Organic compound, organic electroluminescent element, and electronic device

Abstract

The invention relates to an organic compound, an organic electroluminescent device and an electronic device. The organic compound has a structure as shown in a formula 1, and when the organic compound is applied to an organic electroluminescent device, the performance of the device can be remarkably improved.

Description

Technical Field

[0001] This application relates to the field of organic electroluminescent materials technology, specifically to an organic compound, an organic electroluminescent device, and an electronic device. Background Technology

[0002] Organic electroluminescent devices, such as organic light-emitting diodes (OLEDs), typically include a cathode and an anode positioned opposite each other, and a functional layer disposed between the cathode and anode. This functional layer consists of multiple organic or inorganic film layers, typically including an organic light-emitting layer, a hole transport layer, and an electron transport layer. When a voltage is applied to the cathode and anode, an electric field is generated. Under the influence of this electric field, electrons on the cathode side move towards the electroluminescent layer, and holes on the anode side also move towards the light-emitting layer. Electrons and holes combine in the electroluminescent layer to form excitons. These excitons, in an excited state, release energy, causing the electroluminescent layer to emit light. As the third generation of electroluminescent display technology after cathode ray tubes and liquid crystal displays, OLEDs offer numerous advantages such as thinness, fast response, wide color gamut, and transparent display, leading to a wider range of applications, including televisions, automotive displays, smartphones, wearable devices, and lighting.

[0003] Currently, research in the field of organic light-emitting diodes (OLEDs) mainly focuses on two factors: device lifetime and efficiency. With the increasing size of displays, the driving voltage of these devices is also increasing, while synergistic luminescence efficiency and current efficiency also need further improvement. Therefore, to meet the high-performance requirements of these devices, designing and developing higher-performance materials for OLED devices is a necessary research focus for further improving the performance of organic light-emitting diodes. Summary of the Invention

[0004] To address the problems existing in the prior art, the purpose of this application is to provide an organic compound, an organic electroluminescent device, and an electronic device, wherein using the organic compound in the organic electroluminescent device can improve the device's performance.

[0005] According to a first aspect of this application, an organic compound is provided, the organic compound having the structure shown in Formula 1:

[0006]

[0007] Among them, one of X1 and X2 is selected from O, and the other is selected from a single bond;

[0008] R is selected from the structure shown in Formula 2-1 or the structure shown in Formula 2-2;

[0009] L, L1, L2, L3, L4 and L5 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms.

[0010] Ar1, Ar2, Ar3 and Ar4 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups with 6 to 40 carbon atoms, or substituted or unsubstituted heteroaryl groups with 3 to 40 carbon atoms.

[0011] The substituents in L, L1, L2, L3, L4, L5, Ar1, Ar2, Ar3, and Ar4 may be the same or different, and each is independently selected from deuterium, cyano, halogen group, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, triarylsilyl with 12 to 24 carbon atoms, aryl with 6 to 20 carbon atoms, heteroaryl with 3 to 20 carbon atoms, or cycloalkyl with 3 to 10 carbon atoms;

[0012] Each R1, each R2, each R3, and each R4 may be the same or different, and each is independently selected from hydrogen, deuterium, cyano, halogen group, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuteralkyl with 1 to 10 carbon atoms, aryl with 6 to 20 carbon atoms, deuteraryl with 6 to 20 carbon atoms, heteroaryl with 3 to 20 carbon atoms, or deuteraryheteraryl with 3 to 20 carbon atoms;

[0013] a is the number of R1s, and a can be selected from 1, 2, 3 or 4;

[0014] b is the number of R2s, and b can be selected from 1 or 2;

[0015] c is the number of R3s, and c can be selected from 1, 2, 3 or 4;

[0016] d is the number of R4s, and d can be selected from 1, 2, 3 or 4.

[0017] According to a second aspect of this application, an organic electroluminescent device is provided, comprising an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer comprising the organic compound described in the first aspect.

[0018] According to a third aspect of this application, an electronic device is provided, including the organic electroluminescent device described in the second aspect.

[0019] The organic compounds in this application include benzofuran The skeleton structure, in the skeleton structure By attaching triazine or aromatic amine groups to the benzene ring, the organic compound can be used as an electron-transporting red light host material and a hole-transporting red light host material, respectively. This is because, on the one hand, specific... The fused structure of benzofuran is beneficial for regulating the overall conjugation length and charge distribution of the molecule, enabling it to possess a suitable first excited triplet energy level, making it suitable for constructing red light host materials. On the other hand, this framework structure has a large conjugation area, which helps enhance the intermolecular packing of the target compound and increase the charge carriers. Finally, the oxygen atom in the furan ring has two lone pairs of electrons, which can effectively enhance the interaction between compound molecules, further improving the charge carrier mobility. When the organic compounds of this application are used as electron transport and hole transport materials in the hybrid host material, respectively, the charge carrier balance in the luminescent layer is improved, the charge carrier recombination region is broadened, and the exciton generation and utilization efficiency is improved, thus resulting in optimized and improved device luminous efficiency and lifespan. Attached Figure Description

[0020] The accompanying drawings are provided to further understand this application and form part of the specification. They are used together with the following detailed description to explain this application, but do not constitute a limitation thereof.

[0021] Figure 1 This is a schematic diagram of the structure of an organic electroluminescent device according to one embodiment of this application.

[0022] Figure 2 This is a schematic diagram of an electronic device according to one embodiment of this application.

[0023] Explanation of reference numerals in the attached figures

[0024] 100, Anode 200, Cathode 300, Functional Layer 310, Hole Injection Layer 321, Hole Transport Layer

[0025] 322, Light-emitting auxiliary layer; 330, Organic light-emitting layer; 340, Electron transport layer; 350, Electron injection layer; 400, Electronic device. Detailed Implementation

[0026] Exemplary embodiments will now be described more fully with reference to the accompanying drawings. However, exemplary embodiments can be implemented in many forms and should not be construed as limited to the examples set forth herein; rather, these embodiments are provided so that this application will be more comprehensive and complete, and will fully convey the concept of exemplary embodiments to those skilled in the art. The described features, structures, or characteristics may be combined in any suitable manner in one or more embodiments. In the following description, numerous specific details are provided to give a full understanding of embodiments of this application.

[0027] A first aspect of this application provides an organic compound having the structure shown in Formula 1:

[0028]

[0029] Among them, one of X1 and X2 is selected from O, and the other is selected from a single bond;

[0030] R is selected from the structure shown in Formula 2-1 or the structure shown in Formula 2-2;

[0031] L, L1, L2, L3, L4 and L5 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms.

[0032] Ar1, Ar2, Ar3 and Ar4 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups with 6 to 40 carbon atoms, or substituted or unsubstituted heteroaryl groups with 3 to 40 carbon atoms.

[0033] The substituents in L, L1, L2, L3, L4, L5, Ar1, Ar2, Ar3, and Ar4 may be the same or different, and each is independently selected from deuterium, cyano, halogen group, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, triarylsilyl with 12 to 24 carbon atoms, aryl with 6 to 20 carbon atoms, heteroaryl with 3 to 20 carbon atoms, or cycloalkyl with 3 to 10 carbon atoms;

[0034] Each R1, each R2, each R3, and each R4 may be the same or different, and each is independently selected from hydrogen, deuterium, cyano, halogen group, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuteralkyl with 1 to 10 carbon atoms, aryl with 6 to 20 carbon atoms, deuteraryl with 6 to 20 carbon atoms, heteroaryl with 3 to 20 carbon atoms, or deuteraryheteraryl with 3 to 20 carbon atoms;

[0035] a is the number of R1s, and a can be selected from 1, 2, 3 or 4;

[0036] b is the number of R2s, and b can be selected from 1 or 2;

[0037] c is the number of R3s, and c can be selected from 1, 2, 3 or 4;

[0038] d is the number of R4s, and d can be selected from 1, 2, 3 or 4.

[0039] In this application, It refers to a chemical bond that is attached to other substituents or bonding sites.

[0040] In this application, the descriptive phrases "each...independently is," "...each independently selected from," and "...each independently selected from" are interchangeable and should be interpreted broadly. They can mean either that the specific options expressed by the same symbol in different groups do not affect each other, or that the specific options expressed by the same symbol in the same group do not affect each other. For example, In this formula, each q is independently 0, 1, 2 or 3, and each R is independently selected from hydrogen, deuterium, fluorine or chlorine. The meaning is as follows: Formula Q-1 indicates that there are q substituents R on the benzene ring. Each R can be the same or different, and the options of each R do not affect each other. Formula Q-2 indicates that there are q substituents R on each benzene ring of biphenyl. The number q of substituents R on the two benzene rings can be the same or different, and each R can be the same or different. The options of each R do not affect each other.

[0041] In this application, the term "substituted or unsubstituted" means that the functional group described after the term may or may not have substituents (hereinafter, for ease of description, substituents are collectively referred to as Rc). For example, "substituted or unsubstituted aryl" refers to an aryl group having a substituent Rc or an unsubstituted aryl group. The aforementioned substituents, i.e., Rc, can be, for example, deuterium, halogen groups, cyano, alkyl, haloalkyl, deuterated alkyl, aryl, heteroaryl, deuterated aryl, deuterated heteroaryl, cycloalkyl, trialkylsilyl, or triarylsilyl, etc. The number of substituents Rc can be one or more.

[0042] In this application, the number of carbon atoms in substituted or unsubstituted functional groups refers to the total number of carbon atoms. For example, if L1 is a substituted arylene with 12 carbon atoms, then the total number of carbon atoms in the arylene and its substituents is 12.

[0043] In this application, a non-positioned linker bond refers to a single bond extending from the ring system. This means that one end of the linking bond can connect to any position in the ring system that the bond passes through, and the other end connects to the rest of the compound molecule.

[0044] For example, as shown in equation (f) below, the naphthyl group represented by equation (f) is connected to other positions in the molecule through two non-positional linkages that span the bicyclic ring. This means that any possible connection mode is shown in equations (f-1) to (f-10).

[0045]

[0046] For example, as shown in the following formula (X'), the dibenzofuran group represented by formula (X') is connected to other positions of the molecule through a non-positional linker extending from the middle of one side of the benzene ring. This means that any possible connection mode shown in formulas (X'-1) to (X'-4) is included.

[0047]

[0048] In this application, a non-positional substituent refers to a substituent connected by a single bond extending from the center of the ring system, indicating that the substituent can be attached to any possible position in the ring system. For example, as shown in equation (Y) below, the substituent R' represented by equation (Y) is connected to the quinoline ring by a non-positional linking bond, which means that it includes any possible connection mode shown in equations (Y-1) to (Y-7).

[0049]

[0050] In this application, the number of carbon atoms in L, L1, L2, L3, L4, L5, Ar1, Ar2, Ar3, Ar4, R1, R2, R3, and R4 refers to the total number of carbon atoms. For example, if L is selected from a substituted arylene with 12 carbon atoms, then the total number of carbon atoms in the arylene and its substituents is 12.

[0051] In this application, "alkyl group having 1 to 10 carbon atoms" can include straight-chain alkyl groups or branched alkyl groups. An alkyl group may have 1 to 10 carbon atoms. In this application, numerical ranges such as "1 to 10" refer to integers within a given range; for example, "1 to 10 carbon atoms" means an alkyl group that may contain 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10 carbon atoms. Specific examples include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, heptyl, n-octyl, 2-ethylhexyl, nonyl, decyl, 3,7-dimethyloctyl, etc.

[0052] In this application, "cycloalkyl group having 3 to 10 carbon atoms" refers to a group derived from a saturated cyclic carbon chain structure. A cycloalkyl group may have 3 to 10 carbon atoms; in this application, numerical ranges such as "3 to 10" refer to integers within a given range; for example, "5 to 10 carbon atoms" means that it may contain 5, 6, 7, 8, 9, or 10 carbon atoms. Optionally, specific embodiments of cycloalkyl groups include, but are not limited to, cyclopentyl, cyclohexyl, adamantyl, norbornyl, etc.

[0053] In this application, aryl refers to any optional functional group or substituent derived from an aromatic carbon ring. The aryl group can be a monocyclic aryl (e.g., phenyl) or a polycyclic aryl; in other words, the aryl group can be a monocyclic aryl, a fused-ring aryl, two or more monocyclic aryl groups linked by carbon-carbon bonds, a monocyclic aryl and a fused-ring aryl linked by carbon-carbon bonds, or two or more fused-ring aryl groups linked by carbon-carbon bonds. That is, unless otherwise stated, two or more aromatic groups linked by carbon-carbon bonds can also be considered as the aryl group in this application. Fused-ring aryl groups may include, for example, bicyclic fused aryl (e.g., naphthyl), tricyclic fused aryl (e.g., phenanthrene, fluorenyl, anthracene), etc. The aryl group does not contain heteroatoms such as B, N, O, S, P, Se, and Si. Examples of aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, spirodifluorenyl, anthracene, phenanthrene, biphenyl, terphenyl, perylene, pyrene, benzofluoranthyl, etc. The aryl group can be substituted with phenyl, cyclopentanespirofluorenyl, cyclohexanespirofluorenyl, etc. For example, in this application, the number of carbon atoms in the substituted or unsubstituted aryl group can be 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, or 40. In this application, biphenyl can be understood as a phenyl-substituted aryl group or an unsubstituted aryl group.

[0054] In this application, the term "arylene" refers to a divalent group formed by the further loss of a hydrogen atom from an aryl group.

[0055] In this application, a substituted aryl group refers to an aryl group in which one or more hydrogen atoms are replaced by other groups. For example, at least one hydrogen atom may be replaced by a deuterium, halogen group, cyano, alkyl, deuterated alkyl, haloalkyl, cycloalkyl, aryl, heteroaryl, trialkylsilyl, or triarylsilyl group. It is understood that the number of carbon atoms in a substituted aryl group refers to the total number of carbon atoms in the aryl group and its substituents. For example, Ar1 is... Therefore, it has 10 carbon atoms.

[0056] In this application, aryl groups used as substituents include, but are not limited to, phenyl, naphthyl, and biphenyl groups.

[0057] In this application, the fluorene group can be substituted by one or more substituents. When the fluorene group is substituted, the substituted fluorene group can be: etc., but not limited to this.

[0058] In this application, terphenyl includes

[0059] In this application, a heteroaryl group refers to a monovalent aromatic ring or its derivative containing 1, 2, 3, 4, 5, or 6 heteroatoms. The heteroatoms can be at least one of B, O, N, P, Si, Se, and S. A heteroaryl group can be a monocyclic or polycyclic heteroaryl group; in other words, a heteroaryl group can be a single aromatic ring system or a system of multiple aromatic rings linked by carbon-carbon bonds, and any aromatic ring system can be a single aromatic monocyclic ring or a fused aromatic ring. For example, a heteroaryl group may include thiophene, furanyl, pyrroleyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridineyl, pyridazinyl, quinolinyl, quinazolinyl, quinoxolinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, isoquinolinyl, indolyl, carbazole, benzoxazolyl, and benzimidazole. The group includes, but is not limited to, benzothiazolyl, benzocarbazolyl, benzothiophenel, dibenzothiophenel, thienozothiophenel, benzofuranyl, phenanthrolinel, isoxazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, silanyl, dibenzofuranyl, and N-arylcarbazolyl (such as N-phenylcarbazolyl), N-heteroarylcarbazolyl (such as N-pyridylcarbazolyl), and N-alkylcarbazolyl (such as N-methylcarbazolyl), etc. Among these, thiophenel, furanyl, and phenanthrolinel are heteroaryl groups of the single aromatic ring type, while N-arylcarbazolyl (such as N-phenylcarbazolyl) and N-heteroarylcarbazolyl are heteroaryl groups of the polycyclic system type linked by carbon-carbon conjugation. For example, in this application, the number of carbon atoms in the substituted or unsubstituted heteroaryl group can be 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, or 40.

[0060] In this application, the term "hybrid aryl" refers to a divalent group formed by the further loss of a hydrogen atom by a heteroaryl group.

[0061] In this application, the substituted heteroaryl group may be one or more hydrogen atoms of the heteroaryl group that are replaced by groups such as deuterium, halogen group, cyano, alkyl, deuterated alkyl, haloalkyl, cycloalkyl, aryl, heteroaryl, trialkylsilyl, triarylsilyl, etc.

[0062] It should be understood that the number of carbon atoms in a substituted heteroaryl group refers to the total number of carbon atoms in the heteroaryl group and the substituents on it.

[0063] In this application, the heteroaryl group used as a substituent includes, but is not limited to, dibenzofuranyl, dibenzothiophenyl, carbazoyl, N-phenylcarbazoyl, etc.

[0064] In this application, "deuterated" means that at least one hydrogen ("H") in a compound or group is replaced by deuterium ("D"); specifically, a deuterated compound or deuterated group can be a compound or group in which one, more or all of the available hydrogens have been replaced by deuterium.

[0065] In this application, the halogen group can be fluorine, chlorine, bromine, or iodine.

[0066] In this application, a haloalkyl group may be an alkyl group in which one or more hydrogen atoms are replaced by halogen atoms. Specific examples of haloalkyl groups include, but are not limited to, trifluoromethyl.

[0067] In this application, a deuterated alkyl group can be an alkyl group in which one or more hydrogen atoms are replaced by deuterium. Specific examples of deuterated alkyl groups include, but are not limited to, trideuterated methyl groups.

[0068] In this application, specific examples of trialkylsilyl groups include, but are not limited to, trimethylsilyl groups.

[0069] In this application, specific examples of triarylsilyl groups include, but are not limited to, triphenylsilyl groups.

[0070] In this application, the deuterated aryl group can be one or more hydrogen atoms (H) of the aryl group that are replaced by deuterium (D). Specific examples of deuterated aryl groups include, but are not limited to, pentadeuterated phenyl and heptadeuterated naphthyl.

[0071] In this application, the deuterated heteroaryl group can be one or more hydrogen atoms (H) of the heteroaryl group that are replaced by deuterium (D). Specific examples of deuterated heteroaryl groups include, but are not limited to, heptadeuterated dibenzofuranyl.

[0072] In some embodiments, the organic compounds described in this application are selected from the structures shown in Formula 1-1 or Formula 1-2:

[0073]

[0074] The definitions of R, R1, R2, R3, R4, a, b, c, and d are the same as in Equation 1.

[0075] In some embodiments, in the structure shown in Formula 2-1, L, L1 and L2 may be the same or different, and each is independently selected from a single bond, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, or a substituted or unsubstituted heteroaryl group having 12 to 18 carbon atoms.

[0076] Furthermore, when L, L1, and L2 are the same or different, and each is independently selected from substituted or unsubstituted aryl groups having 6 to 12 carbon atoms, the number of carbon atoms in the aryl group is selected from 6, 7, 8, 9, 10, 11, or 12; when L, L1, and L2 are the same or different, and each is independently selected from substituted or unsubstituted heteroaryl groups having 12 to 18 carbon atoms, the number of carbon atoms in the heteroaryl group is selected from 12, 13, 14, 15, 16, 17, or 18.

[0077] Optionally, the substituents in L, L1 and L2 may be the same or different, and each may be independently selected from deuterium, halogen groups, cyano groups, alkyl groups with 1 to 5 carbon atoms, deuterated alkyl groups with 1 to 5 carbon atoms, haloalkyl groups with 1 to 5 carbon atoms or phenyl groups.

[0078] In some embodiments, in the structure shown in Formula 2-1, L, L1 and L2 may be the same or different, and each is independently selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted dibenzofuranylene, a substituted or unsubstituted dibenzothiopheneylene, or a substituted or unsubstituted carbazolylene.

[0079] Optionally, the substituents in L, L1 and L2 may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trideuterated methyl, trifluoromethyl or phenyl.

[0080] In some embodiments, in the structure shown in Formula 2-1, L, L1, and L2 may be the same or different, and each is independently selected from the group consisting of single bonds or the following groups:

[0081]

[0082] In some embodiments, in the structure shown in Formula 2-1, L, L1, and L2 may be the same or different, and each is independently selected from the group consisting of single bonds or the following groups:

[0083]

[0084] In some embodiments, in the structure shown in Formula 2-1, L is selected from the group consisting of single bonds or the following groups:

[0085]

[0086] In some embodiments, in the structure shown in Formula 2-1, L is selected from the group consisting of single bonds or the following groups:

[0087]

[0088] In some embodiments, in the structure shown in Formula 2-1, L1 and L2 may be the same or different, and each is independently selected from the group consisting of single bonds or the following groups:

[0089]

[0090] In some embodiments, in the structure shown in Formula 2-1, L1 and L2 may be the same or different, and each is independently selected from the group consisting of single bonds or the following groups:

[0091]

[0092] In some embodiments, in the structure shown in Formula 2-1, Ar1 and Ar2 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups having 6 to 18 carbon atoms or substituted or unsubstituted heteroaryl groups having 12 to 18 carbon atoms.

[0093] Furthermore, when Ar1 and Ar2 are the same or different, and each is independently selected from substituted or unsubstituted aryl groups having 6 to 18 carbon atoms, the number of carbon atoms in the aryl group is selected from 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17 or 18; when Ar1 and Ar2 are the same or different, and each is independently selected from substituted or unsubstituted heteroaryl groups having 12 to 18 carbon atoms, the number of carbon atoms in the heteroaryl group is selected from 12, 13, 14, 15, 16, 17 or 18.

[0094] Optionally, the substituents in Ar1 and Ar2 may be the same or different, and each may be independently selected from deuterium, halogen groups, cyano, alkyl with 1 to 5 carbon atoms, haloalkyl with 1 to 5 carbon atoms, deuterated alkyl with 1 to 5 carbon atoms, aryl with 6 to 12 carbon atoms, heteroaryl with 5 to 12 carbon atoms, or trialkylsilyl with 3 to 9 carbon atoms.

[0095] In some embodiments, in the structure shown in Formula 2-1, Ar1 and Ar2 may be the same or different, and each is independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, or substituted or unsubstituted carbazoleyl.

[0096] Optionally, the substituents in Ar1 and Ar2 may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothiophene, carbazolyl, or trimethylsilyl.

[0097] In some embodiments, in the structure shown in Formula 2-1, Ar1 and Ar2 may be the same or different, and each is independently selected from the group consisting of:

[0098]

[0099] In some embodiments, in the structure shown in Formula 2-1, Ar1 and Ar2 may be the same or different, and each is independently selected from the group consisting of:

[0100]

[0101]

[0102] In some embodiments, the structure shown in Equation 2-1, They may be the same or different, and each is independently selected from the group consisting of the following groups:

[0103]

[0104] In some embodiments, the structure shown in Equation 2-1, They may be the same or different, and each is independently selected from the following groups:

[0105]

[0106]

[0107] In some embodiments, the structure shown in Equation 2-1 is selected from the group consisting of the following structures:

[0108]

[0109]

[0110] In some embodiments, in the structure shown in Formula 2-2, L3, L4 and L5 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 12 carbon atoms, or substituted or unsubstituted heteroaryl groups with 12 to 18 carbon atoms.

[0111] Furthermore, when L3, L4, and L5 are the same or different, and each is independently selected from substituted or unsubstituted aryl groups having 6 to 12 carbon atoms, the number of carbon atoms in the aryl group is selected from 6, 7, 8, 9, 10, 11, or 12; when L3, L4, and L5 are the same or different, and each is independently selected from substituted or unsubstituted heteroaryl groups having 12 to 18 carbon atoms, the number of carbon atoms in the heteroaryl group is selected from 12, 13, 14, 15, 16, 17, or 18.

[0112] Optionally, the substituents in L3, L4 and L5 may be the same or different, and each may be independently selected from deuterium, halogen groups, cyano groups, alkyl groups with 1 to 5 carbon atoms, deuterated alkyl groups with 1 to 5 carbon atoms, haloalkyl groups with 1 to 5 carbon atoms or phenyl groups.

[0113] In some embodiments, in the structure shown in Formula 2-2, L3, L4 and L5 may be the same or different, and each is independently selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted dibenzofuranylene, a substituted or unsubstituted dibenzothiopheneylene, or a substituted or unsubstituted carbazolylene.

[0114] Optionally, the substituents in L3, L4 and L5 may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trideuterated methyl, trifluoromethyl or phenyl.

[0115] In some embodiments, in the structure shown in Formula 2-2, L3, L4, and L5 may be the same or different, and each is independently selected from the group consisting of single bonds or the following groups:

[0116]

[0117] In some embodiments, in the structure shown in Formula 2-2, L3, L4, and L5 may be the same or different, and each is independently selected from the group consisting of single bonds or the following groups:

[0118]

[0119] In some embodiments, in the structure shown in Formula 2-2, L5 is selected from the group consisting of single bonds or the following groups:

[0120]

[0121] In some embodiments, in the structure shown in Formula 2-2, L5 is selected from the group consisting of single bonds or the following groups:

[0122]

[0123] In some embodiments, in the structure shown in Formula 2-2, L3 and L4 may be the same or different, and each is independently selected from the group consisting of single bonds or the following groups:

[0124]

[0125] In some embodiments, in the structure shown in Formula 2-2, L3 and L4 may be the same or different, and each is independently selected from the group consisting of single bonds or the following groups:

[0126]

[0127] In some embodiments, in the structure shown in Formula 2-2, Ar3 and Ar4 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups having 6 to 25 carbon atoms or substituted or unsubstituted heteroaryl groups having 12 to 18 carbon atoms.

[0128] Furthermore, when Ar3 and Ar4 are the same or different, and each is independently selected from substituted or unsubstituted aryl groups having 6 to 25 carbon atoms, the number of carbon atoms in the aryl group is selected from 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, or 25; when Ar3 and Ar4 are the same or different, and each is independently selected from substituted or unsubstituted heteroaryl groups having 12 to 18 carbon atoms, the number of carbon atoms in the heteroaryl group is selected from 12, 13, 14, 15, 16, 17, or 18.

[0129] Optionally, the substituents in Ar3 and Ar4 may be the same or different, and each may be independently selected from deuterium, halogen groups, cyano, alkyl with 1 to 5 carbon atoms, haloalkyl with 1 to 5 carbon atoms, deuterated alkyl with 1 to 5 carbon atoms, aryl with 6 to 12 carbon atoms, heteroaryl with 5 to 12 carbon atoms, trialkylsilyl or triphenylsilyl with 3 to 9 carbon atoms.

[0130] In some embodiments, Ar3 and Ar4 in the structure shown in Formula 2-2 may be the same or different, and each is independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, or substituted or unsubstituted carbazoleyl.

[0131] Optionally, the substituents in Ar3 and Ar4 may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, carbazoyl, trimethylsilyl or triphenylsilyl.

[0132] In some embodiments, in the structure shown in Formula 2-2, Ar3 and Ar4 may be the same or different, and each is independently selected from the group consisting of:

[0133]

[0134] In some embodiments, in the structure shown in Formula 2-2, Ar3 and Ar4 may be the same or different, and each is independently selected from the group consisting of:

[0135]

[0136]

[0137] In some implementations, the structure shown in Equation 2-2, They may be the same or different, and each is independently selected from the group consisting of the following groups:

[0138]

[0139] In some implementations, the structure shown in Equation 2-2, They may be the same or different, and each is independently selected from the following groups:

[0140]

[0141]

[0142] In some embodiments, the structure shown in Equation 2-2 is selected from the group consisting of the following structures:

[0143]

[0144]

[0145] In some embodiments, each R1, each R2, each R3, and each R4 may be the same or different, and each is independently selected from hydrogen, deuterium, cyano, halogen group, alkyl with 1 to 5 carbon atoms, haloalkyl with 1 to 5 carbon atoms, deuteralkyl with 1 to 10 carbon atoms, aryl with 6 to 12 carbon atoms, deuteraryl with 6 to 12 carbon atoms, heteroaryl with 5 to 18 carbon atoms, or deuteraryheteroaryl with 5 to 18 carbon atoms.

[0146] In some embodiments, each R1, each R2, each R3, and each R4 may be the same or different, and each is independently selected from hydrogen, deuterium, cyano, fluorine, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, trifluoromethyl, trideuterated methyl, phenyl, naphthyl, biphenyl, pentadeuterated phenyl, or heptadeuterated naphthyl.

[0147] In some embodiments, the organic compound is selected from the group consisting of the compounds described in claim 12.

[0148] A second aspect of this application provides an organic electroluminescent device, including an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; wherein the functional layer comprises the organic compound described in the first aspect of this application.

[0149] Optionally, the functional layer includes an organic light-emitting layer, which contains the organic compounds of this application.

[0150] Optionally, the organic light-emitting layer may be composed of the organic compounds of this application, or it may be composed of the organic compounds of this application and other materials.

[0151] Optionally, the organic electroluminescent device is a red organic electroluminescent device.

[0152] In some implementations, organic electroluminescent devices such as Figure 1 As shown, it includes an anode 100, a hole transport layer 321, a light-emitting auxiliary layer 322, an organic light-emitting layer 330, an electron transport layer 340, and a cathode 200, which are stacked in sequence.

[0153] In this application, the anode 100 includes an anode material, which is preferably a material with a large work function that facilitates hole injection into the functional layer. Specific examples of anode materials include: metals such as nickel, platinum, vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; or conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, and polyaniline, but are not limited thereto. Preferably, a transparent electrode comprising indium tin oxide (ITO) as the anode is included.

[0154] Optionally, the hole transport layer may include one or more hole transport materials. The hole transport layer material may be selected from carbazole polymers, carbazole-linked triarylamine compounds, or other types of compounds, specifically from the compounds listed below or any combination thereof:

[0155]

[0156]

[0157] In one specific embodiment, the hole transport layer 321 is HT-1 and the light emission auxiliary layer 322 is HT-2.

[0158] Optionally, such as Figure 1As shown, a hole injection layer 310 is further disposed between the anode 100 and the hole transport layer 321 to enhance the ability to inject holes into the hole transport layer 321. The hole injection layer 310 can be selected from benzidine derivatives, starburst-like aryl amine compounds, phthalocyanine derivatives, or other materials; this application does not impose any special limitations on this. The material of the hole injection layer 310 can, for example, be selected from the following compounds or any combination thereof:

[0159]

[0160] In one specific embodiment, the hole injection layer 310 is composed of PD-1 and HT-1.

[0161] Optionally, the organic light-emitting layer 330 may be composed of a single light-emitting material, or it may include a host material and a guest material. Optionally, the organic light-emitting layer 330 is composed of a host material and a guest material. Holes and electrons injected into the organic light-emitting layer 330 can recombine in the organic light-emitting layer 330 to form excitons. The excitons transfer energy to the host material, and the host material transfers energy to the guest material, thereby enabling the guest material to emit light.

[0162] The main material of the organic light-emitting layer 330 can include metal chelate compounds, bis(styrene) derivatives, aromatic amine derivatives, dibenzofuran derivatives, or other types of materials.

[0163] In one specific embodiment, the host material of the organic light-emitting layer 330 is composed of the organic compounds and compound RH-P of this application. composition.

[0164] In one specific embodiment, the main material of the organic light-emitting layer 330 is composed of the organic compounds and compound RH-N of this application. composition.

[0165] The guest material of the organic light-emitting layer 330 can be a compound with a condensed aryl ring or its derivative, a compound with a heteroaryl ring or its derivative, an aromatic amine derivative, or other materials; this application does not impose any special limitations on this. The guest material is also called a dopant or dopant. According to the type of light emission, it can be divided into fluorescent dopant and phosphorescent dopant. Specific examples of phosphorescent dopant include, but are not limited to:

[0166]

[0167] In one specific embodiment, the guest material of the organic light-emitting layer 330 is RD-1.

[0168] Optionally, the electron transport layer 340 can be a single-layer structure or a multi-layer structure, and may include one or more electron transport materials. The electron transport materials typically contain metal complexes or / or nitrogen-containing heterocyclic derivatives. The metal complexes may be selected from, for example, LiQ, Alq3, etc. The nitrogen-containing heterocyclic derivatives may be aromatic rings with a nitrogen-containing six- or five-membered ring skeleton, fused aromatic ring compounds with a nitrogen-containing six- or five-membered ring skeleton, etc. Specific examples include, but are not limited to, 1,10-phenanthroline compounds such as Bphen, NBphen, ET-1, and BimiBphen, or anthracene compounds, triazine compounds, or pyrimidine compounds containing heteroazoyl groups as shown below. Specific examples of the nitrogen-containing heterocyclic derivatives used for the electron transport materials include, but are not limited to:

[0169]

[0170]

[0171] In one specific embodiment, the electron transport layer 340 is composed of ET-1 and LiQ.

[0172] In this application, the cathode 200 may include a cathode material that has a small work function and facilitates electron injection into the functional layer. Specific examples of cathode materials include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; or multilayer materials such as LiF / Al, Liq / Al, LiO2 / Al, LiF / Ca, LiF / Al, and BaF2 / Ca. Preferably, a metal electrode comprising magnesium and silver is included as the cathode.

[0173] Optionally, such as Figure 1 As shown, an electron injection layer 350 is further disposed between the cathode 200 and the electron transport layer 340 to enhance the ability to inject electrons into the electron transport layer 340. The electron injection layer 350 may include inorganic materials such as alkali metal sulfides and alkali metal halides, or may include complexes of alkali metals and organic materials. For example, the electron injection layer 350 includes ytterbium (Yb).

[0174] Optionally, the cathode 200 also has an organic coating.

[0175] In one specific embodiment, the organic coating layer comprises a compound.

[0176] Thirdly, this application provides an electronic device including the organic electroluminescent device described in the second aspect of this application.

[0177] According to one implementation method, such as Figure 2As shown, the provided electronic device 400 includes the aforementioned organic electroluminescent device. The electronic device 400 can be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices, such as, but not limited to, computer screens, mobile phone screens, televisions, electronic paper, emergency lighting, optical modules, etc.

[0178] The following examples illustrate the synthesis method of the compounds in this application, but this disclosure is not limited thereto.

[0179] Synthesis of intermediates

[0180] 1. Synthesis of Sub-a1:

[0181]

[0182] Under a nitrogen atmosphere, RM-1 (20.8 g, 70 mmol) and tetrahydrofuran (dry, 210 mL) were added to a 500 mL three-necked flask; the system was cooled to -78 °C, and a n-butyllithium solution (n-BuLi, 2.0 mol / L n-butyllithium / n-hexane solution, 38.5 mL, 77 mmol) was added dropwise. After the addition was complete, the mixture was kept at -78 °C and stirred for 1 h; while maintaining the temperature at -78 °C, trimethyl borate (B(OCH3)3, 10.91 g) was added dropwise. After the addition of 105 mmol of dilute hydrochloric acid (2 mol / L, 58 mL) was completed, the mixture was kept at -78 °C for 1 h, and then allowed to naturally warm to room temperature. Dilute hydrochloric acid (2 mol / L, 58 mL) was added dropwise to the reaction solution and stirred for 30 min. The mixture was extracted with dichloromethane (100 mL × 3 times), the organic phases were combined and dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by vacuum distillation to obtain the crude product. The crude product was slurried with n-heptane and filtered to obtain a white solid Sub-a1 (10.60 g, yield: 58%).

[0183] Sub-aX (Sub-a2 to Sub-a5) listed in Table 1 were synthesized using the same method as Sub-a1, except that reactant A was used instead of RM-1. The main raw materials used, the intermediates synthesized and their yields are shown in Table 1.

[0184] Table 1

[0185]

[0186] 2. Synthesis of Sub-b1:

[0187]

[0188] Under a nitrogen atmosphere, Sub-a1 (14.41 g, 55 mmol), RM-2 (10.97 g, 50 mmol), tetrakis(triphenylphosphine)palladium (Pd(PPh3)4, 0.58 g, 0.5 mmol), tetrabutylammonium bromide (TBAB, 1.61 g, 5 mmol), anhydrous sodium carbonate (10.60 g, 100 mmol), toluene (180 mL), anhydrous ethanol (45 mL), and deionized water (45 mL) were added sequentially to a 500 mL three-necked flask. Stirring and heating were started, and the mixture was refluxed for 8 h. After the system cooled to room temperature, it was extracted with dichloromethane (100 mL × 3 times). The organic phases were combined, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by vacuum distillation to obtain the crude product. The crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as the mobile phase to obtain a white solid Sub-b1 (12.84 g, yield: 72%).

[0189] Sub-bX (Sub-b2 to Sub-b9) listed in Table 2 were synthesized using the same method as Sub-b1, except that reactant B was used instead of Sub-a1 and reactant C was used instead of RM-2. The main raw materials used, the intermediates synthesized and their yields are shown in Table 2.

[0190] Table 2

[0191]

[0192] 3. Synthesis of Sub-c1:

[0193]

[0194] Under a nitrogen atmosphere, (methoxymethyl)triphenylphosphonium chloride (51.25 g, 149.5 mmol), potassium tert-butoxide (t-BuOK, 18.10 g, 161 mmol), and tetrahydrofuran (dry, 230 mL) were added sequentially to a 1000 mL three-necked flask. The system was cooled to -15 °C and maintained for 30 min. Then, Sub-b1 (46.38 g, 130 mmol) was weighed and dissolved in tetrahydrofuran (dry, 230 mL). This solution was slowly added dropwise to the reaction system while maintaining the temperature at -15 °C during the addition. After the addition was complete, the reaction was stirred at -15 °C for 1 h. The reaction system was then allowed to warm naturally to room temperature and extracted with dichloromethane (200 mL × 3 times). The organic phases were combined, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by vacuum distillation to obtain the crude product. The crude product was purified by silica gel column chromatography using n-heptane / dichloromethane as the mobile phase to obtain a grayish-white solid Sub-c1 (34.52 g, yield: 69%).

[0195] Sub-cX (Sub-c2 to Sub-c9) listed in Table 3 were synthesized using the same method as Sub-c1, except that reactant D was used instead of Sub-b1. The main raw materials used, the intermediates synthesized and their yields are shown in Table 3.

[0196] Table 3

[0197]

[0198]

[0199] 4. Synthesis of Sub-d1:

[0200]

[0201] Under a nitrogen atmosphere, Sub-c1 (45.80 g, 119 mmol), Eaton reagent (4.5 mL), and chlorobenzene (500 mL) were added sequentially to a 1000 mL three-necked flask. The mixture was heated to reflux and stirred for 4 h. After the reaction system cooled to room temperature, the reaction solution was poured into 1000 mL of deionized water, neutralized with saturated sodium hydroxide solution, and then extracted with dichloromethane (250 mL × 3 times). The organic phases were combined, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by vacuum distillation to obtain the crude product. The crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as the mobile phase to obtain a white solid Sub-d1 (26.0 g, yield: 62%).

[0202] Sub-dX (Sub-d2 to Sub-d9) listed in Table 4 were synthesized using the same method as Sub-d1, except that reactant E was used instead of Sub-c1. The main raw materials used, the intermediates synthesized and their yields are shown in Table 4.

[0203] Table 4

[0204]

[0205]

[0206] Synthesis of Sub-d10:

[0207]

[0208] Under a nitrogen atmosphere, Sub-d1 (8.82 g, 25 mmol) and Benzene-D6 (200 mL) were added to a 100 mL three-necked flask. The mixture was heated to 60 °C, and then trifluoromethanesulfonic acid (22.51 g, 150 mmol) was added. The mixture was then heated to boiling and stirred for 24 h. After the reaction system cooled to room temperature, 50 mL of heavy water was added, and the mixture was stirred for 10 min. Then, a saturated aqueous solution of K3PO4 was added to neutralize the reaction mixture. The organic layer was extracted with dichloromethane (50 mL × 3 times), and the combined organic phases were dried over anhydrous sodium sulfate. After filtration, the solvent was removed by vacuum distillation to obtain the crude product. The crude product was purified by silica gel column chromatography using n-heptane / dichloromethane as the mobile phase to obtain a white solid, Sub-d10 (4.94 g, yield: 54%).

[0209] 5. Synthesis of Sub-e1:

[0210]

[0211] Under a nitrogen atmosphere, Sub-d1 (17.64 g, 50 mmol), pinacol diborate (14.0 g, 55 mmol), potassium acetate (10.8 g, 110 mmol), and 1,4-dioxane (180 mL) were added sequentially to a 500 mL three-necked flask. The mixture was stirred and heated until it reached 40 °C. Then, tris(dibenzylacetone)dipalladium (Pd2(dba)3, 0.46 g, 0.50 mmol) and 2-dicyclohexylphosphine-2',4',6'triisopropylbiphenyl (Xphos, 0.48 g, 1.0 mmol) were added rapidly. The mixture was then heated to reflux and stirred overnight. After the system cooled to room temperature, 200 mL of water was added to the system and stirred thoroughly for 30 min. The mixture was then filtered under reduced pressure. The filter cake was washed with deionized water until neutral and then rinsed with 100 mL of anhydrous ethanol to obtain a gray solid. The crude product was slurried once with n-heptane, then dissolved in 200 mL of toluene and passed through a silica gel column to remove the catalyst. After concentration, a white solid Sub-e1 (14.89 g, yield: 67%) was obtained.

[0212] Sub-eX (Sub-e2 to Sub-e10) listed in Table 5 were synthesized using the same method as Sub-e1, except that reactant F was used instead of Sub-d1. The main raw materials used, the intermediates synthesized and their yields are shown in Table 5.

[0213] Table 5

[0214]

[0215]

[0216] 6. Synthesis Example 1: Synthesis of Compound A4:

[0217]

[0218] Under a nitrogen atmosphere, Sub-e1 (11.66 g, 26.25 mmol), RM-3 (8.60 g, 25 mmol), palladium acetate (Pd(OAc)2, 42 mg, 0.25 mmol), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (Xphos, 0.24 g, 0.5 mmol), anhydrous potassium carbonate (6.9 g, 50 mmol), tetrabutylammonium bromide (TBAB, 0.8 g, 2.5 mmol), toluene (120 mL), tetrahydrofuran (30 mL), and deionized water (30 mL) were added sequentially to a 250 mL three-necked flask. Stirring and heating were started, and the mixture was refluxed for 16 h. After the system cooled to room temperature, it was extracted with dichloromethane (100 mL × 3 times). The organic phases were combined, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by vacuum distillation to obtain the crude product. The crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as the mobile phase to obtain a yellow-green solid compound A4 (9.70 g, yield: 62%, m / z = 626.22 [M+H]). + ).

[0219] The compounds listed in Table 6 were synthesized using the same method as compound A4, except that reactant G was used instead of Sub-e1 and reactant H was used instead of RM-3. The main raw materials used, the synthesized compounds, their yields, and mass spectrometry data are shown in Table 6.

[0220] Table 6

[0221]

[0222]

[0223]

[0224]

[0225]

[0226]

[0227]

[0228]

[0229]

[0230] 7. Synthesis Example 53: Synthesis of Compound B1:

[0231]

[0232] Under a nitrogen atmosphere, RM-4 (8.04 g, 25 mmol), Sub-d1 (9.70 g, 27.5 mmol), tris(dibenzylacetone)palladium (0.916 g, 0.5 mmol), (2-dicyclohexylphosphine-2',4',6'triisopropylbiphenyl) (0.95 g, 1 mmol), sodium tert-butoxide (t-BuONa, 9.61 g, 50 mmol), and xylene (120 mL) were added sequentially to a 250 mL three-necked flask. The mixture was heated to reflux and stirred overnight. After the system cooled to room temperature, it was extracted with dichloromethane (100 mL × 3 times). The organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the solvent was removed by vacuum distillation to obtain the crude product. The crude product was purified by silica gel column chromatography using n-heptane / dichloromethane as the mobile phase to give a white solid compound B1 (11.48 g; yield: 72%, m / z = 638.24 [M+H]). + ).

[0233] The compounds listed in Table 7 were synthesized using the same method as compound B1, except that reactant J was used instead of Sub-d1 and reactant K was used instead of RM-4. The main raw materials used, the synthesized compounds, their yields, and mass spectrometry data are shown in Table 7.

[0234] Table 7

[0235]

[0236]

[0237]

[0238]

[0239]

[0240]

[0241]

[0242]

[0243]

[0244]

[0245]

[0246] The NMR data of some compounds are shown in Table 8:

[0247] Table 8

[0248]

[0249] Device Examples

[0250] Example 1: Red Organic Electroluminescent Device

[0251] The anode is prepared through the following process: [The anode thickness is...] On the ITO / Ag / ITO experimental substrate, surface treatment was performed using ultraviolet light, ozone, and O2:N2 plasma to increase the work function of the anode, and the surface of the experimental substrate was cleaned with organic solvents to remove impurities and oil stains.

[0252] On the anode substrate, compounds HT-1 and PD-1 were co-deposited at a deposition rate ratio of 98%:2% to form a layer with a thickness of [missing information]. Hole injection layer.

[0253] Compound HT-1 was deposited on the hole injection layer to form a thickness of [thickness value missing]. The hole transport layer.

[0254] Compound HT-2 was deposited on the hole transport layer to form a thickness of [missing information]. The light-emitting auxiliary layer.

[0255] On the light-emitting auxiliary layer, compounds A4, RH-P, and RD-1 of this application are co-deposited at a deposition rate ratio of 49%:49%:2% to form a layer with a thickness of [missing information]. The organic light-emitting layer.

[0256] On the organic light-emitting layer, compounds ET-1 and LiQ were co-deposited at a 1:1 evaporation rate ratio to form a layer with a thickness of [thickness missing]. The electron transport layer.

[0257] Yb is deposited on the electron transport layer to form a thickness of The electron injection layer.

[0258] On the electron-injected layer, magnesium (Mg) and silver (Ag) are co-deposited at a evaporation rate ratio of 1:9 to form a layer with a thickness of [thickness value missing]. The cathode.

[0259] Finally, compound CP-1 is deposited on the cathode to form a thickness of [thickness value missing]. An organic coating layer is applied to complete the fabrication of a red organic electroluminescent device.

[0260] Examples 2-52

[0261] Except that, when fabricating the organic light-emitting layer, the organic electroluminescent device was prepared using the same method as in Example 1, except that the compounds in Table 9 below were used instead of compound A4 in Example 1.

[0262] Comparative Examples 1-4

[0263] Except that when fabricating the organic light-emitting layer, compounds A, B, C, and D from Table 9 were used to replace compound A4 in Example 1, the organic electroluminescent device was prepared using the same method as in Example 1.

[0264] In the fabrication of organic electroluminescent devices, the structures of the various materials used in the comparative and examples are as follows:

[0265]

[0266] The performance of the red organic electroluminescent devices prepared in the examples and comparative examples was tested. The IVL performance (driving voltage, current efficiency, and color coordinates) of the devices was within 10 mA / cm². 2 Under the tested conditions, the lifetime of the T95 device is 20 mA / cm. 2 The test was conducted under the specified conditions, and the test results are shown in Table 9.

[0267] Table 9

[0268]

[0269]

[0270]

[0271] As can be seen from Table 9 above, when the organic compounds of this application are used as electron transport type red light host materials (RH-N), the efficiency is increased by at least 12.2% and the lifetime is increased by at least 14.9%.

[0272] Example 53: Red Organic Electroluminescent Device

[0273] The anode is prepared through the following process: [The anode thickness is...] On the ITO / Ag / ITO experimental substrate, surface treatment was performed using ultraviolet light, ozone, and O2:N2 plasma to increase the work function of the anode, and the surface of the experimental substrate was cleaned with organic solvents to remove impurities and oil stains.

[0274] On the anode substrate, compounds HT-1 and PD-1 were co-deposited at a deposition rate ratio of 98%:2% to form a layer with a thickness of [missing information]. Hole injection layer.

[0275] Compound HT-1 was deposited on the hole injection layer to form a thickness of [thickness value missing]. The hole transport layer.

[0276] Compound HT-2 was deposited on the hole transport layer to form a thickness of [missing information]. The light-emitting auxiliary layer.

[0277] On the light-emitting auxiliary layer, compounds B1, RH-N, and RD-1 of this application are co-deposited at a deposition rate ratio of 49%:49%:2% to form a layer with a thickness of [missing information]. The organic light-emitting layer.

[0278] On the organic light-emitting layer, compounds ET-1 and LiQ were co-deposited at a 1:1 evaporation rate ratio to form a layer with a thickness of [thickness missing]. The electron transport layer.

[0279] Yb is deposited on the electron transport layer to form a thickness of The electron injection layer.

[0280] On the electron-injected layer, magnesium (Mg) and silver (Ag) are co-deposited at a evaporation rate ratio of 1:9 to form a layer with a thickness of [thickness value missing]. The cathode.

[0281] Finally, compound CP-1 is deposited on the cathode to form a thickness of [thickness value missing]. An organic coating layer is applied to complete the fabrication of a red organic electroluminescent device.

[0282] Examples 54-116

[0283] Except that, when fabricating the organic light-emitting layer, the organic electroluminescent device was prepared using the same method as in Example 53, except that the compounds in Table 10 below were used instead of compound B1 in Example 53.

[0284] Comparative Examples 5-8

[0285] Except that when fabricating the organic light-emitting layer, compounds E, F, G, and H from Table 9 are used instead of compound B1 in Example 53, the organic electroluminescent device is prepared using the same method as in Example 53.

[0286] In the fabrication of organic electroluminescent devices, the structures of the various materials used in the comparative and examples are as follows:

[0287]

[0288]

[0289] The performance of the red organic electroluminescent devices prepared in the examples and comparative examples was tested. The IVL performance (driving voltage, current efficiency, and color coordinates) of the devices was within 10 mA / cm². 2 Under the tested conditions, the lifetime of the T95 device is 20 mA / cm. 2 The test was conducted under the specified conditions, and the test results are shown in Table 10.

[0290] Table 10

[0291]

[0292]

[0293] As shown in Table 10 above, when used as a hole-transmitting red light host material (RH-P), the efficiency is improved by at least 11.5% and the lifetime is improved by at least 15.3%.

[0294] As shown in Tables 9 and 10, when the organic compounds of this application are used as the host material for organic electroluminescent devices, the device performance is significantly improved compared to the comparative example compounds. The reason for this may be that, unlike compounds A to C and compounds F to H, the organic compounds of this application have different structures... The benzofuran skeleton structure possesses a suitable first excited triplet energy level, which differs from that of compounds D and E. The organic compounds of this application exhibit this skeleton structure. By attaching triazine or aromatic amine fragments to the benzene fragments, this specific connection method gives the constructed compound a larger overall conjugated area and increases the molecular conjugation length, which helps to enhance the packing between compound molecules and increase the charge carriers in the compound. Therefore, when this compound is used as an electron transport material or a hole transport material in a hybrid host material, it can improve the charge carrier balance in the light-emitting layer, widen the charge carrier recombination region, and improve the exciton generation and utilization efficiency, which is reflected in the improvement of device luminescence efficiency and lifetime.

[0295] The preferred embodiments of this application have been described in detail above. However, this application is not limited to the specific details of the above embodiments. Within the scope of the technical concept of this application, various simple modifications can be made to the technical solution of this application, and these simple modifications all fall within the protection scope of this application.

Claims

1. Organic compounds, among which, The organic compound has the structure shown in Formula 1: Among them, one of X1 and X2 is selected from O, and the other is selected from a single bond; R is selected from the structure shown in Formula 2-1 or the structure shown in Formula 2-2; L, L1, L2, L3, L4 and L5 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms. Ar1, Ar2, Ar3 and Ar4 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups with 6 to 40 carbon atoms, or substituted or unsubstituted heteroaryl groups with 3 to 40 carbon atoms. The substituents in L, L1, L2, L3, L4, L5, Ar1, Ar2, Ar3, and Ar4 may be the same or different, and each is independently selected from deuterium, cyano, halogen group, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, triarylsilyl with 12 to 24 carbon atoms, aryl with 6 to 20 carbon atoms, heteroaryl with 3 to 20 carbon atoms, or cycloalkyl with 3 to 10 carbon atoms; Each R1, each R2, each R3, and each R4 may be the same or different, and each is independently selected from hydrogen, deuterium, cyano, halogen group, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuteralkyl with 1 to 10 carbon atoms, aryl with 6 to 20 carbon atoms, deuteraryl with 6 to 20 carbon atoms, heteroaryl with 3 to 20 carbon atoms, or deuteraryheteraryl with 3 to 20 carbon atoms; a is the number of R1s, and a can be selected from 1, 2, 3 or 4; b is the number of R2s, and b can be selected from 1 or 2; c is the number of R3s, and c can be selected from 1, 2, 3 or 4; d is the number of R4s, and d can be selected from 1, 2, 3 or 4.

2. The organic compound according to claim 1, wherein, L, L1, and L2 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted arylene groups with 6 to 12 carbon atoms, or substituted or unsubstituted heteroarylene groups with 12 to 18 carbon atoms. The substituents in L, L1 and L2 may be the same or different, and each is independently selected from deuterium, halogen group, cyano, alkyl with 1 to 5 carbon atoms, deuterated alkyl with 1 to 5 carbon atoms, haloalkyl with 1 to 5 carbon atoms or phenyl; Optionally, Ar1 and Ar2 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups having 6 to 18 carbon atoms or substituted or unsubstituted heteroaryl groups having 12 to 18 carbon atoms; The substituents in Ar1 and Ar2 may be the same or different, and each is independently selected from deuterium, halogen group, cyano, alkyl with 1 to 5 carbon atoms, haloalkyl with 1 to 5 carbon atoms, deuteralkyl with 1 to 5 carbon atoms, aryl with 6 to 12 carbon atoms, heteroaryl with 5 to 12 carbon atoms, or trialkylsilyl with 3 to 9 carbon atoms; Optionally, L3, L4, and L5 may be the same or different, and each may be independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 12 carbon atoms, or substituted or unsubstituted heteroaryl groups with 12 to 18 carbon atoms. The substituents in L3, L4 and L5 may be the same or different, and each is independently selected from deuterium, halogen group, cyano, alkyl with 1 to 5 carbon atoms, deuterated alkyl with 1 to 5 carbon atoms, haloalkyl with 1 to 5 carbon atoms or phenyl; Optionally, Ar3 and Ar4 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups having 6 to 25 carbon atoms or substituted or unsubstituted heteroaryl groups having 12 to 18 carbon atoms; The substituents in Ar3 and Ar4 may be the same or different, and each is independently selected from deuterium, halogen groups, cyano, alkyl with 1 to 5 carbon atoms, haloalkyl with 1 to 5 carbon atoms, deuterated alkyl with 1 to 5 carbon atoms, aryl with 6 to 12 carbon atoms, heteroaryl with 5 to 12 carbon atoms, trialkylsilyl or triphenylsilyl with 3 to 9 carbon atoms.

3. The organic compound according to claim 1, wherein, L, L1, and L2 may be the same or different, and each is independently selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted dibenzofuranylene, a substituted or unsubstituted dibenzothiopheneylene, or a substituted or unsubstituted carbazolylene. The substituents in L, L1, and L2 may be the same or different, and each is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trideuterated methyl, trifluoromethyl, or phenyl. Optionally, L, L1, and L2 may be the same or different, and each may be independently selected from the group consisting of single bonds or the following groups:

4. The organic compound according to claim 1, wherein, L is selected from the group consisting of single bonds or the following groups: Optionally, L1 and L2 may be the same or different, and each is independently selected from the group consisting of single bonds or the following groups:

5. The organic compound according to claim 1, wherein, Ar1 and Ar2 may be the same or different, and each is independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl or substituted or unsubstituted carbazolyl. The substituents in Ar1 and Ar2 may be the same or different, and each is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, carbazoleyl or trimethylsilyl; Alternatively, Ar1 and Ar2 may be the same or different, and each may be independently selected from the group consisting of:

6. The organic compound according to claim 1, wherein, They may be the same or different, and each is independently selected from the group consisting of the following groups:

7. The organic compound according to claim 1, wherein, L3, L4, and L5 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, or substituted or unsubstituted carbazolyl. The substituents in L3, L4, and L5 may be the same or different, and each is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trideuterated methyl, trifluoromethyl, or phenyl. Optionally, L3, L4, and L5 may be the same or different, and each may be independently selected from the group consisting of single bonds or the following groups:

8. The organic compound according to claim 1, wherein, L5 is selected from the group consisting of single bonds or the following groups: Optionally, L3 and L4 may be the same or different, and each may be independently selected from the group consisting of single bonds or the following groups:

9. The organic compound according to claim 1, wherein, Ar3 and Ar4 may be the same or different, and each is independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl or substituted or unsubstituted carbazolyl; The substituents in Ar3 and Ar4 may be the same or different, and each is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, trimethylsilyl or triphenylsilyl. Alternatively, Ar3 and Ar4 may be the same or different, and each may be independently selected from the group consisting of:

10. The organic compound according to claim 1, wherein, They may be the same or different, and each is independently selected from the group consisting of the following groups:

11. The organic compound according to claim 1, wherein, The structure shown in Equation 2-1 is selected from the group consisting of the following structures: Optionally, the structure shown in Equation 2-2 is selected from the group consisting of the following structures:

12. The organic compound according to claim 1, wherein, The organic compound is selected from the following structures:

13. An organic electroluminescent device, comprising an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode, wherein, The functional layer comprises any one of the organic compounds according to claims 1 to 12.

14. The organic electroluminescent device according to claim 13, wherein, The organic electroluminescent device is a red organic electroluminescent device; Optionally, the functional layer includes an organic light-emitting layer containing the organic compound.

15. Electronic devices, wherein, Including the organic electroluminescent device as described in claim 13 or 14.

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