Organic compounds, organic electroluminescent devices, and electronic devices

Abstract

The present application relates to the technical field of organic electroluminescent material, and provides an organic compound, an organic electroluminescent device and an electronic device.The organic compound has a structure as shown in formula 1, and the application of the arylamine organic compound to the organic electroluminescent device can significantly improve the performance of the device.

Description

Technical Field

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

[0002] With the development of electronic technology and the advancement of materials science, the application range of electronic components used to achieve electroluminescence or photoelectric conversion is becoming increasingly wide. 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 and generally includes 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 between the two electrodes. Under the influence of the 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. The excitons are in an excited state and release energy outward, thereby causing the electroluminescent layer to emit light.

[0003] The main problems with existing organic electroluminescent devices are lifespan and efficiency. As displays become larger, driving voltages also increase, and luminous efficiency and current efficiency need to be improved. Therefore, it is necessary to continue to develop new materials to further improve the performance of organic electroluminescent devices. Summary of the Invention

[0004] In view of the above-mentioned problems existing in the prior art, the purpose of the present invention is to provide an organic compound and an organic electroluminescent device and electronic device containing the same, wherein the organic compound used in the organic electroluminescent device can improve the performance of the device.

[0005] According to a first aspect of the present invention, a compound is provided having the structure shown in Formula 1:

[0006]

[0007] Among them, R1, R2, R3 and R4 may be the same or different, and are independently selected from substituted or unsubstituted aryl groups with 6 to 24 carbon atoms and substituted or unsubstituted alkyl groups with 1 to 10 carbon atoms;

[0008] L, L1, and L2 may be the same or different, and are 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.

[0009] Ar1 and Ar2 may be the same or different, and are each 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.

[0010] The substituents in R1, R2, R3, and R4 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, deuteryl with 1 to 10 carbon atoms, aryl with 6 to 15 carbon atoms, haloaryl with 6 to 15 carbon atoms, deuteryl with 6 to 15 carbon atoms, and heteroaryl with 3 to 12 carbon atoms;

[0011] The substituents in Ar1, Ar2, L, L1, and L2 may be the same or different, and each is independently selected from deuterium, cyano, halogen groups, alkyl groups with 1 to 10 carbon atoms, haloalkyl groups with 1 to 10 carbon atoms, deuterated alkyl groups with 1 to 10 carbon atoms, trialkylsilyl groups with 3 to 12 carbon atoms, aryl groups with 6 to 20 carbon atoms, haloaryl groups with 6 to 20 carbon atoms, deuterated aryl groups with 6 to 20 carbon atoms, heteroaryl groups with 3 to 20 carbon atoms, cycloalkyl groups with 3 to 10 carbon atoms, alkoxy groups with 1 to 10 carbon atoms, alkylthio groups with 1 to 10 carbon atoms, aryloxy groups with 6 to 20 carbon atoms, or arylthio groups with 6 to 20 carbon atoms; optionally, any two adjacent substituents in Ar1, Ar2, L, L1, and L2 may form a saturated or unsaturated 3 to 15-membered ring.

[0012] Each R5 is independently selected from deuterium, cyano, halogen group, alkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, aryl with 6 to 20 carbon atoms, haloaryl 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, and haloheteroaryl with 3 to 20 carbon atoms; n5 is the number of R5, and n5 is selected from 0, 1, 2, 3, 4, 5, or 6.

[0013] According to a second aspect of the present invention, 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 aforementioned organic compound.

[0014] According to a third aspect of the present invention, an electronic device is provided, comprising the organic electroluminescent device described in the second aspect.

[0015] This invention provides an organic compound containing an acenaphthene-derived group with aryl or alkyl substitution. In this organic compound, the active hydrogens at the 1,2-positions of acenaphthene are replaced by alkyl or aryl groups, thereby effectively improving the chemical stability of the molecule. Based on the conjugation effect between the acenaphthene-derived group and the aromatic amino group, the hole mobility of the material can be effectively improved, making it suitable as a hole transport layer for organic electroluminescent devices. This results in organic electroluminescent devices prepared from it exhibiting low voltage and high efficiency. Furthermore, by introducing at least one aryl or alkyl group onto the acenaphthene-derived group, a structure containing multiple substituents is formed. These substituents are distributed on both sides of the acenaphthene plane, reducing intermolecular stacking in space, thereby improving the amorphous morphology of the material during film formation and enhancing its stability when used in organic electroluminescent devices. When the organic compound of this invention is used as a second hole transport layer material in an organic electroluminescent device, device products with low voltage, high efficiency, and long lifetime can be prepared. Attached Figure Description

[0016] The accompanying drawings are provided to further illustrate the invention and form part of the specification. They are used together with the following detailed description to explain the invention, but do not constitute a limitation thereof.

[0017] Figure 1 This is a schematic diagram of the structure of an organic electroluminescent device according to one embodiment of the present invention.

[0018] Figure 2 This is a schematic diagram of the structure of an electronic device according to one embodiment of the present invention.

[0019] Figure Labels

[0020] 100, Anode 200, Cathode 300, Functional Layer 310, Hole Injection Layer

[0021] 321. First hole transport layer; 322. Second hole transport layer; 330. Organic light-emitting layer; 331. Hole blocking layer.

[0022] 340, Electron transport layer; 350, Electron injection layer; 400, Electronic device Detailed Implementation

[0023] 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 the invention 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 the invention.

[0024] In a first aspect, the present invention provides a compound having the structure shown in Formula 1:

[0025]

[0026] Among them, R1, R2, R3 and R4 may be the same or different, and are independently selected from substituted or unsubstituted aryl groups with 6 to 24 carbon atoms and substituted or unsubstituted alkyl groups with 1 to 10 carbon atoms.

[0027] L, L1, and L2 may be the same or different, and are 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.

[0028] Ar1 and Ar2 may be the same or different, and are each 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.

[0029] The substituents in R1, R2, R3, and R4 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, deuteryl with 1 to 10 carbon atoms, aryl with 6 to 15 carbon atoms, haloaryl with 6 to 15 carbon atoms, deuteryl with 6 to 15 carbon atoms, and heteroaryl with 3 to 12 carbon atoms.

[0030] The substituents in Ar1, Ar2, L, L1, and L2 may be the same or different, and each is independently selected from deuterium, cyano, halogen groups, alkyl groups with 1 to 10 carbon atoms, haloalkyl groups with 1 to 10 carbon atoms, deuterated alkyl groups with 1 to 10 carbon atoms, trialkylsilyl groups with 3 to 12 carbon atoms, aryl groups with 6 to 20 carbon atoms, haloaryl groups with 6 to 20 carbon atoms, deuterated aryl groups with 6 to 20 carbon atoms, heteroaryl groups with 3 to 20 carbon atoms, cycloalkyl groups with 3 to 10 carbon atoms, alkoxy groups with 1 to 10 carbon atoms, alkylthio groups with 1 to 10 carbon atoms, aryloxy groups with 6 to 20 carbon atoms, or arylthio groups with 6 to 20 carbon atoms; optionally, any two adjacent substituents in Ar1, Ar2, L, L1, and L2 may form a saturated or unsaturated 3 to 15-membered ring.

[0031] Each R5 is independently selected from deuterium, cyano, halogen group, alkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, aryl with 6 to 20 carbon atoms, haloaryl 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, and haloheteroaryl with 3 to 20 carbon atoms; n5 is the number of R5, and n5 is selected from 0, 1, 2, 3, 4, 5, or 6.

[0032] In this invention, in Formula 1, square brackets “[]” indicate that group L can be attached to the structure. L can be attached to any of the R1, R2, R3, R4 and the naphthalene ring. At any position indicated by 1, 2, 3, 4, 5, a, b, c, d, e. Specifically, The structure can include the following connection methods:

[0033]

[0034] In this invention, the site number of dihydroacenaphthene is...

[0035] In this invention, the terms "optional" or "optionally" mean that the event or environment described below may or may not occur, and the description includes the scenarios in which the event or environment occurs or does not occur. For example, "optionally, any two adjacent substituents form a ring" means that the two substituents may or may not form a ring, that is, it includes both the scenario where two adjacent substituents form a ring and the scenario where two adjacent substituents do not form a ring. As another example, "any two adjacent substituents among Ar1, Ar2, L, L1, and L2 form a saturated or unsaturated 3- to 15-membered ring" means that any two adjacent substituents among Ar1, Ar2, L, L1, and L2 are connected to each other to form a ring, or any two adjacent substituents among Ar1, Ar2, L, L1, and L2 may also exist independently.

[0036] In this invention, "any two adjacent substituents forming a ring" can include two substituents on the same atom, or one substituent on each of two adjacent atoms. When two substituents are on the same atom, the two substituents can form a saturated or unsaturated ring together with the atom they are connected to. When one substituent is on each of two adjacent atoms, the two substituents can fuse into a ring. For example, when Ar1 has two or more substituents, the ring formed by any two adjacent substituents is a saturated or unsaturated cyclic group, such as: benzene ring, naphthalene ring, phenanthrene ring, anthracene ring, fluorene ring, cyclopentane, cyclohexane, adamantane, etc.

[0037] In this invention, the descriptive phrases "each...independently is," "...each independently is," and "...each independently is" 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.

[0038] In this invention, 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 substituents mentioned above, i.e., Rc, can be, for example, deuterium, halogen groups, cyano, alkyl, cycloalkyl, aryl, heteroaryl, deuterated aryl, haloaryl, trialkylsilyl, haloalkyl, deuterated alkyl, alkoxy, alkylthio, aryloxy, or arylthio, etc. The number of substituents can be one or more.

[0039] In this invention, "multiple" refers to two or more, such as two, three, four, five, six, etc.

[0040] The hydrogen atoms in the compound structure of this invention include various isotopes of hydrogen, such as hydrogen (H), deuterium (D), or tritium (T).

[0041] In this invention, 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.

[0042] In this invention, the formation of saturated or unsaturated rings, such as saturated or unsaturated 3- to 15-membered rings, includes saturated carbon rings, saturated heterocycles, partially unsaturated carbon rings, partially unsaturated heterocycles, aromatic carbon rings, and aromatic heterocycles. When n-membered is used as a prefix for a ring, n is an integer, indicating that the number of ring atoms in the ring is n. For example, 3- to 15-membered rings refer to rings with 3 to 15 ring atoms, including rings with 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, and 15 ring atoms.

[0043] In this invention, 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 conjugated by carbon-carbon bonds, a monocyclic aryl and a fused-ring aryl group conjugated by carbon-carbon bonds, or two or more fused-ring aryl groups conjugated by carbon-carbon bonds. That is, unless otherwise stated, two or more aromatic groups conjugated by carbon-carbon bonds can also be considered as the aryl group of this invention. Fused-ring aryl groups may include, for example, bicyclic fused aryl (e.g., naphthyl), tricyclic fused aryl (e.g., phenanthrene, fluorene, 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, phenanthryl, biphenyl, terphenyl, triphenylene, perylene, benzo[9,10]phenanthryl, pyrene, benzofluoranthryl, etc. Base, etc.

[0044] In this invention, the aryl group refers to a divalent group formed by the further loss of one or more hydrogen atoms from an aryl group.

[0045] In this invention, terphenyl includes

[0046] In this invention, the substituted aryl group can be one or more hydrogen atoms of the aryl group that are replaced by groups such as deuterium, halogen groups, cyano, aryl, heteroaryl, trialkylsilyl, alkyl, cycloalkyl, haloalkyl, deuteryl, haloaryl, deuteryl, aryloxy, arylthio, alkoxy, alkylthio, etc. It should be understood that the number of carbon atoms in the substituted aryl group refers to the total number of carbon atoms of the aryl group and the substituents on the aryl group. For example, a substituted aryl group with 18 carbon atoms means that the total number of carbon atoms of the aryl group and the substituents is 18.

[0047] In this invention, the number of carbon atoms in the substituted or unsubstituted aryl (or arylene) group can be 6, 8, 10, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 28, 30, 31, 33, 34, 35, 36, 38, or 40, etc.

[0048] In this invention, the fluorene group can be replaced by one or more substituents. When the fluorene group is replaced, the substituted fluorene group can be: etc., but not limited to this.

[0049] In this invention, the aryl group used as a substituent is, for example, but not limited to, phenyl, naphthyl, phenanthryl, biphenyl, fluorenyl, dimethylfluorenyl, anthracene, etc. Benzyl, triphenylene, terphenyl, etc.

[0050] In this invention, a heteroaryl group refers to a monovalent aromatic ring or its derivative containing 1, 2, 3, 4, 5, 6, or 7 heteroatoms. The heteroatoms can be one or more 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 conjugated by carbon-carbon bonds, and any aromatic ring system can be a single aromatic monocyclic ring or a fused aromatic ring. For example, heteroaryl groups may include, but are not limited to, thiopheneyl, furanyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridineyl, pyridazinyl, quinolinyl, quinazolinyl, quinoxazinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, isoquinolinyl, indolyl, carbazoleyl, benzoxazolyl, benzoimidazolyl, benzothiazolyl, benzocarbazoleyl, benzothiaphenyl, dibenzothiaphenyl, thiaphenothiaphenyl, benzofuranyl, phenanthrololinyl, isoxazolyl, thiadiazolyl, phenthiaazinyl, silfluorenyl, dibenzofuranyl, and N-phenylcarbazoleyl, N-pyridylcarbazoleyl, N-methylcarbazoleyl, etc. Among them, thienyl, furanyl, and phenanthroline are heteroaryl groups of the single aromatic ring type, while N-phenylcarbazolyl and N-pyridylcarbazolyl are heteroaryl groups of the polycyclic system type connected by carbon-carbon bonds.

[0051] In this invention, the heteroaryl group refers to a divalent group formed by the further loss of one or more hydrogen atoms from a heteroaryl group.

[0052] In this invention, the substituted heteroaryl (or heteroarylene) group can be one or more hydrogen atoms of the heteroaryl (or heteroarylene) group that are substituted by groups such as deuterium, halogen groups, cyano, aryl, heteroaryl, trialkylsilyl, alkyl, cycloalkyl, haloalkyl, deuteryl, haloaryl, deuteryl, aryloxy, arylthio, alkoxy, alkathio. It should be understood that, in this invention, the number of carbon atoms in the substituted heteroaryl (or heteroarylene) group refers to the total number of carbon atoms of the heteroaryl group and the substituents on it. For example, a substituted heteroaryl group with 18 carbon atoms refers to a heteroaryl group and substituents with a total carbon number of 18.

[0053] In this invention, the number of carbon atoms in the substituted or unsubstituted heteroaryl (or hypoaryl) group can be selected from 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, etc.

[0054] In this invention, the heteroaryl groups used as substituents include, but are not limited to, pyridyl, carbazolyl, quinolinyl, isoquinolinyl, phenantholinyl, benzoxazolyl, benzothiazolyl, benzoimidazolyl, dibenzothiophene, dibenzofuranyl, N-phenylcarbazolyl, etc.

[0055] In this invention, alkyl groups having 1 to 10 carbon atoms can include straight-chain alkyl groups having 1 to 10 carbon atoms and branched alkyl groups having 3 to 10 carbon atoms. The number of carbon atoms in an alkyl group can be, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10. Specific examples of alkyl groups include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, and n-hexyl.

[0056] In this invention, the halogen group can be, for example, fluorine, chlorine, bromine, or iodine.

[0057] In this invention, specific examples of alkyl halides include, but are not limited to, trifluoromethyl.

[0058] In this invention, specific examples of deuterated alkyl groups include, but are not limited to, trideuterated methyl groups.

[0059] In this invention, specific examples of deuterated aryl groups include, but are not limited to, deuterated benzene.

[0060] In this invention, specific examples of halogenated aryl groups include, but are not limited to, fluorobenzenes.

[0061] In this invention, the cycloalkyl group has 3 to 10 carbon atoms, for example, 3, 4, 5, 6, 7, 8, or 10. Specific examples of cycloalkyl groups include, but are not limited to, cyclopentyl, cyclohexyl, and adamantyl.

[0062] In this invention, the number of carbon atoms in the trialkylsilyl group is 3 to 12, for example, 3, 6, 7, 8, 9, etc. Specific examples of trialkylsilyl groups include, but are not limited to, trimethylsilyl, ethyldimethylsilyl, triethylsilyl, etc.

[0063] In this invention, a heteroaryl group having 3 to 20 carbon atoms refers to a heteroaryl group having 3 to 20 carbon atoms and containing at least one nitrogen atom, oxygen atom, or sulfur atom.

[0064] In this invention, the non-positioning connecting key involves a single bond extending from the loop 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.

[0065] 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).

[0066]

[0067] 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.

[0068]

[0069] In this invention, 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).

[0070]

[0071] 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 24 carbon atoms.

[0072] In some embodiments, Ar1 and Ar2 are each 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, and substituted or unsubstituted heteroaryl groups having 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23 or 24 carbon atoms.

[0073] In some embodiments, the substituents of Ar1 and Ar2 are each independently selected from deuterium, cyano, halogen groups, alkyl groups with 1 to 4 carbon atoms, haloalkyl groups with 1 to 4 carbon atoms, deuteryl groups with 1 to 4 carbon atoms, trialkylsilyl groups with 3 to 8 carbon atoms, aryl groups with 6 to 12 carbon atoms, haloaryl groups with 6 to 12 carbon atoms, deuteryl groups with 6 to 12 carbon atoms, heteroaryl groups with 5 to 12 carbon atoms, and cycloalkyl groups with 5 to 6 carbon atoms; optionally, any two adjacent substituents in Ar1 and Ar2 form a saturated or unsaturated 5 to 13-membered ring.

[0074] 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 anthracene, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted carbazolyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted cyclopentanespirofluorenyl, and substituted or unsubstituted cyclohexanespirofluorenyl.

[0075] Optionally, the substituents of 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, cyclopentyl or cyclohexyl.

[0076] In some embodiments, Ar1 and Ar2 may be the same or different, and each is independently selected from substituted or unsubstituted groups Q, wherein the unsubstituted group Q is selected from the group consisting of:

[0077]

[0078] The substituted group Q has one or more substituents, which may be the same or different, and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl, phenyl, naphthyl, cyclopentyl or cyclohexyl.

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

[0080]

[0081]

[0082] In some embodiments, L, L1, and L2 are each independently selected from single bonds, substituted or unsubstituted aryl groups having 6 to 18 carbon atoms, and substituted or unsubstituted heteroaryl groups having 12 to 18 carbon atoms.

[0083] In some embodiments, L, L1, and L2 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted aryl groups having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, or 18 carbon atoms, and substituted or unsubstituted heteroaryl groups having 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, or 18 carbon atoms.

[0084] Optionally, the substituents of L, L1, and L2 may be the same or different, and each may be independently selected from deuterium, cyano, halogen group, alkyl with 1 to 4 carbon atoms, haloalkyl with 1 to 4 carbon atoms, deuterated alkyl with 1 to 4 carbon atoms, aryl with 6 to 12 carbon atoms, haloaryl with 6 to 12 carbon atoms, deuterated aryl with 6 to 12 carbon atoms, and heteroaryl with 5 to 12 carbon atoms.

[0085] In some embodiments, L, L1, and L2 are each independently selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted phenanthylene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuranylene, and substituted or unsubstituted carbazolyl.

[0086] Optionally, the substituents of 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, trifluoromethyl, trideuterated methyl, phenyl, or naphthyl.

[0087] In some embodiments, L, L1, and L2 may be the same or different, and each is independently selected from single-bonded, substituted, or unsubstituted groups V, wherein the unsubstituted group V is selected from the group consisting of:

[0088]

[0089] The substituted group V has one or more substituents, which may be the same or different, and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, phenyl or naphthyl.

[0090] In some embodiments, L is selected from a single bond, a substituted or unsubstituted group V1, wherein the unsubstituted group V1 is selected from the group consisting of:

[0091]

[0092] The substituted group V1 has one or more substituents, which may be the same or different, and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, phenyl or naphthyl.

[0093] In some embodiments, L is selected from the group consisting of single bonds or the following groups:

[0094]

[0095] In some embodiments, L1 and L2 are each independently selected from a single-bonded, substituted, or unsubstituted group V2, wherein the unsubstituted group V2 is selected from the group consisting of:

[0096]

[0097] The substituted group V2 has one or more substituents, which may be the same or different, and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, phenyl or naphthyl.

[0098] In some embodiments, L1 and L2 are each independently selected from the group consisting of single bonds or the following groups:

[0099]

[0100] In some implementations... Each is independently selected from the following groups:

[0101]

[0102] In some embodiments of the present invention, each of R1, R2, R3 and R4 may be the same or different, and each is independently selected from substituted or unsubstituted methyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted phenyl or substituted or unsubstituted naphthyl.

[0103] The substituents in R1, R2, R3, and R4 may be the same or different, and each is independently selected from deuterium or fluorine.

[0104] In some alternative embodiments, each of R1, R2, R3 and R4 may be the same or different, and each may be independently selected from methyl or phenyl.

[0105] In some embodiments of the present invention, each R5 is independently selected from deuterium, cyano, fluorine, methyl, tert-butyl, phenyl, biphenyl or naphthyl.

[0106] In some embodiments, the compound represented by Formula 1 is selected from the structures represented by Formula 2-1, 2-2, or 2-3:

[0107]

[0108] In some embodiments, the compound represented by Formula 1 is selected from the structures represented by Formulas 3-1, 3-2, 3-3, 3-4, 3-5, 3-6, 3-7, 3-8, 3-9, 3-10, 3-11, or 3-12:

[0109]

[0110]

[0111] In some alternative embodiments, the compound represented by Formula 1 is selected from the structures represented by Formulas 3-3, 3-6, 3-9, 3-11 or 3-12.

[0112] Optionally, the compound is selected from the group consisting of compounds listed below.

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122] A second aspect of the present invention provides an organic electroluminescent device, comprising an anode, a cathode, and a functional layer disposed between the anode and the cathode; wherein the functional layer comprises the compound described in the first aspect of the present invention.

[0123] The compounds provided by this invention can be used to form at least one organic film layer in a functional layer to improve the luminous efficiency and lifetime of organic electroluminescent devices.

[0124] Optionally, the functional layer includes an organic light-emitting layer, which comprises the compound. The organic light-emitting layer may be composed of the compound provided by this invention, or it may be composed of the compound provided by this invention and other materials.

[0125] According to one specific embodiment, the organic electroluminescent device, such as Figure 1As shown, an organic electroluminescent device may include an anode 100, a hole injection layer 310, a first hole transport layer 321, a second hole transport layer (hole auxiliary layer) 322, an organic light-emitting layer 330, a hole blocking layer 331, an electron transport layer 340, an electron injection layer 350, and a cathode 200, which are stacked sequentially.

[0126] In this invention, the anode 100 comprises an anode material, 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.

[0127] In this invention, 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:

[0128]

[0129] Those skilled in the art may refer to existing technologies for selection, and the present invention does not impose any special limitations on this.

[0130] In one embodiment, the first hole transport layer 321 may be composed of HT-11.

[0131] In one embodiment, the second hole transport layer 322 is an organic compound of the present invention.

[0132] Optionally, a hole injection layer 310 is further provided between the anode 100 and the first hole transport layer 321 to enhance the ability to inject holes into the first 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; the present invention 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;

[0133]

[0134] In one embodiment, the hole injection layer 310 is composed of HAT-CN.

[0135] In this invention, the organic light-emitting layer 330 can be composed of a single light-emitting material, or it can 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.

[0136] 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.

[0137] In some embodiments of the present invention, the main materials of the organic light-emitting layer 330 are GH-1 and compound GH-2.

[0138] 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; the present invention 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,

[0139]

[0140]

[0141] In some embodiments of the present invention, the host material of the organic light-emitting layer 330 is GH-1 and compound GH-2, and the guest material is GD-1.

[0142] Hole blocking layer 331 is a layer that blocks holes from reaching the cathode, and it can typically be formed under the same conditions as hole injection layer 310. Specifically, it includes oxadiazole or triazole derivatives, phenanthroline derivatives, aluminum complexes, etc., but the present invention does not impose any particular limitation on these.

[0143] In some embodiments of the present invention, the hole blocking layer 331 is composed of HB-1.

[0144] 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 may be selected from, but are not limited to, BTB, LiQ, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials. This invention does not impose any specific limitations on these materials. The material of the electron transport layer 340 includes, but is not limited to, the following compounds:

[0145]

[0146] In one embodiment of the present invention, the electron transport layer 340 may be composed of BTB and LiQ, or ET-1 and LiQ.

[0147] In this invention, the cathode 200 may include a cathode material that has a small work function and facilitates electron injection into the functional layers. 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. Optionally, a metal electrode comprising magnesium and silver may be included as the cathode.

[0148] Optionally, 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. In one embodiment of the present invention, the electron injection layer 350 may include ytterbium (Yb).

[0149] A third aspect of the present invention provides an electronic device including the organic electroluminescent device described in the second aspect of the present invention.

[0150] According to one implementation method, such as Figure 2 As shown, the provided electronic device is electronic device 400, which includes the aforementioned organic electroluminescent device. 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 including but not limited to computer screens, mobile phone screens, televisions, electronic paper, emergency lighting, optical modules, etc.

[0151] The following examples illustrate the synthesis method of the compounds of the present invention, but this disclosure is not limited thereto.

[0152] Synthesis Examples

[0153] Those skilled in the art will recognize that the chemical reactions described in this invention can be suitably used to prepare many of the organic compounds of this invention, and other methods for preparing the compounds of this invention are considered to be within the scope of this invention. For example, the synthesis of those non-illustrative compounds according to this invention can be successfully accomplished by those skilled in the art through modification methods, such as by appropriately protecting interfering groups, by utilizing other known reagents besides those described in this invention, or by making some conventional modifications to the reaction conditions. The compounds synthesized by methods not mentioned in this invention are all commercially available raw material products.

[0154] Preparation of intermediates

[0155] Preparation of IA-1#

[0156]

[0157] Under N2 protection, 76.0 g of 3,3-dimethyl-2-(1-naphthyl)-butanol and 600 mL of dichloromethane (CH2Cl2) were added to a 2 L three-necked flask. Stirring was started, and after the raw materials were dissolved, 100 g of aluminum trichloride-nitromethane solution (AlCl3 / CH3NO2, AlCl3 mass fraction was 47%) was slowly added dropwise. After the addition was completed, the mixture was stirred at room temperature for 6 h. After the reaction was completed, the reaction solution was poured into 800 mL of deionized water, followed by the addition of 600 mL of dichloromethane for extraction. The extracted organic phase was washed with water until neutral, and then 50 g of anhydrous magnesium sulfate was added. The mixture was allowed to stand for 30 min to dry and remove water. After filtration, the filtrate was concentrated to obtain a pale yellow crude oil. The crude product was purified on an alumina column using a mobile phase of dichloromethane / petroleum ether (V:V = 1:6) to obtain a white solid, intermediate IA-1# (55.72 g, yield 79.6%).

[0158] Preparation of IA

[0159]

[0160] Intermediate IA-1# (55 g, 261.51 mmol) and 600 mL of dichloromethane were added to a 1 L single-necked flask. The mixture was stirred at room temperature for 30 min to ensure complete dissolution of the starting material. N-bromosuccinimide (NBS, 46.54 g, 261.51 mmol) was added in portions, and the mixture was stirred overnight. After the reaction was complete, the reaction solution was washed three times with 500 mL of water each time. After washing, the organic phases were combined, and 30 g of anhydrous magnesium sulfate was added. The mixture was allowed to stand for 30 min to remove water and dry. The solvent was removed by vacuum evaporation to obtain a yellow solid, intermediate IA (59.45 g, yield 78.6%).

[0161] Preparation of IN-1

[0162]

[0163] Under N2 protection, 20 g (85.80 mmol) of 4-bromobiphenyl, 18.32 g (87.51 mmol) of 2-amino-9,9-dimethylfluorene, and 160 mL of toluene were added to a 500 mL three-necked flask. The mixture was heated to 110 °C until the reactants were completely dissolved. The temperature was then lowered to approximately 70 °C, and tris(dibenzylacetone)dipalladium (0.79 g, 0.86 mmol), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (0.82 g, 1.72 mmol), and sodium tert-butoxide (12.37 g, 128.69 mmol) were added sequentially. The mixture was refluxed for 2 h and then cooled to room temperature. The product solution was washed three times with water, and then 10 g of anhydrous magnesium sulfate was added. The mixture was allowed to stand for 30 min to dry and remove water. After filtration, the solution was concentrated. The concentrate was purified by column chromatography to obtain intermediate IN-1 (20.03 g, yield 64.59%).

[0164] Using the same synthetic method as intermediate IN-1, the intermediates listed in Table 1 were synthesized by replacing 2-amino-9'9-dimethylfluorene with the starting material Ar-NH2 listed in Table 1, and replacing 4-bromobiphenyl with the starting material Ar-X, while keeping other conditions unchanged. The intermediates listed in Table 1 are: IN-2, IN-3, IN-4, IN-5, IN-6, IN-7, IN-8, IN-9, IN-10, IN-11, IN-12, IN-13, IN-14, and IN-15. The specific starting materials and yields are shown in Table 1.

[0165] Table 1: Intermediates IN-2 to IN-15

[0166]

[0167]

[0168] Preparation of IA-L1

[0169]

[0170] Under nitrogen protection, intermediate IA (20 g, 69.15 mmol), m-chlorophenylboronic acid (12.98 g, 82.98 mmol), tetrabutylammonium bromide (4.46 g, 13.83 mmol), potassium carbonate (21.95 g, 159.05 mmol), toluene (160 mL), ethanol (60 mL), and water (40 mL) were added to a 500 mL three-necked flask. Stirring was started and nitrogen protection was maintained. The mixture was heated to 50°C–60°C, and tetra(triphenylphosphine)palladium (3.99 g, 3.46 mmol) was quickly added. After the addition was complete, the mixture was refluxed to 70°C–75°C for 8 hours. After the reaction was complete, the mixture was cooled to room temperature, and the reaction solution was extracted with toluene to obtain the organic phase. The obtained organic phase was washed with water until neutral, then dried, filtered, and concentrated to obtain a concentrated solution. The resulting concentrate was recrystallized from ethyl acetate to LC>99%, and dried to give a white solid intermediate IA-L1 (16.9 g, yield 76.16%).

[0171] Using the same synthesis method as intermediate IA-L1, the intermediates listed in Table 2 were prepared by replacing m-chlorophenylboronic acid with raw material 1 from Table 2, while keeping other conditions unchanged: IA-L2, IA-L3, IA-L4, IA-L5, IA-L6, and IA-L7. The specific raw materials and yields are shown in Table 2.

[0172] Table 2: Intermediates IA-L2 to IA-L7

[0173]

[0174]

[0175] Intermediate IB-1#

[0176]

[0177] Under N2 protection, sodium hydride (14.27 g, 594.53 mmol) and 150 mL tetrahydrofuran were added to a 500 mL three-necked flask. The temperature was maintained at -5 °C to 5 °C, and the mixture was stirred for 30 min. Then, a tetrahydrofuran solution of acenaphthene (20 g, 118.91 mmol) was added dropwise. After the addition was complete, the temperature was maintained at -5 °C to 5 °C, and the mixture was stirred for 1 h. Subsequently, iodomethane (50.47 g, 355.57 mmol) was added dropwise. After the addition was complete, the mixture was kept at -5 °C to 5 °C for 1 h. After the reaction was completed, the reaction solution was poured into a saturated ammonium chloride solution on ice, and then extracted with 500 mL dichloromethane. The organic phase was washed with water until neutral, dried with 200 g of anhydrous magnesium sulfate, allowed to stand for 30 min, filtered, and concentrated to obtain intermediate IB-1# (21.71 g, yield 93.05%).

[0178] Intermediate IB-2#

[0179]

[0180] Under N2 protection, intermediate IB-1# (20 g, 101.91 mmol) and tetrahydrofuran (200 mL) were added to a 500 mL three-necked flask. After stirring at room temperature for 30 min, phenyl magnesium bromide (18.48 g, 101.91 mmol) was added dropwise. After the addition was complete, the reaction was allowed to proceed at room temperature for 3 h. After the reaction was completed, 2 mol / L dilute hydrochloric acid was added to the reaction solution until the reaction system became weakly acidic. Then, 500 mL of dichloromethane was added for extraction. The resulting organic phases were combined and washed with water until neutral. After drying with anhydrous magnesium sulfate, the drying agent was removed by filtration. The solvent was removed by vacuum distillation of the filtrate to obtain a white solid, which was intermediate IB-2# (23.71 g, yield 84.80%).

[0181] Intermediate IB-3#

[0182]

[0183] Under N2 protection, intermediate IB-2# (23 g, 83.83 mmol) and benzene (200 mL) were added to a 500 mL three-necked flask. After stirring at room temperature for 30 min, trifluoromethanesulfonic acid (37.74 g, 251.49 mmol) was added directly. The reaction system was then rapidly heated, and the reaction was refluxed and timed. After 3 h, the reaction solution was cooled to room temperature and washed with water until neutral. 20 g of anhydrous magnesium sulfate was added, and the mixture was allowed to stand for 30 min to dry. The organic phase was filtered and concentrated to obtain a white solid, which was intermediate IB-3# (26.21 g, yield 93.51%).

[0184] Intermediates I-B1 and I-B2

[0185]

[0186] At room temperature, intermediate IB-3# (25 g, 74.76 mmol) and dichloromethane (250 mL) were added to a 500 mL single-necked flask. The mixture was stirred at room temperature for 30 min to ensure complete dissolution of the starting material. N-bromosuccinimide (NBS) (12.92 g, 72.57 mmol) was added in portions. After complete addition of NBS, the mixture was stirred for 3 h. After the reaction was complete, the reaction solution was washed three times with 300 mL of water each time. The washed organic phases were combined and 15 g of anhydrous magnesium sulfate was added. The mixture was allowed to stand for 30 min to remove water and dry. The solvent was then removed by vacuum distillation to obtain a yellow oily substance. The yellow oily substance was separated by column chromatography (using cyclohexane as eluent) to obtain intermediate I-B1 (11.03 g, 35.69%) and intermediate I-B2 (9.03 g, 29.22%), respectively.

[0187] Intermediate I-B1-L1

[0188]

[0189] Under nitrogen protection, intermediate I-B1 (10 g, 24.19 mmol), o-chlorophenylboronic acid (4.54 g, 29.03 mmol), tetrabutylammonium bromide (1.56 g, 4.84 mmol), potassium carbonate (7.68 g, 55.64 mmol), toluene (80 mL), ethanol (30 mL), and water (20 mL) were added to a 250 mL three-necked flask. Stirring was started and nitrogen protection was maintained. The mixture was heated to 50–60 °C, and tetra(triphenylphosphine)palladium (1.4 g, 1.21 mmol) was quickly added. After the addition was complete, the mixture was refluxed to 70–75 °C for 6 h. After the reaction was complete, the mixture was cooled to room temperature, extracted with toluene to obtain the organic phase, washed with water until neutral, dried, filtered, and concentrated to obtain a yellow solid powder. The yellow solid powder was then washed with ethanol at room temperature to achieve an LC > 99%. After drying, a yellow solid was obtained: intermediate I-B1-L1 (7.91 g, yield 73.48%).

[0190] Intermediates I-B1-L2, I-B2-L1, and I-B2-L2 were prepared using the same synthetic method as intermediate I-B1-L1, with the following differences: intermediate Ix was used to replace intermediate I-B1, and raw material 2 was used to replace m-chlorophenylboronic acid, while other conditions remained unchanged. The specific raw materials and yields are shown in Table 3 below.

[0191] Table 3

[0192]

[0193] Intermediate IC-1#

[0194]

[0195] Under N2 protection, p-chlorobromobenzene (16 g, 83.57 mmol) and tetrahydrofuran (120 mL) were added to a 500 mL three-necked flask. After cooling to -80 °C to -90 °C, n-butyllithium (6.42 g, 100.28 mmol) was added dropwise while maintaining the temperature at -80 °C to -90 °C. After the addition was completed, the temperature was maintained for 1 h. Then, a tetrahydrofuran solution (150 mL) containing intermediate IB-1# (19.68 g, 100.28 mmol) was added dropwise. After the addition was completed, the temperature was maintained between -80 °C and -90 °C for 2 h, and then the temperature was naturally raised to room temperature. After the temperature stabilizes, dilute hydrochloric acid is added to the reaction solution until the reaction solution is weakly acidic (pH between 5.0 and 6.0). Then, 300 mL of dichloromethane is added for organic phase extraction. The organic phases are combined and washed with water until neutral. Then, 20 g of anhydrous magnesium sulfate is added and allowed to stand for 30 min to dry and remove water. After filtration and concentration, a white solid is obtained, which is intermediate IC-1# (12.45 g, yield 40.2%).

[0196] Intermediate IC

[0197]

[0198] Under N2 protection, intermediate IC-1# (12 g, 38.86 mmol) and benzene (120 mL) were added to a 250 mL three-necked flask. After stirring at room temperature for 30 min, trifluoromethanesulfonic acid (17.49 g, 116.57 mmol) was added directly. The reaction system was then rapidly heated and refluxed for timing. After 3 h, the reaction solution was cooled to room temperature and washed with water until neutral. 10 g of anhydrous magnesium sulfate was added and allowed to stand for 30 min to dry. After filtration and concentration, a white solid was obtained, which was intermediate IC (10.16 g, yield 70.90%).

[0199] Intermediate ICL-1#

[0200]

[0201] Intermediate IC (20.00 g, 54.22 mmol), pinacol diboronate (16.52 g, 65.06 mmol), tris(dibenzylacetone)palladium (0.99 g, 1.08 mmol), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (1.03 g, 2.17 mmol), and potassium acetate (7.98 g, 81.32 mmol) were added to isopropyl acetate (200 mL). The mixture was heated to 85 °C–90 °C under nitrogen protection and stirred for 24 h. After cooling to room temperature, the product precipitated. The product was filtered and washed until neutral. The obtained product was dissolved in toluene and purified by silica gel column chromatography. Then, it was purified by recrystallization from toluene to obtain intermediate ICL-1# (16.45 g, yield 65.91%).

[0202] intermediate ICL

[0203]

[0204] To a 250 mL three-necked flask, add intermediate IC-L1-1# (15.0 g, 43.44 mmol), p-chlorobromobenzene (9.98 g, 52.12 mmol), tetrabutylammonium bromide (0.56 g, 1.74 mmol), potassium carbonate (8.99 g, 65.16 mmol), toluene (120 mL), ethanol (45 mL), and water (30 mL). Stirring is initiated and nitrogen is introduced for protection. The mixture is heated to 50–60 °C, and tetra(triphenylphosphine)palladium (1.00 g, 0.87 mmol) is rapidly added. After the addition is complete, the mixture is refluxed at 70–75 °C for 12 h. Once the reaction is complete, the mixture is cooled to room temperature, extracted with dichloromethane, and the organic phase is washed with water until neutral. The mixture is dried, filtered, and concentrated. Recrystallization is performed using a mixture of toluene and n-heptane. Drying yields a white solid intermediate ICL (14.22 g, 73.56% yield).

[0205]

[0206] Intermediate ID-1#

[0207] Intermediate ID-1# was prepared using the same synthetic method as intermediate IC-1#, except that p-chlorobromobenzene was replaced with m-chlorobromobenzene.

[0208] Intermediate ID

[0209] Intermediate ID (ID (8.93 g, yield 72.11%)) was prepared using the same synthesis method as intermediate IC, except that ID-1# was used instead of IC-1#.

[0210] Intermediate IDL-1#.

[0211] Intermediate IDL-1# was prepared using the same synthesis method as intermediate ICL-1#, except that ID was used instead of IC.

[0212] Intermediate IDL

[0213] Intermediate IDL was prepared using the same synthesis method as intermediate ICL, except that IDL-1# was used instead of ICL-1#.

[0214] Preparation of compound 2

[0215]

[0216] Under N2 protection, intermediate IA (15 g, 51.86 mmol), intermediate IN-1 (18.82 g, 52.07 mmol), and toluene (150 mL) were added to a 500 mL three-necked flask. The mixture was heated until the starting materials were completely dissolved, then cooled to 70 °C. Tris(dibenzylacetone)dipalladium (0.48 g, 0.52 mmol), 2-dicyclohexylphosphine-2′,6′-dimethoxybiphenyl (0.43 g, 1.04 mmol), and sodium tert-butoxide (7.51 g, 78.11 mmol) were added sequentially. The mixture was refluxed for 2 h, and after the reaction was complete, it was cooled to room temperature. The reaction solution was washed three times with water, and 10 g of anhydrous magnesium sulfate was added. The solution was allowed to stand for 30 min to remove water. The dehydrated solution was subjected to column chromatography to remove the catalyst, and then concentrated to obtain the crude product. The crude product was recrystallized from toluene / n-heptane to give a white solid powder, compound 2 (13.99 g, yield 47.34%), as shown by mass spectrometry (m / z = 570.3 [M+H]). + ).

[0217] Preparation of compound 11

[0218]

[0219] Compound 11 was synthesized using the same method as compound 2, except that intermediate IA-L1 was used instead of intermediate IA, while other starting materials remained unchanged. Compound 11 (7 g, yield 44.68%) was synthesized using mass spectrometry (m / z = 646.34 [M+H)). + ).

[0220] Synthesis of compounds: Compound 14, Compound 15, Compound 31, Compound 33, Compound 34, Compound 46, Compound 47, Compound 56, Compound 57, Compound 70, Compound 76, Compound 78, Compound 88, and Compound 232

[0221] The compounds in Table 4 were prepared using the same synthetic method as that used for compound 11, except that intermediate IAX was used instead of intermediate IA-L1 and intermediate INn was used instead of intermediate IN-1. The selected raw materials and the structures of the compounds are shown in Table 4.

[0222] Table 4 Synthesis of compounds of the present invention

[0223]

[0224]

[0225]

[0226]

[0227] Preparation of compound 103

[0228]

[0229] Compound 103 was synthesized using the same method as compound 2, except that intermediate IA was replaced with intermediate I-B1-L1, while other starting materials remained unchanged. This resulted in the synthesis of compound 103 (7.3 g, yield 56.24%), (m / z = 770.4 [M+H]). + ).

[0230] Synthesis of compounds: Compound 116, Compound 118, Compound 136, and Compound 139

[0231] The compounds listed in the table below were prepared using the same synthetic method as that used for compound 103, except that intermediate I-B1-L1 was replaced by reactant 3 from Table 5, and intermediate IN-1 was replaced by reactant 4. Specific reactants and yields are shown in Table 5 below.

[0232] Table 5 Synthesis of compounds of the present invention

[0233]

[0234] Preparation of compound 151

[0235]

[0236] Compound 151 was synthesized using the same method as compound 2, except that intermediate IC was used instead of intermediate IA, and intermediate IN-2 benzene was used instead of intermediate IN-1. Compound 151 was obtained (10.71 g, yield 60.41%), mass spectrometry (m / z = 654.31 [M+H]). + ).

[0237] Synthesis of compounds: Compound 154, Compound 171, Compound 173, Compound 191, Compound 194, and Compound 211

[0238] The compounds listed in the table below were prepared using the same synthetic method as that used for compound 151, except that intermediate INn replaced intermediate IN-2, and intermediate IN replaced intermediate IC. Specific starting materials and yields are shown in Table 6 below.

[0239] Table 6 Compounds of the present invention

[0240]

[0241]

[0242] The NMR data of the compounds are shown in Table 7:

[0243] Table 7

[0244]

[0245] Fabrication and Evaluation Examples of Organic Electroluminescent Devices

[0246] Example 1: Organic electroluminescent device

[0247] The anode is prepared through the following process: ITO with a thickness of [missing information] is applied. The glass substrate is cut to a size of 40mm (length) × 40mm (width) × 0.7mm (thickness). A photolithography process is used to fabricate an experimental substrate with cathode, anode, and insulating layer patterns. Surface treatment with ultraviolet ozone and O2:N2 ions can be performed to increase the work function of the anode. Organic solvents can be used to clean the surface of the ITO substrate to remove impurities and oil. It should be noted that the ITO substrate can also be cut to other sizes according to actual needs; no specific limitation is made to the size of the ITO substrate in this disclosure.

[0248] The compound HAT-CN was vacuum-deposited onto the aforementioned experimental substrate (anode) to form a thickness of [thickness value missing]. A hole injection layer (HIL) is formed, and then compound HT-11 is vacuum-deposited onto the hole injection layer to form a thickness of [thickness missing]. The first hole transport layer (HTL-1).

[0249] Compound 2 is vacuum-deposited onto the first hole transport layer to form a thickness of [missing information]. The second hole transport layer (HTL-2).

[0250] On the second hole transport layer, compound GH-1 and compound GH-2 were uniformly mixed at a weight ratio of 45%:55% to obtain a mixed host material. This mixed host material was then vacuum-deposited with compound GD-1 at a thickness ratio of 100:5 to form a film with a thickness of [thickness value missing]. Organic light-emitting layer (EML).

[0251] Compound HB-1 was vacuum-deposited onto the luminescent layer to form a thickness of [thickness missing]. A hole blocking layer (EBL) was then formed. Next, compound ET-1 and LiQ were mixed in a 1:1 weight ratio and deposited onto the hole blocking layer to form a layer with a thickness of [thickness missing]. The electron transport layer (ETL) is formed by vacuum evaporation of Yb onto the electron transport layer to create a thickness of [thickness value missing]. An electron-injected layer (EIL) is formed, and then magnesium (Mg) and silver (Ag) are co-deposited onto the electron-injected layer at a 1:9 evaporation rate, forming a layer with a thickness of [missing information]. The cathode.

[0252] Furthermore, the vacuum evaporation thickness on the aforementioned cathode is [missing information]. The compound CP-1 was used as a cathode protection layer (CPL) to complete the fabrication of a green electromechanical device.

[0253] Examples 2-39:

[0254] Except that, when forming the second hole transport layer, the organic electroluminescent device was fabricated using the same method as in Example 1, except that the compound 2 used in Example 1 was replaced with the compound in Table 8.

[0255] Comparative Examples 1-4:

[0256] Except that, when forming the second hole transport layer, compounds A, B, C, and D were used to replace compound 2 used in Example 1, the organic electroluminescent device was fabricated using the same method as in Example 1.

[0257]

[0258] The organic electroluminescent devices prepared in Examples 1-39 and Comparative Examples 1-4 were subjected to performance tests, specifically at 10 mA / cm². 2 The IVL performance of the device was tested under the specified conditions. The lifetime of the T95 device was 20 mA / cm. 2 The test was conducted under the specified conditions, and the test results are shown in Table 8.

[0259] Table 8 Performance test results of organic electroluminescent devices

[0260]

[0261]

[0262] Referring to the table above, it can be seen that the green organic electroluminescent devices prepared by using the compounds described in this invention as the second hole transport layer material in Examples 1 to 39 have the characteristics of low voltage, high efficiency and long lifetime.

[0263] Specifically, compared to Comparative Examples 1-4, Examples 1-39 show an efficiency improvement of at least 15.7% and a lifetime improvement of at least 18.6%. The driving voltage of the organic electroluminescent devices of Examples 1-39, using the compounds of the present invention, is superior to that of Comparative Examples 1-4. Therefore, using the organic compounds of the present invention as the second hole transport layer of an organic electroluminescent device can significantly improve device performance.

[0264] Other embodiments of the invention will readily occur to those skilled in the art upon consideration of the specification and practice of the invention disclosed herein. This invention is intended to cover any variations, uses, or adaptations of the invention that follow the general principles of the invention and include common knowledge or customary techniques in the art not disclosed herein.

Claims

1. An organic compound, characterized in that, It has the structure shown in Equation 1: Among them, R1, R2, R3 and R4 may be the same or different, and each is independently selected from substituted or unsubstituted methyl or substituted or unsubstituted phenyl. The substituents in R1, R2, R3, and R4 may be the same or different, and each is independently selected from deuterium or fluorine; L, L1, and L2 are each independently selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, and substituted or unsubstituted phenanthrene. The substituents of L, L1 and L2 may be the same or different, and each is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, phenyl; Ar1 and Ar2 may be the same or different, and are each 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 anthraquinone, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted spirodifluorenyl; Ar1 and Ar2 may have the same or different substituents, and each is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl, phenyl, and naphthyl. Each R5 is independently selected from deuterium, cyano, halogen group, alkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, aryl with 6 to 20 carbon atoms, haloaryl 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, and haloheteroaryl with 3 to 20 carbon atoms; n5 is the number of R5, and n5 is selected from 0.

2. The compound according to claim 1, wherein, Each is independently selected from the following groups:

3. The compound according to claim 1, wherein, The compound shown in Formula 1 is selected from the structure shown in Formula 2-1, 2-2 or 2-3:

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

5. 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 4.

6. The organic electroluminescent device according to claim 5, characterized in that, The functional layer includes a second hole transport layer, which contains the organic compound.

7. The organic electroluminescent device according to claim 5, characterized in that, The organic electroluminescent device is a green organic electroluminescent device.

8. An electronic device, characterized in that, Includes the organic electroluminescent device according to any one of claims 5 to 7.

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