Composition and application thereof in photoelectric field

Abstract

Provided is a composition comprising a pyrene-based organic compound H as a host material, and a luminophor E having a narrow emission spectrum. Wherein the organic compound H has higher stability, and the composition can contain an organic resin, is convenient for printing or coating film formation, and is cured by heating or ultraviolet. The invention also provides an organic light-emitting device containing a color conversion layer, the color conversion layer comprises the composition, the organic compound H absorbs light of an excitation light source and transfers energy to the luminous body E, and the luminous body E emits emergent light with narrower half-peak width after absorbing the energy of the organic compound H; these light emitting devices having a narrow half-width can be manufactured into display devices having a high color gamut.

Description

A composition 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 composition, an organic functional material film containing the composition, 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 is simple to manufacture and has a high yield. 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 as high as 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.

[0005] Previous patent applications by the present inventors 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 approach provides a new design approach for developing thinner color converters. However, the stability of the host material, including its photostability and thermal stability, still needs to be significantly improved.

[0006] Summary of the Invention

[0007] Based on this, the object of the present invention is to provide a composition and its application in the optoelectronic field.

[0008] The specific technical solutions are as follows:

[0009] The present invention provides a composition comprising an organic compound H as represented by chemical formula (I) and a luminophore E, wherein: 1) the luminescence 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 each other; 2) the full width at half maximum (FWHM) of the luminescence spectrum of the luminophore E is less than or equal to 55 nm;

[0010] Where: R 101 -R 104 and D, which may be identical or different on each occurrence, or are selected from H, D, or a linear alkyl, alkenyl, haloalkyl, alkoxy, thioalkoxy group having 1 to 20 C atoms, or a branched or cyclic alkyl, haloalkyl, alkoxy, thioalkoxy group, silyl group having 3 to 20 C atoms, or a keto group having 1 to 20 C atoms, or an alkoxycarbonyl group having 2 to 20 C atoms, or an aryloxycarbonyl group having 4 to 20 C atoms, or a cyano group (-CN), a carbamoyl group (-C(=O)NH2 ), haloformyl (-C(=O)-X wherein X represents a halogen atom), formyl (-C(=O)-H), isocyanate, 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 R 101 -R 104 At least one of them is selected from chemical formula (Ia), wherein Ar1 and Ar2 are the same or different and are selected from substituted or unsubstituted aromatic or heteroaromatic groups having 5 to 24 ring atoms, and * represents the connection site with pyrene.

[0011] Preferably, the composition further comprises at least one organic resin and / or a solvent.

[0012] The present invention also provides an organic functional material film, comprising the above-mentioned composition, or prepared using the above-mentioned composition.

[0013] The present invention also provides a photoelectric device comprising the above-mentioned composition or organic functional material film.

[0014] 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 composition as described above, or is prepared using a composition as described above.

[0015] Beneficial effects: According to the composition of the present invention, 1) the organic compound H has high stability, especially photostability; 2) after the organic compound H is formed into a film, its absorption and luminescence spectra have little or no red shift. BRIEF DESCRIPTION OF THE DRAWINGS

[0016] Figure 1: Schematic diagram of a red, green, and blue color display device;

[0017] Figure 2: Absorption and emission spectra of toluene solution of compound 1;

[0018] Figure 3: Absorption and emission spectra of a thin film of compound 1;

[0019] Figure 4: Absorption and emission spectra of toluene solution of compound 2;

[0020] Figure 5: Absorption and emission spectra of a thin film of compound 2;

[0021] Figure 6: Absorption and emission spectra of toluene solution of compound 4;

[0022] Figure 7: Absorption and emission spectra of a thin film of compound 4;

[0023] Figure 8: Absorption and emission spectra of toluene solution of compound 6;

[0024] Figure 9: Absorption and emission spectra of a thin film of compound 6;

[0025] Figure 10: Absorption and emission spectra of toluene solution of compound 7;

[0026] Figure 11: Absorption and emission spectra of a thin film of compound 7;

[0027] Figure 12: Absorption and emission spectra of toluene solution of compound 10;

[0028] Figure 13: Absorption and emission spectra of a thin film of compound 10;

[0029] Figure 14: Absorption and emission spectra of toluene solution of compound 11;

[0030] Figure 15: Absorption and emission spectra of a thin film of compound 11;

[0031] Figure 16: Absorption and emission spectra of toluene solution of compound 16;

[0032] Figure 17: Absorption and emission spectra of a thin film of compound 16;

[0033] Figure 18: Absorption and emission spectra of toluene solution of compound 17;

[0034] Figure 19: Absorption and emission spectra of a thin film of compound 17;

[0035] Figure 20: Absorption and emission spectra of toluene solution of compound 20;

[0036] Figure 21: Absorption and emission spectra of a thin film of compound 20;

[0037] Figure 22: Absorption and emission spectra of toluene solution of compound 21;

[0038] Figure 23: Absorption and emission spectra of a thin film of compound 21;

[0039] Figure 24: Absorption and emission spectra of toluene solution of compound 22;

[0040] Figure 25: Absorption and emission spectra of a thin film of compound 22;

[0041] Figure 26: Absorption and emission spectra of toluene solution of compound 23;

[0042] Figure 27: Absorption and emission spectra of a thin film of compound 23;

[0043] Figure 28: Absorption and emission spectra of toluene solution of compound 24;

[0044] Figure 29: Absorption and emission spectra of a thin film of compound 24;

[0045] Figure 30: Absorption and emission spectra of toluene solution of compound 25;

[0046] Figure 31: Absorption and emission spectra of a thin film of compound 25;

[0047] Figure 32: Absorption and emission spectra of toluene solution of compound 26;

[0048] Figure 33: Absorption and emission spectra of a thin film of compound 26;

[0049] Figure 34: Absorption and emission spectra of a toluene solution of compound E1;

[0050] Figure 35: Absorption and emission spectra of a toluene solution of compound E2;

[0051] Figure 36: Absorption and emission spectra of a toluene solution of compound E3;

[0052] Figure 37: Absorption and emission spectra of a toluene solution of compound E4;

[0053] Figure 38: Absorption and emission spectra of the toluene solution of Comparative Example 1;

[0054] Figure 39: Absorption and emission spectra of the film of Comparative Example 1;

[0055] Figure 40: Absorption attenuation graph of toluene solutions of compounds 1, 2, 4, 6, 7, 10, 11, 16, 17, 20, 22, 23, 24, 26 and Comparative Example 2 after UV irradiation;

[0056] Figure 41: Brightness decay graph of the thin films of Compound 10 and Comparative Example 1 after blue light irradiation;

[0057] Figure 42: Spectrum of top-emitting blue OLED + green CCL resin film;

[0058] Figure 43: Spectrum of bottom-emitting blue OLED + green CCL resin film;

[0059] Figure 44: Spectrum of top-emitting blue OLED + red CCL resin;

[0060] Figure 45: Spectral diagram of top-emitting blue OLED + green CCL evaporated film. DETAILED DESCRIPTION

[0061] 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.

[0062] 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.

[0063] In the present invention, main body material, matrix material, host material and matrix material have the same meaning and can be interchanged.

[0064] In the present invention, metal organic complex, metal organic complex and organometallic complex have the same meaning and can be used interchangeably.

[0065] In the present invention, printing ink, ink and ink have the same meaning and can be interchanged.

[0066] The present invention provides a composition comprising an organic compound H as represented by chemical formula (I) and a luminophore E, wherein: 1) the luminescence 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 each other; 2) the full width at half maximum (FWHM) of the luminescence spectrum of the luminophore E is less than or equal to 55 nm;

[0067] Where: R 101 -R 104 is selected from H, D, which may be identical or different on each occurrence, or a linear alkyl, alkenyl, haloalkyl, alkoxy, thioalkoxy radical having 1 to 20 C atoms, or a branched or cyclic alkyl, haloalkyl, alkoxy, thioalkoxy, 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 radical , carbamoyl, haloformyl, formyl, isocyanate, 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 R 101 -R 104 At least one of them is selected from chemical formula (Ia), wherein: Ar1 and Ar2 are the same or different and are selected from substituted or unsubstituted aromatic or heteroaromatic groups having 5-24 ring atoms, and * represents the connection site with pyrene.

[0068] In some preferred embodiments, the above R 101 -R 104 At least one of the compounds is selected from the group consisting of:

[0069] Wherein: *, Ar1 and Ar2 are as defined above; R105 -R 108 is a substituent which, on each occurrence, may be identical or different and is selected from a linear alkyl, haloalkyl, alkoxy, thioalkoxy group having 1 to 20 C atoms, or a branched or cyclic alkyl, haloalkyl, alkoxy, thioalkoxy group, a silyl group having 3 to 20 C atoms, or a keto group having 1 to 20 C atoms, or an alkoxycarbonyl group having 2 to 20 C atoms, or an aryloxycarbonyl group having 4 to 20 C atoms, or a cyano group, a carbamoyl, a haloformyl, a formyl group, an isocyanate, an isocyanate, a thiocyanate, an isothiocyanate, a hydroxyl group, a nitro group, 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 arylamino or heteroarylamino group having 5 to 40 ring atoms, or a combination thereof.

[0070] In some preferred embodiments, R 105 -R 108 is selected from a linear alkyl, haloalkyl, alkoxy, thioalkoxy radical having 1 to 10 C atoms, a branched or cyclic alkyl, haloalkyl, alkoxy, thioalkoxy radical, a silyl radical having 3 to 10 C atoms, a keto radical having 1 to 10 C atoms, an alkoxycarbonyl radical having 2 to 10 C atoms, an aryloxycarbonyl radical having 6 to 10 C atoms, or a cyano, carbamoyl, haloformyl, formyl radical, or a thioalkyl radical. , isocyanate, 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 arylamino or heteroarylamino 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 with the ring to which the groups are bonded.

[0071] In some other preferred embodiments, the above R 101 -R 104 At least two of the same or different ones are selected from one of the chemical formulas (Ia-1) to (Ia-4).

[0072] In some other preferred embodiments, the above R 101 -R 104 At least three of them are the same or different and are selected from one of the chemical formulas (Ia-1) to (Ia-4).

[0073] In some other preferred embodiments, the above R 101 -R 104 The same or different ones are selected from one of the chemical formulae (Ia-1) to (Ia-4).

[0074] In certain preferred embodiments, the above R 101 -R 104 In, R 101 and R 103 , or R 102 and R 104 are selected from the same structural units.

[0075] In some other preferred embodiments, the above R 101 -R 104 are selected from the same structural units.

[0076] 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.

[0077] 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.

[0078] In another preferred embodiment, the luminescent body E has a fluorescence quantum efficiency (PLQY) of ≥50%, preferably ≥60%, more preferably ≥70%, and most preferably ≥80%.

[0079] In some particularly preferred embodiments, the luminophore E comprises a structural unit represented by chemical formula (1), (2), (3), or (4):

[0080] 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 radicals are selected from empty or aromatic radicals having 5 to 24 ring atoms; when Ar 4 -Ar 5 When not empty, X a and X b independently selected at each occurrence from N, C(R 6 )、Si(R 6 ), Y a and Y b independently selected at each occurrence from B, P=O, C(R 6 )、Si(R 6 ); when Ar4 or Ar 5 When it is empty, X b Selected from N, C(R 6 )、Si(R 6 ), Y a Selected from B, P=O, C(R 6 )、Si(R 6 ), X a and Y b In each occurrence, independently selected from N(R 6 )、C(R 6 R 7 )、Si(R 6 R 7 )、C=O、O、C=N(R 6 ), C=C(R 6 R 7 )、P(R 6 ), P(=O)R 6 , S, S=O or SO2; X 1 、X 2 are independently selected from empty or a bridging group;

[0081] R 1 -R 7 and D, which may be identical or different on each occurrence, or are selected from H, D, or a linear alkyl, haloalkyl, alkoxy, thioalkoxy radical having 1 to 20 C atoms, or a branched or cyclic alkyl, haloalkyl, alkoxy, thioalkoxy, 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 arylamino or heteroarylamino 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 with the ring to which the groups are bonded.

[0082] In some preferred embodiments, R 1 -R 7and D, which may be identical or different on each occurrence, or are selected from H, D, or straight-chain alkyl, haloalkyl, alkoxy, thioalkoxy radicals having 1 to 10 C atoms, or branched or cyclic alkyl, haloalkyl, alkoxy, thioalkoxy, silyl radicals having 3 to 10 C atoms, or keto radicals having 1 to 10 C atoms, or alkoxycarbonyl radicals having 2 to 10 C atoms, or aryloxycarbonyl radicals having 6 to 10 C 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 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.

[0083] In some preferred embodiments, the luminophore E comprises a structural unit represented by the following chemical formula (1a), (2a), (3a), or (4a):

[0084] Among them, Ar 1 -Ar 5 、X 1 、X 2 、R 1 -R 5 The definition of is the same as above.

[0085] 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.

[0086] In some preferred embodiments, X 1 、X 2 At least one is empty; particularly preferably, both are empty, and the luminophore E is selected from the structural unit represented by the following chemical formula (1b) or (2b) or (3b) or (4b):

[0087] Among them, Ar 1 -Ar 5 、R 1 -R 5 The definition of is the same as above.

[0088] In some preferred embodiments, X1 、X 2 At least one is a single bond; particularly preferably, both are single bonds, and the luminophore E is selected from the structural unit represented by the following chemical formula (1c) or (2c) or (3c) or (4c):

[0089] Among them, Ar 1 -Ar 5 、R 1 -R 5 The definition of is the same as above.

[0090] 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:

[0091] Wherein: R1, R2, R3 and R4 are defined as above 1 ; Dashed bonds represent bonds to adjacent structural units.

[0092] 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 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, systems such as 9,9′-spirobifluorene, 9,9-diarylfluorene, triarylamines, diaryl ethers, etc. are also considered aromatic ring systems for the purposes of this invention.

[0093] 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 105, 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 to 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 10 Substituted 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.

[0094] In certain preferred embodiments, among the organic compound H and the luminophore E, Ar1, Ar2, Ar 1 -Ar 5The same or different in each occurrence are selected from aromatic and heteroaromatic groups having 5 to 20 ring atoms; 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 by one or two R 10 Preferred aryl or heteroaryl groups include benzene, naphthalene, anthracene, phenanthrene, pyridine, benzofuran, pyrene or thiophene.

[0095] In some preferred embodiments, Ar1, Ar2, Ar 1 -Ar 5 At each occurrence, independently selected from the following structural formula:

[0096] Where: X0 is CR 11 or N; Y0 is selected from NR 11 , CR 12 R 13 , 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 101 .

[0097] Furthermore, Ar1, Ar2, 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:

[0098] In a particularly preferred embodiment, Ar1, Ar2, Ar 1 -Ar 5 It is a phenyl group.

[0099] 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):

[0100] Among them, Ar 1 -Ar 3 、X a 、Y b 、R 3 -R5 The definition of is as above.

[0101] Preferably, X in formula (1d) and (1e) a The same or different are independently selected from N(R 6 )、C(R 6 R 7 )、Si(R 6 R 7 ), O, S.

[0102] 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.

[0103] Preferably, X in chemical formulas (3d), (4d1) and (4d2) a The same or different are independently selected from N(R 6 )、C(R 6 R 7 )、Si(R 6 R 7 ), O, S.

[0104] In some other preferred embodiments, the luminophore E comprises the structural units represented by the following chemical formulas (1f) to (1i):

[0105] 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.

[0106] 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:

[0107] 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:

[0108] Where n0 is 1 or 2 or 3 or 4.

[0109] In a particularly preferred embodiment, the luminous body E has the following structure:

[0110] Where: Y c The definition of R is as above; 21 -R 25 R is H, D, or a linear alkyl, alkoxy, thioalkoxy group having 1 to 20 C atoms, or a branched or cyclic alkyl, alkoxy, thioalkoxy group, or a silyl group having 3 to 20 C atoms, or a keto group having 1 to 20 C atoms, or an alkoxycarbonyl group having 2 to 20 C atoms, or an aryloxycarbonyl group having 4 to 20 C 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; m and n 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.

[0111] 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, or thioalkoxy group or a 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 isocyano 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.

[0112] 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.

[0113] 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.

[0114] 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).

[0115] 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.

[0116] 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.

[0117] In certain embodiments, in the composition, the luminophore E is a small molecule or a polymer.

[0118] In some embodiments, the luminophore E has good solubility in the resin or resin prepolymer.

[0119] In certain preferred embodiments, the organic compound H has good solubility in the resin or resin prepolymer.

[0120] 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.

[0121] In some preferred embodiments, the organic compound H and / or the luminophore E contain at least two alcohol-soluble or water-soluble groups.

[0122] In other preferred embodiments, the organic compound H and / or the luminophore E contain at least three alcohol-soluble or water-soluble groups.

[0123] 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.

[0124] Preferably, the alcohol-soluble or water-soluble group is selected from the following structure:

[0125] Where: R 31 -R 37 It can be a straight-chain alkyl, alkoxy, thioalkoxy group having 1 to 20 C atoms, or a branched or cyclic alkyl, alkoxy, thioalkoxy, silyl group having 3 to 20 C atoms, or a substituted keto group having 1 to 20 C atoms, or an alkoxycarbonyl group having 2 to 20 C atoms, or an aryloxycarbonyl group having 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 having 5 to 40 ring atoms, or an aryloxy or heteroaryloxy group having 5 to 40 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 group is bonded; t is an integer greater than 0.

[0126] 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 group consisting of 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 and 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.

[0127] Examples of luminophore E are given below, but are not limited thereto, and may be further substituted arbitrarily:

[0128] 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.

[0129] In some preferred embodiments, the organic compound H and / or the luminophore E contain at least two cross-linkable groups.

[0130] In some other preferred embodiments, the organic compound H and / or the luminophore E contain at least three cross-linkable groups.

[0131] In certain preferred embodiments, the organic compound H can be polymerized to form a polymer. That is, the composition 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.

[0132] In certain embodiments, the luminophore E is a polymer comprising at least one repeating structural unit represented by formula (1) or (2). 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.

[0133] 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:

[0134] Wherein: X is CR9 or N; R1-R9 are each independently selected from hydrogen, alkyl, cycloalkyl, heterocyclyl, alkenyl, cycloalkenyl, alkynyl, hydroxyl, thiol, alkoxy, alkylthio, aryl ether, aryl thioether, aryl, heteroaryl, halogen, cyano, aldehyde, carbonyl, carboxyl, oxycarboxyl, carbamoyl, amino, nitro, silyl, siloxane, borane, and phosphine oxide, and R1-R9 can form a condensed ring and an aliphatic ring with adjacent substituents.

[0135] Examples of suitable Bodipy derivatives include, but are not limited to:

[0136] In a preferred embodiment, in the organic compound H, R 101 -R 104 At least one is selected from the group consisting of chemical formulas (Ia-5) - (Ia-6):

[0137] wherein: Ar2 is as defined above; Ar3 is the same or different and is selected from an aromatic or heteroaromatic group having 8 to 24 ring atoms, which may be further substituted; Ar4 or Ar5 may be the same or different and are selected from an aromatic or heteroaromatic group having 5 to 24 ring atoms, and the chemical formula (Ia-6) contains at least one electron-withdrawing group; R 105 The definition of is the same as above; * represents the connection site with pyrene.

[0138] Preferably, in chemical formula (Ia-6), Ar4 or Ar5 contains at least one electron-withdrawing group, that is, Ar4 or Ar5 is selected from an electron-withdrawing group or is substituted by an electron-withdrawing group.

[0139] In some preferred embodiments, the organic compound H contains two electron-withdrawing groups.

[0140] In some preferred embodiments, the organic compound H contains three electron-withdrawing groups.

[0141] In other preferred embodiments, the organic compound H contains three or more electron-withdrawing groups.

[0142] The electron-withdrawing group can be selected from F, cyano or one of the following groups:

[0143] Where: n1 is 1, 2 or 3; X1-X 10 Selected from CR 60 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 N(R 60 )、C(R 60 R 70 )2、Si(R 60 R 70 )2、O、C=N(R 60 ), C=C(R 60 R 70 )2、P(R 60 ), P(=O)R 60 , S, S=O, SO2 or none; R 40 、R 50 、R 60 、R 70 The meanings of , are the same as those of R 1 .

[0144] In certain preferred embodiments, suitable electron withdrawing groups include, but are not limited to, F, Cl, cyano, partially or fully fluorinated alkyl chains, or one of the following groups:

[0145] The symbols are defined as above.

[0146] In some preferred embodiments, the organic compound H contains -F.

[0147] In some preferred embodiments, the organic compound H contains -CN.

[0148] In other preferred embodiments, the organic compound H contains the following group:

[0149] In some preferred embodiments, Ar3 in formula (Ia-5) is selected from the following groups, which may be further substituted:

[0150] The symbols are defined as above.

[0151] In some preferred embodiments, for the organic compound H, the above R 101-R 104 At least two of the same or different ones are selected from one of the chemical formulas (Ia-1) to (Ia-6).

[0152] In some preferred embodiments, for the organic compound H, the above R 101 -R 104 At least three of them are the same or different and are selected from one of the chemical formulas (Ia-1) to (Ia-6).

[0153] In some preferred embodiments, for the organic compound H, the above R 101 -R 104 The same or different ones are selected from one of the chemical formulas (Ia-1) to (Ia-6).

[0154] According to the composition 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.

[0155] In certain embodiments, the absorption spectrum of the organic compound H is between 380 nm and 500 nm.

[0156] In some preferred embodiments, the luminescence spectrum of the organic compound H is between 460 nm and 510 nm.

[0157] In a preferred embodiment, the wavelength corresponding to the peak of the luminescence spectrum of the organic compound H is less than 500 nm.

[0158] In other preferred embodiments, the luminescence spectrum of the organic compound H is between 500 nm and 580 nm.

[0159] The energy structure of organic compounds has an important influence on their photoelectric properties and stability.

[0160] In a preferred embodiment, the organic compound H has a large ΔHOMO and / or ΔLUMO, generally ≥0.30 eV, preferably ≥0.40 eV, more preferably ≥0.50 eV, even better ≥0.60 eV, and most preferably ≥0.70 eV; wherein ΔHOMO=HOMO-(HOMO-1), ΔLUMO=(LUMO+1)-LUMO.

[0161] For the purposes of this invention, (HOMO-1) is defined as the second-highest occupied molecular orbital energy level, (HOMO-2) as the third-highest occupied molecular orbital energy level, and so on. (LUMO+1) is defined as the second-lowest unoccupied molecular orbital energy level, (LUMO+2) as the third-lowest occupied molecular orbital energy level, and so on. These energy levels can be determined by the simulation method described below.

[0162] In a preferred embodiment, the organic compound H has a large resonance factor f(Sn) (n ≥ 1); generally, f(S1) ≥ 0.10, preferably ≥ 0.20, more preferably ≥ 0.30, even more preferably ≥ 0.40, particularly preferably ≥ 0.50, and most preferably ≥ 0.60. The resonance factor f(Sn) can be calculated by the following method.

[0163] In a further embodiment, f(S1) is ≥ 0.70, preferably ≥ 0.80, more preferably ≥ 0.90, even more preferably ≥ 1.00, particularly preferably ≥ 1.2, and most preferably ≥ 1.6.

[0164] In certain embodiments, the organic compound H has a relatively low HOMO, generally ≤-4.6 eV, preferably ≤-4.7 eV, more preferably ≤-4.8 eV, even more preferably ≤-4.9 eV, particularly preferably ≤-5.1 eV, and most preferably ≤-5.2 eV.

[0165] 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, more preferably ≥70 mg / mL, even more preferably ≥100 mg / mL, and most preferably ≥150 mg / mL.

[0166] Some examples of suitable organic compounds H are listed below (but are not limited to), which may be further substituted with any substitutions:

[0167] According to the composition 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)).

[0168] In certain preferred embodiments, the luminescence spectrum of the composition is completely derived from the luminophore E, that is, complete energy transfer is achieved between the luminophore E and the organic compound H.

[0169] In certain embodiments, the composition comprises two or more organic compounds H.

[0170] In certain embodiments, the organic compound H is selected from one of the chemical formulas (1)-(1e) or (2)-(2e).

[0171] In a preferred embodiment, in the composition, 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.

[0172] The present invention also relates to another composition Z2, comprising an organic compound H2, a luminophore D2 and an organic resin, characterized in that: 1) the emission spectrum of the organic compound H2 is on the short-wavelength side of the absorption spectrum of the luminophore D2, and at least partially overlaps with each other; 2) the luminophore D2 contains the structural unit represented by the above chemical formula (3) or (4).

[0173] In a preferred embodiment, in the another composition Z2, the organic compound H2 is selected from compounds having structural units represented by one of the following chemical formulas (1) to (4),

[0174] The symbols and marks used have the following meanings:

[0175] R 101 -R 104is a substituent, which may be the same or different and is selected from a linear alkyl, haloalkyl, alkoxy, thioalkoxy group having 1 to 20 C atoms, or a branched or cyclic alkyl, haloalkyl, alkoxy, thioalkoxy group, silyl group having 3 to 20 C atoms, or a substituted keto group having 1 to 20 C atoms, or an alkoxycarbonyl group having 2 to 20 C atoms, or an aryloxycarbonyl group having 7 to 20 C atoms, or a cyano, carbamoyl, halomethyl Acyl, formyl (-C(=O)-H), isocyanate, 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 arylamino or heteroarylamino group having 5 to 40 ring atoms, a disubstituted unit at any position of the above substituents, or a combination of these substituents;

[0176] u and w are independently selected from natural numbers from 1 to 10, v and x are independently selected from natural numbers from 1 to 12,

[0177] In one embodiment, the compound H2 contains at least one alcohol-soluble or water-soluble group, as disclosed in the prior Chinese patent application number PCT / CN2022 / 085363; in another embodiment, the compound H2 contains at least one cross-linkable group, as disclosed in the prior Chinese patent application number PCT / CN2022 / 085362; these two patent documents are hereby incorporated into this article for reference.

[0178] In a particularly preferred embodiment, in the aforementioned composition Z2, the luminophore D2 is selected from the group consisting of the above chemical formulae (3a), (4a), (3b), (4b), (3c), (4c), (3d), (4d1), and (4d2).

[0179] In a particularly preferred embodiment, the composition according to the invention or the further composition Z2 further comprises an organic resin and / or a solvent. For the purposes of the present invention, the organic resin is a resin prepolymer or a resin formed after crosslinking or curing.

[0180] In a particularly preferred embodiment, the composition according to the invention or the further composition Z2 further comprises an organic resin; in a preferred embodiment, the composition comprises two or more organic resins.

[0181] Organic resins suitable for the present invention include, but are not limited to, polystyrene, polyacrylate, polymethacrylate, polycarbonate, polyurethane, polyvinyl pyrrolidone, polyvinyl acetate, polyvinyl chloride, polybutylene, polyethylene glycol, polysiloxane, polyacrylate, 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.

[0182] 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.

[0183] 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.

[0184] 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 and 3-dimethylaminopropyl methacrylate; glycidyl acrylate and glycidyl methacrylate;

[0185] Examples of acrylonitrile derivatives are: acrylonitrile, methacrylonitrile, α-chloroacrylonitrile and vinylidene cyanide;

[0186] Examples of acrylamide derivatives are: acrylamide, methacrylamide, α-chloroacrylamide, N-2-hydroxyethylacrylamide and N-2-hydroxyethylmethacrylamide;

[0187] Examples of vinyl ester derivatives are: vinyl acetate, vinyl propionate, vinyl butyrate, and vinyl benzoate;

[0188] Examples of vinyl ether derivatives are vinyl methyl ether, vinyl ethyl ether and allyl glycidyl ether;

[0189] Examples of maleimide derivatives are maleimide, benzylmaleimide, N-phenylmaleimide and N-cyclohexylmaleimide;

[0190] Examples of conjugated diene derivatives are: 1,3-butadiene, isoprene, and chloroprene;

[0191] 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.

[0192] The organic resins generally have an average molar mass Mn (determined by GPC) of 10,000 to 1,000,000 g / mol, preferably 20,000 to 750,000 g / mol, more preferably 30,000 to 500,000 g / mol.

[0193] 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.

[0194] 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.

[0195] 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).

[0196] 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)).

[0197] In some embodiments, a thermal initiator is used. In some embodiments, the thermal initiator is AIBN [2,2'-azobis(2-methylpropionitrile)] or benzoyl peroxide.

[0198] 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.

[0199] 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.

[0200] 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.

[0201] In some embodiments, the UV curable resin further comprises a photoinitiator. The photoinitiator will initiate a crosslinking and / or curing reaction of the photosensitive material during exposure to light. In some embodiments, the photoinitiator is acetophenone-based, benzoin-based, or thioxanthone-based.

[0202] 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.

[0203] In some embodiments, the photoinitiator is MINS-311RM (Minuta Technology Co., Ltd (Korea)).

[0204] 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).

[0205] In some embodiments, the organic resin is present in an amount by weight of the composition (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%, From about 70% to about 85%, from about 70% to about 80%, from about 80% to about 99%, from about 80% to about 95%, from about 80% to about 90%, from about 80% to about 85%, from about 85% to about 99%, from about 85% to about 95%, from about 85% to about 90%, from about 90% to about 99%, from about 90% to about 95%, or from about 95% to about 99%.

[0206] The present invention also relates to a composition or another composition Z2 comprising at least one solvent. In a preferred embodiment, the composition according to the invention is a solution.

[0207] In another preferred embodiment, the composition according to the invention or the further composition Z2 is a suspension.

[0208] 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 30 wt %, more preferably 0.2 wt % to 20 wt %, and most preferably 2 wt % to 15 wt % of the luminophore E.

[0209] Another composition Z2 in an embodiment of the present invention may include 0.01 wt% to 20 wt% of the luminophore D2, preferably 0.1 wt% to 30 wt%, more preferably 0.2 wt% to 20 wt%, and most preferably 2 wt% to 15 wt% of the luminophore D2.

[0210] The color conversion layer can be formed using inkjet printing, transfer printing, photolithography, or other methods using the composition of the present invention or another composition Z2. 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 an organic solvent to form an ink. The mass concentration of the organic compound H (i.e., the color conversion material) in the ink is no 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.

[0211] 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.

[0212] In other embodiments, suitable and preferred solvents are aliphatic, cycloaliphatic or aromatic hydrocarbons, amines, thiols, amides, nitriles, esters, ethers, polyethers, alcohols, diols or polyols.

[0213] In other embodiments, alcohols represent a suitable class of solvents. Preferred alcohols include alkylcyclohexanols, particularly methylated aliphatic alcohols, naphthols, and the like.

[0214] 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.

[0215] The solvent can be used alone or as a combination of two or more organic solvents.

[0216] 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.

[0217] In some preferred embodiments, according to a composition or another composition Z2 of the present invention, the solvent is selected from aromatic or heteroaromatic, 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.

[0218] 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.

[0219] In other embodiments, suitable and preferred solvents are aliphatic, alicyclic or aromatic hydrocarbons, amines, thiols, amides, nitriles, esters, ethers, polyethers.

[0220] The solvent may be a cycloalkane, such as decalin.

[0221] In other preferred embodiments, a composition or another composition Z2 according to the present invention contains at least 50 wt% of an alcohol solvent; preferably at least 80 wt% of an alcohol solvent; particularly preferably at least 90 wt% of an alcohol solvent.

[0222] In some preferred embodiments, the solvents particularly suitable for the present invention are solvents having a Hansen solubility parameter within the following ranges:

[0223] δ d (Dispersion force) 17.0-23.2MPa 1 / 2 range, especially in the range of 18.5-21.0MPa 1 / 2 scope;

[0224] δ p (Polar force) 0.2-12.5MPa 1 / 2 range, especially in the range of 2.0-6.0MPa 1 / 2 scope;

[0225] δ h (Hydrogen bond force) 0.9-14.2MPa 1 / 2 range, especially in the range of 2.0-6.0MPa 1 / 2 range.

[0226] 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.

[0227] In some preferred embodiments, the compositions according to the present invention:

[0228] 1) Its viscosity @25°C is in the range of 1 cPs to 100 cPs, and / or

[0229] 2) Its surface tension @25℃ is in the range of 19 dyne / cm to 50 dyne / cm.

[0230] In the composition of the present invention, the surface tension parameters of the resin (prepolymer) or organic 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 organic 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.

[0231] In a preferred embodiment, the surface tension of the composition according to the present invention or another composition Z2 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.

[0232] According to the composition of the present invention or another composition Z2, the resin (prepolymer) or solvent must be selected taking into account the viscosity parameters of the ink. 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 to 20 cps. The viscosity here refers to the viscosity at the ambient temperature during printing, generally 15-30°C, preferably 18-28°C, more preferably 20-25°C, and most preferably 23-25°C. The composition thus formulated will be particularly suitable for inkjet printing.

[0233] In a preferred embodiment, the viscosity of the composition according to the present invention or another composition Z2 at 25°C is 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.

[0234] The ink obtained from the resin (prepolymer) or organic 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.

[0235] The present invention further relates to an organic functional material film, which comprises a composition as described above, or is prepared using a composition as described above.

[0236] The present invention also provides a method for preparing the organic functional material thin film, comprising the following steps:

[0237] 1) Prepare a composition according to the invention.

[0238] 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.

[0239] 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.

[0240] The thickness of the organic functional material film is generally 50nm-100μm, preferably 100nm-50μm, more preferably 300nm-30μm, even more preferably 300nm-10μm, and most preferably 300nm-10μm.

[0241] The present invention also provides applications of the composition and the organic functional material film in optoelectronic devices.

[0242] 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.

[0243] Furthermore, the present invention provides a photoelectric device comprising the above-mentioned composition or organic functional material film.

[0244] 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), and an encapsulation layer (TFE).

[0245] 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.

[0246] 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 the above-mentioned composition or organic functional material film.

[0247] 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.

[0248] 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 (OLED), a perovskite light-emitting diode (PeLED), a quantum dot light-emitting diode (QD-LED), and a nanorod LED (see DOI: 10.1038 / srep28312).

[0249] 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.

[0250] 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.

[0251] 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.

[0252] 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 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 composition 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.

[0253] The organic light-emitting device may further include a substrate, which may be located below the first electrode or above the second electrode.

[0254] The organic compound H and the luminophore E and their preferred embodiments are as described above.

[0255] 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.

[0256] 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.

[0257] In some embodiments, the thickness of the color conversion layer is between 100 nm and 2 μm, preferably between 150 nm and 10 μm, more preferably between 200 nm and 8 μm, most preferably between 200 nm and 6 μm, and most preferably between 200 nm and 4 μm.

[0258] 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.

[0259] 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).

[0260] 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 devices according to the present invention.

[0261] The cathode may comprise a conductive metal or metal oxide. The cathode can readily inject electrons into the EIL or ETL or directly into the light-emitting layer. In a preferred embodiment, the absolute value of the 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) or 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 for OLEDs may be used as cathode materials for the devices 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 may 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.

[0262] 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.

[0263] Furthermore, the electroluminescent device may further include a cathode capping layer (CPL for short).

[0264] In a preferred embodiment, the CPL is located between the second electrode and the color conversion layer.

[0265] In another preferred embodiment, the CPL is located above the color conversion layer.

[0266] 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:

[0267] More examples of further CPL materials can be found in the following patent documents: KR20140128653A, KR20140137231A, KR20140142021A, KR20140142923A, KR20140143618A, KR20140145370A, KR20150004099A, KR20150012835A, US9496520B2, US2015069350A1, CN103828485B, CN104380842B, CN1 05576143A, TW201506128A, CN103996794A, CN103996795A, CN104744450A, CN104752619A, CN101944570A, US2016308162A1, US9095033B2, US2014034942A1, WO2017014357A1; the above patent documents are hereby incorporated into this article for reference.

[0268] 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%.

[0269] Preferably, in the above-mentioned organic light-emitting device, the encapsulation layer is a thin film encapsulation (TFE).

[0270] The present invention further relates to a display panel, wherein at least one pixel comprises the above-mentioned organic light-emitting device.

[0271] The organic light-emitting device can 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 preferred. Organic electroluminescent devices, such as OLED, OLEEC, and organic light-emitting field-effect transistor.

[0272] 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.

[0273] Specific embodiments

[0274] Example 1: Compound and polymer synthesis example

[0275] 1. Synthesis of Compound 1

[0276] N-phenyl-2-benzidine (73.00 g, 297.23 mmol), 1,3,6,8-tetrabromopyrene (34.2 g, 66.05 mmol), Pd-132 (0.94 g, 1.32 mmol), X-Phos (0.94 g), sodium tert-butoxide (25.36 g, 264.19 mmol), and 1.2 L of xylene were added to a 2000 mL dry, clean three-necked flask. After three cycles of vacuum and nitrogen filling, the mixture was heated to 140°C and refluxed for 12 hours. After the reaction, the mixture was cooled to room temperature and filtered. The filtrate was concentrated. The product was dissolved in hot toluene and passed through an insulated silica gel column while hot. The filtrate was collected and concentrated to obtain 16.7 g of solid powder. The filter cake was cleared with dichloromethane and extracted three times with saturated brine, then concentrated. The organic phases were combined to obtain 35 g of crude product, which was recrystallized from 3 L of xylene to obtain 23 g of solid powder compound 1, with a yield of 29.8%.

[0277] 2. Synthesis of Compound 2

[0278] Iodobenzene (50.00 g, 245.1 mmol), 2,6-dimethylaniline (29.68 g, 245.1 mmol), palladium acetate (0.56 g, 2.45 mmol), tri-tert-butylphosphine (1 mL), 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, 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 dark brown solid intermediate 2a in a 93.7% yield.

[0279] Intermediate 2a (39.00 g, 197.3 mmol), 1,3,6,8-tetrabromopyrene (22.7 g, 48.3 mmol), Pd-132 (0.62 g, 0.97 mmol), X-Phos (0.62 g), 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 vacuum 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 2, with a yield of 2.1%.

[0280] 3. Synthesis of Compound 3

[0281] 2,6-Dimethylaniline (50.00 g, 413.2 mmol), 2,6-dimethylbromobenzene (76 g, 413.2 mmol), palladium acetate (0.46 g, 2.05 mmol), tri-tert-butylphosphine (1 mL), sodium tert-butoxide (79.3 g, 826.04 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, then heated to 100°C and refluxed for 2.5 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 88 g of solid intermediate 3a in a yield of 94.6%.

[0282] Intermediate 3a (48.9 g, 217.33 mmol), 1,3,6,8-tetrabromopyrene (25 g, 48.3 mmol), Pd-132 (1.67 g, 2.35 mmol), tri-tert-butylphosphine tetrafluoroborate (1.67 g), sodium tert-butoxide (18.54 g, 193.13 mmol), and 1 L of xylene were added to a 2000 mL dry, clean three-necked flask. After three cycles of vacuum 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 collected, concentrated, and slurried with n-hexane. The mixture was filtered with suction, and the filter cake was rinsed with n-hexane to obtain 5 g of solid powder compound 3 with a yield of 9.5%.

[0283] 4. Synthesis of Compound 4

[0284] 2,6-Dimethylaniline (50.00 g, 413.2 mmol), 4-tert-butylbromobenzene (88.00 g, 413.2 mmol), palladium acetate (0.46 g, 2.05 mmol), tri-tert-butylphosphine (1 mL), sodium tert-butoxide (59.5 g, 619.83 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, then heated to 100°C and refluxed for 2.5 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 93 g of solid intermediate 4a in an 89.4% yield.

[0285] Intermediate 4a (43.97 g, 173.79 mmol), 1,3,6,8-tetrabromopyrene (20 g, 38.62 mmol), Pd-132 (0.82 g, 1.16 mmol), S-Phos (0.82 g), sodium tert-butoxide (14.83 g, 154.48 mmol), and 1 L of xylene were added to a 2000 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 still hot. The filtrate was collected and concentrated to obtain 25 g of crude product, which was recrystallized from xylene to obtain 20 g of solid powdered compound 4 in a yield of 42.8%.

[0286] 5. Synthesis of Compound 5

[0287] 4-tert-Butylaniline (23.94 g, 159.6 mmol), 4-tert-butylbromobenzene (34.00 g, 159.6 mmol), palladium acetate (0.18 g, 0.8 mmol), tri-tert-butylphosphine (0.5 mL), sodium tert-butoxide (22.98 g, 239.4 mmol), and 500 mL of toluene were added to a 1000 mL, clean, dry three-necked flask. The mixture was evacuated and filled with nitrogen three times, then heated to 100°C and refluxed for 2.5 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 12 g of solid intermediate 5a in a yield of 27.1%.

[0288] Intermediate 5a (10 g, 35.59 mmol), 1,3,6,8-tetrabromopyrene (4 g, 7.72 mmol), Pd-132 (0.27 g, 0.38 mmol), S-Phos (0.27 g, equal to the catalyst), sodium tert-butoxide (3 g, 31.25 mmol), and 100 mL of xylene were added to a 250 mL dry, clean three-necked flask. After three cycles of vacuum 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 xylene and passed through an insulated silica gel column while hot. The filtrate was concentrated to obtain 4 g of solid powder compound 5 with a yield of 39.2%.

[0289] 6. Synthesis of Compound 6

[0290] 2,6-Dimethylaniline (14.85 g, 122.73 mmol), 6a-1 (50.00 g, 128.87 mmol), palladium acetate (0.28 g, 1.25 mmol), X-Phos (0.28 g), cesium carbonate (59.98 g, 184.09 mmol), and 500 mL of toluene were added to a 1000 mL, clean, dry three-necked flask. The mixture was evacuated and filled with nitrogen three times, then heated to 100°C and refluxed for 3.5 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 18 g of solid intermediate 6a in a yield of 40.9%.

[0291] Intermediate 6a (18 g, 50.14 mmol), 1,3,6,8-tetrabromopyrene (5.77 g, 11.14 mmol), Pd-132 (0.16 g, 0.23 mmol), S-Phos (0.16 g), sodium tert-butoxide (4.28 g, 44.58 mmol), and 250 mL of xylene were added to a 500 mL dry, clean three-necked flask. After three cycles of vacuum and nitrogen filling, the mixture was heated to 140°C and refluxed for 14 hours. After the reaction was completed, the mixture was cooled to room temperature and extracted three times with dichloromethane and saturated brine. The organic phases were combined and concentrated to obtain a crude product, which was separated and purified by silica gel column chromatography (eluent: dichloromethane: petroleum ether = 1:20) to obtain 1.8 g of solid powder compound 6 in a yield of 9.9%.

[0292] 7. Synthesis of Compound 7

[0293] 2,6-Dimethylaniline (21 g, 173.55 mmol), 3,5-di-tert-butylbromobenzene (47.00 g, 174.72 mmol), palladium acetate (0.19 g, 0.85 mmol), tri-tert-butylphosphine (1 mL), sodium tert-butoxide (24.09 g, 250.09 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, then heated to 100°C and refluxed for 12 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 48 g of intermediate 7a as an oil with a yield of 89.72%.

[0294] Intermediate 7a (53 g, 171.52 mmol), 1,3,6,8-tetrabromopyrene (19.74 g, 38.12 mmol), Pd-132 (0.54 g, 0.76 mmol), S-Phos (0.54 g), sodium tert-butoxide (14.64 g, 152.49 mmol), and 1 L of xylene were added to a 2000 mL dry, clean three-necked flask. After three cycles of vacuum and nitrogen filling, the mixture was heated to 140°C and refluxed for 14 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 collected and concentrated to obtain 30 g of crude product. The crude product was recrystallized from tetrahydrofuran to obtain 22.5 g of solid powder compound 7 with a yield of 41.3%.

[0295] 8. Synthesis of Compound 8

[0296] 2,6-Diisopropylaniline (24.9 g, 140.68 mmol), 4-tert-butylbromobenzene (30.00 g, 140.85 mmol), palladium acetate (0.16 g, 0.71 mmol), tri-tert-butylphosphine (1 mL), sodium tert-butoxide (20.3 g, 211.46 mmol), and 500 mL of toluene were added to a 1000 mL, clean, dry three-necked flask. The mixture was evacuated and filled with nitrogen three times, then heated to 100°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 passed through a short silica gel column (eluent: dichloromethane:n-hexane = 1:10). The product was collected and concentrated to obtain 38 g of intermediate 8a as an oil in an 86.9% yield.

[0297] Intermediate 8a (38 g, 122.98 mmol), 1,3,6,8-tetrabromopyrene (14.15 g, 27.33 mmol), Pd-132 (0.39 g, 0.55 mmol), S-Phos (0.39 g), sodium tert-butoxide (10.49 g, 109.27 mmol), and 1 L of xylene were added to a 2000 mL, dry, clean three-necked flask. After three cycles of evacuation and nitrogen filling, the mixture was heated to 140°C and refluxed for 14 hours. After the reaction was completed, the mixture was cooled to room temperature and extracted three times with dichloromethane and saturated brine. The organic phases were combined, concentrated, and purified by silica gel column chromatography (eluent: dichloromethane: petroleum ether = 1:20) to obtain 3.9 g of solid powder compound 8 in a 10% yield.

[0298] 9. Synthesis of Compound 9

[0299] 2,6-Diisopropylaniline (40 g, 225.99 mmol), 3,5-di-tert-butylbromobenzene (60.79 g, 226.82 mmol), palladium acetate (0.25 g, 1.11 mmol), tri-tert-butylphosphine (1.5 mL), sodium tert-butoxide (32.5 g, 338.54 mmol), and 500 mL of toluene were added to a 1000 mL, clean, dry three-necked flask. The mixture was evacuated and filled with nitrogen three times, then heated to 100°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 passed through a short silica gel column (eluent: dichloromethane:n-hexane = 1:10). The product was collected and concentrated to obtain 76 g of solid intermediate 9a in a 92.1% yield.

[0300] Intermediate 9a (76 g, 208.22 mmol), 1,3,6,8-tetrabromopyrene (23.96 g, 46.27 mmol), Pd-132 (0.66 g, 0.93 mmol), S-Phos (0.66 g), sodium tert-butoxide (17.77 g, 185.10 mmol), and 1 L of xylene were added to a 2000 mL dry, clean three-necked flask. After three cycles of vacuum and nitrogen filling, the mixture was heated to 140°C and refluxed for 14 hours. After the reaction was completed, the mixture was cooled to room temperature, dichloromethane was added, and saturated brine was extracted three times. The organic phases were combined, concentrated, and purified by silica gel column chromatography (eluent: dichloromethane: petroleum ether = 1:20) to obtain 7 g of solid powder compound 9 in a yield of 9.1%.

[0301] 10. Synthesis of Compound 10

[0302] 2,6-Diethylaniline (24.9 g, 167.11 mmol), 3,5-di-tert-butylbromobenzene (43 g, 160.45 mmol), palladium acetate (0.19 g, 0.85 mmol), tri-tert-butylphosphine (1 mL), sodium tert-butoxide (24 g, 250.0 mmol), and 500 mL of toluene were added to a 1000 mL, clean, dry three-necked flask. The mixture was evacuated and filled with nitrogen three times, then heated to 100°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 combined organic phases were concentrated and passed through a short silica gel column (eluent: dichloromethane:n-hexane = 1:10). The product was collected and concentrated to obtain 52 g of intermediate 10a as an oil, with a yield of 96.3%.

[0303] Intermediate 10a (52 g, 154.30 mmol), 1,3,6,8-tetrabromopyrene (17.76 g, 34.30 mmol), Pd-132 (0.49 g, 0.69 mmol), S-Phos (0.49 g), sodium tert-butoxide (13.17 g, 137.19 mmol), and 1 L of xylene were added to a 2000 mL dry, clean three-necked flask. The mixture was evacuated and filled with nitrogen for three cycles, and then heated to 140°C and refluxed for 14 hours. After the reaction was completed, the mixture was cooled to room temperature and extracted three times with dichloromethane and saturated brine. The organic phases were combined and concentrated. The product was dissolved in hot toluene and passed through an insulated silica gel column while still hot. The filtrate was collected and concentrated to obtain 15 g of crude product. The crude product was recrystallized from tetrahydrofuran to obtain 9.6 g of solid powder compound 10, with a yield of 18.5%.

[0304] 11. Synthesis of Compound 11

[0305] 2,6-Diethylaniline (34.98 g, 234.74 mmol), 4-tert-butylbromobenzene (50 g, 234.74 mmol), palladium acetate (0.26 g, 1.16 mmol), tri-tert-butylphosphine (1.5 mL), sodium tert-butoxide (33.8 g, 352.08 mmol), and 500 mL of toluene were added to a 1000 mL, clean, dry three-necked flask. The mixture was evacuated and filled with nitrogen three times, then heated to 100°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 combined organic phases were concentrated and passed through a short silica gel column (eluent: dichloromethane:n-hexane = 1:10). The product was collected and dried to obtain 60 g of intermediate 11a as an oil in a 90.9% yield.

[0306] Intermediate 11a (70 g, 249.11 mmol), 1,3,6,8-tetrabromopyrene (30 g, 57.92 mmol), Pd-132 (0.81 g, 1.14 mmol), S-Phos (0.81 g), sodium tert-butoxide (21.86 g, 227.71 mmol), and 1 L of xylene were added to a 2000 mL, dry, clean three-necked flask. After three cycles of evacuation and nitrogen filling, the mixture was heated to 140°C and refluxed for 14 hours. After the reaction was completed, the mixture was cooled to room temperature and extracted three times with dichloromethane and saturated brine. The product was dissolved in hot toluene and passed through an insulated silica gel column while still hot. The filtrate was collected and concentrated to obtain 10 g of crude product, which was recrystallized from tetrahydrofuran to obtain 4 g of solid powdered compound 11 in a 5.2% yield.

[0307] Other ingredients:

[0308] The synthesis of compounds 12-26 is similar to that of compounds 1-11. The synthesis of comparative example 1 is based on PCT patent (International Publication No. WO2022213993A1), and the synthesis of comparative example 2 is based on US20150069350A1.

[0309] 12. Synthesis of polymer P1, where x:y = 1:10

[0310] 1-Nitropyrene (10 g, 40.44 mmol) and 500 mL of DCM were added to a 1000 mL dry, clean three-necked flask. Liquid bromine (9.69 g, 121.3 mmol) was added in the dark. The mixture was evacuated and nitrogen was filled for three cycles. The reaction was allowed to proceed in the dark for 12 hours. The mixture was extracted three times with dichloromethane and saturated brine. The solvent was removed by rotary evaporation and the reaction was recrystallized from toluene to obtain 15 g of solid powder to obtain intermediate P1a with a yield of 76.2%.

[0311] Intermediate P1a (15 g, 31.05 mmol), 11a (41.55 g, 139.73 mmol), Pd(OAc)2 (2.325 mmol), PtBu3 (3.105 mmol), NaOtBu (26.85 g, 279.45 mmol), and 1 L of toluene were added to a 2000 mL, dry, clean three-necked flask. After three cycles of evacuation and nitrogen refilling, the mixture was heated to 120°C and refluxed for 24 hours. After the reaction was completed, the mixture was cooled to room temperature and extracted three times with dichloromethane and saturated brine. The combined organic phases were concentrated and passed through a short silica gel column (eluent: ethyl acetate:n-hexane = 1:20). The product was collected and dried to obtain 24 g of intermediate P1b in a 71.2% yield.

[0312] Intermediate P1b (24 g, 22.11 mmol), SnCl2 (20.89 g, 110.54 mmol), and 1.5 L of anhydrous ethanol were added to a 2000 mL dry, clean three-necked flask. After three cycles of vacuum and nitrogen filling, the mixture was heated to 70°C for 1 hour. The mixture was poured into ice water and slightly alkaline with the addition of sodium bicarbonate solution. The precipitate was filtered and vacuum-dried, then dissolved in 500 mL of anhydrous ethanol and cooled to -5°C. 200 mL of a solution of NaNO2 (2.42 g, 28.4 mmol) in H2SO4 was slowly added with stirring. A mixture of CuI (0.54 g, 2.84 mmol) and I2 (3.6 g, 28.4 mmol) was slowly added in batches. The mixture was filtered, and the product was collected and spin-dried to obtain 5 g of intermediate P1c with a yield of 19.4%.

[0313] Intermediate P1c (5 g, 4.25 mmol), intermediate P1d (2.1 g, 6.5 mmol), Pd(OAc)2 (0.075 g), PtBu3 (0.1 g), NaOtBu (1.25 g, 12.75 mmol), and 500 mL of toluene were added to a 1000 mL, dry, clean three-necked flask. After three cycles of evacuation and nitrogen refilling, the mixture was heated to 120°C and refluxed for 24 hours. After the reaction, the mixture was cooled to room temperature and extracted three times with dichloromethane and saturated brine. The combined organic phases were concentrated and passed through a short silica gel column (eluent: ethyl acetate:n-hexane = 1:20). The product was collected and dried to obtain 3.5 g of intermediate P1e, with a yield of 61.2%.

[0314] Intermediate P1e (3.5 g, 2.6 mmol), styrene (2.70 g, 26 mmol), BPO (0.0624 g, 0.26 mmol), and 100 mL of DCM were added to a clean, dry 250 mL three-necked flask. The mixture was evacuated and filled with nitrogen three times, then stirred and irradiated with UV light for 12 hours. After completion of the reaction, the monomers were removed by dialysis and dried to yield 1.56 g of polymer (P1) in a 25.1% yield.

[0315] The structures of E1, E2 and E3 as green light guests are as follows, where E1 was purchased from Shanghai McLean Biochemical Technology Co., Ltd., the synthesis of E2 can be found in the prior patent application with application number CN202211429395.8, and the synthesis of E3 can be found in the prior patent application with application number PCT / CN2023 / 131804.

[0316] The structure of E4 as a red light guest is as follows, where the synthesis of E4 can be found in the literature Chuluo Yang, et.al., Adv. Mater., 2022, 2201442.

[0317] Example 2: Energy level structure of the compound

[0318] The energy levels of organic materials can be calculated through quantum calculations, such as using TD-DFT (time-dependent density functional theory) with Gaussian09W (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.

[0319] HOMO(eV)=((HOMO(G)×27.212)-0.9899) / 1.1206

[0320] LUMO(eV)=((LUMO(G)×27.212)-2.0041) / 1.385

[0321] The HOMO (G) and LUMO (G) are directly calculated using Gaussian 09W, with units in Hartree. The results are shown in Table 1 below.

[0322] Table 1

[0323] Example 3: Solubility of Compounds

[0324] The solubility of the compound in toluene was determined as follows:

[0325] 1. Place 1000 mg of toluene solution in a clear glass sample bottle.

[0326] 2. Weigh a certain amount of compound and dissolve it in toluene. Shake and let it stand until it is completely dissolved.

[0327] 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.

[0328] 4. Repeat the above steps until a precipitate appears and the compound no longer dissolves.

[0329] 5. Record the total mass of compound added and calculate the solubility.

[0330] The solubility of compounds 1-26 and E1-E4 in toluene is shown in Table 2 below.

[0331] Table 2

[0332] Example 4: Abs / UV and extinction coefficient of the compound (comparison of solution and film)

[0333] The extinction coefficient of the compound and its Abs / UV spectrum in solution were determined as follows:

[0334] 1. Use a volumetric flask to prepare a toluene solution of the compound with a certain molar concentration.

[0335] 2. Use a UV-visible spectrophotometer (Puxi T9s) to measure the absorption spectrum of the solution and obtain the absorption peak position.

[0336] 3. The absorbance of the maximum absorption peak divided by the equivalent concentration of the solution substance is the molar extinction coefficient of the compound.

[0337] 4. The emission spectrum of the solution was measured using a fluorescence spectrometer (Hitachi, F-4700 FL Spectrophotometer) to obtain the emission peak position.

[0338] The Abs / UV spectrum of the compound in the film was measured by the following method:

[0339] 1. Prepare a toluene solution of the compound with a certain concentration.

[0340] 2. Apply the prepared toluene solution on a clean glass substrate.

[0341] 3. Spin coating and baking at 80℃ for 1 min to obtain a compound film.

[0342] 4. Use a UV-visible spectrophotometer (Puxi T9s) to measure the absorption spectrum of the film and obtain the absorption peak position.

[0343] 5. The emission spectrum of the film was measured using a fluorescence spectrometer (Hitachi, F-4700 FL Spectrophotometer) to obtain the emission peak position.

[0344] The extinction coefficients of the compounds and their absorption and emission peaks in solution and film are shown in Table 3.

[0345] Table 3

[0346] Table 3 above shows that the tested organic compounds H according to the present invention all have relatively high molar extinction coefficients.

[0347] Figures 2-33 show the absorption and emission spectra of toluene solutions and films of compounds 1, 2, 4, 6, 7, 10, 11, 16, 17, 20, 21, 22, 23, 24, 25, and 26. As can be seen from these figures, the absorption and emission spectra of compound 1 according to chemical formula (1a-1) and compounds 2, 4, 6, 7, 10, 11, 22, 23, 24, 25, and 26 according to chemical formula (1a-3) in solution and film are very similar, and the red shift of the spectrum in the film is very small. This is because the ortho-substitution on the aromatic group (here, benzene) in the aromatic amine effectively prevents the accumulation of molecules in the film. Similarly, the compounds according to chemical formulas (1a-2), (1a-4), (1a-5), and (1a-6) also have the same properties.

[0348] On the other hand, the spectra of compounds 16, 17, 20, and 21 in thin films exhibit significant red-shifts relative to their solution spectra, and their emission lines broaden due to molecular stacking effects in the films. Nevertheless, by combining compounds 16, 17, 20, and 21 with other compounds or polymers to form mixtures, they can potentially avoid stacking and maintain spectra similar to those in solution, making them suitable for use in color conversion layers.

[0349] As described above (Example 4), the optical properties of the compounds: absorption and fluorescence spectra were measured by a spectrophotometer (Puxi T9s) and a fluorescence spectrometer (Hitachi, F-4700 FL Spectrophotometer), respectively. Figure 34 shows the absorption and emission spectra of the toluene solution of compound E1; Figure 35 shows the absorption and emission spectra of the toluene solution of compound E2; Figure 36 shows the absorption and emission spectra of the toluene solution of E3; Figure 37 shows the absorption and emission spectra of the toluene solution of E4; Figures 38 and 39 show the absorption and emission spectra of the toluene solution and film of Comparative Example 1, respectively. The emission spectrum of the film of Comparative Example 1 undergoes a large red shift. Although it can still be used as a green or red light host, it may affect the color purity of the green light. In contrast, the red shift of the film spectra of compounds 2, 4, 6, 7, 10, 11, 22, 23, 24, 25, and 26 is very small, which is more conducive to the preparation of CCL with high color purity.

[0350] Example 5: Optical properties and UV stability of compounds

[0351] The test method for the UV stability of the compound is as follows:

[0352] Prepare 1×10 -5Take 3 mL of a mol / L toluene solution 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 12 cm away from the UV LED (365 nm & 255 nm). Irradiate for a period of time and take out the test absorption spectrum. After the test, continue irradiation. Repeat this process until the absorbance decays to 80% of the original value. Record the time and record it as t80.

[0353] The t80 of each compound is shown in Table 4 below:

[0354] Table 4

[0355] Figure 40 shows the absorption attenuation graphs of toluene solutions of Compounds 1, 2, 4, 6, 7, 10, 11, 16, 17, 20, 22, 23, 24, and 26 and Comparative Example 2 after UV irradiation. Table 4 and Figure 40 show that: 1) the photostability of organic compound H according to the present invention is significantly improved compared to Comparative Example 2; and 2) among the structurally similar compounds 16, 17, and 20, the stability of the fluorinated compounds 16 and 17 is also significantly improved compared to the non-fluorinated compound 20.

[0356] Example 6: Blue Light Stability of Compound Films

[0357] The test method for the blue light stability of the films of Compound 10 and Comparative Example 1 is as follows:

[0358] Evaporate a compound film of about 800nm, seal it with a glass cover, and place it on a blue light LED (460nm, 3000cd / m 2 The brightness was measured 2.5 cm above the film using a luminance meter (Foshida, CS-2000A). The brightness of the first test was recorded as the initial value. The brightness was then measured over a period of time to obtain a brightness decay curve, as shown in Figure 41. As can be seen from Figure 41, the photostability of the film of Compound 10 was significantly improved compared to that of Comparative Example 1.

[0359] Example 7: Preparation of Color Conversion Film (CCL)

[0360] 7.1 Evaporation film: Compound 10 and luminescent material E1 or E2 or E3 are placed in crucibles respectively. The crucibles are placed in a thermal evaporation device and vacuumed to a vacuum degree of 1×10 -4 Pa, start heating the crucible to evaporate the two organic compounds onto the glass substrate. Stop heating after reaching the target thickness. Wait until it cools to 80°C, fill the thermal evaporation equipment with nitrogen to reach atmospheric pressure, and then open the cavity to obtain the evaporated CCL film.

[0361] 7.2 Solution-processed film: Take 48 mg of compound 10 and dissolve it in 1 mL of toluene solution, stir for 30 min, take 2 mg of luminescent material E1 or E2 or E3 and dissolve it in the solution, continue stirring for 30 min, take the stirred solution and drop it on the glass substrate, spin coat, and heat at 80°C for 5 min to obtain the CCL film.

[0362] 7.3 Resin film: Dissolve 48 mg of compound 10 in 1 mL of resin solution and stir for 30 min. Dissolve 2 mg of luminescent material E1, E2, or E3 in the solution and continue stirring for 30 min. Drop the stirred solution onto a glass substrate, spin coat, and cure with UV light to obtain a CCL film.

[0363] CCLs based on other organic compounds can be prepared in the same manner according to 7.1, 7.2 or 7.3.

[0364] Example 8: Results of OLED or LED+CCL film

[0365] 1. Top-emitting blue OLED + resin CCL: On the light-emitting surface of the top-emitting blue OLED, prepare a CCL resin film (E3 and E4 as light-emitting bodies) according to the above 7.3, with a thickness of about 4μm.

[0366] 2. Bottom-emitting blue OLED + resin CCL: On the light-emitting surface of the bottom-emitting blue OLED, prepare a CCL resin film (E3 as the light-emitting body) according to the above 7.3, with a thickness of about 4μm.

[0367] 3. Using a luminance meter (Foshida, CS-2000A), the spectra of a top-emitting blue OLED, a top-emitting blue OLED + resin CCL, a bottom-emitting blue OLED, and a bottom-emitting blue OLED + resin CCL were measured. Figure 42 shows a top-emitting blue OLED + resin CCL (E3 as the luminescent element); Figure 43 shows a bottom-emitting blue OLED + resin CCL (E3 as the luminescent element); and Figure 44 shows a top-emitting blue OLED + resin CCL (E4 as the luminescent element). As shown in Figures 42 and 43, the resin CCL according to the present invention can essentially absorb all of the blue light from the OLED in both top-emitting and bottom-emitting devices and convert it into a narrow spectrum of green light. As shown in Figure 44, the resin CCL according to the present invention can essentially absorb all of the blue light from the OLED in a top-emitting device and convert it into a narrow spectrum of red light.

[0368] Example 9: OLED with CCL (top OLED + vapor-deposited CCL)

[0369] 1. Top-emitting blue OLED + evaporated CCL: On the light-emitting surface of the top-emitting blue OLED, prepare a CCL evaporated film (E2 as the luminescent material) according to 7.1 above, with a thickness of 500nm.

[0370] 2. A luminance meter (Foster, CS-2000A) was used to test a top-emitting blue OLED and a top-emitting blue OLED with an evaporated CCL. Figure 45 shows that a top-emitting blue OLED with an evaporated CCL can produce a narrow green emission spectrum through the CCL film. However, due to the thin CCL film, blue light still transmits. Increasing the CCL film thickness can eliminate this problem.

[0371] 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.

[0372] 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 composition comprising an organic compound H represented by chemical formula (I) and a luminophore E, characterized in that: 1) The luminescence 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 each other; 2) The half-peak width of the luminescence spectrum of the luminophore E is less than or equal to 55 nm; Where: R 101 -R 104 is selected from H, D, which may be identical or different on each occurrence, or a linear alkyl, alkenyl, haloalkyl, alkoxy, thioalkoxy radical having 1 to 20 C atoms, or a branched or cyclic alkyl, haloalkyl, alkoxy, thioalkoxy radical, 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 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 arylamino or heteroarylamino group having 5 to 40 ring atoms, a disubstituted unit at any position of the above groups, or a combination of these groups; It is characterized by 101 -R 104 At least one of them is selected from chemical formula (Ia), wherein Ar1 and Ar2 are the same or different and are selected from substituted or unsubstituted aromatic or heteroaromatic groups having 5 to 24 ring atoms, and * represents the connection site with pyrene.

2. The composition according to claim 1, characterized in that R 101 -R 104 At least one of the compounds is selected from the group consisting of: in: *, Ar1 and Ar2 are as defined in claim 1; R 105 -R 108 is a substituent which, on each occurrence, may be identical or different and is selected from a linear alkyl, haloalkyl, alkoxy, thioalkoxy group having 1 to 20 C atoms, or a branched or cyclic alkyl, haloalkyl, alkoxy, thioalkoxy group, a silyl group having 3 to 20 C atoms, or a keto group having 1 to 20 C atoms, or an alkoxycarbonyl group having 2 to 20 C atoms, or an aryloxycarbonyl group having 4 to 20 C atoms, or a cyano group, a carbamoyl, a haloformyl, a formyl group, an isocyanate, an isocyanate, a thiocyanate, an isothiocyanate, a hydroxyl group, a nitro group, 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 arylamino or heteroarylamino group having 5 to 40 ring atoms, or a combination thereof.

3. The composition 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 selected from aromatic or heteroaromatic groups having 5 to 24 ring atoms; Ar 4 -Ar 5 the same or different 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 at each occurrence from N, C(R 6 )、Si(R 6 ), Y a and Y b independently selected at each occurrence from B, P=O, C(R 6 )、Si(R 6 ); When Ar 4 or Ar 5 When it is empty, X b Selected from N, C(R 6 )、Si(R 6 ), Y a Selected from B, P=O, C(R 6 )、Si(R 6 ), X a and Y b In each occurrence, independently selected from N(R 6 )、C(R 6 R 7 )、Si(R 6 R 7 )、C=O、O、C=N(R 6 ), C=C(R 6 R 7 )、P(R 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 are selected from H, D, or a linear alkyl, haloalkyl, alkoxy, thioalkoxy radical having 1 to 20 C atoms, or a branched or cyclic alkyl, haloalkyl, alkoxy, thioalkoxy radical, 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 with the ring to which the groups are bonded.

4. The composition 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 formulae (1a) to (1e), (2a) to (2e), (3a) to (3d), or (4a) to (4d2): Among them, Ar 1 -Ar 3 、Ar 4 -Ar 5 、X 1 、X 2 、X a 、Y b 、R 1 -R 5 The meaning of the symbols is the same as that in claim 3.

5. The composition according to any one of claims 1 to 4, characterized in that Ar1, Ar2, 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:

6. The composition according to claim 1, characterized in that The organic compound H can be polymerized to form a polymer.

7. The composition according to claim 1 or 2, characterized in that The luminophore E is selected from compounds having the following structural formula: in: X is CR9 or N; R1-R9, at each occurrence, are independently selected from hydrogen, alkyl, cycloalkyl, heterocyclyl, alkenyl, cycloalkenyl, alkynyl, hydroxyl, thiol, alkoxy, alkylthio, aryl ether, aryl thioether, aryl, heteroaryl, halogen, cyano, aldehyde, carbonyl, carboxyl, oxycarboxyl, carbamoyl, amino, nitro, silyl, siloxane, borane, and phosphine oxide, and R1-R9 may form a fused ring and an aliphatic ring with adjacent substituents.

8. The composition according to claim 1, characterized in that The composition also comprises an organic resin and / or a solvent.

9. The composition according to any one of claims 1 to 8, characterized in that The organic resin is a thermosetting resin or a UV curable resin.

10. The composition according to any one of claims 1 to 9, characterized in that The proportion of the organic resin is between 20 wt % and 99 wt %.

11. An organic functional material film comprising a composition according to any one of claims 1 to 7, or prepared using a composition according to any one of claims 8 to 10.

12. A photovoltaic device comprising a composition according to any one of claims 1 to 7 or an organic functional material thin film according to claim 11.

13. 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 composition according to any one of claims 1 to 7, or is prepared using a composition according to any one of claims 8 to 10.

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