorption peak divided by the equivalent concentration of the solution substance is the molar absorption coefficient of the compound.

[0277] 4. The emission spectrum of the solution was measured using a fluorescence spectrometer (Hitachi, F-4700FL Spectrophotometer) to obtain the emission peak position.

[0278] 5. The PLQY of the compound solution was determined by relative method, with Rhodamine 101 as the standard.

[0279] The absorption and emission spectra of the compounds in the thin films were measured by the following method:

[0280] 1. Prepare a toluene solution of the compound with a certain concentration.

[0281] 2. Apply the prepared toluene solution on a clean glass substrate.

[0282] 3. Spin coating and baking at 80℃ for 1 min to obtain a compound film.

[0283] 4. Use a UV-visible spectrophotometer (Puxi T9s) to measure the absorption spectrum of the film and obtain the absorption peak position.

[0284] 5. The emission spectrum of the film was measured using a fluorescence spectrometer (Hitachi, F-4700FL Spectrophotometer) to obtain the emission peak position.

[0285] 6. The PLQY of the film was measured using a fluorescence spectrometer with an integrating sphere (Hitachi, F-4700FL Spectrophotometer) using the absolute method.

[0286] The molar absorption coefficients of the compounds and their absorption and emission peaks in solution and film are shown in Table 3 below.

[0287] Table 3

[0288] Table 3 shows that Compounds 1-10 all have low PLQYs in solution, but significantly enhance them in thin films, demonstrating AIE properties. Figures 2-3 show the absorption and emission spectra of Compound 1 in toluene solution and thin films. These figures demonstrate that the absorption and emission spectra of Compound 1 in solution and thin films are very similar, with the spectrum even blue-shifted in the thin film.

[0289] FIG4 shows the absorption and emission spectra of a toluene solution of Compound E1.

[0290] Example 5: Emission spectra of compounds in H2O / THF solvents with different H2O volume fractions

[0291] The emission spectrum of the compound was measured as follows:

[0292] 1. Prepare H2O / THF solvents with different H2O volume fractions.

[0293] 2. The same volume of H2O / THF solvent with different H2O volume fractions was added to the same mass of compound.

[0294] 3. The emission spectrum of the solution was measured using a fluorescence spectrometer (Hitachi, F-4700FL Spectrophotometer) to obtain the emission peak intensity.

[0295] Figure 5(a) shows the emission spectra of compound 1 in H2O / THF solvents with varying H2O volume fractions. Figure 5(b) shows the relationship between the emission peak intensity of compound 1 solutions and the H2O volume fraction. Figure 5(c) shows images of compound 1 in H2O / THF solvents with varying H2O volume fractions under UV illumination. Clearly, the fluorescence intensity of compound 1 in THF / H2O solvents increases with increasing H2O content, demonstrating a distinct AIE characteristic.

[0296] Example 6: UV stability of compounds

[0297] The test method for the UV stability of the compound is as follows:

[0298] Prepare 1×10 -5 mol / L concentration of toluene solution, take 3mL and add it to a cuvette with a lid, tighten the lid, and place it in a UV-visible spectrophotometer to test the absorption spectrum. The absorbance of the maximum absorption peak is recorded as the initial value. Place the cuvette at a distance of 100 nm from the UV LED (365 nm, 50 mW / cm 2 ) at a position of 12 cm, irradiate for a period of time, take out the test absorption spectrum, continue irradiation after the test, and repeat this process until the absorbance decays to 80% of the original value. Record the time, which is recorded as t80.

[0299] The t80 of each compound is shown in Table 4 below:

[0300] Table 4

[0301] According to Table 4 and FIG6 , the organic compound H according to the present invention has good photostability.

[0302] Example 7: Preparation of Color Conversion Film (CCL)

[0303] 7.1 Resin film: Dissolve 120 mg of compound 1 in 1 mL of 12% polystyrene toluene solution and stir for 30 min. Dissolve 3 mg of luminescent material E1 in the solution and continue stirring for 30 min. Drop the stirred solution onto a glass substrate, spin-coat it, and heat and dry it at 80°C to obtain a CCL film.

[0304] CCL based on other organic compounds can be prepared in the same way as described in 7.1.

[0305] Example 8: Results of OLED+CCL film

[0306] 1. Top-emitting blue OLED + resin CCL: On the light-emitting surface of the top-emitting blue OLED, prepare a CCL resin film (E1 as the luminescent body) according to 7.1 above, with a thickness of about 5 μm.

[0307] 3. The spectra of a top-emitting blue OLED and a top-emitting blue OLED + resin CCL were measured using a luminance meter (Foshida, CS-2000A). Figure 8 shows the top-emitting blue OLED + resin CCL (E1 as the luminescent material). The blue light from the top-emitting OLED is essentially completely absorbed and converted into narrow-spectrum red light.

[0308] The technical features of the above-mentioned embodiments can be combined arbitrarily. In order to make the description concise, not all possible combinations of the technical features in the above-mentioned embodiments are described. However, as long as there is no contradiction in the combination of these technical features, they should be considered to be within the scope of this specification.

[0309] The above-described embodiments merely illustrate several implementations of the present invention, and while their descriptions are relatively specific and detailed, they should not be construed as limiting the scope of the patent. It should be noted that a person skilled in the art would be able to make numerous variations and improvements without departing from the spirit of the present invention, all of which fall within the scope of protection of the present invention. Therefore, the scope of protection of the patent for this invention shall be determined by the appended claims.

Claims

1. A mixture comprising an organic compound H and a luminophore E, characterized in that: 1) The organic compound H is an aggregation-induced emission material, and its emission spectrum is on the short wavelength side of the absorption spectrum of the luminophore E and at least partially overlaps with each other; 2) The half-peak width of the emission spectrum of the luminophore E is less than or equal to 55 nm.

2. The mixture according to claim 1, characterized in that The organic compound H comprises at least one structure selected from the group consisting of chemical formulas (I-1) to (I-5): in: R1-R4, R8 are substituents, which may be identical or different at each occurrence and are selected from linear alkyl, alkenyl, haloalkyl, alkoxy or thioalkoxy groups having 1 to 20 carbon atoms, or branched or cyclic alkyl, haloalkyl, alkoxy, thioalkoxy or silyl groups having 3 to 20 carbon atoms, or keto groups having 1 to 20 carbon atoms, or alkoxycarbonyl groups having 2 to 20 carbon atoms, or aryloxycarbonyl groups having 4 to 20 carbon atoms. group, or a cyano group, a carbamoyl group, a haloformyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, a CF3 group, a Cl group, a Br group, a F group, an I group, a crosslinkable group, or a substituted or unsubstituted aromatic or heteroaromatic ring system having 5 to 40 ring atoms, or an aryloxy group or heteroaryloxy group having 5 to 40 ring atoms, or an arylamine group or heteroarylamine group having 5 to 40 ring atoms, a disubstituted unit at any position of the above groups, or a combination of these groups; R5-R7, at each occurrence, may be identical or different and be selected from H, D, or a linear alkyl, alkenyl, haloalkyl, alkoxy or thioalkoxy group having 1 to 20 carbon atoms, or a branched or cyclic alkyl, haloalkyl, alkoxy, thioalkoxy or silyl group having 3 to 20 carbon atoms, or a keto group having 1 to 20 carbon atoms, or an alkoxycarbonyl group having 2 to 20 carbon atoms, or an aryloxycarbonyl group having 4 to 20 carbon atoms , or cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, CF3, Cl, Br, F, I, a crosslinkable group, or a substituted or unsubstituted aromatic or heteroaromatic ring system having 5 to 40 ring atoms, or an aryloxy or heteroaryloxy group having 5 to 40 ring atoms, or an arylamine or heteroarylamine group having 5 to 40 ring atoms, a disubstituted unit at any position of the above groups, or a combination of these groups; n is selected from integers of 0-5, and m is selected from integers of 0-4.

3. The mixture according to claim 1 or 2, characterized in that The luminophore E comprises a structural unit represented by chemical formula (1), (2), (3), or (4): in: Ar 1 -Ar 3 The same or different ones are selected from aromatic or heteroaromatic groups having 5 to 24 ring atoms; Ar 4 -Ar 5 the same or different ones selected from aromatic or heteroaromatic groups having 5 to 24 ring atoms; When Ar 4 -Ar 5 When not empty, X a and X b Independently selected from N, CR at each occurrence 6 、SiR 6 , Y a and Y b In each occurrence, independently selected from B, P=O, CR 6 、SiR 6 ; When Ar 4 or Ar 5 When it is empty, X b Selected from N, CR 6 、SiR 6 , Y a Selected from B, P=O, CR 6 、SiR 6 , X a and Y b Independently selected from NR at each occurrence 6 , CR 6 R 7 、SiR 6 R 7 、C=O、O、C=N(R 6 ), C=C(R 6 R 7 ), PR 6 、P(=O)R 6 , S, S=O or SO2; X 1 、X 2 are independently selected from empty or a bridging group; R 1 -R 7 and D, which may be identical or different on each occurrence, or a linear alkyl, haloalkyl, alkoxy or thioalkoxy radical having 1 to 20 C atoms, or a branched or cyclic alkyl, haloalkyl, alkoxy, thioalkoxy or silyl radical having 3 to 20 C atoms, or a keto radical having 1 to 20 C atoms, or an alkoxycarbonyl radical having 2 to 20 C atoms, or an aryloxycarbonyl radical having 4 to 20 C atoms, or a cyano, carbamoyl, haloformyl, formyl, isocyano, Isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, CF3, Cl, Br, F, I, a crosslinkable group, or a substituted or unsubstituted aromatic or heteroaromatic ring system having 5 to 40 ring atoms, or an aryloxy or heteroaryloxy group having 5 to 40 ring atoms, or an arylamine or heteroarylamine group having 5 to 40 ring atoms, a disubstituted unit at any position of the above groups or a combination of these groups, wherein one or more groups can form a monocyclic or polycyclic aliphatic or aromatic ring system with each other and / or the ring to which the groups are bonded.

4. The mixture according to any one of claims 1 to 3, characterized in that The luminophore E comprises a structural unit represented by one of the following chemical formulas (1a), (2a), (3a), or (4a):

5. The mixture according to any one of claims 1 to 4, characterized in that The luminophore E comprises a structural unit represented by one of the following chemical formulae (1b) to (1e) or (2b) to (2e) or (3b) to (3d) or (4b) to (4d2):

6. The mixture according to any one of claims 1 to 5, characterized in that Ar 1 、Ar 2 、Ar 3 、Ar 4 、Ar 5 Each occurrence is independently selected from one or a combination of the following structural formulas:

7. The mixture according to any one of claims 1 to 6, characterized in that The organic compound H can be polymerized to form a polymer.

8. The mixture according to any one of claims 1 to 7, characterized in that The luminophore E is selected from compounds having the following structural formula: in: X is CR 19 or N; R 11 -R 19 Each occurrence is independently selected from H, alkyl, cycloalkyl, heterocyclyl, alkenyl, cycloalkenyl, alkynyl, hydroxyl, thiol, alkoxy, alkylthio, arylether, arylthioether, aryl, heteroaryl, halogen, cyano, aldehyde, carbonyl, carboxyl, oxycarboxyl, carbamoyl, amino, nitro, silyl, siloxane, borane, phosphine oxide, and R 11 -R 19 It can form a condensed ring or an aliphatic ring with adjacent substituents.

9. A composition comprising a mixture as claimed in any one of claims 1 to 8, and an organic resin and / or a solvent.

10. The composition according to claim 9, characterized in that The organic resin is a thermosetting resin or a UV curable resin.

11. The composition according to claim 9 or 10, characterized in that The proportion of the organic resin is between 20 wt % and 99 wt %.

12. An organic functional material film comprising a mixture according to any one of claims 1 to 8, or prepared using a composition according to any one of claims 9 to 11.

13. A photovoltaic device comprising a mixture according to any one of claims 1 to 8 or an organic functional material thin film according to claim 12.

14. An organic light-emitting device comprising, from bottom to top, a first electrode, an organic light-emitting layer, a second electrode, a color conversion layer, and an encapsulation layer, wherein the second electrode is at least partially transparent, and the color conversion layer at least partially absorbs light emitted by the organic light-emitting layer that passes through the second electrode, characterized in that: The color conversion layer comprises a mixture according to any one of claims 1 to 8, or is prepared using a composition according to any one of claims 9 to 11.

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