Aromatic compound and organic electroluminescent device thereof

Abstract

The invention belongs to the technical field of organic photoelectric materials, and particularly relates to an aromatic compound and an organic electroluminescent device thereof. The aromatic compound provided by the invention has good planarity and film-forming property, meanwhile, the arrangement directions of molecules are relatively consistent, the light transmittance is also good, and the aromatic compound can be used as a covering layer material to be applied to an OLED device, so that the luminous efficiency of the device can be remarkably improved, and the service life of the device can be remarkably prolonged. In addition, the aromatic compound provided by the invention can also be used as an electron transport material, a hole blocking material or a light-emitting layer main body material, and can also improve the driving voltage, the light-emitting efficiency, the service life and the like of the device.

Description

Technical Field

[0001] This invention belongs to the field of organic optoelectronic materials technology, specifically relating to an aromatic compound and its organic electroluminescent device. Background Technology

[0002] Organic light-emitting diodes (OLEDs) have rapidly risen to prominence in the display and lighting fields due to their advantages such as high contrast, high resolution, wide viewing angle, fast response, and flexible display. OLEDs employ a multilayer thin-film structure, with each functional layer working synergistically to achieve efficient electroluminescence. In a typical structure, a transparent substrate (such as glass or a flexible polymer) is sequentially deposited with organic functional layers including a transparent anode (usually indium tin oxide, ITO), a hole injection layer (HIL), a hole transport layer (HTL), an emissive layer (EML), and an electron transport layer (ETL), ultimately covering a metal cathode. When a voltage is applied, holes injected from the anode and electrons injected from the cathode recombine in the emissive layer to form excitons. These excitons release energy as photons through radiative transitions, thereby generating visible light. This process constitutes the core working mechanism of OLED devices.

[0003] Based on the direction of light emission, OLEDs are mainly divided into two basic structures: bottom-emitting and top-emitting. Although bottom-emitting OLEDs have been commercialized first, their structural characteristic of requiring light to be emitted from a transparent substrate at the bottom makes the mechanical properties and light transmittance of the substrate the core challenges limiting their performance improvement and application expansion. In contrast, top-emitting OLEDs optimize the device structure by using a transparent cathode instead of the traditional opaque metal cathode, emitting light from the top of the device. This structure can effectively improve the light extraction efficiency of the device.

[0004] Since the development of top-emission OLEDs, improving light extraction efficiency has remained a core research topic and key challenge. Among numerous optimization strategies, the capping layer introduction strategy has attracted much attention due to its simple process and significant effects. Its mechanism of action is mainly reflected in two aspects: First, the capping layer effectively suppresses light reflection loss on the cathode surface through optical interference effects, significantly improving the effective transmittance of the cathode; second, by precisely controlling the material and thickness of the capping layer, a suitable refractive index gradient can be constructed, optimizing the optical matching at the device's emission end, thereby reducing light reflection loss at the interface. Therefore, developing novel capping layer materials with excellent performance has become crucial to breaking through the bottleneck of light extraction efficiency in top-emission OLEDs. Summary of the Invention

[0005] To solve the above-mentioned technical problems, the present invention provides an aromatic compound having the structure shown in formula (I):

[0006]

[0007] Wherein, ring A is selected from one of the following groups:

[0008]

[0009] The Ar1 is selected from one of the following groups:

[0010]

[0011] The Ar2 group is selected from one of the following groups:

[0012]

[0013] The ring B is selected from one of substituted or unsubstituted C6-C30 aromatic rings and substituted or unsubstituted C3-C30 heteroaromatic rings;

[0014] Each time u appears, it is selected from CR1 or N, either the same or different; each time v appears, it is selected from CR1' or N, either the same or different.

[0015] X is selected from O, S, or NR2; Y is selected from CR1 or N; Z is selected from O, S, CR3R4, or NR2; W is selected from O or S;

[0016] Each time R1 appears, it is selected from the same or different groups of the following: no hydrogen atom, deuterium atom, tritium atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 alkyl group, substituted or unsubstituted C3-C12 cycloalkyl group, substituted or unsubstituted silyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C3-C30 heteroaryl group, a monovalent group formed by fusion of a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, a monovalent group formed by fusion of a substituted or unsubstituted C3-C30 heteroaryl ring and a substituted or unsubstituted C3-C7 aliphatic ring, or a combination thereof.

[0017] Each time R2 appears, it is selected, either identically or differently, from one of the following: substituted or unsubstituted C1-C12 alkyl groups, substituted or unsubstituted C3-C12 cycloalkyl groups, substituted or unsubstituted silyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C3-C30 heteroaryl groups, a monovalent group formed by fusion of a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, a monovalent group formed by fusion of a substituted or unsubstituted C3-C30 heteroaryl ring and a substituted or unsubstituted C3-C7 aliphatic ring, or a combination thereof.

[0018] The R3 and R4 are independently selected from one of the following: substituted or unsubstituted C1-C12 alkyl groups, substituted or unsubstituted C3-C12 cycloalkyl groups, substituted or unsubstituted silyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C3-C30 heteroaryl groups, a monovalent group formed by fusion of a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, a monovalent group formed by fusion of a substituted or unsubstituted C3-C30 heteroaryl ring and a substituted or unsubstituted C3-C7 aliphatic ring, or combinations thereof; or R3 and R4 are linked together to form a ring.

[0019] The L1 is selected from one of the following: a single bond, a substituted or unsubstituted C6-C30 arylene group, a divalent group formed by the fusion of a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring; and combinations thereof.

[0020] The L2 is selected from one of the following: a single bond, a substituted or unsubstituted C6-C30 arylene, a substituted or unsubstituted C3-C30 heteroarylene, a divalent group formed by the fusion of a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, a divalent group formed by the fusion of a substituted or unsubstituted C3-C30 heteroaromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, or a combination thereof;

[0021] The L3 is selected from one of the following: a substituted or unsubstituted C6-C30 aryl group, a divalent group formed by the fusion of a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring;

[0022] The 'a' is selected from 0, 1, 2, or 3;

[0023] Each time R appears, it is selected from the same or different groups of hydrogen atom, deuterium atom, tritium atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 alkyl group, substituted or unsubstituted C3-C12 cycloalkyl group, substituted or unsubstituted silyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C3-C30 heteroaryl group, a monovalent group formed by fusion of a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, a monovalent group formed by fusion of a substituted or unsubstituted C3-C30 heteroaryl ring and a substituted or unsubstituted C3-C7 aliphatic ring, or a combination thereof.

[0024] The present invention also provides an organic electroluminescent device, comprising a cathode, an anode, and an organic layer, wherein the organic layer is located between the cathode and the anode, and the organic layer contains the aromatic compound described in the present invention.

[0025] The present invention also provides an organic electroluminescent device, comprising a cathode, an anode, an organic layer, and a capping layer, wherein the capping layer contains the aromatic compound described in the present invention.

[0026] Beneficial effects:

[0027] The aromatic compounds provided by this invention possess excellent planarity and film-forming properties, with relatively consistent molecular arrangement and good light transmittance. When used as a capping layer material in OLED devices, they can significantly improve the device's luminous efficiency and lifespan. Furthermore, the aromatic compounds provided by this invention can also be used as electron transport materials, hole blocking materials, or main materials for the luminescent layer, further improving the device's driving voltage, luminous efficiency, and lifespan. Detailed Implementation

[0028] The technical solutions of this invention will be clearly and completely described below with reference to specific embodiments. Obviously, the described embodiments are only a part of the embodiments of this invention, and not all of them. Based on the embodiments of this invention, all other embodiments obtained by those skilled in the art without creative effort are within the protection scope of this invention.

[0029] In the compounds of this invention, any atom not specified as a particular isotope includes any stable isotope of that atom, and comprises atoms at both their natural and non-natural isotopic abundances. Taking hydrogen as an example, each hydrogen atom in all naturally occurring compounds contains about 0.0156 atomic percent deuterium.

[0030] In this invention, the use of "H" and "hydrogen atom" refers to the presence of no more than the natural abundance of deuterium or tritium atoms in the chemical structure, for example, no more than 0.0156 atomic% of deuterium. "D" and "deuterium atom" refer to a deuterium abundance greater than the natural abundance, for example, any value exceeding 0.1 atomic%, 1 atomic%, or 10 atomic%, such as approximately 95 atomic% of deuterium. "T" and "tritium atom" refer to a tritium abundance greater than the natural abundance, for example, any value exceeding 0.1 atomic%, 1 atomic%, or 10 atomic%, such as approximately 95 atomic% of tritium. In this invention, the omission of undrawn hydrogen atoms signifies "H" or "hydrogen atom".

[0031] The halogen atom mentioned in this invention refers to fluorine, chlorine, bromine, and iodine atoms.

[0032] In this invention, "silyl group" refers to a -SiH3 group, and "substituted or unsubstituted silyl group" means that one or more H atoms on the silyl group are substituted or unsubstituted. The "substituted or unsubstituted silyl group" can be formed from -Si(R... k )3 indicates that each Rk The groups are selected, either identically or differently, from the following: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 alkenyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, fused cycloalcoholic groups of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic rings, and fused cycloalcoholic groups of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaryl rings. Preferably, each R k The groups are selected, either identically or differently, from the following: hydrogen, deuterium, substituted or unsubstituted C1-C30 alkyl groups, substituted or unsubstituted C3-C30 cycloalkyl groups, and substituted or unsubstituted C6-C60 aryl groups. The alkyl group preferably has 1 to 20 carbon atoms, more preferably 1 to 15, even more preferably 1 to 10, and most preferably 1 to 8. The cycloalkyl group preferably has 3 to 20 carbon atoms, more preferably 3 to 15, even more preferably 3 to 10, and most preferably 3 to 7. The aryl group preferably has 6 to 20 carbon atoms, more preferably 6 to 13, even more preferably 6 to 12, and most preferably 6 to 10. Preferably, each R... k The same or different groups are selected from the following: hydrogen, deuterium, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted heptyl, substituted or unsubstituted octyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted cycloheptyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinoline. Preferably, the substituted silane alkyl group specifically includes, but is not limited to, trimethylsilane alkyl, triethylsilane alkyl, triisopropylsilane alkyl, tri-tert-butylsilane alkyl, tert-butyldimethylsilane alkyl, vinyldimethylsilane alkyl, isopropyldimethylsilane alkyl, triphenylsilane alkyl, diphenylmethylsilane alkyl, phenyldimethylsilane alkyl, diphenylpyridylsilane alkyl, phenyldipyridylsilane alkyl, tripyridylsilane alkyl, etc. The aforementioned substituted silane alkyl group is preferably trimethylsilane alkyl, triethylsilane alkyl, triisopropylsilane alkyl, tri-tert-butylsilane alkyl, tert-butyldimethylsilane alkyl, isopropyldimethylsilane alkyl, triphenylsilane alkyl, diphenylmethylsilane alkyl, or phenyldimethylsilane alkyl.

[0033] The alkyl group described in this invention refers to a hydrocarbon group formed by removing one hydrogen atom from an alkane molecule. It can be a straight-chain alkyl group or a branched-chain alkyl group, preferably having 1 to 15 carbon atoms, more preferably 1 to 12 carbon atoms, and particularly preferably 1 to 6 carbon atoms. The straight-chain alkyl group includes methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, undecyl, dodecyl, etc., but is not limited thereto. The branched-chain alkyl group includes isopropyl, isobutyl, sec-butyl, tert-butyl, isomers of n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, etc., but is not limited thereto. The alkyl group is preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, or tert-butyl.

[0034] The cycloalkyl group described in this invention refers to a hydrocarbon group formed by removing one hydrogen atom from a cycloalkane molecule, preferably having 3 to 15 carbon atoms, more preferably 3 to 12 carbon atoms, and particularly preferably 5 to 10 carbon atoms. Examples may include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornane, etc., but are not limited thereto. The aforementioned cycloalkyl groups are preferably cyclopentane, cyclohexane, 1-adamantane, 2-adamantane, or norbornane.

[0035] The cycloalkenyl group described in this invention refers to a hydrocarbon group formed by removing one hydrogen atom from a cycloalkene molecule, preferably having 3 to 15 carbon atoms, more preferably 3 to 12 carbon atoms, and particularly preferably 5 to 10 carbon atoms. Examples may include cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, etc., but are not limited thereto. The cycloalkenyl groups described above are preferably cyclopentenyl or cyclohexenyl.

[0036] The heterocyclic alkyl group described in this invention refers to a group formed by removing one hydrogen atom from a heterocyclic molecule that contains at least one heteroatom in addition to carbon atoms. Heteroatoms include nitrogen, oxygen, sulfur, silicon, selenium, and phosphorus atoms, preferably nitrogen, oxygen, or sulfur. It is preferable to contain 1 to 3 heteroatoms, more preferably 1 to 2 heteroatoms, and particularly preferably 1 heteroatom. It is preferable to have 3 to 15 ring atoms, more preferably 3 to 12 ring atoms, and particularly preferably 5 to 6 ring atoms. Examples may include ethylene oxide, cyclothioethylene, propylidinyl, tetrahydropyrrolyl, piperidinyl, morpholinyl, thiomorpholinyl, piperazine, etc., but are not limited thereto. The aforementioned heterocyclic groups are preferably tetrahydropyrrolyl, piperidinyl, morpholinyl, thiomorpholinyl, or piperazine.

[0037] The aryl group mentioned in this invention refers to the general term for the monovalent group remaining after removing a hydrogen atom from the aromatic carbon atom of an aromatic compound molecule. It can be a monocyclic aryl, polycyclic aryl, or fused-ring aryl, preferably having 6 to 25 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 14 carbon atoms, and most preferably 6 to 12 carbon atoms. The monocyclic aryl group refers to an aryl group with only one aromatic ring in the molecule, such as phenyl, but not limited to this; the polycyclic aryl group refers to an aryl group with two or more independent aromatic rings in the molecule, such as biphenyl, terphenyl, etc., but not limited to this; the fused-ring aryl group refers to an aryl group with two or more aromatic rings in the molecule that are fused together by sharing two adjacent carbon atoms, such as naphthyl, anthracene, phenanthryl, pyrene, peryl, fluorenyl, benzo[a]fluorenyl, triphenylene, fluoranyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirodifluorenyl, spiro-cyclopentyl-fluorenyl, spiro-cyclohexyl-fluorenyl, spiro-adamantyl-fluorenyl, spiro-cyclopentenyl-fluorenyl, spiro-cyclohexenyl-fluorenyl, etc., but not limited to this. The aryl group is preferably phenyl, biphenyl, terphenyl, 1-naphthyl, 2-naphthyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirodifluorenyl, spiro-cyclopentyl-fluorenyl, spiro-cyclohexyl-fluorenyl, spiro-adamantyl-fluorenyl, spiro-cyclopentenyl-fluorenyl, or spiro-cyclohexenyl-fluorenyl.

[0038] The heteroaryl group described in this invention refers to the general term for groups obtained by replacing one or more aromatic carbon atoms in an aryl group with heteroatoms. The heteroatoms include, but are not limited to, oxygen, sulfur, nitrogen, silicon, selenium, or phosphorus atoms, preferably having 1 to 25 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 3 to 15 carbon atoms, and most preferably 3 to 12 carbon atoms. The linking site of the heteroaryl group can be located on a cyclic carbon atom or on a cyclic nitrogen atom. The heteroaryl group can be a monocyclic heteroaryl, a polycyclic heteroaryl, or a fused-ring heteroaryl. The monocyclic heteroaryl groups include furanyl, thiophene, pyrrole, imidazole, pyridinyl, pyrimidinyl, etc., but are not limited thereto; the polycyclic heteroaryl groups include phenylfuranyl, phenylthiophene, etc., but are not limited thereto; the fused-ring heteroaryl groups include benzothiophene, benzofuranyl, indolyl, benzoxazolyl, benzoimidazolyl, benzothiazolyl, dibenzofuranyl, benzodibenzofuranyl, dibenzothiophene, benzodibenzothiaphene, carbazolyl, benzocarbazolyl, acridinel, 9,10-dihydroacridinyl, phenoxazinyl, phenthiazinyl, phenoxthiazyl, quinolinyl, isoquinolinyl, quinoxolinyl, quinazolinyl, etc., but are not limited thereto. The aforementioned heteroaryl groups are preferably benzothiophene, benzofuran, indolyl, benzoxazolyl, benzoimidazolyl, benzothiazolyl, dibenzofuran, dibenzothiophene, carbazole, or pyridyl.

[0039] The monovalent group formed by the fusion of an aromatic ring and an aliphatic ring in this invention refers to the general term for a monovalent group remaining after removing one hydrogen atom from an aliphatic ring (cycloalkane, cycloene, cycloyne) fused with an aromatic ring. The aromatic ring preferably has 6 to 25 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 14 carbon atoms, and most preferably 6 to 12 carbon atoms. It may include benzene, naphthalene, anthracene, phenanthrene, etc., but is not limited thereto. The aliphatic ring preferably has 3 to 9 carbon atoms, more preferably 5 to 7 carbon atoms. It may include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopropene, cyclobutene, cyclopentene, cycloheptene, cyclopropyne, cyclobutyne, cyclopentyne, cyclohexyne, and cycloheptyne. Preferably, examples of monovalent groups formed by the fusion of aliphatic and aromatic rings may include, but are not limited to, benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, naphthocyclopropyl, naphthocyclobutyl, naphthocyclopentyl, and naphthocyclohexyl.

[0040] The monovalent group formed by the fusion of a heteroaromatic ring and an aliphatic ring in this invention refers to the general term for a monovalent group remaining after removing one hydrogen atom from an aliphatic ring (cycloalkanes, cycloalkenes, cycloalkynes) fused with a heteroaromatic ring. The heteroatom includes, but is not limited to, oxygen, sulfur, nitrogen, silicon, selenium, or phosphorus atoms, preferably having 1 to 25 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 3 to 15 carbon atoms, and most preferably 3 to 12 carbon atoms. It may include furanyl, thiophene, pyrrole, imidazolyl, pyridinyl, pyrimidine, benzothiophene, benzofuranyl, indole, benzoxazolyl, benzoimidazolyl, benzothiazolyl, dibenzofuranyl, benzodibenzofuranyl, dibenzothiophene, benzodi... Benzothiophene, carbazole, benzocarbazole, acridine, 9,10-dihydroacridinyl, phenoxazinyl, phenthiazinyl, phenoxthiayl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, etc., but not limited thereto; the aliphatic ring preferably has 3 to 9 carbon atoms, more preferably 5 to 7 carbon atoms, and may include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopropene, cyclobutene, cyclopentene, cycloheptene, cyclopropyne, cyclobutyne, cyclopentyne, cyclohexyne, cycloheptyne. Preferably, examples of monovalent groups formed by the fusion of an aliphatic ring and a heteroaromatic ring may include pyridocyclobutyl, pyridocyclopentyl, pyridocyclohexyl, pyridocyclopentenyl, pyridocyclohexenyl, pyrimidocyclopentyl, pyrimidocyclohexyl, etc., but not limited thereto.

[0041] In this invention, the term "arylene" refers to an aryl group having two bonding sites, i.e., a divalent group. The above description of aryl groups can be applied to it, the difference being that the arylene is a divalent group.

[0042] In this invention, the term "hybrid aryl" refers to a heteroaryl group having two bonding sites, i.e., a divalent group. The above description of heteroaryl groups can be applied to it, the difference being that the hybrid aryl group is a divalent group.

[0043] The divalent group formed by the fusion of an aromatic ring and an aliphatic ring as described in this invention refers to a group formed by the fusion of an aromatic ring and an aliphatic ring having two bonding sites, i.e., a divalent group. It can be applied to the above description of groups formed by the fusion of an aromatic ring and an aliphatic ring, the difference being that the divalent group formed by the fusion of an aromatic ring and an aliphatic ring is a divalent group.

[0044] The divalent group formed by the fusion of a heteroaromatic ring and an aliphatic ring as described in this invention refers to a group formed by the fusion of a heteroaromatic ring and an aliphatic ring having two bonding sites, i.e., a divalent group. The above description of groups formed by the fusion of a heteroaromatic ring and an aliphatic ring can be applied, the difference being that the divalent group formed by the fusion of a heteroaromatic ring and an aliphatic ring is a divalent group.

[0045] The term "substitution" as used in this invention refers to the replacement of a hydrogen atom in certain functional groups by another atom or functional group (i.e., a substituent), and the position of substitution is not limited, as long as the position is where the hydrogen atom is substituted. Furthermore, when two or more are substituted, the two or more substituents may be the same as or different from each other.

[0046] In this invention, "substituted or unsubstituted" means unsubstituted or substituted by one or more substituents selected from the group consisting of: deuterium, tritium, halogen, amino, cyano, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 cycloalkenyl, substituted or unsubstituted C3-C30 heterocycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 aryloxy, substituted or unsubstituted C2-C60 heteroaryl, substituted or unsubstituted silyl, preferably deuterium, halogen, cyano, nitro, C1-C12 alkyl, C3-C12 cycloalkyl, etc. C3-C12 cycloalkenyl, C3-C12 heterocycloalkyl, C6-C30 aryl, C2-C30 heteroaryl, substituted or unsubstituted silyl, wherein, when substituted by multiple substituents, the multiple substituents are the same or different from each other; preferably, it means unsubstituted or substituted by one or more substituents selected from the group consisting of: deuterium, fluorine, cyano, methyl, trifluoromethyl, deuterated methyl, ethyl, n-propyl, isopropyl, deuterated isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, deuterated tert-butyl, cyclopropane, methyl-substituted cyclopropane, ethyl-substituted cyclopropane, cyclobutane, methyl-substituted cyclobutane, ethyl-substituted cyclobutane, cyclopentane, methyl-substituted Cyclopentyl, ethyl-substituted cyclopentyl, cyclohexyl, methyl-substituted cyclohexyl, ethyl-substituted cyclohexyl, n-propyl-substituted cyclohexyl, n-butyl-substituted cyclohexyl, cyclohexane-substituted cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, adamantyl, methyl-substituted adamantyl, ethyl-substituted adamantyl, norbornyl, methyl-substituted norbornyl, ethyl-substituted norbornyl, tetrahydropyrrolyl, piperidinyl, morpholinyl, thiomorpholinyl, methyl-substituted piperazine, ethyl-substituted piperazine, phenyl-substituted piperazine, naphthyl-substituted piperazine, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, anthracene, deuterated anthracene, phenanthrene, deuterated phenanthrene, triphenylene The following substances are used: deuterated triphenylene, pyrene, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirodifluorenyl, spiro-cyclopentyl-fluorenyl, spiro-cyclohexyl-fluorenyl, spiro-adamantyl-fluorenyl, spiro-cyclopentenyl-fluorenyl, spiro-cyclohexenyl-fluorenyl, N-phenylcarbazolyl, benzofuranyl, benzothiophene, indolyl, dibenzofuranyl, benzodibenzofuranyl, dibenzothiophene, benzodibenzothiophene, benzoxazolyl, benzothiazolyl, pyridinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, trimethylsilyl, triphenylsilyl. When substituted with multiple substituents, the multiple substituents may be the same or different from each other, and two adjacent substituents may be linked together to form a ring.

[0047] In this specification, when the position of a substituent or linker site on the ring is not fixed, it means that it can be linked to any of the optional sites on the ring. For example, Can represent Can represent Can represent And so on.

[0048] In this specification, when a substituent or linking site lies within a bond that extends through two or more rings, it indicates that the substituent or linking site can be linked to any one of the two or more rings, specifically to any one of the corresponding optional sites within the ring. For example, Can represent Can represent Can represent And so on.

[0049] The linked ring structures described in this invention (e.g., forming saturated or unsaturated C3-C10 carbon rings, forming substituted or unsubstituted saturated or unsaturated C3-C6 aliphatic rings) refer to groups connected to each other by chemical bonds, optionally forming double / triple bonds, and can constitute aromatic groups, as shown in the following examples:

[0050]

[0051] In this invention, the ring formed by the connection can be an aromatic ring system, an aliphatic ring system, or a ring system formed by the fusion of the two. The ring formed by the connection can be a three-membered ring, a four-membered ring, a five-membered ring, a six-membered ring, a spiro ring, or a fused ring, such as benzene, naphthalene, indene, cyclopentene, cyclopentane, cyclopentanophenene, cyclohexene, cyclohexane, cyclohexanophenene, pyridine, quinoline, isoquinoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, phenanthrene, or pyrene, but is not limited thereto.

[0052] In this specification, "at least one" includes one, two, three, four, five, six, seven, eight or more.

[0053] The statement that a certain layer is located "above" another layer or electrode in this invention can be interpreted as being directly above another layer or electrode, or it can be that other layer structures exist in between.

[0054] The term "a certain layer" in this invention, which is "between" two layers, two electrodes, or one layer and an electrode, can be interpreted as the only layer structure between the two, or as having one or more layer structures between them.

[0055] This invention provides an aromatic compound having the structure shown in formula (I):

[0056]

[0057] Wherein, ring A is selected from one of the following groups:

[0058]

[0059] The Ar1 is selected from one of the following groups:

[0060]

[0061] The Ar2 group is selected from one of the following groups:

[0062]

[0063] The ring B is selected from one of substituted or unsubstituted C6-C30 aromatic rings and substituted or unsubstituted C3-C30 heteroaromatic rings;

[0064] Each time u appears, it is selected from CR1 or N, either the same or different; each time v appears, it is selected from CR1' or N, either the same or different.

[0065] X is selected from O, S, or NR2; Y is selected from CR1 or N; Z is selected from O, S, CR3R4, or NR2; W is selected from O or S;

[0066] Each time R1 appears, it is selected from the same or different groups of the following: no hydrogen atom, deuterium atom, tritium atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 alkyl group, substituted or unsubstituted C3-C12 cycloalkyl group, substituted or unsubstituted silyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C3-C30 heteroaryl group, a monovalent group formed by fusion of a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, a monovalent group formed by fusion of a substituted or unsubstituted C3-C30 heteroaryl ring and a substituted or unsubstituted C3-C7 aliphatic ring, or a combination thereof.

[0067] Each time R2 appears, it is selected, either identically or differently, from one of the following: substituted or unsubstituted C1-C12 alkyl groups, substituted or unsubstituted C3-C12 cycloalkyl groups, substituted or unsubstituted silyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C3-C30 heteroaryl groups, a monovalent group formed by fusion of a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, a monovalent group formed by fusion of a substituted or unsubstituted C3-C30 heteroaryl ring and a substituted or unsubstituted C3-C7 aliphatic ring, or a combination thereof.

[0068] The R3 and R4 are independently selected from one of the following: substituted or unsubstituted C1-C12 alkyl groups, substituted or unsubstituted C3-C12 cycloalkyl groups, substituted or unsubstituted silyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C3-C30 heteroaryl groups, a monovalent group formed by fusion of a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, a monovalent group formed by fusion of a substituted or unsubstituted C3-C30 heteroaryl ring and a substituted or unsubstituted C3-C7 aliphatic ring, or combinations thereof; or R3 and R4 are linked together to form a ring.

[0069] The L1 is selected from one of the following: a single bond, a substituted or unsubstituted C6-C30 arylene group, a divalent group formed by the fusion of a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring; and combinations thereof.

[0070] The L2 is selected from one of the following: a single bond, a substituted or unsubstituted C6-C30 arylene, a substituted or unsubstituted C3-C30 heteroarylene, a divalent group formed by the fusion of a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, a divalent group formed by the fusion of a substituted or unsubstituted C3-C30 heteroaromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, or a combination thereof;

[0071] The L3 is selected from one of the following: a substituted or unsubstituted C6-C30 aryl group, a divalent group formed by the fusion of a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring;

[0072] The 'a' is selected from 0, 1, 2, or 3;

[0073] Each time R appears, it is selected from the same or different groups of hydrogen atom, deuterium atom, tritium atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 alkyl group, substituted or unsubstituted C3-C12 cycloalkyl group, substituted or unsubstituted silyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C3-C30 heteroaryl group, a monovalent group formed by fusion of a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, a monovalent group formed by fusion of a substituted or unsubstituted C3-C30 heteroaryl ring and a substituted or unsubstituted C3-C7 aliphatic ring, or a combination thereof.

[0074] Preferably, the substituents in "substituted or unsubstituted" are independently selected from deuterium atom; fluorine atom; cyano group; methyl group substituted or unsubstituted by one or more of deuterium atom and fluorine atom; ethyl group; n-propyl group; isopropyl group substituted or unsubstituted by one or more of deuterium atom and fluorine atom; n-butyl group; sec-butyl group; isobutyl group; tert-butyl group substituted or unsubstituted by one or more of deuterium atom and fluorine atom; and groups substituted or unsubstituted by one or more of deuterium atom, methyl group, ethyl group, isopropyl group, and tert-butyl group. The following groups, substituted or unsubstituted, are included: cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornane; groups substituted or unsubstituted by one or more of the following: deuterium, fluorine, cyano, methyl, deuterated methyl, trifluoromethyl, ethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornane; phenyl. Naphthyl, anthracene, phenanthrene, phenylene, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirodifluorenyl, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, N-phenylcarbazoyl, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, benzoxazolyl, benzothiazolyl, benzocyclopropane, benzocyclobutane, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl; methyl, ethyl, n-propyl, isopropyl, n-butyl One or more of the following substituents, tert-butyl, phenyl, methyl-substituted phenyl, tert-butyl-substituted phenyl, fluorine-substituted phenyl, cyano-substituted phenyl, adamantyl-substituted phenyl, norbornel-substituted phenyl, naphthyl, anthraceneyl, phenanthrene, biphenyl, pyridyl, pyrimidinyl, dibenzofuranyl, dibenzothiopheneyl, and 9,9-dimethylfluorenyl, may be substituted or unsubstituted silyl groups, wherein when there are multiple substituents, the multiple substituents may be the same or different.

[0075] Preferably, the Ar1 is selected from one of the following groups:

[0076]

[0077] Wherein, each occurrence of a2 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; each occurrence of b2 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; each occurrence of c2 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; each occurrence of d2 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12; each occurrence of e2 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12. 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11; each time f2 appears, it is selected from 0, 1, 2, 3, or 4, either the same or different; each time g2 appears, it is selected from 0, 1, or 2, either the same or different; each time h2 appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, or 14, either the same or different; each time i2 appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, or 13, either the same or different.

[0078] Each time j2 appears, it is selected from 0, 1, 2, 3, 4, 5, or 6, either the same or different. Each time k2 appears, it is selected from 0, 1, 2, 3, 4, or 5, either the same or different. Each time l2 appears, it is selected from 0, 1, 2, or 3, either the same or different. Each time m2 appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, or 15, either the same or different. Each time n2 appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, or 17, either the same or different.

[0079] R1 is as described in this invention.

[0080] Preferably, each time R1 appears, it is selected from the following groups, either identically or differently: 0; hydrogen atom; deuterium atom; tritium atom; fluorine atom; cyano; trimethylsilyl; triphenylsilyl; dimethylphenylsilyl; methyl diphenylsilyl; methyl; deuterated methyl; trifluoromethyl; ethyl; n-propyl; isopropyl; deuterated isopropyl; n-butyl; isobutyl; sec-butyl; tert-butyl; deuterated tert-butyl; cyclopropane; cyclobutane; cyclopentane; cyclohexane; cycloheptane; adamantyl; [unspecified group] Borneyl; substituted with deuterium, fluorine, cyano, trimethylsilyl, triphenylsilyl, dimethylphenylsilyl, methyl diphenylsilyl, methyl, deuterated methyl, trifluoromethyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, deuterated tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantyl, norbornyl, phenyl, deuterated phenyl, methyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl The following are listed as substituted phenyl groups: trimethylsilyl-substituted phenyl groups, fluorine-substituted phenyl groups, cyano-substituted phenyl groups, naphthyl, anthraquinyl, phenanthryl, triphenylene, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiopheneyl, indolyl, benzoxazolyl, benzothiazolyl, benzoimidazolyl, dibenzofuranyl, dibenzothiopheneyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, and benzocycloheptane. The following groups, whether substituted or unsubstituted, are included: phenyl, biphenyl, naphthyl, anthracene, phenanthrene, triphenylene, fluorenyl, spirodifluorenyl, pyridyl, pyrimidinyl, triazine, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiopheneyl, indolyl, benzoxazolyl, benzothiazolyl, benzoimidazolyl, dibenzofuranyl, dibenzothiopheneyl, carbazoleyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, and benzocycloheptane.

[0081] Preferably, the Ar2 is selected from one of the following groups:

[0082]

[0083]

[0084] Wherein, each occurrence of a1 is selected from 0, 1, 2, 3, or 4; each occurrence of b1 is selected from 0, 1, 2, 3, 4, 5, or 6; each occurrence of c1 is selected from 0, 1, or 2; each occurrence of d1 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; each occurrence of e1 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; each occurrence of f1 is selected from 0, 1, 2, or 3; each occurrence of g1 is selected from 0, 1, 2, 3, 4, or 5; and each occurrence of h1 is selected from 0 or 1.

[0085] X and R1 are as described in this invention.

[0086] Preferably, the aforementioned Selected from one of the following groups:

[0087]

[0088]

[0089] X, R1, a1, b1, c1, d1, e1, f1, and g1 are all as described in this invention.

[0090] Preferably, L1 is selected from a single bond, such as one of the following groups:

[0091]

[0092] Preferably, the L2 is selected from a single bond group, such as the following groups:

[0093]

[0094] Preferably, the L3 is selected from one of the following groups:

[0095]

[0096] Wherein, the a 101 Each time it appears, it is selected from 0, 1, 2, 3, or 4, either identically or differently; the b mentioned 101 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, or 6, either identically or differently; the c mentioned 101 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8, either identically or differently; the d mentioned 101 Each time it appears, it is selected from 0, 1, or 2, either identically or differently; the e 101Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10, either identically or differently; the f mentioned 101 Each time it appears, it is selected from 0, 1, 2, or 3, either identically or differently; the g mentioned 101 Each time it appears, it is selected from 0, 1, 2, 3, 4 or 5, either the same or different.

[0097] The R mentioned 101 Each time it appears, it is selected from the same or different groups of hydrogen atom, deuterium atom, tritium atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 alkyl group, substituted or unsubstituted C3-C12 cycloalkyl group, substituted or unsubstituted silyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C3-C30 heteroaryl group, a monovalent group formed by fusion of a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, a monovalent group formed by fusion of a substituted or unsubstituted C3-C30 heteroaryl ring and a substituted or unsubstituted C3-C7 aliphatic ring, or a combination thereof;

[0098] The R mentioned 102 Each time it appears, it is selected from one of the following, either the same or different: hydrogen atom, deuterium atom, tritium atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 alkyl group, substituted or unsubstituted C3-C12 cycloalkyl group, or substituted or unsubstituted silyl group.

[0099] Preferably, the R 101Each time it appears, it is selected from the same or different groups: hydrogen atom; deuterium atom; tritium atom; fluorine atom; cyano group; trimethylsilyl; triphenylsilyl; dimethylphenylsilyl; methyl diphenylsilyl; methyl; deuterated methyl; trifluoromethyl; ethyl; n-propyl; isopropyl; deuterated isopropyl; n-butyl; isobutyl; sec-butyl; tert-butyl; deuterated tert-butyl; cyclopropane; cyclobutane; cyclopentane; cyclohexane; cycloheptane; adamantyl; norbornyl; deuterium atom Fungi, fluorine atom, cyano, trimethylsilyl, triphenylsilyl, dimethylphenylsilyl, methyl diphenylsilyl, methyl, deuterated phenyl, trifluoromethyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, deuterated tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantyl, norbornel alkyl, phenyl, deuterated phenyl, methyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl The phenyl group is substituted with one or more of the following: trimethylsilyl-substituted phenyl, fluorine-substituted phenyl, cyano-substituted phenyl, naphthyl, anthraquinyl, phenanthryl, triphenylene, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiophene, indolyl, benzoxazolyl, benzothiazolyl, benzoimidazolyl, dibenzofuranyl, dibenzothiaphene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, and benzocycloheptane. Or unsubstituted groups of the following: phenyl, biphenyl, naphthyl, anthracene, phenanthrene, triphenylene, fluorenyl, spirodifluorenyl, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiopheneyl, indolyl, benzoxazolyl, benzothiazolyl, benzoimidazolyl, dibenzofuranyl, dibenzothiapheneyl, carbazoleyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, and benzocycloheptane.

[0100] Preferably, the R 102 Each time it appears, it is selected from the following groups, either identically or differently: hydrogen atom; deuterium atom; tritium atom; fluorine atom; cyano group; trimethylsilyl group; triphenylsilyl group; dimethylphenylsilyl group; methyl diphenylsilyl group; methyl group; deuterated methyl group; trifluoromethyl group; ethyl group; n-propyl group; isopropyl group; deuterated isopropyl group; n-butyl group; isobutyl group; sec-butyl group; tert-butyl group; deuterated tert-butyl group; cyclopropane group; cyclobutane group; cyclopentane group; cyclohexane group; cycloheptane group; adamantane group; norbornene group.

[0101] Preferably, the aromatic compound has one of the structures shown in formulas (II-A) to (II-F):

[0102]

[0103]

[0104] Preferably, the aromatic compound is selected from one of the following compounds:

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131] The aromatic compounds represented by formula (I) of this invention can be prepared by the following synthetic route:

[0132]

[0133] Wherein, X, Y, ring A, Ar1, Ar2, L1, L2, L3, R, and a are as described in this invention; Q1, Q2, and Q3 are independently selected from fluorine atoms, chlorine atoms, bromine atoms, or iodine atoms; and G1, G2, and G3 are independently selected from B(OH)2 or...

[0134] Compound (Y1) can be reacted with compounds (Y2), (Y3), and (Y4) via a one-step, two-step, or three-step C-C coupling reaction to yield the target compound (I). There is no particular restriction on the reaction sequence of compound (Y1) with compounds (Y2), (Y3), and (Y4).

[0135] The above synthetic route employs reaction types commonly used in organic synthesis, and there are no particular limitations on reaction conditions (e.g., the selection, amount, order, and method of addition of reaction solvents, catalysts, ligands, bases, etc.). The above preparation method utilizes readily available raw materials, has a simple process, and yields excellent results. This invention can also employ other conventional reaction types in organic synthesis without particular limitations; the above are merely examples of synthetic routes.

[0136] The present invention also provides an organic electroluminescent device, comprising a cathode, an anode, and an organic layer, wherein the organic layer is located between the cathode and the anode, and the organic layer contains the aromatic compound described in the present invention.

[0137] The organic layer is located between the cathode and the anode, and the organic layer includes a hole transport region, a light-emitting layer, and an electron transport region.

[0138] Preferably, the electron transport region contains the aromatic compound described in this invention.

[0139] Preferably, the light-emitting layer comprises a host material and a dopant material, wherein the host material contains the aromatic compound described in this invention.

[0140] The present invention also provides an organic electroluminescent device, comprising a cathode, an anode, an organic layer, and a capping layer, wherein the capping layer contains the aromatic compound described in the present invention.

[0141] The hole transport region of the present invention includes at least one of a hole injection layer, a hole transport layer, and a light-emitting auxiliary layer. Preferably, the hole transport region includes a hole injection layer and a hole transport layer, wherein the hole injection layer is located between the anode and the light-emitting layer, and the hole transport layer is located between the hole injection layer and the light-emitting layer. Alternatively, the hole transport region includes a hole injection layer, a hole transport layer, and a light-emitting auxiliary layer, wherein the hole injection layer is located between the anode and the light-emitting layer, the hole transport layer is located between the hole injection layer and the light-emitting layer, and the light-emitting auxiliary layer is located between the hole transport layer and the light-emitting layer.

[0142] The hole injection layer described in this invention can be a monolayer structure composed of a single substance, or a monolayer or multilayer structure composed of different substances. Triarylamine compounds, porphyrin compounds, styrene compounds, polythiophene and its derivatives, phthalocyanine derivatives, axialene compounds, and other substances with high hole injection properties can be used, such as 4,4',4”-tris[2-naphthylphenylamino]triphenylamine (2-TNATA), 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazabenzenephenanthrene (HATCN), copper phthalocyanine (CuPC), 2,3,5,6-tetrafluoro-7,7',8,8'-tetracyanodimethyl-p-benzoquinone (F4-TCNQ), poly(3,4-ethylenedioxythiophene)-poly(styrenesulfonic acid) (PEDOT / PSS), compounds HT-1 to HT-18, compounds p-1 to p-4, but not limited to these.

[0143]

[0144]

[0145] The hole transport layer described in this invention can be a monolayer structure composed of a single material, or a monolayer or multilayer structure composed of different materials. Triarylamine compounds can be used, or other compounds with a hole mobility of 10... -6 cm 2 Substances with a concentration of / Vs or higher, such as N,N'-diphenyl-N,N'-di(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (NPB), 4,4'4"-tris(N,N-diphenylamino)triphenylamine (TDATA), and compounds HT-1 to HT-18 as shown above, but not limited thereto.

[0146] The light-emitting auxiliary layer described in this invention can be a single-layer structure composed of a single material, or a single-layer or multi-layer structure composed of different materials. Triarylamine compounds, spirofluorene derivatives, dibenzofuran derivatives, or other substances with suitable HOMO and T1 energy levels can be used. Examples include TPD, NPB, N4,N4-bis([1,1'-biphenyl]-4-yl)-N4'-phenylN4'-[1,1':4',1”-terphenyl]-4-yl-[1,1'-biphenyl]-4,4'-diamine, N-([1,1'-diphenyl]-4-yl)-N-(9,9-dimethyl-9H-furan-2-yl)-9,9'-spirodifluorene-2-amine, N,N-bis([1,1'-biphenyl]-4-yl)-3'-(dibenzo[b,d]furan-4-yl)-[1,1'-biphenyl]-4-amine, and compounds HT-1 to HT-18 as shown above, but not limited to these.

[0147] The luminescent layer of this invention comprises a guest material and a host material, and a dual-host material formed by two host materials can be used. The host material includes, but is not limited to, heterocyclic compounds, metal complexes, aromatic amine compounds, etc. Specific examples may include 4,4'-bis(carbazole-9-yl)biphenyl (CBP), 1,3-bis(N-carbazole)benzene (MCP), 1,3,5-tris(carbazole-9-yl)benzene (TCP), 9,10-bis(2-naphthyl)anthracene (ADN), etc., aromatic compounds of this invention, but are not limited to these. Preferably, the host material is selected from the aromatic compounds of this invention. The guest material includes, but is not limited to, aromatic amine derivatives, boron compounds, metal complexes, etc. Specific examples may include, but are not limited to, tri(2-phenylpyridine)iridium (Ir(ppy)3), di(1-phenyl-isoquinoline)(acetylacetone)iridium (Ir(piq)2(acac)), tri(1-phenyl-isoquinoline)iridium (Ir(piq)3), and 2,5,8,11-tetratert-butylperylene (TBPe).

[0148] The light-emitting layer of this invention may further include a sensitizer. The sensitizer refers to a material that enables the light-emitting material in the light-emitting layer to fully utilize electroexcitons, thereby improving the performance of the OLED device. In organic electroluminescent devices, the sensitizer may perform functions such as exciton trapping, exciton conversion, and exciton transfer. The sensitizer is mainly classified into phosphorescent sensitizers, TADF sensitizers, and excitocomplex sensitizers. Examples of phosphorescent sensitizers include iridium complexes and platinum complexes. TADF sensitizers mainly use TADF materials, and excitocomplex sensitizers consist of donor and acceptor materials.

[0149] The electron transport region of the present invention includes at least one of an electron injection layer, an electron transport layer, and a hole blocking layer. Preferably, the electron transport region includes an electron injection layer and an electron transport layer, wherein the electron injection layer is located between the cathode and the light-emitting layer, and the electron transport layer is located between the electron injection layer and the light-emitting layer. Preferably, the electron transport region includes an electron injection layer, an electron transport layer, and a hole blocking layer, wherein the electron injection layer is located between the cathode and the light-emitting layer, the electron transport layer is located between the electron injection layer and the light-emitting layer, and the hole blocking layer is located between the electron transport layer and the light-emitting layer.

[0150] The electron injection layer described in this invention can be a monolayer structure composed of a single substance, or a monolayer or multilayer structure composed of different substances. It can be one or more of the following substances: alkali metals, alkaline earth metals, alkali metal halides, alkaline earth metal halides, alkali metal oxides, alkaline earth metal oxides, alkali metal salts, alkaline earth metal salts, and other substances with high electron injection properties. Examples include Li, Ca, Sr, LiF, CsF, CaF2, BaO, Li2CO3, CaCO3, Li2C2O4, Cs2C2O4, CsAlF4, LiOx, Yb, Tb, etc., but are not limited to these.

[0151] The electron transport layer described in this invention can be a monolayer structure composed of a single substance, or a monolayer or multilayer structure composed of different substances. It can utilize high electron transport properties such as aluminum complexes, lithium complexes, beryllium complexes, zinc complexes, oxazole derivatives, benzoxazole derivatives, thiazole derivatives, benzothiazole derivatives, imidazole derivatives, benzimidazole derivatives, carbazole derivatives, phenanthroline derivatives, and polymeric compounds. Examples of electron transport materials for the electron transport layer include 8-hydroxyquinoline aluminum (Alq3), bis(10-hydroxybenzo[h]quinoline)beryllium (BeBq2), bis(2-methyl-8-hydroxyquinoline-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq), 2-(4-biphenyl)-5-phenyloxadiazole (PBD), and aromatic compounds described in this invention, but are not limited thereto. Preferably, the electron transport material is selected from the aromatic compounds described in this invention.

[0152] The hole blocking layer described in this invention can be a single-layer structure composed of a single material, or a single-layer or multi-layer structure composed of different materials. The hole blocking material used in the hole blocking layer requires a T1 energy level higher than that of the emissive layer to prevent energy loss from the emissive layer. Furthermore, the HOMO energy level of the hole blocking material must be lower than that of the host material of the emissive layer to effectively block holes. Further, the electron mobility of the hole blocking layer material used is 10... -6 cm 2A value of / Vs or higher facilitates electron transport. One or more of the following substances can be selected: aluminum complexes, lithium complexes, beryllium complexes, oxazole derivatives, benzoxazole derivatives, thiazole derivatives, benzothiazole derivatives, imidazole derivatives, benzimidazole derivatives, phenanthroline derivatives, and polymers. Examples include 1,3,5-tris(1-phenyl-1H-benzimidazol-2-yl)benzene (TPBI), BAlq, and the aromatic compounds described in this invention, but are not limited thereto. Preferably, the hole-blocking material is selected from the aromatic compounds described in this invention.

[0153] The anode described in this invention can be a reflective anode, such as a reflective film formed of silver (Ag), magnesium (Mg), aluminum (Al), gold (Au), nickel (Ni), chromium (Cr), ytterbium (Yb), or their alloys. It can also be a layered structure with a high work function that is transparent or semi-transparent, such as a layered structure formed of indium tin oxide (ITO), indium zinc oxide (ZnO), zinc oxide (ZnO), aluminum zinc oxide (AZO), indium gallium oxide (IGO), indium oxide (In2O3), or tin oxide (SnO2). The specific anode depends on the type of device to be fabricated. For example, if the device to be fabricated is a bottom-emitting device (emitting light from the anode side), a transparent or semi-transparent anode needs to be fabricated. If the device to be fabricated is a top-emitting device (emitting light from the cathode side), a reflective anode needs to be fabricated.

[0154] The cathode described in this invention can be a thin film with a low work function made of lithium, calcium, lithium fluoride / calcium, lithium fluoride / aluminum, aluminum, silver, magnesium, magnesium-silver alloy, etc. The thickness of the film can be adjusted to make a reflective electrode, a transparent electrode, or a semi-transparent electrode. If a bottom-emitting device is to be made, a reflective cathode needs to be made. If a top-emitting device is to be made, a transparent or semi-transparent cathode needs to be made.

[0155] The capping layer described in this invention can be a single-layer structure composed of a single substance, or a single-layer or multi-layer structure composed of different substances. The capping layer material can be an organic or inorganic substance with an appropriate refractive index, such as metal halides, oxides, nitrides, nitrogen oxides, sulfides, selenides, aromatic compounds, heteroaromatic compounds, aromatic amines, etc. Examples include LiF, CsF, MgF2, CaF2, CsCl, CuI, V2O5, WO3, MoO3, TiO2, ZrO, ZnO, SiO2, SiN, ZnS, Alq3, compound CP-1, compound CP-2, compound CP-3, compound CP-4, and the aromatic compounds described in this invention, but are not limited thereto. Preferably, the capping layer material is selected from the aromatic compounds described in this invention.

[0156]

[0157] The aforementioned organic layers, cathode, and anode can be prepared using any of the following methods: vacuum evaporation, inkjet printing, sputtering, plasma, ion plating, spin coating, immersion, screen printing, etc. There are no special limitations on the thickness of each layer, as long as good device performance is obtained.

[0158] The organic layers mentioned above are preferably prepared using vacuum evaporation, inkjet printing, or spin coating methods.

[0159] The thickness of each of the aforementioned organic layers is typically between 1 nanometer and 100 micrometers, preferably between 5 nanometers and 1000 nanometers, and more preferably between 5 nanometers and 200 nanometers. The thickness of the anode and cathode is adjusted according to the required transparency.

[0160] The organic electroluminescent device provided by this invention can be applied to lighting and display fields, specifically including smartphone displays, tablet displays, smart wearable device displays, large-size displays such as televisions, VR, and car taillights.

[0161] The technical solutions and effects of the present invention will be further described below with reference to embodiments and comparative examples.

[0162] The mass spectrometry of the compounds in this invention was performed using a G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer from Waters Instruments, UK, with chloroform as the solvent.

[0163] Elemental analysis was performed using a Vario EL cube organic elemental analyzer from Elementar GmbH, Germany, with sample masses ranging from 5 to 10 mg.

[0164] Synthesis Example 1: Synthesis of intermediates BB / DD / FF

[0165] Synthesis of intermediate BB-14:

[0166]

[0167] Under nitrogen protection, aa-14 (73.53 g, 300 mmol), bb-14 (69.46 g, 300 mmol), Pd(PPh3)4 (1.39 g, 1.2 mmol), and potassium carbonate (87.07 g, 630 mmol) were added to the reaction flask, followed by 2100 mL of a toluene / ethanol / water (2:1:1) mixture, and the mixture was refluxed for 6.5 hours. After the reaction was complete, the mixture was cooled to room temperature, quenched with water, extracted with dichloromethane, and the organic phases were combined. The organic phases were dried over anhydrous magnesium sulfate, filtered, and the filtrate was rotary evaporated and recrystallized from toluene to give cc-14 (58.26 g, 72% yield); HPLC purity ≥99.85%. Mass spectrometry m / z: 269.0617 (theoretical value: 269.0607).

[0168] Under nitrogen protection, cc-14 (67.43 g, 250 mmol), pinacol diboronate (69.34 g, 275.00 mmol), K₂CO₃ (44.92 g, 325.00 mmol), Pd(dppf)Cl₂ (0.91 g, 1.25 mmol), and 2175 mL of THF were added to a reaction flask, and the mixture was reacted under reflux for 6.5 hours. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the mixture was filtered. Recrystallization from toluene / n-hexane (5:1) yielded intermediate BB-14 (62.32 g, 69% yield). HPLC analysis showed a solid purity ≥ 99.87%. Mass spectrometry m / z: 361.1841 (theoretical value: 361.1849).

[0169] By substituting the raw materials according to the synthesis steps of intermediate BB-14, the intermediates shown in Table 1a can be obtained:

[0170] Table 1a

[0171]

[0172] Synthesis of intermediate DD-58:

[0173]

[0174] Under nitrogen protection, aa-58 (76.44 g, 250 mmol), pinacol diboronic acid ester (69.34 g, 275.00 mmol), K₂CO₃ (44.92 g, 325.00 mmol), Pd(dppf)Cl₂ (0.91 g, 1.25 mmol), and 2175 mL of THF were added to a reaction flask, and the mixture was reacted under reflux for 6.5 hours. After the reaction was completed, the mixture was cooled to room temperature, water was added, and the mixture was filtered. Recrystallization from toluene / n-hexane (5:1) yielded intermediate DD-58 (75.48 g, 76% yield). HPLC analysis showed a solid purity ≥ 99.81%. Mass spectrometry m / z: 397.1833 (theoretical value: 397.1849).

[0175] By substituting the raw materials according to the synthesis steps of intermediate DD-58, the intermediates shown in Table 2a can be obtained:

[0176] Table 2a

[0177]

[0178]

[0179] Synthesis Example 2: Synthesis of Compound 13

[0180]

[0181] Under nitrogen protection, AA-13 (27.03 g, 100 mmol), BB-13 (74.25 g, 200 mmol), potassium carbonate (41.46 g, 300 mmol), and palladium acetate (0.90 g, 4 mmol) were added to a reaction flask, followed by 1500 mL of a toluene / ethanol / water (2:1:1) mixture. The mixture was stirred and refluxed for 4.5 hours. After the reaction was complete, the reaction solution was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic phase was collected, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by vacuum distillation. Recrystallization from toluene / methanol (9:1 v / v) yielded intermediate CC-13 (43.73 g, 73% yield). HPLC analysis showed a solid purity ≥99.87%. Mass spectrometry m / z: 598.1439 (theoretical value: 598.1448).

[0182] Under nitrogen protection, CC-13 (5.99 g, 10 mmol), aa-170 (3.04 g, 10 mmol), potassium carbonate (2.07 g, 15 mmol), and Pd2(dba)3 (0.09 g, 0.1 mmol) were added to a reaction flask, followed by 100 mL of a toluene / ethanol / water (2:1:1) mixture. The mixture was stirred and refluxed for 6 hours. After the reaction was complete, the mixture was cooled to room temperature, quenched with water, extracted with dichloromethane, and the organic phases were combined. The organic phases were dried over anhydrous magnesium sulfate, filtered, and the filtrate was rotary evaporated and recrystallized from toluene to give compound 13 (5.26 g, yield 71%). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 740.2472 (theoretical value: 740.2464). Theoretical elemental content (%) C 54 H 32 N2O2: C, 87.55; H, 4.35; N, 3.78. Measured elemental content (%): C, 87.53; H, 4.36; N, 3.79.

[0183] Synthesis Example 3: Synthesis of Compound 14

[0184]

[0185] Replacing BB-13 with an equimolar amount of BB-14, and following the same steps as in Synthesis Example 2, yielded compound 14 (5.19 g, 72% yield). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 720.2765 (theoretical value: 720.2777). Theoretical elemental content (%) C 52 H 36N2O2: C, 86.64; H, 5.03; N, 3.89. Measured elemental content (%): C, 86.62; H, 5.05; N, 3.88.

[0186] Synthesis Example 4: Synthesis of Compound 16

[0187]

[0188] Under nitrogen protection, AA-16 (31.73 g, 100 mmol), BB-16 (34.42 g, 100 mmol), potassium carbonate (20.73 g, 150 mmol), and palladium acetate (0.45 g, 2 mmol) were added to a reaction flask, followed by 1000 mL of a toluene / ethanol / water (2:1:1) mixture. The mixture was stirred and refluxed for 4.5 hours. After the reaction was complete, the reaction solution was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic phase was collected, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by vacuum distillation. Recrystallization from toluene / methanol (9:1 v / v) yielded intermediate CC-16 (30.98 g, 76% yield). HPLC analysis showed a solid purity ≥99.86%. Mass spectrometry m / z: 405.9770 (theoretical value: 405.9760).

[0189] Under nitrogen protection, CC-16 (20.38 g, 50 mmol), DD-16 (16.06 g, 50 mmol), Pd(PPh3)4 (0.23 g, 0.2 mmol), and potassium carbonate (10.37 g, 75 mmol) were added to the reaction flask, followed by 500 mL of a toluene / ethanol / water (2:1:1) mixture. The mixture was refluxed for 6 hours. After the reaction was complete, the mixture was cooled to room temperature, quenched with water, extracted with dichloromethane, and the organic phases were combined. The organic phases were dried over anhydrous magnesium sulfate, filtered, and the filtrate was rotary evaporated and recrystallized from toluene to obtain EE-16 (19.31 g, 74%); HPLC purity ≥99.90%. Mass spectrometry m / z: 521.1169 (theoretical value: 521.1183).

[0190] Under nitrogen protection, EE-16 (5.22 g, 10 mmol), FF-16 (3.54 g, 10 mmol), potassium carbonate (2.07 g, 15 mmol), and Pd2(dba)3 (0.09 g, 0.1 mmol) were added to a reaction flask, followed by 100 mL of a toluene / ethanol / water (2:1:1) mixture. The mixture was stirred and refluxed for 6 hours. After the reaction was complete, the mixture was cooled to room temperature, quenched with water, extracted with dichloromethane, and the organic phases were combined. The organic phases were dried over anhydrous magnesium sulfate, filtered, and the filtrate was rotary evaporated and recrystallized from toluene to give compound 16 (5.07 g, yield 71%). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 713.2367 (theoretical value: 713.2355). Theoretical elemental content (%) C 53 H 31 NO2: C, 89.18; H, 4.38; N, 1.96. Measured elemental content (%): C, 89.16; H, 4.39; N, 1.93.

[0191] Synthesis Example 5: Synthesis of Compound 20

[0192]

[0193] By replacing BB-16 with an equimolar amount of BB-20 and DD-16 with an equimolar amount of DD-20, and following the same steps as in Synthesis Example 4, compound 20 (5.28 g, yield 74%) was obtained. HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 712.2412 (theoretical value: 712.2402). Theoretical elemental content (%) C 54 H 32 O2: C, 90.99; H, 4.52. Measured elemental content (%): C, 90.97; H, 4.53.

[0194] Synthesis Example 6: Synthesis of Compound 23

[0195]

[0196] By replacing BB-13 with an equimolar amount of BB-23 and aa-170 with an equimolar amount of FF-16, and following the same steps as in Synthesis Example 2, compound 23 (4.99 g, yield 69%) was obtained. HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 722.1858 (theoretical value: 722.1850). Theoretical elemental content (%) C 50 H 30N2S2: C, 83.07; H, 4.18; N, 3.88. Measured elemental content (%): C, 83.05; H, 4.19; N, 3.89.

[0197] Synthesis Example 7: Synthesis of Compound 24

[0198]

[0199] By replacing BB-16 with an equimolar amount of DD-16, and DD-16 with an equimolar amount of DD-20, and following the same steps as in Synthesis Example 4, compound 24 (5.10 g, yield 74%) was obtained. HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 689.2347 (theoretical value: 689.2355). Theoretical elemental content (%) C 51 H 31 NO2: C, 88.80; H, 4.53; N, 2.03. Measured elemental content (%): C, 88.81; H, 4.52; N, 2.05.

[0200] Synthesis Example 8: Synthesis of Compound 55

[0201]

[0202] By replacing BB-16 with an equimolar amount of BB-55 and FF-16 with an equimolar amount of FF-55, and following the same steps as in Synthesis Example 4, compound 55 (5.53 g, yield 74%) was obtained. HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 746.2946 (theoretical value: 746.2933). Theoretical elemental content (%) C 54 H 38 N2O2: C, 86.84; H, 5.13; N, 3.75. Measured elemental content (%): C, 86.83; H, 5.15; N, 3.77.

[0203] Synthesis Example 9: Synthesis of Compound 58

[0204]

[0205] By replacing BB-16 with an equimolar amount of BB-58 and DD-16 with an equimolar amount of DD-58, and following the same steps as in Synthesis Example 4, compound 58 (5.69 g, yield 72%) was obtained. HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 790.2631 (theoretical value: 790.2620). Theoretical elemental content (%) C 58 H 34N2O2: C, 88.08; H, 4.33; N, 3.54. Measured elemental content (%): C, 88.09; H, 4.31; N, 3.55.

[0206] Synthesis Example 10: Synthesis of Compound 79

[0207]

[0208] Replacing BB-16 with an equimolar amount of BB-79, and following the same steps as in Synthesis Example 4, yielded compound 79 (4.86 g, yield 68%). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 714.2319 (theoretical value: 714.2307). Theoretical elemental content (%) C 52 H 30 N2O2: C, 87.37; H, 4.23; N, 3.92. Measured elemental content (%): C, 87.39; H, 4.22; N, 3.91.

[0209] Synthesis Example 11: Synthesis of Compound 82

[0210]

[0211] By replacing BB-16 with an equimolar amount of BB-82 and DD-16 with an equimolar amount of DD-82, and following the same steps as in Synthesis Example 4, compound 82 (5.70 g, 70% yield) was obtained. HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 813.2655 (theoretical value: 813.2668). Theoretical elemental content (%) C 61 H 35 NO2: C, 90.01; H, 4.33; N, 1.72. Measured elemental content (%): C, 90.03; H, 4.34; N, 1.75.

[0212] Synthesis Example 12: Synthesis of Compound 87

[0213]

[0214] Replacing DD-16 with an equimolar amount of DD-20 and FF-16 with an equimolar amount of FF-87, while adhering to the same steps as in Synthesis Example 4, yielded compound 87 (5.13 g, 73% yield). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 702.2025 (theoretical value: 702.2017). Theoretical elemental content (%) C 52 H 30OS: C, 88.86; H, 4.30. Measured elemental content (%): C, 88.84; H, 4.32.

[0215] Synthesis Example 13: Synthesis of Compound 108

[0216]

[0217] By replacing BB-16 with an equimolar amount of BB-108, DD-16 with an equimolar amount of DD-108, and FF-16 with an equimolar amount of FF-108, and following the same steps as in Synthesis Example 4, compound 108 (5.34 g, yield 76%) was obtained. HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 702.2009 (theoretical value: 702.2017). Theoretical elemental content (%) C 52 H 30 OS: C, 88.86; H, 4.30. Measured elemental content (%): C, 88.84; H, 4.31.

[0218] Synthesis Example 14: Synthesis of Compound 120

[0219]

[0220] By replacing BB-13 with an equimolar amount of BB-120 and aa-170 with an equimolar amount of FF-120, and following the same steps as in Synthesis Example 2, compound 120 (5.06 g, 70% yield) was obtained. HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 722.1841 (theoretical value: 722.1850). Theoretical elemental content (%) C 50 H 30 N2S2: C, 83.07; H, 4.18; N, 3.88. Measured elemental content (%): C, 83.05; H, 4.17; N, 3.86.

[0221] Synthesis Example 15: Synthesis of Compound 127

[0222]

[0223] By replacing BB-16 with an equimolar amount of DD-16, DD-16 with an equimolar amount of DD-127, and FF-16 with an equimolar amount of FF-120, and following the same steps as in Synthesis Example 4, compound 127 (5.45 g, yield 73%) was obtained. HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 745.2973 (theoretical value: 745.2981). Theoretical elemental content (%) C 55 H 39NO2: C, 88.56; H, 5.27; N, 1.88. Measured elemental content (%): C, 88.54; H, 5.28; N, 1.85.

[0224] Synthesis Example 16: Synthesis of Compound 147

[0225]

[0226] By replacing BB-13 with an equimolar amount of DD-16 and aa-170 with an equimolar amount of FF-147, and following the same steps as in Synthesis Example 2, compound 147 (5.33 g, yield 72%) was obtained. HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 740.2473 (theoretical value: 740.2464). Theoretical elemental content (%) C 54 H 32 N2O2: C, 87.55; H, 4.35; N, 3.78. Measured elemental content (%): C, 87.56; H, 4.33; N, 3.76.

[0227] Synthesis Example 17: Synthesis of Compound 170

[0228]

[0229] By replacing BB-16 with an equimolar amount of BB-23 and FF-16 with an equimolar amount of FF-170, and following the same steps as in Synthesis Example 4, compound 170 (5.06 g, yield 69%) was obtained. HPLC analysis showed a solid purity ≥ 99.92%. Mass spectrometry m / z: 732.2226 (theoretical value: 732.2235). Theoretical elemental content (%) C 52 H 32 N₂OS: C, 85.22; H, 4.40; N, 3.82. Measured elemental content (%): C, 85.23; H, 4.41; N, 3.80.

[0230] Synthesis Example 18: Synthesis of Compound 197

[0231]

[0232] By replacing BB-13 with an equimolar amount of BB-16 and aa-170 with an equimolar amount of FF-197, and following the same steps as in Synthesis Example 2, compound 197 (4.90 g, yield 68%) was obtained. HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 720.2702 (theoretical value: 720.2715). Theoretical elemental content (%) C 52 H 28D4N2O2: C, 86.64; H, 5.03; N, 3.89. Measured elemental content (%): C, 86.62; H, 5.02; N, 3.86.

[0233] Synthesis Example 19: Synthesis of Compound 199

[0234]

[0235] By replacing BB-16 with an equimolar amount of DD-16, DD-16 with an equimolar amount of DD-199, and FF-16 with an equimolar amount of FF-170, and following the same steps as in Synthesis Example 4, compound 199 (5.10 g, yield 71%) was obtained. HPLC analysis showed a solid purity ≥ 99.92%. Mass spectrometry m / z: 717.2424 (theoretical value: 717.2416). Theoretical elemental content (%) C 51 H 31 N3O2: C, 85.34; H, 4.35; N, 5.85. Measured elemental content (%): C, 85.35; H, 4.33; N, 5.83.

[0236] Synthesis Example 20: Synthesis of Compound 235

[0237]

[0238] By replacing BB-16 with an equimolar amount of aa-14, DD-16 with an equimolar amount of DD-58, and FF-16 with an equimolar amount of FF-170, and following the same steps as in Synthesis Example 4, compound 235 (5.23 g, yield 73%) was obtained. HPLC analysis showed a solid purity ≥ 99.91%. Mass spectrometry m / z: 716.2455 (theoretical value: 716.2464). Theoretical elemental content (%) C 52 H 32 N2O2: C, 87.13; H, 4.50; N, 3.91. Measured elemental content (%): C, 87.11; H, 4.52; N, 3.90.

[0239] Synthesis Example 21: Synthesis of Compound 256

[0240]

[0241] By replacing BB-13 with an equimolar amount of DD-16 and aa-170 with an equimolar amount of FF-256, and following the same steps as in Synthesis Example 2, compound 256 (5.52 g, yield 72%) was obtained. HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 766.2611 (theoretical value: 766.2620). Theoretical elemental content (%) C 56 H 34 N2O2: C, 87.71; H, 4.47; N, 3.65. Measured elemental content (%): C, 87.70; H, 4.48; N, 3.67.

[0242] Synthesis Example 22: Synthesis of Compound 263

[0243]

[0244] By replacing BB-16 with an equimolar amount of BB-23 and FF-16 with an equimolar amount of FF-263, and following the same steps as in Synthesis Example 4, compound 263 (5.48 g, 70% yield) was obtained. HPLC analysis showed a solid purity ≥ 99.92%. Mass spectrometry m / z: 782.2384 (theoretical value: 782.2392). Theoretical elemental content (%) C 56 H 34 N₂OS: C, 85.91; H, 4.38; N, 3.58. Measured elemental content (%): C, 85.92; H, 4.36; N, 3.55.

[0245] Synthesis Example 23: Synthesis of Compound 299

[0246]

[0247] By replacing BB-13 with an equimolar amount of DD-16 and aa-170 with an equimolar amount of FF-299, and following the same steps as in Synthesis Example 2, compound 299 (6.32 g, yield 75%) was obtained. HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 842.2945 (theoretical value: 842.2933). Theoretical elemental content (%) C 62 H 38 N2O2: C, 88.34; H, 4.54; N, 3.32. Measured elemental content (%): C, 88.33; H, 4.56; N, 3.35.

[0248] Synthesis Example 24: Synthesis of Compound 301

[0249]

[0250] DD-16 was replaced with an equimolar amount of DD-301, and FF-16 was replaced with an equimolar amount of FF-256. All other steps were the same as in Synthesis Example 4, yielding compound 301 (6.14 g, 71% yield). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 864.3149 (theoretical value: 864.3141). Theoretical elemental content (%) C 65 H 40 N₂O: C, 90.25; H, 4.66; N, 3.24. Measured elemental content (%): C, 90.26; H, 4.67; N, 3.21.

[0251] Synthesis Example 25: Synthesis of Compound 307

[0252]

[0253] By replacing BB-16 with an equimolar amount of BB-20 and FF-16 with an equimolar amount of FF-256, and following the same steps as in Synthesis Example 4, compound 307 (5.53 g, 70% yield) was obtained. HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 789.2679 (theoretical value: 789.2668). Theoretical elemental content (%) C 59 H 35 NO2: C, 89.71; H, 4.47; N, 1.77. Measured elemental content (%): C, 89.74; H, 4.45; N, 1.76.

[0254] Synthesis Example 26: Synthesis of Compound 312

[0255]

[0256] By replacing BB-16 with an equimolar amount of BB-312 and FF-16 with an equimolar amount of FF-256, and following the same steps as in Synthesis Example 4, compound 312 (5.92 g, yield 75%) was obtained. HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 789.2654 (theoretical value: 789.2668). Theoretical elemental content (%) C 59 H 35 NO2: C, 89.71; H, 4.47; N, 1.77. Measured elemental content (%): C, 89.73; H, 4.45; N, 1.76.

[0257] Synthesis Example 27: Synthesis of Compound 338

[0258]

[0259] By replacing DD-16 with an equimolar amount of DD-338 and FF-16 with an equimolar amount of FF-256, and following the same steps as in Synthesis Example 4, compound 338 (5.88 g, yield 74%) was obtained. HPLC analysis showed a solid purity ≥ 99.92%. Mass spectrometry m / z: 793.2910 (theoretical value: 793.2919). Theoretical elemental content (%) C 59 H 31 D4NO2: C, 89.26; H, 4.95; N, 1.76. Measured elemental content (%): C, 89.27; H, 4.93; N, 1.77.

[0260] Synthesis Example 28: Synthesis of Compound 343

[0261]

[0262] By replacing BB-16 with an equimolar amount of BB-343, DD-16 with an equimolar amount of DD-343, and FF-16 with an equimolar amount of FF-256, and following the same steps as in Synthesis Example 4, compound 343 (6.10 g, yield 69%) was obtained. HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 883.2826 (theoretical value: 883.2835). Theoretical elemental content (%) C 63 H 37 N3O3: C, 85.60; H, 4.22; N, 4.75. Measured elemental content (%): C, 85.61; H, 4.23; N, 4.72.

[0263] Synthesis Example 29: Synthesis of Compound 368

[0264]

[0265] By replacing BB-16 with an equimolar amount of BB-108, DD-16 with an equimolar amount of DD-368, and FF-16 with an equimolar amount of FF-256, and following the same steps as in Synthesis Example 4, compound 368 (6.43 g, yield 71%) was obtained. HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 904.2985 (theoretical value: 904.2977). Theoretical elemental content (%) C 68 H 40 O3: C, 90.24; H, 4.45. Measured elemental content (%): C, 90.26; H, 4.42.

[0266] Synthesis Example 30: Synthesis of Compound 392

[0267]

[0268] By replacing BB-16 with an equimolar amount of DD-20 and FF-16 with an equimolar amount of FF-392, and following the same steps as in Synthesis Example 4, compound 392 (5.67 g, yield 74%) was obtained. HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 765.2677 (theoretical value: 765.2668). Theoretical elemental content (%) C 57 H 35 NO2: C, 89.39; H, 4.61; N, 1.83. Measured elemental content (%): C, 89.37; H, 4.60; N, 1.85.

[0269] Synthesis Example 31: Synthesis of Compound 411

[0270]

[0271] By replacing BB-16 with an equimolar amount of DD-16, DD-16 with an equimolar amount of DD-411, and FF-16 with an equimolar amount of FF-411, and following the same steps as in Synthesis Example 4, compound 411 (5.45 g, yield 71%) was obtained. HPLC analysis showed a solid purity ≥ 99.92%. Mass spectrometry m / z: 767.2565 (theoretical value: 767.2573). Theoretical elemental content (%) C 55 H 33 N3O2: C, 86.03; H, 4.33; N, 5.47. Measured elemental content (%): C, 86.04; H, 4.35; N, 5.44.

[0272] Synthesis Example 32: Synthesis of Compound 417

[0273]

[0274] By replacing BB-16 with an equimolar amount of DD-16, DD-16 with an equimolar amount of DD-417, and FF-16 with an equimolar amount of BB-312, and following the same steps as in Synthesis Example 4, compound 417 (4.94 g, yield 69%) was obtained. HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 715.2502 (theoretical value: 715.2511). Theoretical elemental content (%) C 53 H 33 NO2: C, 88.93; H, 4.65; N, 1.96. Measured elemental content (%): C, 88.94; H, 4.63; N, 1.95.

[0275] Synthesis Example 33: Synthesis of Compound 419

[0276]

[0277] By replacing BB-13 with an equimolar amount of BB-419 and aa-170 with an equimolar amount of FF-419, and following the same steps as in Synthesis Example 2, compound 419 (6.22 g, yield 74%) was obtained. HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 840.2763 (theoretical value: 840.2777). Theoretical elemental content (%) C 62 H 36 N2O2: C, 88.55; H, 4.31; N, 3.33. Measured elemental content (%): C, 88.53; H, 4.32; N, 3.31.

[0278] Synthesis Example 34: Synthesis of Compound 440

[0279]

[0280] By replacing BB-13 with an equimolar amount of BB-440 and aa-170 with an equimolar amount of DD-417, and following the same steps as in Synthesis Example 2, compound 440 (6.08 g, yield 72%) was obtained. HPLC analysis showed a solid purity ≥ 99.91%. Mass spectrometry m / z: 844.3081 (theoretical value: 844.3090). Theoretical elemental content (%) C 62 H 40 N2O2: C, 88.13; H, 4.77; N, 3.32. Measured elemental content (%): C, 88.15; H, 4.76; N, 3.31.

[0281] Synthesis Example 35: Synthesis of Compound 457

[0282]

[0283] By replacing AA-13 with an equimolar amount of AA-457, BB-13 with an equimolar amount of DD-16, and aa-170 with an equimolar amount of FF-170, and following the same steps as in Synthesis Example 2, compound 457 (5.09 g, yield 71%) was obtained. HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 716.2473 (theoretical value: 716.2464). Theoretical elemental content (%) C 52 H 32 N2O2: C, 87.13; H, 4.50; N, 3.91. Measured elemental content (%): C, 87.15; H, 4.51; N, 3.90.

[0284] Synthesis Example 36: Synthesis of Compound 469

[0285]

[0286] By replacing AA-16 with an equimolar amount of AA-469 and FF-16 with an equimolar amount of FF-256, and following the same steps as in Synthesis Example 4, compound 469 (5.53 g, 70% yield) was obtained. HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 789.2677 (theoretical value: 789.2668). Theoretical elemental content (%) C 59 H 35 NO2: C, 89.71; H, 4.47; N, 1.77. Measured elemental content (%): C, 89.75; H, 4.45; N, 1.76.

[0287] Synthesis Example 37: Synthesis of Compound 480

[0288]

[0289] By replacing AA-16 with an equimolar amount of AA-480 and BB-16 with an equimolar amount of BB-480, and following the same steps as in Synthesis Example 4, compound 480 (5.69 g, yield 72%) was obtained. HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 789.2679 (theoretical value: 789.2668). Theoretical elemental content (%) C 59 H 35 NO2: C, 89.71; H, 4.47; N, 1.77. Measured elemental content (%): C, 89.72; H, 4.45; N, 1.79.

[0290] Synthesis Example 38: Synthesis of Compound 498

[0291]

[0292] By replacing BB-16 with an equimolar amount of DD-16, and DD-16 with an equimolar amount of DD-498, and following the same steps as in Synthesis Example 4, compound 498 (5.60 g, yield 73%) was obtained. HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 766.2629 (theoretical value: 766.2620). Theoretical elemental content (%) C 56 H 34 N2O2: C, 87.71; H, 4.47; N, 3.65. Measured elemental content (%): C, 87.70; H, 4.49; N, 3.66.

[0293] Synthesis Example 39: Synthesis of Compound 501

[0294]

[0295] By replacing BB-16 with an equimolar amount of BB-501 and DD-16 with an equimolar amount of DD-501, and following the same steps as in Synthesis Example 4, compound 501 (5.72 g, yield 72%) was obtained. HPLC analysis showed a solid purity ≥ 99.91%. Mass spectrometry m / z: 793.2929 (theoretical value: 793.2919). Theoretical elemental content (%) C 59 H 31 D4NO2: C, 89.26; H, 4.95; N, 1.76. Measured elemental content (%): C, 89.23; H, 4.97; N, 1.73.

[0296] Synthesis Example 40: Synthesis of Compound 536

[0297]

[0298] By replacing BB-13 with an equimolar amount of BB-23 and aa-170 with an equimolar amount of FF-536, and following the same steps as in Synthesis Example 2, compound 536 (5.67 g, yield 71%) was obtained. HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 798.2172 (theoretical value: 798.2163). Theoretical elemental content (%) C 56 H 34 N2S2: C, 84.18; H, 4.29; N, 3.51. Measured elemental content (%): C, 84.17; H, 4.28; N, 3.53.

[0299] Synthesis Example 41: Synthesis of Compound 559

[0300]

[0301] By replacing BB-13 with an equimolar amount of BB-16 and aa-170 with an equimolar amount of FF-559, and following the same steps as in Synthesis Example 2, compound 559 (5.90 g, 70% yield) was obtained. HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 842.2945 (theoretical value: 842.2933). Theoretical elemental content (%) C 62 H 38 N2O2: C, 88.34; H, 4.54; N, 3.32. Measured elemental content (%): C, 88.35; H, 4.55; N, 3.31.

[0302] Synthesis Example 42: Synthesis of Compound 654

[0303]

[0304] By replacing BB-13 with an equimolar amount of BB-23 and aa-170 with an equimolar amount of FF-654, and following the same steps as in Synthesis Example 2, compound 654 (5.86 g, yield 71%) was obtained. HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 824.2328 (theoretical value: 824.2320). Theoretical elemental content (%) C 58 H 36 N2S2: C, 84.43; H, 4.40; N, 3.40. Measured elemental content (%): C, 84.42; H, 4.41; N, 3.43.

[0305] Synthesis Example 43: Synthesis of Compound 751

[0306]

[0307] By replacing BB-16 with an equimolar amount of BB-23, DD-16 with an equimolar amount of DD-751, and FF-16 with an equimolar amount of FF-751, and following the same steps as in Synthesis Example 4, compound 751 (5.72 g, yield 74%) was obtained. HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 772.2017 (theoretical value: 772.2007). Theoretical elemental content (%) C 54 H 32 N2S2: C, 83.91; H, 4.17; N, 3.62. Measured elemental content (%): C, 83.92; H, 4.15; N, 3.63.

[0308] Synthesis Example 44: Synthesis of Compound 760

[0309]

[0310] By replacing BB-13 with an equimolar amount of BB-23 and aa-170 with an equimolar amount of FF-760, and following the same steps as in Synthesis Example 2, compound 760 (5.40 g, yield 72%) was obtained. HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 749.1951 (theoretical value: 749.1959). Theoretical elemental content (%) C 51 H 31 N3S2: C, 81.68; H, 4.17; N, 5.60. Measured elemental content (%): C, 81.66; H, 4.18; N, 5.61.

[0311] Synthesis Example 45: Synthesis of Compound 761

[0312]

[0313] FF-16 was replaced with an equimolar amount of FF-761, and all other steps were the same as in Synthesis Example 4, yielding compound 761 (5.94 g, yield 73%). HPLC analysis showed a solid purity ≥ 99.92%. Mass spectrometry m / z: 813.2679 (theoretical value: 813.2668). Theoretical elemental content (%) C 61 H 35 NO2: C, 90.01; H, 4.33; N, 1.72. Measured elemental content (%): C, 90.03; H, 4.30; N, 1.74.

[0314] The following are compounds other than the aromatic compounds described in this invention used in the device fabrication examples:

[0315]

[0316]

[0317] A combined IVL testing system was constructed, consisting of testing software, a computer, a Keithley K2400 digital source meter, and a Photo Research PR788 spectral scanning luminance meter. The emission spectrum of the device prepared according to this invention was tested at atmospheric pressure and room temperature, as well as at a current density of 10 mA / cm². 2 The luminous efficiency was measured. The lifetime (brightness decay to 95% of initial brightness) of the device prepared in this invention was tested using the McScience M6000 OLED lifetime testing system at atmospheric pressure and room temperature. The test results are shown in Tables 1 to 4.

[0318] Comparative device fabrication example 1: Comparative device 1

[0319] First, the ITO / Ag / ITO glass substrate is ultrasonically cleaned twice with deionized water for 20 minutes each time. Then, it is ultrasonically cleaned sequentially with isopropanol, acetone and methanol for 20 minutes each. After that, it is exposed to ultraviolet light and ozone for 30 minutes. Finally, it is placed in a vacuum evaporation equipment for later use.

[0320] The following layers were deposited layer by layer on the aforementioned ITO / Ag / ITO glass substrate: a) 2-TNATA as a hole injection layer with a thickness of 30 nm; b) HT-4 as a hole transport layer with a thickness of 120 nm; c) HT-17 as a light-emitting auxiliary layer with a thickness of 30 nm; d) HOST-1, HOST-2 and Ir(dpm)(piq)2 (mass ratio 47:47:6) as a light-emitting layer with a thickness of 30 nm; e) TPBi as a hole blocking layer with a thickness of 20 nm; f) TMPyPB and Liq (mass ratio 1:1) as an electron transport layer with a thickness of 30 nm; f) LiF as an electron injection layer with a thickness of 1 nm; g) Mg and Ag (mass ratio 10:1) as a cathode with a thickness of 10 nm; h) ref-1 as a capping layer with a thickness of 120 nm.

[0321] Comparative device fabrication examples 2-7: Comparative devices 2-7

[0322] By replacing ref-1 in the overlay layer with ref-2, ref-3, ref-4, ref-5, ref-6, and ref-7 in sequence, and following the same steps as in Comparative Device Preparation Example 1, Comparative Devices 2 to 7 can be obtained.

[0323] Device fabrication examples 1-44: Light-emitting devices 1-44

[0324] Replace ref-1 in the capping layer sequentially with compounds 13, 14, 16, 20, 23, 24, 55, 58, 79, 82, 87, 108, 120, 127, 147, 170, 197, 199, 235, 256, 263, 299, 301, 307, 312, 338, 343, 368, 392, 411, 417, 419, 440, 457, 469, 480, 498, 501, 536, 559, 654, 751, 760, and 761. All other steps are the same as in Comparative Device Preparation Example 1, to obtain light-emitting devices 1 to 44.

[0325] Table 1

[0326]

[0327]

[0328]

[0329] Comparative device fabrication example 8: Comparative device 8

[0330] First, the ITO / Ag / ITO glass substrate is ultrasonically cleaned twice with deionized water for 20 minutes each time. Then, it is ultrasonically cleaned sequentially with isopropanol, acetone and methanol for 20 minutes each. After that, it is exposed to ultraviolet light and ozone for 30 minutes. Finally, it is placed in a vacuum evaporation equipment for later use.

[0331] The following layers were deposited layer by layer on the aforementioned ITO / Ag / ITO glass substrate: a) HATCN as a hole injection layer with a thickness of 10 nm; b) HT-13 as a hole transport layer with a thickness of 120 nm; c) HT-2 as a light-emitting auxiliary layer with a thickness of 30 nm; d) BH and BD (mass ratio 95:5) as a light-emitting layer with a thickness of 30 nm; d) TPBi as a hole blocking layer with a thickness of 20 nm; e) ref-1 and Liq (mass ratio 1:1) as an electron transport layer with a thickness of 30 nm; f) LiF as an electron injection layer with a thickness of 1 nm; g) Mg and Ag (mass ratio 10:1) as a cathode with a thickness of 10 nm; h) CP-4 as a capping layer with a thickness of 120 nm.

[0332] Comparative device fabrication examples 9-17: Comparative devices 9-17

[0333] By sequentially replacing ref-1 in the electron transport layer with ref-2, ref-3, ref-4, ref-5, ref-6, ref-7, ref-8, ref-9, and ref-10, and following the same steps as in Comparative Device Preparation Example 8, Comparative Devices 9 to 17 can be obtained.

[0334] Device fabrication examples 45-88: Light-emitting devices 45-88

[0335] By sequentially replacing ref-1 in the electron transport layer with compounds 13, 14, 16, 20, 23, 24, 55, 58, 79, 82, 87, 108, 120, 127, 147, 170, 197, 199, 235, 256, 263, 299, 301, 307, 312, 338, 343, 368, 392, 411, 417, 419, 440, 457, 469, 480, 498, 501, 536, 559, 654, 751, 760, and 761, and following the same steps as in Comparative Device Preparation Example 8, light-emitting devices 45–88 can be obtained.

[0336] Table 2

[0337]

[0338]

[0339]

[0340] Comparative device fabrication example 18: Comparative device 18

[0341] First, the ITO / Ag / ITO glass substrate is ultrasonically cleaned twice with deionized water for 20 minutes each time. Then, it is ultrasonically cleaned sequentially with isopropanol, acetone and methanol for 20 minutes each. After that, it is exposed to ultraviolet light and ozone for 30 minutes. Finally, it is placed in a vacuum evaporation equipment for later use.

[0342] The following layers were deposited layer by layer on the aforementioned ITO / Ag / ITO glass substrate: a) HT-11 and p-1 (mass ratio 100:1) as hole injection layer with a thickness of 10 nm; b) HT-11 as hole transport layer with a thickness of 120 nm; c) HT-8 as light-emitting auxiliary layer with a thickness of 30 nm; d) HOST-1, HOST-2 and Ir(dpm)(piq)2 (mass ratio 48:48:4) as light-emitting layer with a thickness of 30 nm; e) ref-1 as hole blocking layer with a thickness of 20 nm; f) TMPyPB and Liq (mass ratio 1:1) as electron transport layer with a thickness of 30 nm; g) LiF as electron injection layer with a thickness of 1 nm; h) Mg and Ag (mass ratio 10:1) as cathode with a thickness of 10 nm; i) CP-4 as capping layer with a thickness of 120 nm.

[0343] Comparative device fabrication examples 19-24: Comparative devices 19-24

[0344] By sequentially replacing ref-1 in the hole blocking layer with ref-2, ref-3, ref-4, ref-5, ref-6, and ref-7, and following the same steps as in Comparative Device Preparation Example 18, Comparative Devices 19 to 24 can be obtained.

[0345] Device fabrication examples 89-105: Light-emitting devices 89-105

[0346] By sequentially replacing ref-1 in the hole blocking layer with compounds 13, 16, 23, 147, 197, 199, 256, 301, 307, 343, 411, 419, 440, 457, 501, 536, and 760, and following the same steps as in Comparative Device Preparation Example 18, light-emitting devices 89–105 can be obtained.

[0347] Table 3

[0348] Device Examples Hole blocking layer material Drive voltage (V) Luminous efficacy (cd / A) Lifespan (h) Comparative Device Fabrication Example 18 ref-1 4.8 24.26 109.0 Comparative device fabrication example 19 ref-2 4.6 23.32 107.8 Comparative device fabrication example 20 ref-3 4.6 23.99 106.9 Comparative Device Fabrication Example 21 ref-4 4.8 23.87 110.2 Comparative device fabrication example 22 ref-5 4.7 24.40 111.5 Comparative device fabrication example 23 ref-6 4.7 24.62 112.6 Comparative device fabrication example 24 ref-7 4.9 23.65 105.8 Device fabrication example 89 Compound 13 4.3 30.28 143.7 Device fabrication example 90 Compound 16 4.4 30.56 142.4 Device fabrication example 91 Compound 23 4.2 30.87 140.3 Device fabrication example 92 Compound 147 4.2 30.95 144.6 Device fabrication example 93 Compound 197 4.1 31.35 144.1 Device fabrication example 94 Compound 199 4.0 31.26 142.0 Device fabrication example 95 Compound 256 4.2 31.46 145.0 Device fabrication example 96 Compound 301 4.2 30.04 139.8 Device fabrication example 97 Compound 307 4.3 30.80 142.9 Device fabrication example 98 Compound 343 4.2 30.15 139.3 Device fabrication example 99 Compound 411 4.1 31.15 141.6 Device fabrication example 100 Compound 419 4.2 30.22 143.2 Device fabrication example 101 Compound 440 4.2 30.09 141.2 Device fabrication example 102 Compound 457 4.1 30.35 138.5 Device fabrication example 103 Compound 501 4.0 30.73 145.7 Device fabrication example 104 Compound 536 4.1 30.44 138.9 Device fabrication example 105 Compound 760 4.0 30.66 140.8

[0349] Comparative device fabrication example 25: Comparative device 25

[0350] First, the ITO / Ag / ITO glass substrate is ultrasonically cleaned twice with deionized water for 20 minutes each time. Then, it is ultrasonically cleaned sequentially with isopropanol, acetone and methanol for 20 minutes each. After that, it is exposed to ultraviolet light and ozone for 30 minutes. Finally, it is placed in a vacuum evaporation equipment for later use.

[0351] The following layers were deposited layer by layer on the aforementioned ITO / Ag / ITO glass substrate: a) HT-7 and p-1 (mass ratio 100:1) as hole injection layer with a thickness of 20 nm; b) HT-7 as hole transport layer with a thickness of 120 nm; c) HT-10 as light-emitting auxiliary layer with a thickness of 30 nm; HOST-1, ref-11 and Ir(ppy)2(m-bppy) (mass ratio 47:47:6) as light-emitting layer with a thickness of 30 nm; d) TPBi as hole blocking layer with a thickness of 10 nm; e) BCP and Liq (mass ratio 1:1) as electron transport layer with a thickness of 30 nm; f) LiF as electron injection layer with a thickness of 1 nm; g) Mg and Ag (mass ratio 10:1) as cathode with a thickness of 10 nm; h) CP-4 as capping layer with a thickness of 120 nm.

[0352] Comparative device fabrication examples 26-31: Comparative devices 26-31

[0353] By sequentially replacing ref-11 in the light-emitting layer with ref-12, ref-13, ref-14, ref-15, ref-16, and ref-17, and following the same steps as in Comparative Device Preparation Example 25, Comparative Devices 26 to 31 can be obtained.

[0354] Device fabrication examples 106-149: Light-emitting devices 106-149

[0355] By sequentially replacing ref-11 in the luminescent layer with compounds 13, 14, 16, 20, 23, 24, 55, 58, 79, 82, 87, 108, 120, 127, 147, 170, 197, 199, 235, 256, 263, 299, 301, 307, 312, 338, 343, 368, 392, 411, 417, 419, 440, 457, 469, 480, 498, 501, 536, 559, 654, 751, 760, and 761, and following the same steps as in Comparative Device Preparation Example 25, luminescent devices 106–149 can be obtained.

[0356] Table 4

[0357]

[0358]

[0359]

[0360] The device data in Tables 1 to 4 show that the aromatic compounds provided by this invention, as capping materials, can effectively improve the luminous efficiency and lifespan of OLED devices. The aromatic compounds provided by this invention can also be used as electron transport materials, hole blocking materials, or host materials, and can also improve the driving voltage, luminous efficiency, and lifespan of devices.

[0361] It should be noted that the present invention has been specifically described with reference to individual embodiments, but those skilled in the art can make various forms or details of improvements to the present invention without departing from the principles of the present invention, and these improvements also fall within the protection scope of the present invention.

Claims

1. An aromatic compound, characterized in that, The aromatic compound has the structure shown in formula (I): Wherein, ring A is selected from one of the following groups: The Ar1 is selected from one of the following groups: The Ar2 group is selected from one of the following groups: The ring B is selected from one of substituted or unsubstituted C6-C30 aromatic rings and substituted or unsubstituted C3-C30 heteroaromatic rings; Each time u appears, it is selected from CR1 or N, either the same or different; each time v appears, it is selected from CR1' or N, either the same or different. X is selected from O, S, or NR2; Y is selected from CR1 or N; Z is selected from O, S, CR3R4, or NR2; W is selected from O or S; Each time R1 appears, it is selected from the same or different groups of the following: no hydrogen atom, deuterium atom, tritium atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 alkyl group, substituted or unsubstituted C3-C12 cycloalkyl group, substituted or unsubstituted silyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C3-C30 heteroaryl group, a monovalent group formed by fusion of a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, a monovalent group formed by fusion of a substituted or unsubstituted C3-C30 heteroaryl ring and a substituted or unsubstituted C3-C7 aliphatic ring, or a combination thereof. Each time R2 appears, it is selected, either identically or differently, from one of the following: substituted or unsubstituted C1-C12 alkyl groups, substituted or unsubstituted C3-C12 cycloalkyl groups, substituted or unsubstituted silyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C3-C30 heteroaryl groups, a monovalent group formed by fusion of a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, a monovalent group formed by fusion of a substituted or unsubstituted C3-C30 heteroaryl ring and a substituted or unsubstituted C3-C7 aliphatic ring, or a combination thereof. The R3 and R4 are independently selected from one of the following: substituted or unsubstituted C1-C12 alkyl groups, substituted or unsubstituted C3-C12 cycloalkyl groups, substituted or unsubstituted silyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C3-C30 heteroaryl groups, a monovalent group formed by fusion of a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, a monovalent group formed by fusion of a substituted or unsubstituted C3-C30 heteroaryl ring and a substituted or unsubstituted C3-C7 aliphatic ring, or combinations thereof; or R3 and R4 are linked together to form a ring. The L1 is selected from one of the following: a single bond, a substituted or unsubstituted C6-C30 arylene group, a divalent group formed by the fusion of a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring; and combinations thereof. The L2 is selected from one of the following: a single bond, a substituted or unsubstituted C6-C30 arylene, a substituted or unsubstituted C3-C30 heteroarylene, a divalent group formed by the fusion of a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, a divalent group formed by the fusion of a substituted or unsubstituted C3-C30 heteroaromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, or a combination thereof; The L3 is selected from one of the following: a substituted or unsubstituted C6-C30 aryl group, a divalent group formed by the fusion of a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring; The 'a' is selected from 0, 1, 2, or 3; Each time R appears, it is selected from the same or different groups of hydrogen atom, deuterium atom, tritium atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 alkyl group, substituted or unsubstituted C3-C12 cycloalkyl group, substituted or unsubstituted silyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C3-C30 heteroaryl group, a monovalent group formed by fusion of a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, a monovalent group formed by fusion of a substituted or unsubstituted C3-C30 heteroaryl ring and a substituted or unsubstituted C3-C7 aliphatic ring, or a combination thereof.

2. The aromatic compound according to claim 1, characterized in that, The Ar1 is selected from one of the following groups: Wherein, each occurrence of a2 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; each occurrence of b2 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; each occurrence of c2 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; each occurrence of d2 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12; each occurrence of e2 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11; each occurrence of f2 is selected from 0, 1, 2, 3, or 4; each occurrence of g2 is selected from 0, 1, or 2; and each occurrence of h2 is selected from 0, 1, 2, 3, or 4. 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, or 14; each time i2 appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, or 13, either the same or different; each time j2 appears, it is selected from 0, 1, 2, 3, 4, 5, or 6, either the same or different; each time k2 appears, it is selected from 0, 1, 2, 3, 4, or 5, either the same or different; Each time l2 appears, it is selected from 0, 1, 2, or 3, either the same or different; each time m2 appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, or 15, either the same or different; each time n2 appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, or 17, either the same or different. R1 is as described in claim 1.

3. The aromatic compound according to claim 1, characterized in that, The Ar2 group is selected from one of the following groups: Wherein, each occurrence of a1 is selected from 0, 1, 2, 3, or 4; each occurrence of b1 is selected from 0, 1, 2, 3, 4, 5, or 6; each occurrence of c1 is selected from 0, 1, or 2; each occurrence of d1 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; each occurrence of e1 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; each occurrence of f1 is selected from 0, 1, 2, or 3; each occurrence of g1 is selected from 0, 1, 2, 3, 4, or 5; and each occurrence of h1 is selected from 0 or 1. Both X and R1 are as described in claim 1.

4. The aromatic compound according to claim 1, characterized in that, The aforementioned Selected from one of the following groups: Both X and R1 are as described in claim 1; a1, b1, c1, d1, e1, f1, and g1 are all as described in claim 3.

5. The aromatic compound according to claim 1, characterized in that, The L1 is selected from a single bond, one of the following groups: The L2 is selected from one of the single-bonded groups shown below: The L3 is selected from one of the following groups: Wherein, the a 101 Each time it appears, it is selected from 0, 1, 2, 3, or 4, either identically or differently; the b mentioned 101 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, or 6, either identically or differently; the c mentioned 101 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8, either identically or differently; the d mentioned 101 Each time it appears, it is selected from 0, 1, or 2, either identically or differently; the e 101 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10, either identically or differently; the f mentioned 101 Each time it appears, it is selected from 0, 1, 2, or 3, either identically or differently; the g mentioned 101 Each time it appears, it is selected from 0, 1, 2, 3, 4 or 5, either the same or different. The R mentioned 101 Each time it appears, it is selected from the same or different groups of hydrogen atom, deuterium atom, tritium atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 alkyl group, substituted or unsubstituted C3-C12 cycloalkyl group, substituted or unsubstituted silyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C3-C30 heteroaryl group, a monovalent group formed by fusion of a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, a monovalent group formed by fusion of a substituted or unsubstituted C3-C30 heteroaryl ring and a substituted or unsubstituted C3-C7 aliphatic ring, or a combination thereof; The R mentioned 102 Each time it appears, it is selected from one of the following, either the same or different: hydrogen atom, deuterium atom, tritium atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 alkyl group, substituted or unsubstituted C3-C12 cycloalkyl group, or substituted or unsubstituted silyl group.

6. The aromatic compound according to claim 1, characterized in that, The aromatic compound is selected from one of the following compounds:

7. An organic electroluminescent device, comprising a cathode, an anode, and an organic layer, wherein the organic layer is located between the cathode and the anode, characterized in that, The organic layer contains an aromatic compound as described in any one of claims 1 to 6.

8. The organic electroluminescent device according to claim 7, wherein the organic layer comprises a hole transport region, a light-emitting layer, and an electron transport region, characterized in that, The electron transport region contains an aromatic compound as described in any one of claims 1 to 6.

9. The organic electroluminescent device according to claim 7, wherein the organic layer comprises a hole transport region, a light-emitting layer, and an electron transport region, and the light-emitting layer comprises a host material and a dopant material, characterized in that, The main material contains an aromatic compound as described in any one of claims 1 to 6.

10. An organic electroluminescent device, comprising a cathode, an anode, an organic layer, and a capping layer, characterized in that, The coating layer contains an aromatic compound as described in any one of claims 1 to 6.

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