A compound containing a fluorene group and an organic electroluminescent device thereof

Abstract

The application provides a compound containing a fluorene group and an organic electroluminescent device thereof. The compound of the application contains at least one or more deuterium atoms in the structure, has higher electron mobility, and can effectively enhance the electron transport capacity of the organic electroluminescent device. The compound of the application can be applied to a light-emitting layer and an electron transport region, can effectively reduce the driving voltage of the organic electroluminescent device, improve the light-emitting efficiency, and can significantly increase the service life of the device, thereby enhancing the durability of the device. It can be widely applied to the field of information display technology, such as mobile phones, tablet computers, televisions, wearable devices, VR, vehicle displays and tail lights, etc.

Description

Technical Field

[0001] This invention relates to the field of organic electroluminescent materials technology, specifically to a compound containing a fluorene group and its organic electroluminescent device. Background Technology

[0002] Organic light-emitting diodes (OLEDs) have attracted widespread attention due to their advantages such as being all-solid-state, actively emitting light, offering rich colors, fast response times, ultra-thin design, and the ability to achieve flexible displays, demonstrating promising application prospects. After years of efforts from industry, academia, and research institutions in material development, structural optimization, and process improvement, OLEDs have made significant progress in both display and lighting applications. As a novel light-emitting technology, OLEDs are currently experiencing rapid development, and their future prospects are very promising.

[0003] OLEDs emit light by sandwiching an organic light-emitting layer between two electrodes and then applying an electric current. Their light-emitting mechanism is generally a dual-carrier injection mode. OLEDs typically consist of an anode, a cathode, and an organic layer. This organic layer can include a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and a capping layer. Furthermore, to balance the electron or hole transport rates and improve OLED device performance, an electron blocking layer is often added between the hole transport layer and the light-emitting layer, or a hole blocking layer is added between the electron transport layer and the light-emitting layer.

[0004] The main limitations of traditional OLED devices are that the carrier mobility of the electron transport layer is low, and electrons cannot be effectively transported to the light-emitting layer; the efficiency of hole and electron transport is low and unbalanced, resulting in a low probability of hole and electron recombination; ultimately, the luminous efficiency of OLED devices is relatively low, the driving voltage is high, and the lifespan is short. According to some requirements of OLED itself, electron transport materials that can be used in OLEDs should have the following characteristics: (1) having suitable LUMO and HOMO energy levels to effectively block holes; (2) having high triplet energy levels to effectively prevent the energy of excitons in the light-emitting layer from being transferred to adjacent layers; (3) having high electron mobility to facilitate electron transport; and (4) having good thermodynamic stability to prevent crystallization during device fabrication and thus improve the lifespan of the device.

[0005] The development of organic electroluminescent devices has promoted the research and development of electron transport materials, but existing electron transport materials can no longer meet market demands. Therefore, in order to further promote the vigorous development of OLEDs, it is urgent to develop high-performance OLED electron transport materials. Summary of the Invention

[0006] To address the aforementioned technical problems, this invention provides a compound containing a fluorene group, which has a high triplet energy level, effectively balances holes and electrons, and also possesses excellent electron transport and hole blocking capabilities, as well as good thermodynamic stability. When used in organic electroluminescent devices, it can effectively improve the device's luminous efficiency, driving voltage, and lifespan.

[0007] Specifically, the present invention provides a compound containing a fluorene group, wherein the compound containing the fluorene group is selected from the structure shown in Chemical Formula 1.

[0008]

[0009] Wherein, Ar1 and Ar2 are independently selected from the following formula a;

[0010] * indicates a connection site;

[0011] The same or different E is selected from C(R3) or N, and the same or different R3 is selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic group, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted silyl, or two adjacent R3 are connected to form a substituted or unsubstituted ring;

[0012] The same or different X is selected from C(Rm) or N, and the same or different Rm is selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic group, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted silyl, or two adjacent Rm are connected to form a substituted or unsubstituted ring;

[0013] The Y is selected from O, S, C(RaRb), and N(Rc). The Ra and Rb, whether the same or different, are selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, and substituted or unsubstituted silyl. The Rc, whether the same or different, is selected from any one of substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, and substituted or unsubstituted silyl.

[0014] R1 and R2 are independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic group, substituted or unsubstituted silyl group, or R1 or R2 are directly bonded to L, or R1 and R2 are combined with each other to form a substituted or unsubstituted C3-C12 aliphatic ring;

[0015] The R0 is selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, and substituted or unsubstituted silyl; or two adjacent R0s are connected to form a substituted or unsubstituted benzene ring or naphthalene ring; the v is selected from 1, 2, or 3;

[0016] Rx is selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, and substituted or unsubstituted silyl; m is selected from 1 or 2;

[0017] The L, L1, and L2 are independently selected from any one of single-bonded, substituted or unsubstituted C6-C30 arylene, or substituted or unsubstituted C2-C30 heteroarylene.

[0018] At least one of R0, R1, R2, R3, Rm, Rx, Ra, Rb, Rc, L, L1, and L2 contains one or more deuterium.

[0019] The present invention also provides an organic electroluminescent device comprising an anode, a cathode, and an organic layer located between the anode and the cathode, the organic layer comprising the compound having the structure of Formula 1.

[0020] Beneficial effects

[0021] The fluorene-containing compounds provided by this invention possess high electron mobility, facilitating electron transport. When applied to electron transport layers / hole blocking layers, they minimize exciton diffusion into adjacent functional layers, thereby improving the luminous efficiency of the device. Simultaneously, the compounds of this invention have a wide bandgap and high triplet energy levels. When used as the host material of the luminescent layer, they can effectively balance holes and electrons, effectively improving the driving voltage and luminous efficiency of organic electroluminescent devices. Furthermore, the compounds of this invention possess high glass transition temperatures. When applied to organic electroluminescent devices, they can form more uniform and heat-resistant thin films, extending the device's lifespan. Detailed Implementation

[0022] The technical solutions of this invention will be clearly and completely described below with reference to specific embodiments. Obviously, the described embodiments are only a part of the embodiments of this invention, and not all of them. Based on the embodiments of this invention, all other embodiments obtained by those skilled in the art without creative effort are within the protection scope of this invention.

[0023] In this specification, "*" indicates a portion connected to another substituent. "*" can be attached to any optional position of the group / fraction to which it is attached.

[0024] 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 And so on.

[0025] 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.

[0026] Examples of halogens described in this invention may include fluorine, chlorine, bromine, and iodine.

[0027] The alkyl group referred to in this invention is a general term for monovalent groups obtained 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 25 carbon atoms, more preferably 1 to 12 carbon atoms, and particularly preferably 1 to 6 carbon atoms. Specific examples may include methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, undecyl, dodecyl, isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, etc., but are not limited thereto.

[0028] The alicyclic group mentioned in this invention refers to the general term for monovalent groups obtained by removing one hydrogen atom from an alicyclic hydrocarbon molecule. These groups can be cycloalkyl, cycloalkenyl, etc., preferably having 3 to 25 carbon atoms, more preferably 3 to 20 carbon atoms, particularly preferably 3 to 15 carbon atoms, more preferably 5 to 10 carbon atoms, and most preferably 5 to 7 carbon atoms. Specific examples may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, etc., but are not limited thereto.

[0029] The “substituted or unsubstituted silyl group” as described in this invention refers to the -Si(R)3 group, wherein each R is the same or different and is selected from the following groups: 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, whether identical or different, is selected from the following groups: 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. Preferably, each R, whether identical or different, is selected from the following groups: hydrogen, deuterium, tritium, cyano, halogen, nitro, or substituted or unsubstituted of the following groups: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, camphenyl, phenyl, biphenyl, naphthyl. Examples may include, but are not limited to, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, dimethylethylsilyl, dimethylisopropylsilyl, dimethyltert-butylsilyl, tricyclopentylsilyl, tricyclohexylsilyl, triphenylsilyl, triphenylsilyl, tripyridylsilyl, tripyridylsilyl, etc.

[0030] The aryl group mentioned in this invention refers to the general term for the monovalent group obtained by 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 30 carbon atoms, more preferably 6 to 18 carbon atoms, particularly preferably 6 to 15 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, and specific examples may include biphenyl, terphenyl, tetraphenyl, 1-phenylnaphthyl, 2-phenylnaphthyl, 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, and specific examples may include naphthyl, anthraceneyl, phenanthryl, pyrene, peryl, fluorenyl, benzo[a]fluorenyl, triphenylene, fluoranyl, spirofluorenyl, spirodifluorenyl, etc., but not limited to this.

[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, or phosphorus atoms, and preferably have 2 to 30 carbon atoms, more preferably 2 to 18 carbon atoms, particularly preferably 2 to 15 carbon atoms, and most preferably 2 to 12 carbon atoms. The linking site of the heteroaryl group can be located on a cyclic carbon atom or on a cyclic heteroatom. The heteroaryl group can be a monocyclic heteroaryl, polycyclic heteroaryl, or fused-ring heteroaryl. Specific examples of the monocyclic heteroaryl group may include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, thiopheneyl, pyrroloyl, oxazolyl, thiazolyl, imidazolyl, etc., but are not limited thereto; specific examples of the polycyclic heteroaryl group may include bipyridyl, bipyrimidinyl, phenylpyridinyl, phenylpyrimidinyl, etc., but are not limited thereto; specific examples of the fused-ring heteroaryl group may include quinolinyl, isoquinolinyl, benzo[a]quinolinyl, benzo[a]isoquinolinyl, quinazolinyl, quinoxalinyl, benzo[a]quinazolinyl, benzo[a]quinazolinyl, benzo[a] Quinoxolinyl, o-phenantholinyl, naphridyl, indolyl, benzothiopheneyl, benzofuranyl, benzooxazolyl, benzoimidazoyl, benzothiazoyl, dibenzofuranyl, benzodibenzofuranyl, dibenzothiopheneyl, benzodibenzothiopheneyl, dibenzooxazolyl, dibenzoimidazoyl, dibenzothiazoyl, carbazoleyl, benzocarbazoleyl, acridineyl, 9,10-dihydroacridyl, phenoxazinyl, phenthiazinyl, phenoxazinyl, spirofluorenexanthraceneyl, spirofluorenethixanthraceneyl, etc., but not limited to these.

[0032] The arylene group referred to in this invention refers to the general term for the divalent group obtained by removing two hydrogen atoms from the aromatic nucleus of an aromatic hydrocarbon molecule. It can be a monocyclic arylene, a polycyclic arylene, or a fused-ring arylene, preferably having 6 to 30 carbon atoms, more preferably 6 to 25 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 18 carbon atoms, and most preferably 6 to 12 carbon atoms. Specific examples may include phenylene, biphenylene, terphenylene, naphthylene, anthracene, phenanthrene, pyrene, trimethyleneene, perylene, fluorene, fluorenylene, phenylfluorene, etc., but are not limited thereto.

[0033] The heteroaryl group described in this invention refers to a divalent group in which at least one carbon atom of the aryl group is replaced by a heteroatom. The heteroatom is selected from O, S, N, Si, B, P, etc., but is not limited thereto. Preferably, it has 2 to 30 carbon atoms, more preferably 2 to 18 carbon atoms, particularly preferably 2 to 15 carbon atoms, and most preferably 2 to 12 carbon atoms. The heteroaryl group includes monocyclic heteroaryl, polycyclic heteroaryl, fused-ring heteroaryl, or combinations thereof. Examples of the heteroaryl group include, but are not limited to, the following groups: pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, quinazolinyl, naphthinyl, dibenzofuran, dibenzothiophene, etc., but are not limited thereto.

[0034] The substituents described in the "substituted or unsubstituted" of this invention may be independently selected from deuterium, cyano, nitro, amino, halogen atoms, substituted or unsubstituted C1-C12 alkyl groups, substituted or unsubstituted C3-C12 alicyclic groups, C1-C30 silyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, substituted or unsubstituted C1-C12 alkoxy groups, substituted or unsubstituted C1-C6 alkylthio groups, substituted or unsubstituted C1-C12 alkylamino groups, substituted or unsubstituted C6-C30 aryloxy groups, substituted or unsubstituted C6-C30 arylamino groups, etc., but are not limited thereto, or adjacent substituents may be linked to form a ring. Preferred compounds include deuterium, cyano, nitro, amino, halogen atoms, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, C2-C30 heteroaryl, and C1-C12 alkoxy. Specific examples may include deuterium, fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclopropyl, cyclohexyl, adamantyl, norbornel, phenyl, tolyl, mesitylene, and pentadeuterium. Phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, perylene, pyrene, fluoranyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, spirofluorenyl, carbazole, 9-phenylcarbazole, 9,9'-spirodifluorenyl, carbazole-indole, pyrrole, furanyl, thiophene, benzofuran The substituents include, but are not limited to, uranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, pyridinyl, pyrimidinyl, pyridazinyl, triazinyl, oxazolyl, thiazolyl, imidazolyl, benzooxazolyl, benzothiazolyl, benzotriazolyl, benzoimidazolyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, phenothiazinyl, phenothiazinyl, acridineyl, etc. Alternatively, when there are multiple substituents, the multiple substituents may be the same or different from each other; or adjacent substituents may be linked to form a ring.

[0035] The "linked ring formation" described in this invention refers to two groups being linked together by chemical bonds and optionally undergoing aromatization. Examples are shown below:

[0036]

[0037] 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, or a fused ring, such as benzene, naphthalene, indene, cyclopentene, cyclopentane, cyclopentanophenene, cyclohexene, cyclohexane, cyclohexanophenene, quinoline, isoquinoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, phenanthrene, or pyrene, but is not limited thereto.

[0038] The term "at least one" as used in this invention includes, where permitted, one, two, three, four, five, six, seven, eight, or more.

[0039] The term "one or more" as used in this invention includes, where permitted, one, two, three, four, five, six, seven, eight, or more.

[0040] This invention provides a compound containing a fluorene group, wherein the compound containing the fluorene group is selected from the structure shown in Chemical Formula 1.

[0041]

[0042] Wherein, Ar1 and Ar2 are independently selected from the following formula a;

[0043] * indicates a connection site;

[0044] The same or different E is selected from C(R3) or N, and the same or different R3 is selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic group, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted silyl, or two adjacent R3 are connected to form a substituted or unsubstituted ring;

[0045] The same or different X is selected from C(Rm) or N, and the same or different Rm is selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic group, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted silyl, or two adjacent Rm are connected to form a substituted or unsubstituted ring;

[0046] The Y is selected from O, S, C(RaRb), and N(Rc). The Ra and Rb, whether the same or different, are selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, and substituted or unsubstituted silyl. The Rc, whether the same or different, is selected from any one of substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, and substituted or unsubstituted silyl.

[0047] R1 and R2 are independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic group, substituted or unsubstituted silyl group, or R1 or R2 are directly bonded to L, or R1 and R2 are combined with each other to form a substituted or unsubstituted C3-C12 aliphatic ring;

[0048] The R0 is selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, and substituted or unsubstituted silyl; or two adjacent R0s are connected to form a substituted or unsubstituted benzene ring or naphthalene ring; the v is selected from 1, 2, or 3;

[0049] Rx is selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, and substituted or unsubstituted silyl; m is selected from 1 or 2;

[0050] The L, L1, and L2 are independently selected from any one of single-bonded, substituted or unsubstituted C6-C30 arylene, or substituted or unsubstituted C2-C30 heteroarylene.

[0051] At least one of R0, R1, R2, R3, Rm, Rx, Ra, Rb, Rc, L, L1, and L2 contains one or more deuterium.

[0052] Preferably, the chemical formula 1 is selected from any one of the structures shown below.

[0053]

[0054] Preferably, the R0 is the same as or different from hydrogen, deuterium, cyano, halogen, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, or substituted or unsubstituted groups of the following: methyl, ethyl, propyl, butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norberyl. The substituted or unsubstituted benzene ring or naphthyl ring is formed by the connection of any one or combination of alkyl, phenyl, biphenyl, naphthyl, anthracene, phenanthrene, triphenylene, fluorenyl, spirodifluorenyl, benzofuranyl, dibenzofuranyl, benzothiophene, dibenzothiophene, carbazole, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, pyridyl, pyrimidinyl, quinolinyl, or two adjacent R0s.

[0055] The "substituted" group in R0 is selected from any one of deuterium, cyano, nitro, halogen, methyl, ethyl, propyl, butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, and tritert-butylsilyl.

[0056] More preferably, R0 is selected from deuterium.

[0057] Preferably, the Choose any one of the structures shown below.

[0058]

[0059] The definition of X is as described herein;

[0060] R1', R2', and R1" are independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic, and substituted or unsubstituted silyl groups;

[0061] The ring A is selected from substituted or unsubstituted C3-C12 aliphatic rings.

[0062] Further preferably, R1', R2', and R1" are independently selected from hydrogen, deuterium, cyano, halogen, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, or substituted or unsubstituted groups of any one or a combination thereof: methyl, ethyl, propyl, butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, camphene.

[0063] More preferably, ring A is selected from any one of the following groups:

[0064]

[0065] The R4 is the same or different from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, and substituted or unsubstituted silyl.

[0066] The same or different a1 is selected from 0, 1, 2, 3 or 4; the same or different a2 is selected from 0, 1, 2, 3, 4, 5 or 6; the same or different a3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the same or different a4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; the same or different a5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12; the same or different a6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 or 14; the same or different a7 is selected from 0, 1 or 2.

[0067] Preferably, the Rm, whether the same or different, is selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic group, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or substituted or unsubstituted silyl, or two adjacent Rm are connected to form a substituted or unsubstituted benzene ring, naphthalene ring, or C3-C8 aliphatic ring.

[0068] Preferably, the Choose any one of the structures shown below.

[0069]

[0070]

[0071] The Rm, whether the same or different, is selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, and substituted or unsubstituted silyl.

[0072] The R4 is the same or different from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, and substituted or unsubstituted silyl.

[0073] The same or different a1 is selected from 0, 1, 2, 3, or 4; the same or different a2 is selected from 0, 1, 2, 3, 4, 5, or 6; the same or different a3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the same or different a4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; the same or different a5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12; the same or different a6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, or 14; the same or different a7 is selected from 0, 1, or 2; the same or different a8 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; the same or different a9 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; the a 10 The same or different values ​​are selected from 0, 1, 2, 3, 4 or 5; the same or different values ​​of a0 are selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11;

[0074] The values ​​of b1 (which may be the same or different) are selected from 0, 1, 2, 3, 4, 5, 6, or 7; the values ​​of b2 (which may be the same or different) are selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the values ​​of b3 (which may be the same or different) are selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; the values ​​of b4 (which may be the same or different) are selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11; the values ​​of b5 (which may be the same or different) are selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 1. 2 or 13; the same or different b6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18 or 19; the same or different b7 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14 or 15; the same or different b8 is selected from 0, 1, 2, 3, 4, 5 or 6; the same or different b9 is selected from 0, 1, 2, 3, 4 or 5.

[0075] Preferably, the Rm is the same as or different from hydrogen, deuterium, cyano, halogen, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, or substituted or unsubstituted groups of the following: methyl, ethyl, propyl, butyl, cyclopropyl, cyclobutyl, Cyclopentyl, cyclohexyl, adamantyl, norbornel, phenyl, biphenyl, naphthyl, anthracene, phenanthrene, triphenylene, fluorenyl, spirodifluorenyl, benzofuranyl, dibenzofuranyl, benzothiophene, dibenzothiophene, carbazole, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, pyridyl, pyrimidinyl, quinolinyl, or any combination thereof.

[0076] The "substituted" group in Rm is selected from any one of deuterium, cyano, nitro, halogen, methyl, ethyl, propyl, butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, and tritert-butylsilyl.

[0077] Preferably, the R4 groups, whether identical or different, are selected from hydrogen, deuterium, cyano, halogen, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, or substituted or unsubstituted groups of the following: methyl, ethyl, propyl, butyl, cyclopropyl, cyclobutyl, etc. Cyclopentyl, cyclohexyl, adamantyl, norbornel, phenyl, biphenyl, naphthyl, anthracene, phenanthrene, triphenylene, fluorenyl, spirodifluorenyl, benzofuranyl, dibenzofuranyl, benzothiophene, dibenzothiophene, carbazole, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, pyridyl, pyrimidinyl, quinolinyl, or any combination thereof.

[0078] The "substituted" group in R4 is selected from any one of deuterium, cyano, nitro, halogen, methyl, ethyl, propyl, butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, and tritert-butylsilyl.

[0079] Preferably, Rm is selected from deuterium.

[0080] Preferably, formula a is selected from any of the following structures.

[0081]

[0082] The limitations of Y and Rx are as described in this document;

[0083] The R3 is the same or different from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, and substituted or unsubstituted silyl.

[0084] The n1 that is the same or different is selected from 0, 1, 2, 3 or 4; the n2 that is the same or different is selected from 0, 1, 2 or 3; the n3 that is the same or different is selected from 0, 1 or 2; the n4 that is the same or different is selected from 0, 1, 2, 3, 4, 5 or 6; the n5 that is the same or different is selected from 0, 1, 2, 3, 4 or 5; the n6 that is the same or different is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8.

[0085] More preferably, formula a is selected from any of the following structures.

[0086]

[0087]

[0088] Preferably, the R3 is the same as or different from hydrogen, deuterium, cyano, halogen, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, or substituted or unsubstituted groups of the following: methyl, ethyl, propyl, butyl, cyclopropyl, cyclobutyl, Cyclopentyl, cyclohexyl, adamantyl, norbornel, phenyl, biphenyl, naphthyl, anthracene, phenanthrene, triphenylene, fluorenyl, spirodifluorenyl, benzofuranyl, dibenzofuranyl, benzothiophene, dibenzothiophene, carbazole, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, pyridyl, pyrimidinyl, quinolinyl, or any combination thereof.

[0089] Preferably, the Rx is the same as or different from hydrogen, deuterium, cyano, halogen, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, or substituted or unsubstituted groups of the following: methyl, ethyl, propyl, butyl, cyclopropyl, cyclobutyl, Cyclopentyl, cyclohexyl, adamantyl, norbornel, phenyl, biphenyl, naphthyl, anthracene, phenanthrene, triphenylene, fluorenyl, spirodifluorenyl, benzofuranyl, dibenzofuranyl, benzothiophene, dibenzothiophene, carbazole, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, pyridyl, pyrimidinyl, quinolinyl, or any combination thereof.

[0090] The "substituted" group in Rx is selected from any one of deuterium, cyano, nitro, halogen, methyl, ethyl, propyl, butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, and tritert-butylsilyl.

[0091] Preferably, Ra and Rb are independently selected from hydrogen, deuterium, cyano, halogen, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, or substituted or unsubstituted groups of the following: methyl, ethyl, propyl, butyl, cyclopropyl, cyclobutyl, ... Cyclopentyl, cyclohexyl, adamantyl, norbornel, phenyl, biphenyl, naphthyl, anthracene, phenanthrene, triphenylene, fluorenyl, spirodifluorenyl, benzofuranyl, dibenzofuranyl, benzothiophene, dibenzothiophene, carbazole, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, pyridyl, pyrimidinyl, quinolinyl, or any combination thereof.

[0092] Preferably, the "substituted" groups in Ra and Rb are selected from any one of deuterium, cyano, nitro, halogen, methyl, ethyl, propyl, butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, and tritert-butylsilyl.

[0093] Preferably, Rc is selected from trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, or substituted or unsubstituted groups of the following: methyl, ethyl, propyl, butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, phenyl, biphenyl, naphthyl, anthracene, phenanthrene, phenylenetriene, fluorenyl, spirodifluorenyl, benzofuranyl, dibenzofuranyl, benzothiophene, dibenzothiophene, carbazole, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, pyridyl, pyrimidinyl, quinolinyl, or any combination thereof.

[0094] Preferably, the "substituted" group in Rc is selected from any one of deuterium, cyano, nitro, halogen, methyl, ethyl, propyl, butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, and tritert-butylsilyl.

[0095] Preferably, R3 and / or Rx are selected from deuterium.

[0096] Preferably, Rx is selected from pentadeuterated phenyl, heptadeuterated naphthyl, and nonadeuterated biphenyl.

[0097] Preferably, L, L1, and L2 are selected from single bonds or any one of the following groups:

[0098]

[0099] The Z that is the same or different is selected from C(R6) or N, and the R6 that is the same or different is selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted silyl; or a substituted or unsubstituted ring is formed between two adjacent R6s;

[0100] W1 and W3 are independently selected from any one of O, S, C(RdRe), and N(Rf);

[0101] The W2 is selected from CH or N;

[0102] The Rd and Re are independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C2-C18 heteroaryl, substituted or unsubstituted silyl, or a substituted or unsubstituted ring is formed between two adjacent Rd and Re.

[0103] The Rf is selected from any one of the following: substituted or unsubstituted C1-C12 alkyl groups, substituted or unsubstituted C3-C12 alicyclic groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, and substituted or unsubstituted silyl groups.

[0104] Preferably, the R6 groups, whether identical or different, are selected from hydrogen, deuterium, cyano, halogen, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, or substituted or unsubstituted groups of the following: methyl, ethyl, propyl, butyl, cyclopropyl, cyclobutyl, etc. Cyclopentyl, cyclohexyl, adamantyl, norbornel, phenyl, biphenyl, naphthyl, anthracene, phenanthrene, triphenylene, fluorenyl, spirodifluorenyl, benzofuranyl, dibenzofuranyl, benzothiophene, dibenzothiophene, carbazole, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, pyridyl, pyrimidinyl, quinolinyl, or any combination thereof.

[0105] Preferably, Rd and Re are independently selected from hydrogen, deuterium, cyano, halogen, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, or substituted or unsubstituted groups of the following: methyl, ethyl, propyl, butyl, cyclopropyl, cyclobutyl, ... Cyclopentyl, cyclohexyl, adamantyl, norbornel, phenyl, biphenyl, naphthyl, anthracene, phenanthrene, triphenylene, fluorenyl, spirodifluorenyl, benzofuranyl, dibenzofuranyl, benzothiophene, dibenzothiophene, carbazole, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, pyridyl, pyrimidinyl, quinolinyl, or any combination thereof.

[0106] Preferably, Rf is selected from trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, or substituted or unsubstituted groups of the following: methyl, ethyl, propyl, butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, phenyl, biphenyl, naphthyl, anthracene, phenanthrene, phenylenetriene, fluorenyl, spirodifluorenyl, benzofuranyl, dibenzofuranyl, benzothiopheneyl, dibenzothiopheneyl, carbazoleyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, pyridyl, pyrimidinyl, quinolinyl, or any combination thereof.

[0107] Preferably, R6 is selected from deuterium.

[0108] Preferably, at least one of L, L1, and L2 contains one or more deuterium.

[0109] The presence of one or more deuterium atoms in L, L1, and L2 means that at least one hydrogen atom in L, L1, and L2 is replaced by deuterium. Specifically, the presence of one or more deuterium atoms in L means that at least one hydrogen atom in L is replaced by deuterium; the presence of one or more deuterium atoms in L1 means that at least one hydrogen atom in L1 is replaced by deuterium; and the presence of one or more deuterium atoms in L2 means that at least one hydrogen atom in L2 is replaced by deuterium.

[0110] Preferably, L contains one or more deuterium; preferably, L1 and / or L2 contain at least one or more deuterium.

[0111] Preferably, at least one of L, L1, and L2 contains one, two, three, four, five, six, seven, eight, or more deuterium.

[0112] Preferably, one (L, L1, or L2), two (L and L1; L and L2; L1 and L2) or three of L, L1, and L2 are selected from single bonds or any of the following groups.

[0113]

[0114]

[0115] The same or different c1 is selected from 1, 2, 3, or 4; the same or different c2 is selected from 1, 2, 3, 4, 5, 6, 7, or 8; the same or different c3 is selected from 1, 2, 3, 4, 5, or 6; the same or different c4 is selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; the same or different c5 is selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12; the same or different c6 is selected from 1, 2, or 3; the same or different c7 is selected from 1 or 2; the same or different c8 is selected from 1, 2, 3, 4, or 5; the same or different c9 is selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, or 14.

[0116] Most preferably, the compound is selected from any one of the structures shown below.

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133] The above lists some specific structural forms of compounds represented by chemical formula 1 according to the present invention, but the present invention is not limited to these listed chemical structures. Any structure based on the structure shown in chemical formula 1, with substituents as defined above, should be included.

[0134] Preferably, the organic electroluminescent device includes an anode, a cathode, and an organic layer located between the anode and the cathode, the organic layer comprising at least one of the compounds described in this invention.

[0135] Preferably, the organic layer includes a light-emitting layer and an electron transport region, wherein the light-emitting layer or the electron transport region comprises at least one of the compounds described in this invention.

[0136] Preferably, the organic layer includes an electron transport region, which includes at least one of the compounds described in this invention.

[0137] Preferably, the organic layer includes an electron transport region, the electron transport region includes an electron transport layer, and the electron transport layer includes at least one of the compounds described in this invention.

[0138] Preferably, the organic layer includes an electron transport region, the electron transport region includes a hole blocking layer, and the hole blocking layer includes at least one of the compounds described in this invention.

[0139] Preferably, the organic layer includes a light-emitting layer, which includes at least one of the compounds described in this invention.

[0140] Preferably, the organic layer comprises a light-emitting layer, the light-emitting layer comprises a host material, and the host material comprises at least one of the compounds described in this invention.

[0141] This invention does not particularly limit the materials of the thin films in the organic electroluminescent device; substances known in the art can be used. The organic functional layers of the aforementioned organic electroluminescent device and the electrodes on both sides of the device are described below:

[0142] The anode of this invention is preferably made of a material with a high work function. The anode includes, but is not limited to, the materials described below: metals or alloys thereof, metal oxides, multilayer materials, conductive polymers, etc. Specific examples may include gold (Au), indium tin oxide (ITO), zinc oxide (ZnO), indium tin oxide / silver / indium tin oxide (ITO / Ag / ITO), polyaniline, etc., but are not limited thereto. The hole injection layer material of this invention is preferably a material with good hole-accepting ability. The hole injection layer material may include, but is not limited to, metalloporphyrins, oligothiophenes, anthraquinone compounds, arylamine derivatives, perylene derivatives, hexanitrile hexaazabenzophenanthrene compounds, quinacridone compounds, anthraquinone compounds, and conductive polymers based on polyaniline and polythiophene, etc.

[0143] The hole injection layer material described in this invention is preferably a material with good hole-accepting ability. The hole injection layer material may include, but is not limited to, metalloporphyrins, oligothiophenes, anthraquinone compounds, arylamine derivatives, perylene derivatives, hexanitrile hexaazabenzophenanthrene compounds, quinacridone compounds, anthraquinone compounds, and conductive polymers based on polyaniline and polythiophene.

[0144] The hole transport layer material described in this invention is preferably a material with high hole mobility. The hole transport layer material may include, but is not limited to, biphenyl diamine derivatives, triarylamine derivatives, carbazole derivatives, fluorene derivatives, stilbene derivatives, phthalocyanine compounds, anthraquinone compounds, quinacridone compounds, hexanitrile hexaazabenzophenanthrene compounds, polythiophene, polyaniline, polyvinylcarbazole, etc.

[0145] The luminescent layer material described in this invention can use red, green, or blue luminescent materials, and typically comprises a host material and dopants. The luminescent layer material may contain multiple host materials and multiple dopants. The dopants can be simple fluorescent or phosphorescent materials, or a combination of fluorescent and phosphorescent materials. The doping ratio of the host material and the dopants can vary depending on the materials used; preferably, the doping concentration of the dopant, based on the host compound, is less than 20 wt%. Fluorescent compounds can be used as dopants, 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]quinolineazine-11-one (C545T), 4,4'-bis(9-ethyl-3-carbazolevinyl)-1,1'-biphenyl (BCzVBi), 4,4'-bis[4-(di-p-tolylamino)styryl]biphenyl (DPAVBi), etc. Phosphorescent materials can also be used, such as iridium complexes, osmium complexes, platinum complexes and other metal complexes. Examples include bis(4,6-difluorophenylpyridine-N,C2)pyridinecarboxylated iridium (FIrpic), tri(2-phenylpyridine)iridium (Ir(ppy)3), acetylacetonate di(2-phenylpyridine)iridium (Ir(ppy)2(acac)), etc.

[0146] The host material of the luminescent layer needs to possess bipolar charge transport properties and appropriate energy levels to effectively transfer excitation energy to the guest luminescent material. Besides using the compound of Formula 1 provided in this invention alone, the host material can also be a combination of an n-type host material and a p-type host material. When used in combination with a p-type host material, the concentration of the n-type host material, based on the compound of Formula 1, is preferably 1 wt% to 99 wt%, more preferably 20 wt% to 80 wt%, and particularly preferably 30 wt% to 70 wt%. It may also contain anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentane derivatives, phenanthrene derivatives, fluoranthene derivatives, and heterocyclic compounds including carbazole derivatives, dibenzofuran derivatives, dibenzothiophene derivatives, pyrimidine derivatives, stilbeneylaryl derivatives, mestilbene derivatives, etc., but is not limited to these.

[0147] The electron transport material described in this invention is required to have excellent electron transport performance, effectively transporting electrons from the cathode to the light-emitting layer, and possessing a high electron mobility. In addition to the compound of Formula 1 provided in this invention, it may also contain any one or more of the following compounds, but is not limited to: thiazole derivatives, quinoline derivatives, benzimidazole derivatives, oxazazole derivatives, azirbenzene derivatives, diazanthracene derivatives, silicon-containing heterocyclic compounds, boron-containing heterocyclic compounds, cyano compounds, phenanthroline derivatives, metal chelates, etc.

[0148] The hole-blocking material in the electron transport region described in this invention requires a high triplet energy level and good electron transport performance. In addition to the compound of Formula 1 provided in this invention, it may also contain any one or more of the following compounds: thiazole derivatives, quinoline derivatives, benzimidazole derivatives, oxazole derivatives, azirbenzene derivatives, diazanthracene derivatives, silicon-containing heterocyclic compounds, boron-containing heterocyclic compounds, cyano compounds, phenanthroline derivatives, metal chelates, etc., but is not limited thereto.

[0149] The electron injection layer material described in this invention is preferably a material with good electron-accepting ability. The electron injection layer material may include metals, 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, metal complexes, metal oxides, and other substances with high electron-injection properties. Specific examples may include: Li, Ca, Sr, LiF, CsF, CaF2, BaO, Li2CO3, CaCO3, Li2C2O4, Cs2C2O4, CsAlF4, Al2O3, MoO3, MgF2, LiO, Yb, Tb, cesium 8-hydroxyquinoline, tris(8-hydroxyquinoline)aluminum, etc., but are not limited to these.

[0150] The cathode of this invention is preferably made of a material with a low work function. The cathode includes, but is not limited to, the materials described below, metals or their alloys, laminated materials, etc. Specific examples may include aluminum (Al), silver (Ag), lithium (Li), magnesium (Mg), magnesium:silver (Mg:Ag), etc., but are not limited to these.

[0151] The following is one method for preparing the compound represented by Formula 1 of this invention, but the preparation method of this invention is not limited thereto. The core structure of the compound of Formula 1 can be prepared by the reaction route shown below, the substituents can be bonded by methods known in the art, and the type and position or number of substituents can be changed according to techniques known in the art.

[0152] [Synthesis Route]

[0153] Preparation of compounds of formula 1:

[0154] There are no particular limitations on the preparation method of the compound represented by Chemical Formula 1 of this invention, and conventional methods well known to those skilled in the art can be used. For example, carbon-carbon coupling reaction, Miyaura borylation reaction, etc., are described below:

[0155] Method 1 is as follows, when -L1-Ar1 and -L2-Ar2 are the same:

[0156]

[0157] Method 2 is as follows, when -L1-Ar1 and -L2-Ar2 are different or the same:

[0158]

[0159] Xa, Xb, and Xc are each independently selected from I, Br, and Cl; M is selected from... Any one of them; the limitations of X, R1, R2, R0, Ar1, Ar2, L, L1, L2 are the same as those described above.

[0160] Raw materials and reagents: This invention does not impose any particular limitations on the raw materials or reagents used in the following synthesis examples. They can be commercially available products or prepared using methods well-known to those skilled in the art. All raw materials and reagents used in this invention are of reagent purity.

[0161] Instruments: G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer (Waters Instruments, UK); Vario ELcube organic elemental analyzer (Elementar Instruments, Germany)

[0162] Synthesis Example 1: Preparation of Compound 8

[0163]

[0164] Preparation of intermediate c-8:

[0165] Under argon protection, a-8 (38.09 g, 160.00 mmol), b-8 (39.61 g, 160.00 mmol), tetrakis(triphenylphosphine)palladium (1.85 g, 1.60 mmol), potassium acetate (31.40 g, 320.00 mmol), 570 mL toluene, 190 mL ethanol, and 190 mL water were added sequentially to a reaction flask. The mixture was stirred and refluxed for 3 hours. After the reaction was completed, the mixture was cooled to room temperature, filtered to obtain a filter cake, washed with ethanol, and finally recrystallized from toluene to obtain intermediate c-8 (47.35 g, yield 82%). The HPLC purity was ≥99.87%. Mass spectrometry m / z: 360.1567 (theoretical value: 360.1552).

[0166] Preparation of intermediate B-8:

[0167] Under nitrogen protection, C-8 (46.92 g, 130.00 mmol), pinacol diboronate (33.01 g, 130.00 mmol), potassium acetate (28.46 g, 290.00 mmol), 1,1'-bis(diphenylphosphine)ferrocene palladium dichloride (1.59 g, 2.17 mmol), and 1,4-dioxane (1000 mL) were added sequentially to the reaction flask. The mixture was then heated for 4 hours. After the reaction was completed, the mixture was cooled to room temperature, and 1000 mL of distilled water was added. The mixture was then extracted with ethyl acetate (600 mL × 3). The organic layer was dried over anhydrous magnesium sulfate, and the ethyl acetate was removed by rotary evaporation. The mixture was then recrystallized from toluene:methanol (40:1) and dried to obtain intermediate B-8 (45.88 g, 78% yield); HPLC purity ≥99.83%. Mass spectrometry m / z: 452.2781 (theoretical value: 452.2794).

[0168] Preparation of intermediate H-8:

[0169] Under nitrogen protection, intermediates m-8 (13.52 g, 50.00 mmol), A-8 (17.80 g, 100.00 mmol), tetrakis(triphenylphosphine)palladium (1.16 g, 1.00 mmol), potassium acetate (19.63 g, 200.00 mmol), 270 mL toluene, 90 mL ethanol, and 90 mL water were added sequentially to a reaction flask. The mixture was stirred and the reaction system was heated under reflux for 4 hours. After the reaction was completed, the mixture was cooled to room temperature, filtered to obtain a filter cake, washed with ethanol, and finally recrystallized from toluene to obtain intermediate H-8 (16.02 g, yield 85%). The HPLC purity was ≥99.86%. Mass spectrometry m / z: 376.0159 (theoretical value: 376.0147).

[0170] Preparation of compound 8:

[0171] Under nitrogen protection, H-8 (11.31 g, 30.00 mmol), B-8 (13.57 g, 30.00 mmol), Pd2(dba)3 (0.33 g, 0.36 mmol), tri-tert-butylphosphine (1.44 mL of 0.5 M toluene solution, 0.72 mmol), potassium carbonate (6.63 g, 48.00 mmol), and 300 mL of tetrahydrofuran were added sequentially to a reaction flask. The mixture was stirred and the reaction system was heated under reflux for 5 hours. After the reaction was completed, the mixture was cooled to room temperature, filtered to obtain a filter cake, and washed with a small amount of toluene. Finally, the filter cake was recrystallized from toluene to obtain compound 8 (14.41 g, yield 72%), with an HPLC purity ≥99.98%. Mass spectrometry m / z: 666.2308 (theoretical value: 666.2322). Theoretical elemental content (%) C 47 H 26 D6S2: C, 84.64; H, 5.74. Analyzed elemental composition (%): C, 84.62; H, 5.76. Synthesis Example 2: Preparation of Compound 25

[0172]

[0173] According to the preparation method in Example 1, a-8 was replaced with an equimolar amount of a-25, b-8 with an equimolar amount of b-25, A-8 with an equimolar amount of A-25, and B-8 with an equimolar amount of B-25, yielding compound 25 (15.16 g); HPLC purity ≥ 99.93%. Mass spectrometry m / z: 742.3696 (theoretical value: 742.3687). Theoretical elemental content (%) C 55 H 34 D8O2: C, 88.91; H, 6.78. Measured elemental content (%): C, 88.94; H, 6.75.

[0174] Synthesis Example 3: Preparation of Compound 34

[0175]

[0176] According to the preparation method in Synthesis Example 1, a-8 was replaced with an equimolar amount of a-34, b-8 with an equimolar amount of b-34, and B-8 with an equimolar amount of B-34, yielding compound 34 (14.63 g); HPLC purity ≥ 99.95%. Mass spectrometry m / z: 706.2260 (theoretical value: 706.2271). Theoretical elemental content (%) C 49 H 26 D6OS2: C, 83.25; H, 5.42. Measured elemental content (%): C, 83.22; H, 5.45.

[0177] Synthesis Example 4: Preparation of Compound 45

[0178]

[0179] According to the preparation method in Example 1, a-8 was replaced with an equimolar amount of a-34, b-8 with an equimolar amount of b-45, A-8 with an equimolar amount of A-45, and B-8 with an equimolar amount of B-45, yielding compound 45 (15.47 g); HPLC purity ≥ 99.97%. Mass spectrometry m / z: 736.2934 (theoretical value: 736.2918). Theoretical elemental content (%) C 52 H 32 D3N3O2: C, 84.76; H, 5.20; N, 5.70. Measured elemental content (%): C, 84.71; H, 5.22; N, 5.73.

[0180] Synthesis Example 5: Preparation of Compound 49

[0181]

[0182] According to the preparation method in Synthesis Example 1, a-8 was replaced with an equimolar amount of a-34, b-8 with an equimolar amount of b-49, A-8 with an equimolar amount of A-25, and B-8 with an equimolar amount of B-49, yielding compound 49 (14.23 g); HPLC purity ≥ 99.94%. Mass spectrometry m / z: 658.2820 (theoretical value: 658.2810). Theoretical elemental content (%) C 49 H 30 D4O2: C, 89.33; H, 5.81. Measured elemental content (%): C, 89.30; H, 5.84.

[0183] Synthesis Example 6: Preparation of Compound 94

[0184]

[0185] According to the preparation method in Example 1, A-8 was replaced with an equimolar amount of A-25 and B-8 was replaced with an equimolar amount of B-94 to obtain compound 94 (13.11 g); HPLC purity ≥ 99.91%. Mass spectrometry m / z: 582.2482 (theoretical value: 582.2497). Theoretical elemental content (%) C 43 H 26 D4O2: C, 88.63; H, 5.88. Measured elemental content (%): C, 88.66; H, 5.85.

[0186] Synthesis Example 7: Preparation of Compound 110

[0187]

[0188] According to the preparation method in Example 1, A-8 was replaced with an equimolar amount of A-110 and B-8 was replaced with an equimolar amount of B-94 to obtain compound 110 (13.65 g); HPLC purity ≥ 99.96%. Mass spectrometry m / z: 614.2055 (theoretical value: 614.2040). Theoretical elemental content (%) C 43 H 26 D4S2: C, 84.00; H, 5.57. Measured elemental content (%): C, 84.03; H, 5.54.

[0189] Synthesis Example 8: Preparation of Compound 114

[0190]

[0191] According to the preparation method in Synthesis Example 1, a-8 was replaced with an equimolar amount of a-114, b-8 with an equimolar amount of b-114, A-8 with an equimolar amount of A-25, and B-8 with an equimolar amount of B-114, yielding compound 114 (13.86 g); HPLC purity ≥ 99.92%. Mass spectrometry m / z: 659.2747 (theoretical value: 659.2762). Theoretical elemental content (%) C 48 H 29 D4NO2: C, 87.38; H, 5.65; N, 2.12. Measured elemental content (%): C, 87.33; H, 5.66; N, 2.16.

[0192] Synthesis Example 9: Preparation of Compound 125

[0193]

[0194] According to the preparation method in Example 1, b-8 was replaced with an equimolar amount of b-125, A-8 with an equimolar amount of A-125, and B-8 with an equimolar amount of B-125 to obtain compound 125 (15.87 g); HPLC purity ≥ 99.98%. Mass spectrometry m / z: 734.3140 (theoretical value: 734.3123). Theoretical elemental content (%) C 55 H 34 D4O2: C, 89.89; H, 5.76. Measured elemental content (%): C, 89.86; H, 5.79.

[0195] Synthesis Example 10: Preparation of Compound 134

[0196]

[0197] According to the preparation method in Example 1, A-8 was replaced with an equimolar amount of A-134 and B-8 was replaced with an equimolar amount of B-94 to obtain compound 134 (16.14 g); HPLC purity ≥ 99.93%. Mass spectrometry m / z: 736.3016 (theoretical value: 736.3028). Theoretical elemental content (%) C 53 H 32 D4N2O2: C, 86.39; H, 5.47; N, 3.80. Measured elemental content (%): C, 86.36; H, 5.48; N, 3.82.

[0198] Synthetic Example 11: Preparation of Compound 150

[0199]

[0200] According to the preparation method in Synthesis Example 1, a-8 was replaced with an equimolar amount of a-150, b-8 with an equimolar amount of b-125, A-8 with an equimolar amount of A-25, and B-8 with an equimolar amount of B-150, yielding compound 150 (14.58 g); HPLC purity ≥ 99.97%. Mass spectrometry m / z: 674.3136 (theoretical value: 674.3123). Theoretical elemental content (%) C 50 H 34 D4O2: C, 88.99; H, 6.27. Measured elemental content (%): C, 88.98; H, 6.28.

[0201] Synthesis Example 12: Preparation of Compound 160

[0202]

[0203] According to the preparation method in Synthesis Example 1, a-8 was replaced with an equimolar amount of a-160, b-8 with an equimolar amount of b-125, A-8 with an equimolar amount of A-160, and B-8 with an equimolar amount of B-160, yielding compound 160 (13.65 g); HPLC purity ≥ 99.95%. Mass spectrometry m / z: 640.2184 (theoretical value: 640.2196). Theoretical elemental content (%) C 45 H 28 D4S2: C, 84.33; H, 5.66. Measured elemental content (%): C, 84.35; H, 5.64.

[0204] Synthetic Example 13: Preparation of Compound 168

[0205]

[0206] According to the preparation method in Example 1, a-8 was replaced with an equimolar amount of a-168, b-8 with an equimolar amount of b-125, A-8 with an equimolar amount of A-25, and B-8 with an equimolar amount of B-168, yielding compound 168 (13.86); HPLC purity ≥99.91%. Mass spectrometry m / z: 632.2665 (theoretical value: 632.2653). Theoretical elemental content (%) C 47 H 28 D4O2: C, 89.21; H, 5.73. Measured elemental content (%): C, 89.24; H, 5.70.

[0207] Synthetic Example 14: Preparation of Compound 175

[0208]

[0209] According to the preparation method in Synthesis Example 1, a-8 was replaced with an equimolar amount of a-175, b-8 with an equimolar amount of b-125, A-8 with an equimolar amount of A-175, and B-8 with an equimolar amount of B-175, yielding compound 175 (12.96 g); HPLC purity ≥ 99.94%. Mass spectrometry m / z: 583.2440 (theoretical value: 583.2449). Theoretical elemental content (%) C 42 H 25 D4NO2: C, 86.42; H, 5.70; N, 2.40. Measured elemental content (%): C, 86.40; H, 5.71; N, 2.41.

[0210] Synthesis Example 15: Compound 182

[0211]

[0212] According to the preparation method in Example 1, A-8 was replaced with an equimolar amount of A-182 and B-8 was replaced with an equimolar amount of B-94 to obtain compound 182 (14.75 g); HPLC purity ≥ 99.96%. Mass spectrometry m / z: 682.2821 (theoretical value: 682.2810). Theoretical elemental content (%) C 51 H 30 D4O2: C, 89.71; H, 5.61. Measured elemental content (%): C, 89.70; H, 5.62.

[0213] Synthetic Example 16: Preparation of Compound 191

[0214]

[0215] According to the preparation method in Synthesis Example 1, A-8 was replaced with an equimolar amount of A-191 and B-8 was replaced with an equimolar amount of B-94 to obtain compound 191 (16.09 g); HPLC purity ≥ 99.92%. Mass spectrometry m / z: 734.3111 (theoretical value: 734.3123). Theoretical elemental content (%) C 55 H 34 D4O2: C, 89.89; H, 5.76. Measured elemental content (%): C, 89.86; H, 5.79.

[0216] Synthetic Example 17: Preparation of Compound 196

[0217]

[0218] According to the preparation method in Example 1, m-8 was replaced with an equimolar amount of m-196 and B-8 was replaced with an equimolar amount of B-94 to obtain compound 196 (13.28 g); HPLC purity ≥ 99.97%. Mass spectrometry m / z: 614.2052 (theoretical value: 614.2040). Theoretical elemental content (%) C 43 H 26 D4S2: C, 84.00; H, 5.57. Measured elemental content (%): C, 84.05; H, 5.52.

[0219] Synthesis Example 18: Preparation of Compound 206

[0220]

[0221] Preparation of intermediate d-206:

[0222] Under argon protection, A-8 (28.48 g, 160.00 mmol), b-114 (31.28 g, 160.00 mmol), tetrakis(triphenylphosphine)palladium (1.85 g, 1.60 mmol), potassium acetate (31.40 g, 320.00 mmol), 570 mL toluene, 190 mL ethanol, and 190 mL water were added sequentially to a reaction flask. The mixture was stirred and refluxed for 3 hours. After the reaction was completed, the mixture was cooled to room temperature, filtered to obtain a filter cake, washed with ethanol, and finally recrystallized from toluene to obtain intermediate d-206 (34.23 g, yield 86%); HPLC purity ≥99.89%. Mass spectrometry m / z: 248.0355 (theoretical value: 248.0365).

[0223] Preparation of intermediate A-206:

[0224] Under nitrogen protection, d-206 (32.34 g, 130.00 mmol), pinacol diboronate (33.01 g, 130.00 mmol), potassium acetate (28.46 g, 290.00 mmol), 1,1'-bis(diphenylphosphine)ferrocene palladium dichloride (1.59 g, 2.17 mmol), and 1,4-dioxane (1000 mL) were added sequentially to the reaction flask. The mixture was then heated to react for 4 hours. After the reaction was completed, the mixture was cooled to room temperature, and 1000 mL of distilled water was added. The mixture was then extracted with ethyl acetate (600 mL × 3). The organic layer was dried over anhydrous magnesium sulfate, and the ethyl acetate was removed by rotary evaporation. The mixture was then recrystallized from toluene:methanol (40:1) and dried to obtain intermediate A-206 (35.83 g, yield 81%); HPLC purity ≥99.86%. Mass spectrometry m / z: 340.1619 (theoretical value: 340.1606).

[0225] The remaining steps followed the preparation method of Example 1, except that A-8 was replaced with an equimolar amount of A-206 and B-8 was replaced with an equimolar amount of B-206, yielding compound 206 (16.42 g); HPLC purity ≥ 99.91%. Mass spectrometry m / z: 770.2906 (theoretical value: 770.2917). Theoretical elemental content (%) C 55 H 30 D8S2: C, 85.67; H, 6.01. Measured elemental content (%): C, 85.65; H, 6.03.

[0226] Synthetic Example 19: Preparation of Compound 259

[0227]

[0228] According to the preparation method in Synthesis Example 18, A-8 was replaced with an equimolar amount of A-25, b-114 with an equimolar amount of b-125, A-206 with an equimolar amount of A-259, and B-206 with an equimolar amount of B-259, yielding compound 259 (15.07 g); HPLC purity ≥ 99.98%. Mass spectrometry m / z: 738.3359 (theoretical value: 738.3374). Theoretical elemental content (%) C 55 H 30 D8O2: C, 89.40; H, 6.27. Measured elemental content (%): C, 89.45; H, 6.22.

[0229] Synthesis Example 20: Preparation of Compound 286

[0230]

[0231] According to the preparation method of Synthesis Example 18, A-8 was replaced with an equimolar amount of A-25, b-114 with an equimolar amount of b-8, A-206 with an equimolar amount of A-286, and B-206 with an equimolar amount of B-286, yielding compound 286 (17.19 g); HPLC purity ≥ 99.95%. Mass spectrometry m / z: 867.3875 (theoretical value: 867.3891). Theoretical elemental content (%) C 64 H 29 D 12 NO2: C, 88.55; H, 6.15; N, 1.61. Measured elemental content (%): C, 88.50; H, 6.17; N, 1.64.

[0232] Synthesis Example 21: Preparation of Compound 298

[0233]

[0234] According to the preparation method in Synthesis Example 18, A-8 was replaced with an equimolar amount of A-25, b-114 with an equimolar amount of b-298, and A-206 with an equimolar amount of A-298, yielding compound 298 (15.07 g); HPLC purity ≥ 99.94%. Mass spectrometry m / z: 738.3166 (theoretical value: 738.3153). Theoretical elemental content (%) C 53 H 30 D6N2O2: C, 86.15; H, 5.73; N, 3.79. Measured elemental content (%): C, 86.18; H, 5.75; N, 3.74.

[0235] Synthesis Example 22: Preparation of Compound 318

[0236]

[0237] According to the preparation method in Synthesis Example 18, d-206 was replaced with an equimolar amount of d-318, and A-206 was replaced with an equimolar amount of A-318 to obtain compound 318 (12.72 g); HPLC purity ≥ 99.96%. Mass spectrometry m / z: 588.2860 (theoretical value: 588.2873). Theoretical elemental content (%) C 43 H 20 D 10 O2: C, 87.72; H, 6.84. Measured elemental content (%): C, 87.74; H, 6.82.

[0238] Synthesis Example 23: Preparation of Compound 323

[0239]

[0240] According to the preparation method in Example 1, A-8 was replaced with an equimolar amount of A-323 and B-8 was replaced with an equimolar amount of B-206 to obtain compound 323 (13.88 g); HPLC purity ≥ 99.98%. Mass spectrometry m / z: 616.2178 (theoretical value: 616.2166). Theoretical elemental content (%) C43H24D6S2: C, 83.72; H, 5.88. Measured elemental content (%): C, 83.75; H, 5.86.

[0241] Synthesis Example 24: Preparation of Compound 356

[0242]

[0243] According to the preparation method in Synthesis Example 18, d-206 was replaced with an equimolar amount of d-356, A-206 was replaced with an equimolar amount of A-356, and B-206 was replaced with an equimolar amount of B-94 to obtain compound 356 (13.45 g); HPLC purity ≥ 99.92%. Mass spectrometry m / z: 622.2528 (theoretical value: 622.2542). Theoretical elemental content (%) C 43 H 18 D 12 S2: C, 82.91; H, 6.79. Measured elemental content (%): C, 82.96; H, 6.74.

[0244] Synthesis Example 25: Preparation of Compound 371

[0245]

[0246] According to the preparation method in Example 1, A-8 was replaced with an equimolar amount of A-371 and B-8 was replaced with an equimolar amount of B-206 to obtain compound 371 (15.56 g); HPLC purity ≥ 99.95%. Mass spectrometry m / z: 740.3485 (theoretical value: 740.3499). Theoretical elemental content (%) C 55 H 28 D 10 O2: C, 89.15; H, 6.53. Measured elemental content (%): C, 89.13; H, 6.55.

[0247] Synthesis Example 26: Preparation of Compound 377

[0248]

[0249] According to the preparation method in Example 1, a-8 was replaced with an equimolar amount of a-377, b-8 with an equimolar amount of b-377, A-8 with an equimolar amount of A-25, and B-8 with an equimolar amount of B-377, yielding compound 377 (13.18 g); HPLC purity ≥ 99.98%. Mass spectrometry m / z: 585.2696 (theoretical value: 585.2685). Theoretical elemental content (%) C 43 H 23 D7O2: C, 88.17; H, 6.36. Measured elemental content (%): C, 88.15; H, 6.38.

[0250] Synthesis Example 27: Preparation of Compound 410

[0251]

[0252] Preparation of intermediate B-410:

[0253] According to the preparation method of B-8 in Synthesis Example 1, a-8 was replaced with an equimolar amount of a-377 and b-8 was replaced with an equimolar amount of b-125 to obtain intermediate B-410 (41.84 g); HPLC purity ≥ 99.84%. Mass spectrometry m / z: 407.2940 (theoretical value: 407.2951).

[0254] Preparation of intermediate I-410:

[0255] Under nitrogen protection, intermediate m-410 (25.39 g, 80.00 mmol), A-8 (14.24 g, 80 mmol), tetrakis(triphenylphosphine)palladium (0.92 g, 0.80 mmol), potassium acetate (15.70 g, 160.00 mmol), 270 mL toluene, 90 mL ethanol, and 90 mL water were added sequentially to a reaction flask. The mixture was stirred and the reaction system was heated under reflux for 3 hours. After the reaction was completed, the mixture was cooled to room temperature, filtered to obtain a filter cake, washed with ethanol, and finally recrystallized from toluene to obtain intermediate I-410 (22.78 g, yield 88%); HPLC purity ≥99.86%. Mass spectrometry m / z: 321.9229 (theoretical value: 321.9219).

[0256] Preparation of intermediate H-410:

[0257] Under nitrogen protection, intermediates I-410 (16.18 g, 50.00 mmol), A-25 (8.10 g, 50.00 mmol), tetrakis(triphenylphosphine)palladium (0.58 g, 0.50 mmol), potassium acetate (9.81 g, 100.00 mmol), 180 mL toluene, 60 mL ethanol, and 60 mL water were added sequentially to a reaction flask. The mixture was stirred and the reaction system was heated under reflux for 3.5 hours. After the reaction was completed, the mixture was cooled to room temperature, filtered to obtain a filter cake, washed with ethanol, and finally recrystallized from toluene to obtain intermediate H-410 (15.16 g, yield 84%); HPLC purity ≥99.83%. Mass spectrometry m / z: 360.0359 (theoretical value: 360.0376).

[0258] Preparation of compound 410:

[0259] Under nitrogen protection, H-410 (10.83 g, 30.00 mmol), B-410 (12.22 g, 30.00 mmol), Pd2(dba)3 (0.33 g, 0.36 mmol), tri-tert-butylphosphine (1.44 mL of 0.5 M toluene solution, 0.72 mmol), potassium carbonate (6.63 g, 48.00 mmol), and 300 mL of tetrahydrofuran were added sequentially to a reaction flask. The mixture was stirred and the reaction system was heated under reflux for 5 hours. After the reaction was completed, the mixture was cooled to room temperature, filtered to obtain a filter cake, and washed with a small amount of toluene. Finally, the filter cake was recrystallized from toluene to obtain compound 410 (13.27 g, yield 73%), with an HPLC purity ≥99.91%. Mass spectrometry m / z: 605.2720 (theoretical value: 605.2708). Theoretical elemental content (%) C 43 H 19 D 11 OS: C, 85.25; H, 6.82. Measured elemental content (%): C, 85.24; H, 6.83.

[0260] Synthesis Example 28: Preparation of Compound 439

[0261]

[0262] According to the preparation method in Synthesis Example 1, a-8 was replaced with an equimolar amount of a-439, b-8 with an equimolar amount of b-439, A-8 with an equimolar amount of A-439, and B-8 with an equimolar amount of B-439, yielding compound 439 (14.49 g); HPLC purity ≥ 99.94%. Mass spectrometry m / z: 699.3830 (theoretical value: 699.3842). Theoretical elemental content (%) C 49 H 37D7N2O2: C, 84.08; H, 7.34; N, 4.00. Measured elemental content (%): C, 84.07; H, 7.32; N, 4.04.

[0263] Synthesis Example 29: Preparation of Compound 470

[0264]

[0265] According to the preparation method in Synthesis Example 1, a-8 was replaced with an equimolar amount of a-377, b-8 with an equimolar amount of b-377, A-8 with an equimolar amount of A-470, and B-8 with an equimolar amount of B-377, yielding compound 470 (13.05 g); HPLC purity ≥ 99.93%. Mass spectrometry m / z: 587.2581 (theoretical value: 587.2590). Theoretical elemental content (%) C 41 H 21 D7N2O2: C, 83.79; H, 6.00; N, 4.77. Measured elemental content (%): C, 83.77; H, 6.04; N, 4.75.

[0266] Synthesis Example 30: Preparation of Compound 479

[0267]

[0268] According to the preparation method in Example 1, m-8 was replaced with an equimolar amount of m-479, A-8 with an equimolar amount of A-25, and B-8 with an equimolar amount of B-206 to obtain compound 479 (12.74 g); HPLC purity ≥ 99.98%. Mass spectrometry m / z: 581.2446 (theoretical value: 581.2434). Theoretical elemental content (%) C 43 H 27 D3O2: C, 88.78; H, 5.72. Measured elemental content (%): C, 88.75; H, 5.75.

[0269] Synthesis Example 31: Preparation of Compound 494

[0270]

[0271] According to the preparation method in Example 1, m-8 was replaced with an equimolar amount of m-479, A-8 with an equimolar amount of A-25, and B-8 with an equimolar amount of B-494 to obtain compound 494 (13.01 g); HPLC purity ≥ 99.96%. Mass spectrometry m / z: 610.2711 (theoretical value: 610.2700). Theoretical elemental content (%) C 44 H 30D3NO2: C, 86.53; H, 5.94; N, 2.29. Measured elemental content (%): C, 86.57; H, 5.96; N, 2.23.

[0272] Synthesis Example 32: Preparation of Compound 501

[0273]

[0274] According to the preparation method in Example 1, m-8 was replaced with an equimolar amount of m-479, A-8 with an equimolar amount of A-501, and B-8 with an equimolar amount of B-501 to obtain compound 501 (13.65 g); HPLC purity ≥ 99.95%. Mass spectrometry m / z: 649.1779 (theoretical value: 649.1789). Theoretical elemental content (%) C 43 H 25 D3F2S2: C, 79.48; H, 4.81. Measured elemental content (%): C, 79.43; H, 4.86.

[0275] Synthesis Example 33: Preparation of Compound 528

[0276]

[0277] According to the preparation method in Example 1, m-8 was replaced with an equimolar amount of m-479, A-8 with an equimolar amount of A-25, and B-8 with an equimolar amount of B-528 to obtain compound 528 (14.32 g); HPLC purity ≥ 99.97%. Mass spectrometry m / z: 701.3388 (theoretical value: 701.3373). Theoretical elemental content (%) C 52 H 39 D3O2: C, 88.98; H, 6.46. Measured elemental content (%): C, 88.97; H, 6.47.

[0278] [Device Examples]

[0279] The instruments used to test the device performance in this invention consist of a combined IVL testing system comprising testing software, a computer, a Keithley K2400 digital source meter, and a Photo Research PR788 spectral scanning luminance meter. This system was used to test the driving voltage and luminous efficiency of the organic electroluminescent device. The lifetime test employed the McScience M6000 OLED lifetime testing system. The testing conditions were atmospheric conditions, room temperature, and a current density of 10 mA / cm². 2 .

[0280] [Device Example 1]

[0281] First, a transparent conductive ITO glass substrate is used as the anode and 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.

[0282] A 60 nm thick NPNPB layer was vacuum-deposited on an ITO glass substrate as a hole injection layer; an 80 nm thick β-NPB layer was vacuum-deposited on the hole injection layer to form a hole transport layer; compound 8 and H-1, as host materials, were vacuum-deposited on the hole transport layer, with compound 8 accounting for 50 wt% of the total host material, and Ir(ppy)3 was vacuum-deposited as a dopant, with a doping amount of 10 wt% of the total host and dopant, to form a 40 nm thick light-emitting layer; BCP and LiQ were vacuum-deposited on the light-emitting layer at a 1:1 (wt%) ratio to form an electron transport layer with a deposition thickness of 35 nm; a 1 nm thick LiF layer was vacuum-deposited on the electron transport layer as an electron injection layer; and Al (120 nm) was vacuum-deposited on the electron injection layer as a cathode.

[0283]

[0284] [Device Examples 2-15]

[0285] The organic electroluminescent device was prepared by replacing the main material of the light-emitting layer of compound 8 in device example 1 with compounds 45, 49, 94, 110, 114, 168, 196, 206, 318, 356, 377, 479, 494, and 528 of the present invention, respectively. Otherwise, the organic electroluminescent device was prepared by the same preparation method as in device example 1.

[0286] [Comparative Device Examples 1-2]

[0287] Compounds A and B were used to replace compound 47 in device example 1 as the main material of the light-emitting layer. Otherwise, an organic electroluminescent device was prepared by the same preparation method as device example 1.

[0288] The luminescence characteristics test results of devices 1 to 15 in the device embodiments of the present invention and the organic electroluminescent devices obtained in comparative embodiments 1 to 2 are shown in Table 1 below.

[0289] Table 1:

[0290]

[0291]

[0292] As shown in Table 1, when the compound described in this invention is used as the main material of the light-emitting layer of an organic electroluminescent device, the device has a lower driving voltage, higher luminous efficiency, and longer lifespan. The compound described in this invention is a high-performance light-emitting layer main material.

[0293] [Device Example 16]

[0294] First, a transparent conductive ITO glass substrate is used as the anode and 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.

[0295] A 10 nm thick HI-1 layer was vacuum-deposited on an ITO glass substrate as a hole injection layer; a 70 nm thick NPB layer was vacuum-deposited on the hole injection layer to form a hole transport layer; m-CPB was vacuum-deposited on the hole transport layer as the host material, and Ir(Piq)2(acac) was vacuum-deposited as a dopant with a doping amount of 5 wt% of the total host and dopant content to form a 39 nm thick light-emitting layer; compound 25 and LiQ were vacuum-deposited on the light-emitting layer in a 1:1 (wt%) ratio to form an electron transport layer with a deposition thickness of 35 nm; a 1.1 nm thick LiF layer was vacuum-deposited on the electron transport layer as an electron injection layer; and Al (120 nm) was vacuum-deposited on the electron injection layer as a cathode.

[0296]

[0297] [Device Examples 17-31]

[0298] Compounds 49, 94, 110, 134, 160, 175, 191, 286, 298, 318, 356, 377, 410, 470, and 479 of the present invention were used to replace compound 25 in device example 16 as electron transport materials. Otherwise, an organic electroluminescent device was prepared using the same preparation method as in device example 16.

[0299] [Comparative Device Examples 3-4]

[0300] Compounds A and C were used to replace compound 25 in device example 16 as electron transport materials. Otherwise, an organic electroluminescent device was prepared using the same preparation method as device example 16.

[0301] The luminescence characteristics test results of devices 16-31 in the device embodiments of the present invention and the organic electroluminescent devices obtained in comparative embodiments 3-4 are shown in Table 2 below.

[0302] Table 2:

[0303]

[0304] As shown in Table 2, when the compound described in this invention is used as an electron transport material for organic electroluminescent devices, the device exhibits a lower driving voltage, higher luminous efficiency, and longer lifespan. The compound described in this invention is a high-performance electron transport material.

[0305] [Device Example 32]

[0306] First, a transparent conductive ITO glass substrate is used as the anode and 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.

[0307] A 10 nm thick HI-1 layer was vacuum-deposited on an ITO glass substrate as a hole injection layer; a 60 nm thick HT-1 layer was vacuum-deposited on the hole injection layer to form a hole transport layer; CDBP was vacuum-deposited on the hole transport layer as the host material, and Ir(mppy)3 was vacuum-deposited as a dopant at a doping amount of 5 wt% of the total host and dopant, forming a 37 nm thick light-emitting layer; compound 34 was vacuum-deposited on the light-emitting layer to form a hole blocking layer with a thickness of 30 nm; BCP and LiQ were vacuum-deposited on the hole blocking layer at a 1:1 (wt%) ratio to form an electron transport layer with a thickness of 35 nm; LiF with a thickness of 1.1 nm was vacuum-deposited on the electron transport layer as an electron injection layer; and Al (120 nm) was vacuum-deposited on the electron injection layer as a cathode.

[0308]

[0309] [Device Examples 33-47]

[0310] Compounds 49, 94, 110, 125, 150, 182, 259, 318, 323, 356, 371, 377, 439, 479, and 501 were used to replace compound 34 in device example 32 as hole blocking materials. Otherwise, an organic electroluminescent device was prepared using the same preparation method as in device example 32.

[0311] [Comparative Device Examples 5-6]

[0312] Compounds D and B were used to replace compound 34 in device example 32 as hole blocking materials. Otherwise, an organic electroluminescent device was prepared using the same preparation method as device example 32.

[0313] The luminescence characteristics test results of devices 32-47 in the device embodiments of the present invention and the organic electroluminescent devices obtained in comparative embodiments 5-6 are shown in Table 3 below.

[0314] Table 3:

[0315]

[0316]

[0317] As shown in Table 3, when the compound described in this invention is used as a hole blocking material in organic electroluminescent devices, the devices have lower driving voltage, higher luminous efficiency, and longer lifespan. The compound described in this invention is a high-performance hole blocking material.

[0318] It should be noted that the present invention has been specifically described with reference to specific embodiments. For those skilled in the art, various improvements and modifications can be made to the present invention without departing from the principle of the present invention, and these improvements and modifications also fall within the protection scope of the present invention.

Claims

1. A compound containing a fluorene group, characterized in that, The compound containing the fluorene group is selected from any one of the structures shown below. Wherein, Ar1 and Ar2 are independently selected from the following formula a; Indicated as a connection site; The formula 'a' is selected from any of the structures shown below. The same or different R3 is selected from any one of hydrogen, deuterium, tritium, halogen, cyano, substituted or unsubstituted C1 to C6 alkyl groups; The n1 that is the same or different is selected from 1, 2, 3 or 4; the n2 that is the same or different is selected from 1, 2 or 3; the n4 that is the same or different is selected from 1, 2, 3, 4, 5 or 6; Rx is selected from any one of hydrogen, deuterium, tritium, halogen, cyano, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted phenyl, and pyridyl; m is selected from 1 or 2; The Choose any one of the structures shown below. The Rm that is the same or different is selected from any one of hydrogen, deuterium, tritium, substituted or unsubstituted C1-C6 alkyl, phenyl, pyridyl groups; The same R4 is selected from hydrogen; The a3 that is the same or different is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the a4 that is the same or different is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; the a5 that is the same or different is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12; the a6 that is the same or different is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 or 14; The same or different b1 is selected from 1, 2, 3, 4, 5, 6 or 7; the same or different b3 is selected from 1, 2, 3, 4, 5, 6, 7, 8 or 9; the same or different b8 is selected from 1, 2, 3, 4, 5 or 6; R0 is selected from any one of hydrogen, deuterium, tritium, halogen, cyano, substituted or unsubstituted C1-C6 alkyl groups; v is selected from 1, 2 or 3; The L is selected from any one of the following: single bond, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted anthraceneylene, substituted or unsubstituted phenanthylene, substituted or unsubstituted fluoreneylene, substituted or unsubstituted pyridylene, substituted or unsubstituted pyrimidinylene, substituted or unsubstituted dibenzofuranylene, and substituted or unsubstituted dibenzothiopheneylene. L1 and L2 are independently selected from any one of a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted naphthylene, or a substituted or unsubstituted pyridylene; The substituents in the substituted or unsubstituted C1-C6 alkyl group are independently selected from fluorine, chlorine, bromine, and iodine. The substituent in "substituted or unsubstituted" of the following is independently selected from deuterium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, and tert-butyl. The compound satisfies at least one of the following conditions: i. The v is selected from 3, and the R0 is selected from deuterium; ii. b1 is selected from 7, b3 is selected from 9, b8 is selected from 6, and Rm is selected from deuterium; iii. n1 is selected from 4, n2 is selected from 3, n4 is selected from 6, and R3 is selected from deuterium; iv. The Rx is selected from pentadeuterated phenyl; v. L is selected from a single bond or any of the groups shown below. c1 is selected from 4; c2 is selected from 8; c3 is selected from 6; c6 is selected from 3; vi. L1 or L2 is selected from any one of the following groups. c1 is selected from 4; c2 is selected from 8; c3 is selected from 6; c6 is selected from 3.

2. The compound containing a fluorene group according to claim 1, characterized in that, The Choose any one of the structures shown below. The Rm, whether the same or different, is selected from any one of hydrogen, deuterium, tritium, substituted or unsubstituted C1-C6 alkyl groups.

3. The compound containing a fluorene group according to claim 1, characterized in that, The formula 'a' is selected from any of the structures shown below. 。 4. The compound containing a fluorene group according to claim 1, characterized in that, At least one of L, L1, and L2 contains a plurality of deuterium.

5. The compound containing a fluorene group according to claim 1, characterized in that, The L is selected from a single bond or any of the following groups: L1 and L2 are selected from single bonds or any of the following groups. 。 6. A compound containing a fluorene group, characterized in that, The compound containing the fluorene group is selected from any of the structures shown below. 。 7. An organic electroluminescent device, comprising an anode, a cathode, and an organic layer located between the anode and the cathode, characterized in that, The organic layer comprises the compound containing a fluorene group as described in any one of claims 1 to 6.

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

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