Anthracene compound and organic electroluminescent device thereof

Abstract

The invention provides an anthracene compound and an organic electroluminescent device thereof. The anthracene compound can serve as a nucleation inhibition layer material, a film structure is formed through a vapor deposition process, the surface of the anthracene compound shows relatively low affinity to deposition of a conductive material, deposition of the conductive material on the surface of the anthracene compound can be inhibited, and therefore when the conductive material is deposited on the outer side of an electrode on the light-transmitting side to form an auxiliary electrode, the auxiliary electrode can be formed. The selective deposition of the conductive material can be realized, the cathode is patterned, the IR voltage drop of the device is reduced, and the high transmittance of light is ensured. The anthracene compound can also be used as a main body material to be applied to OLED devices, and better electrical properties such as low driving voltage, high luminous efficiency and long service life can also be obtained.

Description

Technical Field

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

[0002] Organic light-emitting diodes (OLEDs) have the characteristics of being thin and light, having a wide viewing angle, fast response speed, wide operating temperature range, low energy consumption, high efficiency, good color purity, high definition, and good flexibility. They have been widely used in the fields of lighting and display and are considered by the industry to be one of the most promising display and lighting technologies.

[0003] OLED devices have two electrodes: a cathode and an anode, sandwiched between them a light-emitting layer containing a luminescent material (guest material). When the device is powered on, holes and electrons are injected from the anode and cathode, respectively, and reach the light-emitting layer. There, they recombine to generate excitons, releasing energy. Under the influence of an electric field, these excitons migrate, transferring energy to the luminescent material. Electrons in the luminescent material molecules transition from the ground state to an excited state. Since the excited state is unstable, the electrons return to the ground state, releasing energy as light, thus producing the luminescence phenomenon. Based on the different light propagation paths, OLEDs can be divided into bottom-emitting and top-emitting devices. In bottom-emitting devices, light propagates from the anode through the substrate to the outside of the device, while in top-emitting devices, light propagates through the cathode. Top-emitting devices emit light from the cathode side, bypassing the substrate, resulting in a more detailed and clearer image with higher color vibrancy. The cathode of a top-emitting OLED display is formed using a transparent or semi-transparent conductive material with a low thickness to allow more light transmission. However, the reduction in electrode thickness is accompanied by an increase in its sheet resistance, resulting in a higher current-resistance (IR) drop, which is detrimental to the performance and efficiency of OLEDs.

[0004] Cathode patterning technology can reduce the IR voltage drop loss in the OLED cathode layer, overcoming the aforementioned technical challenges. Cathode patterning involves nucleation inhibition materials and conductive materials, typically achieved using a physical vapor deposition (PVD) process with a photomask. This effectively suppresses the deposition of conductive materials on the nucleation inhibition materials, resulting in higher transmittance. However, currently, there are few types of nucleation inhibition materials, and their application effects are unsatisfactory. Therefore, the development of novel and effective nucleation inhibition materials is urgently needed. Summary of the Invention

[0005] To address the aforementioned technical problems, this invention provides an anthracene compound:

[0006]

[0007] Wherein, Ar1 is selected from C2-C30 nitrogen-containing heteroaryl groups substituted with one or more R1s, and the heteroatoms in the nitrogen-containing heteroaryl group are selected only from -N=. Each time R1 appears, it is selected from one of the following groups: hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 alkyl group, substituted or unsubstituted C3-C12 cycloalkyl group, substituted or unsubstituted C6-C30 aryl group, monovalent group formed by fusion of substituted or unsubstituted C3-C20 aliphatic ring and C6-C30 aromatic ring, and substituted or unsubstituted C2-C30 heteroaryl group.

[0008] The Ar2 is selected from one of the following groups substituted with one or more R2: aryl (C6-C30), monovalent group formed by fusion of aliphatic ring (C3-C20) and aromatic ring (C6-C30), and heteroaryl (C2-C30); each time the R2 appears, it is selected from one of the following groups, either the same or different: hydrogen atom, deuterium atom, halogen atom, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, monovalent group formed by fusion of aliphatic ring (C3-C20) and aromatic ring (C6-C30), and heteroaryl (substituted or unsubstituted C2-C30).

[0009] The Ar3 is selected from one of the following groups substituted with one or more R3s: aryl of C6 to C30, a monovalent group formed by the fusion of an aliphatic ring of C3 to C20 and an aromatic ring of C6 to C30, and a heteroaryl of C2 to C30; each time the R3 appears, it is selected from one of the following groups, either the same or different: hydrogen atom, deuterium atom, halogen atom, cyano, substituted or unsubstituted alkyl of C1 to C12, substituted or unsubstituted cycloalkyl of C3 to C12, substituted or unsubstituted silyl, substituted or unsubstituted aryl of C6 to C30, a monovalent group formed by the fusion of an aliphatic ring of C3 to C20 and an aromatic ring of C6 to C30, and a heteroaryl of C2 to C30, and at least one R3 is selected from a substituted or unsubstituted silyl.

[0010] The 'a' is selected from 0, 1, 2, 3, 4, 5, 6, or 7;

[0011] Each time R appears, it is selected from one of the following, either the same or different: hydrogen atom, deuterium 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, a monovalent group formed by fusion of a substituted or unsubstituted C3-C20 aliphatic ring and a C6-C30 aromatic ring, or substituted or unsubstituted C2-C30 heteroaryl group.

[0012] The L1, L2, and L3 are independently selected from single bonds, substituted or unsubstituted C6-C25 arylene groups, divalent groups formed by the fusion of substituted or unsubstituted C3-C10 aliphatic rings and C6-C25 aromatic rings, substituted or unsubstituted C2-C20 heteroarylene groups, or combinations thereof.

[0013] The present invention also provides an organic electroluminescent device, comprising a first electrode, an organic layer, a second electrode, and a nucleation inhibition layer, wherein the organic layer is located on the first electrode, the second electrode is located on the organic layer, and the nucleation inhibition layer is located on the side of the second electrode away from the first electrode or between the organic layer and the second electrode, and the nucleation inhibition layer contains the anthracene compound described in the present invention.

[0014] The present invention also provides an organic electroluminescent device, comprising a first electrode, a second electrode, and an organic layer, wherein the organic layer is located between the first electrode and the second electrode, and the organic layer includes a hole transport region, a light-emitting layer, and an electron transport region, wherein the light-emitting layer is located between the first electrode and the second electrode, the hole transport region is located between the first electrode and the light-emitting layer, and the electron transport region is located between the light-emitting layer and the second electrode, and the light-emitting layer contains the anthracene compound described in the present invention.

[0015] Beneficial effects:

[0016] The anthracene compounds provided in this invention, used as nucleation inhibition layer materials, form a film structure through vapor deposition. Their surfaces exhibit relatively low affinity for conductive materials, suppressing their deposition. This allows for selective deposition of conductive materials when depositing auxiliary electrodes on the outer side of the light-transmitting electrode, enabling cathode patterning, reducing IR voltage drop, and ensuring high light transmittance. When used as host materials in OLED devices, the anthracene compounds also achieve better electrical performance, such as lower driving voltage, higher luminous efficiency, and longer lifespan. Attached Figure Description

[0017] Figure 1 This is a schematic diagram of a top-emitting device including a nucleation suppression layer provided by the present invention. Detailed Implementation

[0018] The technical solutions of this invention will be clearly and completely described below with reference to specific embodiments. Obviously, the described embodiments are only some embodiments of this invention, and not all embodiments. 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.

[0019] 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.

[0020] 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".

[0021] The halogen atom mentioned in this invention refers to fluorine, chlorine, bromine, and iodine atoms.

[0022] 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 R k The same or different groups are selected 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 group of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic rings, and fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaryl rings. Preferably, each R k The same or different groups are selected 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... kThe 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 silanes specifically include trimethylsilane, triethylsilane, triisopropylsilane, tri-tert-butylsilane, tert-butyldimethylsilane, vinyldimethylsilane, isopropyldimethylsilane, triphenylsilane, diphenylmethylsilane, phenyldimethylsilane, diphenylpyridylsilane, phenyldipyridylsilane, tripyridylsilane, etc., but are not limited thereto. The aforementioned substituted silanes are preferably trimethylsilane, triethylsilane, triisopropylsilane, tri-tert-butylsilane, tert-butyldimethylsilane, isopropyldimethylsilane, triphenylsilane, diphenylmethylsilane, and phenyldimethylsilane.

[0023] 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 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 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.

[0024] 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.

[0025] 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.

[0026] 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.

[0027] 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.

[0028] 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, pyrroloyl, imidazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, 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, phenoxthialyl, quinolinyl, isoquinolinyl, quinoxolinyl, quinazolinyl, etc., but are not limited thereto. The aforementioned heteroaryl groups are preferably benzothiophene, benzofuran, indolyl, benzoxazolyl, benzoimidazolyl, benzothiazolyl, dibenzofuran, dibenzothiophene, carbazolyl, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinoxalinyl, and quinazolinyl.

[0029] The monovalent group formed by the fusion of an aliphatic ring and an aromatic 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, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, naphthocyclopropane, naphthocyclobutane, naphthocyclopentane, and naphthocyclohexane.

[0030] 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 arylene is a divalent group.

[0031] 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.

[0032] The divalent group formed by the fusion of an aliphatic ring and an aromatic ring as described in this invention refers to a group formed by the fusion of an aliphatic ring and an aromatic 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 aliphatic ring and an aromatic ring, the difference being that the divalent group formed by the fusion of an aliphatic ring and an aromatic ring is a divalent group.

[0033] In this invention, "-N=" refers to N connected by a single bond and a double bond.

[0034] 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.

[0035] In this invention, "substituted or unsubstituted" means unsubstituted or substituted by one or more substituents selected from the group consisting of: deuterium, 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, C3-C12 cycloalkenyl. C3-C12 heterocyclic alkyl groups, C6-C30 aryl groups, C2-C30 heteroaryl groups, substituted or unsubstituted silyl groups, wherein the substituted groups are the same or different from each other when substituted by multiple substituents; preferably, this means unsubstituted or substituted by one or more substituents selected from the group consisting of: deuterium atom, fluorine atom, cyano, methyl, trifluoromethyl, deuterated methyl, ethyl, deuterated ethyl, n-propyl, isopropyl, deuterated isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, deuterated tert-butyl, cyclopropane, methyl-substituted cyclopropane, ethyl-substituted cyclopropane, deuterated cyclopropane, cyclobutane, methyl-substituted cyclobutane, ethyl-substituted cyclobutane, deuterated cyclobutane, cyclopentane, methyl-substituted cyclopropane Pentyl, ethyl-substituted cyclopentyl, deuterated cyclopentyl, cyclohexyl, methyl-substituted cyclohexyl, ethyl-substituted cyclohexyl, n-propyl-substituted cyclohexyl, n-butyl-substituted cyclohexyl, cyclohexane-substituted cyclohexyl, deuterated cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, adamantyl, methyl-substituted adamantyl, ethyl-substituted adamantyl, deuterated adamantyl, norbornyl, methyl-substituted norbornyl, ethyl-substituted norbornyl, deuterated norbornyl, tetrahydropyrrolyl, piperidinyl, morpholinyl, thiomorpholinyl, methyl-substituted piperazine, ethyl-substituted piperazine, phenyl-substituted piperazine, naphthyl-substituted piperazine, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, anthraceneyl. Deuterated anthracene, phenanthrene, deuterated phenanthrene, 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, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalyl, 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.

[0036] 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.

[0037] 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.

[0038] 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:

[0039]

[0040] 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.

[0041] In this specification, "at least one" includes one, two, three, four, five, six, seven, eight or more.

[0042] 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.

[0043] 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.

[0044] This invention provides an anthracene compound:

[0045]

[0046] Wherein, Ar1 is selected from C2-C30 nitrogen-containing heteroaryl groups substituted with one or more R1s, and the heteroatoms in the nitrogen-containing heteroaryl group are selected only from -N=. Each time R1 appears, it is selected from one of the following groups: hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 alkyl group, substituted or unsubstituted C3-C12 cycloalkyl group, substituted or unsubstituted C6-C30 aryl group, monovalent group formed by fusion of substituted or unsubstituted C3-C20 aliphatic ring and C6-C30 aromatic ring, and substituted or unsubstituted C2-C30 heteroaryl group.

[0047] The Ar2 is selected from one of the following groups substituted with one or more R2: aryl (C6-C30), monovalent group formed by fusion of aliphatic ring (C3-C20) and aromatic ring (C6-C30), and heteroaryl (C2-C30); each time the R2 appears, it is selected from one of the following groups, either the same or different: hydrogen atom, deuterium atom, halogen atom, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, monovalent group formed by fusion of aliphatic ring (C3-C20) and aromatic ring (C6-C30), and heteroaryl (substituted or unsubstituted C2-C30).

[0048] The Ar3 is selected from one of the following groups substituted with one or more R3s: aryl of C6 to C30, a monovalent group formed by the fusion of an aliphatic ring of C3 to C20 and an aromatic ring of C6 to C30, and a heteroaryl of C2 to C30; each time the R3 appears, it is selected from one of the following groups, either the same or different: hydrogen atom, deuterium atom, halogen atom, cyano, substituted or unsubstituted alkyl of C1 to C12, substituted or unsubstituted cycloalkyl of C3 to C12, substituted or unsubstituted silyl, substituted or unsubstituted aryl of C6 to C30, a monovalent group formed by the fusion of an aliphatic ring of C3 to C20 and an aromatic ring of C6 to C30, and a heteroaryl of C2 to C30, and at least one R3 is selected from a substituted or unsubstituted silyl.

[0049] The 'a' is selected from 0, 1, 2, 3, 4, 5, 6, or 7;

[0050] Each time R appears, it is selected from one of the following, either the same or different: hydrogen atom, deuterium 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, a monovalent group formed by fusion of a substituted or unsubstituted C3-C20 aliphatic ring and a C6-C30 aromatic ring, or substituted or unsubstituted C2-C30 heteroaryl group.

[0051] The L1, L2, and L3 are independently selected from single bonds, substituted or unsubstituted C6-C25 arylene groups, divalent groups formed by the fusion of substituted or unsubstituted C3-C10 aliphatic rings and C6-C25 aromatic rings, substituted or unsubstituted C2-C20 heteroarylene groups, or combinations thereof.

[0052] Preferably, the anthracene compound is selected from the structure shown in formula (I-1) or (I-2):

[0053]

[0054] Each time R' appears, it is selected from one of the following, either the same or different: hydrogen atom, deuterium 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;

[0055] The R” is selected from one of the following: substituted or unsubstituted C6-C30 aryl groups, a monovalent group formed by fusion of a substituted or unsubstituted C3-C20 aliphatic ring and a C6-C30 aromatic ring, or a substituted or unsubstituted C2-C30 heteroaryl group.

[0056] The value of a' is selected from 0, 1, 2, 3, 4, 5 or 6.

[0057] Preferably, the substituents in the "substituted or unsubstituted" group are independently selected from one or more of the following: deuterium 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 C2-C30 heteroaryl group, and monovalent group formed by fusion of a substituted or unsubstituted C3-C20 aliphatic ring and a C6-C30 aromatic ring. When there are multiple substituents, the multiple substituents may be the same or different.

[0058] Preferably, the substituents in "substituted or unsubstituted" are independently selected from deuterium atom; fluorine atom; cyano; methyl group substituted or unsubstituted by deuterium or fluorine atom; ethyl group; n-propyl group; isopropyl group substituted or unsubstituted by deuterium or fluorine atom; n-butyl group; sec-butyl group; isobutyl group; tert-butyl group substituted or unsubstituted by deuterium or fluorine atom; and groups substituted or unsubstituted by one or more of deuterium atom, methyl, ethyl, isopropyl, and tert-butyl as shown below: cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, and norbornane; and groups substituted or unsubstituted by one or more of deuterium atom, fluorine atom, cyano, methyl, ethyl, isopropyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, and norbornane as shown below: phenyl group. The following are substituted or unsubstituted silyl groups: naphthyl, anthraceneyl, phenanthreneyl, triphenylene, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirodifluorenyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, N-phenylcarbazoyl, benzocyclopentyl, benzocyclohexyl; substituted or unsubstituted by one or more of the following: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, phenyl, deuterated phenyl, methyl-substituted phenyl, tert-butyl-substituted phenyl, fluorine-substituted phenyl, cyano-substituted phenyl, adamantyl-substituted phenyl, norbornel-substituted phenyl, naphthyl, deuterated naphthyl, anthraceneyl, phenanthreneyl, biphenyl, pyridyl, pyrimidinyl, dibenzofuranyl, dibenzothiopheneyl, and 9,9-dimethylfluorenyl. When there are multiple substituents, the multiple substituents may be the same or different.

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

[0060]

[0061] Wherein, each occurrence of a1 is selected from 0, 1, 2, 3, or 4; each occurrence of b1 is selected from 0, 1, 2, or 3; each occurrence of c1 is selected from 0, 1, or 2; each occurrence of d1 is selected from 0, 1, 2, 3, 4, 5, or 6; each occurrence of e1 is selected from 0, 1, 2, 3, 4, or 5; each occurrence of f1 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; and each occurrence of g1 is selected from 0, 1, 2, 3, 4, 5, 6, or 7.

[0062] Each time R1 appears, it is selected from one of the following groups, either the same or different: hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 alkyl group, substituted or unsubstituted C3-C12 cycloalkyl group, substituted or unsubstituted C6-C30 aryl group, a monovalent group formed by fusion of a substituted or unsubstituted C3-C20 aliphatic ring and a C6-C30 aromatic ring, or substituted or unsubstituted C2-C30 heteroaryl group.

[0063] Preferably, each time R1 appears, it is selected from hydrogen atoms; deuterium atoms; fluorine atoms; cyano groups; and groups substituted or unsubstituted by one or more of deuterium and fluorine atoms, including: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornane; and groups substituted by deuterium, fluorine, cyano, methyl, deuterated methyl, trifluoromethyl, ethyl, isopropyl, tert-butyl, cyclopropane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornane. One or more of the following groups, substituted or unsubstituted, are included in the group: phenyl, naphthyl, anthracene, phenanthrene, triphenylene, biphenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirodifluorenyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, pyridinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiopheneyl, indolyl, dibenzofuranyl, dibenzothiopheneyl, N-phenylcarbazoyl, benzoxazolyl, benzothiazoyl, and benzimidazolyl.

[0064] Preferably, the Ar2 is selected from one of the following groups:

[0065]

[0066] Wherein, each occurrence of a2 is selected from 0, 1, 2, 3, 4, or 5; each occurrence of b2 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; each occurrence of c2 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; each occurrence of d2 is selected from 0, 1, 2, 3, or 4; each occurrence of e2 is selected from 0, 1, 2, or 3; and each occurrence of f2 is selected from 0, 1, 2, or 3. The values ​​of g2 and h2 are selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8, respectively. g2 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11, respectively. h2 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, or 13, respectively. i2 is selected from 0, 1, 2, 3, 4, 5, or 6, respectively. j2 is selected from 0, 1, or 2, respectively.

[0067] Each time R2 appears, it is selected from one of the following groups, either the same or different: hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 alkyl group, substituted or unsubstituted C3-C12 cycloalkyl group, substituted or unsubstituted C6-C30 aryl group, a monovalent group formed by fusion of a substituted or unsubstituted C3-C20 aliphatic ring and a C6-C30 aromatic ring, or substituted or unsubstituted C2-C30 heteroaryl group.

[0068] Z1 is selected from oxygen atoms, sulfur atoms, and CR. a R b or NR c ;

[0069] The Z2 is selected from oxygen atoms, sulfur atoms, or NR. d ;

[0070] The R mentioned a R b R c R d It is independently selected from one of the following: substituted or unsubstituted C1-C12 alkyl groups, substituted or unsubstituted C3-C12 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, a monovalent group formed by fusion of a substituted or unsubstituted C3-C20 aliphatic ring and a C6-C30 aromatic ring, or substituted or unsubstituted C2-C30 heteroaryl groups.

[0071] Preferably, each time R2 appears, it is selected from hydrogen atoms; deuterium atoms; fluorine atoms; cyano groups; and groups substituted or unsubstituted by one or more of deuterium and fluorine atoms, including: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornane; and groups substituted by deuterium, fluorine, cyano, methyl, deuterated methyl, trifluoromethyl, ethyl, isopropyl, tert-butyl, cyclopropane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornane. One or more of the following groups, substituted or unsubstituted, are included in the group: phenyl, naphthyl, anthracene, phenanthrene, triphenylene, biphenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirodifluorenyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, pyridinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiopheneyl, indolyl, dibenzofuranyl, dibenzothiopheneyl, N-phenylcarbazoyl, benzoxazolyl, benzothiazoyl, and benzimidazolyl.

[0072] Preferably, the R a R b R c R d The following groups, independently selected from those substituted or unsubstituted by one or more of deuterium and fluorine atoms: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornane; and the following groups, substituted or unsubstituted by one or more of deuterium, fluorine, cyano, methyl, deuterated methyl, trifluoromethyl, ethyl, isopropyl, tert-butyl, cyclopropane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornane. Group: One of phenyl, naphthyl, anthracene, phenanthrene, triphenylene, biphenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirodifluorenyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, pyridinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiopheneyl, indolyl, dibenzofuranyl, dibenzothiopheneyl, N-phenylcarbazoyl, benzoxazolyl, benzothiazoyl, and benzimidazolyl.

[0073] Preferably, the Ar3 is selected from one of the following groups:

[0074]

[0075]

[0076] Wherein, each occurrence of a3 is selected from 0, 1, 2, 3, or 4; each occurrence of b3 is selected from 0, 1, 2, 3, 4, 5, or 6; each occurrence of c3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; each occurrence of d3 is selected from 0, 1, 2, or 3; each occurrence of e3 is selected from 0, 1, or 2; each occurrence of f3 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; each occurrence of g3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; each occurrence of h3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12; and each occurrence of i3 is selected from 0, 1, 2, 3, 4, or 5.

[0077] Each time R3 appears, it is selected from one of the following groups, either the same or different: hydrogen atom, deuterium 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, a monovalent group formed by fusion of a substituted or unsubstituted C3-C20 aliphatic ring and a C6-C30 aromatic ring, or substituted or unsubstituted C2-C30 heteroaryl group.

[0078] The Z3 is selected from oxygen atoms, sulfur atoms, and CR. f R g or NR h ;

[0079] The Z4 is selected from oxygen atoms, sulfur atoms, or NR. i ;

[0080] The R mentioned f R g R h R i It is independently selected from one of the following: substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, a monovalent group formed by fusion of a substituted or unsubstituted C3-C20 aliphatic ring and a C6-C30 aromatic ring, or substituted or unsubstituted C2-C30 heteroaryl.

[0081] The R mentioned eEach time it appears, it is selected from the same or different groups of hydrogen atom, deuterium atom, 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, a monovalent group formed by fusion of a substituted or unsubstituted C3-C20 aliphatic ring and a C6-C30 aromatic ring, or substituted or unsubstituted C2-C30 heteroaryl group.

[0082] Preferably, each time R3 appears, it is selected from hydrogen atoms; deuterium atoms; fluorine atoms; cyano groups; and groups substituted or unsubstituted by one or more of deuterium and fluorine atoms, including: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornyl; and groups substituted by deuterium atoms, fluorine atoms, cyano, methyl, deuterated methyl, trifluoromethyl, ethyl, isopropyl, tert-butyl, cyclopropane, cyclobutane, cyclohexane, cycloheptane, cyclopropane, cyclobut ... Propanyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, anthracene, deuterated anthracene, phenanthrene, deuterated phenanthrene, phenylenetriethylene, deuterated phenylenetriethylene, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirodifluorenyl, benzocyclopropane, benzocyclobutane, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, pyridyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl Silyl groups substituted or unsubstituted with one or more of the following: benzofuranyl, benzothiophenyl, indolyl, dibenzofuranyl, dibenzothiophenyl, N-phenylcarbazoyl, benzoxazolyl, benzothiazoyl, and benzimidazolyl; phenyl, naphthyl, and anthraceneyl groups substituted or unsubstituted with one or more of the following groups: deuterium, fluorine, cyano, methyl, deuterated methyl, trifluoromethyl, ethyl, isopropyl, tert-butyl, cyclopropane, cyclopentane, cyclohexane, cycloheptane, adamantyl, and norbornel. One of the following: phenanthrene, triphenylene, biphenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirodifluorenyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, pyridinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiopheneyl, indolyl, dibenzofuranyl, dibenzothiopheneyl, N-phenylcarbazoyl, benzoxazolyl, benzothiazoyl, and benzimidazolyl.

[0083] Preferably, the R f R g R h R iThe following groups, independently selected from those substituted or unsubstituted by one or more of deuterium and fluorine atoms: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornane; and the following groups, substituted or unsubstituted by one or more of deuterium, fluorine, cyano, methyl, deuterated methyl, trifluoromethyl, ethyl, isopropyl, tert-butyl, cyclopropane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornane. Group: One of phenyl, naphthyl, anthracene, phenanthrene, triphenylene, biphenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirodifluorenyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, pyridinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiopheneyl, indolyl, dibenzofuranyl, dibenzothiopheneyl, N-phenylcarbazoyl, benzoxazolyl, benzothiazoyl, and benzimidazolyl.

[0084] Preferably, the R eEach time it appears, it is selected from the same or different groups: hydrogen atom; deuterium atom; and the following groups substituted or unsubstituted by one or more of deuterium and fluorine atoms: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornane; and groups substituted by deuterium, fluorine, cyano, methyl, deuterated methyl, trifluoromethyl, ethyl, isopropyl, tert-butyl, cyclopropane, cyclopentane, cyclohexane. alkyl, cycloheptyl, adamantyl, norbornelyl, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, anthracene, deuterated anthracene, phenanthrene, deuterated phenanthrene, triphenylene, deuterated triphenylene, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirodifluorenyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, pyridinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, Silyl groups substituted or unsubstituted with one or more of the following: benzothiophene, indolyl, dibenzofuranyl, dibenzothiophene, N-phenylcarbazole, benzoxazolyl, benzothiazolyl, and benzimidazolyl; phenyl, naphthyl, methyl, deuterated methyl, trifluoromethyl, ethyl, isopropyl, tert-butyl, cyclopropane, cyclopentane, cyclohexane, cycloheptane, adamantyl, and norbornel alkyl. One of the following: triphenylene, biphenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirodifluorenyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, pyridinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiopheneyl, indolyl, dibenzofuranyl, dibenzothiopheneyl, N-phenylcarbazoyl, benzoxazolyl, benzothiazoyl, and benzimidazolyl.

[0085] Preferred, R e At least one of them is not selected from hydrogen and deuterium atoms.

[0086] Preferably, the aforementioned Choose one of the following structures:

[0087]

[0088] Preferably, L1 and L2 are independently selected from single bonds, groups as shown below, or combinations thereof:

[0089]

[0090]

[0091] Wherein, each occurrence of a4 is selected from 0, 1, 2, 3, or 4; each occurrence of b4 is selected from 0, 1, 2, or 3; each occurrence of c4 is selected from 0, 1, or 2; each occurrence of d4 is selected from 0, 1, 2, 3, 4, 5, or 6; each occurrence of e4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; each occurrence of f4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; each occurrence of g4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12; and each occurrence of h4 is selected from 0 or 1.

[0092] Each time R4 appears, it is selected from one of the following groups, either the same or different: hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 alkyl group, substituted or unsubstituted C3-C12 cycloalkyl group, substituted or unsubstituted C6-C30 aryl group, a monovalent group formed by fusion of a substituted or unsubstituted C3-C20 aliphatic ring and a C6-C30 aromatic ring, or substituted or unsubstituted C2-C30 heteroaryl group.

[0093] The E1 is selected from oxygen atoms, sulfur atoms, and CR. j R k or NR m ;

[0094] The E2 is selected from oxygen atoms, sulfur atoms, or NR. n ;

[0095] The R mentioned j R k R m R n It is independently selected from one of the following: substituted or unsubstituted C1-C12 alkyl groups, substituted or unsubstituted C3-C12 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, a monovalent group formed by fusion of a substituted or unsubstituted C3-C20 aliphatic ring and a C6-C30 aromatic ring, or substituted or unsubstituted C2-C30 heteroaryl groups.

[0096] Preferably, each time R4 appears, it is selected from the following groups, either identically or differently: hydrogen atom; deuterium atom; fluorine atom; cyano group; and groups substituted or unsubstituted by one or more of deuterium and fluorine atoms: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornane; and groups substituted by deuterium, fluorine, cyano, methyl, deuterated methyl, trifluoromethyl, ethyl, isopropyl, tert-butyl, cyclopropane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornane. One or more of the following groups, substituted or unsubstituted, are included in the group: phenyl, naphthyl, anthracene, phenanthrene, triphenylene, biphenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirodifluorenyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, pyridinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiopheneyl, indolyl, dibenzofuranyl, dibenzothiopheneyl, N-phenylcarbazoyl, benzoxazolyl, benzothiazoyl, and benzimidazolyl.

[0097] Preferably, the R j R k R m R n The following groups, independently selected from those substituted or unsubstituted by one or more of deuterium and fluorine atoms: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornane; and the following groups, substituted or unsubstituted by one or more of deuterium, fluorine, cyano, methyl, deuterated methyl, trifluoromethyl, ethyl, isopropyl, tert-butyl, cyclopropane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornane. Group: One of phenyl, naphthyl, anthracene, phenanthrene, triphenylene, biphenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirodifluorenyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, pyridinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiopheneyl, indolyl, dibenzofuranyl, dibenzothiopheneyl, N-phenylcarbazoyl, benzoxazolyl, benzothiazoyl, and benzimidazolyl.

[0098] Preferably, each time R appears, it is selected from the following groups, either identically or differently: hydrogen atom; deuterium atom; fluorine atom; cyano group; and groups substituted or unsubstituted by one or more of deuterium and fluorine atoms: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornyl; and groups substituted by deuterium, fluorine, cyano, methyl, deuterated methyl, trifluoromethyl, ethyl, isopropyl, tert-butyl, cyclopropane, cyclopentane, cyclohexane. Alkyl, cycloheptyl, adamantyl, norbornel, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, anthracene, deuterated anthracene, phenanthrene, deuterated phenanthrene, triphenylene, deuterated triphenylene, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirodifluorenyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, pyridyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiopheneyl, indoleyl, dibenzofuranyl The following silyl groups are substituted or unsubstituted with one or more of the following groups: yl, dibenzothiophene, N-phenylcarbazole, benzoxazolyl, benzothiazolyl, and benzimidazolyl; silyl groups are substituted or unsubstituted with one or more of the following groups: deuterium, fluorine, cyano, methyl, deuterated methyl, trifluoromethyl, ethyl, isopropyl, tert-butyl, cyclopropane, cyclopentane, cyclohexane, cycloheptane, adamantyl, norbornel, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, and triphenylsilyl. Group: one of phenyl, naphthyl, anthracene, phenanthrene, triphenylene, biphenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirodifluorenyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, pyridinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiopheneyl, indolyl, dibenzofuranyl, dibenzothiopheneyl, N-phenylcarbazoyl, benzoxazolyl, benzothiazoyl, and benzimidazolyl.

[0099] Preferably, the anthracene compound is selected from one of the following compounds:

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117] The above only lists some specific structural forms of anthracene compounds represented by formula (I) of the present invention. However, the present invention is not limited to these chemical structures. Any chemical structure based on formula (I) with substituents as defined in the present invention should be included.

[0118] The anthracene compounds represented by formula (I) of this invention can be prepared by the following synthetic route:

[0119]

[0120] Wherein, Q1, Q2, and Q3 are independently selected from chlorine atoms, bromine atoms, or iodine atoms, and Q1 ’ Q2 ’ Q3 ’ Independently selected from B(OH)2 or Ar1, Ar2, Ar3, L1, L2, L3, R, and a are all as described in this invention.

[0121] In the above synthetic route, the anthracene compound shown in formula (I) is obtained by reacting the halogenated compound (IA) with borate or borate ester compounds (IB), (IC), and (ID) via a CC coupling reaction. The halogenated compound (IA) can react with the borate or borate ester compounds (IB), (IC), and (ID) in one to three steps to obtain the target compound. There is no particular order in which the halogenated compound (IA) reacts with the borate or borate ester compounds (IB), (IC), and (ID). The halogenated compound (IA) can react simultaneously with the borate or borate ester compounds (IB), (IC), and (ID); it can react with one of them first, then with the remaining two simultaneously; it can react with two of them first, then with the remaining one; or it can react with one of them first, then with one of the remaining two, and finally with the remaining one.

[0122] 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.

[0123] The present invention also provides an organic electroluminescent device, comprising a first electrode, an organic layer, a second electrode, and a nucleation inhibition layer, wherein the organic layer is located on the first electrode, the second electrode is located on the organic layer, and the nucleation inhibition layer is located on the side of the second electrode away from the first electrode or between the organic layer and the second electrode, and the nucleation inhibition layer contains one or more of the anthracene compounds described in the present invention.

[0124] Preferably, the second electrode is further provided with a conductive coating on the side opposite to the first electrode.

[0125] Preferably, the second electrode has a first portion and a second portion, the nucleation inhibition layer is on the side of the first portion of the second electrode opposite to the first electrode, and the conductive coating is on the side of the second portion of the second electrode opposite to the first electrode.

[0126] The nucleation inhibition layer of this invention has a surface that exhibits a relatively low affinity for the deposition of conductive materials, thereby inhibiting the deposition of conductive materials on its surface and achieving selective deposition of conductive materials. Preferably, the nucleation inhibition layer is located on the first portion of the second electrode, allowing light to be transmitted through the first portion where no conductive material is deposited. The nucleation inhibition layer material can be an aromatic compound, preferably a compound containing anthracene, and more preferably an anthracene compound represented by formula (I) of this invention.

[0127] The conductive coating described in this invention is located on the second part of the second electrode. The materials of the conductive coating include metals and metal alloys such as lithium, magnesium, calcium, silver, copper, zinc, aluminum, and ytterbium. It mainly serves as an auxiliary electrode to reduce the IR voltage drop of the device and enable the current to be carried more effectively to various areas of the device.

[0128] Preferably, the first portion corresponds to the emitting region of the organic electroluminescent device, and the second portion corresponds to the non-emitting region of the organic electroluminescent device.

[0129] Preferably, the ratio of the first part to the second part is 5:95 to 95:5; preferably, the ratio of the first part to the second part is 10:90 to 90:10; preferably, the ratio of the first part to the second part is 20:80 to 80:20; most preferably, the ratio of the first part to the second part is 30:70 to 70:30.

[0130] The organic electroluminescent device described in this invention can be a top-emitting device, a bottom-emitting device, or a double-sided emitting device.

[0131] The first electrode described in this invention can be either an anode or a cathode. When the first electrode is an anode, the second electrode is a cathode; when the first electrode is a cathode, the second electrode is an anode. When the organic electroluminescent device described in this invention is a bottom-emitting device, the first electrode is a cathode (reflective electrode), the second electrode is an anode (transparent or semi-transparent electrode), and the nucleation inhibition layer is disposed on the side of the anode away from the cathode. When the organic electroluminescent device described in this invention is a top-emitting device, the first electrode is an anode (reflective electrode), the second electrode is a cathode (transparent or semi-transparent electrode), and the nucleation inhibition layer is disposed on the side of the cathode away from the anode. When the organic electroluminescent device described in this invention is a double-sided emitting device, one of the first electrode and the second electrode is an anode, and the other is a cathode. The nucleation inhibition layer is disposed on the side of the cathode away from the anode, and an additional nucleation inhibition layer can also be disposed on the side of the anode away from the cathode.

[0132] Preferably, the organic electroluminescent device of the present invention is a top-emitting device, the first electrode is an anode, the second electrode is a cathode, the second electrode has a first part and a second part, a nucleation inhibition layer is on the side of the first part of the second electrode opposite to the first electrode, and a conductive coating is on the side of the second part of the second electrode opposite to the first electrode.

[0133] Figure 1 A top-emitting device is shown, including an anode 100, an organic layer 200 disposed on the anode, a cathode 300 disposed on the organic layer, a nucleation inhibition layer 400 disposed on a first portion of the cathode, and a conductive coating 500 disposed on a second portion of the cathode.

[0134] 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 (IZO), 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.

[0135] 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.

[0136] The present invention also provides an organic electroluminescent device, comprising a first electrode, a second electrode, and an organic layer, wherein the organic layer is located between the first electrode and the second electrode, and the organic layer includes a hole transport region, a light-emitting layer, and an electron transport region. The light-emitting layer is located between the first electrode and the second electrode, the hole transport region is located between the first electrode and the light-emitting layer, and the electron transport region is located between the light-emitting layer and the second electrode. The light-emitting layer contains one or more anthracene compounds as described in the present invention. Preferably, the light-emitting layer comprises a host material and a guest material, and the host material contains one or more anthracene compounds as described in the present invention. Preferably, the second electrode has a capping layer on the side opposite to the first electrode.

[0137] Preferably, the organic electroluminescent device is a top-emitting device, with the first electrode being the anode and the second electrode being the cathode. The organic layer is located between the anode and the cathode, and the organic layer includes a hole transport region, a light-emitting layer, and an electron transport region. The light-emitting layer is located between the anode and the cathode, the hole transport region is located between the anode and the light-emitting layer, and the electron transport region is located between the light-emitting layer and the cathode. Preferably, the cathode has a capping layer on the side facing away from the anode.

[0138] Preferably, the organic electroluminescent device is a bottom-emitting device, with the first electrode being the anode and the second electrode being the cathode. The organic layer is located between the anode and the cathode, and the organic layer includes a hole transport region, a light-emitting layer, and an electron transport region. The light-emitting layer is located between the anode and the cathode, the hole transport region is located between the anode and the light-emitting layer, and the electron transport region is located between the light-emitting layer and the cathode.

[0139] 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 first electrode (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.

[0140] 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-19, and compounds p-1 to p-3, but not limited to these.

[0141]

[0142] 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-19 as shown above, but not limited thereto.

[0143] 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-19 as shown above, but are not limited to these.

[0144] The luminescent layer of the present invention comprises a guest material and a host material, and a dual host material formed by two host materials can be used. The guest material can be a fluorescent compound, such as pyrene derivatives, fluoranthene derivatives, aromatic amine derivatives, etc. Examples include 10-(2-benzothiazolyl)-2,3,6,7-tetrahydro-1,1,7,7-tetramethyl-1H,5H,11H-[1]benzopyran[6,7,8-ij]quinolinazine-11-one (C545T), 4,4'-bis(9-ethyl-3-carbazolevinyl)-1,1'-biphenyl (BCzVBi), 4, 4'-Bis[4-(di-p-tolylamino)styryl]biphenyl (DPAVBi) and other materials can also be used, such as phosphorescent materials, metal complexes such as iridium complexes, osmium complexes, and platinum complexes. Examples include bis(4,6-difluorophenylpyridine-N,C2)pyridineformyliridium (FIrpic), tris(2-phenylpyridine)iridium (Ir(ppy)3), and bis(2-phenylpyridine)iridium acetylacetonate (Ir(ppy)2(acac)). The host material is preferably a substance with a higher LUMO than the guest material and a lower HOMO than the guest material, such as metal complexes such as aluminum complexes or zinc complexes, heterocyclic compounds such as oxadiazole derivatives, benzoxazole derivatives, benzothiazole derivatives or benzimidazole derivatives, fused aromatic compounds such as carbazole derivatives or anthracene derivatives, and aromatic amine compounds such as triaromatic amine derivatives or fused polycyclic aromatic amine derivatives. Examples include Alq3, BAlq, TPBI, TPD, 4,4'-bis(9-carbazole)biphenyl (CBP), 4,4',4”-tris(carbazole-9-yl)triphenylamine (TCTA), 9,10-bis(2-naphthyl)anthracene (ADN), and anthracene compounds described in this invention, but are not limited thereto.

[0145] 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.

[0146] 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.

[0147] The electron transport 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. It can use aluminum complexes, lithium complexes, beryllium complexes, zinc complexes, oxazole derivatives, benzoxazole derivatives, thiazole derivatives, benzothiazole derivatives, imidazole derivatives, benzimidazole derivatives, carbazole derivatives, phenanthroline derivatives, polymers, etc. Examples 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), but is not limited to these.

[0148] 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 selected material must have 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 selected material must be lower than that of the main material of the emissive layer to effectively block holes. Further, the electron mobility of the hole-blocking layer material used is 10. -6 cm 2 A 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) and BAlq, but these are not limited to these.

[0149] The nucleation inhibition layer, conductive coating, cathode, anode, and each organic layer can be prepared by any of the following methods: vacuum evaporation, inkjet printing, sputtering, plasma, ion plating, spin coating, immersion, screen printing, etc. There are no special restrictions on the thickness of each layer, as long as good device performance is obtained.

[0150] The thickness of the nucleation inhibition layer described in this invention is typically 5 nanometers to 100 micrometers, preferably 5 nanometers to 200 nanometers, and more preferably 5 nanometers to 100 nanometers.

[0151] The thickness of the conductive coating described in this invention is typically 5 nanometers to 100 micrometers, preferably 10 nanometers to 2000 nanometers, and more preferably 30 nanometers to 200 nanometers.

[0152] The thickness of each organic layer described in this invention is typically between 1 nanometer and 100 micrometers, preferably between 5 nanometers and 1000 nanometers, and more preferably between 5 nanometers and 200 nanometers.

[0153] The thickness of the first and second electrodes in this invention is adjusted according to whether they are used as cathodes or anodes, and the required transparency.

[0154] 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.

[0155] The technical solutions and effects of the present invention will be further described below with reference to embodiments and comparative examples.

[0156] 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.

[0157] 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.

[0158] Synthesis Example 1: Synthesis of intermediates BB / DD / FF

[0159] Synthesis of intermediate DD-322:

[0160]

[0161] Under nitrogen protection, aa-322 (23.15 g, 100 mmol), bb-322 (17.30 g, 100 mmol), Pd(PPh3)4 (0.46 g, 0.4 mmol), and potassium carbonate (29.02 g, 210 mmol) were added to the reaction flask, followed by 700 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 give cc-322 (20.98 g, 75% yield); HPLC purity ≥99.86%. Mass spectrometry m / z: 279.0823 (theoretical value: 279.0815).

[0162] Under nitrogen protection, cc-322 (13.99 g, 50 mmol) and THF (110 ml) were added, and the mixture was cooled to -78 °C. 38 ml of n-butyllithium / hexane solution (1.57 mol / L) was added dropwise, and the mixture was stirred for 1 h. Triisopropyl borate (14.29 g, 76 mmol) was then added, and the mixture was stirred for another 1 h. The mixture was allowed to return to room temperature, and 53 ml of saturated ammonium chloride aqueous solution and 110 ml of toluene were added. The organic layer was washed with distilled water (3 x 100 ml), dried over anhydrous magnesium sulfate, and the magnesium sulfate was removed by filtration. The solvent was removed by vacuum distillation to obtain intermediate DD-322 (10.99 g, 76% yield). HPLC analysis showed a solid purity ≥99.87%. Mass spectrometry m / z: 289.1284 (theoretical value: 289.1274).

[0163] Synthesis of intermediate BB-384:

[0164]

[0165] Under nitrogen protection, AA-384 (13.66 g, 50 mmol) and THF (110 ml) were added, and the mixture was cooled to -78 °C. 38 ml of 1.57 mol / L butyllithium / hexane solution was added dropwise, and the mixture was stirred for 1 h. Triisopropyl borate (14.29 g, 76 mmol) was then added, and the mixture was stirred for another 1 h. The mixture was allowed to return to room temperature, and 53 ml of saturated ammonium chloride aqueous solution and 110 ml of toluene were added. The organic layer was washed with distilled water (3 x 100 ml), dried over anhydrous magnesium sulfate, and the magnesium sulfate was removed by filtration. The solvent was removed by vacuum distillation to obtain intermediate BB-384 (9.29 g, 78% yield). HPLC analysis showed a solid purity ≥99.78%. Mass spectrometry m / z: 238.1176 (theoretical value: 238.1165).

[0166] Following the synthesis steps of intermediate BB-384, by substituting the raw materials accordingly, the intermediates shown in Table 1a can be obtained:

[0167] Table 1a

[0168]

[0169] Synthesis Example 2: Synthesis of Compound 13

[0170]

[0171] Under nitrogen protection, AA-13 (62.62 g, 150 mmol), BB-13 (40.82 g, 150 mmol), potassium carbonate (31.10 g, 225 mmol), and palladium acetate (0.68 g, 3 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 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 (58.26 g, 75% yield). HPLC analysis showed a solid purity ≥99.88%. Mass spectrometry m / z: 516.0292 (theoretical value: 516.0280).

[0172] Under nitrogen protection, CC-13 (51.79 g, 100 mmol), DD-13 (12.29 g, 100 mmol), Pd(PPh3)4 (0.46 g, 0.4 mmol), and potassium carbonate (20.73 g, 150 mmol) were added to the reaction flask, followed by 1000 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-13 (37.67 g, 73%); HPLC purity ≥99.89%. Mass spectrometry m / z: 515.1455 (theoretical value: 515.1441).

[0173] Under nitrogen protection, EE-13 (25.80 g, 50 mmol), FF-13 (9.71 g, 50 mmol), potassium carbonate (10.37 g, 75 mmol), and Pd2(dba)3 (0.46 g, 0.5 mmol) were added to a reaction flask, followed by 500 mL of a toluene / ethanol / water (2:1:1) mixture. The mixture was stirred and refluxed for 6.5 hours. After the reaction was complete, the mixture was cooled to room temperature, quenched with water, and extracted with dichloromethane. The organic phases were combined, dried over anhydrous magnesium sulfate, filtered, and the filtrate was rotary evaporated and recrystallized from toluene to give compound 13 (23.62 g, 75% yield). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 629.2549 (theoretical value: 629.2539). Theoretical elemental content (%) C 46 H 35 NSi: C, 87.72; H, 5.60; N, 2.22. Measured elemental content (%): C, 87.74; H, 5.59; N, 2.23.

[0174] Synthesis Example 3: Synthesis of Compound 14

[0175]

[0176] Replacing BB-13 with an equimolar amount of BB-14, and following the same steps as in Example 2, yielded compound 14 (20.29 g, 73% yield). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 555.2389 (theoretical value: 555.2382). Theoretical elemental content (%) C 40 H 33 NSi: C, 86.44; H, 5.98; N, 2.52. Measured elemental content (%): C, 86.47; H, 5.97; N, 2.54.

[0177] Synthesis Example 4: Synthesis of Compound 33

[0178]

[0179] Replacing BB-13 with an equimolar amount of BB-33, and following the same steps as in Example 2, yielded compound 33 (25.92 g, 72% yield). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 719.3019 (theoretical value: 719.3008). Theoretical elemental content (%) C 53 H 41 NSi: C, 88.41; H, 5.74; N, 1.95. Measured elemental content (%): C, 88.45; H, 5.70; N, 1.92.

[0180] Synthesis Example 5: Synthesis of Compound 107

[0181]

[0182] By replacing BB-13 with an equimolar amount of BB-107 and DD-13 with an equimolar amount of BB-14, and following the same steps as in Synthesis Example 2, compound 107 (22.42 g, yield 74%) was obtained. HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 605.2532 (theoretical value: 605.2539). Theoretical elemental content (%) C 44 H 35 NSi: C, 87.23; H, 5.82; N, 2.31. Measured elemental content (%): C, 87.27; H, 5.80; N, 2.30.

[0183] Synthesis Example 6: Synthesis of Compound 113

[0184]

[0185] Under nitrogen protection, AA-113 (55.57 g, 150 mmol), BB-107 (51.89 g, 300 mmol), potassium carbonate (62.19 g, 450 mmol), and palladium acetate (1.35 g, 6 mmol) were added to a reaction flask, followed by 2250 mL of a toluene / ethanol / water (2:1:1) mixture. The mixture was stirred and refluxed for 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-113 (51.83 g, 74% yield). HPLC analysis showed a solid purity ≥99.89%. Mass spectrometry m / z: 466.1244 (theoretical value: 466.1237).

[0186] Under nitrogen protection, CC-113 (23.35 g, 50 mmol), FF-13 (9.71 g, 50 mmol), potassium carbonate (10.37 g, 75 mmol), and Pd2(dba)3 (0.46 g, 0.5 mmol) were added to a reaction flask, followed by 500 mL of a toluene / ethanol / water (2:1:1) mixture. The mixture was stirred and refluxed for 6.5 hours. After the reaction was complete, the mixture was cooled to room temperature, quenched with water, and extracted with dichloromethane. The organic phases were combined, dried over anhydrous magnesium sulfate, filtered, and the filtrate was rotary evaporated and recrystallized from toluene to give compound 113 (20.91 g, 72% yield). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 580.2346 (theoretical value: 580.2335). Theoretical elemental content (%) C 41 H 32 N₂Si: C, 84.79; H, 5.55; N, 4.82. Measured elemental content (%): C, 84.73; H, 5.59; N, 4.85.

[0187] Synthesis Example 7: Synthesis of Compound 131

[0188]

[0189] By replacing BB-13 with an equimolar amount of BB-131 and DD-13 with an equimolar amount of DD-131, and following the same steps as in Synthesis Example 2, compound 131 (21.20 g, yield 73%) was obtained. HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 580.2346 (theoretical value: 580.2335). Theoretical elemental content (%) C 41 H 32 N₂Si: C, 84.79; H, 5.55; N, 4.82. Measured elemental content (%): C, 84.83; H, 5.53; N, 4.85.

[0190] Synthesis Example 8: Synthesis of Compound 141

[0191]

[0192] By replacing BB-13 with an equimolar amount of BB-141 and DD-13 with an equimolar amount of BB-14, and following the same steps as in Synthesis Example 2, compound 141 (24.63 g, yield 75%) was obtained. HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 656.2641 (theoretical value: 656.2648). Theoretical elemental content (%) C 47 H 36N₂Si: C, 85.94; H, 5.52; N, 4.26. Measured elemental content (%): C, 85.98; H, 5.49; N, 4.24.

[0193] Synthesis Example 9: Synthesis of Compound 143

[0194]

[0195] By replacing BB-13 with an equimolar amount of BB-143 and DD-13 with an equimolar amount of DD-143, and following the same steps as in Synthesis Example 2, compound 143 (20.29 g, yield 73%) was obtained. HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 555.2390 (theoretical value: 555.2382). Theoretical elemental content (%) C 40 H 33 NSi: C, 86.44; H, 5.98; N, 2.52. Measured elemental content (%): C, 86.51; H, 5.96; N, 2.49.

[0196] Synthesis Example 10: Synthesis of Compound 163

[0197]

[0198] By replacing BB-13 with an equimolar amount of BB-14 and DD-13 with an equimolar amount of DD-163, and following the same steps as in Synthesis Example 2, compound 163 (23.38 g, yield 74%) was obtained. HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 631.2688 (theoretical value: 631.2695). Theoretical elemental content (%) C 46 H 37 NSi: C, 87.44; H, 5.90; N, 2.22. Measured elemental content (%): C, 87.48; H, 5.88; N, 2.19.

[0199] Synthesis Example 11: Synthesis of Compound 192

[0200]

[0201] By replacing BB-13 with an equimolar amount of BB-192 and DD-13 with an equimolar amount of DD-192, and following the same steps as in Synthesis Example 2, compound 192 (24.56 g, yield 73%) was obtained. HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 672.2970 (theoretical value: 672.2961). Theoretical elemental content (%) C 48 H 40N₂Si: C, 85.67; H, 5.99; N, 4.16. Measured elemental content (%): C, 85.64; H, 5.97; N, 4.20.

[0202] Synthesis Example 12: Synthesis of Compound 199

[0203]

[0204] By replacing BB-13 with an equimolar amount of BB-143 and DD-13 with an equimolar amount of DD-199, and following the same steps as in Synthesis Example 2, compound 199 (26.62 g, yield 75%) was obtained. HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 709.2924 (theoretical value: 709.2913). Theoretical elemental content (%) C 50 H 39 N3Si: C, 84.59; H, 5.54; N, 5.92. Measured elemental content (%): C, 84.54; H, 5.56; N, 5.96.

[0205] Synthesis Example 13: Synthesis of Compound 206

[0206]

[0207] By replacing BB-13 with an equimolar amount of BB-143 and DD-13 with an equimolar amount of DD-206, and following the same steps as in Synthesis Example 2, compound 206 (21.81 g, yield 72%) was obtained. HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 605.2530 (theoretical value: 605.2539). Theoretical elemental content (%) C 44 H 35 NSi: C, 87.23; H, 5.82; N, 2.31. Measured elemental content (%): C, 87.20; H, 5.84; N, 2.36.

[0208] Synthesis Example 14: Synthesis of Compound 220

[0209]

[0210] By replacing BB-13 with an equimolar amount of BB-14 and DD-13 with an equimolar amount of DD-220, and following the same steps as in Synthesis Example 2, compound 220 (24.89 g, yield 73%) was obtained. HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 681.2872 (theoretical value: 681.2852). Theoretical elemental content (%) C 50 H 39NSi: C, 88.06; H, 5.76; N, 2.05. Measured elemental content (%): C, 88.09; H, 5.74; N, 2.07.

[0211] Synthesis Example 15: Synthesis of Compound 223

[0212]

[0213] By replacing BB-13 with an equimolar amount of BB-223 and DD-13 with an equimolar amount of DD-220, and following the same steps as in Synthesis Example 2, compound 223 (25.75 g, yield 74%) was obtained. HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 695.2632 (theoretical value: 695.2644). Theoretical elemental content (%) C 50 H 37 NOSi: C, 86.29; H, 5.36; N, 2.01. Measured elemental content (%): C, 86.26; H, 5.37; N, 2.02.

[0214] Synthesis Example 16: Synthesis of Compound 229

[0215]

[0216] By replacing BB-13 with an equimolar amount of BB-14 and DD-13 with an equimolar amount of DD-229, and following the same steps as in Synthesis Example 2, compound 229 (24.93 g, yield 73%) was obtained. HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 682.2815 (theoretical value: 682.2804). Theoretical elemental content (%) C 49 H 38 N₂Si: C, 86.18; H, 5.61; N, 4.10. Measured elemental content (%): C, 86.12; H, 5.64; N, 4.14.

[0217] Synthesis Example 17: Synthesis of Compound 241

[0218]

[0219] By replacing BB-13 with an equimolar amount of BB-241 and DD-13 with an equimolar amount of DD-241, and following the same steps as in Synthesis Example 2, compound 241 (24.86 g, yield 74%) was obtained. HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 671.3019 (theoretical value: 671.3008). Theoretical elemental content (%) C 49 H 41NSi: C, 87.59; H, 6.15; N, 2.08. Measured elemental content (%): C, 87.57; H, 6.18; N, 2.10.

[0220] Synthesis Example 18: Synthesis of Compound 271

[0221]

[0222] By replacing BB-13 with an equimolar amount of BB-143 and DD-13 with an equimolar amount of DD-271, and following the same steps as in Synthesis Example 2, compound 271 (22.72 g, yield 75%) was obtained. HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 605.2532 (theoretical value: 605.2539). Theoretical elemental content (%) C 44 H 35 NSi: C, 87.23; H, 5.82; N, 2.31. Measured elemental content (%): C, 87.26; H, 5.80; N, 2.33.

[0223] Synthesis Example 19: Synthesis of Compound 322

[0224]

[0225] By replacing BB-13 with an equimolar amount of BB-143 and DD-13 with an equimolar amount of DD-322, and following the same steps as in Synthesis Example 2, compound 322 (23.25 g, yield 72%) was obtained. HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 645.2863 (theoretical value: 645.2852). Theoretical elemental content (%) C 47 H 39 NSi: C, 87.40; H, 6.09; N, 2.17. Measured elemental content (%): C, 87.42; H, 6.06; N, 2.19.

[0226] Synthesis Example 20: Synthesis of Compound 342

[0227]

[0228] By replacing BB-13 with an equimolar amount of BB-342 and DD-13 with an equimolar amount of DD-342, and following the same steps as in Synthesis Example 2, compound 342 (22.45 g, yield 74%) was obtained. HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 606.2499 (theoretical value: 606.2491). Theoretical elemental content (%) C 43 H 34N₂Si: C, 85.11; H, 5.65; N, 4.62. Measured elemental content (%): C, 85.12; H, 5.63; N, 4.66.

[0229] Synthesis Example 21: Synthesis of Compound 366

[0230]

[0231] Replacing BB-13 with an equimolar amount of BB-366, and following the same steps as in Synthesis Example 2, yielded compound 366 (23.94 g, 73% yield). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 655.2681 (theoretical value: 655.2695). Theoretical elemental content (%) C 48 H 37 NSi: C, 87.90; H, 5.69; N, 2.14. Measured elemental content (%): C, 87.93; H, 5.71; N, 2.15.

[0232] Synthesis Example 22: Synthesis of Compound 384

[0233]

[0234] By replacing BB-13 with an equimolar amount of BB-384 and DD-13 with an equimolar amount of DD-143, and following the same steps as in Synthesis Example 2, compound 384 (24.86 g, yield 74%) was obtained. HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 671.3019 (theoretical value: 671.3008). Theoretical elemental content (%) C 49 H 41 NSi: C, 87.59; H, 6.15; N, 2.08. Measured elemental content (%): C, 87.60; H, 6.17; N, 2.04.

[0235] Synthesis Example 23: Synthesis of Compound 391

[0236]

[0237] By replacing BB-13 with an equimolar amount of BB-391 and DD-13 with an equimolar amount of DD-143, and following the same steps as in Synthesis Example 2, compound 391 (25.57 g, yield 75%) was obtained. HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 681.2863 (theoretical value: 681.2852). Theoretical elemental content (%) C 50 H 39NSi: C, 88.06; H, 5.76; N, 2.05. Measured elemental content (%): C, 88.10; H, 5.77; N, 2.01.

[0238] Synthesis Example 24: Synthesis of Compound 394

[0239]

[0240] By replacing BB-13 with an equimolar amount of BB-394 and DD-13 with an equimolar amount of DD-271, and following the same steps as in Synthesis Example 2, compound 394 (27.45 g, 75% yield) was obtained. HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 731.3001 (theoretical value: 731.3008). Theoretical elemental content (%) C 54 H 41 NSi: C, 88.60; H, 5.65; N, 1.91. Measured elemental content (%): C, 88.63; H, 5.63; N, 1.92.

[0241] Synthesis Example 25: Synthesis of Compound 431

[0242]

[0243] By replacing BB-13 with an equimolar amount of BB-14, DD-13 with an equimolar amount of DD-143, and FF-13 with an equimolar amount of FF-431, and following the same steps as in Synthesis Example 2, compound 431 (23.53 g, yield 74%) was obtained. HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 635.2930 (theoretical value: 635.2946). Theoretical elemental content (%) C 46 H 33 D4NSi: C, 86.88; H, 6.50; N, 2.20. Measured elemental content (%): C, 86.87; H, 6.51; N, 2.23.

[0244] Synthesis Example 26: Synthesis of Compound 437

[0245]

[0246] By replacing BB-13 with an equimolar amount of BB-14, DD-13 with an equimolar amount of DD-437, and FF-13 with an equimolar amount of FF-437, and following the same steps as in Synthesis Example 2, compound 437 (22.92 g, yield 73%) was obtained. HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 627.2789 (theoretical value: 627.2778). Theoretical elemental content (%) C 43 H 41 NSi2: C, 82.24; H, 6.58; N, 2.23. Measured elemental content (%): C, 82.26; H, 6.61; N, 2.16.

[0247] Synthesis Example 27: Synthesis of Compound 449

[0248]

[0249] By replacing BB-13 with an equimolar amount of BB-14, DD-13 with an equimolar amount of DD-143, and FF-13 with an equimolar amount of FF-449, and following the same steps as in Synthesis Example 2, compound 449 (24.94 g, yield 74%) was obtained. HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 673.3153 (theoretical value: 673.3165). Theoretical elemental content (%) C 49 H 43 NSi: C, 87.32; H, 6.43; N, 2.08. Measured elemental content (%): C, 87.30; H, 6.42; N, 2.13.

[0250] Synthesis Example 28: Synthesis of Compound 456

[0251]

[0252] By replacing BB-13 with an equimolar amount of BB-143, DD-13 with an equimolar amount of DD-143, and FF-13 with an equimolar amount of FF-456, and following the same steps as in Synthesis Example 2, compound 456 (27.83 g, yield 75%) was obtained. HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 741.2863 (theoretical value: 741.2852). Theoretical elemental content (%) C 55 H 39 NSi: C, 89.03; H, 5.30; N, 1.89. Measured elemental content (%): C, 89.06; H, 5.28; N, 1.87.

[0253] Synthesis Example 29: Synthesis of Compound 493

[0254]

[0255] By replacing BB-13 with an equimolar amount of BB-14, DD-13 with an equimolar amount of DD-143, and FF-13 with an equimolar amount of FF-493, and following the same steps as in Synthesis Example 2, compound 493 (22.78 g, yield 72%) was obtained. HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 632.2640 (theoretical value: 632.2648). Theoretical elemental content (%) C 45 H 36 N₂Si: C, 85.40; H, 5.73; N, 4.43. Measured elemental content (%): C, 85.44; H, 5.71; N, 4.42.

[0256] Synthesis Example 30: Synthesis of Compound 498

[0257]

[0258] By replacing BB-13 with an equimolar amount of BB-14 and FF-13 with an equimolar amount of FF-498, and following the same steps as in Synthesis Example 2, compound 498 (23.90 g, yield 74%) was obtained. HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 645.2475 (theoretical value: 645.2488). Theoretical elemental content (%) C 46 H 35 NOSi: C, 85.54; H, 5.46; N, 2.17. Measured elemental content (%): C, 85.52; H, 5.48; N, 2.20.

[0259] Synthesis Example 31: Synthesis of Compound 507

[0260]

[0261] Under nitrogen protection, AA-507 (60.74 g, 150 mmol), DD-143 (59.70 g, 300 mmol), potassium carbonate (62.19 g, 450 mmol), and palladium acetate (1.35 g, 6 mmol) were added to a reaction flask, followed by 2250 mL of a toluene / ethanol / water (2:1:1) mixture. The mixture was stirred and refluxed for 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-507 (62.27 g, 75% yield). HPLC analysis showed a solid purity ≥99.87%. Mass spectrometry m / z: 552.1171 (theoretical value: 552.1160).

[0262] Under nitrogen protection, CC-507 (27.67 g, 50 mmol), FF-13 (19.41 g, 100 mmol), potassium carbonate (20.73 g, 150 mmol), and Pd2(dba)3 (0.92 g, 1 mmol) were added to a reaction flask, followed by 750 mL of a toluene / ethanol / water (2:1:1) mixture. The mixture was stirred and 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 compound 507 (28.51 g, yield 73%). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 780.3369 (theoretical value: 780.3356). Theoretical elemental content (%) C 54 H 48 N₂Si: C, 83.03; H, 6.19; N, 3.59. Measured elemental content (%): C, 83.02; H, 6.17; N, 3.61.

[0263] Synthesis Example 32: Synthesis of Compound 529

[0264]

[0265] By replacing BB-13 with an equimolar amount of BB-529 and DD-13 with an equimolar amount of DD-529, and following the same steps as in Synthesis Example 2, compound 529 (20.75 g, yield 74%) was obtained. HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 560.2681 (theoretical value: 560.2696). Theoretical elemental content (%) C 40 H 28D5NSi: C, 85.67; H, 6.83; N, 2.50. Measured elemental content (%): C, 85.69; H, 6.84; N, 2.52.

[0266] Synthesis Example 33: Synthesis of Compound 554

[0267]

[0268] By replacing BB-13 with an equimolar amount of BB-554 and DD-13 with an equimolar amount of DD-554, and following the same steps as in Synthesis Example 2, compound 554 (25.80 g, yield 75%) was obtained. HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 687.3331 (theoretical value: 687.3321). Theoretical elemental content (%) C 50 H 45 NSi: C, 87.29; H, 6.59; N, 2.04. Measured elemental content (%): C, 87.26; H, 6.58; N, 2.07.

[0269] Synthesis Example 34: Synthesis of Compound 563

[0270]

[0271] By replacing BB-13 with an equimolar amount of BB-143 and DD-13 with an equimolar amount of DD-563, and following the same steps as in Synthesis Example 2, compound 563 (25.91 g, yield 73%) was obtained. HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 709.2906 (theoretical value: 709.2913). Theoretical elemental content (%) C 50 H 39 N3Si: C, 84.59; H, 5.54; N, 5.92. Measured elemental content (%): C, 84.56; H, 5.56; N, 5.94.

[0272] Device Examples

[0273] Nucleation inhibition materials

[0274] Testing instrument: UV-Vis spectrophotometer (manufacturer: Shanghai Xipu Instrument Co., Ltd., model: UV-2202PC)

[0275] Comparative Example 1: Comparative Sample 1

[0276] First, a 20 nm thick layer of the comparative compound Ref-1 was deposited on a glass substrate as a nucleation inhibition layer. Then, magnesium was deposited on the surface of the nucleation inhibition coating using an open mask, subjecting the sample to an average evaporation rate of [missing information]. The magnesium vapor flux was used to obtain a reference layer thickness of approximately 50 nm for magnesium coating deposition using a deposition time of 200 seconds. Optical transmittance measurements were used to determine the relative amount of magnesium deposited on the nucleation inhibition coating surface. Any light loss or absorption caused by the presence of the glass substrate and nucleation inhibition coating was subtracted from the measured transmittance when calculating the optical transmittance (valued at a wavelength of 550 nm).

[0277]

[0278] Examples 1-33: Samples 1-33

[0279] Replace the comparative compound Ref-1 in Comparative Example 1 with the following anthracene compounds described in this invention: compound 13, compound 14, compound 33, compound 107, compound 113, compound 131, compound 141, compound 143, compound 163, compound 192, compound 199, compound 206, compound 220, compound 223, compound 229, compound 241, compound 271, compound 322, compound 342, compound 366, compound 384, compound 391, compound 394, compound 431, compound 437, compound 449, compound 456, compound 493, compound 498, compound 507, compound 529, compound 554, and compound 563. All other steps are the same as in Comparative Example 1 to obtain samples 1 to 33.

[0280] The optical transmittance test results of the samples prepared in Comparative Example 1 and Examples 1 to 33 are shown in Table 2.

[0281] Table 2 Optical transmittance test data

[0282]

[0283]

[0284] As shown in Table 2, compared to Comparative Example 1, the sample prepared using the anthracene compound of Formula (I) of the present invention has higher optical transmittance, indicating that a relatively small amount of magnesium coating exists on its surface to absorb light transmitted through the sample. Therefore, applying the anthracene compound of Formula (I) of the present invention as a nucleation inhibition layer in OLED devices can achieve selective deposition of conductive materials, patterning of the cathode, reduction of IR voltage drop in the device, and ensure high light transmittance.

[0285] Main materials

[0286] The following are compounds other than the anthracene compounds described in this invention used in the device fabrication examples:

[0287]

[0288]

[0289] A combined IVL testing system was constructed, consisting of testing software, a computer, a Keithley K2400 digital source meter, and a Photo Research PR788 spectrophotometer. The device prepared according to this invention was tested at atmospheric pressure and room temperature at a current density of 15 mA / cm². 2 The luminous efficiency and driving voltage were 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 Table 3.

[0290] Comparative device fabrication example 1: Comparative device 1

[0291] 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.

[0292] The following layers were deposited layer by layer on the aforementioned ITO / Ag / ITO glass substrate: a) HT-2 and p-1 (mass ratio 100:1) as hole injection layer with a thickness of 10 nm; b) HT-2 as hole transport layer with a thickness of 110 nm; c) HOST-1 and BD (mass ratio 94:6) as light-emitting layer with a thickness of 20 nm; d) TPBi as hole blocking layer with a thickness of 5 nm; e) NBphen and Liq (mass ratio 5:5) as electron transport layer with a thickness of 25 nm; f) LiF as electron injection layer with a thickness of 1 nm; g) Mg and Ag (mass ratio 1:9) as cathode with a thickness of 10 nm; h) CP-4 as capping layer with a thickness of 75 nm.

[0293] Comparative device fabrication examples 2-3: Comparative devices 2-3

[0294] By replacing HOST-1 in the light-emitting layer with compounds HOST-2 and HOST-3 respectively, and following the same steps as in Comparative Device Preparation Example 1, Comparative Devices 2 and 3 can be obtained.

[0295] Device fabrication examples 1-33: Light-emitting devices 1-33

[0296] By replacing HOST-1 in the light-emitting layer with the anthracene compounds described in this invention as follows: compound 13, compound 14, compound 33, compound 107, compound 113, compound 131, compound 141, compound 143, compound 163, compound 192, compound 199, compound 206, compound 220, compound 223, compound 229, compound 241, compound 271, compound 322, compound 342, compound 366, compound 384, compound 391, compound 394, compound 431, compound 437, compound 449, compound 456, compound 493, compound 498, compound 507, compound 529, compound 554, and compound 563, light-emitting devices 1 to 33 can be obtained.

[0297] The optical performance test results of the devices prepared in Comparative Device Preparation Examples 1-3 and 1-33 are shown in Table 3.

[0298] Table 3 Optical performance test data

[0299]

[0300]

[0301]

[0302] The device data in Table 3 show that, using the anthracene compounds provided by this invention as the main material of the light-emitting layer, the driving voltage, luminous efficiency, and lifespan of the device are all improved.

[0303] 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 anthracene compound, characterized in that, The anthracene compound has the structure shown in formula (I): Wherein, Ar1 is selected from C2-C30 nitrogen-containing heteroaryl groups substituted with one or more R1s, and the heteroatoms in the nitrogen-containing heteroaryl group are selected only from -N=. Each time R1 appears, it is selected from one of the following groups: hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 alkyl group, substituted or unsubstituted C3-C12 cycloalkyl group, substituted or unsubstituted C6-C30 aryl group, monovalent group formed by fusion of substituted or unsubstituted C3-C20 aliphatic ring and C6-C30 aromatic ring, and substituted or unsubstituted C2-C30 heteroaryl group. The Ar2 is selected from one of the following groups substituted with one or more R2: aryl (C6-C30), monovalent group formed by fusion of aliphatic ring and aromatic ring (C3-C20), and heteroaryl (C2-C30); each time the R2 appears, it is selected from one of the following groups, either the same or different: hydrogen atom, deuterium atom, halogen atom, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, monovalent group formed by fusion of aliphatic ring and aromatic ring (C3-C20), and heteroaryl (C2-C30); The Ar3 is selected from one of the following groups substituted with one or more R3s: aryl of C6-C30, monovalent group formed by fusion of aliphatic ring of C3-C20 and aromatic ring of C6-C30, and heteroaryl of C2-C30; each time the R3 appears, it is selected from one of the following groups, either the same or different: hydrogen atom, deuterium atom, halogen atom, cyano, substituted or unsubstituted alkyl of C1-C12, substituted or unsubstituted cycloalkyl of C3-C12, substituted or unsubstituted silyl, substituted or unsubstituted aryl of C6-C30, monovalent group formed by fusion of aliphatic ring of C3-C20 and aromatic ring of C6-C30, and heteroaryl of C2-C30, and at least one R3 is selected from substituted or unsubstituted silyl; The 'a' is selected from 0, 1, 2, 3, 4, 5, 6, or 7; Each time R appears, it is selected from one of the following, either the same or different: hydrogen atom, deuterium 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, a monovalent group formed by fusion of a substituted or unsubstituted C3-C20 aliphatic ring and a C6-C30 aromatic ring, or substituted or unsubstituted C2-C30 heteroaryl group. The L1, L2, and L3 are independently selected from single bonds, substituted or unsubstituted C6-C25 arylene groups, divalent groups formed by the fusion of substituted or unsubstituted C3-C10 aliphatic rings and C6-C25 aromatic rings, substituted or unsubstituted C2-C20 heteroarylene groups, or combinations thereof.

2. The anthracene compound according to claim 1, characterized in that, The Ar1 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, or 3; each occurrence of c1 is selected from 0, 1, or 2; each occurrence of d1 is selected from 0, 1, 2, 3, 4, 5, or 6; each occurrence of e1 is selected from 0, 1, 2, 3, 4, or 5; each occurrence of f1 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; and each occurrence of g1 is selected from 0, 1, 2, 3, 4, 5, 6, or 7. Each time R1 appears, it is selected from one of the following groups, either the same or different: hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 alkyl group, substituted or unsubstituted C3-C12 cycloalkyl group, substituted or unsubstituted C6-C30 aryl group, a monovalent group formed by fusion of a substituted or unsubstituted C3-C20 aliphatic ring and a C6-C30 aromatic ring, or substituted or unsubstituted C2-C30 heteroaryl group.

3. The anthracene compound according to claim 1, characterized in that, The Ar2 group is selected from one of the following groups: Wherein, each occurrence of a2 is selected from 0, 1, 2, 3, 4, or 5; each occurrence of b2 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; each occurrence of c2 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; each occurrence of d2 is selected from 0, 1, 2, 3, or 4; each occurrence of e2 is selected from 0, 1, 2, or 3; and each occurrence of f2 is selected from 0, 1, 2, or 3. The values ​​of g2 and h2 are selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8, respectively. g2 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11, respectively. h2 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, or 13, respectively. i2 is selected from 0, 1, 2, 3, 4, 5, or 6, respectively. j2 is selected from 0, 1, or 2, respectively. Each time R2 appears, it is selected from one of the following groups, either the same or different: hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 alkyl group, substituted or unsubstituted C3-C12 cycloalkyl group, substituted or unsubstituted C6-C30 aryl group, a monovalent group formed by fusion of a substituted or unsubstituted C3-C20 aliphatic ring and a C6-C30 aromatic ring, or substituted or unsubstituted C2-C30 heteroaryl group. Z1 is selected from oxygen atoms, sulfur atoms, and CR. a R b or NR c ; The Z2 is selected from oxygen atoms, sulfur atoms, or NR. d ; The R mentioned a R b R c R d It is independently selected from one of the following: substituted or unsubstituted C1-C12 alkyl groups, substituted or unsubstituted C3-C12 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, a monovalent group formed by fusion of a substituted or unsubstituted C3-C20 aliphatic ring and a C6-C30 aromatic ring, or substituted or unsubstituted C2-C30 heteroaryl groups.

4. The anthracene compound according to claim 1, characterized in that, The Ar3 is selected from one of the following groups: Wherein, each occurrence of a3 is selected from 0, 1, 2, 3, or 4; each occurrence of b3 is selected from 0, 1, 2, 3, 4, 5, or 6; each occurrence of c3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; each occurrence of d3 is selected from 0, 1, 2, or 3; each occurrence of e3 is selected from 0, 1, or 2; each occurrence of f3 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; each occurrence of g3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; each occurrence of h3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12; and each occurrence of i3 is selected from 0, 1, 2, 3, 4, or 5. Each time R3 appears, it is selected from one of the following groups, either the same or different: hydrogen atom, deuterium 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, a monovalent group formed by fusion of a substituted or unsubstituted C3-C20 aliphatic ring and a C6-C30 aromatic ring, or substituted or unsubstituted C2-C30 heteroaryl group. The Z3 is selected from oxygen atoms, sulfur atoms, and CR. f R g or NR h ; The Z4 is selected from oxygen atoms, sulfur atoms, or NR. i ; The R mentioned f R g R h R i It is independently selected from one of the following: substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, a monovalent group formed by fusion of a substituted or unsubstituted C3-C20 aliphatic ring and a C6-C30 aromatic ring, or substituted or unsubstituted C2-C30 heteroaryl. The R mentioned e Each time it appears, it is selected from the same or different groups of hydrogen atom, deuterium atom, 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, a monovalent group formed by fusion of a substituted or unsubstituted C3-C20 aliphatic ring and a C6-C30 aromatic ring, and substituted or unsubstituted C2-C30 heteroaryl group.

5. The anthracene compound according to claim 4, characterized in that, The R mentioned e Each time it appears, it is selected from the same or different groups: hydrogen atom; deuterium atom; and the following groups substituted or unsubstituted by one or more of deuterium atom and fluorine atom: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornane; and is substituted by one or more of deuterium atom, fluorine atom, cyano, methyl, deuterated methyl, trifluoromethyl, ethyl, isopropyl, tert-butyl, cyclopropane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornane. The following groups, substituted or unsubstituted, are included: phenyl, naphthyl, anthracene, phenanthrene, triphenylene, biphenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirodifluorenyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, pyridinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiopheneyl, indolyl, dibenzofuranyl, dibenzothiopheneyl, N-phenylcarbazoyl, benzoxazolyl, benzothiazoyl, and benzimidazolyl.

6. The anthracene compound according to claim 4, characterized in that, The aforementioned Choose one of the following structures: 。 7. The anthracene compound according to claim 1, characterized in that, The L1 and L2 are independently selected from single bonds, groups as shown below, or combinations thereof: Wherein, each occurrence of a4 is selected from 0, 1, 2, 3, or 4; each occurrence of b4 is selected from 0, 1, 2, or 3; each occurrence of c4 is selected from 0, 1, or 2; each occurrence of d4 is selected from 0, 1, 2, 3, 4, 5, or 6; each occurrence of e4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; each occurrence of f4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; each occurrence of g4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12; and each occurrence of h4 is selected from 0 or 1. Each time R4 appears, it is selected from one of the following groups, either the same or different: hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 alkyl group, substituted or unsubstituted C3-C12 cycloalkyl group, substituted or unsubstituted C6-C30 aryl group, a monovalent group formed by fusion of a substituted or unsubstituted C3-C20 aliphatic ring and a C6-C30 aromatic ring, or substituted or unsubstituted C2-C30 heteroaryl group. The E1 is selected from oxygen atoms, sulfur atoms, and CR. j R k or NR m ; The E2 is selected from oxygen atoms, sulfur atoms, or NR. n ; The R mentioned j R k R m R n It is independently selected from one of the following: substituted or unsubstituted C1-C12 alkyl groups, substituted or unsubstituted C3-C12 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, a monovalent group formed by fusion of a substituted or unsubstituted C3-C20 aliphatic ring and a C6-C30 aromatic ring, or substituted or unsubstituted C2-C30 heteroaryl groups.

8. The anthracene compound according to claim 1, characterized in that, Each time R appears, it is selected from the following groups, either identically or differently: hydrogen atom; deuterium atom; fluorine atom; cyano group; and groups substituted or unsubstituted by one or more of deuterium and fluorine atoms: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornyl; and groups substituted by deuterium, fluorine, cyano, methyl, deuterated methyl, trifluoromethyl, ethyl, isopropyl, tert-butyl, cyclopropane, cyclopentane, cyclohexane. Cycloheptyl, adamantyl, norbornel, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, anthracene, deuterated anthracene, phenanthryl, deuterated phenanthryl, triphenylene, deuterated triphenylene, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirodifluorenyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, pyridinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiopheneyl, indoleyl, dibenzofuranyl The following silyl groups are substituted or unsubstituted with one or more of the following groups: dibenzothiophene, N-phenylcarbazole, benzoxazolyl, benzothiazolyl, and benzimidazolyl; or are substituted or unsubstituted with one or more of the following groups: deuterium, fluorine, cyano, methyl, deuterated methyl, trifluoromethyl, ethyl, isopropyl, tert-butyl, cyclopropane, cyclopentane, cyclohexane, cycloheptane, adamantyl, norbornel, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, and triphenylsilyl. One of the following: phenyl, naphthyl, anthracene, phenanthrene, triphenylene, biphenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirodifluorenyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, pyridinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiopheneyl, indolyl, dibenzofuranyl, dibenzothiopheneyl, N-phenylcarbazoyl, benzoxazolyl, benzothiazoyl, and benzimidazolyl.

9. The anthracene compound according to claim 1, characterized in that, The anthracene compounds are selected from one of the following compounds: 。 10. An organic electroluminescent device, comprising a first electrode, an organic layer, a second electrode, and a nucleation inhibition layer, wherein the organic layer is located on the first electrode, the second electrode is located on the organic layer, and the nucleation inhibition layer is located on the side of the second electrode opposite to the first electrode or between the organic layer and the second electrode, characterized in that, The nucleation inhibition layer contains one or more of the anthracene compounds described in any one of claims 1 to 9.

11. An organic electroluminescent device, comprising a first electrode, a second electrode, and an organic layer, wherein the organic layer is located between the first electrode and the second electrode, the organic layer comprising a hole transport region, a light-emitting layer, and an electron transport region, wherein the light-emitting layer is located between the first electrode and the second electrode, the hole transport region is located between the first electrode and the light-emitting layer, and the electron transport region is located between the light-emitting layer and the second electrode, characterized in that, The light-emitting layer contains one or more of the anthracene compounds as described in any one of claims 1 to 9.

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