Anthracene compound and organic electroluminescent device thereof

Abstract

The invention relates to the technical field of organic photoelectric materials, in particular to an anthracene compound and an organic electroluminescent device thereof. The anthracene compound as shown in the formula (I) forms a film structure 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 an auxiliary electrode is deposited on the outer side of an electrode on the light-transmitting side, the conductivity of the electrode on the light-transmitting side is improved. The selective deposition of the conductive material can be realized, the IR voltage drop of the device is reduced, and the high transmittance of light can be ensured. When the anthracene compound provided by the invention is applied to an OLED device as a main body material, excellent device performances such as luminous efficiency, driving voltage, service life and the like can 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] Classic OLED devices have a "sandwich" structure, with an emissive layer sandwiched between two electrodes, a cathode and an anode. The emissive layer contains a luminescent material (guest material). When an electric current is applied to the electrodes, holes and electrons are injected from the anode and cathode, respectively, and reach the emissive layer. They then recombine to generate excitons, releasing energy. Under the influence of an electric field, the excitons migrate and transfer energy to the luminescent material. Electrons in the luminescent material molecules transition from the ground state to the excited state. Since the excited state is unstable, the electrons return from the excited state to the ground state, thus releasing energy in the form of light and producing the luminescence phenomenon.

[0004] Based on the different light emission paths, OLEDs can be divided into bottom-emitting devices 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 to the outside of the device. Top-emitting devices emit light directly from the cathode side, eliminating the need for a 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 for greater 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 the OLED.

[0005] Cathode patterning technology can reduce IR voltage drop loss in the OLED cathode layer. This technology 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. Currently, the types of nucleation inhibition materials are relatively limited, and their effectiveness is not ideal. Therefore, developing novel nucleation inhibition materials has significant practical application value. Summary of the Invention

[0006] To solve the above-mentioned technical problems, the present invention provides an anthracene compound having the structure shown in formula (I):

[0007]

[0008] The 'a' is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the 'b' is selected from 0, 1, or 2.

[0009] 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 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.

[0010] Each time R2 appears, it is selected from one of the following, either the same or different: hydrogen atom, deuterium atom, halogen 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.

[0011] The X is selected from oxygen atoms or sulfur atoms;

[0012] The ring A is selected from one of the following groups substituted or unsubstituted by one or more R3s: an aromatic ring of C6 to C30, a ring formed by the fusion of an aliphatic ring of C3 to C20 and an aromatic ring of C6 to C30, and a heteroaromatic ring of C2 to C30; each time the R3 appears, it is selected from one of the following groups, either the same or different: a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group of C1 to C12, a substituted or unsubstituted cycloalkyl group of C3 to C12, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group 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 substituted or unsubstituted heteroaromatic group of C2 to C30;

[0013] The Ar is selected from one of the following groups substituted with one or more R4s: 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 R4 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 R4 is selected from a substituted or unsubstituted silyl.

[0014] The L1 and L2 are independently selected from single bonds, C6-C30 aryl groups substituted or unsubstituted with one or more R5s, divalent groups formed by the fusion of a C3-C20 aliphatic ring substituted or unsubstituted with one or more R5s and a C6-C30 aromatic ring, C2-C30 heteroaryl groups substituted or unsubstituted with one or more R5s, or combinations thereof; each time the R5 appears, it is selected from the same or different groups of hydrogen atoms, deuterium atoms, halogen atoms, cyano groups, substituted or unsubstituted C1-C12 alkyl groups, substituted or unsubstituted C3-C12 cycloalkyl groups, substituted or unsubstituted silyl groups, substituted or unsubstituted C6-C30 aryl groups, monovalent groups formed by the fusion of a C3-C20 aliphatic ring substituted or unsubstituted with a C6-C30 aromatic ring, and substituted or unsubstituted C2-C30 heteroaryl groups containing nitrogen atoms.

[0015] The present invention also provides an organic electroluminescent device, comprising a first electrode, a second electrode, an organic layer, and a nucleation inhibition layer, wherein the organic layer is located between the first electrode and the second electrode, and the nucleation inhibition layer is located on the side of the second electrode opposite to the first electrode, and the nucleation inhibition layer contains one or more of the anthracene compounds described in the present invention.

[0016] The present invention also provides an organic electroluminescent device, comprising a first electrode, a second electrode, an organic layer, and a nucleation inhibition layer, wherein the organic layer is located between the first electrode and the second electrode, and the nucleation inhibition layer is located 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.

[0017] 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 one or more of the anthracene compounds described in the present invention.

[0018] Beneficial effects:

[0019] The anthracene compound of formula (I) provided by this invention forms a film structure through a vapor deposition process. Its surface exhibits a relatively low affinity for conductive materials, suppressing their deposition. This allows for selective deposition of conductive materials when depositing an auxiliary electrode on the outer side of the light-transmitting electrode, reducing the IR voltage drop of the device while maintaining high light transmittance. When the anthracene compound provided by this invention is used as the host material in OLED devices, it also yields excellent device performance in terms of luminous efficiency, driving voltage, and lifespan. Attached Figure Description

[0020] Figure 1 This is a schematic diagram of a top-emitting device including a nucleation suppression layer provided by the present invention. Detailed Implementation

[0021] 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.

[0022] 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.

[0023] 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".

[0024] The halogen atom mentioned in this invention refers to fluorine, chlorine, bromine, and iodine atoms.

[0025] 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, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl. 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 groups: hydrogen, deuterium, tritium, cyano, halogen, nitro, 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. Preferred substituted silanes specifically include, but are not limited to, trimethylsilane, triethylsilane, triisopropylsilane, tri-tert-butylsilane, tert-butyldimethylsilane, vinyldimethylsilane, propyldimethylsilane, triphenylsilane, diphenylmethylsilane, phenyldimethylsilane, diphenylpyridylsilane, phenyldipyridylsilane, and tripyridylsilane. The aforementioned substituted silanes are preferably trimethylsilane, triethylsilane, triphenylsilane, diphenylmethylsilane, and phenyldimethylsilane.

[0026] The alkyl group described in this invention refers to a hydrocarbon group formed by removing one hydrogen atom from an alkane molecule. It can be a straight-chain alkyl group or a branched-chain alkyl group, preferably having 1 to 15 carbon atoms, more preferably 1 to 12 carbon atoms, and particularly preferably 1 to 6 carbon atoms. The straight-chain alkyl group includes methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, undecyl, dodecyl, etc., but is not limited thereto. The branched-chain alkyl group includes isopropyl, isobutyl, sec-butyl, tert-butyl, isomers of n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, etc., but is not limited thereto. The alkyl group is preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, or tert-butyl.

[0027] 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.

[0028] 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.

[0029] 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.

[0030] 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.

[0031] The heteroaryl group described in this invention refers to the general term for groups obtained by replacing one or more aromatic carbon atoms in an aryl group with heteroatoms. The heteroatoms include, but are not limited to, oxygen, sulfur, nitrogen, silicon, selenium, or phosphorus atoms, preferably having 1 to 25 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 3 to 15 carbon atoms, and most preferably 3 to 12 carbon atoms. The linking site of the heteroaryl group can be located on a cyclic carbon atom or on a cyclic nitrogen atom. The heteroaryl group can be a monocyclic heteroaryl, a polycyclic heteroaryl, or a fused-ring heteroaryl. The monocyclic heteroaryl groups include furanyl, thiophene, pyrrole, imidazole, pyridinyl, pyrimidinyl, etc., but are not limited thereto; the polycyclic heteroaryl groups include phenylfuranyl, phenylthiophene, etc., but are not limited thereto; the fused-ring heteroaryl groups include benzothiophene, benzofuranyl, indolyl, benzoxazolyl, benzoimidazolyl, benzothiazolyl, dibenzofuranyl, benzodibenzofuranyl, dibenzothiophene, benzodibenzothiaphene, carbazolyl, benzocarbazolyl, acridinel, 9,10-dihydroacridinyl, phenoxazinyl, phenthiazinyl, phenoxthiazyl, quinolinyl, isoquinolinyl, quinoxolinyl, quinazolinyl, etc., but are not limited thereto. The aforementioned heteroaryl groups are preferably benzothiophene, benzofuran, indolyl, benzoxazolyl, benzoimidazolyl, benzothiazolyl, dibenzofuran, dibenzothiophene, carbazole, or pyridyl.

[0032] 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 an aliphatic ring and an aromatic ring include benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, etc.

[0033] Benzocyclohexyl, benzocycloheptyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, naphthocyclopropyl, naphthocyclobutyl, naphthocyclopentenyl, naphthocyclohexyl, etc., but not limited to these.

[0034] 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.

[0035] 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.

[0036] 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.

[0037] 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.

[0038] 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.

[0039] 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.

[0040] 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.

[0041] 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:

[0042]

[0043] 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.

[0044] In this specification, "at least one" includes one, two, three, four, five, six, seven, eight or more.

[0045] 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.

[0046] 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.

[0047] This invention provides an anthracene compound having the structure shown in formula (I):

[0048]

[0049] The 'a' is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the 'b' is selected from 0, 1, or 2.

[0050] 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 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] Each time R2 appears, it is selected from one of the following, either the same or different: hydrogen atom, deuterium atom, halogen 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.

[0052] The X is selected from oxygen atoms or sulfur atoms;

[0053] The ring A is selected from one of the following groups substituted or unsubstituted by one or more R3s: an aromatic ring of C6 to C30, a ring formed by the fusion of an aliphatic ring of C3 to C20 and an aromatic ring of C6 to C30, and a heteroaromatic ring of C2 to C30; each time the R3 appears, it is selected from one of the following groups, either the same or different: a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group of C1 to C12, a substituted or unsubstituted cycloalkyl group of C3 to C12, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group 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 substituted or unsubstituted heteroaromatic group of C2 to C30;

[0054] The Ar is selected from one of the following groups substituted with one or more R4s: 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 R4 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 R4 is selected from a substituted or unsubstituted silyl.

[0055] The L1 and L2 are independently selected from single bonds, C6-C30 aryl groups substituted or unsubstituted with one or more R5s, divalent groups formed by the fusion of a C3-C20 aliphatic ring substituted or unsubstituted with one or more R5s and a C6-C30 aromatic ring, C2-C30 heteroaryl groups substituted or unsubstituted with one or more R5s, or combinations thereof; each time the R5 appears, it is selected from the same or different groups of hydrogen atoms, deuterium atoms, halogen atoms, cyano groups, substituted or unsubstituted C1-C12 alkyl groups, substituted or unsubstituted C3-C12 cycloalkyl groups, substituted or unsubstituted silyl groups, substituted or unsubstituted C6-C30 aryl groups, monovalent groups formed by the fusion of a C3-C20 aliphatic ring substituted or unsubstituted with a C6-C30 aromatic ring, and substituted or unsubstituted C2-C30 heteroaryl groups containing nitrogen atoms.

[0056] Preferably, the compound has the structure shown in formula (II) or formula (III):

[0057]

[0058] 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.

[0059] 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 group, ethyl group, isopropyl group, and tert-butyl group, as shown below: cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, 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. The following groups, substituted or unsubstituted, are included: phenyl, naphthyl, anthracene, phenanthrene, triphenylene, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirodifluorenyl, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, N-phenylcarbazoyl, benzocyclopentyl, benzocyclohexyl; trimethylsilyl; triethylsilyl; triisopropylsilyl; tri-tert-butylsilyl; triphenylsilyl; dimethylphenylsilyl; methyldiphenylsilyl; diphenylnaphthylsilyl; phenyldinophylsilyl; trinaphthylsilyl; diphenylpyridylsilyl; phenyldipyridylsilyl; tripyridylsilyl; one or more of these groups. When there are multiple substituents, the multiple substituents may be the same or different.

[0060] 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, norbornyl; and groups substituted by deuterium, fluorine, cyano, methyl, deuterated methyl, trifluoromethyl, ethyl, isopropyl, tert-butyl, cyclopropane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornyl. One of the following: 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, indolyl, dibenzofuranyl, dibenzothiopheneyl, N-phenylcarbazoleyl, benzoxazolyl, benzothiazolyl, and benzimidazoleyl. The above-mentioned substituted or unsubstituted silyl groups; those with deuterium, fluorine, cyano, methyl, deuterated methyl, trifluoromethyl, ethyl, isopropyl, tert-butyl, cyclopropane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornel, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, triphenylsilyl, dimethylphenylsilyl, methyldiphenylsilyl, diphenylnaphthylsilyl, phenyldinophthylsilyl, trinaphthylsilyl, diphenylpyridylsilyl, phenyldipyridylsilyl, tripyridyl One or more of the following groups, substituted or unsubstituted, are contained in the silyl 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.

[0061] Preferably, each time R2 appears, it is selected from hydrogen atoms; deuterium atoms; fluorine atoms; 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, norbornyl; trimethylsilyl; triethylsilyl; triisopropylsilyl; tritert-butylsilyl; triphenylsilyl; dimethylphenylsilyl; methyldiphenylsilyl; diphenylnaphthylsilyl; phenyldinophthylsilyl; trinaphthylsilyl; diphenylpyridylsilyl; phenyldipyridylsilyl; tripyridylsilyl; deuterium atoms; and other groups substituted or unsubstituted by deuterium atoms. The following groups, substituted or unsubstituted, are selected from the following groups: phenyl, naphthyl, anthracene, phenanthrene, trifluoromethyl, ethyl, isopropyl, tert-butyl, cyclopropane, cyclopentane, cyclohexane, cycloheptane, adamantyl, and norbornene: 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-phenylcarbazoleyl, benzoxazolyl, benzothiazolyl, and benzimidazoleyl.

[0062] Preferably, ring A is selected from one of the following groups:

[0063]

[0064]

[0065] In this context, "*" indicates the position where the ring merges with the pentagonal ring.

[0066] Each time a3 appears, it is selected from 0, 1, 2, 3, or 4, either the same or different. Each time b3 appears, it is selected from 0, 1, 2, 3, 4, 5, or 6, either the same or different. Each time c3 appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8, either the same or different. Each time d3 appears, it is selected from 0, 1, 2, 3, 4, or 5, either the same or different. Each time e3 appears, it is selected from 0, 1, or 2, either the same or different. Each time f3 appears, it is selected from 0, 1, 2, or 3, either the same or different. Each time g3 appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10, either the same or different. Each time h3 appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12, either the same or different. Each time i3 appears, it is selected from 0, 1, 2, 3, 4, 5, 6, or 7, either the same or different.

[0067] Y1 is selected from one of oxygen atoms, sulfur atoms, and NR3; Y2 is selected from either oxygen atoms or sulfur atoms.

[0068] Each time R3 appears, it is selected from one of the following, either the same or different: hydrogen atom, deuterium atom, halogen 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.

[0069] Preferably, each time R3 appears, it is selected from hydrogen atoms; deuterium atoms; fluorine atoms; and the following groups substituted or unsubstituted by one or more of deuterium atoms and fluorine atoms: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornyl; substituted by deuterium atoms, fluorine atoms, methyl, deuterated methyl, trifluoromethyl, ethyl, isopropyl, tert-butyl, cyclopropane, 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, benzocyclopentane, benzocyclohexane, benzocycloheptane, pyridinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl The following silyl groups are substituted or unsubstituted with one or more of the following: benzofuranyl, benzothiopheneyl, indolyl, dibenzofuranyl, dibenzothiopheneyl, N-phenylcarbazoyl, benzoxazolyl, benzothiazoyl, and benzimidazolyl; phenyl, naphthyl, anthranilyl, ethyl, isopropyl, tert-butyl, cyclopropane, cyclopentane, cyclohexane, cycloheptane, adamantyl, and norbornel. 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.

[0070] Preferred, Selected from:

[0071]

[0072] Where b1 is selected from 0 or 1; b2 is selected from 0, 1 or 2.

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

[0074]

[0075] Each time a4 appears, it is selected from 0, 1, 2, 3, or 4, either the same or different. Each time b4 appears, it is selected from 0, 1, 2, 3, 4, 5, or 6, either the same or different. Each time c4 appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8, either the same or different. Each time d4 appears, it is selected from 0, 1, 2, or 3, either the same or different. Each time e4 appears, it is selected from 0, 1, or 2, either the same or different. Each time f4 appears, it is selected from 0, 1, 2, 3, 4, 5, 6, or 7, either the same or different. Each time g4 appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10, either the same or different. Each time h4 appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12, either the same or different. Each time i4 appears, it is selected from 0, 1, 2, 3, 4, or 5, either the same or different.

[0076] Z1 is selected from one of oxygen atoms, sulfur atoms, and NR4; Z2 is selected from either oxygen atoms or sulfur atoms.

[0077] Each time R4 appears, it is selected from hydrogen atom, deuterium atom, halogen atom, cyano group, etc. One of the following: substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, a monovalent group formed by the fusion of a substituted or unsubstituted C3-C20 aliphatic ring and a C6-C30 aromatic ring, or substituted or unsubstituted C2-C30 heteroaryl;

[0078] The R mentioned a Each time it appears, it is selected from the same or different groups of 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.

[0079] Preferably, R4, each time it appears, is selected from hydrogen atom; deuterium atom; fluorine atom; cyano group; 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; substituted by deuterium, fluorine, cyano, methyl, deuterated methyl, trifluoromethyl, ethyl, isopropyl, tert-butyl, cyclopropane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornane. alkyl, 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, benzothiopheneyl, indoleyl, di The following silyl groups are substituted or unsubstituted with one or more of the following: benzofuranyl, dibenzothiopheneyl, N-phenylcarbazoleyl, benzoxazolyl, benzothiazolyl, and benzimidazolyl; phenyl, naphthyl, cyano, methyl, deuterated methyl, trifluoromethyl, ethyl, isopropyl, tert-butyl, cyclopropane, cyclopentane, cyclohexane, cycloheptane, adamantyl, and norbornel. One of the following: phenyl, 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.

[0080] Preferably, at most two of R4 are selected from More preferably, at most one of R4 is selected from

[0081] Preferably, the R aEach time it appears, it is selected, either identically or differently, from hydrogen atom; deuterium atom; fluorine atom; cyano group; 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 substituted by one of 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: 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.

[0082] Preferably, the aforementioned Choose one of the following structures:

[0083]

[0084]

[0085] Preferably, L1 and L2 are independently selected from single bonds, groups as shown below, or combinations thereof:

[0086]

[0087] Wherein, each occurrence of a5 is selected from 0, 1, 2, 3, or 4; each occurrence of b5 is selected from 0, 1, 2, or 3; each occurrence of c5 is selected from 0, 1, or 2; each occurrence of d5 is selected from 0, 1, 2, 3, 4, 5, or 6; each occurrence of e5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; each occurrence of f5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; each occurrence of g5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12; and each occurrence of h5 is selected from 0 or 1.

[0088] E1 is selected from one of oxygen atom, sulfur atom, and NR5; E2 is selected from oxygen atom or sulfur atom.

[0089] Each time R5 appears, it is selected from 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 a substituted or unsubstituted C2-C30 heteroaryl group containing a nitrogen atom.

[0090] Preferably, each time R5 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, norbornene; and groups substituted by deuterium, fluorine, cyano, methyl, deuterated methyl, trifluoromethyl, ethyl, isopropyl alkyl, tert-butyl, cyclopropane, cyclopentane, cyclohexane, cycloheptane, adamantane, 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, benzocyclopentane, benzocyclohexane, benzocycloheptane, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolinyl, A silyl group substituted or unsubstituted with one or more of the following: isoquinolinyl, quinoxolinyl, quinazolinyl, benzofuranyl, benzothiophenyl, indolyl, dibenzofuranyl, dibenzothiophenyl, N-phenylcarbazoleyl, benzoxazolyl, benzothiazolyl, and benzimidazolyl; substituted with one or more of the following: deuterium, fluorine, cyano, methyl, deuterated methyl, trifluoromethyl, ethyl, isopropyl, tert-butyl, cyclopropane, cyclopentane, cyclohexane, cycloheptane, adamantyl, and norbornel. The following groups, substituted or unsubstituted, may be used: 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, indolyl, N-phenylcarbazoyl, benzoxoxazolyl, benzothiazoyl, and benzimidazolyl.

[0091] Preferably, the anthracene compound is selected from one of the following compounds:

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110] 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.

[0111] The anthracene compounds represented by formula (I) of this invention can be prepared by the following synthetic route:

[0112]

[0113] Wherein, X1 and X2 are independently selected from chlorine atoms, bromine atoms, or iodine atoms, and X1 ’ X2 ’ Independently selected from B(OH)2 or The rings A, X, R1, R2, Ar, L1, L2, a, and b are as described in this invention.

[0114] In the above synthetic route, the anthracene compound shown in formula (I) is obtained by reacting the halogenated compound (IA) with the borate compound or borate ester compound (IB) or (IC) via a CC coupling reaction. The halogenated compound (IA) can react with the borate compound or borate ester compound (IB) or (IC) in one or two steps to obtain the target compound. There is no particular limitation on the order of reaction between the halogenated compound (IA) and the borate compound or borate ester compound (IB) or (IC). The halogenated compound (IA) can react with the borate compound or borate ester compound (IB) or (IC) simultaneously; or it can react with one of them first, and then with the remaining one.

[0115] 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.

[0116] The present invention also provides an organic electroluminescent device, comprising a first electrode, a second electrode, an organic layer, and a nucleation inhibition layer. The organic layer is located between the first electrode and the second electrode, and the nucleation inhibition layer is located on the side of the second electrode opposite to the first electrode. The nucleation inhibition layer contains one or more anthracene compounds as described in the present invention. Preferably, the second electrode has a first portion and a second portion, with the nucleation inhibition layer disposed on the first portion of the second electrode and a conductive coating disposed on the second portion of the second electrode.

[0117] 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 coating is deposited.

[0118] Therefore, 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 electroluminescent organic light-emitting device. Preferably, the ratio of the first portion to the second portion is 5:95 to 95:5; preferably, the ratio of the first portion to the second portion is 10:90 to 90:10; preferably, the ratio of the first portion to the second portion is 20:80 to 80:20; most preferably, the ratio of the first portion to the second portion is 30:70 to 70:30.

[0119] The present invention also provides an organic electroluminescent device, comprising a first electrode, a second electrode, an organic layer, and a nucleation inhibition layer, wherein the organic layer is located between the first electrode and the second electrode, and the nucleation inhibition layer is located 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.

[0120] 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.

[0121] 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 in 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.

[0122] The conductive coating described in this invention is located in 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.

[0123] The organic electroluminescent device described in this invention can be a top-emitting device, a bottom-emitting device, or a double-sided emitting device.

[0124] 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.

[0125] Preferably, the organic electroluminescent device of the present invention is a top-emitting device, comprising an anode, an organic layer disposed on the anode, and a cathode disposed on the organic layer. The cathode has a first part and a second part. A nucleation inhibition layer is disposed on the first part of the cathode, and a conductive coating is disposed on the second part of the cathode. The nucleation inhibition layer contains one or more of the anthracene compounds described in the present invention.

[0126] 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.

[0127] 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 first electrode (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.

[0128] 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.

[0129]

[0130]

[0131] 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.

[0132] 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.

[0133] 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.

[0134] 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 second electrode (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 second electrode (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.

[0135] 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.

[0136] 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.

[0137] 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 2A value of / Vs or higher facilitates electron transport. One or more of the following substances can be selected: aluminum complexes, lithium complexes, beryllium complexes, oxazole derivatives, benzoxazole derivatives, thiazole derivatives, benzothiazole derivatives, imidazole derivatives, benzimidazole derivatives, phenanthroline derivatives, and polymers. Examples include 1,3,5-tris(1-phenyl-1H-benzimidazol-2-yl)benzene (TPBI) and BAlq, but these are not limited to these.

[0138] 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.

[0139] 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.

[0140] The capping 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 capping layer material can be an organic or inorganic substance with an appropriate refractive index, such as metal halides, oxides, nitrides, nitrogen oxides, sulfides, selenides, aromatic compounds, heteroaromatic compounds, aromatic amine compounds, etc. Examples include LiF, CsF, MgF2, CaF2, CsCl, CuI, V2O5, WO3, MoO3, TiO2, ZrO, ZnO, SiO2, SiN, ZnS, Alq3, compound CP-1, compound CP-2, compound CP-3, and compound CP-4, but are not limited thereto.

[0141]

[0142] The nucleation inhibition layer, conductive coating, cathode, anode, and each organic layer can be prepared using any one of the following methods: vacuum evaporation, inkjet printing, sputtering, plasma deposition, ion plating, spin coating, impregnation, or screen printing. There are no special limitations on the thickness of each layer, as long as good device performance is achieved. Preferably, each organic layer is prepared using vacuum evaporation, inkjet printing, or spin coating.

[0143] 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.

[0144] 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.

[0145] 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.

[0146] 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.

[0147] 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.

[0148] The technical solutions and effects of the present invention will be further described below with reference to embodiments and comparative examples.

[0149] 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.

[0150] 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.

[0151] Synthesis Example 1: Synthesis of Intermediate aa

[0152] Synthesis of intermediate aa-305:

[0153]

[0154] Under nitrogen protection, cc-305 (16.20 g, 100 mmol), dd-305 (26.76 g, 100 mmol), Pd(PPh3)4 (0.46 g, 0.4 mmol), potassium carbonate (29.02 g, 210 mmol) aqueous solution, and DMF (650 mL) were added to the reaction flask, and the mixture was refluxed for 8 hours. After the reaction was completed, 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 aa-305 (23.47 g, 77%); HPLC purity ≥99.80%. Mass spectrometry m / z: 304.0673 (theoretical value: 304.0655).

[0155] By substituting the raw materials according to the synthesis steps of intermediate aa-305, the intermediates shown in Table 1a can be obtained:

[0156] Table 1a

[0157]

[0158] Synthesis Example 2: Synthesis of intermediate BB / DD

[0159] Synthesis of intermediate DD-24:

[0160]

[0161] Under nitrogen protection, aa-24 (16.47 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-24 (11.48 g, 78% yield). HPLC analysis showed a solid purity ≥99.77%. Mass spectrometry m / z: 294.1260 (theoretical value: 294.1247).

[0162] Following the synthesis steps of intermediate DD-24, by substituting the raw materials accordingly, the intermediates shown in Table 1b can be obtained:

[0163] Table 1b

[0164]

[0165]

[0166]

[0167] Synthesis Example 3: Synthesis of Compound 24

[0168]

[0169] Under nitrogen protection, DMF (500 ml), AA-24 (14.58 g, 50 mmol), BB-24 (8.10 g, 50 mmol), Pd2(dba)3 (0.46 g, 0.5 mmol), sodium tert-butoxide (9.61 g, 100 mmol), and BINAP (0.62 g, 1 mmol) were added sequentially to a reaction flask. The mixture was stirred and heated under reflux for 6 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-24 (19.81 g, 73% yield). HPLC analysis showed a solid purity ≥99.78%. Mass spectrometry m / z: 328.0675 (theoretical value: 328.0655).

[0170] Under nitrogen protection, CC-24 (3.29 g, 10 mmol), DD-24 (2.94 g, 10 mmol), Pd(PPh3)4 (0.05 g, 0.04 mmol), potassium carbonate (2.90 g, 21 mmol) aqueous solution, and DMF (65 mL) were added to the reaction flask, and the mixture was refluxed for 7 hours. After the reaction was completed, 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 24 (3.80 g, 70%); HPLC purity ≥99.95%. Mass spectrometry m / z: 542.2077 (theoretical value: 542.2066). Theoretical elemental content (%) C 39 H 30 OSi: C, 86.31; H, 5.57. Measured elemental content (%): C, 86.38; H, 5.52.

[0171] Synthesis Example 4: Synthesis of Compound 122

[0172]

[0173] By replacing BB-24 with an equimolar amount of cc-305 and DD-24 with an equimolar amount of DD-122, and following the same steps as in Synthesis Example 3, compound 122 (3.62 g, yield 68%) was obtained. HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 532.1839 (theoretical value: 532.1859). Theoretical elemental content (%) C37 H 28 O2Si: C, 83.42; H, 5.30. Measured elemental content (%): C, 83.46; H, 5.25.

[0174] Synthesis Example 5: Synthesis of Compound 158

[0175]

[0176] By replacing BB-24 with an equimolar amount of BB-158 and DD-24 with an equimolar amount of DD-158, and following the same steps as in Synthesis Example 3, compound 158 (3.60 g, 70% yield) was obtained. HPLC analysis showed a solid purity ≥ 99.92%. Mass spectrometry m / z: 514.2162 (theoretical value: 514.2148). Theoretical elemental content (%) C 34 H 34 OSi2: C, 79.32; H, 6.66. Measured elemental content (%): C, 79.30; H, 6.70.

[0177] Synthesis Example 6: Synthesis of Compound 174

[0178]

[0179] By replacing BB-24 with an equimolar amount of cc-305 and DD-24 with an equimolar amount of DD-174, and following the same steps as in Synthesis Example 3, compound 174 (4.46 g, yield 71%) was obtained. HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 628.2238 (theoretical value: 628.2222). Theoretical elemental content (%) C 46 H 32 OSi: C, 87.86; H, 5.13. Measured elemental content (%): C, 87.83; H, 5.18.

[0180] Synthesis Example 7: Synthesis of Compound 231

[0181]

[0182] By replacing BB-24 with an equimolar amount of BB-231 and DD-24 with an equimolar amount of DD-231, and following the same steps as in Synthesis Example 3, compound 231 (3.73 g, yield 72%) was obtained. HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 518.2079 (theoretical value: 518.2066). Theoretical elemental content (%) C 37 H 30OSi: C, 85.67; H, 5.83. Measured elemental content (%): C, 85.63; H, 5.89.

[0183] Synthesis Example 8: Synthesis of Compound 236

[0184]

[0185] By replacing BB-24 with an equimolar amount of BB-236 and DD-24 with an equimolar amount of DD-231, and following the same steps as in Synthesis Example 3, compound 236 (3.94 g, yield 76%) was obtained. HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 518.2085 (theoretical value: 518.2066). Theoretical elemental content (%) C 37 H 30 OSi: C, 85.67; H, 5.83. Measured elemental content (%): C, 85.62; H, 5.89.

[0186] Synthesis Example 9: Synthesis of Compound 292

[0187]

[0188] By replacing BB-24 with an equimolar amount of BB-236 and DD-24 with an equimolar amount of DD-158, and following the same steps as in Synthesis Example 3, compound 292 (4.37 g, yield 74%) was obtained. HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 590.2475 (theoretical value: 590.2461). Theoretical elemental content (%) C 40 H 38 OSi2: C, 81.30; H, 6.48. Measured elemental content (%): C, 81.33; H, 6.42.

[0189] Synthesis Example 10: Synthesis of Compound 305

[0190]

[0191] By replacing BB-24 with an equimolar amount of BB-305 and DD-24 with an equimolar amount of DD-231, and following the same steps as in Synthesis Example 3, compound 305 (4.34 g, yield 73%) was obtained. HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 594.2365 (theoretical value: 594.2379). Theoretical elemental content (%) C 43 H 34 OSi: C, 86.83; H, 5.76. Measured elemental content (%): C, 86.85; H, 5.72.

[0192] Synthesis Example 11: Synthesis of Compound 324

[0193]

[0194] By replacing BB-24 with an equimolar amount of BB-324 and DD-24 with an equimolar amount of DD-231, and following the same steps as in Synthesis Example 3, compound 324 (4.21 g, yield 74%) was obtained. HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 568.2236 (theoretical value: 568.2222). Theoretical elemental content (%) C 41 H 32 OSi: C, 86.58; H, 5.67. Measured elemental content (%): C, 86.56; H, 5.69.

[0195] Synthesis Example 12: Synthesis of Compound 336

[0196]

[0197] By replacing BB-24 with an equimolar amount of BB-336 and DD-24 with an equimolar amount of DD-231, and following the same steps as in Synthesis Example 3, compound 336 (6.97 g, yield 71%) was obtained. HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 558.2365 (theoretical value: 558.2379). Theoretical elemental content (%) C 40 H 34 OSi: C, 85.98; H, 6.13. Measured elemental content (%): C, 85.95; H, 6.19.

[0198] Synthesis Example 13: Synthesis of Compound 356

[0199]

[0200] By replacing BB-24 with an equimolar amount of BB-356 and DD-24 with an equimolar amount of DD-231, and following the same steps as in Synthesis Example 3, compound 356 (4.19 g, yield 66%) was obtained. HPLC analysis showed a solid purity ≥ 99.92%. Mass spectrometry m / z: 634.2680 (theoretical value: 634.2692). Theoretical elemental content (%) C 46 H 38 OSi: C, 87.02; H, 6.03. Measured elemental content (%): C, 87.05; H, 6.08.

[0201] Synthesis Example 14: Synthesis of Compound 362

[0202]

[0203] By replacing BB-24 with an equimolar amount of BB-362 and DD-24 with an equimolar amount of DD-231, and following the same steps as in Synthesis Example 3, compound 362 (3.48 g, yield 67%) was obtained. HPLC analysis showed a solid purity ≥ 99.90%. Mass spectrometry m / z: 519.2005 (theoretical value: 519.2018). Theoretical elemental content (%) C 36 H 29 NOSi: C, 83.20; H, 5.62; N, 2.70. Measured elemental content (%): C, 83.22; H, 5.66; N, 2.65.

[0204] Synthesis Example 15: Synthesis of Compound 369

[0205]

[0206] By replacing BB-24 with an equimolar amount of BB-369 and DD-24 with an equimolar amount of DD-231, and following the same steps as in Synthesis Example 3, compound 369 (4.20 g, yield 69%) was obtained. HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 608.2156 (theoretical value: 608.2172). Theoretical elemental content (%) C 43 H 32 O2Si: C, 84.83; H, 5.30. Measured elemental content (%): C, 84.86; H, 5.26.

[0207] Synthesis Example 16: Synthesis of Compound 371

[0208]

[0209] By replacing BB-24 with an equimolar amount of BB-231 and DD-24 with an equimolar amount of DD-174, and following the same steps as in Synthesis Example 3, compound 371 (4.93 g, 70% yield) was obtained. HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 704.2550 (theoretical value: 704.2535). Theoretical elemental content (%) C 52 H 36 OSi: C, 88.60; H, 5.15. Measured elemental content (%): C, 88.66; H, 5.11.

[0210] Synthesis Example 17: Synthesis of Compound 397

[0211]

[0212] By replacing BB-24 with an equimolar amount of cc-305 and DD-24 with an equimolar amount of DD-397, and following the same steps as in Synthesis Example 3, compound 397 (3.84 g, yield 74%) was obtained. HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 518.2079 (theoretical value: 518.2066). Theoretical elemental content (%) C 37 H 30 OSi: C, 85.67; H, 5.83. Measured elemental content (%): C, 85.69; H, 5.80.

[0213] Synthesis Example 18: Synthesis of Compound 405

[0214]

[0215] Replacing DD-24 with an equimolar amount of DD-405, and following the same steps as in Synthesis Example 3, yielded compound 405 (3.82 g, yield 73%). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 522.2329 (theoretical value: 522.2317). Theoretical elemental content (%) C 37 H 26 D4OSi: C, 85.01; H, 6.55. Measured elemental content (%): C, 85.05; H, 6.52.

[0216] Synthesis Example 19: Synthesis of Compound 430

[0217]

[0218] By replacing BB-24 with an equimolar amount of BB-430 and DD-24 with an equimolar amount of DD-430, and following the same steps as in Synthesis Example 3, compound 430 (4.46 g, yield 75%) was obtained. HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 594.2388 (theoretical value: 594.2379). Theoretical elemental content (%) C 43 H 34 OSi: C, 86.83; H, 5.76. Measured elemental content (%): C, 86.88; H, 5.74.

[0219] Synthesis Example 20: Synthesis of Compound 456

[0220]

[0221] By replacing BB-24 with an equimolar amount of BB-236 and DD-24 with an equimolar amount of DD-397, and following the same steps as in Synthesis Example 3, compound 456 (4.40 g, yield 74%) was obtained. HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 594.2362 (theoretical value: 594.2379). Theoretical elemental content (%) C 43 H 34 OSi: C, 86.83; H, 5.76. Measured elemental content (%): C, 86.80; H, 5.78.

[0222] Synthesis Example 21: Synthesis of Compound 505

[0223]

[0224] By replacing BB-24 with an equimolar amount of BB-505 and DD-24 with an equimolar amount of DD-231, and following the same steps as in Synthesis Example 3, compound 505 (3.73 g, yield 72%) was obtained. HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 518.2054 (theoretical value: 518.2066). Theoretical elemental content (%) C 37 H 30 OSi: C, 85.67; H, 5.83. Measured elemental content (%): C, 85.62; H, 5.87.

[0225] Synthesis Example 22: Synthesis of Compound 530

[0226]

[0227] Replacing BB-24 with an equimolar amount of BB-530 and DD-24 with an equimolar amount of DD-530, while following the same steps as in Synthesis Example 3, yielded compound 530 (3.51 g, 70% yield). HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 500.1976 (theoretical value: 500.1994). Theoretical elemental content (%) C 34 H 32 SSi: C, 81.55; H, 6.44. Measured elemental content (%): C, 81.53; H, 6.49.

[0228] Synthesis Example 23: Synthesis of Compound 571

[0229]

[0230] By replacing BB-24 with an equimolar amount of BB-571 and DD-24 with an equimolar amount of DD-231, and following the same steps as in Synthesis Example 3, compound 571 (4.06 g, yield 76%) was obtained. HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 534.1854 (theoretical value: 534.1837). Theoretical elemental content (%) C 37 H 30 SSi: C, 83.10; H, 5.65. Measured elemental content (%): C, 83.15; H, 5.62.

[0231] Synthesis Example 24: Synthesis of Compound 575

[0232]

[0233] By replacing BB-24 with an equimolar amount of BB-575 and DD-24 with an equimolar amount of DD-575, and following the same steps as in Synthesis Example 3, compound 575 (4.33 g, yield 74%) was obtained. HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 584.1975 (theoretical value: 584.1994). Theoretical elemental content (%) C 41 H 32 SSi: C, 84.20; H, 5.52. Measured elemental content (%): C, 84.28; H, 5.47.

[0234] Synthesis Example 25: Synthesis of Compound 579

[0235]

[0236] By replacing BB-24 with an equimolar amount of BB-575 and DD-24 with an equimolar amount of DD-579, and following the same steps as in Synthesis Example 3, compound 579 (3.80 g, yield 71%) was obtained. HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 535.1775 (theoretical value: 535.1790). Theoretical elemental content (%) C 36 H 29 NSSi: C, 80.70; H, 5.46; N, 2.61. Measured elemental content (%): C, 80.72; H, 5.43; N, 2.66.

[0237] Synthesis Example 26: Synthesis of Compound 612

[0238]

[0239] By replacing BB-24 with an equimolar amount of BB-612 and DD-24 with an equimolar amount of DD-397, and following the same steps as in Synthesis Example 3, compound 612 (4.28 g, 70% yield) was obtained. HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 610.2168 (theoretical value: 610.2150). Theoretical elemental content (%) C 43 H 34 SSi: C, 84.54; H, 5.61. Measured elemental content (%): C, 84.56; H, 5.57.

[0240] Synthesis Example 27: Synthesis of Compound 632

[0241]

[0242] Under nitrogen protection, AA-632 (3.36 g, 10 mmol), BB-632 (5.00 g, 20 mmol), Pd(PPh3)4 (0.10 g, 0.08 mmol), potassium carbonate (5.80 g, 42 mmol) aqueous solution, and DMF (130 mL) were added to the reaction flask, and the mixture was refluxed for 7 hours. After the reaction was completed, 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 632 (4.40 g, 75%); HPLC purity ≥99.94%. Mass spectrometry m / z: 586.1657 (theoretical value: 586.1640). Theoretical elemental content (%) C 36 H 34 S2Si2: C, 73.67; H, 5.84. Measured elemental content (%): C, 73.69; H, 5.80.

[0243] Synthesis Example 28: Synthesis of Compound 646

[0244]

[0245] By replacing BB-24 with an equimolar amount of BB-646 and DD-24 with an equimolar amount of DD-397, and following the same steps as in Synthesis Example 3, compound 646 (4.21 g, yield 74%) was obtained. HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 568.2240 (theoretical value: 568.2222). Theoretical elemental content (%) C 41 H 32 OSi: C, 86.58; H, 5.67. Measured elemental content (%): C, 86.57; H, 5.69.

[0246] Synthesis Example 29: Synthesis of Compound 647

[0247]

[0248] By replacing BB-24 with an equimolar amount of BB-647 and DD-24 with an equimolar amount of DD-231, and following the same steps as in Synthesis Example 3, compound 647 (3.70 g, yield 69%) was obtained. HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 535.1775 (theoretical value: 535.1790). Theoretical elemental content (%) C 36 H 29 NSSi: C, 80.70; H, 5.46; N, 2.61. Measured elemental content (%): C, 80.78; H, 5.41; N, 2.60.

[0249] Synthesis Example 30: Synthesis of Compound 710

[0250]

[0251] Under nitrogen protection, DMF (500 ml), AA-710 (20.87 g, 50 mmol), BB-710 (6.10 g, 50 mmol), Pd2(dba)3 (0.46 g, 0.5 mmol), sodium tert-butoxide (9.61 g, 100 mmol), and BINAP (0.62 g, 1 mmol) were added sequentially to a reaction flask. The mixture was stirred and heated under reflux for 6 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-710 (12.68 g, 69% yield). HPLC analysis showed a solid purity ≥ 99.69%. Mass spectrometry m / z: 365.9819 (theoretical value: 365.9811).

[0252] Under nitrogen protection, CC-710 (11.03 g, 30 mmol), BB-236 (7.14 g, 30 mmol), Pd(PPh3)4 (0.14 g, 0.12 mmol), potassium carbonate (8.71 g, 63 mmol) aqueous solution, and DMF (200 mL) were added to the reaction flask, and the mixture was refluxed for 7 hours. After the reaction was completed, 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-710 (10.39 g, 72%); HPLC purity ≥99.81%. Mass spectrometry m / z: 480.1297 (theoretical value: 480.1281).

[0253] Under nitrogen protection, EE-710 (4.81 g, 10 mmol), DD-231 (1.94 g, 10 mmol), potassium carbonate (2.07 g, 15 mmol), and Pd2(dba)3 (0.09 g, 0.1 mmol) were added to a reaction flask, followed by 100 mL of a toluene / ethanol / water (2:1:1) mixture. The mixture was stirred and refluxed for 6 hours. After the reaction was complete, the mixture was cooled to room temperature, filtered, and the resulting solid was recrystallized from toluene to give compound 710 (4.04 g, yield 68%). HPLC analysis showed the solid purity to be ≥99.93%. Mass spectrometry m / z: 594.2363 (theoretical value: 594.2379). Theoretical elemental content (%) C 43 H 34 OSi: C, 86.83; H, 5.76. Measured elemental content (%): C, 86.86; H, 5.72.

[0254] Synthesis Example 31: Synthesis of Compound 725

[0255]

[0256] Under nitrogen protection, AA-725 (18.52 g, 50 mmol), CC-305 (16.20 g, 100 mmol), Pd(PPh3)4 (0.46 g, 0.4 mmol), potassium carbonate (29.02 g, 210 mmol) aqueous solution, and DMF (650 mL) were added to the reaction flask, and the mixture was refluxed for 7 hours. After the reaction was completed, 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 CC-725 (16.24 g, 73%); HPLC purity ≥99.77%. Mass spectrometry m / z: 444.0927 (theoretical value: 444.0917).

[0257] Under nitrogen protection, CC-725 (4.45 g, 10 mmol), DD-231 (1.94 g, 10 mmol), potassium carbonate (2.07 g, 15 mmol), and Pd2(dba)3 (0.09 g, 0.1 mmol) were added to a reaction flask, followed by 100 mL of a toluene / ethanol / water (2:1:1) mixture. The mixture was stirred and refluxed for 6 hours. After the reaction was complete, the mixture was cooled to room temperature, filtered, and the resulting solid was recrystallized from toluene to give compound 725 (3.97 g, yield 71%). HPLC analysis showed the solid purity to be ≥99.96%. Mass spectrometry m / z: 558.2006 (theoretical value: 558.2015). Theoretical elemental content (%) C 39 H 30O2Si: C, 83.83; H, 5.41. Measured elemental content (%): C, 83.81; H, 5.46.

[0258] Synthesis Example 32: Synthesis of Compound 789

[0259]

[0260] Under nitrogen protection, AA-789 (20.25 g, 50 mmol), DD-231 (19.41 g, 100 mmol), Pd(PPh3)4 (0.46 g, 0.4 mmol), potassium carbonate (29.02 g, 210 mmol) aqueous solution, and DMF (650 mL) were added to the reaction flask, and the mixture was refluxed for 7 hours. After the reaction was completed, 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 CC-789 (19.03 g, 70%); HPLC purity ≥99.73%. Mass spectrometry m / z: 542.1436 (theoretical value: 542.1420).

[0261] Under nitrogen protection, CC-789 (5.44 g, 10 mmol), BB-530 (3.56 g, 20 mmol), potassium carbonate (4.15 g, 30 mmol), and Pd2(dba)3 (0.18 g, 0.2 mmol) were added to a reaction flask, followed by 150 mL of a toluene / ethanol / water (2:1:1) mixture. The mixture was stirred and refluxed for 6 hours. After the reaction was complete, the mixture was cooled to room temperature, filtered, and the resulting solid was recrystallized from toluene to give compound 789 (4.95 g, yield 67%). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 738.2277 (theoretical value: 738.2266). Theoretical elemental content (%) C 48 H 42 S2Si2: C, 78.00; H, 5.73. Measured elemental content (%): C, 78.05; H, 5.70.

[0262] Device Examples

[0263] Nucleation inhibition materials

[0264] Testing instrument: UV-Vis spectrophotometer (manufacturer: Shanghai Xipu Instrument Co., Ltd., model: UV-2202PC)

[0265] Comparative Example 1: Comparative Sample 1

[0266] 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).

[0267] Comparative Examples 2-3: Comparative Samples 2-3

[0268] By replacing the control compound Ref-1 in Comparative Example 1 with control compounds Ref-2 and Ref-3 respectively, control samples 2 and 3 can be obtained.

[0269]

[0270] Examples 1-30: Samples 1-30

[0271] By replacing the comparative compound Ref-1 in Comparative Example 1 with the anthracene compounds of the present invention synthesized in Synthetic Examples 3 to 32, samples 1 to 30 can be obtained.

[0272] The optical transmittance test results of the samples prepared in Comparative Examples 1-3 and Examples 1-30 are shown in Table 2.

[0273] Table 2 Optical transmittance test data

[0274]

[0275]

[0276] As shown in Table 2, compared to Comparative Examples 1-3, the anthracene compounds of the present invention, when used as nucleation inhibition layers, exhibit higher optical transmittance in their deposited magnesium coatings, indicating the presence of a relatively small amount of magnesium coating on their surfaces. Therefore, the anthracene compounds of the present invention can effectively inhibit magnesium deposition on their surfaces, making them excellent nucleation inhibition materials.

[0277] Main materials

[0278] The following are compounds other than the anthracene compounds described in this invention used in the device fabrication examples:

[0279]

[0280] 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.

[0281] Comparative device fabrication example 1: Comparative device 1

[0282] 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.

[0283] The following layers were deposited layer by layer on the aforementioned ITO / Ag / ITO glass substrate: a) HT-10 and p-1 (mass ratio 100:1) as hole injection layer with a thickness of 10 nm; b) HT-1 as hole transport layer with a thickness of 120 nm; c) BH-1 and BD (mass ratio 95:5) as light-emitting layer with a thickness of 20 nm; d) TPBi as hole blocking layer with a thickness of 5 nm; e) BCP and Liq (mass ratio 5:5) as electron transport layer with a thickness of 30 nm; f) LiF as electron injection layer with a thickness of 1 nm; g) Mg and Ag (mass ratio 1:9) as cathode with a thickness of 13 nm; h) CP-4 as capping layer with a thickness of 70 nm.

[0284] Comparative device fabrication examples 2-3: Comparative devices 2-3

[0285] By replacing BH-1 in the luminescent layer with compounds BH-2 and BH-3 respectively, comparative devices 2 and 3 can be obtained.

[0286] Device fabrication examples 1-30: Light-emitting devices 1-30

[0287] By replacing BH-1 in the light-emitting layer with the anthracene compounds of the present invention synthesized in Examples 3 to 32, light-emitting devices 1 to 30 can be obtained.

[0288] Table 3

[0289]

[0290]

[0291] The device data in Table 3 show that the anthracene compounds provided by this invention, as the host material of the light-emitting layer, improve the driving voltage, luminous efficiency and lifespan of the device, making them a very good host material.

[0292] In summary, the anthracene compounds provided by this invention are a class of high-performance OLED materials.

[0293] 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 having the structure shown in formula (I): The 'a' is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the 'b' is selected from 0, 1, or 2. 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 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. Each time R2 appears, it is selected from one of the following, either the same or different: hydrogen atom, deuterium atom, halogen 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. The X is selected from oxygen atoms or sulfur atoms; The ring A is selected from one of the following groups substituted or unsubstituted by one or more R3s: an aromatic ring of C6 to C30, a ring formed by the fusion of an aliphatic ring of C3 to C20 and an aromatic ring of C6 to C30, and a heteroaromatic ring of C2 to C30; each time the R3 appears, it is selected from one of the following groups, either the same or different: a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group of C1 to C12, a substituted or unsubstituted cycloalkyl group of C3 to C12, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group 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 substituted or unsubstituted heteroaromatic group of C2 to C30; The Ar is selected from one of the following groups substituted with one or more R4s: 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 R4 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 R4 is selected from a substituted or unsubstituted silyl. The L1 and L2 are independently selected from single bonds, C6-C30 aryl groups substituted or unsubstituted with one or more R5s, divalent groups formed by the fusion of a C3-C20 aliphatic ring substituted or unsubstituted with one or more R5s and a C6-C30 aromatic ring, C2-C30 heteroaryl groups substituted or unsubstituted with one or more R5s, or combinations thereof; each time the R5 appears, it is selected from the same or different groups of hydrogen atoms, deuterium atoms, halogen atoms, cyano groups, substituted or unsubstituted C1-C12 alkyl groups, substituted or unsubstituted C3-C12 cycloalkyl groups, substituted or unsubstituted silyl groups, substituted or unsubstituted C6-C30 aryl groups, monovalent groups formed by the fusion of a C3-C20 aliphatic ring substituted or unsubstituted with a C6-C30 aromatic ring, and substituted or unsubstituted C2-C30 heteroaryl groups containing nitrogen atoms.

2. The anthracene compound according to claim 1, characterized in that, The ring A is selected from one of the following groups: Among them, "*" indicates the position where it merges with the pentagon; Each time a3 appears, it is selected from 0, 1, 2, 3, or 4, either the same or different. Each time b3 appears, it is selected from 0, 1, 2, 3, 4, 5, or 6, either the same or different. Each time c3 appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8, either the same or different. Each time d3 appears, it is selected from 0, 1, 2, 3, 4, or 5, either the same or different. Each time e3 appears, it is selected from 0, 1, or 2, either the same or different. Each time f3 appears, it is selected from 0, 1, 2, or 3, either the same or different. Each time g3 appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10, either the same or different. Each time h3 appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12, either the same or different. Each time i3 appears, it is selected from 0, 1, 2, 3, 4, 5, 6, or 7, either the same or different. Y1 is selected from one of oxygen atoms, sulfur atoms, and NR3; Y2 is selected from either oxygen atoms or sulfur atoms. Each time R3 appears, it is selected from one of the following, either the same or different: hydrogen atom, deuterium atom, halogen 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.

3. The anthracene compound according to claim 1, characterized in that, The Ar group is selected from one of the following groups: Each time a4 appears, it is selected from 0, 1, 2, 3, or 4, either the same or different. Each time b4 appears, it is selected from 0, 1, 2, 3, 4, 5, or 6, either the same or different. Each time c4 appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8, either the same or different. Each time d4 appears, it is selected from 0, 1, 2, or 3, either the same or different. Each time e4 appears, it is selected from 0, 1, or 2, either the same or different. Each time f4 appears, it is selected from 0, 1, 2, 3, 4, 5, 6, or 7, either the same or different. Each time g4 appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10, either the same or different. Each time h4 appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12, either the same or different. Each time i4 appears, it is selected from 0, 1, 2, 3, 4, or 5, either the same or different. Z1 is selected from one of oxygen atoms, sulfur atoms, and NR4; Z2 is selected from either oxygen atoms or sulfur atoms. Each time R4 appears, it is selected from hydrogen atom, deuterium atom, halogen atom, cyano group, etc. One of the following: substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, a monovalent group formed by the 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 a Each time it appears, it is selected from the same or different groups of 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.

4. The anthracene compound according to claim 3, characterized in that, The R mentioned a Each time it appears, it is selected, either identically or differently, from hydrogen atom; deuterium atom; fluorine atom; cyano group; 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 substituted by one of 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: 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.

5. The anthracene compound according to claim 3, characterized in that, The aforementioned Choose one of the following structures:

6. 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 a5 is selected from 0, 1, 2, 3, or 4; each occurrence of b5 is selected from 0, 1, 2, or 3; each occurrence of c5 is selected from 0, 1, or 2; each occurrence of d5 is selected from 0, 1, 2, 3, 4, 5, or 6; each occurrence of e5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; each occurrence of f5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; each occurrence of g5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12; and each occurrence of h5 is selected from 0 or 1. E1 is selected from one of oxygen atom, sulfur atom, and NR5; E2 is selected from oxygen atom or sulfur atom. Each time R5 appears, it is selected from 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 a substituted or unsubstituted C2-C30 heteroaryl group containing a nitrogen atom.

7. The anthracene compound according to claim 1, characterized in that, The anthracene compounds are selected from one of the following compounds:

8. An organic electroluminescent device, comprising a first electrode, a second electrode, an organic layer, and a nucleation inhibition layer, wherein the organic layer is located between the first electrode and the second electrode, and the nucleation inhibition layer is located on the side of the second electrode opposite to the first electrode, characterized in that, The nucleation inhibition layer contains one or more of the anthracene compounds described in any one of claims 1 to 7.

9. An organic electroluminescent device, comprising a first electrode, a second electrode, an organic layer, and a nucleation inhibition layer, wherein the organic layer is located between the first electrode and the second electrode, and the nucleation inhibition layer is located 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 7.

10. 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 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, characterized in that, The light-emitting layer contains one or more of the anthracene compounds as described in any one of claims 1 to 7.

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