Organic compound, organic electroluminescent material and application thereof

Abstract

The invention provides an organic compound, an organic electroluminescent material and application thereof, the organic compound has a structure as shown in a formula IA or a formula IB, through the design of a molecular structure, the organic compound has a specific spatial configuration, the overall plane conjugacy of the molecular structure is better, electrons and holes can be effectively transmitted and injected, and the organic electroluminescent material can be applied to the field of organic electroluminescent devices. And excellent carrier mobility and photoelectric properties are shown. The organic compound is used for the organic electroluminescent device, is especially suitable for being used as a main body material, has excellent carrier transmission performance, is beneficial to exciton energy transmission between the main body material and a dye, and can effectively improve the luminous efficiency of the device, reduce the driving voltage and prolong the service life, so that the device has better comprehensive performance; and the requirements of the current panel and display manufacturing industry on high-performance organic materials are met.

Description

Technical Field

[0001] The invention belongs to the technical field of organic electroluminescence, and specifically relates to an organic compound, an organic electroluminescent material and applications thereof. Background Art

[0002] Organic Light Emission Diode (OLED) is a device with a sandwich-like structure, including positive and negative electrode film layers and organic functional material layers sandwiched between the positive and negative electrode film layers. Voltage is applied to the positive and negative electrodes of the OLED device, positive charges are injected from the positive electrode, and negative charges are injected from the negative electrode. Under the action of the electric field, the positive and negative charges migrate in the organic layer and meet to combine and emit light. Due to the advantages of high brightness, fast response, wide viewing angle, simple process, and flexibility, OLED devices have attracted much attention in the fields of new display technology and new lighting technology. At present, this technology has been widely used in display panels of new lighting fixtures, smart phones, tablet computers and other products, and will further expand to the application fields of large-size display products such as televisions. It is a new display technology with fast development and high technical requirements.

[0003] As OLED continues to advance in the two major fields of lighting and display, people are paying more attention to the research on its core functional organic materials. This is because an OLED device with good efficiency and long life is usually the result of an optimized combination of device structure and various functional organic materials, which provides great opportunities and challenges for researchers to design and develop functional materials of various structures. Common functional organic materials include: hole injection materials, hole transport materials, hole blocking materials, electron injection materials, electron transport materials, electron blocking materials, luminescent host materials and luminescent guests (dyes), etc.

[0004] In order to prepare OLED light-emitting devices with lower driving voltage, better luminous efficiency and longer device life, and to continuously improve the performance of OLED devices, it is necessary not only to innovate the structure and manufacturing process of OLED devices, but also to continuously study and innovate the optoelectronic functional materials in OLED devices to prepare functional materials with higher performance. Based on this, the OLED material industry has been committed to developing new organic electroluminescent materials to achieve low starting voltage, high luminous efficiency and better device life. In recent years, people in the industry have continuously tried and explored ways to improve device efficiency and stability. Among them, seeking new materials to improve device performance is the most common way. A large number of novel materials have been developed for use in organic electroluminescent devices. Although it has a certain improvement in device performance, it still has a large amount of carrier accumulation at the interface, and there is also the problem of low device efficiency.

[0005] Therefore, the field is in urgent need of developing organic electroluminescent devices with higher performance, and further developing organic electroluminescent materials, especially host materials, that can provide better photoelectric performance is the direction in which the industry continues to strive for breakthroughs. Summary of the invention

[0006] In view of the deficiencies in the prior art, the purpose of the present invention is to provide an organic compound, an organic electroluminescent material and their applications. Through the design of the molecular structure, the organic compound has excellent photoelectric properties and carrier transport properties. Its application in organic electroluminescent devices can effectively improve the life and efficiency of the devices and reduce the driving voltage.

[0007] To achieve this object, the present invention adopts the following technical solutions:

[0008] In a first aspect, the present invention provides an organic compound having a structure as shown in Formula IA or Formula IB:

[0009]

[0010] In Formula IA and Formula IB, X is O or S.

[0011] In Formula IA and Formula IB, Y is selected from O, S, CR 11 R 12 or NR 13 Any one of .

[0012] R 11 , R 12 , R 13 are each independently selected from any one of substituted or unsubstituted C1-C20 straight or branched alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C3-C20 cycloalkyl; the R 11 and R 12 Not connected or connected to form a ring through chemical bonds.

[0013] In Formula IA and Formula IB, Ar is selected from any one of a substituted or unsubstituted C6-C60 aryl group and a substituted or unsubstituted C3-C60 heteroaryl group;

[0014] In Formula IA and Formula IB, R, R', R1, and R2 are each independently selected from any one of halogen, cyano, substituted or unsubstituted C1-C20 straight or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C3-C30 heteroaryl, and substituted or unsubstituted C6-C30 aryl;

[0015] In Formula IA, a and b represent the number of substituents R and R' respectively, a is selected from an integer of 0-6, for example, 0, 1, 2, 3, 4, 5 or 6; b is selected from an integer of 0-3, for example, 0, 1, 2 or 3.

[0016] In formula IB, c and d represent the number of substituents R and R' respectively, c is selected from an integer of 0-4, for example, 0, 1, 2, 3 or 4; d is selected from an integer of 0-5, for example, 0, 1, 2, 3, 4 or 5.

[0017] In Formula IA and Formula IB, m1 and m2 represent the number of substituents R1 and R2 respectively, m1 is selected from an integer of 0-6, for example, it can be 0, 1, 2, 3, 4, 5 or 6; m2 is selected from an integer of 0-7, for example, it can be 0, 1, 2, 3, 4, 5, 6 or 7.

[0018] When a≥2, multiple (at least 2) R are the same or different groups; when b≥2, multiple (at least 2) R' are the same or different groups; c, d, m1 and m2 are the same, and for the sake of brevity, they are not repeated.

[0019] R 11 , R 12 , R 13 , Ar, R, R', R1, and R2 are each independently selected from any one of halogen, cyano, nitro, hydroxyl, amino, aldehyde, ester, C1-C20 straight or branched alkyl, C1-C20 alkoxy, C2-C10 alkenyl, C3-C20 cycloalkyl, C2-C20 heterocycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl, or a combination of at least two thereof; the substituted substituents are each independently not connected to the adjacent ring structure or are connected to form a ring through chemical bonds.

[0020] In the present invention, "the substituted substituents are each independently not connected to the adjacent ring structure" means that the substituent is only connected to the C atom through a single bond; "the substituted substituents are each independently connected to the adjacent ring structure through a chemical bond to form a ring" means that the substituent is connected to the C atom through a chemical bond and is also connected to the adjacent ring through a chemical bond, thereby forming a fused ring structure. When the same description is involved below, it has the same meaning and will not be repeated one by one.

[0021] In the present invention, the "substituted or unsubstituted" group may be substituted with one substituent or with multiple substituents. When there are multiple substituents (at least 2), they may be the same or different substituents. When the same expressions are mentioned below, they have the same meaning. Unless otherwise specified, the selection range of the substituted substituents is as shown above and will not be repeated.

[0022] The molecular structure of the organic compound provided by the present invention is shown in Formula IA or Formula IB, and the triazine structural unit and the O- / S-containing fused ring structure (the fused ring structure where X is located) are connected in a specific manner with a naphthyl bridge structure, so that the organic compound has a specific spatial configuration, and the overall planar conjugation of the molecular structure is better, and electrons and holes can be effectively transmitted and injected, showing excellent carrier mobility and photoelectric properties. The organic compound is used for organic electroluminescent devices, and is particularly suitable as a host material, has excellent carrier transport performance, and is conducive to the exciton energy transmission between the host material and the dye (dopant material), which plays a role in reducing the device voltage, improving the current efficiency, and extending the device life.

[0023] It should be noted that, for the sake of convenience, the present invention describes the possible effects of each group / feature of the organic compound separately, but this does not mean that these groups / features act in isolation. In fact, the reason for obtaining good performance is essentially the optimized design of the entire molecular structure, which is the result of the synergistic effect of each group, rather than the effect of a single group.

[0024] The following are preferred technical solutions of the present invention, but are not intended to limit the technical solutions provided by the present invention. Through the following preferred technical solutions, the objectives and beneficial effects of the present invention can be better achieved and realized.

[0025] In the present invention, the halogen may be fluorine, chlorine, bromine or iodine. The following descriptions involving the same have the same meaning.

[0026] In the present invention, the expression of chemical elements, unless otherwise specified, includes the concept of isotopes with the same chemical properties. For example, hydrogen (H) includes 1 H (hydrogen), 2 H (deuterium, D), 3 H (tritium, T), etc.; carbon (C) includes 12 C. 13 C, etc.

[0027] In the present invention, unless otherwise specified, the heteroatom of the heteroaryl group is selected from N, O, S, P, B, Si or Se, preferably N, O or S.

[0028] In the present invention, the expression of a ring structure crossed by “—” indicates that the connection site is at any position on the ring structure that can form a bond.

[0029] In the present invention, "-*" and "*" both represent the bonding site of a group.

[0030] In the present invention, the expression of Ca-Cb means that the number of carbon atoms in the group is ab. Unless otherwise specified, the number of carbon atoms does not include the number of carbon atoms in the substituent.

[0031] In the present invention, “each independently” means that when there are multiple subjects, they may be the same as or different from each other.

[0032] In the present invention, the C6-C60 can be C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, ​​C48, C50, C52, C54, C56 or C58, etc.

[0033] The C3-C60 can all be C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, ​​C48, C50, C52, C54, C56 or C58, etc.

[0034] The C6-C30 can all be C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.

[0035] The C3-C30 can all be C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.

[0036] The C1-C20 can all be C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17 or C18, etc.

[0037] The C3-C20 can all be C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17 or C18, etc.

[0038] The C2-C20 can all be C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17 or C18, etc.

[0039] The C1-C30 can all be C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C20, C22, C24, C26 or C28, etc.

[0040] The C2-C30 can all be C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C20, C22, C24, C26 or C28, etc.

[0041] The C2-C10 can all be C3, C4, C5, C6, C7, C8, C9, etc.

[0042] In the present invention, the C6-C60 aryl group, C6-C30 aryl group, preferably C6-C20 aryl group, includes a monocyclic aryl group and a condensed ring aryl group; the monocyclic aryl group means that the group contains at least one phenyl group, and when it contains at least two phenyl groups, the phenyl groups are connected by a single bond, and exemplary examples include but are not limited to: phenyl, biphenyl, terphenyl, quadriphenyl, etc. The fused ring aromatic group means a group containing at least two aromatic rings, and the aromatic rings share two adjacent carbon atoms and are fused to each other, including, but not limited to, naphthyl (1-naphthyl, 2-naphthyl), anthracenyl (1-anthracenyl, 2-anthracenyl, 9-anthracenyl), phenanthrenyl, indenyl, fluorenyl and its derivatives (9,9-dimethylfluorenyl, 9,9-diethylfluorenyl, 9,9-dipropylfluorenyl, 9,9-dibutylfluorenyl, 9,9-dipentylfluorenyl, 9,9-dihexylfluorenyl, 9,9-diphenylfluorenyl, 9,9-dinaphthylfluorenyl, phenylmethylfluorenyl, spirobifluorenyl, benzofluorenyl, etc.), fluoranthenyl, triphenylene, pyrenyl (1-pyrenyl, 2-pyrenyl, 4-pyrenyl), peryl, It should be noted that the monocyclic aromatic group and the condensed aromatic group connected by a single bond also belong to the scope of aromatic group, such as phenylnaphthyl, naphthylphenyl, etc.

[0043] The C3-C60 heteroaryl, C3-C30 heteroaryl, preferably C3-C20 heteroaryl, includes a monocyclic heteroaryl or a condensed ring heteroaryl. The monocyclic heteroaryl means that the molecule contains at least one heteroaryl. When the molecule contains a heteroaryl and other groups (such as aryl, heteroaryl, etc.), the heteroaryl and other groups are connected by a single bond, including but not limited to pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, thienyl, pyrrolyl, bipyridyl, phenylpyridyl, pyridylphenyl, pyrimidinylphenyl, etc. The fused ring heteroaryl group means a group containing at least one aromatic heterocycle and one aromatic ring (aromatic heterocycle or aromatic ring) in the molecule, and the two share two adjacent atoms that are fused to each other, including, but not limited to, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiophenyl, isobenzofuranyl, isobenzothiophenyl, indolyl, dibenzofuranyl, dibenzothiophenyl, naphthiobenzofuranyl, naphthiobenzothiophenyl, carbazolyl and its derivatives (N-phenylcarbazolyl, N-naphthylcarbazolyl, benzocarbazolyl, dibenzocarbazolyl, indolcarbazolyl, azacarbazolyl, etc.), acridinyl, phenothiazinyl, phenoxazinyl, hydroacridinyl, etc. It should be noted that heteroaryl and heteroaryl groups connected by a single bond, and aryl and heteroaryl groups connected by a single bond also fall within the scope of heteroaryl groups, for example, phenyldibenzofuranyl, phenyldibenzothienyl, and the like.

[0044] Specific examples of the C6-C30 arylene group include divalent groups obtained by removing a hydrogen atom from the above-mentioned aryl groups; specific examples of the C3-C30 heteroarylene group include divalent groups obtained by removing a hydrogen atom from the above-mentioned heteroaryl groups.

[0045] The C1-C30 straight chain or branched alkyl group, C1-C20 straight chain or branched alkyl group, preferably C1-C10 straight chain or branched alkyl group, illustratively include but are not limited to: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, 2-methylbutyl, n-pentyl, isopentyl, neopentyl, n-hexyl, neohexyl, 2-ethylhexyl, n-octyl, n-heptyl, n-nonyl, n-decyl and the like.

[0046] Specific examples of the C1-C30 alkoxy group and the C1-C20 alkoxy group include monovalent groups obtained by connecting the above-mentioned linear or branched alkyl groups to O.

[0047] The C2-C30 alkenyl, C2-C20 alkenyl, preferably C2-C10 alkenyl, contains at least one C=C, illustratively including but not limited to: vinyl, propenyl, allyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, butadienyl, pentadienyl and the like.

[0048] The C3-C30 cycloalkyl group, C3-C20 cycloalkyl group, preferably C3-C10 cycloalkyl group, includes a monocyclic alkyl group or a polycyclic alkyl group. A monocyclic alkyl group refers to an alkyl group containing a single cyclic structure, and a polycyclic alkyl group refers to a structure composed of two or more cycloalkyl groups sharing one or more carbon atoms on the ring; examples include but are not limited to: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, etc.

[0049] Specific examples of the C2-C20 heterocycloalkyl group include groups formed by replacing at least one C atom in the aforementioned cycloalkyl group with a heteroatom (such as N, O, S, etc.), including but not limited to: epoxy, oxetanyl, tetrahydrofuranyl, tetrahydrothiophenyl, tetrahydropyrrolyl, tetrahydropyranyl, piperidinyl, piperazinyl, dioxane, morpholinyl, etc.

[0050] A specific example of the C1-C30 alkylsilyl group is a monovalent group formed by replacing at least one H on -SiH3 with the linear or branched alkyl group listed above. A specific example of the C6-C30 arylsilyl group is a monovalent group formed by replacing at least one H on -SiH3 with the aryl group listed above. A specific example of the C1-C30 alkylC6-C30 arylsilyl group is a monovalent group formed by replacing at least one H on -SiH3 with the linear or branched alkyl group listed above and at least one H with the aryl group listed above, which may be a di(C1-C30 alkyl)(C6-C30 aryl)silyl group or a (C1-C30 alkyl)di(C6-C30 aryl)silyl group.

[0051] A specific example of the C1-C30 alkylamino group is a monovalent group formed by replacing at least one H on -NH2 with the above-listed straight-chain or branched alkyl group. A specific example of the C2-C30 alkenylamino group is a monovalent group formed by replacing at least one H on -NH2 with the above-listed alkenyl group. A specific example of the C1-C30 alkyl C2-C30 alkenylamino group is a monovalent group formed by replacing at least one H on -NH2 with the above-listed straight-chain or branched alkyl group and at least one H with the above-listed alkenyl group.

[0052] The C6-C30 arylamino group is a monovalent group formed by replacing at least one H on -NH2 with the above-listed aryl group. The C3-C30 heteroarylamino group is a monovalent group formed by replacing at least one H on -NH2 with the above-listed heteroaryl group. The C6-C30 arylC3-C30 heteroarylamino group is a monovalent group formed by replacing at least one H on -NH2 with the above-listed aryl group and at least one H with the above-listed heteroaryl group.

[0053] Preferably, m1 and m2 are both zero.

[0054] Preferably, the organic compound has a structure as shown in any one of Formula IA-1, Formula IA-2, Formula IB-1, Formula IB-2, Formula IB-3, Formula IB-4, Formula IB-5, Formula IB-6, and Formula IB-7:

[0055]

[0056] Wherein, X, Y, Ar, R, R', a, b, c, and d have the same limited ranges as those of Formula IA and Formula IB.

[0057] Preferably, Y is O or S.

[0058] Preferably, the R 11 , R 12 , R 13 Each is independently selected from any one of C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight chain or branched alkyl, C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16 or C18, etc.) aryl, and further preferably any one of C1-C6 straight chain or branched alkyl, phenyl, naphthyl, biphenyl.

[0059] Preferably, Ar is selected from any one of a substituted or unsubstituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16 or C18, etc.) aryl group, and a substituted or unsubstituted C3-C20 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16 or C18, etc.) heteroaryl group.

[0060] Preferably, Ar is selected from any one of the following substituted or unsubstituted groups:

[0061] -* represents the attachment site of the group.

[0062] Wherein, Z is selected from O, S, CR 21 R 22 or NR 23 Any one of .

[0063] R 21 , R 22 , R 23 Each is independently selected from any one or a combination of at least two of a C1-C20 straight or branched alkyl group, a C6-C30 aryl group, a C3-C30 heteroaryl group, a C2-C10 alkenyl group, and a C3-C20 cycloalkyl group; 21 and R22 Not connected or connected to form a ring through chemical bonds.

[0064] The substituents substituted in Ar have the same limitations as described above.

[0065] Preferably, Z is O or S.

[0066] Preferably, the R 21 , R 22 , R 23 Each is independently selected from any one of C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight chain or branched alkyl, C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16 or C18, etc.) aryl, and further preferably any one of C1-C6 straight chain or branched alkyl, phenyl, naphthyl, biphenyl.

[0067] Preferably, Ar is selected from Or any one of; -* represents the connection site of the group.

[0068] Preferably, R and R' are each independently selected from any one of halogen, cyano, substituted or unsubstituted C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) linear or branched alkyl, substituted or unsubstituted C3-C10 (e.g., C4, C5, C6, C7, C8, C9, etc.) cycloalkyl, substituted or unsubstituted C3-C20 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16 or C18, etc.) heteroaryl, substituted or unsubstituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16 or C18, etc.) aryl, preferably any one of phenyl, naphthyl, biphenyl, terphenyl, phenylnaphthyl, naphthylphenyl.

[0069] Preferably, a, b, c, and d are each independently selected from 0 or 1.

[0070] Preferably, the organic compound has a structure shown in any one of the following N1-N125:

[0071]

[0072]

[0073]

[0074]

[0075]

[0076]

[0077]

[0078] In a second aspect, the present invention provides a use of the organic compound as described in the first aspect, wherein the organic compound is applied to an organic electronic device.

[0079] Preferably, the organic electronic device includes an organic electroluminescent device, an optical sensor, a solar cell, a lighting element, an organic thin film transistor, an organic field effect transistor, an organic thin film solar cell, an information tag, an electronic artificial skin sheet, a sheet-type scanner or electronic paper.

[0080] Preferably, the organic compound is applied to an organic electroluminescent device.

[0081] Preferably, the organic compound is used as a light-emitting layer material in an organic electroluminescent device.

[0082] Preferably, the organic compound is used as a host material of a light-emitting layer in an organic electroluminescent device, and more preferably as a host material of a red light-emitting layer.

[0083] Preferably, the organic compound is used as an N-type (electronic type) host material, and more preferably an N-type red light host material.

[0084] The organic compound of the present invention, as a light-emitting layer material, especially as a red light host material, has good light-emitting performance and is beneficial to improving the light-emitting efficiency of the device.

[0085] Preferably, the organic compound can also be used as a hole blocking material or an electron transporting material of an organic electroluminescent device.

[0086] In a third aspect, the present invention provides an organic electroluminescent material, comprising a combination of a first compound and a second compound; the first compound is the organic compound as described in the first aspect, and the second compound is an aromatic amine compound.

[0087] In the present invention, the organic compound having the structure shown in Formula IA or Formula IB is used as the first compound, which can achieve rapid injection and transfer of electrons while taking into account hole transport, and has excellent electron injection and transport performance and suitable hole transport performance; the second compound has excellent hole injection and transport performance and high hole mobility. It is compounded with the first compound so that the organic electroluminescent material is used in an organic electroluminescent device and can be used as a dual host material in the light-emitting layer, so as to regulate the injection / transport balance of holes and electrons, promote the transport balance of carriers, and is more conducive to the position of the electron and hole recombination center in the light-emitting layer occurring at the center of the light-emitting layer, avoiding a large amount of carrier accumulation at the interface, and improving the transmission and utilization rate of excitons, thereby significantly improving the luminous efficiency and life of the device and reducing the driving voltage of the device.

[0088] Preferably, the second compound has a structure as shown in Formula II:

[0089]

[0090] In Formula II, Ar1 is selected from any one of a substituted or unsubstituted C6-C30 aryl group and a substituted or unsubstituted C3-C30 heteroaryl group.

[0091] The substituents substituted in Ar1 are each independently selected from any one of halogen, cyano, nitro, hydroxyl, amino, aldehyde, ester, unsubstituted or R" substituted C1-C20 straight or branched alkyl, unsubstituted or R" substituted C3-C20 cycloalkyl, unsubstituted or R" substituted C1-C20 alkoxy, unsubstituted or R" substituted C2-C20 alkenyl, unsubstituted or R" substituted C6-C30 aryl, and unsubstituted or R" substituted C3-C30 heteroaryl; the substituents substituted in Ar1 are each independently not connected to the adjacent ring structure or are connected to form a ring by chemical bonds.

[0092] In Formula II, L is selected from any one of a single bond, a substituted or unsubstituted C6-C30 arylene group, and a substituted or unsubstituted C3-C30 heteroarylene group; when L is a single bond, Ar1 is directly connected to the N atom in Formula II through a single bond.

[0093] In formula II, R3 and R4 are each independently selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C1-C30 straight or branched alkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C1-C30 alkylsilyl, substituted or unsubstituted C6-C30 arylsilyl, substituted or unsubstituted C1-C30 alkylC6-C30 arylsilyl, substituted or unsubstituted C1-C30 alkylamino, substituted or unsubstituted C2-C30 alkenylamino , substituted or unsubstituted C1-C30 alkyl C2-C30 alkenylamino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C1-C30 alkyl C6-C30 arylamino, substituted or unsubstituted C2-C30 alkenyl C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C1-C30 alkyl C3-C30 heteroarylamino, substituted or unsubstituted C2-C30 alkenyl C3-C30 heteroarylamino, any one of substituted or unsubstituted C6-C30 aryl C3-C30 heteroarylamino.

[0094] The substituted substituents and R" in L, R3 and R4 are each independently selected from any one or a combination of at least two of halogen, cyano, nitro, hydroxyl, amino, aldehyde, ester, C1-C20 straight or branched alkyl, C1-C20 alkoxy, C2-C10 alkenyl, C3-C20 cycloalkyl, C2-C20 heterocycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl; the substituted substituents and R" in L, R3 and R4 are each independently not connected to the adjacent ring structure or are connected to form a ring through chemical bonds.

[0095] Preferably, Ar1 has a structure as shown in any one of Formula A1, Formula A2 and Formula A3:

[0096]

[0097] Wherein, -* represents the attachment site of the group.

[0098] In formula A1, R A1 , R A2 , R A3 , R A4 , R A5 , R A6 , R A7 , R A8Each is independently selected from any one of hydrogen, halogen, cyano, unsubstituted or R" substituted C1-C20 straight or branched alkyl, unsubstituted or R" substituted C3-C20 cycloalkyl, unsubstituted or R" substituted C1-C20 alkoxy, unsubstituted or R" substituted C3-C30 heteroaryl, and unsubstituted or R" substituted C6-C30 aryl.

[0099] The R A1 , R A2 , R A3 , R A4 Any two adjacent groups are not connected, but are connected by chemical bonds to form a ring A1 or Ring A2 Ring A2 can be understood as a substituted or unsubstituted benzene ring structure.

[0100] In ring A1, X A , Y A Each independently selected from a single bond, O, S, NR 31 or CR 32 R 33 Any one of the above, and the X A and Y A When X A and Y A When none of X is a single bond, the ring A1 comprises a ring structure formed by condensing a benzene ring and a six-membered ring; when X A and Y A When one of the rings is a single bond, the ring A1 includes a ring structure in which a benzene ring and a five-membered ring are condensed.

[0101] R 31 , R 32 , R 33 Each is independently selected from any one of unsubstituted or R"-substituted C1-C20 straight or branched alkyl, unsubstituted or R"-substituted C3-C20 cycloalkyl, unsubstituted or R"-substituted C2-C20 alkenyl, unsubstituted or R"-substituted C3-C30 heteroaryl, and unsubstituted or R"-substituted C6-C30 aryl; the R 32 and R 33 They are not connected or connected to form a ring through chemical bonds.

[0102] R A9 , R A10 , R A11 , R A12 Each is independently selected from any one of hydrogen, halogen, unsubstituted or R"-substituted C1-C20 straight or branched alkyl, unsubstituted or R"-substituted C3-C20 cycloalkyl, unsubstituted or R"-substituted C1-C20 alkoxy, unsubstituted or R"-substituted C3-C30 heteroaryl, and unsubstituted or R"-substituted C6-C30 aryl.

[0103] The R A1 , R A2 , R A3 , R A4 , R A5 , R A6 , R A7 , R A8 , R A9 , R A10 , R A11 , R A12 In the above, except for the groups forming ring A1 and ring A2, any two adjacent groups in other groups are not connected or are connected by a chemical bond to form a ring.

[0104] In formula A2 and formula A3, Y1 is selected from O, S or NR Y1 Any one of .

[0105] R Y1 Any one selected from unsubstituted or R"-substituted C1-C20 straight or branched alkyl, unsubstituted or R"-substituted C3-C20 cycloalkyl, unsubstituted or R"-substituted C2-C20 alkenyl, unsubstituted or R"-substituted C3-C30 heteroaryl, and unsubstituted or R"-substituted C6-C30 aryl.

[0106] In formula A2 and formula A3, R B1 Any one selected from hydrogen, halogen, cyano, unsubstituted or R" substituted C1-C20 straight or branched alkyl, unsubstituted or R" substituted C3-C20 cycloalkyl, unsubstituted or R" substituted C1-C20 alkoxy, unsubstituted or R" substituted C3-C30 heteroaryl, unsubstituted or R" substituted C6-C30 aryl.

[0107] Preferably, in ring A1, the X A Selected from O, S, NR 31 or CR 32 R 33 Any one of the above, the Y A is a single bond, that is, ring A1 is

[0108] Preferably, Ar1 is selected from any one of the following groups a to l:

[0109]

[0110] Wherein, -* represents the attachment site of the group.

[0111] X A Selected from O, S, NR 31 or CR32 R 33 Any one of R 31 , R 32 , R 33 The same limitations as above apply.

[0112] R A1 , R A2 , R A3 , R A4 , R A5 , R A6 , R A7 , R A8 , R A9 , R A10 , R A11 , R A12 Each is independently selected from any one of hydrogen, halogen, unsubstituted or R"-substituted C1-C20 straight or branched alkyl, unsubstituted or R"-substituted C3-C20 cycloalkyl, unsubstituted or R"-substituted C1-C20 alkoxy, unsubstituted or R"-substituted C3-C30 heteroaryl, and unsubstituted or R"-substituted C6-C30 aryl.

[0113] The R A1 , R A2 , R A3 , R A4 , R A5 , R A6 , R A7 , R A8 , R A9 , R A10 , R A11 , R A12 Any two adjacent groups are not connected or connected by chemical bonds to form a ring.

[0114] Y1 and R B1 It has the same limited range as Formula A2 and Formula A3.

[0115] Preferably, in groups a to f, the R A1 , R A2 , R A3 , R A4 , R A5 , R A6 , R A7 , R A8 , R A9 , R A10 , R A11 , R A12 Any two adjacent groups in the ring are not connected or connected by chemical bonds to form a benzene ring.

[0116] Preferably, Ar1 is selected from any one of group a, group b, group c, group d, group i, group j and group l.

[0117] Preferably, Ar1 is selected from any one of the following substituted or unsubstituted groups:

[0118]

[0119] Wherein, -* represents the attachment site of the group.

[0120] X A Selected from O, S, NR 31 or CR 32 R 33 Any one of .

[0121] R 31 , R 32 , R 33 Each is independently selected from any one of unsubstituted or R"-substituted C1-C20 straight or branched alkyl, unsubstituted or R"-substituted C3-C20 cycloalkyl, unsubstituted or R"-substituted C2-C20 alkenyl, unsubstituted or R"-substituted C3-C30 heteroaryl, and unsubstituted or R"-substituted C6-C30 aryl; the R 32 and R 33 They are not connected or connected to form a ring through chemical bonds.

[0122] The substituents substituted in Ar1 have the same limitations as described above.

[0123] Preferably, the R 31 , R 32 , R 33 Each is independently selected from any one of C1-C10 (for example, C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight chain or branched alkyl, C6-C20 (for example, C6, C9, C10, C12, C14, C15, C16 or C18, etc.) aryl, further preferably any one of C1-C6 straight chain or branched alkyl, phenyl, naphthyl, biphenyl, terphenyl, phenylnaphthyl, naphthylphenyl, further preferably methyl or phenyl.

[0124] Preferably, the substituted substituent in Ar1 is selected from any one of unsubstituted or R"-substituted C1-C6 (e.g., C2, C3, C4, C5, etc.) straight or branched alkyl, unsubstituted or R"-substituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, etc.) aryl, and unsubstituted or R"-substituted C3-C20 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, etc.) heteroaryl, and further preferably any one of phenyl, biphenyl, terphenyl, naphthyl, phenylnaphthyl, and naphthylphenyl.

[0125] Preferably, R3 and R4 are each independently selected from any one of a substituted or unsubstituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16 or C18, etc.) aryl group, and a substituted or unsubstituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16 or C18, etc.) heteroaryl group.

[0126] Preferably, R3 and R4 are each independently selected from any one of the following substituted or unsubstituted groups:

[0127]

[0128] Wherein, -* represents the attachment site of the group.

[0129] Z1 is selected from O, S, NR 41 or CR 42 R 43 Any one of .

[0130] R 41 , R 42 , R 43 Each is independently selected from any one or a combination of at least two of a C1-C20 straight or branched alkyl group, a C6-C30 aryl group, a C3-C30 heteroaryl group, a C2-C10 alkenyl group, and a C3-C20 cycloalkyl group; 42 and R 43 Not connected or connected to form a ring through chemical bonds.

[0131] Preferably, the second compound has a structure as shown in Formula IIA or Formula IIB:

[0132]

[0133] Among them, R A1 , R A2 , R A3 , R A4 , R A5, R A6 , R A7 , R A8 It has the same definition as in formula A1, L, R3, and R4 have the same definition as in formula II; and Z1 has the same definition as described above.

[0134] Preferably, the R 41 , R 42 , R 43 Each is independently selected from any one of C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight chain or branched alkyl, C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16 or C18, etc.) aryl, and further preferably any one of C1-C6 straight chain or branched alkyl, phenyl, naphthyl, biphenyl.

[0135] Preferably, R3 and R4 are each independently selected from any one of the following groups:

[0136] -* represents the attachment site of the group.

[0137] Preferably, L is selected from any one of the following groups which are single bonds, substituted or unsubstituted:

[0138] -* represents the attachment site of the group.

[0139] Z2 is selected from O, S, NR 51 or CR 52 R 53 Any one of .

[0140] R 51 , R 52 , R 53 Each is independently selected from any one or a combination of at least two of a C1-C20 straight or branched alkyl group, a C6-C30 aryl group, a C3-C30 heteroaryl group, a C2-C10 alkenyl group, and a C3-C20 cycloalkyl group; 52 and R 53 Not connected or connected to form a ring through chemical bonds.

[0141] Preferably, the R 51 , R 52 , R 53Each is independently selected from any one of C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight chain or branched alkyl, C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16 or C18, etc.) aryl, and further preferably any one of C1-C6 straight chain or branched alkyl, phenyl, naphthyl, biphenyl.

[0142] Preferably, L is selected from a single bond, Any one of, more preferably a single bond,

[0143] Preferably, the second compound has a structure shown in any one of the following P1-P190:

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154] Preferably, the mass ratio of the first compound to the second compound is 1:(0.1-2), for example, it can be 1:0.2, 1:0.3, 1:0.4, 1:0.5, 1:0.6, 1:0.7, 1:0.8, 1:0.9, 1:1, 1:1.1, 1:1.2, 1:1.3, 1:1.4, 1:1.5, 1:1.6, 1:1.7, 1:1.8 or 1:1.9, and more preferably 1:(0.5-1.5).

[0155] In a fourth aspect, the present invention provides an organic electroluminescent device, comprising a first electrode, a second electrode, and an organic layer arranged between the first electrode and the second electrode, wherein the organic layer comprises at least one of the organic compound described in the first aspect and the organic electroluminescent material described in the third aspect.

[0156] Preferably, the organic layer comprises a light-emitting layer, and the light-emitting layer comprises at least one of the organic compound described in the first aspect and the organic electroluminescent material described in the third aspect.

[0157] Preferably, the light-emitting layer comprises a host material and a doping material, and the host material comprises at least one of the organic compound described in the first aspect and the organic electroluminescent material described in the third aspect.

[0158] Preferably, the doping material (also called "dye", "guest material", "dopant") is a phosphorescent doping material, and more preferably a red phosphorescent doping material.

[0159] Preferably, based on the mass of the main material being 100%, the mass of the doping material is 1-10%, for example, 2%, 3%, 4%, 5%, 6%, 7%, 8% or 9%.

[0160] Preferably, based on 100% of the mass of the organic electroluminescent material, the mass of the doping material is 1-10%, for example, 2%, 3%, 4%, 5%, 6%, 7%, 8% or 9%.

[0161] Preferably, the organic layer further includes a hole transport region and an electron transport region.

[0162] Preferably, the hole transport region includes any one of a hole injection layer, a hole transport layer, and an electron blocking layer, or a combination of at least two of them.

[0163] Preferably, the electron transport region includes any one of an electron injection layer, an electron transport layer, and a hole blocking layer, or a combination of at least two of them.

[0164] Optionally, the electron transport layer comprises at least one organic compound described in the first aspect; and / or the hole blocking layer comprises at least one organic compound described in the first aspect.

[0165] In a preferred technical solution, the organic electroluminescent device (OLED device) includes a first electrode and a second electrode, and an organic layer located between the electrodes. The organic layer can be divided into multiple regions, for example, including a hole transport region, a light-emitting layer, and an electron transport region; the light-emitting layer contains at least one of the organic compound and the organic electroluminescent material provided by the present invention.

[0166] In a preferred technical solution, the organic electroluminescent device comprises a first electrode, a plurality of light-emitting functional layers (organic layers) and a second electrode arranged in sequence; the organic layer comprises a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer and an electron injection layer arranged in sequence, and the hole injection layer is in contact with the first electrode (anode). The organic layer (preferably a light-emitting layer) comprises at least one of the organic compound and the organic electroluminescent material provided by the present invention.

[0167] In a preferred technical solution, a substrate can be used below the first electrode or above the second electrode. The substrate is glass or polymer material with excellent mechanical strength, thermal stability, water resistance and transparency. In addition, a thin film transistor (TFT) can also be provided on the substrate used as a display.

[0168] The first electrode can be formed by sputtering or depositing the material used as the first electrode on the substrate. When the first electrode is used as an anode, an oxide transparent conductive material such as indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO2), zinc oxide (ZnO) and any combination thereof can be used. When the first electrode is used as a cathode, a metal or alloy such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), ytterbium (Yb), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag) and any combination thereof can be used.

[0169] The organic layer can be formed on the electrode by vacuum thermal evaporation, spin coating, printing, etc. The compound used as the organic layer can be an organic small molecule, an organic macromolecule or a polymer, and a combination thereof.

[0170] The hole transport region is located between the anode and the light-emitting layer. The hole transport region can be a single-layer hole transport layer (HTL), including a single-layer hole transport layer containing only one compound and a single-layer hole transport layer containing multiple compounds. The hole transport region can also be a multilayer structure including at least one layer of a hole injection layer (HIL), a hole transport layer (HTL), and an electron blocking layer (EBL); wherein the HIL is located between the anode and the HTL, and the EBL is located between the HTL and the light-emitting layer.

[0171] The material of the hole transport region can be selected from, but not limited to, phthalocyanine derivatives such as CuPc, conductive polymers or polymers containing conductive dopants such as polyphenylene ethylene, polyaniline / dodecylbenzenesulfonic acid (Pani / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (Pani / CSA), polyaniline / poly(4-styrenesulfonate) (Pani / PSS), aromatic amine derivatives, wherein the aromatic amine derivatives include the compounds shown in HT-1 to HT-50 below; or any combination thereof.

[0172]

[0173]

[0174]

[0175] The hole injection layer is located between the anode and the hole transport layer. The hole injection layer can be a single compound material or a combination of multiple compounds. For example, the hole injection layer can use one or more compounds of HT-1 to HT-50 mentioned above, or one or more compounds of HI-1 to HI-3 described below; or one or more compounds of HT-1 to HT-50 can be doped with one or more compounds of HI-1 to HI-3 described below.

[0176]

[0177] The light-emitting layer includes a host material (Host, the organic compound and / or organic electroluminescent material provided by the present invention), and also includes a light-emitting dye (i.e., a dopant) that can emit different wavelength spectra. The light-emitting layer can be a monochrome light-emitting layer that emits a single color such as red, green, and blue. A plurality of monochrome light-emitting layers of different colors can be arranged in a planar manner according to a pixel pattern, or they can be stacked together to form a color light-emitting layer. When light-emitting layers of different colors are stacked together, they can be separated from each other or connected to each other. The light-emitting layer can also be a single color light-emitting layer that can simultaneously emit different colors such as red, green, and blue.

[0178] According to different technologies, the light-emitting layer material can be made of different materials such as fluorescent electroluminescent materials, phosphorescent electroluminescent materials, and thermally activated delayed fluorescent materials. In an OLED device, a single light-emitting technology can be used, or a combination of multiple different light-emitting technologies can be used. These different light-emitting materials classified by technology can emit light of the same color or different colors.

[0179] In one aspect of the present invention, the light-emitting layer adopts fluorescent electroluminescence technology. The fluorescent host material of the light-emitting layer can be selected from, but not limited to, one or more combinations of BFH-1 to BFH-17 listed below.

[0180]

[0181] In one aspect of the present invention, the light-emitting layer adopts fluorescent electroluminescence technology. The fluorescent dopant of the light-emitting layer can be selected from, but not limited to, one or more combinations of BFD-1 to BFD-24 listed below.

[0182]

[0183]

[0184] In one aspect of the present invention, the light-emitting layer adopts phosphorescent electroluminescence technology. In the preferred technical solution of the present invention, the material of the light-emitting layer is a phosphorescent host material, and the phosphorescent host material is an organic compound and / or an organic electroluminescent material provided by the present invention. Optionally, the phosphorescent doping material of the light-emitting layer can be selected from, but not limited to, one or more combinations of RPD-1 to RPD-28 listed below.

[0185]

[0186]

[0187] In one aspect of the present invention, the light-emitting layer adopts phosphorescent electroluminescence technology. The phosphorescent doping material of the light-emitting layer can be selected from, but not limited to, one or more combinations of GPD-1 to GPD-47 listed below.

[0188]

[0189] Where D is deuterium.

[0190] In one aspect of the present invention, the light-emitting layer adopts phosphorescent electroluminescence technology. The phosphorescent doping material of the light-emitting layer can be selected from, but not limited to, one or more combinations of YPD-1 to YPD-11 listed below.

[0191]

[0192] The organic layer may further include an electron transport region between the light-emitting layer and the cathode. The electron transport region may be an electron transport layer (ETL) of a single-layer structure, including a single-layer electron transport layer containing only one compound and a single-layer electron transport layer containing multiple compounds. The electron transport region may also be a multilayer structure including at least one layer of an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL); wherein the HBL is located between the light-emitting layer and the ETL, and the EIL is located between the cathode and the ETL.

[0193] In one aspect of the present invention, the electron transport layer material can be selected from, but not limited to, one or more combinations of ET-1 to ET-73 listed below.

[0194]

[0195]

[0196]

[0197]

[0198] In one aspect of the present invention, a hole blocking layer (HBL) is located between the electron transport layer and the light emitting layer. The hole blocking layer may be one or more compounds of the above ET-1 to ET-73, but is not limited thereto.

[0199] The device may also include an electron injection layer located between the electron transport layer and the cathode. The electron injection layer material includes but is not limited to one or more combinations of the following: LiQ, LiF, NaCl, CsF, Li2O, Cs2CO3, BaO, Na, Li, Ca, Mg, and Yb.

[0200] The cathode of the device can be a metal such as a magnesium-silver mixture, LiF / Al, ITO, a metal mixture, or a metal oxide.

[0201] In a fifth aspect, the present invention provides a display device, comprising the organic electroluminescent device as described in the fourth aspect.

[0202] Compared with the prior art, the present invention has the following beneficial effects:

[0203] The organic compound provided by the present invention has a structure shown in Formula IA or Formula IB, and through the design of the molecular structure, it has a specific spatial configuration, the overall planar conjugation of the molecular structure is better, and it can effectively transmit and inject electrons and holes, showing excellent carrier mobility and photoelectric properties. The organic compound is used for organic electroluminescent devices, and is particularly suitable as a host material, has excellent carrier transport performance, and is conducive to the exciton energy transmission between the host material and the dye, can effectively improve the luminous efficiency of the device, reduce the driving voltage, and extend the service life, so that the device has better comprehensive performance, and meets the current panel and display manufacturing industry requirements for high-performance organic materials. DETAILED DESCRIPTION

[0204] The technical solution of the present invention is further described below by specific implementation methods. It should be understood by those skilled in the art that the embodiments are only used to help understand the present invention and should not be regarded as specific limitations of the present invention.

[0205] The organic compound represented by Formula IA or Formula IB of the present invention can be synthesized by known organic synthesis methods. An exemplary synthesis route is given below, but those skilled in the art can also obtain it by other known methods.

[0206] In one embodiment, the organic compound has a structure shown in Formula IA and can be prepared by a representative synthetic route as shown below:

[0207] Wherein, X, Y, Ar, R, R', a, and b have the same defined ranges as those of Formula IA; M1, M2, M3, and M4 are each independently selected from any one of I, Br, Cl, and OTf (trifluoromethanesulfonate).

[0208] In one embodiment, the organic compound has a structure as shown in Formula IB, and its representative synthetic route is similar to the above route, except that the intermediate 1 is replaced by Replace intermediate 2 with That's it.

[0209] In one embodiment, the representative synthetic route of intermediate M1 is as follows:

[0210]

[0211] The first step is to use 1-bromo-8-methoxynaphthalene as a raw material and react it with triisopropyl borate under the action of n-butyl lithium to generate 8-methoxy-1-naphthalene boronic acid M1-1; the second step is to react the intermediate M1-1 with 2-bromo-3 (or 4,5,6)-chlorofluorobenzene through Suzuki coupling reaction to generate intermediate M1-3; the third step is to demethylate the intermediate M1-3 under the action of boron tribromide to generate intermediate M1-4; the fourth step is to ring-close the intermediate M1-4 under the action of cesium carbonate to generate intermediate M1.

[0212] In one embodiment, the representative synthetic route of intermediate M2 is as follows:

[0213]

[0214] The intermediate M2 is synthesized by a method similar to that of the intermediate M1, except that 1-bromo-8-methoxynaphthalene is replaced by chloro-8-methoxy-1-bromonaphthalene as the raw material, and 2-bromofluorobenzene is replaced by 2-bromo-3 (or 4, 5, 6)-chlorofluorobenzene as the starting material.

[0215] In a specific embodiment, the representative synthesis route of intermediate M3 is as follows, which can be synthesized with reference to the synthesis method in org.lett2019, 21, 233-236:

[0216]

[0217] The following is a description of the synthesis method of the organic compound by using a specific synthesis example. The following synthesis example provides a specific synthesis method of a representative compound, and the solvents, reagents, intermediates and other chemical reagents involved in the synthesis example can all be purchased from the domestic chemical product market.

[0218] In the following synthesis examples of the present invention, the mass spectrum (MS, m / z) data of all products were obtained by testing with an ABSCIEX mass spectrometer (4000QTRAP).

[0219] Intermediate Synthesis Example 1: Synthesis of Intermediate M1A

[0220]

[0221] (1) Preparation of compound M1A-1

[0222] Under nitrogen protection, add 8-methoxy-1-bromonaphthalene (236g) and 2L of anhydrous tetrahydrofuran to a dry three-necked flask, cool to -78°C in a liquid nitrogen ethanol bath, add 0.44L (2.5M) of n-butyl lithium dropwise, keep warm for half an hour, add triisopropyl borate (225g) dropwise at -78°C, and naturally warm to room temperature and stir for 2h. Add water to quench the reaction and separate the liquids. Extract the aqueous phase with ethyl acetate and combine the organic phases, dry over anhydrous sodium sulfate, filter, and remove the solvent by vacuum rotary evaporation. The crude product is purified by column chromatography to obtain compound M1A-1 (145g).

[0223] (2) Preparation of compound M1A-2

[0224] Compound M1A-1 (40.4 g), 2-bromo-6-chlorofluorobenzene (41.6 g), and potassium carbonate (83 g) were dissolved in a three-necked flask containing toluene / ethanol / water (0.5 L / 0.1 L / 0.1 L). After nitrogen was replaced under stirring, tetrakistriphenylphosphine palladium (2.3 g) was added. After the addition was completed, the reaction system was heated to reflux for 8 h. The reaction was followed by thin layer chromatography (TLC). The temperature was lowered to room temperature, the liquids were separated, the aqueous phase was extracted with ethyl acetate, the organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate, filtered, the solvent was removed by vacuum rotary evaporation, and the compound M1A-2 (43 g) was obtained by column chromatography purification.

[0225] (3) Preparation of Compound M1A-3

[0226] Compound M1A-2 (43 g) and 0.5 L of dichloromethane were added to a three-necked flask, and boron tribromide (37 g) was added dropwise under stirring. After the addition, the reaction was maintained at room temperature for 3 h. TLC showed that the reaction of the raw materials was complete. The reaction system was slowly poured into stirred ice water to quench. The liquid was separated, the aqueous phase was extracted with dichloromethane, the organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and the solvent was removed by vacuum rotary evaporation. The obtained crude product was directly used in the next step reaction.

[0227] (4) Preparation of intermediate M1A

[0228] The compound M1A-3 obtained in the previous step was dissolved in a three-necked flask containing 400 mL of N,N-dimethylformamide (DMF), and cesium carbonate (98 g) was added. The mixture was heated to 120°C for 6 h under stirring, and the reaction was completed by TLC tracking. After cooling to room temperature, the reaction mixture was also poured into stirred water, and the precipitated solid was filtered, washed with water and ethanol respectively, and dried to obtain the target product, namely intermediate M1A (23 g).

[0229] Intermediate Synthesis Example 2: Synthesis of Intermediate M1B

[0230]

[0231] Intermediate M1B was synthesized by a method similar to that for synthesizing intermediate M1A, except that the raw material 2-bromo-6-chlorofluorobenzene in step (2) was replaced by an equal molar amount of 2-bromo-5-chlorofluorobenzene.

[0232] Intermediate Synthesis Example 3: Synthesis of Intermediate M1C

[0233]

[0234] Intermediate M1C was synthesized by a method similar to that for synthesizing intermediate M1A, except that the raw material 2-bromo-6-chlorofluorobenzene in step (2) was replaced by an equimolar amount of 2-bromo-4-chlorofluorobenzene.

[0235] Intermediate Synthesis Example 4: Synthesis of Intermediate M1D

[0236]

[0237] Intermediate M1D was synthesized by a method similar to that for synthesizing intermediate M1A, except that the raw material 2-bromo-6-chlorofluorobenzene in step (2) was replaced by an equimolar amount of 2-bromo-3-chlorofluorobenzene.

[0238] Intermediate Synthesis Example 5: Synthesis of Intermediate M2A

[0239]

[0240] Intermediate M2A is synthesized by a method similar to that for synthesizing intermediate M1A, except that the raw material 8-methoxy-1-bromonaphthalene in step (1) is replaced by an equal molar amount of 1-bromo-7-chloro-8-methoxynaphthalene, and the raw material 2-bromo-6-chlorofluorobenzene in step (2) is replaced by an equal molar amount of 2-bromofluorobenzene.

[0241] Synthesis Example 1: Synthesis of Organic Compound N3

[0242]

[0243]

[0244] (1) Preparation of intermediate M1C-B

[0245] The intermediate M1C (25.2g), biboronic acid pinacol ester (38.1g), potassium acetate (29g), tris (dibenzylidene-BASE acetone) palladium (0) (916mg), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (410mg) were dissolved in a three-necked flask containing 500mL 1,4-dioxane, and refluxed for 6h after nitrogen replacement. TLC tracked the completion of the reaction. The reaction solution was cooled to room temperature, the solvent was removed by vacuum rotary evaporation, DCM was dissolved, washed with water, separated, the organic phase was dried over anhydrous sodium sulfate, filtered, the solvent was removed by vacuum rotary evaporation, and the compound M1C-B (30g) was purified by column chromatography.

[0246] (2) Preparation of intermediate N3-1

[0247] The intermediate M1C-B (25g), 1-bromo-3-chloronaphthalene (17.5g), potassium carbonate (30g), tetrakistriphenylphosphine palladium (839mg) were dissolved in a three-necked flask containing toluene / ethanol / water (300mL / 100mL / 100mL), and the mixture was refluxed for 4h after nitrogen replacement. The reaction was completed by TLC tracking. The reaction solution was cooled to room temperature, separated, the aqueous phase was extracted with toluene, the combined organic phases were dried over anhydrous sodium sulfate, filtered, the solvent was removed by vacuum rotary evaporation, and the intermediate N3-1 (23g) was obtained by column chromatography purification.

[0248] (3) Preparation of intermediate N3-2

[0249] The intermediate N3-1 (20g), biboric acid pinacol ester (20g), potassium acetate (15g), tris (dibenzyl-BASE acetone) palladium (0) (485mg), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (400mg) were dissolved in a three-necked flask containing 500mL 1,4-dioxane, and refluxed for 5h after nitrogen replacement. TLC tracking of the reaction was complete. The reaction solution was cooled to room temperature, the solvent was removed by vacuum rotary evaporation, dissolved in dichloromethane DCM, washed with water, separated, the organic phase was dried over anhydrous sodium sulfate, filtered, the solvent was removed by vacuum rotary evaporation, and purified by column chromatography to obtain compound N3-2 (20g).

[0250] (4) Preparation of target product N3

[0251] Compound N3-2 (10 g), 2-chloro-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine (7.6 g), potassium carbonate (9 g), tetrakistriphenylphosphine palladium (245 mg) were dissolved in a three-necked flask containing toluene / ethanol / water (150 mL / 50 mL / 50 mL), replaced with nitrogen, and refluxed for 4 hours. TLC was followed to complete the reaction. The reaction solution was cooled to room temperature, separated, the aqueous phase was extracted with toluene, the organic phases were combined and dried over anhydrous sodium sulfate, filtered, the solvent was removed by vacuum rotary evaporation, and the target product N3 (10 g) was obtained by column chromatography purification. The calculated molecular weight value is 665.21, and the measured value m / z is 666.2 (M+1).

[0252] Synthesis Example 2: Synthesis of Organic Compound N8

[0253]

[0254]

[0255] Compound N8 was synthesized by a method similar to that in Synthesis Example 1, except that the raw material 1-bromo-3-chloronaphthalene in step (2) was replaced by an equal molar amount of 1-chloro-3-bromonaphthalene. The calculated molecular weight of the obtained compound N8 was 665.21, and the measured value m / z was 666.2 (M+1).

[0256] Synthesis Example 3: Synthesis of Organic Compound N30

[0257]

[0258] Compound N30 was synthesized by a method similar to that in Synthesis Example 1, except that the raw material M1C in step (1) was replaced by M2A, the raw material 1-bromo-3-chloronaphthalene in step (2) was replaced by an equal molar amount of 1-chloro-3-bromonaphthalene, and the raw material 2-chloro-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine in step (4) was replaced by an equal molar amount of 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine. The calculated molecular weight of the obtained compound N30 was 665.21, and the measured value m / z was 666.2 (M+1).

[0259] Synthesis Example 4: Synthesis of Organic Compound N65

[0260]

[0261]

[0262] Compound N65 was synthesized by a method similar to that in Synthesis Example 1, with the only difference that the raw material M1C in step (1) was replaced by M2A, and the raw material 2-chloro-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine in step (4) was replaced by an equal molar amount of 2-chloro-4-(dibenzo[b,d]furan-1-yl)-6-(2-naphthyl)-1,3,5-triazine. The calculated molecular weight of the obtained compound N65 was 715.23, and the measured value m / z was 716.2 (M+1).

[0263] Synthesis Example 5: Synthesis of Organic Compound N76

[0264]

[0265] Compound N76 was synthesized by a method similar to that in Synthesis Example 1, except that the raw material M1C in step (1) was replaced by M1A, the raw material 1-bromo-3-chloronaphthalene in step (2) was replaced by an equal molar amount of 1-chloro-3-bromonaphthalene, and the raw material 2-chloro-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine in step (4) was replaced by an equal molar amount of 2-chloro-4-(dibenzo[b,d]thiophene-1-yl)-6-phenyl-1,3,5-triazine. The calculated molecular weight of the obtained compound N76 was 681.19, and the measured value m / z was 682.2 (M+1).

[0266] Synthesis Example 6: Synthesis of Organic Compound N112

[0267]

[0268]

[0269] Compound N112 was synthesized by a method similar to that in Synthesis Example 1, except that the raw material M1C in step (1) was replaced by M2A, and the raw material 1-bromo-3-chloronaphthalene in step (2) was replaced by an equal molar amount of 1-chloro-6-bromonaphthalene. The calculated molecular weight of the obtained compound N112 was 665.21, and the measured value m / z was 666.2 (M+1).

[0270] Device Example 1

[0271] An organic electroluminescent device comprises an anode (ITO), a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, an electron transport layer, an electron injection layer and a cathode (Al) arranged in sequence; the specific preparation method is as follows:

[0272] (1) a glass plate coated with an ITO transparent conductive layer was ultrasonically treated in a commercial cleaning agent, rinsed in deionized water, ultrasonically degreased in a mixed solvent of acetone / ethanol, baked in a clean environment until the water was completely removed, cleaned with ultraviolet light and ozone, and bombarded with a low-energy cation beam;

[0273] (2) Place the glass plate with the ITO anode in a vacuum chamber and evacuate to 1×10 -5 Pa, vacuum evaporating a mixture of compound HT-4:HI-3 (97 / 3, w / w) on the above anode layer as a hole injection layer, the evaporation rate is 0.1 nm / s, and the evaporation film thickness is 10 nm;

[0274] (3) Vacuum evaporation of compound HT-4 on the hole injection layer as a hole transport layer at a rate of 0.1 nm / s and a film thickness of 60 nm;

[0275] (4) vacuum evaporating compound HT-47 on the hole transport layer as an electron blocking layer, with an evaporation rate of 0.1 nm / s and a film thickness of 60 nm;

[0276] (5) vacuum evaporating a light-emitting layer on the electron blocking layer, wherein the light-emitting layer includes a mixture of a main material and a doping material (dye, RPD-8), wherein the main material is a combination of the organic compound N3 provided by the present invention and the compound P190, and the mass ratio of N3 to P190 is 1:1; during evaporation, N3 and P190 are respectively introduced into a small chamber of a vacuum vapor deposition device, and RPD-8 is introduced into another small chamber as a dopant, N3 and P190 are evaporated at a rate of 1:1, and the doping material is doped in an amount of 3 wt % relative to the total amount of the main material and the doping material, so as to form a light-emitting layer with a thickness of 40 nm on the electron blocking layer;

[0277] (6) Vacuum evaporation of 5 nm of compound ET-17 on the light-emitting layer as a hole blocking layer of the device at a evaporation rate of 0.1 nm / s;

[0278] (7) vacuum evaporating a mixture of compounds ET-69:ET-57 (50 / 50, w / w) on the hole blocking layer as an electron transport layer at a rate of 0.1 nm / s and a film thickness of 25 nm;

[0279] (8) vacuum evaporating a compound LiF on the electron transport layer as an electron injection layer at a rate of 0.1 nm / s and a thickness of 1 nm;

[0280] (9) Vacuum-evaporating metal aluminum with a thickness of 150 nm on the electron injection layer as a cathode at a deposition rate of 1 nm / s to obtain the organic electroluminescent device.

[0281] Device Examples 2-11, Comparative Examples 1-4

[0282] An organic electroluminescent device, which differs from device embodiment 1 only in that the host material of the light-emitting layer is replaced with the material in Table 1; other layers, thicknesses, materials and preparation methods are the same as those in device embodiment 1. In Table 1, when the host material is a combination of two compounds (double host material), the mass ratio of the two compounds is 1:1.

[0283] The main material P190 in the device embodiment and the comparative example is

[0284] The main materials in the comparative example are as follows:

[0285] The synthesis methods of the main materials D1 and D2 can refer to the prior art US202202782861A1; the synthesis methods of D3 and D4 can refer to the prior art CN114907281A and CN115215842A respectively.

[0286] Performance test of organic electroluminescent devices:

[0287] (1) Voltage and efficiency: At a brightness of 3000cd / m 2 Specifically, the voltage was increased at a rate of 0.1 V per second, and the brightness of the organic electroluminescent device reached 3000 cd / m 2 The voltage at the same brightness of 3000cd / m 2 Under the condition of 100 ℃ and 80 ℃, the current density of the organic electroluminescent device is measured, and the ratio of brightness to current density is the current efficiency;

[0288] (2) Lifespan: Maintain 60mA / cm 2 The constant current is set to 10000V, and the time for the brightness of the organic electroluminescent device to drop to 97% of the initial brightness is measured in hours to obtain the LT97 lifespan. The performance test results of the device are shown in Table 1.

[0289] Table 1

[0290]

[0291]

[0292] As can be seen from the data in Table 1, the organic compound provided by the present invention has excellent carrier injection and transport properties, and is used as a phosphorescent host material in an organic electroluminescent device, which can effectively improve the efficiency, life and starting voltage of the device. As a preferred technical solution of the present invention, the second compound having a structure shown in Formula II is compounded with the organic compound having a structure shown in Formula IA or Formula IB of the present invention, and can be used as a dual host material in an organic electroluminescent device, which can more effectively improve the luminous efficiency and service life of the device and reduce the device voltage.

[0293] Compared with the host materials and organic electroluminescent devices of Comparative Examples 1-4, the organic compound provided by the present invention as the host material can give the device higher luminous efficiency, longer service life and lower driving voltage. Specifically, in the organic compound of the present invention, the triazine structure and the oxygen hetero-condensed ring are bridged by the 1,3-position of naphthalene, compared with the triazine and the oxygen hetero-condensed ring in the compound D1 of Comparative Example 1, which are bridged by the 1,4-position of the naphthalene ring, and the triazine and the oxygen hetero-condensed ring in the compounds D2 and D3 of Comparative Examples 2-3, which are bridged by the 1,4-position of the benzene ring or biphenyl, the overall planar conjugation of the molecular structure is better, so that better carrier mobility and higher efficiency can be obtained. Moreover, the triazine group in the organic compound of the present invention contains both an aromatic group and a dibenzofuran (thiophene) group. Compared with the comparative compounds D1, D3 and D4 whose triazine groups contain two benzene rings at the same time, the device of the present invention can obtain better voltage, efficiency and life performance. It is speculated that this may be because the heteroaromatic group containing oxygen or sulfur elements is directly connected to the triazine ring, which is beneficial to accelerate the exciton energy transfer from the host to the dye, thereby obtaining better device performance.

[0294] The above experimental data show that the organic compound of the present invention is an organic light-emitting material with good performance as a red light host material of an organic electroluminescent device and has broad application prospects.

[0295] The applicant declares that the present invention uses the above-mentioned embodiments to illustrate the organic compounds, organic electroluminescent materials and their applications, but the present invention is not limited to the above-mentioned embodiments, that is, it does not mean that the present invention must rely on the above-mentioned embodiments to be implemented. Those skilled in the art should understand that any improvement of the present invention, equivalent replacement of various raw materials of the product of the present invention, addition of auxiliary components, selection of specific methods, etc., all fall within the protection scope and disclosure scope of the present invention.

Claims

1. An organic compound, characterized in that The organic compound has a structure as shown in Formula IA or Formula IB: Wherein, X is O or S; Y is selected from O, S, CR 11 R 12 or NR 13 Any of the following: R 11 , R 12 , R 13 are each independently selected from any one of substituted or unsubstituted C1-C20 straight or branched alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C3-C20 cycloalkyl; the R 11 and R 12 Not connected or connected into rings by chemical bonds; Ar is selected from any one of a substituted or unsubstituted C6-C60 aryl group and a substituted or unsubstituted C3-C60 heteroaryl group; R, R', R1, and R2 are each independently selected from any one of halogen, cyano, substituted or unsubstituted C1-C20 straight or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C3-C30 heteroaryl, and substituted or unsubstituted C6-C30 aryl; a and m1 are each independently selected from integers of 0-6, b is selected from integers of 0-3, c is selected from integers of 0-4, d is selected from integers of 0-5, and m2 is selected from integers of 0-7; R 11 , R 12 , R 13 , Ar, R, R', R1, and R2 are each independently selected from any one of halogen, cyano, nitro, hydroxyl, amino, aldehyde, ester, C1-C20 straight or branched alkyl, C1-C20 alkoxy, C2-C10 alkenyl, C3-C20 cycloalkyl, C2-C20 heterocycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl, or a combination of at least two thereof; the substituted substituents are each independently not connected to the adjacent ring structure or are connected to form a ring through chemical bonds.

2. The organic compound according to claim 1, characterized in that The organic compound has a structure as shown in any one of Formula IA-1, Formula IA-2, Formula IB-1, Formula IB-2, Formula IB-3, Formula IB-4, Formula IB-5, Formula IB-6, and Formula IB-7: Wherein, X, Y, Ar, R, R', a, b, c, and d have the same limited ranges as those of Formula IA and Formula IB.

3. The organic compound according to claim 1 or 2, characterized in that The Y is O or S.

4. The organic compound according to claim 1 or 2, characterized in that Ar is selected from any one of a substituted or unsubstituted C6-C20 aryl group and a substituted or unsubstituted C3-C20 heteroaryl group; Preferably, Ar is selected from any one of the following substituted or unsubstituted groups: -* represents the attachment site of the group; Wherein, Z is selected from O, S, CR 21 R 22 or NR 23 Any of the following: R 21 , R 22 , R 23 Each is independently selected from any one or a combination of at least two of a C1-C20 straight or branched alkyl group, a C6-C30 aryl group, a C3-C30 heteroaryl group, a C2-C10 alkenyl group, and a C3-C20 cycloalkyl group; 21 and R 22 Not connected or connected into rings by chemical bonds; The substituents substituted in Ar have the same definition as in claim 1; Preferably, Z is O or S.

5. The organic compound according to claim 4, characterized in that The Ar is selected from Or any one of; -* represents the attachment site of the group.

6. The organic compound according to claim 1 or 2, characterized in that The R and R' are each independently selected from any one of halogen, cyano, substituted or unsubstituted C1-C10 straight or branched alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C3-C20 heteroaryl, substituted or unsubstituted C6-C20 aryl, preferably any one of phenyl, naphthyl, biphenyl, terphenyl, phenylnaphthyl, and naphthylphenyl.

7. The organic compound according to claim 1 or 2, characterized in that The a, b, c, and d are each independently selected from 0 or 1.

8. The organic compound according to claim 1, characterized in that The organic compound has a structure shown in any one of the following N1-N125:

9. Use of an organic compound as claimed in any one of claims 1 to 8, characterized in that: The organic compound is applied to organic electronic devices; Preferably, the organic compound is applied to an organic electroluminescent device; Preferably, the organic compound is used as a light-emitting layer material in an organic electroluminescent device.

10. An organic electroluminescent material, characterized in that: The organic electroluminescent material comprises a combination of a first compound and a second compound; the first compound is an organic compound as claimed in any one of claims 1 to 8, and the second compound is an aromatic amine compound.

11. The organic electroluminescent material according to claim 10, characterized in that: The second compound has a structure as shown in Formula II: Wherein, Ar1 is selected from any one of a substituted or unsubstituted C6-C30 aryl group and a substituted or unsubstituted C3-C30 heteroaryl group; The substituents substituted in Ar1 are each independently selected from any one of halogen, cyano, nitro, hydroxyl, amino, aldehyde, ester, unsubstituted or R"-substituted C1-C20 straight or branched alkyl, unsubstituted or R"-substituted C3-C20 cycloalkyl, unsubstituted or R"-substituted C1-C20 alkoxy, unsubstituted or R"-substituted C2-C20 alkenyl, unsubstituted or R"-substituted C6-C30 aryl, and unsubstituted or R"-substituted C3-C30 heteroaryl; the substituents substituted in Ar1 are each independently not connected to the adjacent ring structure or connected to form a ring through a chemical bond; L is selected from any one of a single bond, a substituted or unsubstituted C6-C30 arylene group, and a substituted or unsubstituted C3-C30 heteroarylene group; R3 and R4 are each independently selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C1-C30 straight or branched alkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C1-C30 alkylsilyl, substituted or unsubstituted C6-C30 arylsilyl, substituted or unsubstituted C1-C30 alkylC6-C30 arylsilyl, substituted or unsubstituted C1-C30 alkylamino, substituted or unsubstituted C2-C30 alkenylamino, substituted or any one of unsubstituted C1-C30 alkyl C2-C30 alkenylamino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C1-C30 alkyl C6-C30 arylamino, substituted or unsubstituted C2-C30 alkenyl C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C1-C30 alkyl C3-C30 heteroarylamino, substituted or unsubstituted C2-C30 alkenyl C3-C30 heteroarylamino, and substituted or unsubstituted C6-C30 aryl C3-C30 heteroarylamino; The substituted substituents and R" in L, R3 and R4 are each independently selected from any one or a combination of at least two of halogen, cyano, nitro, hydroxyl, amino, aldehyde, ester, C1-C20 straight or branched alkyl, C1-C20 alkoxy, C2-C10 alkenyl, C3-C20 cycloalkyl, C2-C20 heterocycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl; the substituted substituents and R" in L, R3 and R4 are each independently not connected to the adjacent ring structure or are connected to form a ring through chemical bonds.

12. The organic electroluminescent material according to claim 11, characterized in that: The Ar1 is selected from any one of the following substituted or unsubstituted groups: Wherein, -* represents the attachment site of the group; X A Selected from O, S, NR 31 or CR 32 R 33 Any of the following: R 31 , R 32 , R 33 Each is independently selected from any one of unsubstituted or R"-substituted C1-C20 straight or branched alkyl, unsubstituted or R"-substituted C3-C20 cycloalkyl, unsubstituted or R"-substituted C2-C20 alkenyl, unsubstituted or R"-substituted C3-C30 heteroaryl, and unsubstituted or R"-substituted C6-C30 aryl; the R 32 and R 33 They are not connected to each other or connected to form a ring through chemical bonds; The substituents substituted in Ar1 have the same definition as in claim 11; Preferably, the R 31 , R 32 , R 33 Each is independently selected from any one of a C1-C10 straight chain or branched chain alkyl group and a C6-C20 aryl group.

13. The organic electroluminescent material according to claim 11, characterized in that: The R3 and R4 are each independently selected from any one of the following groups: -* represents the attachment site of the group.

14. The organic electroluminescent material according to claim 10 or 11, characterized in that: The second compound has a structure shown in any one of the following P1-P190:

15. The organic electroluminescent material according to claim 10, characterized in that: The mass ratio of the first compound to the second compound is 1:(0.1-2), preferably 1:(0.5-1.5).

16. An organic electroluminescent device, characterized in that: The organic electroluminescent device comprises a first electrode, a second electrode and an organic layer disposed between the first electrode and the second electrode, wherein the organic layer comprises at least one of the organic compound according to any one of claims 1 to 8 and the organic electroluminescent material according to any one of claims 10 to 15; Preferably, the organic layer comprises a light-emitting layer, and the light-emitting layer comprises at least one of the organic compound according to any one of claims 1 to 8 and the organic electroluminescent material according to any one of claims 10 to 15; Preferably, the light-emitting layer comprises a host material and a doping material, and the host material comprises at least one of the organic compound according to any one of claims 1 to 8 and the organic electroluminescent material according to any one of claims 10 to 15.

17. A display device, characterized in that: The display device comprises the organic electroluminescent device according to claim 16.

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