Dianthryl fluorene compound and organic electroluminescent device thereof

Abstract

The invention relates to a dianthryl fluorene compound and a luminescent device thereof. The compound has a structure as shown in a formula (I). The compound has large steric hindrance, the specific molecular structure enables the compound to have increased film mobility, the luminous efficiency of a luminescent device can be improved, the voltage of the device can be reduced, and the service life of the device can be prolonged.

Description

Technical Field

[0001] The present invention relates to the field of organic electroluminescent materials, and in particular to a dianthrylfluorene compound. Background Art

[0002] Organic electroluminescent devices (OLEDs) offer a range of advantages, including autonomous illumination, low-voltage drive, full curing, wide viewing angles, and simpler components and processes. Compared to liquid crystal displays (LCDs), OLEDs do not require a backlight. Therefore, OLEDs have broad application prospects.

[0003] Organic electroluminescent devices generally include an anode, a metal cathode, and an organic layer sandwiched between them. The organic layer mainly includes a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer. In addition, the light-emitting layer mostly adopts a host-guest structure. That is, the light-emitting material is doped into the host material at a certain concentration to avoid concentration quenching and triplet-triplet annihilation, thereby improving the luminous efficiency. With the significant progress of OLED devices, the performance requirements for the host material are also increasing. Therefore, the host material is generally required to have a higher triplet energy level and higher stability at the same time. Existing blue light host materials mainly use monoanthracene or dianthracene as the skeleton. By modifying the side chains connected to it, its material properties are changed, thereby changing its device performance.

[0004] Published patent document CN119080750A discloses a luminescent material based on a spirocyclic bicanthracenes structure; patent document CN116751177A discloses a blue-light-emitting host material based on a dimethylfluorene structure, but the device performance of the dimethylfluorene-based blue-light-emitting host material in this device is far inferior to that of the furan-based host material. Patent document CN112094170A discloses fluorene compounds and light-emitting devices thereof that incorporate organic compounds through unique, highly sterically hindered connection sites, improving device efficiency and lifespan.

[0005] While a large number of high-performance multi-resonance thermally activated delayed fluorescence (MR-TADF) materials have been developed, blue-light-emitting host materials are unable to meet the rapidly growing demand of the entire industry. Therefore, it is necessary to develop and design blue-light-emitting host materials with excellent thermal stability and high performance to produce blue and deep-blue organic electroluminescent devices with high luminescence efficiency, low driving voltage, and long life. Summary of the Invention

[0006] In view of the problems existing in the prior art, the present invention provides a dianthrylfluorene compound, which can improve the driving voltage, luminous efficiency and short life of organic electroluminescent devices.

[0007] The present invention provides a dianthrylfluorene compound having a structure shown in formula (I):

[0008]

[0009] in,

[0010] Ar1 and Ar2 are the same or different and are independently selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl;

[0011] Ar3 and Ar4 are the same or different and are independently selected from substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C2-C30 heteroaryl;

[0012] R1-R4 are the same or different and are independently selected from hydrogen, deuterium, tritium, halogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; or two adjacent R1s are linked together to form a substituted or unsubstituted ring, or two adjacent R2s are linked together to form a substituted or unsubstituted ring;

[0013] L1-L4 are the same or different and are independently selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, or a substituted or unsubstituted C2-C30 heteroarylene group;

[0014] n is the same or different and is independently selected from 0, 1, 2 or 3;

[0015] m is the same or different and is independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8.

[0016] The present invention also provides an organic electroluminescent device comprising a first electrode, a second electrode opposite to the first electrode, and at least one organic layer sandwiched between the first electrode and the second electrode, wherein the at least one organic layer comprises the dianthrylfluorene compound of the present invention.

[0017] The present invention provides a series of novel dianthrylfluorene compounds and light-emitting devices thereof. The compounds of the present invention exhibit significant steric hindrance, particularly the introduction of highly rigid planar anthracene groups and their derivatives at the 1 and 8 positions, which restrict free rotation and completely lock the molecular conformation into a specific structure. This is extremely important for the arrangement of molecules and can induce the molecules of the present invention to form a regular, face-to-face, side-by-side structure parallel to the substrate, thereby increasing the mobility of the film, increasing luminescence perpendicular to the film direction, improving luminescence efficiency, and reducing device voltage. Furthermore, the locked conformation reduces intramolecular vibrational relaxation, which is a non-radiative process in which energy is directly converted into heat. Therefore, intramolecular vibrational relaxation is reduced, and more energy is used for luminescence, ultimately resulting in improved luminescence efficiency and reduced device voltage. Furthermore, the locked conformational molecular design and the introduction of deuterated atoms improve device life. BRIEF DESCRIPTION OF THE DRAWINGS

[0018] Figure 1 Schematic diagram of the structure of an organic electroluminescent device.

[0019] Explanation of the reference numerals: 1 substrate; 2 anode; 3 hole injection layer; 4 hole transport layer; 5 electron blocking layer; 6 light-emitting layer; 7 hole blocking layer; 8 electron transport layer; 9 electron injection layer; 10 cathode.

[0020] Figure 2 Electroluminescence spectrum of Example device 10. DETAILED DESCRIPTION

[0021] The following will be a clear and complete description of the technical solutions of the specific embodiments of the present invention. Obviously, the embodiments described are only part of the embodiments of the present invention, not all of them. Based on the embodiments of the present invention, all other embodiments obtained by those skilled in the art without making any creative efforts shall fall within the scope of protection of the present invention.

[0022] In the compounds of the present invention, any atom not designated as a specific isotope is included as any stable isotope of that atom, and includes the atom at both its natural isotopic abundance and unnatural abundance.

[0023] Unless otherwise specified, the term "alkyl" refers to a monovalent saturated aliphatic hydrocarbon group, a straight or branched chain group containing 1 to 30 carbon atoms, preferably containing 1 to 15 carbon atoms, 1 to 10 carbon atoms, or 1 to 6 carbon atoms. Examples include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, and the like.

[0024] Unless otherwise specified, the term "cycloalkyl" refers to a monocyclic saturated aliphatic hydrocarbon group having a specific number of carbon atoms, preferably containing 3-30 carbon atoms, preferably containing 3-15 carbon atoms or 3-10 carbon atoms or 3-8 carbon atoms, examples of which include but are not limited to cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, etc.

[0025] Unless otherwise specified, the term "aryl" or "aromatic ring group" refers to a monocyclic, polycyclic, or fused aromatic carbocyclic ring system containing 6 to 30 carbon atoms, or 6 to 25 carbon atoms, or 6 to 14 carbon atoms, or 6 to 10 carbon atoms. The term "aryl" can be used interchangeably with the term "aromatic ring." Examples of aryl groups include, but are not limited to, phenyl, biphenyl, terphenyl, quaterphenyl, 1-phenylnaphthyl, 2-phenylnaphthyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyrenyl, perylenyl, fluoranthenyl, fluorenyl, benzofluorenyl, spirofluorenyl, spirobifluorenyl, and the like.

[0026] Unless otherwise specified, the term "arylene" refers to a radical derived from an aryl radical by removing a hydrogen atom. The arylene radical contains 6 to 30 carbon atoms, or 6 to 25 carbon atoms, or 6 to 14 carbon atoms, or 6 to 10 carbon atoms; examples of arylene radicals include, but are not limited to, phenylene, biphenylene, terphenylene, quaterphenylene, phenylnaphthylene, naphthylene, anthrylene, phenanthrenylene, triphenylene, pyrenylene, perylene, fluoranthenylene, fluorenylene, benzofluorenylene, spirofluorenylene, spirobifluorenylene, and the like.

[0027] Unless otherwise specified, the term "heteroaryl" or "heteroaryl ring group" means a monocyclic, polycyclic or fused ring system containing 2-30 carbon atoms, 2-25 carbon atoms, or 2-14 carbon atoms, or 3-10 carbon atoms, in which 1, 2, 3 or more of the ring atoms are heteroatoms independently selected from oxygen, sulfur, nitrogen, silicon, selenium or phosphorus atoms and the remaining atoms are carbon. Examples of heteroaryl groups include, but are not limited to, pyrrolyl, furanyl, thienyl, oxazolyl, thiazolyl, imidazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, bipyridyl, bipyrimidinyl, phenylpyridyl, phenylpyrimidinyl, spiroxanthenyl, spiroxanthenyl, acridinyl, 9,10-dihydroacridinyl, naphthyridinyl, indolyl, phenoxazinyl, phenothiazinyl, phenoxathiyl, quinolinyl, isoquinolinyl, , benzoquinolinyl, benzoisoquinolinyl, quinazoline, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, o-phenanthroline, benzofuranyl, dibenzofuranyl, naphthiobenzofuranyl, benzothienyl, benzothiazolyl, dibenzothienyl, naphthiobenzothienyl, benzoxazolyl, naphthioxazolyl, benzimidazolyl, naphthiazolyl, benzothiazolyl, naphthiozolyl, carbazolyl, benzocarbazolyl, and the like.

[0028] Unless otherwise specified, the term "heteroarylene" refers to a radical derived from a heteroaryl radical by removing a hydrogen atom. A heteroarylene radical contains 2-30 carbon atoms, 2-25 carbon atoms, or 2-14 carbon atoms, or 3-10 carbon atoms, wherein one, two, three or more ring atoms are heteroatoms and the remaining atoms are carbon, the heteroatoms being independently selected from oxygen, sulfur, nitrogen, silicon, selenium, or phosphorus atoms. Examples of heteroarylene radicals include, but are not limited to, pyridylene, pyrimidylene, triazinylene, dibenzofuranylene, dibenzothiophenylene, carbazolylene, and the like.

[0029] Unless otherwise specified, the term "halogen" or "halo" refers to F, Cl, Br, and I.

[0030] Unless otherwise indicated, the structural formulas described herein include all isomeric forms (e.g., enantiomers, diastereomers, and geometric isomers (or conformers)): for example, R and S configurations containing asymmetric centers, (Z) and (E) isomers of double bonds, and (Z) and (E) conformers. Therefore, single stereochemical isomers of the compounds of the present invention or mixtures of their enantiomers, diastereomers, or geometric isomers (or conformers) are within the scope of the present invention.

[0031] Unless otherwise specified, the term "substituted" means that a hydrogen atom in certain functional groups is replaced by another atom or functional group (i.e., a substituent), and the position of the substitution is not limited as long as the position is the position where the hydrogen atom is replaced, and when two or more substituents are substituted, the two or more substituents may be the same as or different from each other.

[0032] Unless otherwise specified, the term "substituted or unsubstituted" means not substituted or substituted with one or more substituents selected from the group consisting of deuterium, tritium, halogen, cyano, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C25 heteroaryl, amino substituted with substituted or unsubstituted C6-C25 aryl and / or substituted or unsubstituted C2-C25 heteroaryl, and substituted or unsubstituted silyl. Preferably, the "substituted or unsubstituted" means not substituted or substituted by one or more substituents selected from the group consisting of: deuterium, tritium, halogen, cyano, C1-C10 alkyl, halogen-substituted alkyl, C3-C10 cycloalkyl, C6-C14 aryl, C2-C14 heteroaryl, substituted or unsubstituted C6-C14 aryl and / or substituted or unsubstituted C2-C14 heteroaryl substituted amino, substituted or unsubstituted silyl. In the case of being substituted by multiple substituents, the multiple substituents are the same or different from each other. Most preferably, the term "substituted or unsubstituted" means not substituted or substituted with one or more substituents selected from the group consisting of deuterium, tritium, fluorine, chlorine, bromine, iodine, cyano, methyl, trifluoromethyl, deuterated methyl, ethyl, deuterated ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, Anthracenyl, deuterated anthracenyl, phenanthryl, deuterated phenanthryl, triphenylene, pyrenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirobifluorenyl, pyridyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, N-phenylcarbazolyl, N-biphenylcarbazolyl, dibenzofuranyl, dibenzothiophenyl, trimethylsilyl, triphenylsilyl; when substituted with multiple substituents, the multiple substituents may be the same or different.

[0033] Unless otherwise specified, when a substituent on a ring is not indicated as fixed, it represents that the substituent is attached to any of the corresponding optional positions of the ring.

[0034] Unless otherwise specified, when a substituent or a bond at a site of attachment runs through two or more rings, it indicates that it can be attached to any of the two or more rings, specifically any of the corresponding optional sites of the rings.

[0035] Unless otherwise specified, "adjacent groups connected to form a substituted or unsubstituted ring" means that adjacent groups are bonded and optionally aromatized to form a substituted or unsubstituted aromatic ring, heteroaromatic ring, aliphatic ring, or aliphatic heterocycle. Furthermore, the ring formed by the connection includes, but is not limited to, benzene, naphthalene, indene, cyclopentane, cyclohexane, pyridine, and pyrimidine. The term "adjacent groups" includes groups substituted on the same atom, groups substituted on adjacent atoms, and groups adjacent in space.

[0036] It should be understood that within the scope of the present invention, the above-mentioned technical features of the present invention and the technical features described in detail below (such as in the embodiments) can be combined with each other to form new or preferred technical solutions. Due to space limitations, they are not listed here one by one.

[0037] In a first aspect, the present invention provides a dianthrylfluorene compound having a structure shown in formula (I):

[0038]

[0039] in,

[0040] Ar1 and Ar2 are the same or different and are independently selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl;

[0041] Ar3 and Ar4 are the same or different and are independently selected from substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C2-C30 heteroaryl;

[0042] R1-R4 are the same or different and are independently selected from hydrogen, deuterium, tritium, halogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; or two adjacent R1s are linked together to form a substituted or unsubstituted ring, or two adjacent R2s are linked together to form a substituted or unsubstituted ring;

[0043] L1-L4 are the same or different and are independently selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, or a substituted or unsubstituted C2-C30 heteroarylene group;

[0044] n is the same or different and is independently selected from 0, 1, 2 or 3;

[0045] m is the same or different and is independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8.

[0046] Preferably, Ar1 and Ar2 are the same or different and are independently selected from one of the following structures:

[0047]

[0048] Among them, R 11 、R 12 are the same or different and are independently selected from hydrogen, deuterium, tritium, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C2-C18 heteroaryl; or two adjacent R 11 linked together to form substituted or unsubstituted rings;

[0049] M is selected from O, S, CR 13 R 14 or NR 15 , the R 13 、R 14 、R 15 the same or different, independently selected from substituted or unsubstituted C-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C2-C18 heteroaryl;

[0050] a1 is the same or different and is independently selected from 0, 1, 2, 3, 4 or 5; a2 is the same or different and is independently selected from 0, 1, 2, 3 or 4; a3 is the same or different and is independently selected from 0, 1, 2, 3, 4, 5, 6 or 7; a4 is the same or different and is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; a0 is the same or different and is independently selected from 0, 1 or 2.

[0051] Preferably, Ar1 and Ar2 are the same or different and are independently selected from one of the following structures:

[0052]

[0053] Among them, R 11 、R 12 the same or different, independently selected from hydrogen, deuterium, tritium, fluorine, chlorine, bromine, iodine, substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyrenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, dibenzofuranyl, dibenzothiophenyl, 9-phenylcarbazolyl, 9-biphenylcarbazolyl, 9-naphthylcarbazolyl;

[0054] R 21the same or different, independently selected from hydrogen, deuterium, tritium, fluorine, chlorine, bromine, iodine, substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl;

[0055] M is selected from O, S, CR 13 R 14 or NR 15 , the R 13 、R 14 The same or different, independently selected from substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, phenyl, biphenyl, naphthyl, dibenzofuranyl, dibenzothiophenyl; the R 15 Selected from substituted or unsubstituted: phenyl, biphenyl, naphthyl;

[0056] Ar a 、Ar b the same or different, independently selected from substituted or unsubstituted: phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyrenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, dibenzofuranyl, dibenzothiophenyl, 9-phenylcarbazolyl, 9-biphenylcarbazolyl, 9-naphthylcarbazolyl;

[0057] a1 is the same or different and is independently selected from 0, 1, 2, 3, 4 or 5; a2 is the same or different and is independently selected from 0, 1, 2, 3 or 4; a3 is the same or different and is independently selected from 0, 1, 2, 3, 4, 5, 6 or 7; a4 is the same or different and is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; a5 is the same or different and is independently selected from 0, 1, 2, 3, 4, 5 or 6; a6 is the same or different and is independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; a0 is the same or different and is independently selected from 0, 1 or 2.

[0058] Preferably, the Ar a 、Ar b The same or different, independently selected from one of the following structures:

[0059]

[0060] Preferably, R 11 -R 15 、R 21 、Ar a 、Ar b The substituents in the "substituted or unsubstituted" are selected from the group consisting of deuterium, tritium, halogen, cyano, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted phenyl, and substituted or unsubstituted pyridyl.

[0061] Preferably, Ar1 and Ar2 are the same or different and are independently selected from one of the following structures:

[0062]

[0063] Preferably, Ar3 and Ar4 are the same or different and are independently selected from substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, phenyl, biphenyl, naphthyl, dibenzofuranyl, dibenzothiophenyl.

[0064] Preferably, the substituent in "substituted or unsubstituted" in Ar3 and Ar4 is selected from: deuterium, tritium, halogen, cyano, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted phenyl, substituted or unsubstituted pyridyl.

[0065] More preferably, Ar3 and Ar4 are the same or different and are independently selected from methyl, deuterated methyl, phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, naphthyl, and deuterated naphthyl.

[0066] Preferably, L1-L4 are the same or different, and are independently selected from a single bond, or substituted or unsubstituted: phenylene, biphenylene, naphthylene, anthracene, pyridylene, pyrimidylene.

[0067] Preferably, L1-L4 are the same or different and are independently selected from a single bond, or one of the following groups:

[0068]

[0069] Among them, R a is selected from hydrogen, deuterium, tritium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C14 aryl, substituted or unsubstituted C2-C12 heteroaryl; or two adjacent R a linked together to form a substituted or unsubstituted C6-C10 aromatic ring;

[0070] b1 is the same or different and is independently selected from 0, 1, 2, 3 or 4; b2 is the same or different and is independently selected from 0, 1, 2 or 3; b3 is the same or different and is independently selected from 0, 1 or 2; b4 is the same or different and is independently selected from 0, 1, 2, 3, 4, 5 or 6; b5 is the same or different and is independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8.

[0071] Preferably, R aSelected from hydrogen, deuterium, tritium, fluorine, chlorine, bromine, iodine, cyano, trifluoromethyl, substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl.

[0072] Preferably, R a The substituents in the "substituted or unsubstituted" are selected from the group consisting of deuterium, tritium, halogen, cyano, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted phenyl, and substituted or unsubstituted pyridyl.

[0073] Preferably, the R1-R4 are the same or different and are independently selected from hydrogen, deuterium, tritium, halogen, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C14 aryl, substituted or unsubstituted C2-C12 heteroaryl; or two adjacent R1s are connected together to form a substituted or unsubstituted C6-C10 aromatic ring, or two adjacent R2s are connected together to form a substituted or unsubstituted C6-C10 aromatic ring.

[0074] Preferably, R1-R4 are the same or different and are independently selected from hydrogen, deuterium, tritium, fluorine, chlorine, bromine, iodine, substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyrenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, dibenzofuranyl, dibenzothiophenyl, 9-phenylcarbazolyl, 9-biphenylcarbazolyl, 9-naphthylcarbazolyl.

[0075] Preferably, the substituents in "substituted or unsubstituted" in R1-R4 are selected from: deuterium, tritium, halogen, cyano, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted phenyl, substituted or unsubstituted pyridyl.

[0076] In one embodiment, the dianthrylfluorene compound has a structure shown in formula (I-1):

[0077]

[0078] wherein Ar5 is selected from substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl;

[0079] n1 is selected from 0, 1 or 2;

[0080] Ar1-Ar4, R1-R4, L1-L4, n, and m are as defined herein.

[0081] Preferably, Ar5 is selected from substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C14 aryl, and substituted or unsubstituted C2-C14 heteroaryl.

[0082] More preferably, Ar5 is selected from the group consisting of substituted or unsubstituted methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, phenyl, biphenyl, naphthyl, dibenzofuranyl, and dibenzothiophenyl.

[0083] Preferably, the substituent in "substituted or unsubstituted" in Ar5 is selected from the group consisting of: deuterium, tritium, halogen, cyano, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted phenyl, substituted or unsubstituted pyridyl.

[0084] Preferably, Ar5 is selected from methyl, deuterated methyl, ethyl, deuterated ethyl, n-propyl, deuterated n-propyl, isopropyl, deuterated isopropyl, n-butyl, deuterated n-butyl, isobutyl, deuterated isobutyl, sec-butyl, deuterated sec-butyl, tert-butyl, deuterated tert-butyl, pentyl, deuterated pentyl, hexyl, deuterated hexyl, cyclopropyl, deuterated cyclopropyl, cyclobutyl, deuterated cyclobutyl, cyclopentyl, deuterated cyclopentyl, cyclohexyl, deuterated cyclohexyl, adamantyl, deuterated adamantyl, and one of the following structures:

[0085]

[0086] In one embodiment, the dianthrylfluorene compound has a structure shown in formula (I-2):

[0087]

[0088] In one embodiment, the deuteration rate of the dianthrylfluorene compound is 1-99%, preferably, the deuteration rate is 10-90%, and more preferably, the deuteration rate of the dianthrylfluorene compound is 60-90%.

[0089] In one embodiment, the dianthrylfluorene compound is selected from:

[0090]

[0091]

[0092]

[0093]

[0094] The above lists only some specific structural forms of the dianthrylfluorene compounds represented by formula (I), but the present invention is not limited to these listed chemical structures. All chemical structures based on formula (I) and with substituents as defined in the present invention are included.

[0095] The dianthrylfluorene compound represented by formula (I) of the present invention can be prepared by one of the following synthetic routes:

[0096]

[0097] Wherein, X1 and X2 are the same or different and are independently selected from chlorine, bromine or iodine;

[0098] M1, M2 are the same or different, and are independently selected from -B(OH)2 or

[0099] In a second aspect, the present invention further provides a light-emitting device comprising a first electrode, a second electrode opposite to the first electrode, and at least one organic layer sandwiched between the first electrode and the second electrode, wherein the at least one organic layer comprises the dianthrylfluorene compound of the present invention.

[0100] In one embodiment, the light-emitting device is an organic electroluminescent device; preferably, the light-emitting device is a blue organic electroluminescent device.

[0101] In one embodiment, the organic layer includes a light-emitting layer, and the light-emitting layer includes the dianthrylfluorene compound of the present invention.

[0102] In one embodiment, the organic layer includes a light-emitting layer, the light-emitting layer includes a host material, and the host material includes the dianthrylfluorene compound of the present invention.

[0103] In one embodiment, Figure 1 As shown, the organic electroluminescent device of the present invention is obtained by sequentially arranging various layers (for example, an anode 2, a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light-emitting layer 6, a hole blocking layer 7, an electron transport layer 8, an electron injection layer 9 and a cathode 10) on a substrate 1.

[0104] The organic electroluminescent device of the present invention is not limited to such a structure. For example, in the multilayer structure, one or some of the organic layers can be omitted. For example, the hole blocking layer 7 between the light-emitting layer 6 and the electron transport layer 8 can be omitted, and the anode 2, the hole injection layer 3, the hole transport layer 4, the electron blocking layer 5, the light-emitting layer 6, the electron transport layer 8, the electron injection layer 9 and the cathode 10 are sequentially arranged on the substrate 1. Alternatively, the hole injection layer 3 between the anode 2 and the hole transport layer 4, the hole blocking layer 7 between the light-emitting layer 6 and the electron transport layer 8, and the electron injection layer 9 between the electron transport layer 8 and the cathode 10 can be omitted at the same time, and the anode 2, the hole transport layer 4, the electron blocking layer 5, the light-emitting layer 6, the electron transport layer 8 and the cathode 10 are sequentially arranged on the substrate 1 to finally obtain the corresponding organic electroluminescent device.

[0105] The organic electroluminescent device of the present invention is not limited to such a structure. For example, in the multilayer structure, one or some of the organic layers can be omitted. For example, the hole blocking layer 7 between the light-emitting layer 6 and the electron transport layer 8 can be omitted, and the anode 2, the hole injection layer 3, the hole transport layer 4, the electron blocking layer 5, the light-emitting layer 6, the electron transport layer 8, the electron injection layer 9 and the cathode 10 are sequentially arranged on the substrate 1. Alternatively, the hole injection layer 3 between the anode 2 and the hole transport layer 4, the hole blocking layer 7 between the light-emitting layer 6 and the electron transport layer 8, and the electron injection layer 9 between the electron transport layer 8 and the cathode 10 can be omitted at the same time, and the anode 2, the hole transport layer 4, the electron blocking layer 5, the light-emitting layer 6, the electron transport layer 8 and the cathode 10 are sequentially arranged on the substrate 1 to finally obtain the corresponding organic electroluminescent device.

[0106] The anode of the organic electroluminescent device of the present invention can be composed of known electrode materials. For example, electrode materials with a large work function can be used, such as metals such as vanadium, chromium, copper, zinc, and gold, or their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline. Among these, ITO is preferred.

[0107] As the hole injection layer of the organic electroluminescent device of the present invention, known materials with hole injection properties can be used. For example, porphyrin compounds represented by copper phthalocyanine, naphthalenediamine compounds, star-shaped triphenylamine compounds, aromatic amine compounds having a structure in which three or more triphenylamine structures are connected by a single bond or a divalent group containing no heteroatoms, triphenylamine trimers and tetramers, acceptor-type dibenzofuran compounds such as hexacyanoazatriphenylene, and coating-type polymer materials. These materials can be formed into thin films by known methods such as vapor deposition, spin coating, and inkjet methods.

[0108] As the hole transport layer of the organic electroluminescent device of the present invention, a well-known material with hole transport properties can be used. In addition, other well-known materials with hole transport properties can also be used. For example, compounds containing m-carbazolylphenyl; such as N,N'-diphenyl-N,N'-di(m-tolyl)benzidine (TPD), N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (NPB), N,N,N',N'-tetraphenylbenzidine and other benzidine derivatives; 1,1-bis[(di-4-tolylamino)phenyl]cyclohexane (TAPC); various triphenylamine trimers and tetramers; 9,9',9"-triphenyl -9H,9'H,9"H-3,3':6',3"-tricarbazole (Tris-PCz), etc. These can be formed into films alone or as a single layer formed by mixing with other materials. They can also be formed into a stacked structure of layers formed from individual films, a stacked structure of layers formed from mixed films, or a stacked structure of layers formed from individual films and layers formed from mixed films. These materials can be formed into thin films by known methods such as vapor deposition, spin coating, and inkjet methods.

[0109] In addition, materials commonly used in the hole injection layer or hole transport layer may be further P-doped with tribromoaniline antimony hexachloride, a radialene derivative, or a polymer compound partially having a structure of a benzidine derivative such as TPD.

[0110] As the electron blocking layer of the organic electroluminescent device of the present invention, a well-known material with electron blocking properties can be used. In addition, other well-known compounds with electron blocking effects can also be used to form it. For example, carbazole derivatives such as 4,4',4"-tris(N-carbazolyl)triphenylamine (TCTA), 9,9-bis[4-(carbazol-9-yl)phenyl]fluorene, 1,3-bis(carbazol-9-yl)benzene (mCP), 2,2-bis(4-carbazol-9-ylphenyl)adamantane (Ad-Cz); compounds with triphenylsilyl and triarylamine structures represented by 9-[4-(carbazol-9-yl)phenyl]-9-[4-(triphenylsilyl)phenyl]-9H-fluorene Compounds with electron-blocking properties, such as monoamine compounds with high electron-blocking properties and various triphenylamine dimers, can be used alone or in a single layer by mixing with other materials. They can also be used in a laminated structure of layers formed from individual films, a laminated structure of layers formed from mixed films, or a laminated structure of layers formed from individual films and mixed films. These materials can be formed into thin films using known methods such as vapor deposition, spin coating, and inkjet methods.

[0111] The light-emitting layer of the organic electroluminescent device of the present invention preferably comprises a fluorene dibenzofuran compound represented by formula (I) of the present invention. In addition, various metal complexes such as metal complexes of hydroxyquinoline derivatives headed by Alq3, compounds having a pyrimidine ring structure, anthracene derivatives, bis(vinylbenzene) derivatives, pyrene derivatives, oxazole derivatives, and poly(p-phenylene vinylene) derivatives can also be used.

[0112] The light-emitting layer can be composed of a host material and a dopant material. As the host material, it is preferred to include a fluorene dibenzofuran compound represented by formula (I) of the present invention. In addition, mCBP, mCP, thiazole derivatives, benzimidazole derivatives, polydialkylfluorene derivatives, dibenzofuran compounds having an indole ring as a partial structure of the fused ring, etc. can also be used. As the dopant material, it is preferred to include a dibenzofuran derivative of the present invention. In addition, aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, etc. can also be used. For example, pyrene derivatives, anthracene derivatives, quinacridone, coumarin, rubrene, perylene and their derivatives, benzopyran derivatives, rhodamine derivatives, aminostyryl derivatives, spirocyclic bisfluorene derivatives, etc. can be listed. These materials can be formed into films alone or mixed with other materials to form a single layer. They can also be used in the form of a laminated structure of layers formed alone, a laminated structure of layers formed as a mixture, or a laminated structure of layers formed alone and layers formed as a mixture. These materials can be formed into thin films by known methods such as vapor deposition, spin coating, and inkjet.

[0113] Preferably, the mass ratio of the host material to the doping material in the light-emitting layer may be 50-99:1-50, and preferably, the mass ratio may be 80-99:1-20.

[0114] As the hole blocking layer of the organic electroluminescent device of the present application, a material known to have a hole blocking property can be used. In addition to this, other compounds having a hole blocking property can be used to form. For example, 2,4,6-tris(3-phenyl)-1,3,5-triazine (T2T), 1,3,5-tris(1-phenyl-1H-benzimidazol-2-yl)benzene (TPBi), phenanthroline derivatives such as bathocuproin (BCP), metal complexes of quinolinol derivatives such as aluminum (III) bis(2-methyl-8-quinolinolato)-4-phenylphenolate (BAlq), and various rare earth complexes, oxazole derivatives, triazole derivatives, triazine derivatives, and the like. They can be formed into a film alone, or can be used in the form of a single layer formed by mixing with other materials, or can be formed into a stacked structure of layers formed by film formation alone, a stacked structure of layers formed by mixing film formation, or a stacked structure of layers formed by film formation alone and layers formed by mixing film formation. These materials can be formed into a thin film by an evaporation method, and a spin coating method, an inkjet method, and the like.

[0115] The above-described material having a hole blocking property can also be used for the formation of the electron transport layer described below. That is, by using the above-described material known to have a hole blocking property, a layer serving as both a hole blocking layer and an electron transport layer can be formed.

[0116] As the electron transport layer of the organic electroluminescent device of the present application, a material known to have an electron transport property can be used. In addition to this, other compounds having an electron transport property can be used to form. For example, metal complexes of hydroxyquinoline derivatives such as Alq3, BAlq; various metal complexes; triazole derivatives; triazine derivatives; oxadiazole derivatives; pyridine derivatives; bis(10-hydroxybenzo[H]quinolinato)beryllium (Be(bq)2); benzimidazole derivatives such as 2-[4-(9,10-di-naphth-2-anthracen-2-yl)phenyl]-1-phenyl-1H-benzimidazole (ETL); thiazole derivatives; anthracene derivatives; carbodiimide derivatives; quinoxaline derivatives; pyridoindole derivatives; phenanthroline derivatives; thioxyl derivatives, and the like. They can be formed into a film alone, or can be used in the form of a single layer formed by mixing with other materials, or can be formed into a stacked structure of layers formed by film formation alone, a stacked structure of layers formed by mixing film formation, or a stacked structure of layers formed by film formation alone and layers formed by mixing film formation. These materials can be formed into a thin film by an evaporation method, and a spin coating method, an inkjet method, and the like.

[0117] As the electron injection layer of the organic electroluminescent device of the present application, a material known per se can be used to form. For example, alkali metal salts such as lithium fluoride, cesium fluoride; alkaline earth metal salts such as magnesium fluoride; metal complexes of hydroxyquinoline derivatives such as lithium hydroxyquinolinate; metal oxides such as aluminum oxide, and the like.

[0118] In the electron transport layer or the electron injection layer, materials generally used for the layer and further N-doped with a metal such as cesium, a triarylphosphine oxide derivative, or the like can be used.

[0119] As the cathode of the organic electroluminescent device of the present invention, it is preferred to use an electrode material with a low work function (such as aluminum, magnesium) or an alloy with a low work function (such as magnesium-silver alloy, magnesium-indium alloy, aluminum-magnesium alloy) as the electrode material.

[0120] As the substrate of the present invention, a conventional substrate of an organic light emitting device, such as glass or plastic, can be used. In the present invention, a glass substrate is selected.

[0121] The present invention is further described below with reference to specific examples. It should be understood that these examples are intended to illustrate the present invention only and are not intended to limit its scope. Experimental methods in the following examples, where specific conditions are not specified, were generally performed under conventional conditions or according to the manufacturer's recommendations. Unless otherwise defined, all professional and scientific terms used herein have the same meanings as those familiar to those skilled in the art. In addition, any methods and materials similar or equivalent to those described herein can be applied to the present invention. The preferred embodiments and materials described herein are for illustrative purposes only.

[0122] Example 1: Synthesis of Compound 1

[0123]

[0124] Synthesis of Compound M1: 2.5 g (10.0 mmol) of methyl 2-bromo-6-chlorobenzoate, 1.7 g (10.0 mmol) of 5-chloro-2-methylphenylboronic acid, 0.1 g (0.1 mmol) of tetrakis(triphenylphosphine)palladium (Pd(Ph3P)4), and 2.2 g (16.0 mmol) of potassium carbonate (K2CO3) were mixed with 60 mL of 1,4-dioxane and 8 mL of water in a 100 mL two-necked round-bottom flask. The mixture was stirred at 100°C under a nitrogen atmosphere for 12 hours. After the reaction, the mixture was cooled to room temperature, 60 mL of water was added, and the mixture was extracted with dichloromethane. The crude product (without further purification) was transferred to a 25 mL two-necked round-bottom flask, 10 mL of concentrated sulfuric acid was slowly added dropwise, and the mixture was stirred at 60°C for 2 hours. After cooling to room temperature, the mixture was poured into ice water and filtered through a fritted glass funnel. The filtrate was dried over anhydrous sodium sulfate and purified by silica gel column chromatography using petroleum ether and dichloromethane (volume ratio 5:1) as eluent to obtain 1.2 g of yellow solid product M1 in a yield of 45%. 1H NMR (400MHz, CDCl3) δ (ppm): 7.54 (d, J = 7.5Hz, 1H), 7.39 (t, J = 7.8Hz, 1H), 7.21 (d,J=8.0Hz,1H),7.17(d,J=8.2Hz,1H),7.10(d,J=8.2Hz,1H),2.55(s,3H).13C NMR(101MHz, CDCl3)δ(ppm):188.11,145.52,142.08,138.08,135.00,132.99,132.4 8,131.17,131.01,130.49,129.27,129.11,121.92,20.30.MS(ESI+)m / z:263.1[M+H] + .

[0125] Synthesis of Compound M2: In a 250 mL three-necked flask equipped with a reflux condenser and dropping funnel, 1.5 g (5.9 mmol) of iodine and 100 mL of glacial acetic acid were added under nitrogen and stirred to dissolve. Approximately 3.9 g (59 mmol) of hypophosphorous acid was then added and the temperature was raised to 120°C until the color of the system faded. Next, 3.9 g (14.8 mmol) of M1 was added all at once. After heating and reflux for 4 hours, the mixture was cooled to room temperature and poured into water to precipitate a large amount of white solid. This was filtered, washed with water, and dried to obtain 3.1 g of M2 as a white crystalline solid, with a yield of 84%. MS (ESI+): m / z: 249.0 [M+H] + . Anal.calcd for C 14 H 10 Cl2 (%): C 67.50, H 4.05; found: C 67.45, H 4.03.

[0126] Synthesis of Compound M3: 3.4 g (13.6 mmol) of the above-mentioned M2 solid was transferred to a 250 mL three-necked flask equipped with a dropping funnel. 100 mL of tetrahydrofuran was added under nitrogen, stirred to dissolve, and cooled in an ice-water bath. 4.0 g (41.7 mmol) of sodium tert-butoxide was added in an ice-water bath. Stirring was continued at this temperature for 10 minutes, followed by the addition of 5.9 g (41.7 mmol) of iodomethane. The system was stirred for 30 minutes, the ice bath was removed, and the system was allowed to warm to room temperature. The reaction was continued at room temperature overnight. After the reaction, insoluble matter was removed by filtration. The filtrate was concentrated and purified by column chromatography (350 mesh silica gel, eluent: petroleum ether:dichloromethane = 10:1 (v / v)) to obtain 3.5 g of M3 as white crystals, with a yield of 92%. MS (ESI+): m / z: 277.1 [M+H] + . Anal.calcd for C 16 H 14Cl2(%) : C 69.33, H 5.09; found: C 69.25, H 5.05.

[0127] Synthesis of compound 1: 0.55 g (2.0 mmol) of M3, 1.3 g (4.5 mmol) of 10-phenyl-9-anthraceneboronic acid, 0.02 g (0.1 mmol) of palladium acetate (Pd(OAc)2), 0.04 g (0.1 mmol) of S-Phos ligand and 0.8 g (3.0 mmol) of potassium phosphate tribasic (K2PO4·3H2O) were mixed with 100 mL of 1,4-dioxane, added to a 250 mL two-necked round-bottom flask and stirred at 100°C for 12 hours under nitrogen protection. After the reaction was completed, it was cooled to room temperature, filtered through a diatomite pad and the filtrate was directly concentrated. The collected crude product was directly purified by recrystallization with ethanol due to poor solubility, and 1.14 g of white solid was finally obtained with a yield of 80%. MS (ESI+): m / z: 713.2 [M+H] + Anal. calcd for C 56 H 40 (%) : C 94.34, H 5.66; found: C 94.32, H 5.65.

[0128] Synthesis example 1: synthesis of 10-boronic acid-10'-phenyl-9,9'-bianthracene

[0129]

[0130] 10 g of 10-bromo-10'-phenyl-9,9'-bianthracene was added to a reaction bottle, replaced with nitrogen, 80 mL of ultra-dry THF was added, cooled to -80°C, 12.9 mL of n-butyllithium (1.6 M) was added dropwise, and the temperature was kept at -80°C for 1 h, 4.6 mL of boronic acid triisopropyl ester was added, and the temperature was raised to 25°C for 2 h. After 1 h of reaction after adding dilute hydrochloric acid, it was stirred to crystallize. Filtration was performed to obtain 8.5 g of white solid with a yield of 91%. MS (ESI+): m / z 475.4 [M+H] + Anal. calcd for C 34 H 23 BO2(%) : C 86.09, H 4.89; found: C 86.05, H 4.88.

[0131] Referring to the synthesis route in reference example 1, and selecting the corresponding compound A, compound B and compound C, a series of specific compounds of the present application were prepared (see Table 1).

[0132] Table 1

[0133]

[0134] Device Example:

[0135] Example 10: Preparation of organic electroluminescent device 1 (organic EL device 1)

[0136] A hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light emitting layer 6, an electron transport layer 8, an electron injection layer 9 and a cathode 10 are sequentially formed on a transparent anode 2 pre-formed on a glass substrate 1 to prepare a Figure 1 The organic electroluminescent device shown (but without the hole blocking layer 7).

[0137] Specifically, a glass substrate with a 100 nm thick ITO film was ultrasonically treated in Decon 90 alkaline cleaning solution, rinsed in deionized water, cleaned three times in acetone and ethanol, baked in a clean environment until the water was completely removed, cleaned with ultraviolet light and ozone, and bombarded with a low-energy cation beam. The glass substrate with the ITO electrode was placed in a vacuum chamber and evacuated to 4×10 -4 -2×10 -5 Pa. Then, 97wt% HIL / 3wt% HTL was evaporated on the above-mentioned glass substrate with an ITO electrode at a evaporation rate of 0.2nm / s to form a layer with a thickness of 10nm, which served as a hole injection layer. On the hole injection layer, HTL was evaporated at a evaporation rate of 0.2nm / s to form a layer with a thickness of 40nm, which served as a hole transport layer. On the hole transport layer, EBL was evaporated at a evaporation rate of 0.2nm / s to form a layer with a thickness of 10nm, which served as an electron blocking layer. On the electron blocking layer, dual-source co-evaporation was performed at a evaporation rate of 0.2nm / s for the compound in Example 1 as the main material (Compound 1) and a evaporation rate of 0.008nm / s for BD1 as the doping material to form a layer with a thickness of 20nm, which served as a light-emitting layer, and the doping weight ratio of BD1 was 4wt%. ZADN-1 was deposited on the light-emitting layer at a rate of 0.2 nm / s to form a 45 nm thick layer, serving as an electron-transporting layer. Liq was then deposited on the electron-transporting layer at a rate of 0.02 nm / s to form a 2 nm thick layer, serving as an electron-injection layer. Finally, aluminum was deposited on the electron-injection layer at a rate of at least 0.5 nm / s to form a 100 nm thick cathode.

[0138] Examples 11-27: Preparation of Organic EL Devices 2-18

[0139] Referring to the preparation conditions of the organic EL device 1 in Example 10, and using the compounds corresponding to the layer structures in Table 2, organic EL devices 2-18 were prepared respectively.

[0140] Comparative Examples 1-6: Preparation of Organic EL Devices Comparative Examples 1-6

[0141] With reference to the preparation conditions of the organic EL device 1 in Example 9, and using the compounds corresponding to the layer structures in Table 2, organic EL device Comparative Examples 1-6 were prepared respectively.

[0142] Table 2 shows the structures and film thicknesses of the organic EL devices prepared in Examples 10-27 (Organic EL Devices 1-18) of the present invention and Comparative Examples 1-6 (Organic EL Device Comparative Examples 1-6).

[0143] Table 2

[0144]

[0145]

[0146] The compound structures involved in the device embodiments and comparative examples are as follows:

[0147]

[0148] The luminescence characteristics of the organic EL devices 1-18 prepared in Examples 10-27 and the organic EL devices 1-6 prepared in Comparative Examples 1-6 were measured under a DC voltage applied at room temperature in air. The current-luminance-voltage characteristics of the devices were measured using a Keithley source-measurement system (Keithley 2400 Sourcemeter, Keithley 2000 Currentmeter) equipped with a calibrated silicon photodiode. The electroluminescence spectra were measured using a Photo Research PR655 spectrometer. The external quantum efficiency of the devices was calculated using the method described in Adv. Mater., 2003, 15, 1043-1048. The measurement results are shown in Table 3.

[0149] Table 3

[0150]

[0151] As shown in Table 3, the compounds of the present invention have better device performance and lifespan when used as blue light host materials than the commercial material BH1; they also have better device performance and lifespan than the fluorene-based materials BH2 and BH3, further illustrating the performance advantages of the 1,8-dianthracene substituent. However, BH2 and BH3 show that shifting the phenyl substituent from the 4th position to the 8th position does not bring about any performance improvement.

[0152] The above describes the embodiments of the present invention. However, the present invention is not limited to the above embodiments. Any modifications, equivalent replacements, improvements, etc. made within the spirit and principles of the present invention shall be included in the scope of protection of the present invention.

Claims

1. A dianthrylfluorene compound having a structure represented by formula (I): in, Ar1 and Ar2 are the same or different and are independently selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; Ar3 and Ar4 are the same or different and are independently selected from substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C2-C30 heteroaryl; R1-R4 are the same or different and are independently selected from hydrogen, deuterium, tritium, halogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; or two adjacent R1s are linked together to form a substituted or unsubstituted ring, or two adjacent R2s are linked together to form a substituted or unsubstituted ring; L1-L4 are the same or different and are independently selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, or a substituted or unsubstituted C2-C30 heteroarylene group; n is the same or different and is independently selected from 0, 1, 2 or 3; m is the same or different and is independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8.

2. The compound according to claim 1, characterized in that The Ar1 and Ar2 are the same or different and are independently selected from one of the following structures: Among them, R 11 、R 12 are the same or different and are independently selected from hydrogen, deuterium, tritium, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C2-C18 heteroaryl; or two adjacent R 11 linked together to form substituted or unsubstituted rings; M is selected from O, S, CR 13 R 14 or NR 15 , the R 13 、R 14 、R 15 the same or different, independently selected from substituted or unsubstituted C-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C2-C18 heteroaryl; a1 is the same or different and is independently selected from 0, 1, 2, 3, 4 or 5; a2 is the same or different and is independently selected from 0, 1, 2, 3 or 4; a3 is the same or different and is independently selected from 0, 1, 2, 3, 4, 5, 6 or 7; a4 is the same or different and is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; a0 is the same or different and is independently selected from 0, 1 or 2.

3. The compound according to claim 1, characterized in that The Ar1 and Ar2 are the same or different and are independently selected from one of the following structures: Among them, R 11 、R 12 the same or different, independently selected from hydrogen, deuterium, tritium, fluorine, chlorine, bromine, iodine, substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyrenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, dibenzofuranyl, dibenzothiophenyl, 9-phenylcarbazolyl, 9-biphenylcarbazolyl, 9-naphthylcarbazolyl; R 21 the same or different, independently selected from hydrogen, deuterium, tritium, fluorine, chlorine, bromine, iodine, substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl; M is selected from O, S, CR 13 R 14 or NR 15 , the R 13 、R 14 The same or different, independently selected from substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, phenyl, biphenyl, naphthyl, dibenzofuranyl, dibenzothiophenyl; the R 15 Selected from substituted or unsubstituted: phenyl, biphenyl, naphthyl; Ar a 、Ar b the same or different, independently selected from substituted or unsubstituted: phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyrenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, dibenzofuranyl, dibenzothiophenyl, 9-phenylcarbazolyl, 9-biphenylcarbazolyl, 9-naphthylcarbazolyl; a1 is the same or different and is independently selected from 0, 1, 2, 3, 4 or 5; a2 is the same or different and is independently selected from 0, 1, 2, 3 or 4; a3 is the same or different and is independently selected from 0, 1, 2, 3, 4, 5, 6 or 7; a4 is the same or different and is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; a5 is the same or different and is independently selected from 0, 1, 2, 3, 4, 5 or 6; a6 is the same or different and is independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; a0 is the same or different and is independently selected from 0, 1 or 2.

4. The compound according to claim 1, characterized in that Ar3 and Ar4 are the same or different and are independently selected from substituted or unsubstituted methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, phenyl, biphenyl, naphthyl, dibenzofuranyl, and dibenzothiophenyl.

5. The compound according to claim 1, characterized in that The L1-L4 are the same or different and are independently selected from a single bond, or substituted or unsubstituted: phenylene, biphenylene, naphthylene, anthracene, pyridylene, pyrimidylene; preferably, the L1-L4 are the same or different and are independently selected from a single bond, or one of the following groups: Among them, R a is selected from hydrogen, deuterium, tritium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C14 aryl, substituted or unsubstituted C2-C12 heteroaryl; or two adjacent R a linked together to form a substituted or unsubstituted C6-C10 aromatic ring; b1 is the same or different and is independently selected from 0, 1, 2, 3 or 4; b2 is the same or different and is independently selected from 0, 1, 2 or 3; b3 is the same or different and is independently selected from 0, 1 or 2; b4 is the same or different and is independently selected from 0, 1, 2, 3, 4, 5 or 6; b5 is the same or different and is independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8.

6. The compound according to claim 1, characterized in that The R1-R4 are the same or different and are independently selected from hydrogen, deuterium, tritium, halogen, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C14 aryl, substituted or unsubstituted C2-C12 heteroaryl; or two adjacent R1s are connected together to form a substituted or unsubstituted C6-C10 aromatic ring, or two adjacent R2s are connected together to form a substituted or unsubstituted C6-C10 aromatic ring.

7. The compound according to claim 1, characterized in that The dianthrylfluorene compound has a structure shown in formula (I-1): wherein Ar5 is selected from substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; n1 is selected from 0, 1 or 2; Ar1-Ar4, R1-R4, L1-L4, n, m are as defined in claim 1; Preferably, the dianthrylfluorene compound has a structure shown in formula (I-2):

8. The compound according to claim 1, characterized in that The compound is selected from: 9 . A light-emitting device comprising a first electrode, a second electrode opposite to the first electrode, and at least one organic layer sandwiched between the first electrode and the second electrode, wherein the at least one organic layer comprises the dianthrylfluorene compound according to claim 1 .

10. The light emitting device according to claim 9, characterized in that The organic layer includes a light-emitting layer, and the light-emitting layer contains the dianthrylfluorene compound according to any one of claims 1 to 8.

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