Compounds and their use in the field of optoelectronics

Abstract

The present application discloses a kind of compound comprising at least one chemical formula (1)-(4) structural unit, such compound comprises an alcohol-soluble or water-soluble group. Such compound has a large molar extinction coefficient, and the color conversion layer made of it can effectively absorb incident light, facilitating the preparation of a thinner color conversion layer. The alcohol-soluble or water-soluble group allows the compound to be easily dissolved in environmentally friendly solvents, forming a printing ink. Moreover, the peak position of the absorption spectrum of the compound can be adjusted by modifying its molecular structure. Different types of color conversion layers can be prepared using compounds with different chemical structures, capable of absorbing different colors of light. Light-emitting devices using such compounds can produce display devices with high color gamut.

Description

[0001] This application is a divisional application of application number 202280026667.1, filed on April 6, 2022, entitled "Compounds and Their Applications in the Optoelectronic Field". Technical Field

[0002] This invention relates to the field of organic optoelectronic materials and technology, and in particular to a compound, compositions, mixtures, organic functional material thin films and optoelectronic devices containing the compound, and their applications in the optoelectronic field. Background Technology

[0003] According to the principles of colorimetry, the narrower the half-width at half-maximum (HWHM) of light entering the human eye, the higher the color purity and the more vibrant the color. Display devices made with red, green, and blue primary colors of light with such narrow HWHMs display a wide color gamut, realistic images, and high image quality.

[0004] There are currently two main methods for achieving full-color displays. The first involves the display device actively emitting red, green, and blue light, a typical example being RGB-OLED displays. The mature technology currently uses vacuum evaporation of fine metal masks to create the three-color light-emitting devices. This process is complex, costly, and makes it difficult to achieve high-resolution displays exceeding 600ppi. The second method uses a color converter to transform the single-color light emitted by the light-emitting device into multiple colors, thus achieving full-color display. For example, Samsung uses a blue OLED with red and green quantum dot (QD) films as the color converter. This method uses simpler light-emitting devices with higher yields, and the color converter can be implemented using different technologies such as evaporation, inkjet printing, transfer printing, and photolithography. It can be applied to display products with varying resolution requirements, from low-resolution large-screen TVs (only 50ppi) to high-resolution silicon-based microdisplays (over 3000ppi).

[0005] Currently, the color conversion materials used in mainstream color converters are mainly of two types. One is inorganic nanocrystals, commonly known as quantum dots. These are nanoparticles of inorganic semiconductor materials (InP, CdSe, CdS, ZnSe, etc.) with diameters between 2-8 nm. Due to size effects, these materials exhibit quantum confinement effects, emitting light at specific frequencies. The frequency of the emitted light changes with its size, thus the color of the emitted light can be controlled by adjusting its size. Limited by current quantum dot synthesis and separation technologies, the full width at half maximum (FWHM) of Cd-containing quantum dots is currently 25-40 nm, and their color purity meets the requirements of NTSC displays. The FWHM of Cd-free quantum dots is between 35-75 nm. However, because Cd pollutes the environment and has serious toxic effects on human health, most countries prohibit the use of Cd-containing quantum dots in the manufacture of electronic products. Furthermore, inorganic quantum dots generally have low extinction coefficients, requiring thicker films, typically 10 micrometers or more, to achieve complete absorption of blue light. This poses a significant challenge to mass production processes, especially for Samsung's blue OLED technology combining red and green quantum dots. The second type is organic dyes, including various conjugated small organic molecules with chromophores. These organic dyes generally have high extinction coefficients, but due to intramolecular thermal relaxation and the relatively high vibrational energy within organic molecules, their emission peaks are broad, typically above 60 nm. Additionally, color converters or thin films are generally prepared using solution processing methods. Currently, commonly used organic conjugated systems are relatively rigid and have limited solubility in organic solvents, resulting in poor processability and making them difficult to use in the fabrication of displays combining blue light and color converters.

[0006] Therefore, if organic materials can be further improved to provide a type of organic material with a high molar extinction coefficient, high solubility, and good processing performance, as a color conversion film, the current technical difficulties of adding red and green quantum dots to blue OLEDs can be solved, and a high color gamut display can be achieved. Summary of the Invention

[0007] Based on this, the purpose of the present invention is to provide a compound, a composition comprising the same, a mixture thereof, an organic functional material thin film and an optoelectronic device, and the application thereof in the optoelectronic device.

[0008] The specific technical solution is as follows: This invention provides a compound comprising a structural unit represented by one of the chemical formulas (1)-(4).

[0009] The symbols and markings used have the following meanings: R1-R4 are substituents, which may be the same as or different from straight-chain alkyl, haloalkyl, alkoxy, or thioalkoxy groups having 1 to 20 carbon atoms; branched or cyclic alkyl, haloalkyl, alkoxy, thioalkoxy, or silyl groups having 3 to 20 carbon atoms; substituted ketone groups having 1 to 20 carbon atoms; alkoxycarbonyl groups having 2 to 20 carbon atoms; or aryloxycarbonyl groups having 7 to 20 carbon atoms; cyano groups (-CN); carbamoyl groups; and alkyl groups. The compound contains at least one alcohol-soluble or water-soluble group, including: a hydroxyl group (-C(=O)NH2), a haloformyl group (-C(=O)-X where X represents a halogen atom), a formyl group (-C(=O)-H), an isocyanate group, an isocyanate group, a thiocyanate group or an isothiocyanate group, a hydroxyl group, a NO2 group, a CF3 group, a Cl group, a Br group, a F group, an I group, a crosslinkable group, or a substituted or unsubstituted aromatic or heteroaromatic ring system having 5 to 40 ring atoms, or an aryloxy 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 substituents, or a combination of these substituents; n and o are independently selected from natural numbers 1 to 10, and m and p are independently selected from natural numbers 1 to 12.

[0010] The present invention also provides a mixture comprising at least one compound as described above and another functional material, wherein the other functional material is selected from organic functional materials, and may be selected from hole injection or transport materials (HIM / HTM), hole blocking materials (HBM), electron injection or transport materials (EIM / ETM), electron blocking materials (EBM), organic matrix materials (Host), singlet emitters (fluorescent emitters), triplet emitters (phosphorescent emitters), thermally excited delayed fluorescence materials (TADF materials), and organic dyes.

[0011] The present invention also provides a composition comprising at least one compound as described above, at least one organic solvent, and / or an organic resin.

[0012] The present invention also provides an organic functional material film comprising at least one of the compounds described above, or prepared using the composition described above.

[0013] The present invention also provides an optoelectronic device comprising a thin film of a compound or organic functional material as described above.

[0014] The present invention also provides 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, (1) the color conversion layer comprises a compound as described above and a light emitter E; (2) the color conversion layer can at least partially absorb the light emitted by the organic light-emitting layer that is transmitted through the second electrode; (3) the emission spectrum of the compound is on the short wavelength side of the absorption spectrum of the light emitter E and at least partially overlaps with it; (4) the half-width at half-maximum (FWHM) of the emission spectrum of the light emitter E is less than or equal to 55 nm.

[0015] Beneficial effects: The compound according to the present invention has high solubility in solvents, especially alcohol solvents, which facilitates the preparation of inks for printing or coating processes, and is environmentally friendly; and has a large extinction coefficient, which facilitates the preparation of thin color converters for display with high color gamut. Detailed Implementation

[0016] This invention can be implemented in many different forms and is not limited to the embodiments described herein. Rather, these embodiments are provided to provide a thorough and complete understanding of the disclosure of this invention.

[0017] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention pertains. The terminology used herein in the description of the invention is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention. The term "and / or" as used herein includes any and all combinations of one or more of the associated listed items.

[0018] In this invention, the main material, matrix material, host material, and matrix material have the same meaning and can be used interchangeably.

[0019] In this invention, organometallic complexes, organometallic coordination compounds, and organometallic coordination compounds have the same meaning and can be used interchangeably.

[0020] In this invention, composition, printing ink, ink, and ink have the same meaning and can be used interchangeably.

[0021] This invention provides a compound comprising a structural unit represented by one of the chemical formulas (1)-(4).

[0022] The symbols and markings used have the following meanings: R1-R4 are substituents, which may be the same as or different from straight-chain alkyl, haloalkyl, alkoxy, or thioalkoxy groups having 1 to 20 carbon atoms; branched or cyclic alkyl, haloalkyl, alkoxy, or thioalkoxy groups having 3 to 20 carbon atoms; silyl groups; substituted ketyl groups having 1 to 20 carbon atoms; alkoxycarbonyl groups having 2 to 20 carbon atoms; aryloxycarbonyl groups having 7 to 20 carbon atoms; cyano groups (-CN); carbamoyl groups (-C(=O)NH2); and haloformyl groups (-C(=O)-X, where X represents a halogen atom). The following groups may contain: a formyl group (-C(=O)-H), an isocyanate group, an isocyanate group, a thiocyanate group or an isothiocyanate group, a hydroxyl group, a NO2 group, a CF3 group, a Cl group, a Br group, a F group, an I group, a crosslinkable group, or a substituted or unsubstituted aromatic or heteroaromatic ring system having 5 to 40 ring atoms, or an aryloxy or heteroaryloxy group having 5 to 40 ring atoms, a disubstituted unit at any position of the above substituents, or a combination of these substituents; n and o are independently selected from natural numbers from 1 to 10; m and p are independently selected from natural numbers from 1 to 12; the compound contains at least one alcohol-soluble or water-soluble group.

[0023] In some embodiments, in R1-R4, one or more groups may form monocyclic or polycyclic aliphatic or aromatic ring systems with each other and / or with the rings bonded to the groups.

[0024] Preferably, R1-R4 may be the same or different from straight-chain alkyl, alkoxy, or thioalkoxy groups having 1 to 10 carbon atoms, or branched or cyclic alkyl, alkoxy, or thioalkoxy groups having 3 to 10 carbon atoms, or silyl groups, or substituted ketone groups having 1 to 10 carbon atoms, or alkoxycarbonyl groups having 2 to 10 carbon atoms, or aryloxycarbonyl groups having 7 to 10 carbon atoms, cyano groups (-CN), carbamoyl groups (-C(=O)NH2), and haloformyl groups (-C(=O)). -X (where X represents a halogen atom), formyl group (-C(=O)-H), isocyanate group, isocyanate group, thiocyanate group or isothiocyanate group, hydroxy group, nitro group, CF3 group, Cl, Br, F, crosslinkable group or substituted or unsubstituted aromatic or heteroaromatic ring system having 5 to 20 ring atoms, or aryloxy or heteroaryloxy group having 5 to 20 ring atoms, or combination of these substituents, wherein one or more substituents may form a monocyclic or polycyclic aliphatic or aromatic ring system with each other and / or with the ring bonded to the substituents.

[0025] In some preferred embodiments, the compound contains at least two alcohol-soluble or water-soluble groups.

[0026] In some other preferred embodiments, the compound comprises at least three alcohol-soluble or water-soluble groups.

[0027] In some preferred embodiments, in chemical formulas (1)-(4), none of R1 / R2 / R3 / R4 forms a monocyclic or polycyclic aliphatic or aromatic ring system with each other and / or with said R1 / R2 / R3 / R4.

[0028] In a preferred embodiment, the compound comprises structural units represented by chemical formulas (1a)-(4a), (4b):

[0029] Wherein: n1 and o1 are independently selected from natural numbers from 1 to 8; m1 and p1 are independently selected from natural numbers from 1 to 10; r is 0 or 1; R1-R4 are defined as described above; Ar1-Ar4, each time they appear, are independently selected from substituted or unsubstituted aromatic or heteroaromatic ring systems having 5 to 40 ring atoms, or aryloxy or heteroaryloxy groups having 5 to 40 ring atoms, or combinations of these systems; L1 and L2, each time they appear, are independently selected from single bonds, aromatic or heteroaromatic groups having 6 to 30 substituted or unsubstituted ring atoms.

[0030] For the purposes of this invention, aromatic ring systems contain 5-10 carbon atoms, and heteroaromatic ring systems contain 1-10 carbon atoms and at least one heteroatom, provided that the total number of carbon atoms and heteroatoms is at least 4. The heteroatom is preferably selected from Si, N, P, O, S, and / or Ge, and particularly preferably from Si, N, P, O, and / or S. For the purposes of this invention, aromatic or heteroaromatic ring systems not only include systems containing aryl or heteroaromatic groups, but also in which multiple aryl or heteroaromatic groups can be interrupted by short non-aromatic units (<10% non-H atoms, preferably less than 5% non-H atoms, such as C, N, or O atoms). Therefore, systems such as 9,9′-spirodifluorene, 9,9-diarylfluorene, triarylamines, and diaryl ethers are also considered aromatic ring systems for this purpose.

[0031] For the purposes of this invention, any H atom on the compound may be further R 1 Group substitution, R 1The definition of R1 as described above is preferred to be: (1) C1-C10 alkyl, particularly preferably 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-ethylhexyl, trifluoromethyl, pentafluoromethyl, 2,2,2-trifluoroethyl, vinyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl, ethynyl, propynyl, butynyl, pentynyl, hexynyl and ocynyl; (2) C1-C10 alkoxy, particularly preferably n-oxyl, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy or 2-methylbutoxy; (3) C2 to C10 aryl or heteroaryl groups, which may be monovalent or divalent depending on the application, and in each case may also be replaced by the aforementioned groups R. 1 The group can be substituted and linked to an aromatic or heteroaromatic ring at any desired position, particularly preferred being: benzene, naphthalene, anthracene, dianaminate, dihydropyrene, chloropyrene, perylene, fluoranthene, butanediol, pentanol, benzo[a]pyrene, furan, benzo[a]furan, isobenzo[a]furan, dibenzo[a]furan, thiophene, benzo[a]thiophene, isobenzo[a]thiophene, thiofluorene, 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, naphthiazole, phenanthridine, pyridinium pyridimazole, pyrazinium pyridimazole, quinoxalineium pyridimazole, oxazole, benzo[a] Oxazole, naphthoxazole, anthraxazole, phenanthrenexazole, isoxazole, 1,2-thiazole, 1,3-thiazole, benzothiazole, pyridazine, benzopyridazine, pyrimidine, benzopyrimidine, quinoxaline, pyrazine, diazanthracene, 1,5-diazanaphthalene, nitrocarbazole, benzocarbline, phenanthrene, 1,2,3-triazole, 1,2,4-triazole, benzotriazole, 1,2,3-oxadiazole, 1,2,4-oxadiazole, 1,2,5-oxadiazole, 1,3,4-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, tetrazolium. 1,2,4,5-Tetraazine, 1,2,3,4-Tetraazine, 1,2,3,5-Tetraazine, purine, pteridine, indene, and benzothiadiazole. For the purposes of this invention, aromatic and heteroaromatic ring systems are considered to include, in particular, biphenylene, terphenylene, fluorene, spirofluorene, dihydrophenanthrene, tetrahydropyrene, and cis or trans indenefluorene, in addition to the aryl and heteroaromatic groups mentioned above.

[0032] In a preferred embodiment, the compounds according to chemical formulas (1a)-(4a), (4b), wherein Ar1-Ar4, whether identical or different, are selected from aromatic or heteroaromatic compounds having 5 to 20 ring atoms in each occurrence; preferably selected from aromatic or heteroaromatic compounds having 5 to 18 ring atoms; more preferably selected from aromatic or heteroaromatic compounds having 5 to 15 ring atoms; most preferably selected from aromatic or heteroaromatic compounds having 5 to 10 ring atoms; they may be unsubstituted or substituted with one or two R atoms. 1 Group substitution. Preferred aryl or heteroaryl groups include benzene, naphthalene, anthracene, phenanthrene, pyridine, dianaphthalene, or thiophene.

[0033] In another preferred embodiment, Ar1-Ar4 are selected from the following structural formulas:

[0034] Where: X3 is CR 6 Or N; Y7 is selected from CR 7 R 8 SiR 9 R 10 NR 6 C (=O), S, or O; R 6 R 7 R 8 R 9 R 10 The definition is as described above for R1.

[0035] Furthermore, Ar1-Ar4 can be independently selected from one or a combination of the following chemical structural formulas, which can be further substituted in any way:

[0036] For the purposes of this invention, in a particularly preferred embodiment, Ar1-Ar4 are selected from benzene, naphthalene, anthracene, phenanthrene, pyridine, dinaphthalene, or thiophene.

[0037] In some preferred embodiments, L1-L2 are independently selected from single bonds or the following groups and combinations thereof:

[0038] Wherein: each time V appears, it is independently selected from CR. 14 Or N; each time Z appears, it is independently selected from NR. 15 CR 16 R 17 O, S, SiR 18 R 19 S = O, SO2; R 14 - R 19Each time it appears, it is independently selected from: hydrogen, D, or a straight-chain alkyl group having 1 to 20 carbon atoms, or a straight-chain alkoxy group having 1 to 20 carbon atoms, or a straight-chain thioalkoxy group having 1 to 20 carbon atoms, or a branched or cyclic alkyl group having 3 to 20 carbon atoms, or a branched or cyclic alkoxy group having 3 to 20 carbon atoms, or a branched or cyclic thioalkoxy or silyl group having 3 to 20 carbon atoms, or a ketone group having 1 to 20 carbon atoms, or an alkoxycarbonyl group having 2 to 20 carbon atoms. A group, or an aryloxycarbonyl, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, CF3, Cl, Br, F, crosslinkable group having 7 to 20 C atoms, or a substituted or unsubstituted aromatic group having 5 to 60 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, or an aryloxy group having 5 to 60 ring atoms, or a heteroaryloxy group having 5 to 60 ring atoms, or a combination of these groups.

[0039] In some preferred embodiments, L1-L2 are independently selected from single bonds and the following groups or combinations thereof:

[0040] Among them, the H atoms on the ring can be further replaced.

[0041] In some preferred embodiments, the structural units according to chemical formulas (1)-(4), wherein R1-R4, when appearing multiple times, may contain the following structural units or combinations thereof, either identically or differently:

[0042] Where n2 is 1, 2, 3, or 4.

[0043] In a preferred embodiment, the compound according to the invention, wherein the alcohol-soluble or water-soluble group is selected from groups such as alcohols, aldehydes, acids, crown ethers, polyethers, and primary amines.

[0044] Preferably, the alcohol-soluble or water-soluble group is selected from the following structures:

[0045] Where: R 31 -R 37It can be a straight-chain alkyl, alkoxy, or thioalkoxy group having 1 to 20 carbon atoms, or a branched or cyclic alkyl, alkoxy, or thioalkoxy group having 3 to 20 carbon atoms, or a silyl group, or a substituted ketyl group having 1 to 20 carbon atoms, or an alkoxycarbonyl group having 2 to 20 carbon atoms, or an aryloxycarbonyl group having 7 to 20 carbon atoms, a cyano group (-CN), a carbamoyl group (-C(=O)NH2), a haloformyl group (-C(=O)-X where X represents a halogen atom), or a formyl group. Groups (-C(=O)-H), isocyanate groups, isocyanate groups, thiocyanate groups or isothiocyanate groups, hydroxy groups, nitro groups, CF3 groups, Cl, Br, F, crosslinkable groups, or substituted or unsubstituted aromatic or heteroaromatic ring systems having 5 to 40 ring atoms, or aryloxy or heteroaryloxy groups having 5 to 40 ring atoms, or combinations of these groups, wherein one or more groups may form monocyclic or polycyclic aliphatic or aromatic ring systems with each other and / or with the rings bonded to said groups; dashed lines indicate bonds; t is an integer greater than 0.

[0046] Furthermore, in this invention, a single H atom or CH2 group can be replaced by the aforementioned groups or group R, where R is selected from alkyl groups having 1 to 40 C atoms, preferably selected from the following groups: methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclobutyl, methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, n-hexyl, cyclohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, ethylhexyl, trifluoromethyl Alkyl, pentafluoroethyl, trifluoroethyl, vinyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl, ethynyl, propynyl, butynyl, penynyl, hexynyl, and ocynyl; alkoxy groups having 1 to 40 carbon atoms, such as methoxy, trifluoromethoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, or methylbutoxy.

[0047] In some embodiments, the compound according to the invention, wherein SP 3 The total amount of hybrid groups should not exceed 50% of the total molecular weight, preferably not more than 30%, and most preferably not more than 20%. Fewer SPs 3 The presence of hybrid groups can effectively ensure the thermal stability of the compound, thereby ensuring the stability of the device.

[0048] In other preferred embodiments, to improve solubility and / or film-forming properties, the compound according to the invention, wherein SP 3 The total amount of hybrid groups exceeds 20% of the total molecular weight, preferably exceeds 30%, more preferably exceeds 40%, and most preferably exceeds 50%.

[0049] In some preferred embodiments, the compound has a high extinction coefficient. The extinction coefficient, also known as the molar extinction coefficient, refers to the absorbance coefficient at a concentration of 1 mol / L, denoted by the symbol ε, and its unit is Lmol. -1 cm -1 The preferred extinction coefficient is: ε ≥ 1 10 3 More preferably: ε ≥ 1 10 4 Especially preferred: ε≥ 5 10 4 The optimal choice is: ε ≥ 1 10 5 Preferably, the extinction coefficient refers to the extinction coefficient at the wavelength corresponding to the absorption peak.

[0050] In other preferred embodiments, the compound exhibits high fluorescence luminescence efficiency, specifically fluorescence quantum efficiency (PLQY). 60% is better 65%, even better 70%, even better 80%, ideally 90%.

[0051] Examples of suitable compounds according to the invention are given below, but are not limited to:

[0052] The present invention also relates to a method for synthesizing compounds according to chemical formulas (1)-(4), wherein a reaction is carried out using a starting material containing an active group. These active starting materials contain at least one leaving group, such as bromine, iodine, boric acid, or borate ester. Suitable reactions for forming CC linkages are well known to those skilled in the art and described in the literature, and particularly suitable and preferred coupling reactions are the SUZUKI, STILLE, BUCHWALD-HARTWIG, and HECK coupling reactions.

[0053] This invention also provides a mixture comprising at least one compound as described above and another functional material, wherein the other functional material may be an organic functional material, selectable from hole injection or transport materials (HIM / HTM), hole blocking materials (HBM), electron injection or transport materials (EIM / ETM), electron blocking materials (EBM), organic matrix 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, the entire contents of which are hereby incorporated herein by reference.

[0054] In a preferred embodiment, the mixture comprises a compound according to the invention and a luminescent material. The compound according to the invention may be used as the main 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%.

[0055] In a preferred embodiment, the luminescent material is selected from organic phosphors.

[0056] The following is a detailed description of fluorescent emitters (also known as singlet emitters).

[0057] 1. Singlet Emitter

[0058] Singlet luminescent organisms often have a long conjugated π-electron system. To date, there have been many examples, such as styreneamines and their derivatives disclosed in JP2913116B and WO2001021729A1, and indofluorenes and their derivatives disclosed in WO2008 / 006449 and WO2007 / 140847.

[0059] In a preferred embodiment, the singlet emitter may be selected from monostyreneamine, distyreneamine, tristyreneamine, tetrastyreneamine, styrenephosphine, styrene ether, and aromatic amine.

[0060] A monostyrene amine refers to a compound comprising an unsubstituted or substituted styrene group and at least one amine, preferably an aromatic amine. A distyrene amine refers to a compound comprising two unsubstituted or substituted styrene groups and at least one amine, preferably an aromatic amine. A tristyrene amine refers to a compound comprising three unsubstituted or substituted styrene groups and at least one amine, preferably an aromatic amine. A tetrastyrene amine refers to a compound comprising four unsubstituted or substituted styrene groups and at least one amine, preferably an aromatic amine. A preferred styrene is stilbene, which may be further substituted. The definitions of the corresponding phosphines and ethers are similar to those for amines. An aryl amine or aromatic amine refers to a compound comprising three unsubstituted or substituted aromatic or heterocyclic systems directly linked 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 anthracene amines, aromatic anthracene diamines, aromatic pyrene amines, aromatic pyrene diamines, aromatic drosamines, and aromatic drosamines. An aromatic anthracene amine refers to a compound in which one diarylamine group is directly attached to anthracene, preferably at the 9-position. An aromatic anthracene diamine refers to a compound in which two diarylamine groups are directly attached to anthracene, preferably at the 9 or 10 positions. Aromatic pyrene amines, aromatic pyrene diamines, aromatic trehalamines, and aromatic trehaline diamines are similarly defined, wherein the diarylamine group is preferably attached to the 1 or 1,6 position of pyrene.

[0061] Examples, and preferred examples, of singlet luminescent materials based on ethyleneamine and aromatic amines can be found in the following patent documents: WO 2006 / 000388, WO 2006 / 058737, WO 2006 / 000389, WO 2007 / 065549, WO2007 / 115610, US 7250532 B2, DE 102005058557 A1, CN 1583691 A, JP 08053397 A, US 6251531 B1, US 2006 / 210830 A, EP 1957606 A1 and US 2008 / 0113101 A1. The entire contents of the patent documents listed above are hereby incorporated herein by reference.

[0062] Examples of singlet luminescent organisms based on isostyrene and its derivatives include US 5121029.

[0063] Further preferred singlet luminescent materials may be indene-fluorene-amine and indene-fluorene-diamine, as disclosed in WO 2006 / 122630, benzo[a]indene-fluorene-amine and benzo[a]indene-fluorene-diamine, as disclosed in WO 2008 / 006449, and dibenzo[a]indene-fluorene-amine and dibenzo[a]indene-fluorene-diamine, as disclosed in WO2007 / 140847.

[0064] Other materials that can be used as singlet luminescent materials are polycyclic aromatic hydrocarbons, particularly derivatives of the following compounds: anthracene such as 9,10-bis(2-naphthoanthracene), naphthalene, tetraphenyl, xanthracene, phenanthrene, pyrene (such as 2,5,8,11-tetra-t-butylperylene), indene, phenylene such as (4,4'-bis(9-ethyl-3-carbazovinyl)-1,1'-biphenyl), diindene, decacyclic, hexabenzobenzene, fluorene, spirodifluorene, arylpyrene (such as US20060222886), aromatic vinylidene (such as US5121029, US5130603), cyclopentadiene such as tetraphenylcyclopentadiene, Rubrene, coumarin, rhodamine, quinacridone, pyran, such as 4-(dicyanomethylene)-6-(4-p-dimethylaminostyryl-2-methyl)-4H-pyran (DCM), thioran, bis(acrazinyl)imine boron compound (US2007 / 0092753 A1), bis(acrazinyl)methylene compound, carbostyryl compound, oxazinone, benzoxazole, benzothiazole, benzimidazole, and pyrrolopyrrole dione. Some singlet luminescent materials can be found in the following patent documents: US 20070252517 A1, US 4769292, US 6020078, US 2007 / 0252517 A1, US 2007 / 0252517 A1. The entire contents of the above-listed patent documents are hereby incorporated herein by reference.

[0065] Below are some examples of suitable singlet luminescent organisms:

[0066] In a particularly preferred embodiment, the mixture comprises a compound (main material H) according to the present invention and a luminescent body E, wherein: 1) the emission spectrum of the compound (main material H) is on the shorter wavelength side of the absorption spectrum of the luminescent body E and at least partially overlaps with it; 2) the full width at half maximum (FWHM) of the emission spectrum of the luminescent body E is less than or equal to 55 nm.

[0067] The present invention also provides a composition comprising at least one compound described herein, at least one organic solvent, and / or an organic resin.

[0068] In a preferred embodiment, the composition further comprises a light emitter E, 1) the emission spectrum of the compound is on the shorter wavelength side of the absorption spectrum of the light emitter E and at least partially overlaps with it; 2) the half-width at half maximum (FWHM) of the emission spectrum of the light emitter E is less than or equal to 55 nm.

[0069] In a preferred embodiment, the composition comprises one organic resin; in other embodiments, it comprises two or more organic resins; and in still other embodiments, it comprises three or more organic resins.

[0070] For the purposes of this invention, the organic resin refers to a resin prepolymer or a resin formed after crosslinking or curing.

[0071] Organic resins suitable for use in this invention include, but are not limited to: polystyrene, polyacrylate, polymethacrylate, polycarbonate, polyurethane, polyvinylpyrrolidone, polyvinyl acetate, polyvinyl chloride, polybutene, 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.

[0072] Furthermore, the 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, ethylene ester derivatives, ethylene ether derivatives, maleimide derivatives, and conjugated diene derivatives.

[0073] Examples of styrene derivatives include: alkyl styrene, such as α-methylstyrene, o-, m-, and p-methylstyrene, p-butylstyrene, especially p-tert-butylstyrene, and alkoxystyrene, such as p-methoxystyrene, p-butoxystyrene, and p-tert-butoxystyrene.

[0074] 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-hydroxybutyl acrylate, 2-hydroxybutyl methacrylate, 3-hydroxybutyl methacrylate, 3-hydroxybutyl methacrylate, 4-hydroxybutyl methacrylate, 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, methoxydiethylene glycol acrylate, methoxydiethylene glycol methacrylate, methoxytriethylene glycol acrylate, methoxytriethylene glycol methacrylate, methoxypropylene glycol acrylate, methoxypropylene glycol methacrylate, methoxydipropylene glycol methacrylate, isobornyl acrylate, isobornyl methacrylate, dicyclopentadienyl acrylate, dicyclopentadienyl methacrylate, (meth)adamantane acrylate, (meth)norbornyl acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-hydroxy-3-phenoxypropyl methacrylate, glyceryl monoacrylate and glyceryl monomethacrylate; 2-aminoethyl acrylate, 2-aminoethyl methacrylate, 2-dimethylaminoethyl acrylate, 2-dimethylaminoethyl methacrylate, N N-Dimethylaminoethyl (meth)acrylic acid, N,N-Diethylaminoethyl (meth)acrylic acid ester, 2-aminopropyl acrylate, 2-aminopropyl methacrylate, 2-dimethylaminopropyl acrylate, 2-dimethylaminopropyl methacrylate, 3-aminopropyl acrylate, 3-aminopropyl methacrylate, N,N-Dimethyl-1,3-propanediamine (meth)acrylate benzyl acrylate, 3-dimethylaminopropyl acrylate and 3-dimethylaminopropyl methacrylate; glycidyl acrylate and glycidyl methacrylate.

[0075] Examples of acrylonitrile derivatives include acrylonitrile, methacrylonitrile, α-chloroacrylonitrile, and vinylidene cyanide.

[0076] Examples of acrylamide derivatives include: acrylamide, methacrylamide, α-chloroacrylamide, N-2-hydroxyethylacrylamide, and N-2-hydroxyethylmethylacrylamide.

[0077] Examples of vinyl ester derivatives include vinyl acetate, vinyl propionate, vinyl butyrate, and vinyl benzoate.

[0078] Examples of vinyl ether derivatives include vinyl methyl ether, vinyl ethyl ether, and allyl glycidyl ether.

[0079] Examples of maleimide derivatives include maleimide, benzyl maleimide, N-phenyl maleimide, and N-cyclohexyl maleimide.

[0080] Examples of conjugated diene derivatives include 1,3-butadiene, isoprene, and chloroprene.

[0081] The homopolymers or copolymers described herein can be prepared by, for example, free radical polymerization, cationic polymerization, anionic polymerization, or organometallic catalytic polymerization (e.g., Ziegler-Natta catalysis). The polymerization process can be suspension polymerization, emulsion polymerization, solution polymerization, or bulk polymerization.

[0082] The organic resin typically has an average molar mass Mn (determined by GPC) of 10,000-1,000,000 g / mol, preferably 20,000-750,000 g / mol, and more preferably 30,000-500,000 g / mol.

[0083] In some preferred embodiments, the organic resin is a thermosetting resin or a UV-curable resin. In some embodiments, the organic resin is cured using a method that facilitates roll-to-roll processing.

[0084] Thermosetting resins require curing, during which they undergo an irreversible molecular cross-linking process, making the resin inmeltable. In some embodiments, the thermosetting resin is an epoxy resin, phenolic resin, vinyl resin, melamine resin, urea-formaldehyde resin, unsaturated polyester resin, polyurethane resin, allyl resin, acrylic resin, polyamide resin, polyamide-imide resin, phenolic amine condensation resin, urea-melamine condensation resin, or a combination thereof.

[0085] In some embodiments, the thermosetting resin is an epoxy resin. Epoxy resins are easy to cure and do not release volatiles or generate byproducts from a wide range of chemicals. Epoxy resins are also compatible with most substrates and tend to easily wet surfaces. See Boyle, MA et al., “Epoxy Resins”, Composites, Vol. 21, ASM Handbook, pages 78-89 (2001).

[0086] 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)).

[0087] In a preferred embodiment, the composition comprises one organic solvent; in other embodiments, it comprises two or more organic solvents; and in still other embodiments, it comprises three or more organic solvents.

[0088] In a preferred embodiment, the composition according to the invention is a solution.

[0089] In another preferred embodiment, the composition according to the invention is a suspension.

[0090] The compositions in the embodiments of the present invention may include 0.01 to 20 wt% of the compound, preferably 0.1 to 20 wt%, more preferably 0.2 to 20 wt%, and most preferably 1 to 15 wt% of the compound.

[0091] According to the composition of the present invention, a color conversion layer can be formed using methods such as inkjet printing, transfer printing, and photolithography. In this case, the color conversion material of the present invention needs to be dissolved alone or together with other materials in an organic solvent to form ink. The mass concentration of the color conversion material of the present invention in the ink is not less than 0.1 wt%. The color conversion capability of the color conversion layer can be improved by adjusting the concentration of the color conversion material in the ink and the thickness of the color conversion layer. Generally speaking, the higher the concentration of the color conversion material or the thicker the layer, the higher the color conversion rate of the color conversion layer.

[0092] Other materials that may be added to the ink include, but are not limited to, the following: polyethylene, polypropylene, polystyrene, polycarbonate, polyacrylate, polyvinylpyrrolidone, polyvinyl alcohol, polyvinyl acetate, polyethylene glycol, polysiloxane, polyacrylonitrile, polyvinyl chloride, polyvinylidene chloride, polyethylene terephthalate, polybutylene terephthalate, polyvinyl butyrate, polyamide, polyoxymethylene, polyimide, polyetheretherketone, polysulfone, polyaryl ether, polyarylamide, cellulose, modified cellulose, cellulose acetate, cellulose nitrate, or mixtures thereof.

[0093] In some preferred embodiments, the organic solvent is selected from inorganic ester compounds such as esters, aromatic ketones or aromatic ethers, aliphatic ketones or aliphatic ethers, or borate esters or phosphate esters, or mixtures of two or more organic solvents.

[0094] In other embodiments, suitable and preferred organic solvents are aliphatic, alicyclic or aromatic, amines, thiols, amides, nitriles, esters, ethers, polyethers, alcohols, diols or polyols.

[0095] In other embodiments, the alcohol represents an appropriate class of organic solvents. Preferred alcohols include alkylcyclohexanols, particularly methylated aliphatic alcohols, naphthols, etc.

[0096] Other suitable examples of alcohol solvents include: dodecanol, phenyltridecyl alcohol, benzyl alcohol, ethylene glycol, ethylene glycol methyl ether, glycerol, propylene glycol, propylene glycol ethyl ether, etc.

[0097] The organic solvent can be used alone or as a mixture of two or more organic solvents.

[0098] In some embodiments, the composition according to the invention comprises one compound as described above and at least one organic solvent, and may further comprise another organic solvent, examples of which include (but are not limited to): methanol, ethanol, 2-methoxyethanol, dichloromethane, trichloromethane, 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, tetrahydronaphthalene, naphthane, indene, and / or mixtures thereof.

[0099] In some preferred embodiments, according to a composition of the present invention, the other organic solvent is selected from aromatic or heteroaromatic compounds, esters, aromatic ketones or aromatic ethers, aliphatic ketones or aliphatic ethers, alicyclic or olefinic compounds, or inorganic esters such as borate esters or phosphate esters, or mixtures of two or more solvents.

[0100] Examples of aromatic or heteroaromatic solvents according to the present invention include, but are not limited to: 1-tetrahydronaphthylone, 3-phenoxytoluene, acetophenone, 1-methoxynaphthyl, p-diisopropylbenzene, pentanbenzene, tetrahydronaphthyl, cyclohexylbenzene, chloronaphthyl, 1,4-dimethylnaphthyl, 3-isopropylbiphenyl, p-methylisopropylbenzene, dipentanene, o-diethylbenzene, m-diethylbenzene, p-diethylbenzene, 1,2,3,4-tetramethylbenzene, 1,2,3,5-tetramethylbenzene, 1 2,4,5-Tetramethylbenzene, Butylbenzene, Dodecylbenzene, 1-Methylnaphthalene, 1,2,4-Trichlorobenzene, 1,3-Dipropoxybenzene, 4,4-Difluorodiphenylmethane, Diphenyl ether, 1,2-Dimethoxy-4-(1-Propylene)benzene, Diphenylmethane, 2-Phenyridine, 3-Phenyridine, 2-Phenoxymethyl ether, 2-Phenoxytetrahydrofuran, Ethyl-2-Naphthyl ether, N-Methyldiphenylamine, 4-Isopropylbiphenyl Dichlorodiphenylmethane, 4-(3-phenylpropyl)pyridine, benzyl benzoate, 1,1-bis(3,4-dimethylphenyl)ethane, 2-isopropylnaphthalene, dibenzyl ether, etc.

[0101] In other embodiments, a suitable and preferred alternative organic solvent is an aliphatic, alicyclic, or aromatic amine, thiol, amide, nitrile, ester, ether, or polyether.

[0102] The other organic solvent may be a cycloalkanes, such as decahydronaphthalene.

[0103] In some other preferred embodiments, a composition according to the invention contains at least 50 wt% of an alcohol solvent; preferably at least 80 wt% of an alcohol solvent; particularly preferably at least 90 wt% of an alcohol solvent.

[0104] In some preferred embodiments, organic solvents particularly suitable for the present invention are solvents with Hansen solubility parameters within the following ranges: δ d (Dispersion force) in the range of 17.0~23.2 MPa 1 / 2 The range, especially in the 18.5~21.0 MPa range. 1 / 2 Scope; δ p (Polar force) is between 0.2 and 12.5 MPa. 1 / 2 The range, especially 2.0~6.0 MPa 1 / 2 Scope; δ h (Hydrogen bond strength) ranges from 0.9 to 14.2 MPa 1 / 2 The range, especially 2.0~6.0 MPa 1 / 2 The range.

[0105] In the compositions of the present invention, the boiling point of the organic solvent is taken into consideration when selecting it. In this 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 of the inkjet printhead. The organic solvent can evaporate from the solvent system to form a thin film containing functional materials.

[0106] In some preferred embodiments, a composition according to the invention, 1) Its viscosity at 25°C is in the range of 1 cPs to 100 cPs, and / or 2) Its surface tension at 25℃ ranges from 19 dyne / cm to 50 dyne / cm.

[0107] In the compositions according to the present invention, the surface tension parameter of the organic solvent must be considered when selecting it. Suitable ink surface tension parameters are appropriate for specific substrates and specific printing methods. For example, for inkjet printing, in a preferred embodiment, the surface tension of the organic solvent at 25°C is approximately in the range of 19 dyne / cm to 50 dyne / cm; more preferably in the range of 22 dyne / cm to 35 dyne / cm; and most preferably in the range of 25 dyne / cm to 33 dyne / cm.

[0108] In a preferred embodiment, the ink according to the invention has a surface tension of about 19 dyne / cm to 50 dyne / cm at 25°C; more preferably, it is in the range of 22 dyne / cm to 35 dyne / cm; and most preferably, it is in the range of 25 dyne / cm to 33 dyne / cm.

[0109] In the compositions according to the present invention, the organic solvent is selected with consideration for the viscosity parameters of the ink. Viscosity can be adjusted by various methods, such as by selecting a suitable organic solvent and the concentration of functional materials 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 1.5 to 20 cps. Viscosity here refers to 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. The compositions thus formulated are particularly suitable for inkjet printing.

[0110] In a preferred embodiment, the composition according to the invention has a viscosity at 25°C ranging from about 1 cps to 100 cps; more preferably from 1 cps to 50 cps; and most preferably from 1.5 cps to 20 cps.

[0111] Inks obtained from organic solvents that meet the above-mentioned boiling point, surface tension, and viscosity parameters can form functional material films with uniform thickness and compositional properties.

[0112] Salt compounds are difficult to purify and easily introduce impurities, affecting photoelectric performance. For the purposes of this invention, in certain preferred embodiments, the above-described compositions or mixtures do not contain any salt compounds, and preferably do not contain any organic acid salts formed from organic acids and metals. For cost considerations, this invention preferentially excludes organic acid salts containing transition metals and lanthanides.

[0113] The present invention further provides an organic functional material film comprising an organic compound or mixture as described above, or prepared using a composition as described above. Preferably, the organic functional material film is prepared using a composition as described above.

[0114] The present invention also provides a method for preparing the aforementioned organic functional material thin film, comprising the following steps: 1) Prepare a composition according to the present invention; 2) The composition is coated onto a substrate to form a thin film by printing or coating methods, wherein the printing or coating methods are 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, spraying, brush coating or pad printing, slot extrusion coating; 3) Heat the obtained film at at least 50°C, and optionally add ultraviolet light to cause a cross-linking reaction and cure the film.

[0115] The thickness of the organic functional material film is generally 50nm-200nm. m, preferably 100nm-150 m, better to be 500nm-100 m, better to be 1 m-50 m, preferably 1 m-20 m.

[0116] In another preferred embodiment, the organic functional material film has a thickness between 20 nm and 20 nm. m, preferably less than 15 m, preferably less than 10 m, or better yet, less than 8 m, preferably less than 6 m, preferably less than 4 m should ideally be less than 2. m.

[0117] Another object of the present invention is to provide the application of the above-mentioned compounds and mixtures thereof in optoelectronic devices.

[0118] 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.

[0119] Furthermore, the present invention provides an optoelectronic device comprising a thin film of the aforementioned organic compound or mixture or organic functional material.

[0120] 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.

[0121] 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, a perovskite light-emitting diode (PeLED), and a quantum dot light-emitting diode (QD-LED), wherein a functional layer comprises one of the aforementioned organic compounds or mixtures or organic functional material films. The functional layer may 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).

[0122] In a preferred embodiment, the optoelectronic device is an electroluminescent device comprising two electrodes, with the functional layer located on the same side of the two electrodes.

[0123] In another preferred embodiment, the optoelectronic device includes a light-emitting unit and a color conversion layer, wherein the color conversion layer comprises a thin film of the aforementioned organic compound or mixture or organic functional material.

[0124] In some preferred embodiments, the light-emitting unit is selected from solid-state light-emitting devices. The solid-state light-emitting devices are preferably selected from LEDs, organic light-emitting diodes (OLEDs), organic light-emitting cells (OLEECs), organic light-emitting field-effect transistors, perovskite light-emitting diodes (PeLEDs), quantum dot light-emitting diodes (QD-LEDs), and nanorod LEDs (see DOI: 10.1038 / srep28312).

[0125] In a preferred embodiment, the light-emitting unit emits blue light, which is converted into green light by a color conversion layer.

[0126] In another preferred embodiment, the light-emitting unit emits green light, which is converted into yellow or red light by a color conversion layer.

[0127] The present invention further relates to a display comprising at least three types of pixels: red, green, and blue. A blue pixel encloses a blue light-emitting unit, and a red-green pixel includes a blue light-emitting unit and a corresponding red-green color conversion layer.

[0128] The present invention further relates to an organic electroluminescent 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 outermost encapsulation layer, wherein the second electrode is at least partially transparent; (1) the color conversion layer comprises a compound according to the present invention and a light emitter E; (2) the color conversion layer is capable of absorbing 90% or more of the light emitted by the organic light-emitting layer that is transmitted through the second electrode; and (3) the emission spectrum of the organic compound is on the shorter wavelength side of the absorption spectrum of the light emitter E, and at least partially overlaps with it. Preferably, the full width at half maximum (FWHM) of the emission spectrum of the light emitter E is less than or equal to 55 nm.

[0129] The compound and the luminescent agent E, and their preferred embodiments, are as described above.

[0130] 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 that is transmitted through the second electrode.

[0131] 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 that is transmitted through the second electrode.

[0132] In some embodiments, the thickness of the color conversion layer is 100nm-5nm. Between 150nm and 4nm, preferably between 150nm and 4nm. Between 100nm and 300nm, preferably between 100nm and 300nm. Between m, preferably 200nm-2 Between m.

[0133] 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 preferred, the organic electroluminescent device is a top-emission OLED.

[0134] The substrate can be opaque or transparent. A transparent substrate can be used to fabricate a transparent light-emitting device. See, for example, Bulovic et al., Nature 1996, 380, p29, and Gu et al., Appl. Phys. Lett. 1996, 68, p2606. The substrate can be rigid or flexible. The substrate can be plastic, metal, semiconductor wafer, or glass. Preferably, the substrate has a smooth surface. A substrate without surface defects is particularly desirable. In a preferred embodiment, the substrate is flexible and can be a polymer film or plastic with a glass transition temperature (Tg) of 150°C or higher, preferably 200°C or higher, more preferably 250°C or higher, and most preferably 300°C or higher. Examples of suitable flexible substrates include polyethylene terephthalate (PET) and polyethylene glycol (2,6-naphthalene) (PEN).

[0135] The anode may comprise a conductive metal or metal oxide, or a conductive polymer. Holes can be readily injected 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 level or valence band level of the light emitter 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), etc. Other suitable anode materials are known and can be readily selected by those skilled 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), etc. In some embodiments, the anode is patterned. Patterned ITO conductive substrates are commercially available and can be used to fabricate devices according to the present invention.

[0136] The cathode may comprise a conductive metal or metal oxide. Electrons can be readily injected into the EIL or ETL or directly into the light-emitting layer. In a preferred embodiment, the absolute value of the difference between the work function of the cathode and the LUMO level or conduction band level of the luminescent material 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 suitable for use as cathodes in OLEDs can be used as cathode materials for the devices of this invention. Examples of cathode materials include, but are not limited to: Al, Au, Ag, Ca, Ba, Mg, LiF / Al, MgAg alloy, BaF2 / Al, Cu, Fe, Co, Ni, Mn, Pd, Pt, ITO, etc. 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), etc. In a preferred embodiment, the cathode has a transmittance in the range of 400 nm to 680 nm. 40% is better 45%, even better 50%, preferably 60%. Typically, 10-20 nm Mg:Ag alloys can be used to make transparent cathodes, and the Mg:Ag ratio can range from 2:8 to 0.5:9.5.

[0137] In the organic electroluminescent device, the light-emitting layer preferably comprises a blue phosphor host and a blue phosphor guest. In another preferred embodiment, the light-emitting layer comprises a blue phosphor host and a blue phosphor guest. The OLED may also 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 which are hereby incorporated herein by reference.

[0138] Furthermore, the organic electroluminescent device also includes a cathode capping layer (CPL).

[0139] In a preferred embodiment, the CPL is located between the second electrode and the color conversion layer.

[0140] In another preferred embodiment, the CPL is located above the color conversion layer.

[0141] Materials used in CPL generally need to have a high refractive index n, such as n 1.95@460nm, n 1.90@520nm, n 1.85@620nm. Examples of its use in CPL materials include:

[0142] Further examples of 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.

[0143] In a preferred embodiment, the color conversion layer comprises one of the CPL materials described above. In a particularly preferred embodiment, the color conversion layer is co-deposited from one of the CPL materials described above, the compound described above (host material H), and the light emitter E. In some embodiments, the mass ratio of the compound described above (host material H) is 50%-20%, and the mass ratio of the light emitter E is 10%-15%.

[0144] Preferably, in the above-described organic electroluminescent device, the encapsulation layer is a thin-film encapsulation (TFE).

[0145] The present invention further relates to a display panel wherein at least one pixel comprises the aforementioned organic electroluminescent device.

[0146] The present invention will now be described 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 inventive concept, those skilled in the art should realize that any 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.

[0147] Compound Synthesis Examples

[0148] Example 1: Synthesis of Compound 1

[0149] Synthesis of Compound 1: The classic SUZUKI reaction was used for synthesis. The specific synthetic steps are as follows: Under nitrogen protection, 10.00 mmol of intermediate 1-1, 20.08 mmol of intermediate 1-2 and 20.00 mmol of potassium carbonate were added sequentially to a 500 mL three-necked flask. 200 mL of toluene was added, and 0.3 mol of catalyst Pd(PPh3)4 was added under stirring. The mixture was heated to reflux and the reaction was monitored by TLC. After the reaction was complete, the reaction solution was cooled to room temperature, washed three times with water and three times with dichloromethane, the organic phases were combined, dried with anhydrous Na2SO4, filtered, and the solvent was evaporated to obtain the crude product. The crude product was purified by rapid column chromatography to obtain 7.58 mmol of product, which was dried for later use. Yield: 75.8%, MS (ASAP) = 460.2.

[0150] Example 2: Synthesis of Compound 2

[0151] Synthesis of Compound 2: The synthesis method was similar to that of Compound 1, using the classic SUZUKI reaction, with a yield of 80.2%. The product was dried under vacuum. MS (ASAP) = 436.2.

[0152] Example 3: Synthesis of Compound 3

[0153] Synthesis of Compound 3: The synthesis method was similar to that of Compound 1, using the classic SUZUKI reaction, with a yield of 78.1%. The product was dried under vacuum. MS (ASAP) = 434.2.

[0154] Example 4: Synthesis of Compound 4

[0155] Synthesis of compounds 4-3: The synthesis method was similar to that of compound 1, using the classic SUZUKI reaction, with a yield of 78.9%. Vacuum drying was performed. MS (ASAP) = 520.2.

[0156] Synthesis of Compound 4: The classic alkaline hydrolysis method was used. The specific synthetic steps are as follows: 10.00 mmol of intermediate 4-3 and 12.00 mmol of sodium hydroxide were added sequentially to a 500 mL three-necked flask. 200 mL of tetrahydrofuran was added, and the mixture was heated to reflux. The reaction was monitored by TLC. After the reaction was complete, the reaction solution was cooled to room temperature, washed three times with water and three times with chloroform, the organic phases were combined, dried with anhydrous Na2SO4, filtered, and the solvent was evaporated to obtain the crude product. The crude product was purified by rapid column chromatography to obtain 9.58 mmol of the product. After drying, the yield was 95.8%, and the MS (ASAP) value was 492.1.

[0157] Example 5: Synthesis of Compound 5

[0158] Synthesis of Compound 5: The synthesis method was similar to that of Compound 1, using the classic SUZUKI reaction, with a yield of 84.6%. The product was dried under vacuum. MS (ASAP) = 988.5.

[0159] Example 6: Synthesis of Compound 6

[0160] Synthesis of Compound 6: The synthesis method was similar to that of Compound 1, using the classic SUZUKI reaction, with a yield of 75.4%. The product was dried under vacuum. MS (ASAP) = 616.3.

[0161] Example 7: Synthesis of Compound 7

[0162] Synthesis of Compound 7: The synthesis method was similar to that of Compound 1, using the classic SUZUKI reaction, with a yield of 70.1%. The product was dried under vacuum. MS (ASAP) = 620.2.

[0163] Example 8: Synthesis of Compound 8

[0164] Synthesis of compound 8-3: The synthesis method was similar to that of compound 1, using the classic SUZUKI reaction, yield: 72.2%. Vacuum drying. MS (ASAP) = 738.3.

[0165] Synthesis of Compound 8: The synthesis method was similar to that of Compound 4, employing a classic alkaline hydrolysis reaction. Yield: 92.5%. Vacuum drying. MS (ASAP) = 682.2.

[0166] Example 9: Synthesis of Compound 9

[0167] Synthesis of Compound 9-3: The synthesis method was similar to that of Compound 1, using the classic SUZUKI reaction, with a yield of 75.3%. The product was dried under vacuum. MS (ASAP) = 554.3.

[0168] Synthesis of Compound 9: The synthesis method was similar to that of Compound 4, employing a classic alkaline hydrolysis reaction. Yield: 97.0%. Vacuum drying. MS (ASAP) = 626.2.

[0169] Example 10: Synthesis of Compound 10

[0170] Synthesis of compound 10-3: The synthesis method was similar to that of compound 1, using the classic SUZUKI reaction, with a yield of 79.8%. The product was dried under vacuum. MS (ASAP) = 496.2.

[0171] Synthesis of Compound 10: The synthesis method was similar to that of Compound 4, employing a classic alkaline hydrolysis reaction. Yield: 94.5%. Vacuum drying. MS (ASAP) = 468.1.

[0172] Example 11: Synthesis of Compound 11

[0173] Synthesis of compound 11-3: The synthesis method was similar to that of compound 1, using the classic SUZUKI reaction, with a yield of 79.8%. The product was dried under vacuum. MS (ASAP) = 896.3.

[0174] Synthesis of Compound 11: The synthesis method was similar to that of Compound 4, employing a classic alkaline hydrolysis reaction. Yield: 94.5%. Vacuum drying. MS (ASAP) = 840.2.

[0175] Example 12: Synthesis of Compound 12

[0176] Synthesis of Compound 12: The synthesis method was similar to that of Compound 1, employing the classic Suzuki reaction. Yield: 80.4%. Vacuum drying. MS (ASAP) = 720.3. Example 13: Synthesis of Compound 13

[0177] Synthesis of Compound 13: The synthesis method was similar to that of Compound 1, using the classic SUZUKI reaction, with a yield of 48.9%. The product was dried under vacuum. MS (ASAP) = 528.2.

[0178] Example 14: Synthesis of Compound 14

[0179] Synthesis of compound 14-3: The classic Hartwig reaction was used. The specific synthetic steps are as follows: Under nitrogen protection, 10.00 mmol of intermediate 9-1, 20.08 mmol of intermediate 14-2, and 20.00 mmol of potassium carbonate were added sequentially to a 500 mL three-necked flask. 200 mL of toluene was added, and 0.3 mol of catalyst Pd(OAc)2 and 0.30 mmol of tri-tert-butylphosphine were added under stirring. The mixture was heated to reflux and the reaction was monitored by TLC. After the reaction was complete, the reaction solution was cooled to room temperature, washed three times with water and three times with dichloromethane, the organic phases were combined, dried with anhydrous Na2SO4, filtered, and the solvent was evaporated to obtain the crude product. The crude product was purified by rapid column chromatography to obtain 6.64 mmol of product, which was dried for later use. Yield: 66.4%, MS (ASAP) = 852.3.

[0180] Synthesis of Compound 14: The synthesis method was similar to that of Compound 4, employing a classic alkaline hydrolysis reaction. Yield: 95.2%. Vacuum drying. MS (ASAP) = 796.2.

[0181] Example 15: Synthesis of Compound 15

[0182] Synthesis of compound 15-3: The synthesis method was similar to that of compound 14-3, using the classic Hartwig reaction, with a yield of 59.8%. The product was dried under vacuum for later use. MS (ASAP) = 1334.4.

[0183] Synthesis of Compound 15: The synthesis method was similar to that of Compound 4, employing a classic alkaline hydrolysis reaction. Yield: 94.7%. Vacuum drying. MS (ASAP) = 1222.3.

[0184] Example 16: Synthesis of Compound 16

[0185] Synthesis of compound 16-3: The synthesis method was similar to that of compound 14-3, using the classic Hartwig reaction, with a yield of 55.5%. The product was dried under vacuum for later use. MS (ASAP) = 794.3.

[0186] Synthesis of Compound 16: The synthesis method was similar to that of Compound 4, employing a classic alkaline hydrolysis reaction. Yield: 91.8%. Vacuum drying. MS (ASAP) = 738.2.

[0187] The object materials used in this invention are as follows:

[0188] E1 is a green emitting electron, and its synthesis is described in Angew. Chem. Int. Ed. 10.1002 / anie.202007210; E2 is a green emitting electron, and its synthesis is described in Angew. Chem. Int. Ed. 10.1002 / anie.202008264; E3 is a blue emitting electron, and its synthesis is described in US2020395553A1. E4 is a green emitting electron, and E5 and E6 are red emitting electrons. E7 is a blue emitting electron, and its synthesis is described in patent application CN202110370884.X.

[0189] Optical performance testing

[0190] The absorption and emission spectra of compounds 1-16 were measured in toluene solution, and the molar extinction coefficients (ε) were calculated according to the corresponding solubilities. The ε for all compounds 1-16 is ≥ 2. 10 4 Compound 16 has an ε ≥ 6. 10 4 ; ε≥1 for compounds 1-7, 11, 12, 14, 15 10 5 Furthermore, the absorption and emission spectra of E1-E7 were measured in toluene solution. E1-E5 and E7 have relatively narrow emission spectra with an FWHM of less than 40 nm.

[0191] Compositions containing polymers and thin films of organic functional materials are prepared.

[0192] Weigh out 100 mg of polymethyl methacrylate (PMMA), 50 mg of the color conversion material host (compounds 1-16), and 5 mg of the luminescent material, i.e., the color conversion material guest (E1-E7). Dissolve all these substances together in 1 ml of n-butyl acetate to obtain a clear solution, which is the composition or printing ink. Using a KW-4a spin coater, spin-coat the above solution onto a quartz glass surface to form a uniformly thick film, obtaining an organic functional material film, i.e., a color conversion film. The obtained color conversion film, with a thickness less than 4 μm, can achieve an optical density (OD) of [value missing]. 3. In particular, as shown in Table 1, the color conversion layer, with a thickness of less than 3 μm, can achieve an optical density (OD) of [value missing]. 3, and its FWHM 40nm.

[0193] Table 1: Preferred Material Combinations for Color Conversion Layers

[0194] Preparation of compositions containing resin prepolymers and organic functional material films

[0195] The aforementioned color conversion material host and guest materials can also be premixed with a resin prepolymer, such as methyl methacrylate, styrene, or methyl styrene, and then mixed with 1-5 wt% of a photoinitiator, such as TPO (diphenyl(2,4,6-trimethylbenzoyl)phosphine oxide, 97%, CAS: 75980-60-8), to form a film by spin coating or other methods, and then cured by heating and / or under ultraviolet light, such as 365 nm or 390 nm peak ultraviolet LED light, to form a color conversion film.

[0196] The blue color conversion film described above can be placed on a UV or deep blue light self-emissive device, which emits deep blue light with an emission peak between 330-450nm; the deep blue light passes through the blue color converter and emits blue light with an emission peak between 450-500nm.

[0197] The green color conversion film can be placed on a blue self-emissive device that emits blue light with an emission peak between 450-500nm; the blue light passes through the green color converter and emits green or yellow light with an emission peak between 500-580nm.

[0198] The red color conversion film described above can be placed on a blue or green self-emissive device, which emits blue or green light with a emission peak between 450-550nm; the blue or green light passes through the red color converter and emits red light with a emission peak between 580-650nm.

[0199] Fabrication of Top-Emission OLED Light-Emitting Devices

[0200] Preparation of resin-containing color conversion material Ink: Prepolymer preparation: Weigh n-butyl acetate (42wt%), methyl methacrylate (MMA) (50wt%), hydroxypropyl acrylate (HPA) (3wt%), and benzoyl peroxide (BPO) (5wt%), mix and stir at 125℃ for 50 minutes to obtain the prepolymer; The above prepolymer (67wt%) + n-butyl acetate (30wt%) + color conversion host material (compounds 1-16) (2.5wt%) + color conversion guest material (E1-7) (0.5wt%), stir to obtain a clear solution, filter to obtain Ink, and obtain the corresponding Ink1-Ink46 according to the material combination in Table 1.

[0201] Preparation of resin-free color conversion material Ink: The color conversion host material (compounds 1-16) (2.5wt%) + color conversion guest material (E1-7) (0.5wt%) were dissolved in n-butyl acetate, stirred to obtain a clear solution, filtered to obtain Ink, and the corresponding Ink1b-Ink46b were obtained according to the material combinations in Table 1.

[0202] 1. Fabrication of green light-emitting device 1: a. Cleaning of ITO (Indium Tin Oxide) top substrates containing Ag: Use strip solution, pure water, and isopropanol for ultrasonic cleaning in sequence, then dry and perform Ar ozone treatment. b. Vapor deposition: The substrate is transferred into a vacuum vapor deposition apparatus and deposited under high vacuum (1×10⁻⁶). -6 At a temperature of 100 mbar, the ratio of PD to HT-1 was controlled at 3:100 to form a 10 nm hole injection layer (HIL). Subsequently, compound HT-1 was deposited on the hole injection layer to form a 120 nm hole transport layer (HTL). Immediately afterward, compound HT-2 was deposited on the hole transport layer to form a 10 nm hole conditioning layer. As a light-emitting layer, a 25 nm light-emitting layer film was formed with BH:BD at a ratio of 100:3. Next, a 35 nm ET:LiQ (1:1) film was formed as an electron transport layer and placed in different evaporation units for co-deposition at a ratio of 50 wt% to obtain a second electron transport layer. Subsequently, a 1.5 nm Yb layer was deposited as an electron injection layer, and then a 16 nm thick Mg:Ag (1:9) alloy was deposited on the electron injection layer as a cathode. c. On the cathode, Ink (selected from Ink1-Ink28) is printed using a Haisi Electronics IJDAS310 (printer FUJIFILM Dimatix DMC-11610), and then cured under irradiation with a peak 390nm UV LED lamp to obtain a thickness of approximately 3 m's color conversion layer; d. Encapsulation: The device is encapsulated in a nitrogen glove box using UV-cured resin.

[0203] 2. Fabrication of green light-emitting device 1b: Steps a, b, and d are the same as those for the green light-emitting device 1 described above. Step c is as follows: c. On the cathode, use a Hayes Electronics IJDAS310 (printer FUJIFILM Dimatix DMC-11610) to print Ink (selected from Ink1b-Ink28b) to obtain a thickness of 1-2 mm. m's color conversion layer; 3. Fabrication of blue light-emitting device 1: Steps a and d are the same as those for the green light-emitting device 1 described above; steps b and c are as follows: b. Vapor deposition: The substrate is transferred into a vacuum vapor deposition apparatus and deposited under high vacuum (1×10⁻⁶). -6 At a concentration of 10 nm, the ratio of PD to HT-1 was controlled at 3:100 to form a 10 nm hole injection layer (HIL). Subsequently, compound HT-1 was deposited on the hole injection layer to form a 120 nm hole transport layer (HTL). Then, compound HT-2 was deposited on the hole transport layer to form a 10 nm hole conditioning layer. As a light-emitting layer, a 25 nm light-emitting layer film was formed using BH (100%). Next, a 35 nm ET:LiQ (1:1) film was formed as an electron transport layer. The films were placed in different evaporation units and co-deposited at a ratio of 50 wt% to obtain a second electron transport layer. Subsequently, a 1.5 nm Yb layer was deposited as an electron injection layer, and a 16 nm thick Mg:Ag (1:9) alloy was deposited on the electron injection layer as a cathode. c. On the cathode, use a Haisi Electronics IJDAS310 (printer FUJIFILM Dimatix DMC-11610) to print Ink (Ink29-Ink36) to obtain a thickness of approximately 3. m's color conversion layer; 4. Fabrication of blue light-emitting device 1b: Steps a, b, and d are the same as those for blue light-emitting device 1 described above. Step c is as follows: c. On the cathode, use a Hayes Electronics IJDAS310 (printer FUJIFILM Dimatix DMC-11610) to print Ink (selected from Ink29b-Ink36b) to obtain a thickness of 1-2 mm. m's color conversion layer; 5. Fabrication of green light-emitting device 2: Steps a, b, and c are the same as those for the green light-emitting device 1 described above; steps d and e are as follows: d. A 70nm thick CPL is deposited on the color conversion layer as an optical cover layer.

[0204] e. Packaging: The device is encapsulated in a nitrogen glove box using UV-cured resin.

[0205] 6. Fabrication of red light-emitting device 1: Steps a, b, and d are the same as those for the green light-emitting device 1 described above, while step c is as follows: c. On the cathode, ink (selected from Ink37-Ink46) is printed using a Haisi Electronics IJDAS310 (printer FUJIFILM Dimatix DMC-11610), and then cured under irradiation with a peak 390nm UV LED lamp to obtain a thickness of 2-3 mm. m's color conversion layer; 7. Fabrication of red light-emitting device 1b: Steps a, b, and d are the same as those for the green light-emitting device 1 described above, while step c is as follows: c. On the cathode, use a Hayes Electronics IJDAS310 (printer FUJIFILM Dimatix DMC-11610) to print Ink (selected from Ink37b-Ink46b) to obtain a thickness of 1-2 mm. m's color conversion layer; All of the above light-emitting devices have high color purity, and their emission spectrum lines have an FWHM of less than 40 nm.

[0206] The technical features of the above embodiments can be combined in any way. For the sake of brevity, not all possible combinations of the technical features in the above 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.

[0207] The embodiments described above are merely illustrative of several implementations of the present invention, and while the descriptions are relatively specific and detailed, they should not be construed as limiting the scope of the invention patent. It should be noted that those skilled in the art can make various modifications and improvements without departing from the concept of the present invention, and these all fall within the protection scope of the present invention. Therefore, the protection scope of this invention patent should be determined by the appended claims.

Claims

1. A compound comprising structural units shown in the following chemical formula, The symbols and markings used have the following meanings: R2 is a substituent, which may be the same as or different from a straight-chain alkyl, haloalkyl, alkoxy, or thioalkoxy group having 1 to 20 carbon atoms; or a branched or cyclic alkyl, haloalkyl, alkoxy, or thioalkoxy group having 3 to 20 carbon atoms; or a silyl group; or a substituted ketone group having 1 to 20 carbon atoms; or an alkoxycarbonyl group having 2 to 20 carbon atoms; or an aryloxycarbonyl group having 7 to 20 carbon atoms; a cyano group; a carbamoyl group; or a haloformyl group. Group, formyl group (-C(=O)-H), isocyanate group, isocyanate group, thiocyanate group or isothiocyanate group, hydroxy group, NO2, CF3, Cl, Br, F, I, crosslinkable group, or substituted or unsubstituted aromatic or heteroaromatic ring system having 5 to 40 ring atoms, or aryloxy or heteroaryloxy group having 5 to 40 ring atoms, or arylamine or heteroarylamine group having 5 to 40 ring atoms, disubstituted unit at any position of the above substituents or combination of these substituents; m is selected from natural numbers from 1 to 12. Its features are, The compound contains at least one alcohol-soluble or water-soluble group.

2. The compound according to claim 1, characterized in that, The compound contains structural units represented by the following chemical formulas: in: m1 is selected from natural numbers from 1 to 10, and r is 0 or 1; R2 is defined as in claim 1; Ar1-Ar4, each time appearing, are independently selected from substituted or unsubstituted aromatic or heteroaromatic ring systems having 5 to 40 ring atoms, or aryloxy or heteroaryloxy groups having 5 to 40 ring atoms, or combinations of these systems. Each time L1 and L2 appear, they are independently selected from single bonds, substituted or unsubstituted aromatic groups or heteroaromatic groups with 6 to 30 ring atoms.

3. The compound according to claim 1 or 2, characterized in that, The alcohol-soluble or water-soluble group is selected from: alcohols, aldehydes, acids, crown ethers, polyethers, and primary amines.

4. The compound according to any one of claims 1-3, characterized in that, The alcohol-soluble or water-soluble group is selected from: in: R 31 -R 37 It may be a straight-chain alkyl, alkoxy, or thioalkoxy group having 1 to 20 carbon atoms, or a branched or cyclic alkyl, alkoxy, thioalkoxy, or silyl group having 3 to 20 carbon atoms, or a substituted ketone group having 1 to 20 carbon atoms, or an alkoxycarbonyl group having 2 to 20 carbon atoms, or an aryloxycarbonyl group having 7 to 20 carbon atoms, a cyano group, a carbamoyl group, a haloformyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group or an isothiocyanate group, a hydroxy group, a nitro group, CF3, Cl, Br, F, a crosslinkable group, or a substituted or unsubstituted aromatic or heteroaromatic ring system having 5 to 40 ring atoms, or an aryloxy or heteroaromatic group having 5 to 40 ring atoms, or a combination of these groups, wherein one or more of the groups may form a monocyclic or polycyclic aliphatic or aromatic ring system with each other and / or with the rings bonded to the groups; The dashed line represents a bonded bond; t is an integer greater than 0.

5. A mixture comprising at least one compound as described in any one of claims 1-4 and another functional material, wherein the other functional material is selected from organic functional materials, and may be selected from hole injection or transport materials (HIM / HTM), hole blocking materials (HBM), electron injection or transport materials (EIM / ETM), electron blocking materials (EBM), organic matrix materials (Host), singlet luminescent materials (fluorescent materials), triplet luminescent materials (phosphorescent materials), thermally excited delayed fluorescence materials (TADF materials), and organic dyes.

6. A composition comprising at least one compound as described in any one of claims 1-4, at least one organic solvent, and / or an organic resin.

7. The composition according to claim 6, characterized in that, The organic solvent is selected from alcohols, esters, aromatic ketones or aromatic ethers, aliphatic ketones or aliphatic ethers, borate esters or phosphate esters, or mixtures of two or more solvents.

8. The composition according to claim 6, characterized in that, The organic resin is selected from thermosetting resins or UV-curable resins.

9. The composition according to any one of claims 6-8, characterized in that, The composition further comprises a light emitter E, 1) the emission spectrum of the compound is on the shorter wavelength side of the absorption spectrum of the light emitter E and at least partially overlaps with it; 2) the half-width at half maximum (FWHM) of the emission spectrum of the light emitter E is less than or equal to 55 nm.

10. An organic functional material film comprising a compound as described in any one of claims 1-4, or prepared using a composition according to any one of claims 6-9.

11. An optoelectronic device comprising a compound as described in any one of claims 1-4 or an organic functional material thin film as described in claim 10.

12. 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 as described in any one of claims 1-4 and a light emitter E; (2) The color conversion layer is capable of at least partially absorbing the light emitted by the organic light-emitting layer that is transmitted through the second electrode; (3) The emission spectrum of the compound is on the short wavelength side of the absorption spectrum of the light emitter E and at least partially overlaps with it; (4) The half-width at half maximum (FWHM) of the emission spectrum of the light emitter E is less than or equal to 55 nm.

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