Organic compounds, organic electroluminescent devices, and electronic devices

Abstract

The application relates to an organic compound, an organic electroluminescence device and an electronic device. The organic compound provided by the application has a structure shown in formula I, and the application of the organic compound to an organic electroluminescence device can significantly improve the performance of the device.

Description

Technical Field

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

[0002] Organic electroluminescence displays (OLEDs) are current-driven semiconductor light-emitting devices based on organic materials. A typical structure consists of a layer of organic light-emitting material, tens of nanometers thick, fabricated on ITO glass as the organic light-emitting layer, with a low work function metal electrode on top. When a voltage is applied to the electrode, the light-emitting layer emits light. Unlike inorganic thin-film electroluminescent devices (TFELs), the electroluminescence of organic materials is an injection-type recombination light emission. Its light emission mechanism involves holes and electrons generated at the positive and negative electrodes recombinating into excitons within the light-emitting material. The excitons' energy is transferred to the light-emitting molecules, exciting electrons in the molecules to an excited state. Since the excited state is unstable, the process of returning from the excited state to the ground state produces visible light.

[0003] To enhance electron and hole injection and transport capabilities, an organic hole transport material is typically added between the ITO and the organic light-emitting layer, and / or an electron transport layer is added between the organic light-emitting layer and the metal electrode to improve luminous efficiency. Furthermore, during the fabrication of organic electroluminescent devices, defects in the organic electroluminescent material, electrode purity, and different material interfaces all significantly affect luminous intensity and overall performance.

[0004] Green light materials, one of the three primary colors, have seen rapid development in recent years. Triarylamine compounds are commonly chosen as the light-emitting modulating layer material for regulating hole transport and injection, and these compounds have been widely used due to their high hole mobility. However, these compounds still suffer from insufficient thermal stability and low glass transition temperatures, leading to fluorescence quenching and color coordinate drift, resulting in short device lifetimes. Furthermore, the triplet energy level (T1) of commonly used triarylamine compounds is relatively shallow, and their energy transfer efficiency needs improvement. Triphenylene oxide, due to its large planar conjugation properties and high mobility, has seen its derivatives increasingly used in the OLED field. However, the planar rigidity of its molecules can cause defects such as poor film formation and easy crystallization. Therefore, it is necessary to modify the rigidity of the molecular structure and increase the spatial distortion to solve these problems. Summary of the Invention

[0005] 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 performance of the device.

[0006] A first aspect of this application provides an organic compound having the structure shown in Formula I:

[0007]

[0008] Ar1 and Ar2 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.

[0009] L1 and L2 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, or substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms.

[0010] The substituents in L1, L2, Ar1, and Ar2 may be the same or different, and each is independently selected from deuterium, halogen groups, cyano, alkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, cycloalkyl with 3 to 10 carbon atoms, aryl with 6 to 20 carbon atoms, deuterated aryl with 6 to 20 carbon atoms, heteroaryl with 3 to 20 carbon atoms, deuterated heteroaryl with 3 to 20 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, or triarylsilyl with 18 to 24 carbon atoms;

[0011] Each of R1, R2, R3, R4, R5 and R6 may be the same or different, and each is independently selected from hydrogen, deuterium, halogen group, cyano, alkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms or trialkylsilyl with 3 to 12 carbon atoms;

[0012] n1 is the number of R1, and n1 is selected from 1, 2, 3, 4 or 5;

[0013] n2 is the number of R2, and n2 is selected from 1, 2, 3, 4 or 5;

[0014] n3 is the number of R3, and n3 is selected from 1 or 2;

[0015] n4 is the number of R4, and n4 is selected from 1, 2, 3 or 4;

[0016] n5 is the number of R5, and n5 is selected from 1, 2, 3 or 4;

[0017] n6 is the number of R6, and n5 is selected from 1, 2 or 3.

[0018] 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; the functional layer comprises the aforementioned organic compound.

[0019] A third aspect of this application provides an electronic device including the organic electroluminescent device described in the second aspect.

[0020] The organic compound of this application connects the nitrogen atom of a triphenylene group to the nitrogen atom of a secondary aromatic amine group via a para-positional phenyl group of a terphenyl group. The advantages of this structure are: due to the large π-electron delocalization system and high triplet energy level T1 of the triphenylene group, its para-positional connection with the nitrogen atom of the aromatic amine exhibits strong conjugation. This connection method improves both the hole mobility of the aromatic amine group and the electron blocking ability of the molecule, thus making this type of compound a light-emitting modulating layer material with hole transport properties. Furthermore, the aforementioned central benzene ring is a terphenyl group, and both the aromatic amine group on the central benzene ring and the ortho-position of the triphenylene group are connected to phenyl groups, which effectively improves the planar rigidity of the molecule and increases the molecular twist, thereby improving the film-forming properties of the molecule, reducing the evaporation temperature of the material, and also enhancing the mass production stability of the material. Specifically, when this structure is applied to the light-emitting modulating layer of OLED devices, it can improve the device efficiency and lifetime.

[0021] Other features and advantages of this application will be described in detail in the following detailed description section. Attached Figure Description

[0022] 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.

[0023] Figure 1 This is a schematic diagram of the structure of an organic electroluminescent device according to one embodiment of this application.

[0024] Figure 2 This is a schematic diagram of an electronic device according to one embodiment of this application.

[0025] Figure Labels

[0026] 100, Anode 200, Cathode 300, Functional Layer 310, Hole Injection Layer

[0027] 320. Hole transport layer; 321. Light emission adjustment layer; 330. Organic light emission layer; 341. Hole blocking layer

[0028] 340, Electron transport layer; 350, Electron injection layer; 400, Electronic device Detailed Implementation

[0029] 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 to make this application more comprehensive and complete, and to 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.

[0030] In this application, the descriptive phrases "each...independently is," "...each independently is," and "...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.

[0031] 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, deuterated alkyl, haloalkyl, cycloalkyl, aryl, heteroaryl, deuterated aryl, deuterated heteroaryl, trialkylsilyl, triarylsilyl, etc. The number of substituents can be one or more.

[0032] 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.

[0033] 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).

[0034]

[0035] 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.

[0036]

[0037] 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).

[0038]

[0039] In this application, the number of carbon atoms in L1, L2, Ar1, Ar2, R1, R2, R3, R4, and R5 refers to the total number of carbon atoms. For example, if L1 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.

[0040] In this application, "alkyl" can include straight-chain alkyl or branched alkyl. An alkyl group can 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.

[0041] In this application, cycloalkyl 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.

[0042] 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. This includes aryl groups, but partially hydrogenated aryl groups are not included. Examples of partially hydrogenated aryl groups include, but are not limited to, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydroindyl, substituted or unsubstituted acenaphthel, 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, etc. In this application, biphenyl can be understood as a phenyl-substituted aryl group or an unsubstituted aryl group.

[0043] In this application, the term "arylene" refers to a divalent group formed by the further loss of a hydrogen atom from an aryl group.

[0044] 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, deuterated aryl, deuterated heteroaryl, trialkylsilyl, or triarylsilyl group. It is understood that the number of carbon atoms in the 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.

[0045] In this application, aryl groups used as substituents include, but are not limited to, phenyl, naphthyl, and biphenyl groups.

[0046] 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.

[0047] In this application, terphenyl includes

[0048] 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.

[0049] 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.

[0050] In this application, the substituted heteroaryl group can 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, deuterated aryl, deuterated heteroaryl, trialkylsilyl, triarylsilyl, etc.

[0051] 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.

[0052] In this application, the heteroaryl group used as a substituent includes, but is not limited to, dibenzofuranyl, dibenzothiophenyl, carbazoyl, etc.

[0053] In this application, hydrogen atoms include isotopes of H, namely hydrogen (H), deuterium (D) and tritium (T).

[0054] 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.

[0055] In this application, the halogen group can be fluorine, chlorine, bromine, or iodine.

[0056] 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.

[0057] 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.

[0058] In this application, specific examples of trialkylsilyl groups include, but are not limited to, trimethylsilyl groups.

[0059] In this application, specific examples of triarylsilyl groups include, but are not limited to, triphenylsilyl groups.

[0060] 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.

[0061] 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.

[0062] In this application, It represents a chemical bond that connects to other groups.

[0063] In a first aspect, this application provides an organic compound having the structure shown in Formula I:

[0064]

[0065] Ar1 and Ar2 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.

[0066] L1 and L2 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, or substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms.

[0067] The substituents in L1, L2, Ar1, and Ar2 may be the same or different, and each is independently selected from deuterium, halogen groups, cyano, alkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, cycloalkyl with 3 to 10 carbon atoms, aryl with 6 to 20 carbon atoms, deuterated aryl with 6 to 20 carbon atoms, heteroaryl with 3 to 20 carbon atoms, deuterated heteroaryl with 3 to 20 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, or triarylsilyl with 18 to 24 carbon atoms;

[0068] Each of R1, R2, R3, R4, R5 and R6 may be the same or different, and each is independently selected from hydrogen, deuterium, halogen group, cyano, alkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms or trialkylsilyl with 3 to 12 carbon atoms;

[0069] n1 is the number of R1, and n1 is selected from 1, 2, 3, 4 or 5;

[0070] n2 is the number of R2, and n2 is selected from 1, 2, 3, 4 or 5;

[0071] n3 is the number of R3, and n3 is selected from 1 or 2;

[0072] n4 is the number of R4, and n4 is selected from 1, 2, 3 or 4;

[0073] n5 is the number of R5, and n5 is selected from 1, 2, 3 or 4;

[0074] n6 is the number of R6, and n5 is selected from 1, 2 or 3.

[0075] In some embodiments, Ar1 and Ar2 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. For example, Ar1 and Ar2 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24 or 25 carbon atoms, or substituted or unsubstituted heteroaryl groups having 12, 13, 14, 15, 16, 17 or 18 carbon atoms.

[0076] 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, cycloalkyl with 5 to 10 carbon atoms, haloalkyl with 1 to 5 carbon atoms, deuterated alkyl with 1 to 5 carbon atoms, aryl with 6 to 12 carbon atoms, deuterated aryl with 6 to 12 carbon atoms, heteroaryl with 5 to 12 carbon atoms, trialkylsilyl or triphenylsilyl with 3 to 9 carbon atoms.

[0077] In some embodiments, 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 fluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, or substituted or unsubstituted carbazoleyl.

[0078] 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, cyclohexyl, cyclopentyl, adamantyl, trifluoromethyl, trideuterated methyl, phenyl, naphthyl, pentadeuterated phenyl, heptadeuterated naphthyl, dibenzofuranyl, dibenzothiophenyl, carbazoyl, trimethylsilyl, or triphenylsilyl.

[0079] In some embodiments, Ar1 and Ar2 may be the same or different, and each is independently selected from the group consisting of:

[0080]

[0081] In some embodiments, Ar1 and Ar2 may be the same or different, and each is independently selected from the group consisting of:

[0082]

[0083]

[0084] In some embodiments, L1 and L2 may be the same or different, and each is independently selected from single-bonded substituted or unsubstituted aryl groups having 6 to 18 carbon atoms, or substituted or unsubstituted heteroaryl groups having 12 to 18 carbon atoms. For example, L1 and L2 may be the same or different, and each is independently selected from single-bonded substituted or unsubstituted aryl groups having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17 or 18 carbon atoms, or substituted or unsubstituted heteroaryl groups having 12, 13, 14, 15, 16, 17 or 18 carbon atoms.

[0085] Optionally, the substituents in L1 and L2 may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, alkyl with 1 to 5 carbon atoms, deuterated alkyl with 1 to 5 carbon atoms, haloalkyl with 1 to 5 carbon atoms, aryl with 6 to 12 carbon atoms, deuterated aryl with 6 to 12 carbon atoms, or trialkylsilyl with 3 to 9 carbon atoms.

[0086] In some embodiments, L1 and L2 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 fluorene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, or substituted or unsubstituted carbazolyl.

[0087] Optionally, the substituents in 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, phenyl, pentadeuterated phenyl or trimethylsilyl.

[0088] In some embodiments, 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, 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]

[0093] In some implementations... They may be the same or different, and each is independently selected from the group consisting of the following groups:

[0094]

[0095] In some implementations... They may be the same or different, and each is independently selected from the group consisting of the following groups:

[0096]

[0097]

[0098] In some implementations, the formula in Equation 1 Selected from groups consisting of the following structures:

[0099]

[0100]

[0101] In some embodiments, each of R1, R2, R3, R4, R5 and R6 may be the same or different, and each is independently selected from hydrogen (H), deuterium (D), 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 trialkylsilyl with 3 to 6 carbon atoms.

[0102] In some embodiments, each of R1, R2, R3, R4, R5 and R6 may be the same or different, and each is independently selected from hydrogen (H), deuterium (D), fluorine, cyano, methyl, ethyl, isopropyl, n-propyl, tert-butyl, isobutyl, n-butyl, trifluoromethyl, trideuterated methyl or trimethylsilyl.

[0103] In some implementations, formula I is selected from the structure shown in formula A or formula B:

[0104]

[0105] The definitions of L1, L2, Ar1, Ar2, each R1, each R2, each R3, each R4, each R5, R6, n1, n2, n3, n4, n5, and n6 are the same as in Equation 1.

[0106] Specifically, the organic compound represented by Formula I is selected from the group consisting of the compounds shown in claim 8.

[0107] In a second aspect, this application provides 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; the functional layer comprises the organic compound of this application.

[0108] Optionally, the functional layer of the organic electroluminescent device includes a light-emitting adjustment layer, which contains the organic compound of this application.

[0109] In this application, the organic electroluminescent device can be a blue organic electroluminescent device, a red organic electroluminescent device, or a green organic electroluminescent device.

[0110] Optionally, the above-mentioned organic electroluminescent device is a green organic electroluminescent device.

[0111] In one embodiment, the organic electroluminescent device described in this application, such as... Figure 1 As shown, the organic electroluminescent device may include an anode 100, a hole injection layer 310, a hole transport layer 320, a light-emitting adjustment layer 321, an organic light-emitting layer 330, a hole blocking layer 341, an electron transport layer 340, an electron injection layer 350, and a cathode 200 stacked together.

[0112] Optionally, the anode 100 comprises an anode material, preferably one with a high 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.

[0113] Optionally, the hole transport layer 320 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:

[0114]

[0115]

[0116] In one specific implementation, the hole transport layer 320 is HT-1.

[0117] In one specific embodiment, the light-emitting adjustment layer 321 is an organic compound represented by Formula I of this application.

[0118] Optionally, the organic light-emitting layer 330 may be composed of a single light-emitting layer 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.

[0119] The host material of the organic light-emitting layer 330 can be a metal chelate compound, a bis(styrene) derivative, an aromatic amine derivative, a dibenzofuran derivative, or other types of materials; this application does not impose any special restrictions on this. The host material can be a single host material or a mixture of host materials.

[0120] In one specific embodiment, the main material of the organic light-emitting layer 330 is p-GH-1 and n-GH-1 composition.

[0121] The guest material of the organic light-emitting layer 330 can be selected with reference to existing technologies, such as iridium (III) organometallic complexes, platinum (II) organometallic complexes, ruthenium (II) complexes, etc. Specific examples of the guest material include, but are not limited to:

[0122]

[0123]

[0124] In one specific embodiment, the guest material of the organic light-emitting layer 330 is GD-1.

[0125] 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 include metal complexes and / or nitrogen-containing heterocyclic derivatives. The metal complex material may be selected from, for example, LiQ, Alq3, etc. The nitrogen-containing heterocyclic derivative may be an aromatic ring with a nitrogen-containing six-membered or five-membered ring skeleton, a fused aromatic ring compound with a nitrogen-containing six-membered 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 nitrogen-containing heterocyclic derivatives used for electron transport materials include, but are not limited to:

[0126]

[0127] In one specific embodiment, the electron transport layer 340 is composed of ET-1 and LiQ.

[0128] 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.

[0129] Optionally, such as Figure 1 As shown, a hole injection layer 310 is further disposed between the anode 100 and the hole transport layer 320 to enhance the ability to inject holes into the hole transport layer 320. 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. For example, the compounds contained in the hole injection layer 310 are selected from the group consisting of the following compounds:

[0130]

[0131] In one specific embodiment, the hole injection layer 310 is composed of HT-1 and PD-1.

[0132] Optionally, such as Figure 1 As shown, a hole blocking layer 341 is disposed between the organic light-emitting layer 330 and the electron transport layer 340. The hole blocking layer 341 includes one or more hole blocking materials, which are not specifically limited in this application.

[0133] In one specific embodiment, the hole-blocking layer 341 is compound HB-1.

[0134] 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).

[0135] Optionally, the cathode 200 also has an organic coating.

[0136] In one specific embodiment, the organic coating layer comprises compound CP-1.

[0137] Thirdly, this application provides an electronic device including the organic electroluminescent device provided in the second aspect of this application.

[0138] According to one implementation method, such as Figure 2 As shown, the electronic device is a first electronic device 400, which includes the aforementioned organic electroluminescent device. The first 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.

[0139] The following examples illustrate the synthesis methods of the organic compounds described in this application, but this application is not limited in any way as a result.

[0140] Compounds synthesized using methods not mentioned in this application are all raw material products obtained through commercial means.

[0141] 1.1 Synthesis of intermediates Sub-DBP-b and Sub-DBP-c

[0142]

[0143] (1) Under nitrogen protection, the intermediate raw material Sub-DBP-a (100.0 g, 253.98 mmol), triphenyl-2-boronic acid (69.11 g, 253.98 mmol), tetra(triphenylphosphine)palladium (5.87 g, 5.08 mmol), tetrabutylammonium bromide (TBAB, 16.54 g, 51.30 mmol), potassium carbonate (77.22 g, 558.76 mmol), toluene (1000 mL), ethanol (500 mL), and water (250 mL) were added to the reaction flask. After the addition was complete, the mixture was stirred and heated to 70℃~75℃ and refluxed for 12 h. The reaction was stopped, cooled to room temperature, and extracted with dichloromethane. The organic phase was washed with water until neutral, dried with anhydrous magnesium sulfate, filtered, and the solvent was removed by vacuum distillation. The sample was purified by recrystallization from ethyl acetate / petroleum ether and dried to give a pale yellow solid Sub-DBP-b (90.06 g, yield: 71.4%).

[0144]

[0145] (2) The intermediate Sub-DBP-c was prepared by the same synthetic method as that for intermediate Sub-DBP-b, except that phenyl-1-boronic acid was replaced with phenyl-2-boronic acid, and other conditions remained unchanged, to obtain intermediate Sub-DBP-c (50.93 g, yield: 67.3%).

[0146] 1.2 Synthesis of intermediate IM-AH-1

[0147]

[0148] Under nitrogen protection, Sub-DBP-b (88.0 g, 177.19 mmol), phenylboronic acid (47.53 g, 389.83 mmol), tetra(triphenylphosphine)palladium (10.24 g, 8.86 mmol), tetrabutylammonium bromide (22.85 g, 70.88 mmol), potassium carbonate (97.95 g, 708.78 mmol), toluene (900 mL), ethanol (450 mL), and water (220 mL) were added to a reaction flask. After the addition was complete, stirring was started, and the mixture was heated to 70-75 °C and refluxed for 8 h. The reaction was stopped, cooled to room temperature, and extracted with dichloromethane. The organic phase was washed with water until neutral, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by vacuum distillation. The product was purified by recrystallization from toluene / petroleum ether and dried to give a white solid IM-AH-1 (68.91 g, yield: 79.2%).

[0149] 1.3 Synthesis of intermediates IM-AH-2 and IM-AH-3

[0150] IM-AH-2 and IM-AH-3 in Table 1 were synthesized using the same method as IM-AH-1, with the difference that raw material 1 was used instead of Sub-DBP-b, and raw material 2 was used instead of phenylboronic acid. The main raw materials used, the intermediates synthesized, and the overall yield of the final step are listed in Table 1.

[0151] Table 1

[0152]

[0153]

[0154] 2.1 Synthesis of intermediate IM-DAN-1

[0155]

[0156] Under nitrogen protection, 4-bromo-9,9-spirodifluorene (10.0 g, 25.30 mmol), 2-naphthylamine (3.8 g, 26.56 mmol), tris(dibenzylacetone)palladium (0.23 g, 0.25 mmol), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (0.24 g, 0.51 mmol), sodium tert-butoxide (3.65 g, 37.95 mmol), and toluene (100 mL) were added to a reaction flask. The mixture was stirred and heated to 108 °C for 4 h. After cooling to room temperature, the reaction solution was washed with water and dried with anhydrous magnesium sulfate. After filtration, the solvent was removed from the filtrate under reduced pressure to obtain a yellow solid crude product. The crude product was then purified by recrystallization using toluene / petroleum ether to obtain intermediate IM-DAN-1 (9.78 g, yield: 84.5%).

[0157] IM-DAN-x in Table 1 was synthesized using the same method as IM-DAN-1, with the difference that 4-bromo-9,9-spirodifluorene and 2-naphthylamine were replaced with starting material 3. The main starting materials, intermediates, and overall yield of the final step are listed in Table 2.

[0158] Table 2

[0159]

[0160]

[0161] 3.1 Synthesis Example 1: Synthesis of Compound 44

[0162]

[0163] Under nitrogen protection, intermediates IM-AH-1 (6.00 g, 12.22 mmol), IM-DAN-1 (5.59 g, 12.22 mmol), tris(dibenzylacetone)dipalladium (0.11 g, 0.12 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (0.10 g, 0.24 mmol), and sodium tert-butoxide (1.76 g, 18.33 mmol) were added to toluene (60 mL), heated to 108 °C, and stirred for 8 h. The mixture was then cooled to room temperature, washed with water until neutral, dried over magnesium sulfate, filtered, and the solvent was removed from the filtrate under reduced pressure. The crude product was purified by recrystallization from toluene / cyclohexane to give a white solid compound 44 (3.83 g, yield: 34.4%), mass spectrometry (m / z) = 912.36 [M+H]. + .

[0164] 3.2 Synthesis Example 2 to Synthesis Example 29:

[0165] The compounds listed in Table 3 were synthesized using the same method as compound 44, with the difference that starting material 5 was used instead of IM-AH-1, and starting material 6 (some of which are commercially available but not listed in Table 2) was used instead of IM-DAN-1. The main starting materials used, the structures of the product compounds, and their yields are listed in Table 3.

[0166] Table 3

[0167]

[0168]

[0169]

[0170]

[0171] 4. NMR data for some compounds are shown in Table 4:

[0172] Table 4

[0173]

[0174] Fabrication and evaluation of organic electroluminescent devices

[0175] Example 1: Green Organic Electroluminescent Device

[0176] 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.

[0177] On the anode substrate, compounds HT-1 and PD-1 were co-deposited at a deposition rate ratio of 97%:3% to form a layer with a thickness of [missing information]. Hole injection layer.

[0178] Compound HT-1 was deposited on the hole injection layer to form a thickness of [thickness value missing]. The hole transport layer.

[0179] Compound 2 is deposited on the hole transport layer to form a thickness of [thickness value missing]. The light-emitting adjustment layer.

[0180] On the light-emitting adjustment layer, compounds p-GH-1, n-GH-1, and GD-1 were co-deposited at a deposition rate ratio of 63%:37%:10% to form a layer with a thickness of [missing information]. The organic light-emitting layer.

[0181] Compound HB-1 was deposited on the organic light-emitting layer to form a thickness of [missing information]. Hole-blocking layer.

[0182] On the hole-blocking layer, compounds ET-1 and LiQ were co-deposited at a 50%:50% evaporation rate ratio to form a layer with a thickness of [missing information]. The electron transport layer.

[0183] Ytterbium (Yb) is deposited on the electron transport layer to form a thickness of [missing information]. The electron injection layer.

[0184] On the electron-injected layer, magnesium (Mg) and silver (Ag) are co-deposited at a deposition rate of 10%:90% to form a layer with a thickness of [thickness value missing]. The cathode.

[0185] Finally, compound CP-1 is deposited on the cathode to form a thickness of [thickness value missing]. The organic coating layer is used to complete the fabrication of green organic electroluminescent devices.

[0186] Examples 2 to 29:

[0187] Organic electroluminescent devices were prepared using the same method as in Example 1, except that when preparing the luminescence adjustment layer, the luminescence adjustment layer material in Table 5 was used to replace compound 2 in Example 1.

[0188] Comparative Examples 1 to 7:

[0189] Organic electroluminescent devices were prepared using the same method as in Example 1, except that when preparing the luminescence adjustment layer, compounds A, B, C, D, E, F, and G from Table 5 were used to replace compound 2 in Example 1.

[0190] In the fabrication of organic electroluminescent devices, the structures of the various materials used in the comparative and examples are as follows:

[0191]

[0192] The performance of the green organic electroluminescent devices prepared in Examples 1-29 and Comparative Examples 1-7 was tested, specifically at 15 mA / cm². 2 The IVL performance of the device was tested under the condition of 20 mA / cm. 2 The lifetime of the T95 device was tested under the following conditions, and the test results are shown in Table 5 below.

[0193] Table 5

[0194]

[0195]

[0196] As can be seen from Table 5 above, compared with the organic electroluminescent devices of Comparative Examples 1 to 7, the organic electroluminescent devices of Examples 1 to 29 have significantly improved performance, mainly manifested in the following: the operating voltage of the device is reduced by at least 0.13V, the current efficiency is increased by at least 13.6%, and the T95 lifetime is increased by at least 16.1%.

[0197] The reason for this may be that, compared with the structures of the compounds in Comparative Examples 1-7, the organic compounds of this application... The core structure comprises 2,5-diphenyl-4-triphenylene with specific substitution positions, and a diarylamine group directly connected to the N atom of the benzene ring at the para-position of the triphenylene group. In this structure, the N atoms of both the triphenylene group and the aromatic amine are in the para position. This connection enhances the conjugation properties of the compound, resulting in excellent hole transport properties and high negative charge carrier blocking ability with high hole mobility. Simultaneously, the two benzene ring substituents at the 2,5- and 3,5-positions of the triphenylene group, with their asymmetric configuration, ensure that either the N atom of the aromatic amine or the ortho position of the triphenylene group has a phenyl substituent. This structural design increases molecular twist, thereby improving the stability of the material when used in the evaporation process of OLED devices. Therefore, when the organic compound of this application is used as the luminescence adjustment layer in a device, the device performance is significantly improved.

[0198] 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. An organic compound, characterized in that, The organic compound has the structure shown in Formula I: Ar1 and Ar2 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. L1 and L2 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, or substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms. The substituents in L1, L2, Ar1, and Ar2 may be the same or different, and each is independently selected from deuterium, halogen groups, cyano, alkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, cycloalkyl with 3 to 10 carbon atoms, aryl with 6 to 20 carbon atoms, deuterated aryl with 6 to 20 carbon atoms, heteroaryl with 3 to 20 carbon atoms, deuterated heteroaryl with 3 to 20 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, or triarylsilyl with 18 to 24 carbon atoms; Each of R1, R2, R3, R4, R5 and R6 may be the same or different, and each is independently selected from hydrogen, deuterium, halogen group, cyano, alkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms or trialkylsilyl with 3 to 12 carbon atoms; n1 is the number of R1, and n1 is selected from 1, 2, 3, 4 or 5; n2 is the number of R2, and n2 is selected from 1, 2, 3, 4 or 5; n3 is the number of R3, and n3 is selected from 1 or 2; n4 is the number of R4, and n4 is selected from 1, 2, 3 or 4; n5 is the number of R5, and n5 is selected from 1, 2, 3 or 4; n6 is the number of R6, and n5 is selected from 1, 2 or 3.

2. The organic compound according to claim 1, characterized in that, Ar1 and Ar2 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups with 6 to 25 carbon atoms, or substituted or unsubstituted heteroaryl groups with 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 groups, cyano, alkyl with 1 to 5 carbon atoms, cycloalkyl with 5 to 10 carbon atoms, haloalkyl with 1 to 5 carbon atoms, deuterated alkyl with 1 to 5 carbon atoms, aryl with 6 to 12 carbon atoms, deuterated aryl with 6 to 12 carbon atoms, heteroaryl with 5 to 12 carbon atoms, trialkylsilyl or triphenylsilyl with 3 to 9 carbon atoms; Optionally, L1 and L2 may be the same or different, and each may be independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 18 carbon atoms, or substituted or unsubstituted heteroaryl groups with 12 to 18 carbon atoms. The substituents in L1 and L2 may be the same or different, and each is independently selected from deuterium, fluorine, cyano, alkyl with 1 to 5 carbon atoms, deuterated alkyl with 1 to 5 carbon atoms, haloalkyl with 1 to 5 carbon atoms, aryl with 6 to 12 carbon atoms, deuterated aryl with 6 to 12 carbon atoms, or trialkylsilyl with 3 to 9 carbon atoms; Optionally, each of R1, R2, R3, R4, R5 and R6 may be the same or different, and each may be independently selected from hydrogen, 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 trialkylsilyl with 3 to 6 carbon atoms.

3. The organic compound according to claim 1, characterized in that, 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 fluorenyl, substituted or unsubstituted spirodifluorenyl, 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, cyclohexyl, cyclopentyl, adamantyl, trifluoromethyl, trideuterated methyl, phenyl, naphthyl, pentadeuterated phenyl, heptadeuterated naphthyl, dibenzofuranyl, dibenzothiopheneyl, carbazoleyl, trimethylsilyl, or triphenylsilyl.

4. The organic compound according to claim 1, characterized in that, Ar1 and Ar2 may be the same or different, and each is independently selected from the group consisting of the following groups:

5. The organic compound according to claim 1, characterized in that, 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 fluorene, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiopheneyl, or a substituted or unsubstituted carbazolyl. The substituents in 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, phenyl, pentadeuterated phenyl, or trimethylsilyl.

6. The organic compound according to claim 1, characterized in that, 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:

7. The organic compound according to claim 1, characterized in that, They may be the same or different, and each is independently selected from the group consisting of the following groups: Optionally, in Equation 1 Selected from the group consisting of the following groups:

8. The organic compound according to claim 1, characterized in that, The organic compound is selected from the group consisting of the following compounds:

9. 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; characterized in that, The functional layer comprises any one of the organic compounds according to claims 1 to 8.

10. The organic electroluminescent device according to claim 9, characterized in that, The functional layer includes a light-emitting adjustment layer, which contains the aforementioned organic compound.

11. An electronic device comprising the organic electroluminescent device of claim 9 or 10.

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