Compound and application thereof in photoelectric field

Abstract

The invention discloses a pyrene-based compound which has a structure as shown in a chemical formula (I). The compound has a relatively large molar extinction coefficient and fluorescence luminous efficiency, and a color conversion layer prepared from the compound can effectively absorb incident light, so that a relatively thin color conversion layer can be conveniently prepared; the absorption spectrum of the compound can be adjusted by modifying the molecular structure of the compound, different types of color conversion layers can be prepared from the compounds with different chemical structures, light with different colors can be absorbed, and display devices with high color gamut can be manufactured by matching the compounds with light-emitting materials with narrow half-peak widths with different colors.

Description

Compounds and their applications in optoelectronics Technical Field

[0001] The present invention relates to the technical field of organic optoelectronic materials and devices, and in particular to a compound, a polymer, a composition, a mixture, an organic functional material film and a optoelectronic device containing the compound, 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. In patent application number CN202110370887.3, the inventors proposed a host-guest concept for a color conversion layer. This concept utilizes an organic material with a high molar extinction coefficient as the host, absorbing light from the light-emitting unit and transferring it to a luminescent guest with a narrow emission spectrum, thereby achieving a thinner color conversion layer. However, the organic material used as the host is often insufficiently stable, and both its light and thermal stability need to be significantly improved.

[0005] Therefore, there is still a need to further improve the host material and provide a class of host materials with a higher extinction coefficient and better light stability and thermal stability as a color conversion film to achieve a high color gamut of the display.

[0006] Summary of the Invention

[0007] Based on this, the object of the present invention is to provide a compound, a composition, a mixture, an organic functional material film, a photoelectric device containing the same, and applications thereof in organic light-emitting devices.

[0008] The specific technical solution is as follows: The present invention provides a compound comprising a structural unit represented by chemical formula (I),

[0009] R1-R4, at each occurrence, may be identical or different and be selected from H, D, or a linear alkyl, haloalkyl, alkoxy, thioalkoxy group having 1 to 20 C atoms, or a branched or cyclic alkyl, haloalkyl, alkoxy, thioalkoxy, 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 cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, NO2, 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;

[0010] wherein at least three of R1-R4 are the same or different and are selected from one of the chemical formulas (I-1)-(I-4):

[0011] wherein: * represents the site of attachment to pyrene; Ar1 ​​is the same or different and is selected from substituted or unsubstituted aromatic or heteroaromatic groups having 8 to 24 ring atoms; Ar2 to Ar6 are the same or different and are selected from substituted or unsubstituted aromatic or heteroaromatic groups having 5 to 24 ring atoms, and chemical formula (I-2) contains at least one electron-withdrawing group;

[0012] R 11 -R 16 is a substituent which, on each occurrence, may be identical or different and is selected from 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, NO2, 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 radical having 5 to 40 ring atoms, or an arylamino or heteroarylamino radical having 5 to 40 ring atoms, or a combination of these groups.

[0013] The present invention also provides a polymer comprising at least one repeating unit, wherein the repeating unit comprises a structure corresponding to the compound described above.

[0014] The present invention also provides a mixture comprising at least one compound or polymer as described above and another functional material, wherein the another functional material is selected from organic functional materials, which can be selected from hole (also known as electron hole) injection materials (HIM), hole transport materials (HTM), hole blocking materials (HBM), electron injection materials (EIM), electron transport materials (ETM), electron blocking materials (EBM), organic host materials (Host), singlet light emitters (fluorescent light emitters), triplet light emitters (phosphorescent light emitters), thermally excited delayed fluorescence materials (TADF materials) and organic dyes.

[0015] The present invention also provides a composition comprising at least one compound or polymer or mixture as described above, at least one organic solvent, and / or an organic resin.

[0016] The present invention also provides an organic functional material film, which comprises a compound, polymer or mixture as described above, or is prepared using a composition as described above.

[0017] The present invention also provides a photoelectric device comprising the compound, polymer or mixture as described above, or an organic functional material film.

[0018] The present invention also provides an organic light-emitting device, which comprises, from bottom to top, a substrate, 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 is characterized in that: 1) the color conversion layer comprises one of the above-mentioned compounds or polymers, and a light-emitting body E; 2) the color conversion layer at least partially absorbs light emitted by the above-mentioned organic light-emitting layer and transmitted through the second electrode; 3) the light emission spectrum of the compound or polymer is on the short-wavelength side of the absorption spectrum of the light-emitting body E, and at least partially overlaps with each other; 4) the half-peak width of the light emission spectrum of the light-emitting body E is less than or equal to 55nm.

[0019] Beneficial effects: A compound according to the present invention has a large solubility, which is convenient for preparing inks for printing or coating processes and is green and environmentally friendly; after film formation, its absorption and luminescence spectra have little or no red shift; at the same time, it has high stability, especially light stability; and has a large extinction coefficient, which is convenient for preparing thinner color converters for realizing displays with a high color gamut. BRIEF DESCRIPTION OF THE DRAWINGS

[0020] Figure 1: Schematic diagram of a red, green, and blue color display device;

[0021] Figure 2: Absorption and emission spectra of toluene solution of compound 1;

[0022] Figure 3: Absorption and emission spectra of a thin film of compound 1;

[0023] Figure 4: Absorption and emission spectra of toluene solution of compound 3;

[0024] Figure 5: Absorption and emission spectra of a thin film of compound 3;

[0025] Figure 6: Absorption and emission spectra of toluene solution of compound 4;

[0026] Figure 7: Absorption and emission spectra of a thin film of compound 4;

[0027] Figure 8: Absorption and emission spectra of toluene solution of compound 5;

[0028] Figure 9: Absorption and emission spectra of a thin film of compound 5;

[0029] Figure 10: Absorption and emission spectra of toluene solution of compound 8;

[0030] Figure 11: Absorption and emission spectra of a thin film of compound 8;

[0031] Figure 12: Absorption and emission spectra of toluene solution of compound 9;

[0032] Figure 13: Absorption and emission spectra of a thin film of compound 9;

[0033] Figure 14: Absorption and emission spectra of toluene solution of compound 13;

[0034] Figure 15: Absorption and emission spectra of a thin film of compound 13;

[0035] Figure 16: Absorption and emission spectra of toluene solution of compound 14;

[0036] Figure 17: Absorption and emission spectra of a thin film of compound 14;

[0037] Figure 18: Absorption and emission spectra of toluene solution of compound 15;

[0038] Figure 19: Absorption and emission spectra of a thin film of compound 15;

[0039] Figure 20: Absorption and emission spectra of toluene solution of compound 16;

[0040] Figure 21: Absorption and emission spectra of a thin film of compound 16;

[0041] Figure 22: Absorption and emission spectra of toluene solution of compound 17;

[0042] Figure 23: Absorption and emission spectra of a thin film of compound 17;

[0043] Figure 24: Absorption and emission spectra of toluene solution of compound 18;

[0044] Figure 25: Absorption and emission spectra of a thin film of compound 18;

[0045] Figure 26: Absorption and emission spectra of toluene solution of compound 20;

[0046] Figure 27: Absorption and emission spectra of a thin film of compound 20;

[0047] Figure 28: Absorption and emission spectra of a toluene solution of compound E1;

[0048] Figure 29: Absorption and emission spectra of a toluene solution of compound E2;

[0049] Figure 30: Absorption and emission spectra of a toluene solution of compound E3;

[0050] Figure 31: Absorption and emission spectra of the toluene solution of Comparative Example 1;

[0051] FIG32 is a graph showing the absorption and emission spectra of the thin film of Comparative Example 1;

[0052] Figure 33: Absorption attenuation graph of toluene solutions of compounds 1, 3, 4, 5, 8, 9, 13, 15, 16, 20 and Comparative Example 2 after UV irradiation;

[0053] Figure 34: Brightness decay graph of the thin films of Compound 8 and Comparative Example 1 after blue light irradiation;

[0054] Figure 35: Spectrum of top-emitting blue OLED + resin CCL;

[0055] Figure 36: Spectrum of bottom-emitting blue OLED + resin CCL. DETAILED DESCRIPTION

[0056] 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 facilitate a more thorough and comprehensive understanding of the present disclosure.

[0057] 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 the present 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.

[0058] In the present invention, main body material, matrix material, host material and matrix material have the same meaning and can be interchanged.

[0059] In the present invention, metal organic complex, metal organic complex and organometallic complex have the same meaning and can be used interchangeably.

[0060] In the present invention, composition, printing ink, ink and ink have the same meaning and can be interchanged.

[0061] The present invention provides a compound comprising a structural unit represented by chemical formula (I),

[0062] R1-R4, at each occurrence, may be identical or different and be selected from H, D, or a linear alkyl, haloalkyl, alkoxy, thioalkoxy group having 1 to 20 C atoms, or a branched or cyclic alkyl, haloalkyl, alkoxy, thioalkoxy, 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 cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, NO2, 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;

[0063] It is characterized in that at least three of R1-R4 are the same or different and are selected from one of the chemical formulas (I-1)-(I-4):

[0064] wherein: * represents the site of attachment to pyrene; Ar1 ​​is the same or different and is selected from substituted or unsubstituted aromatic or heteroaromatic groups having 8 to 24 ring atoms; Ar2 to Ar6 are the same or different and are selected from substituted or unsubstituted aromatic or heteroaromatic groups having 5 to 24 ring atoms, and chemical formula (I-2) contains at least one electron-withdrawing group;

[0065] R 11 -R 16is a substituent which, on each occurrence, may be identical or different and is selected from 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, NO2, 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 radical having 5 to 40 ring atoms, or an arylamino or heteroarylamino radical having 5 to 40 ring atoms, or a combination of these groups.

[0066] In certain embodiments, the aforementioned R1-R4 are the same or different and are selected from one of the chemical formulas (I-1)-(I-4).

[0067] In certain embodiments, three of the above R1-R4 are selected from the same structural unit.

[0068] In some preferred embodiments, among the above R1-R4, R1 and R3 or R2 and R4 are selected from the same structural unit.

[0069] In some preferred embodiments, among the above R1-R4, R1 and R4 or R2 and R3 are selected from the same structural unit.

[0070] In other preferred embodiments, the above R1-R4 are selected from the same structural unit.

[0071] In a more preferred embodiment, R 11 -R 16The radicals may be selected, at each occurrence, identically or differently, from a linear alkyl, haloalkyl, alkoxy, thioalkoxy radical having 1 to 10 C atoms, or a branched or cyclic alkyl, haloalkyl, alkoxy, thioalkoxy radical having 3 to 10 C atoms, or a silyl radical, or a keto radical having 1 to 10 C atoms, or an alkoxycarbonyl radical having 2 to 10 C atoms, or an aryloxycarbonyl radical having 6 to 10 C atoms, or a cyano, carbamoyl, haloformyl, formyl, isocyanate, isocyanate, thiocyanate, isothiocyanate, hydroxyl, NO2, 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 radical having 5 to 20 ring atoms, or an arylamino or heteroarylamino radical having 5 to 20 ring atoms, or a combination of these radicals.

[0072] 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.

[0073] For the purposes of the present invention, wherein the H atoms on the compounds of the present invention can be replaced by R 20 Group substitution, R 20 The definition of R is the same as above 11, 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 20 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.

[0074] In some preferred embodiments, Ar1 in chemical formula (I-1) is selected from one or a combination of the following structural formulas, which may be further substituted:

[0075] Among them: X1-X8 are selected from CR 32 or N; M1, M2, M3 each independently represent N(R 32 )、C(R 32 R 33 )2、Si(R 32 R 33 )2、O、C=N(R 32 ), C=C(R 32 R 33 )2、P(R 32 ), P(=O)R 32 , S, S=O, SO2 or none; R 30 、R 31 、R 32 、R 33 and D, which may be identical or different on each occurrence, or are selected from H, D, or linear alkyl, haloalkyl, alkoxy, thioalkoxy radicals having 1 to 20 C atoms, or branched or cyclic alkyl, haloalkyl, alkoxy, thioalkoxy, silyl radicals having 3 to 20 C atoms, or keto radicals having 1 to 20 C atoms, or alkoxycarbonyl radicals having 2 to 20 C atoms, or aryloxycarbonyl radicals having 4 to 20 C atoms, or cyano, carbamoyl, haloformyl, formyl, isocyano, isocyano, Cyanate, thiocyanate, isothiocyanate, hydroxyl, NO2, 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.

[0076] In some particularly preferred embodiments, Ar1 is naphthyl.

[0077] In certain preferred embodiments, in the compounds, Ar2-Ar6 are the same or different and are selected from aromatic or heteroaromatic groups having 5 to 20 ring atoms in each occurrence; preferably selected from aromatic or heteroaromatic groups having 5 to 18 ring atoms; more preferably selected from aromatic or heteroaromatic groups having 5 to 15 ring atoms; most preferably selected from aromatic or heteroaromatic groups having 5 to 10 ring atoms; they may be unsubstituted or substituted with one or two R 20 Preferred aryl or heteroaryl groups include benzene, naphthalene, anthracene, phenanthrene, pyridine, benzofuran, pyrene or thiophene.

[0078] In certain preferred embodiments, Ar2-Ar6, when present at each occurrence, are independently selected from the following structural formulas:

[0079] Where: X0 is CR 40 or N; Y0 is selected from CR 41 R 42 , SiR 41 R 42 ,NR 41 , C(=O), S, or O; R 40 -R 42 The definition of R is the same as above 30 .

[0080] Furthermore, Ar2-Ar6, when each occurs, are independently selected from one or a combination of the following chemical formulae, and may be further substituted arbitrarily:

[0081] In a particularly preferred embodiment, Ar2-Ar6 are phenyl groups.

[0082] Preferably, Ar3 or Ar4 in chemical formula (I-2) is selected from an electron-withdrawing group or is substituted by an electron-withdrawing group.

[0083] In some preferred embodiments, Ar3 and Ar4 are selected from an electron withdrawing group or are substituted with an electron withdrawing group.

[0084] In some preferred embodiments, Ar4 is selected from an electron withdrawing group or is substituted with an electron withdrawing group.

[0085] In some preferred embodiments, chemical formula (I-2) contains two electron-withdrawing groups.

[0086] In some preferred embodiments, chemical formula (I-2) contains three electron-withdrawing groups.

[0087] In other preferred embodiments, chemical formula (I-2) contains three or more electron-withdrawing groups.

[0088] The electron-withdrawing group may be selected from F, cyano, a partially or fully fluorinated alkyl chain, or one of the following groups:

[0089] Where: n is 1, 2 or 3; X 1 -X 10 Selected from CR 52 or N, and at least one of them is N; M 1 、M 2 、M 3 Each independently represents N(R 53 )、C(R53 R 54 )2、Si(R 53 R 54 )2、O、C=N(R 53 ), C=C(R 53 R 54 )2、P(R 53 ), P(=O)R 53 , S, S=O, SO2 or none; R 50 -R 54 The definition of R is the same as above 30 .

[0090] In some preferred embodiments, the compounds of the present invention contain -F.

[0091] In some preferred embodiments, the compounds of the present invention contain -CN.

[0092] In other preferred embodiments, the compounds of the present invention contain the following groups:

[0093] In certain embodiments, R in Formula (I-3) 13 and R 14 Selected from different groups.

[0094] In some preferred embodiments, R in formula (I-3) 13 and R 14 are selected from the same group.

[0095] In some particularly preferred embodiments, R in formula (I-3) 13 and R 14 The same is selected from one of methyl, ethyl or isopropyl.

[0096] In certain embodiments, R in Formula (I-4) 13 -R 16 are selected from the same or different groups.

[0097] In some preferred embodiments, R in chemical formula (I-4) 13 and R 14 or R 15 and R 16 are selected from the same group.

[0098] In other preferred embodiments, R in the chemical formula (I-4) 13 -R 16 are selected from the same group.

[0099] In a particularly preferred embodiment, R in formula (I-4) 13 -R16 Equally selected from methyl.

[0100] In certain embodiments, the compounds according to the present invention, wherein SP 3 The total amount of hybrid groups does not exceed 50% of the total molecular weight, more preferably does not exceed 30%, and most preferably does not exceed 20%. 3 The presence of hybrid groups can effectively ensure the thermal stability of the compound and thus ensure the stability of the device.

[0101] In other preferred embodiments, in order to improve solubility and / or improve film-forming properties, the compound according to the present invention, wherein SP 3 The total amount of hybridized groups exceeds 20% of the total molecular weight, preferably exceeds 30%, more preferably exceeds 40%, and most preferably exceeds 50%.

[0102] In some preferred embodiments, the compound 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.

[0103] In other preferred embodiments, the compound has a high fluorescence luminescence efficiency, and its fluorescence quantum efficiency (PLQY) is ≥60%, preferably ≥65%, more preferably ≥70%, even better ≥80%, and most preferably ≥90%.

[0104] In the embodiment of the present invention, HOMO, LUMO and resonance factor intensity f play a key role in the energy level structure of the organic material. The following is an introduction to the determination of these parameters.

[0105] 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.

[0106] The resonance factor strength f can also be obtained through quantum simulation calculations (such as Time-dependent DFT).

[0107] It should be noted that the absolute values ​​of HOMO and LUMO depend on the measurement or calculation method used. Even for the same method, different evaluation methods, such as the onset and peak points on a CV curve, can give different HOMO / LUMO values. Therefore, reasonable and meaningful comparisons should be made using the same measurement and evaluation methods. The description of the embodiments of the present invention uses HOMO and LUMO values ​​based on time-dependent DFT simulations, but this does not affect the application of other measurement or calculation methods.

[0108] The energy structure of a compound has an important influence on its photoelectric properties and stability.

[0109] In certain embodiments, the compound 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.

[0110] In a preferred embodiment, the compound has a larger 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.

[0111] 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.

[0112] In a preferred embodiment, the compound 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.

[0113] 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.

[0114] In a preferred embodiment, the compound has a high solubility in an organic solvent. Preferably, in toluene, the solubility of the compound 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.

[0115] Some examples of suitable compounds of the present invention are listed below (but are not limited to), which may be further optionally substituted:

[0116] The present invention also relates to a polymer comprising at least one repeating unit, characterized in that the repeating unit comprises a structure corresponding to the above-mentioned compound.

[0117] Preferably, the polymer is a side chain polymer comprising a repeating unit as shown in chemical formula (II), wherein U has a structure corresponding to the above compound, and n is an integer greater than or equal to 1.

[0118] In certain embodiments, the content of the repeating unit U in the polymer is from 0.1 mol % to 100 mol %.

[0119] In a preferred embodiment, the content of repeating unit U in the polymer is from 1 mol% to 90 mol%, preferably from 10 mol% to 90 mol%, more preferably from 20 mol% to 80 mol%, even more preferably from 30 mol% to 70 mol%, and most preferably from 40 mol% to 60 mol%.

[0120] The present invention also provides a mixture comprising at least one compound or polymer as described above, and another functional material. The another functional material is selected from organic functional materials, which can be selected from hole (also known as electron hole) injection materials (HIM), hole transport materials (HTM), hole blocking materials (HBM), electron injection materials (EIM), electron transport materials (ETM), electron blocking materials (EBM), organic host materials (Host), singlet emitters (fluorescent emitters), triplet emitters (phosphorescent emitters), thermally excited delayed fluorescence materials (TADF materials) and organic dyes. For example, various organic functional materials are described in detail in WO2010135519A1, US20090134784A1 and WO2011110277A1, and the entire contents of these three patent documents are hereby incorporated herein by reference.

[0121] In a preferred embodiment, the mixture comprises a compound or polymer according to the present invention and a luminescent material. The compound or polymer according to the present invention can serve as the host material, and the luminescent material has a weight percentage of ≤15 wt%, preferably ≤12 wt%, more preferably ≤9 wt%, even more preferably ≤8 wt%, and most preferably ≤7 wt%.

[0122] In a preferred embodiment, the luminescent material is selected from organic fluorescent light-emitting bodies.

[0123] The following is a detailed description of fluorescent emitters (also called singlet emitters).

[0124] 1. Singlet Emitter

[0125] Singlet emitters often have longer conjugated π-electron systems. To date, there have been many examples, such as styrylamine and its derivatives disclosed in JP2913116B and WO2001021729A1, and indenofluorene and its derivatives disclosed in WO2008 / 006449 and WO2007 / 140847.

[0126] In a preferred embodiment, the singlet emitter can be selected from monostyrylamine, distyrylamine, tertiary styrylamine, tetrastyrylamine, styrylphosphine, styryl ether and aromatic amine.

[0127] A monostyrylamine is a compound comprising an unsubstituted or substituted styryl group and at least one amine, preferably an aromatic amine. A distyrylamine is a compound comprising two unsubstituted or substituted styryl groups and at least one amine, preferably an aromatic amine. A tert-styrylamine is a compound comprising three unsubstituted or substituted styryl groups and at least one amine, preferably an aromatic amine. A tetrastyrylamine is a compound comprising four unsubstituted or substituted styryl groups and at least one amine, preferably an aromatic amine. A preferred styrene is diphenylethylene, which may be further substituted. The corresponding phosphines and ethers are defined similarly to the amines. An arylamine or aromatic amine is a compound comprising three unsubstituted or substituted aromatic or heterocyclic rings directly attached to nitrogen. At least one of these aromatic or heterocyclic ring systems is preferably a fused ring system and preferably has at least 14 aromatic ring atoms. Preferred examples include aromatic anthracenamines, aromatic anthracenediamines, aromatic pyreneamines, aromatic pyrenediamines, aromatic chryseneamines, and aromatic chrysenediamines. An aromatic anthracenamine is a compound in which one diarylamine group is directly attached to anthracene, preferably at the 9-position. An aromatic anthracenediamine is a compound in which two diarylamine groups are directly attached to anthracene, preferably at the 9- and 10-positions. Aromatic pyreneamines, aromatic pyrenediamines, aromatic chrysamines, and aromatic chrysenediamines are similarly defined, with the diarylamine groups preferably attached to the 1- or 1,6-positions of the pyrene group.

[0128] Examples of singlet emitters based on vinylamine and aromatic amine, which are also preferred examples, can be found in the following patent documents: WO2006 / 000388, WO2006 / 058737, WO2006 / 000389, WO2007 / 065549, WO2007 / 115610, US7250532B2, DE102005058557A1, CN1583691A, JP08053397A, US6251531B1, US2006 / 210830A, EP1957606A1 and US2008 / 0113101A1, the entire contents of the above-listed patent documents are hereby incorporated herein by reference.

[0129] Examples of singlet emitters based on stilbene and its derivatives are disclosed in US Pat. No. 5,121,029.

[0130] Further preferred singlet emitters can be selected from indenofluorene-amines and indenofluorene-diamines, as disclosed in WO 2006 / 122630, benzindenofluorene-amines and benzindenofluorene-diamines, as disclosed in WO 2008 / 006449, and dibenzoindenofluorene-amines and dibenzoindenofluorene-diamines, as disclosed in WO 2007 / 140847.

[0131] Other materials that can be used as singlet emitters include polycyclic aromatic hydrocarbon compounds, especially derivatives of the following compounds: anthracene such as 9,10-di(2-naphthyl)anthracene, naphthalene, tetraphenyl, xanthene, phenanthrene, pyrene (such as 2,5,8,11-tetra-t-butylperylene), indenopyrene, benzo-fused ring such as (4,4'-bis(9-ethyl-3-carbazolylvinyl)-1,1'-biphenyl), diindenopyrene, decacycloene, hexabenzophenone, fluorene, spirobifluorene, arylpyrene (such as US20060222886), arylenevinyl (such as US5121 029, US5130603), cyclopentadiene such as tetraphenylcyclopentadiene, rubrene, coumarin, rhodamine, quinacridone, pyran such as 4-(dicyanomethylene)-6-(4-(p-dimethylaminophenyl)-2-methyl)-4H-pyran (DCM), thiopyran, bis(azinyl)imine boron compounds (US2007 / 0092753A1), bis(azinyl)methylene compounds, carbostyryl compounds, oxazinones, benzoxazoles, benzothiazoles, benzimidazoles, and dione pyrrolopyrroles. Some materials for singlet emitters can be found in the following patent documents: US20070252517A1, US4769292, and US6020078. The entire contents of the above-listed patent documents are hereby incorporated herein by reference.

[0132] Some examples of suitable singlet emitters are listed below:

[0133] In a particularly preferred embodiment, the mixture comprises a compound or polymer described in the present invention (as the host material H) and a luminophore E, wherein 1) the luminescence spectrum of the compound (host material H) or polymer 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-maximum width (FWHM) of the luminescence spectrum of the luminophore E is less than or equal to 55 nm.

[0134] In a preferred embodiment, the full width at half maximum (FWHM) of the emission spectrum of the luminophore E is ≤50 nm, preferably ≤40 nm, more preferably ≤35 nm, and most preferably ≤30 nm.

[0135] In another preferred embodiment, the luminescent body E has a fluorescence quantum efficiency (PLQY) of ≥60%, preferably ≥65%, more preferably ≥70%, and most preferably ≥80%.

[0136] In a preferred embodiment, the luminophore E is an organic luminophore having a structure shown in chemical formula (1) or (2):

[0137] Where: Ar 1 -Ar 3The 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 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;

[0138] R 1 -R 7In each occurrence, the same or different substituents are independently selected from H, D, or linear alkyl, haloalkyl, alkoxy, thioalkoxy groups having 1 to 20 C atoms, or branched or cyclic alkyl, haloalkyl, alkoxy, thioalkoxy, silyl groups having 3 to 20 C atoms, or substituted keto groups having 1 to 20 C atoms, or alkoxycarbonyl groups having 2 to 20 C atoms, or aryloxycarbonyl groups having 7 to 20 C atoms, or cyano, carbamoyl, haloformyl, formyl , isocyanate, isocyanate, thiocyanate, isothiocyanate, hydroxyl, NO2, 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.

[0139] Examples of organic light-emitting bodies represented by chemical formula (1) or (2) include those disclosed in patent applications with application numbers CN20201109557.7 and CN202110370887.3, the entire contents of which are hereby incorporated herein by reference.

[0140] In addition, for the purpose of the mixture according to the invention, the emitter E can also be further selected from organic compounds (derivatives of bodipyrrolidone) having the following structural formula:

[0141] Where: X is CR 18 or N; R 10 -R 18 are each independently selected from hydrogen, alkyl, cycloalkyl, heterocyclyl, alkenyl, cycloalkenyl, alkynyl, hydroxyl, thiol, alkoxy, alkylthio, arylether, arylthioether, aryl, heteroaryl, halogen, cyano, aldehyde, carbonyl, carboxyl, oxycarboxyl, carbamoyl, amino, nitro, silyl, siloxane, borane, phosphine oxide, and R 10 -R 18 It can form a condensed ring or an aliphatic ring with adjacent substituents.

[0142] In a preferred embodiment, R 16 and R 17 are independently selected from electron withdrawing groups.

[0143] 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:

[0144] Where: X 1 -X 8 、M 1 、M 2 、M 3 、R 50 、R 51 , and n are defined as above.

[0145] Examples of suitable Bodipy derivatives include, but are not limited to:

[0146] In another preferred embodiment, the luminophore E is an inorganic nanoluminophore, as disclosed in patent application number CN202110370819.7, the entire contents of which are hereby incorporated herein by reference.

[0147] The present invention also provides a composition comprising at least one compound or polymer or mixture according to the present invention, at least one organic solvent, and / or an organic resin.

[0148] In a preferred embodiment, the composition comprises one organic resin; in other embodiments, it comprises two or more organic resins; in other embodiments, it comprises three or more organic resins.

[0149] For the purpose of the present invention, the organic resin refers to a resin prepolymer or a resin formed after crosslinking or curing.

[0150] 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.

[0151] 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.

[0152] 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.

[0153] 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, glyceryl monomethacrylate, 2-aminoethyl acrylate, 2-aminoethyl methacrylate, 2-dimethoxy acrylate Methylaminoethyl acrylate, 2-dimethylaminoethyl methacrylate, N,N-dimethylaminoethyl (meth)acrylate, N,N-diethylaminoethyl (meth)acrylate, 2-aminopropyl acrylate, 2-aminopropyl methacrylate, 2-dimethylaminopropyl acrylate, 2-dimethylaminopropyl methacrylate, 3-aminopropyl acrylate, 3-aminopropyl methacrylate, N,N-dimethyl-1,3-propylenediamine benzyl (meth)acrylate, 3-dimethylaminopropyl acrylate, 3-dimethylaminopropyl methacrylate, glycidyl acrylate and glycidyl methacrylate.

[0154] Examples of the acrylonitrile derivatives are acrylonitrile, methacrylonitrile, α-chloroacrylonitrile and vinylidene cyanide.

[0155] Examples of the acrylamide derivatives are acrylamide, methacrylamide, α-chloroacrylamide, N-2-hydroxyethylacrylamide and N-2-hydroxyethylmethacrylamide.

[0156] Examples of vinyl ester derivatives are vinyl acetate, vinyl propionate, vinyl butyrate and vinyl benzoate.

[0157] Examples of the vinyl ether derivatives are vinyl methyl ether, vinyl ethyl ether and allyl glycidyl ether.

[0158] Examples of maleimide derivatives include maleimide, benzylmaleimide, N-phenylmaleimide and N-cyclohexylmaleimide.

[0159] Examples of conjugated diene derivatives are 1,3-butadiene, isoprene and chloroprene.

[0160] 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.

[0161] The organic resin generally has 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.

[0162] 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.

[0163] 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.

[0164] 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).

[0165] 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)).

[0166] In a preferred embodiment, the composition comprises one solvent; in other embodiments, it comprises two or more solvents; in other embodiments, it comprises three or more solvents.

[0167] In a preferred embodiment, the composition according to the present invention is a solution.

[0168] In another preferred embodiment, the composition according to the present invention is a suspension.

[0169] The composition in the embodiment of the present invention may include 0.01wt% to 20wt% of the compound, preferably 0.1wt% to 20wt%, more preferably 0.2wt% to 20wt%, and most preferably 1wt% to 15wt% of the compound.

[0170] The composition of the present invention can be used to form a color conversion layer using methods such as inkjet printing, transfer printing, and photolithography. In this case, the color conversion material of the present invention, alone or in combination with other materials, is dissolved in an organic solvent to form an ink. The mass concentration of the color conversion material of the present invention 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 layer results in a higher color conversion efficiency of the color conversion layer.

[0171] Other materials that may be added to the ink include, but are not limited to, the following: polyethylene, polypropylene, polystyrene, polycarbonate, polyacrylate, polyvinyl pyrrolidone, polyvinyl alcohol, polyvinyl acetate, polyethylene glycol, polysiloxane, polyacrylonitrile, polyvinyl chloride, polyvinylidene chloride, polyethylene terephthalate, polybutylene terephthalate, polyvinyl butyrate, polyamide, polyoxymethylene, polyimide, polyetheretherketone, polysulfone, polyarylether, polyaramid, cellulose, modified cellulose, cellulose acetate, nitrocellulose, or mixtures thereof.

[0172] In some preferred embodiments, the organic solvent is selected from esters, aromatic ketones or aromatic ethers, aliphatic ketones or aliphatic ethers, or inorganic ester compounds such as borate esters or phosphate esters, or a mixture of two or more solvents.

[0173] In other embodiments, suitable and preferred solvents are aliphatic, cycloaliphatic or aromatic hydrocarbons, amines, thiols, amides, nitriles, esters, ethers, polyethers, alcohols, diols or polyols.

[0174] In other embodiments, alcohols represent a suitable class of solvents. Preferred alcohols include alkylcyclohexanols, particularly methylated aliphatic alcohols, naphthols, and the like.

[0175] 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.

[0176] The solvent can be used alone or as a mixture of two or more organic solvents.

[0177] In certain embodiments, the composition according to the present invention comprises a compound as described above and at least one organic solvent, and may further comprise another organic solvent. Examples of the other organic solvent 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 mixtures thereof.

[0178] In some preferred embodiments, according to a composition of the present invention, the other organic 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 mixture of two or more solvents.

[0179] 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-di ... Fluorodiphenylmethane, 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.

[0180] In other embodiments, suitable and preferred alternative organic solvents are aliphatic, alicyclic or aromatic hydrocarbons, amines, thiols, amides, nitriles, esters, ethers, polyethers.

[0181] The other organic solvent may be a cycloalkane, such as decalin.

[0182] In other preferred embodiments, a composition according to the present invention comprises at least 50 wt% of an alcohol solvent, preferably at least 80 wt% of an alcohol solvent, and particularly preferably at least 90 wt% of an alcohol solvent.

[0183] In some preferred embodiments, solvents particularly suitable for the present invention are solvents having a Hansen solubility parameter within the following ranges:

[0184] δ d (Dispersion force) 17.0~23.2MPa 1 / 2 range, especially in the range of 18.5~21.0MPa 1 / 2 scope;

[0185] δ p (Polar force) 0.2~12.5MPa 1 / 2 range, especially in the range of 2.0~6.0MPa 1 / 2 scope;

[0186] δ h (Hydrogen bond force) 0.9~14.2MPa 1 / 2 range, especially in the range of 2.0~6.0MPa 1 / 2 range.

[0187] In the composition of the present invention, the organic solvent should be selected based on its boiling point. In the present invention, the boiling point of the organic 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 organic solvent can be evaporated from the solvent system to form a film containing the functional material.

[0188] In some preferred embodiments, a composition according to the present invention,

[0189] 1) Its viscosity @25°C is in the range of 1 cPs to 100 cPs, and / or

[0190] 2) Its surface tension @25℃ is in the range of 19 dyne / cm to 50 dyne / cm.

[0191] In the composition of the present invention, the organic solvent should be selected based on its surface tension. Suitable ink surface tension parameters are tailored to specific substrates and printing methods. For example, for inkjet printing, in a preferred embodiment, the surface tension of the organic solvent at 25°C is approximately 19 dyne / cm to 50 dyne / cm; more preferably, 22 dyne / cm to 35 dyne / cm; and most preferably, 25 dyne / cm to 33 dyne / cm.

[0192] In a preferred embodiment, the surface tension of the ink according to the present invention 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.

[0193] In the composition of the present invention, the organic solvent should be selected taking into account the viscosity parameters of the ink. Viscosity can be adjusted by various methods, such as by selecting an appropriate organic solvent and the concentration of the functional material in the ink. In a preferred embodiment, the viscosity of the organic solvent is less than 100 cps; more preferably, less than 50 cps; and most preferably, between 1.5 and 20 cps. Viscosity refers to the viscosity at the ambient temperature during printing, generally between 15-30°C, preferably 18-28°C, more preferably 20-25°C, and most preferably 23-25°C. Such a composition is particularly suitable for inkjet printing.

[0194] In a preferred embodiment, the composition according to the present invention has a viscosity at 25°C in the range of about 1 cps to 100 cps; more preferably in the range of 1 cps to 50 cps; and most preferably in the range of 1.5 cps to 20 cps.

[0195] The ink obtained from the organic solvent that meets the above-mentioned boiling point, surface tension parameters and viscosity parameters can form a functional material film with uniform thickness and composition properties.

[0196] Salt compounds are difficult to purify and can easily introduce impurities, which can affect photoelectric performance. For the purposes of the present invention, in certain preferred embodiments, the composition or mixture does not contain any salt compounds, and preferably does not contain any organic acid salts formed from organic acids and metals. For cost considerations, the present invention preferably excludes organic acid salts containing transition metals and lanthanides.

[0197] The present invention further provides an organic functional material film comprising a compound or polymer as described above, or a mixture thereof, or prepared using a composition as described above. Preferably, the organic functional material film is prepared using a composition as described above.

[0198] The present invention also provides a method for preparing the organic functional material thin film, comprising the following steps:

[0199] 1) preparing a composition according to the present invention;

[0200] 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, torsional roller printing, offset printing, flexographic printing, rotary printing, spray coating, brush coating or pad printing, and slot extrusion coating;

[0201] 3) The obtained film is heated at a temperature of at least 50° C. and optionally irradiated with ultraviolet light to cause a cross-linking reaction and solidify the film.

[0202] The thickness of the organic functional material film is generally 50nm-200μm, preferably 100nm-150μm, more preferably 500nm-100μm, even more preferably 1μm-50μm, and most preferably 1μm-20μm.

[0203] In another preferred embodiment, the thickness of the organic functional material film is between 20 nm and 20 μm, preferably less than 15 μm, more preferably less than 10 μm, even better less than 8 μm, particularly preferably less than 6 μm, most preferably less than 4 μm, and most preferably less than 2 μm.

[0204] Another object of the present invention is to provide use of the above compound or mixture in optoelectronic devices.

[0205] In some embodiments, the optoelectronic device may be selected from organic light emitting diodes (OLEDs), organic photovoltaic cells (OPVs), organic light emitting cells (OLEECs), organic field effect transistors (OFETs), organic light emitting field effect transistors (OLEDs), organic lasers, organic spintronic devices, organic sensors, and organic plasmon emitting diodes.

[0206] Furthermore, the present invention provides a photoelectric device comprising the compound, polymer, mixture or organic functional material film as described above.

[0207] In some embodiments, the optoelectronic device may be selected from organic light emitting diodes (OLEDs), organic photovoltaic cells (OPVs), organic light emitting cells (OLEECs), organic field effect transistors (OFETs), organic light emitting field effect transistors, organic lasers, organic spintronic devices, organic sensors, and organic plasmon emitting diodes.

[0208] Preferably, the optoelectronic device is an electroluminescent device, such as 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 one of the above-mentioned compounds or mixtures or a thin film of an organic functional material. 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, and a cathode passivation layer (CPL).

[0209] 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.

[0210] In another preferred embodiment, the optoelectronic device comprises a light-emitting unit and a color conversion layer, wherein the color conversion layer comprises one of the above-mentioned compounds or mixtures or a thin film of an organic functional material.

[0211] 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).

[0212] In a preferred embodiment, the light emitting unit emits blue light, which is converted into green light by the color conversion layer.

[0213] 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.

[0214] 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.

[0215] The present invention further relates to an organic light-emitting device, comprising, from bottom to top, a substrate, a first electrode, an organic light-emitting layer, a second electrode, a color conversion layer, and an encapsulation layer (e.g., the outermost encapsulation layer), wherein the second electrode is at least partially transparent, wherein: 1) the color conversion layer comprises a compound or polymer of the present invention and a luminophore E; 2) the color conversion layer can at least partially absorb light emitted by the organic light-emitting layer that passes through the second electrode; 3) the luminescence spectrum of the compound or polymer is on the short-wavelength side of the absorption spectrum of the luminophore E and at least partially overlaps with each other; and 4) the full width at half maximum (FWHM) of the luminescence spectrum of the luminophore E is less than or equal to 55 nm.

[0216] The compounds and luminophore E of the present invention and their preferred embodiments are as described above.

[0217] In a preferred embodiment, the color conversion layer can absorb 30% or more, preferably 40% or more, and most preferably 45% or more of the light emitted by the organic light emitting layer and transmitted through the second electrode.

[0218] In another preferred embodiment, the color conversion layer can absorb 90% or more, preferably 95% 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.

[0219] In some embodiments, the thickness of the color conversion layer is between 100 nm and 5 μm, preferably between 150 nm and 4 μm, more preferably between 200 nm and 3 μm, and most preferably between 200 nm and 2 μm.

[0220] In a preferred embodiment, the organic electroluminescent device is an OLED. More preferably, the first electrode is an anode and the second electrode is a cathode. Particularly preferably, the organic electroluminescent device is a top emission OLED.

[0221] 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).

[0222] 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.

[0223] The cathode can 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 difference between the work function of the cathode and the LUMO energy level or conduction band energy level of the luminophore in the light-emitting layer or the n-type semiconductor material serving as the electron injection layer (EIL), electron transport layer (ETL), or hole blocking layer (HBL) is less than 0.5 eV, preferably less than 0.3 eV, and most preferably less than 0.2 eV. In principle, all materials that can be used as cathodes in OLEDs are possible 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 can be deposited using any suitable technique, such as a suitable physical vapor deposition method, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), and the like. In a preferred embodiment, the cathode has a transmittance of ≥40% in the range of 400 nm to 680 nm, preferably ≥45%, more preferably ≥50%, and most preferably ≥60%. A Mg:Ag alloy of 10 nm to 20 nm in thickness can be used as the transparent cathode, with a Mg:Ag ratio ranging from 2:8 to 0.5:9.5.

[0224] In the organic electroluminescent device, 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.

[0225] Furthermore, the organic electroluminescent device further includes a cathode capping layer (CPL for short).

[0226] In a preferred embodiment, the CPL is located between the second electrode and the color conversion layer.

[0227] In another preferred embodiment, the CPL is located above the color conversion layer.

[0228] Materials used for CPL generally need to have a higher refractive index n, such as n≥1.95@460nm, n≥1.90@520nm, n≥1.85@620nm. Examples of materials used for CPL include:

[0229] More examples of further CPL materials can be found in the following patent documents: KR20140128653A, KR20140137231A, KR20140142021A, KR20140142923A, KR20140143618A, KR20140145370A, KR20150004099A, KR20150012835A, US9496520B2, US2015069350A1, CN10382 8485B, CN104380842B, CN105576143A, TW201506128A, CN103996794A, CN103996795A, CN104744450A, CN104752619A, CN101944570A, US2016308162A1, US9095033B2, US2014034942A1, WO2017014357A1; the above patent documents are hereby incorporated into this document for reference.

[0230] 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 aforementioned compound (host material H), and the luminophore E. In certain embodiments, the mass ratio of the aforementioned compound (host material H) is 50%-20%, and the mass ratio of the luminophore E is 10%-15%.

[0231] Preferably, in the above-mentioned organic electroluminescent device, the encapsulation layer is a thin film encapsulation (TFE).

[0232] The present invention further relates to a display panel, wherein at least one pixel comprises the above-mentioned organic electroluminescent device.

[0233] 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.

[0234] Specific embodiments

[0235] Example 1: Compound Synthesis Example

[0236] 1. Synthesis of Compound 1

[0237] 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, then heated to 100°C and refluxed for 5 hours. After the reaction was completed, the mixture was cooled to room temperature and extracted three times with ethyl acetate and saturated brine. The organic phase was concentrated and passed through a short silica gel column (eluent: dichloromethane:n-hexane = 1:10). The product was collected and concentrated to obtain 45 g of dark brown solid intermediate 1a in a 93.7% yield.

[0238] Intermediate 1a (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 evacuation and nitrogen refilling, the mixture was heated to 140°C and refluxed for 12 hours. After the reaction, the mixture was cooled to room temperature and extracted three times with ethyl acetate and saturated brine. The organic phase was concentrated, and the product was dissolved in hot toluene and passed through an insulated silica gel column while still hot. The filtrate was collected, concentrated, slurried with n-hexane, and filtered. The filter cake was rinsed with n-hexane to obtain 5.1 g of crude product. The crude product was slurried with tetrahydrofuran and filtered while still hot to obtain 1 g of solid powder with a yield of 2.1%.

[0239] 2. Synthesis of Compound 2

[0240] 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, and 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 2a in a yield of 94.6%.

[0241] Intermediate 2a (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 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, 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 with a yield of 9.5%.

[0242] 3. Synthesis of Compound 3

[0243] 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 3a in an 89.4% yield.

[0244] Intermediate 3a (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 powder with a yield of 42.8%.

[0245] 4. Synthesis of Compound 4

[0246] 2,6-Dimethylaniline (14.85 g, 122.73 mmol), 4a (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 dry, clean three-necked flask. The mixture was evacuated and filled with nitrogen three times, and 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 4b in a yield of 40.9%.

[0247] Intermediate 4b (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. The mixture was evacuated and filled with nitrogen three times, 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 to obtain a crude product, which was then purified by silica gel column chromatography (eluent: dichloromethane:petroleum ether = 1:20) to obtain 1.8 g of a solid powder in a yield of 9.9%.

[0248] 5. Synthesis of Compound 5

[0249] 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, 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 48 g of intermediate 5a as an oil with a yield of 89.72%.

[0250] Intermediate 5a (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 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 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 30 g of crude product, which was recrystallized from tetrahydrofuran to obtain 22.5 g of solid powder with a yield of 41.3%.

[0251] 6. Synthesis of Compound 6

[0252] 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, 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, 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 6a as an oil in an 86.9% yield.

[0253] Intermediate 6a (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 refilling, 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 a solid powder with a yield of 10%.

[0254] 7. Synthesis of Compound 7

[0255] 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 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, 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 7a in a yield of 92.1%.

[0256] Intermediate 7a (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 evacuation and nitrogen filling, the mixture was heated to 140°C and refluxed for 14 hours. After the reaction was complete, 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 in a 9.1% yield.

[0257] 8. Synthesis of Compound 8

[0258] 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 dry, clean three-necked flask. The mixture was evacuated and filled with nitrogen three times, and 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 8a as an oil in a 96.3% yield.

[0259] Intermediate 8a (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 three times, 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 with a yield of 18.5%.

[0260] 9. Synthesis of Compound 9

[0261] 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 9a as an oil in a 90.9% yield.

[0262] Intermediate 9a (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 powder with a yield of 5.2%.

[0263] Other ingredients:

[0264] The synthesis of compounds 10-21 was similar to that of compounds 1-9. The synthesis of comparative example 1 was in accordance with PCT patent (International Publication No. WO2022213993A1), and the synthesis of comparative example 2 was in accordance with US20150069350A1.

[0265] 22. Synthesis of polymer P1, where x:y = 1:10

[0266] 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%.

[0267] 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 filling, 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, with a yield of 71.2%.

[0268] 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%.

[0269] Intermediate P1c (5 g, 4.25 mmol), 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 filling, 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 3.5 g of intermediate P1e, with a yield of 61.2%.

[0270] 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 250 ml, clean, three-necked flask. After three cycles of evacuation and nitrogen filling, the mixture was stirred and irradiated with UV light for 12 hours. After completion of the reaction, the monomers were removed by dialysis and dried to obtain 1.56 g of polymer P1 (a 25.1% yield).

[0271] 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.

[0272] Example 2: Energy level structure of the compound

[0273] 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.

[0274] HOMO(eV)=((HOMO(G)×27.212)-0.9899) / 1.1206

[0275] LUMO(eV)=((LUMO(G)×27.212)-2.0041) / 1.385

[0276] The HOMO (G) and LUMO (G) are directly calculated using Gaussian 09W, with units in Hartree. The results are shown in Table 1 below.

[0277] Table 1

[0278] Example 3: Solubility of Compounds

[0279] The solubility of the compound in toluene was determined as follows:

[0280] 1. Place 1000 mg of toluene solution in a clear glass sample bottle.

[0281] 2. Weigh a certain amount of compound and dissolve it in toluene. Shake and let it stand until it is completely dissolved.

[0282] 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.

[0283] 4. Repeat the above steps until a precipitate appears and the compound no longer dissolves.

[0284] 5. Record the total mass of compound added and calculate the solubility.

[0285] The solubility of compounds 1-21 and E1-E3 in toluene is shown in Table 2 below.

[0286] Table 2

[0287] Example 4: Abs / UV and extinction coefficient of the compound (comparison of solution and film)

[0288] The extinction coefficient of the compound and its Abs / UV spectrum in solution were determined as follows:

[0289] 1. Use a volumetric flask to prepare a toluene solution of the compound with a certain molar concentration.

[0290] 2. Use a UV-visible spectrophotometer (Puxi T9s) to measure the absorption spectrum of the solution and obtain the absorption peak position.

[0291] 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.

[0292] 4. The emission spectrum of the solution was measured using a fluorescence spectrometer (Hitachi, F-4700FL Spectrophotometer) to obtain the emission peak position.

[0293] The Abs / UV spectrum of the compound in the film was measured by the following method:

[0294] 1. Prepare a toluene solution of the compound with a certain concentration.

[0295] 2. Apply the prepared toluene solution on a clean glass substrate.

[0296] 3. Spin coating and baking at 80℃ for 1 min to obtain a compound film.

[0297] 4. Use a UV-visible spectrophotometer (Puxi T9s) to measure the absorption spectrum of the film and obtain the absorption peak position.

[0298] 5. The emission spectrum of the film was measured using a fluorescence spectrometer (Hitachi, F-4700FL Spectrophotometer) to obtain the emission peak position.

[0299] The extinction coefficients of the compounds and their absorption and emission peaks in solution and film are shown in Table 3.

[0300] Table 3

[0301] The above table shows that the compounds according to the present invention tested all have relatively high molar extinction coefficients.

[0302] Figures 2-27 sequentially show the absorption and emission spectra of toluene solutions and thin films of compounds 1, 3, 4, 5, 8, 9, 13, 14, 15, 16, 17, 18, and 20. These figures demonstrate that the absorption and emission spectra of the compounds of the present invention in solution and thin films are very similar, with the red shift in the thin film spectra being very small. This is because the ortho-substitution of the aryl group (here, benzene) in the aromatic amine effectively prevents intermolecular stacking in the thin film.

[0303] As described above (Example 4), the optical properties of the compounds: absorption and fluorescence spectra were measured using a spectrophotometer (Puxi T9s) and a fluorescence spectrometer (Hitachi, F-4700FL Spectrophotometer), respectively. Figure 28 shows the absorption and emission spectra of a toluene solution of Compound E1; Figure 29 shows the absorption and emission spectra of a toluene solution of Compound E2; Figure 30 shows the absorption and emission spectra of a toluene solution of Compound E3; and Figures 31 and 32 show the absorption and emission spectra of the toluene solution and film of Comparative Example 1. Compounds E1-E3 have narrow emission spectra, with a Full Width at Half Maximum (FWHM) less than 40 nm. The emission spectrum of the film of Comparative Example 1 exhibits a significant red shift and widened half-maximum width. While it can still function as a green or red light source, the color purity of the green light may be affected. In contrast, the film spectra of the compounds according to the present invention are very similar to the solution spectra, with a very small red shift, making them more suitable for the preparation of CCLs with high color purity.

[0304] Example 5: Optical properties and UV stability of compounds

[0305] The test method for the UV stability of the compound is as follows:

[0306] Prepare 1×10 -5 Take 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.

[0307] Figure 33 shows the absorption attenuation of toluene solutions of Compounds 1, 3, 4, 5, 8, 9, 13, 15, 16, and 20, as well as Comparative Example 2, after UV irradiation. The experimental results are shown in the following table, where the t80 of Comparative Example 2 is taken as 100%. Compared to Comparative Example 2, the compounds according to the present invention exhibit significantly improved photostability.

[0308] Table 4

[0309] Example 6: Blue Light Stability of Compound Films

[0310] The test method for the blue light stability of the film of Compound 8 and Comparative Example 1 is as follows:

[0311] Evaporate a compound film of about 800nm, seal it with a glass cover, and place it on a blue light LED (460nm, 3000cd / m 2The 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 measured over a period of time to obtain a brightness decay curve, as shown in Figure 34. As can be seen from Figure 34, the photostability of the film of Compound 8 was significantly improved compared to that of Comparative Example 1.

[0312] Example 7: Preparation of Color Conversion Film (CCL)

[0313] 7.1 Evaporation film: Compound 8 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, so that the two organic compounds evaporate and deposit on the glass substrate. Stop heating after reaching the target thickness, wait for it to cool to 80℃, fill the thermal evaporation equipment with nitrogen to reach atmospheric pressure, and then open the cavity to obtain the evaporated CCL film.

[0314] 7.2 Solution-processed film: Dissolve 48 mg of compound 8 in 1 mL of toluene 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 heat at 80°C for 5 min to obtain a CCL film.

[0315] 7.3 Resin film: Dissolve 48 mg of compound 8 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.

[0316] CCLs based on other organic compounds can be prepared in the same manner according to 7.1, 7.2 or 7.3.

[0317] Example 8: Results of OLED or LED+CCL film

[0318] 1. Top-emitting blue OLED + resin CCL: On the light-emitting surface of the top-emitting blue OLED, prepare a CCL resin film (E3 as the light-emitting body) according to 7.3 above, with a thickness of about 4 μm.

[0319] 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.

[0320] 3. A luminance meter (Foshida, CS-2000A) was used to measure 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. Figure 35 shows a top-emitting blue OLED + resin CCL (with E3 as the luminescent element), and Figure 36 shows a bottom-emitting blue OLED + resin CCL (with E3 as the luminescent element). As shown, the resin CCL according to the present invention can absorb substantially 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.

[0321] 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.

[0322] The above-described embodiments merely represent several implementation methods of the present invention. While the 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 various modifications 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 compound comprising a structural unit represented by chemical formula (I), R1-R4, at each occurrence, may be identical or different and be selected from H, D, or a linear alkyl, haloalkyl, alkoxy, thioalkoxy group having 1 to 20 C atoms, or a branched or cyclic alkyl, haloalkyl, alkoxy, thioalkoxy, 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 cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, NO2, 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 in that At least three of R1-R4 are the same or different and are selected from one of the chemical formulas (I-1)-(I-4): in: * represents the attachment site to pyrene; Ar1 is selected from a substituted or unsubstituted aromatic or heteroaromatic ring system having 8 to 24 ring atoms; Ar2 to Ar6 are the same or different and are selected from substituted or unsubstituted aromatic or heteroaromatic groups having 5 to 24 ring atoms, and the chemical formula (I-2) contains at least one electron-withdrawing group; R 11 -R 16 is a substituent which, on each occurrence, may be identical or different and is selected from 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, NO2, 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 radical having 5 to 40 ring atoms, or an arylamino or heteroarylamino radical having 5 to 40 ring atoms, or a combination of these groups.

2. The compound according to claim 1, wherein Ar1 in chemical formula (I-1) is selected from one or a combination of the following structural formulas, which may be further substituted: in: X1-X8 selected in CR 32 or N; M1, M2, M3 each independently represent N(R 32 )、C(R 32 R 33 )2、Si(R 32 R 33 )2、O、C=N(R 32 ), C=C(R 32 R 33 )2、P(R 32 ), P(=O)R 32 , S, S=O, SO2 or none; R 30 、R 31 、R 32 、R 33 and D, which may be identical or different on each occurrence, or are selected from H, D, or linear alkyl, haloalkyl, alkoxy, thioalkoxy radicals having 1 to 20 C atoms, or branched or cyclic alkyl, haloalkyl, alkoxy, thioalkoxy, silyl radicals having 3 to 20 C atoms, or keto radicals having 1 to 20 C atoms, or alkoxycarbonyl radicals having 2 to 20 C atoms, or aryloxycarbonyl radicals having 4 to 20 C atoms, or cyano, carbamoyl, haloformyl, formyl, isocyano, isocyano, Cyanate, thiocyanate, isothiocyanate, hydroxyl, NO2, 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.

3. The compound according to claim 1, characterized in that Ar2-Ar6, when present at each occurrence, are independently selected from one or a combination of the following structural formulae, and may be further substituted with any other:

4. The compound according to claim 1, characterized in that The electron-withdrawing group in formula (I-2) may be selected from F, cyano, a partially or fully fluorinated alkyl chain, or one of the following groups: Where: n is 1, 2 or 3; X 1 -X 10 Selected from CR 52 or N, and at least one of them is N; M 1 、M 2 、M 3 Each independently represents N(R 53 )、C(R 53 R 54 )2、Si(R 53 R 54 )2、O、C=N(R 53 ), C=C(R 53 R 54 )2、P(R 53 ), P(=O)R 53 , S, S=O, SO2 or none; R 50 -R 54 and D, which may be identical or different on each occurrence, or are selected from H, D, or linear alkyl, haloalkyl, alkoxy, thioalkoxy radicals having 1 to 20 C atoms, or branched or cyclic alkyl, haloalkyl, alkoxy, thioalkoxy, silyl radicals having 3 to 20 C atoms, or keto radicals having 1 to 20 C atoms, or alkoxycarbonyl radicals having 2 to 20 C atoms, or aryloxycarbonyl radicals having 4 to 20 C atoms, or cyano, carbamoyl, haloformyl, formyl, isocyano, isocyano, Cyanate, thiocyanate, isothiocyanate, hydroxyl, NO2, 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.

5. A polymer comprising at least one repeating unit, characterized in that: The repeating unit comprises a structure corresponding to the compound according to any one of claims 1 to 4.

6. A mixture comprising at least one compound according to any one of claims 1 to 4 or the polymer according to claim 5 and another functional material, wherein the another functional material is selected from organic functional materials, which can be selected from hole injection materials, hole transport materials, hole blocking materials, electron injection materials, electron transport materials, electron blocking materials, organic matrix materials, singlet light emitters, triplet light emitters, thermally excited delayed fluorescence materials and organic dyes.

7. The mixture according to claim 6, characterized in that The mixture further comprises a luminophore E, 1) the luminescence spectrum of the compound or the polymer 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.

8. A composition comprising at least one compound according to any one of claims 1 to 4 or a polymer according to claim 5, or a mixture according to any one of claims 6 to 7, at least one organic solvent, and / or an organic resin.

9. An organic functional material film comprising a compound according to any one of claims 1 to 4 or a polymer according to claim 5, or a mixture according to any one of claims 6 to 7, or prepared using a composition according to claim 8.

10. A photovoltaic device comprising a compound according to any one of claims 1 to 4 or a polymer according to claim 5, or a mixture according to any one of claims 6 to 7, or an organic functional material thin film according to claim 9.

11. An organic light-emitting device comprising, from bottom to top, a substrate, 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, characterized in that: 1) The color conversion layer comprises a compound according to any one of claims 1 to 4 or a polymer according to claim 5, and a luminophore E; 2) the color conversion layer at least partially absorbs light emitted by the above organic light-emitting layer through the second electrode; 3) the luminescence spectrum of the compound or polymer is on the short wavelength side of the absorption spectrum of the luminophore E and at least partially overlaps with each other; 4) the half-peak width of the luminescence spectrum of the luminophore E is less than or equal to 55 nm.

Images