Organic compound, organic electroluminescent device, and electronic apparatus

Abstract

The present application relates to the field of organic electroluminescent material technology, and in particular, to an organic compound, an organic electroluminescent device comprising same, and an electronic apparatus. The compound of the present application comprises a polycyclic conjugated core structure. When used as the host material of a light-emitting layer, the compound of the present application can improve the carrier balance in the light-emitting layer, widen the carrier recombination region, improve the exciton generation and utilization efficiency, and increase the light-emitting efficiency and service life of the device.

Description

Organic compounds and organic electroluminescent devices and electronic devices

[0001] Cross-references to related applications

[0002] This application claims priority to Chinese patent application No. CN202411708533.5, filed on November 26, 2024, the entire contents of which are incorporated herein by reference. Technical Field

[0003] This application relates to the field of organic electroluminescent materials technology, and more particularly to organic compounds and organic electroluminescent devices and electronic devices containing the same. Background Technology

[0004] 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 electroluminescent devices (e.g., OLEDs) typically include a cathode and an anode arranged 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 organic electroluminescent layer to form excitons. The excitons are in an excited state and release energy outward, thereby causing the electroluminescent layer to emit light.

[0005] The main problems with existing organic light-emitting diodes (OLEDs) lie in their lifespan and efficiency. As displays become larger, the driving voltage also increases, necessitating improvements in both luminous efficiency and current efficiency. Therefore, it is essential to continue developing new materials to further enhance the performance of OLEDs. Summary of the Invention

[0006] In view of the above-mentioned problems existing in the prior art, the purpose of this application 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.

[0007] According to a first aspect of this application, an organic compound is provided, the organic compound having the structure shown in Formula 1:

[0008] Where X1 and X2 are the same or different, and are each independently selected from O, S or C(R) a R b );

[0009] Each R a and R bThey may be the same or different, and each is independently selected from alkyl groups having 1 to 10 carbon atoms, haloalkyl groups having 1 to 10 carbon atoms, and deuteralkyl groups having 1 to 10 carbon atoms;

[0010] Each of R1, R2, and R3 may be the same or different, and each is independently selected from hydrogen, 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 18 carbon atoms, deuterated aryl groups with 6 to 18 carbon atoms, heteroaryl groups with 3 to 12 carbon atoms, or... The listening structure is such that only one of R1, R2, and R3 is selected from... The structure shown;

[0011] n1 represents the number of R1s, n2 represents the number of R2s, and n3 represents the number of R3s. n1 is selected from 1, 2, 3, 4, 5, or 6, n2 is selected from 1, 2, 3, or 4, and n3 is selected from 1, 2, 3, or 4.

[0012] A is selected from either Equation 2-1 or Equation 2-2:

[0013] L, L1, L2, L3 and L4 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms.

[0014] The substituents in L, L1, L2, L3, and L4 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, deuteratedalkyl with 1 to 10 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, aryl with 6 to 18 carbon atoms, deuteratedaryl with 6 to 18 carbon atoms, heteroaryl with 3 to 12 carbon atoms, and cycloalkyl with 5 to 10 carbon atoms;

[0015] Ar1, Ar2, Ar3 and Ar4 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms.

[0016] The substituents in Ar1, Ar2, Ar3, and Ar4 may be the same or different, and each is independently selected from deuterium, cyano, halogen group, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuteratedalkyl with 1 to 10 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, aryl with 6 to 18 carbon atoms, deuterated aryl with 6 to 18 carbon atoms, heteroaryl with 3 to 12 carbon atoms, or cycloalkyl with 5 to 10 carbon atoms; optionally, any two adjacent substituents form a saturated or unsaturated 5 to 13-membered ring.

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

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

[0019] The compounds in this application contain two (dibenzofuran)benzene core structures, which are respectively linked to a triazine fragment and a diarylamine fragment. The resulting compounds serve as electron-transporting and hole-transporting host materials for red light emission. On one hand, the di(dibenzofuran)benzene core possesses a suitable first excited triplet state energy level, making it suitable as a fragment for red light host materials. On the other hand, the di(dibenzofuran)benzene core has a large conjugated area, which helps to enhance intermolecular packing of the target compounds and increase the number of charge carriers. When the compounds of this application are used as electron-transporting and hole-transporting host materials in a hybrid red light host material, the carrier balance in the emitting layer can be improved, the carrier recombination region can be broadened, the exciton generation and utilization efficiency can be increased, and the stability of the emitting layer film morphology can be improved, thereby increasing the luminous efficiency and lifetime of the device. Attached Figure Description

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

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

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

[0023] Reference numerals 100, 200, 300, 310, 321, 322, 330, 340, 350, 400, and 350 are also listed. The electronic device is also described. Detailed Implementation

[0024] Exemplary embodiments will now be described more fully with reference to the accompanying drawings. However, exemplary embodiments can be implemented in many forms and should not be construed as limited to the examples set forth herein; rather, these embodiments are provided so that this application will be more comprehensive and complete, and will fully convey the concept of exemplary embodiments to those skilled in the art. The described features, structures, or characteristics may be combined in any suitable manner in one or more embodiments. In the following description, numerous specific details are provided to give a full understanding of embodiments of this application.

[0025] In a first aspect, this application provides an organic compound having the structure shown in Formula 1:

[0026] Where X1 and X2 are the same or different, and are each independently selected from O, S or C(R) a R b );

[0027] Each R a and R b They may be the same or different, and each is independently selected from alkyl groups having 1 to 10 carbon atoms, haloalkyl groups having 1 to 10 carbon atoms, and deuteralkyl groups having 1 to 10 carbon atoms;

[0028] Each of R1, R2, and R3 may be the same or different, and each is independently selected from hydrogen, 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 18 carbon atoms, deuterated aryl groups with 6 to 18 carbon atoms, heteroaryl groups with 3 to 12 carbon atoms, or... The listening structure is such that only one of R1, R2, and R3 is selected from... The structure shown;

[0029] n1 represents the number of R1s, n2 represents the number of R2s, and n3 represents the number of R3s. n1 is selected from 1, 2, 3, 4, 5, or 6, n2 is selected from 1, 2, 3, or 4, and n3 is selected from 1, 2, 3, or 4.

[0030] A is selected from either Equation 2-1 or Equation 2-2:

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

[0032] The substituents in L, L1, L2, L3, and L4 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, deuteratedalkyl with 1 to 10 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, aryl with 6 to 18 carbon atoms, deuteratedaryl with 6 to 18 carbon atoms, heteroaryl with 3 to 12 carbon atoms, and cycloalkyl with 5 to 10 carbon atoms;

[0033] Ar1, Ar2, Ar3 and Ar4 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms.

[0034] The substituents in Ar1, Ar2, Ar3, and Ar4 may be the same or different, and each is independently selected from deuterium, cyano, halogen group, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuteratedalkyl with 1 to 10 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, aryl with 6 to 18 carbon atoms, deuterated aryl with 6 to 18 carbon atoms, heteroaryl with 3 to 12 carbon atoms, or cycloalkyl with 5 to 10 carbon atoms; optionally, any two adjacent substituents form a saturated or unsaturated 5 to 13-membered ring.

[0035] In this application, the terms "optionally" or "optionally" mean that the events or circumstances described below may or may 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, "optionally, any two adjacent substituents form a ring" means that any two adjacent substituents are connected to each other to form a ring, or that any two adjacent substituents may exist independently. "Any two adjacent" can include having two substituents on the same atom, and can also include having one substituent on each of two adjacent atoms; wherein, when there are two substituents on the same atom, the two substituents can form a saturated or unsaturated spirocyclic ring with the atom they are connected to; when there is one substituent on each of two adjacent atoms, the two substituents can fuse into a ring.

[0036] In this application, 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.

[0037] 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, heteroaryl, aryl, trialkylsilyl, alkyl, haloalkyl, cycloalkyl, etc. The number of substituents can be one or more.

[0038] In this application, "multiple" means two or more, such as two, three, four, five, six, etc.

[0039] In this application, a saturated or unsaturated 5- to 13-membered ring refers to a ring containing 5 to 13 ring atoms; for example, but not limited to, cyclopentane, cyclohexane, benzene ring, fluorene ring, etc.

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

[0041] In this application, the number of carbon atoms in substituted or unsubstituted functional groups refers to the total number of carbon atoms. For example, if L1 is a substituted arylene with 12 carbon atoms, then the total number of carbon atoms in the arylene and its substituents is 12.

[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, and triphenylene. Peryl, benzo[9,10]phenanthryl, pyrene Benzofluoranthyl, base Benz[c]phenanthrene wait.

[0043] In this application, the term arylene refers to a divalent or polyvalent group formed by the further loss of one or more hydrogen atoms from an aryl group.

[0044] In this application, terphenyl includes

[0045] In this application, the number of carbon atoms in the substituted aryl group refers to the total number of carbon atoms in the aryl group and the substituents on the aryl group. For example, a substituted aryl group with 18 carbon atoms refers to a total number of 18 carbon atoms in the aryl group and the substituents.

[0046] In this application, the substituted or unsubstituted aryl (arylene) group can have 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, or 30 carbon atoms. In some embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group with 6 to 30 carbon atoms; in other embodiments, it is a substituted or unsubstituted aryl group with 6 to 25 carbon atoms; and in still other embodiments, it is a substituted or unsubstituted aryl group with 6 to 15 carbon atoms.

[0047] 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.

[0048] In this application, the aryl groups that serve as substituents for L, L1, L2, L3, L4, Ar1, Ar2, Ar3, and Ar4 are, for example, but not limited to, phenyl, naphthyl, phenanthryl, biphenyl, fluorenyl, dimethylfluorenyl, etc.

[0049] 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 one or more of B, O, N, P, Si, Se, and S. A heteroaryl group can be a monocyclic heteroaryl group or a 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 an aromatic monocyclic ring or an aromatic fused ring. For example, heteroaryl groups may include thiophene, furanyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinel, pyridazinyl, quinolinyl, quinazolinyl, quinoxazinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, isoquinolinyl, indolyl, carbazole, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazole, benzothiaphenyl, dibenzothiaphenyl, thiaphenothiaphenyl, benzofuranyl, phenanthrololinyl, isoxazolyl, thiadiazolyl, phenthiaazinyl, silfluorenyl, dibenzofuranyl, and N-phenylcarbazole, N-pyridylcarbazole, N-methylcarbazole, naphthobenzofuranyl (e.g.) ), phenanthrenebenzofuranyl (e.g.) (and others, but not limited to these.)

[0050] In this application, the term "hybrid aryl" refers to a divalent or polyvalent group formed by the further loss of one or more hydrogen atoms from a heteroaryl group.

[0051] In this application, the number of carbon atoms in the substituted or unsubstituted heteroaryl group (hybrid aryl 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, or 30. In some embodiments, the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group with a total carbon number of 3 to 30; in other embodiments, the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group with a total carbon number of 3 to 18; and in still other embodiments, the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group with a total carbon number of 5 to 12.

[0052] In this application, the heteroaryl groups that serve as substituents for L, L1, L2, L3, L4, Ar1, Ar2, Ar3, and Ar4 are, for example but not limited to, pyridyl, carbazolyl, quinolinyl, isoquinolinyl, phenanthrolinel, benzoxazolyl, benzothiazolyl, benzoimidazolyl, dibenzothiophene, and dibenzofuranyl.

[0053] In this application, the substituted heteroaryl group may be one or more hydrogen atoms of the heteroaryl group that are replaced by groups such as deuterium, halogen groups, cyano, aryl, heteroaryl, trialkylsilyl, alkyl, cycloalkyl, haloalkyl, etc. It should be understood that the number of carbon atoms in the substituted heteroaryl group refers to the total number of carbon atoms of the heteroaryl group and the substituents on the heteroaryl group.

[0054] In this application, 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.

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

[0056] In this application, specific examples of trialkylsilyl groups include, but are not limited to, trimethylsilyl, triethylsilyl, etc.

[0057] In this application, the number of carbon atoms in the alkyl halogroup is, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10. Specific examples of alkyl halogroups in this application include, but are not limited to, trifluoromethyl.

[0058] In this application, the number of carbon atoms in the deuterated alkyl group having 1 to 10 carbon atoms is, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10. Specific examples of deuterated alkyl groups in this application include, but are not limited to, trideuterated methyl.

[0059] In this application, the number of carbon atoms in cycloalkyl groups with 3 to 10 carbon atoms can be, for example, 3, 4, 5, 6, 7, 8, 9, or 10. Specific examples of cycloalkyl groups include, but are not limited to, cyclopentyl, cyclohexyl, and adamantyl.

[0060] In this application, the non-positioned connecting key refers to the single bond extending from the loop system. This indicates that one end of the linker can connect to any position in the ring system it traverses, and the other end connects to the rest of the compound molecule. 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 linkers that traverse the bicyclic ring. This means that any possible connection mode shown in equations (f-1) to (f-10) is included.

[0061] For example, as shown in equation (X′), the dibenzofuran group represented by equation (X′) is connected to other positions in the molecule via a non-positional linker extending from the middle of one side of the benzene ring. This means that any possible connection mode shown in equations (X′-1) to (X′-4) is included.

[0062] In this application, a non-orienting 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-orienting linking bond, which means that it includes any possible connection mode shown in equations (Y-1) to (Y-7):

[0063] In some embodiments, the organic compounds of this application are selected from any of the structures shown in formulas (1-1) to (1-12):

[0064] In equations (1-1) to (1-12), X1 and X2 may be the same or different, and each is independently selected from O or S; n4 is selected from 0, 1, 2 or 3; n5 is selected from 0, 1, 2, 3, 4 or 5;

[0065] Each of R1, R2, and R3 may be the same or different, and each is independently selected from hydrogen, deuterium, cyano, fluorine, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl, or phenyl.

[0066] In some embodiments, Ar1, Ar2, Ar3, and Ar4 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, and substituted or unsubstituted heteroaryl groups having 3, 4, 5, 6, 7, 8, 9, 10, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, or 24 carbon atoms.

[0067] In some embodiments, Ar1, Ar2, Ar3 and Ar4 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups having 6 to 25 carbon atoms, or substituted or unsubstituted heteroaryl groups having 3 to 24 carbon atoms.

[0068] In some embodiments, the substituents in Ar1, Ar2, Ar3, and Ar4 may be the same or different, and each is independently selected from deuterium, halogen groups, cyano, haloalkyl with 1 to 4 carbon atoms, deuteralkyl with 1 to 4 carbon atoms, alkyl with 1 to 4 carbon atoms, cycloalkyl with 5 to 10 carbon atoms, aryl with 6 to 15 carbon atoms, heteroaryl with 5 to 12 carbon atoms, trialkylsilyl with 3 to 8 carbon atoms, or deuteralkyl with 6 to 15 carbon atoms; optionally, any two adjacent substituents form a benzene ring or a fluorene ring.

[0069] In some embodiments, Ar1, Ar2, Ar3, and Ar4 may be the same or different, and each is independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraceneyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrene, substituted or unsubstituted perylene, substituted or unsubstituted... Benz[c]phenanthryl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted carbazolyl, substituted or unsubstituted naphthobenzofuran, substituted or unsubstituted phenanthrenebenzofuran, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted naphthooxazolyl, substituted or unsubstituted naphthothiazolyl.

[0070] In some embodiments, the substituents in Ar1, Ar2, Ar3, and Ar4 may be the same or different, and each is independently selected from deuterium, fluorine, cyano, trideuterated methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, pyridyl, dibenzofuranyl, dibenzothiopheneyl, or carbazoyl; optionally, any two adjacent substituents form a benzene ring or a fluorene ring.

[0071] In some embodiments, Ar1, Ar2, Ar3, and Ar4 may be the same or different, and each is independently selected from the group consisting of:

[0072] In some embodiments, Ar1, Ar2, Ar3, and Ar4 may be the same or different, and each is independently selected from the group consisting of:

[0073] In some embodiments, L, L1, L2, L3 and L4 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 15 carbon atoms, and substituted or unsubstituted heteroaryl groups with 12 to 18 carbon atoms.

[0074] In some embodiments, L, L1, L2, L3, and L4 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, or 15 carbon atoms, and substituted or unsubstituted heteroaryl groups having 12, 13, 14, 15, 16, 17, or 18 carbon atoms.

[0075] In some embodiments, the substituents in L, L1, L2, L3, and L4 may be the same or different, and each is independently selected from deuterium, fluorine, cyano, alkyl with 1 to 5 carbon atoms, trialkylsilyl with 3 to 8 carbon atoms, fluoroalkyl with 1 to 4 carbon atoms, deuterylalkyl with 1 to 4 carbon atoms, phenyl, or naphthyl.

[0076] In some implementations, each R a and R b They may be the same or different, and each is independently selected from methyl, ethyl or trideuterated methyl.

[0077] In some embodiments, L, L1, L2, L3, and L4 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 dibenzothiophene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted fluorene, substituted or unsubstituted phenanthroline, and substituted or unsubstituted carbazolyl.

[0078] In some embodiments, the substituents in L, L1, L2, L3, and L4 may be the same or different, and each is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl, or phenyl.

[0079] In some embodiments, L is selected from single bonds or the following groups:

[0080] In some embodiments, L is selected from the group consisting of single bonds or the following groups:

[0081] In the compounds of this application, when L is selected from a single bond, the distance between the electron transport group and the parent nucleus in the compound is closer, which is beneficial to the effective arrangement of compound molecules in the functional layer and further improves the T95 lifetime of the device.

[0082] In some embodiments, L1, L2, L3, and L4 may be the same or different, and each is independently selected from the group consisting of single bonds or the following groups:

[0083] In some embodiments, L1, L2, L3, and L4 may be the same or different, and each is independently selected from the group consisting of single bonds or the following groups:

[0084] In some implementations... They may be the same or different, and each is independently selected from the following groups:

[0085] In some embodiments, formula 2-1 is selected from the following groups:

[0086] In some embodiments, formula 2-2 is selected from the following groups:

[0087] In some embodiments, the organic compound is selected from the following compounds:

[0088] A second aspect of this application provides an organic electroluminescent device, including an anode, a cathode, and a functional layer disposed between the anode and the cathode; wherein the functional layer comprises the organic compound described in the first aspect of this application.

[0089] The organic compounds provided in this application 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.

[0090] In some embodiments, the functional layer includes an organic light-emitting layer, which comprises the organic compound. The organic light-emitting layer may be composed of the organic compound provided in this application, or it may be composed of the organic compound provided in this application and other materials.

[0091] According to a specific embodiment, the organic electroluminescent device is shown in FIG1. ​​The organic electroluminescent device may include an anode 100, a hole injection layer 310, a hole transport layer 321, a light-emitting auxiliary layer (hole auxiliary layer) 322, an organic light-emitting layer 330, an electron transport layer 340, an electron injection layer 350, and a cathode 200, which are stacked sequentially.

[0092] In this application, the anode 100 includes an anode material, which is preferably a material with a large work function that facilitates hole injection into the functional layer. Specific examples of anode materials include: metals such as nickel, platinum, vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; or conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, and polyaniline, but are not limited thereto. In some embodiments of this application, the anode includes indium tin oxide (ITO) as a transparent electrode for the anode.

[0093] In this application, 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:

[0094] In one embodiment, the hole transport layer 321 may be composed of HT-1.

[0095] In one embodiment, the light-emitting auxiliary layer 322 is composed of HT-2 or HT-3.

[0096] In some embodiments, a hole injection layer 310 is further disposed between the anode 100 and the hole transport layer 321 to enhance the ability to inject holes into the hole transport layer 321. The hole injection layer 310 may be selected from benzidine derivatives, starburst-like aryl amine compounds, phthalocyanine derivatives, or other materials; this application does not impose any special limitations on this. The material of the hole injection layer 310 may be selected from, for example, the following compounds or any combination thereof;

[0097] In one embodiment, the hole injection layer 310 is composed of PD and HT-1.

[0098] In this application, the organic light-emitting layer 330 may be composed of a single light-emitting material, or it may include a host material and a guest material (i.e., a doped material). In some embodiments, 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.

[0099] The host material of the organic light-emitting layer 330 may include metal chelating compounds, bis(styrene) derivatives, aromatic amine derivatives, dibenzofuran derivatives, or other types of materials. In some embodiments, the host material includes the organic compounds of this application.

[0100] The guest material of the organic light-emitting layer 330 can be a compound with a condensed aryl ring or its derivative, a compound with a heteroaryl ring or its derivative, an aromatic amine derivative, or other materials; this application does not impose any special limitations on this. The guest material is also called a dopant or dopant. According to the type of light emission, it can be divided into fluorescent dopant and phosphorescent dopant. Specific examples of phosphorescent dopant include, but are not limited to,

[0101] In one embodiment of this application, the organic electroluminescent device is a red organic electroluminescent device. In one embodiment, the host material of the organic light-emitting layer 330 comprises the organic compound of this application. The guest material is, for example, RD-1 or RD-2.

[0102] In one embodiment, the host material of the organic light-emitting layer 330 comprises the organic compounds of this application and

[0103] In one embodiment, the host material of the organic light-emitting layer 330 comprises the organic compounds of this application and

[0104] In one embodiment of this application, the organic electroluminescent device is a green organic electroluminescent device. In a more specific embodiment, the host material of the organic light-emitting layer 330 comprises the organic compound of this application.

[0105] 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 application 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:

[0106] In one embodiment of this application, the electron transport layer 340 may be composed of ET-1 and LiQ.

[0107] In this application, 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. In some embodiments, a metal electrode comprising magnesium and silver is included as the cathode.

[0108] In some embodiments, 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 this application, the electron injection layer 350 may include ytterbium (Yb).

[0109] A third aspect of this application provides an electronic device including the organic electroluminescent device described in the second aspect of this application.

[0110] According to one embodiment, as shown in FIG2, the provided electronic device is electronic device 400, which includes the aforementioned organic electroluminescent device. Electronic device 400 may 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.

[0111] The following examples illustrate the synthesis method of the organic compounds of this application, but this disclosure is not limited thereto.

[0112] Synthesis Examples

[0113] Those skilled in the art will recognize that the chemical reactions described herein can be suitably used to prepare many of the organic compounds of this application, and other methods for preparing the compounds of this application are considered to be within the scope of this application. For example, the synthesis of those non-illustrative compounds according to this application can be successfully accomplished by those skilled in the art through modification methods, such as appropriately protecting interfering groups, utilizing other known reagents besides those described herein, or making some conventional modifications to the reaction conditions. The compounds synthesized by methods not mentioned in this application are all commercially available starting materials.

[0114] Synthesis of Sub-a1:

[0115] Under a nitrogen atmosphere, 3-bromo-4-chlorodibenzofuran (19.60 g, 70 mmol) and tetrahydrofuran (dry, 200 mL) were added to a 500 mL three-necked flask; the system was cooled to -78 °C, and a solution of n-butyllithium (2.0 M n-hexane solution, 38.5 mL, 77 mmol) was added dropwise. After the addition was complete, the system was kept at -78 °C and stirred for 1 hour; while maintaining the temperature at -78 °C, anhydrous N,N-dimethylformamide (6.2 g, 84 mm) was added dropwise. After the addition of ol was complete, the mixture was kept at -78℃ for 1 hour, and then allowed to naturally warm to room temperature. Water was added to the reaction system to quench the reaction, and the mixture was stirred for 30 minutes. The mixture was extracted with dichloromethane (100 mL × 3 times), the organic phases were combined and dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by vacuum distillation to obtain the crude product. The crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as the mobile phase to finally obtain a white solid Sub-a1 (10.8 g, yield 67%).

[0116] Synthesis of Sub-b1:

[0117] Under a nitrogen atmosphere, Sub-a1 (11.5 g, 50 mmol), pinacol diborate (14.0 g, 55 mmol), sodium acetate (9.0 g, 110 mmol), and PEG 600 (120 mL) were added sequentially to a 500 mL three-necked flask. Stirring and heating were initiated, and when the system reached 40 °C, palladium dichloride bis(triphenylphosphine) dichloride (Pd(PPh3)2Cl2, 0.35 g, 0.50 mmol) was rapidly added. The mixture was then heated to reflux and stirred overnight. After cooling to room temperature, 100 mL of water was added, and the mixture was stirred thoroughly for 30 min. The mixture was filtered under reduced pressure, and the filter cake was washed with deionized water until neutral, then rinsed with 100 mL of anhydrous ethanol to obtain a gray solid crude product. The crude product was slurried once with n-heptane, dissolved in 200 mL of toluene, and then passed through a silica gel column to remove the catalyst. After concentration, a white solid Sub-b1 (8.40 g, yield 52%) was obtained.

[0118] Synthesis of Sub-c1:

[0119] Under a nitrogen atmosphere, 6-bromo-3-chlorodibenzo[B,D]furan (14.0 g, 50 mmol), Sub-b1 (17.7 g, 55 mmol), tetra(triphenylphosphine)palladium (0.58 g, 0.5 mmol), tetrabutylammonium bromide (TBAB, 1.61 g, 5 mmol), anhydrous sodium carbonate (10.60 g, 100 mmol), toluene (140 mL), anhydrous ethanol (35 mL), and deionized water (35 mL) were added sequentially to a 500 mL three-necked flask. Stirring and heating were started, and the mixture was refluxed for 8 h. After the system cooled to room temperature, it was extracted with dichloromethane (100 mL × 3 times). The organic phases were combined and dried over anhydrous magnesium sulfate. After filtration, the solvent was removed by vacuum distillation to obtain the crude product. The crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as the mobile phase to obtain a white solid Sub-c1 (12.6 g, yield 64%).

[0120] Referring to the synthesis of Sub-c1, Sub-c2 to Sub-c5 were synthesized by replacing 6-bromo-3-chlorodibenzo[B,D]furan with reactant A shown in Table 1.

[0121] Table 1: Synthesis of Sub-c2 to Sub-c5

[0122] Synthesis of Sub-d1:

[0123] Under a nitrogen atmosphere, (methoxymethyl)triphenylphosphonium chloride (51.25 g, 149.5 mmol), potassium tert-butoxide (18.10 g, 161 mmol), and anhydrous tetrahydrofuran (250 mL) were added to a 1000 mL three-necked flask. The system was cooled to -15 °C and maintained for 30 min. Then, Sub-Cl (51.5 g, 130 mmol) was weighed and dissolved in anhydrous tetrahydrofuran (250 mL). This solution was slowly added dropwise to the reaction system using a constant pressure dropping funnel, maintaining the temperature at -15 °C during the addition. After the addition was complete, the reaction was stirred at -15 °C for 1 h. The reaction system was then allowed to warm naturally to room temperature and extracted with dichloromethane (200 mL × 3 times). The organic phases were combined and dried over anhydrous magnesium sulfate. After filtration, the solvent was removed by vacuum distillation to obtain the crude product. The crude product was purified by silica gel column chromatography using n-heptane / dichloromethane as the mobile phase to obtain a red solid Sub-d1 (40.2 g, yield 73%).

[0124] Referring to the synthesis of Sub-d1, Sub-d2 to Sub-d5 were synthesized by replacing Sub-c1 with reactant B shown in Table 2.

[0125] Table 2: Synthesis of Sub-d2 to Sub-d5

[0126] Synthesis of Sub-e1:

[0127] Under a nitrogen atmosphere, Sub-d1 (50.9 g, 120 mmol), Eaton reagent (4.5 mL), and chlorobenzene (500 mL) were added sequentially to a 1000 mL three-necked flask. The mixture was heated to reflux and stirred for 4 h. After the reaction system cooled to room temperature, the reaction solution was poured into 1000 mL of deionized water, neutralized with saturated sodium hydroxide solution, and then extracted with dichloromethane (250 mL × 3 times). The organic phases were combined and dried over anhydrous magnesium sulfate. After filtration, the solvent was removed by vacuum distillation to obtain the crude product. The crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as the mobile phase to obtain a white solid Sub-e1 (32 g, yield 68%).

[0128] Referring to the synthesis of Sub-e1, Sub-e2 to Sub-e5 were synthesized by replacing Sub-d1 with reactant C shown in Table 3.

[0129] Table 3: Synthesis of Sub-e2 to Sub-e5

[0130] Synthesis of Sub-e6:

[0131] Under a nitrogen atmosphere, Sub-e4 (9.80 g, 25 mmol) and Benzene-d6 were added to a 1000 mL three-necked flask. The mixture was heated to 60 °C, and then trifluoromethanesulfonic acid (22.51 g, 150 mmol) was added. The mixture was then heated to boiling and stirred for 24 hours. After the reaction system cooled to room temperature, 50 mL of heavy water was added, and the mixture was stirred for 10 minutes. Then, a saturated aqueous solution of K3PO4 was added to neutralize the reaction mixture. The organic layer was extracted with dichloromethane (50 mL × 3 times), and the combined organic phases were dried over anhydrous sodium sulfate. After filtration, the solvent was removed by vacuum distillation to obtain the crude product. The crude product was purified by silica gel column chromatography using n-heptane / dichloromethane as the mobile phase to obtain a white solid Sub-e6 (7.80 g, yield 77%).

[0132] Synthesis of Sub-f1:

[0133] Under a nitrogen atmosphere, Sub-e1 (19.60 g, 50 mmol), pinacol diborate (14.0 g, 55 mmol), potassium acetate (10.8 g, 110 mmol), and 1,4-dioxane (200 mL) were added sequentially to a 500 mL three-necked flask. The mixture was stirred and heated until it reached 40 °C. Then, tris(dibenzylideneacetone)dipalladium (Pd2(dba)3, 0.46 g, 0.50 mmol) and 2-dicyclohexylphosphine-2′,4′,6′triisopropylbiphenyl (XPhos, 0.48 g, 1.0 mmol) were quickly added. The mixture was then heated to reflux and stirred overnight. After the system cooled to room temperature, 200 mL of water was added to the system and stirred thoroughly for 30 min. The mixture was then filtered under reduced pressure. The filter cake was washed with deionized water until neutral and then rinsed with 100 mL of anhydrous ethanol to obtain a gray solid crude product. The crude product was slurried once with n-heptane, then dissolved in 200 mL of toluene and passed through a silica gel column to remove the catalyst. After concentration, a white solid Sub-f1 (17.9 g, yield 74%) was obtained.

[0134] Referring to the synthesis of Sub-f1, Sub-f2 to Sub-f6 were synthesized by replacing Sub-e1 with reactant D shown in Table 4.

[0135] Table 4: Synthesis of Sub-f2 to Sub-f6

[0136] Synthesis of Sub-g1:

[0137] Under a nitrogen atmosphere, Sub-f1 (24.22 g, 50 mmol), m-chlorobromobenzene (9.57 g, 50 mmol), tetra(triphenylphosphine)palladium (0.58 g, 0.5 mmol), tetrabutylammonium bromide (TBAB, 1.61 g, 5 mmol), anhydrous sodium carbonate (10.60 g, 100 mmol), toluene (240 mL), anhydrous ethanol (60 mL), and deionized water (60 mL) were added sequentially to a 500 mL three-necked flask. Stirring and heating were initiated, and the mixture was refluxed for 8 h. After cooling to room temperature, the mixture was extracted with dichloromethane (100 mL × 3 times). The organic phases were combined and dried over anhydrous magnesium sulfate. After filtration, the solvent was removed by vacuum distillation to obtain the crude product. The crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as the mobile phase to obtain a white solid, Sub-g1 (19.20 g, yield 82%).

[0138] Following the synthesis method of Sub-g1, Sub-g2 to Sub-g5 were synthesized by replacing Sub-f1 with reactant E shown in Table 5 and replacing m-chlorobromobenzene with reactant F.

[0139] Table 5: Synthesis of Sub-g2 to Sub-g5

[0140] Synthesis of compound A003:

[0141] Under a nitrogen atmosphere, Sub-f1 (12.70 g, 26.25 mmol), 2-chloro-4-(2-naphthyl)-6-phenyl-1,3,5-triazine (7.94 g, 25 mmol), tetra(triphenylphosphine)palladium (0.29 g, 0.25 mmol), tetrabutylammonium bromide (TBAB, 0.8 g, 2.5 mmol), anhydrous sodium carbonate (5.3 g, 50 mmol), toluene (120 mL), anhydrous ethanol (30 mL), and deionized water (30 mL) were added sequentially to a 250 mL three-necked flask. Stirring and heating were started, and the mixture was refluxed for 16 h. After the system cooled to room temperature, it was extracted with dichloromethane (100 mL × 3 times). The organic phases were combined and dried over anhydrous magnesium sulfate. After filtration, the solvent was removed by vacuum distillation to obtain the crude product. The crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as the mobile phase to obtain a white solid A003 (12.4 g, yield 78%, m / z = 640.20 [M+H]). + ).

[0142] Referring to the synthesis of compound A003, reactant G was used instead of Sub-f1, and reactant H was used instead of 2-chloro-4-(2-naphthyl)-6-phenyl-1,3,5-triazine, as shown in Table 6, to synthesize the Class A compound of this application in Table 6.

[0143] Table 6: Synthesis of Class A Compounds in this Application

[0144] Synthesis of compound B001:

[0145] Under a nitrogen atmosphere, Sub-e1 (9.80 g, 25 mmol), N-phenyl-4-benzidine (CAS: 32228-99-2, 6.45 g, 26.25 mmol), tris(dibenzylacetone)palladium (0.916 g, 0.5 mmol), XPhos (2-dicyclohexylphosphine-2′,4′,6′triisopropylbiphenyl, 0.95 g, 1 mmol), sodium tert-butoxide (9.61 g, 50 mmol), and xylene (100 mL) were added sequentially to a 250 mL three-necked flask. The mixture was heated to reflux and stirred overnight. After the system cooled to room temperature, it was extracted with dichloromethane (100 mL × 3 times). The organic phases were combined and dried over anhydrous sodium sulfate. After filtration, the solvent was removed by vacuum distillation to obtain the crude product. The crude product was purified by silica gel column chromatography using n-heptane / dichloromethane as the mobile phase to obtain a yellow solid B001 (13.20 g; yield 88%, m / z = 602.21 [M+H]). + ).

[0146] Referring to the synthesis of compound B001, reactant G was used to replace Sub-e1 and reactant H was used to replace N-phenyl-4-benzidine, as shown in Table 7, to synthesize the Class B compound of this application in Table 7.

[0147] Table 7: Synthesis of Class B Compounds in this Application

[0148] NMR of compound A154: 1 H-NMR (400MHz, CD2Cl2) δ (ppm): 8.86 (s, 1H), 8.84-8.80 (m, 4H), 8.38 (d, 1H), 8.30 (d , 1H), 8.11-8.04(m, 4H), 7.89(d, 1H), 7.74(d, 1H), 7.68-7.42(m, 17H), 7.33(t, 1H);

[0149] NMR of compound B169: 1H-NMR (400MHz, CD2Cl2) δ (ppm): 8.26 (d, 1H), 8.15 (d, 2H), 8.10-8.05 (m, 2H), 8.02 (d, 1H), 7.99-7.92 (m, 2H), 7.91-7.86 (m, 2H), 7.65-7.22 (m, 13H), 7.17 (s, 1H), 7.12 (d, 2H), 7.11 (s, 1H), 7.09 (d, 2H), 7.03 (d, 1H), 7.00 (d, 1H), 6.59 (d, 2H).

[0150] Fabrication and evaluation of organic electroluminescent devices:

[0151] Example 1: Fabrication of a red organic electroluminescent device

[0152] First, anodizing pretreatment is performed through the following process: [The process is repeated in the original text, so the translation is incomplete.] On the ITO / Ag / ITO substrate, surface treatment is performed using ultraviolet light, ozone, and O2:N2 plasma to increase the work function of the anode. Alternatively, organic solvents can be used to clean the surface of the ITO substrate to remove impurities and oil.

[0153] On the experimental substrate (anode), PD:HT-1 was co-deposited at a deposition rate of 2%:98% to form a thickness of [missing information]. A hole injection layer (HIL) is formed, and then HT-1 is vacuum-deposited on the hole injection layer to form a thickness of [missing information]. A hole transport layer. Compound HT-2 is vacuum-deposited onto the hole transport layer to form a layer with a thickness of [missing information]. The light-emitting auxiliary layer.

[0154] Next, on the light-emitting auxiliary layer, compounds A003:RH-P:RD-2 were co-deposited at a deposition rate of 49%:49%:2% to form a layer with a thickness of [missing information]. The red light emitting layer (EML).

[0155] On the red light emitting layer, compounds ET-1 and LiQ were co-deposited at a 1:1 evaporation rate ratio to form... A thick electron transport layer (ETL) is formed by depositing Yb onto the electron transport layer to create a layer with a thickness of [thickness value missing]. An electron-injected layer (EIL) was formed, and then magnesium (Mg) and silver (Ag) were vacuum-deposited onto the electron-injected layer at a evaporation rate ratio of 1:9, forming a layer with a thickness of [missing information]. The cathode.

[0156] Furthermore, the vacuum evaporation thickness on the aforementioned cathode is [missing information]. The CPL forms a capping layer, thereby completing the fabrication of the red organic electroluminescent device.

[0157] Examples 2-41

[0158] Except that, when fabricating the light-emitting layer, compound X from Table 8 below is used instead of compound A003 in Example 1 and paired with RH-P as the main body of the light-emitting layer, the organic electroluminescent device is prepared using the same method as in Example 1.

[0159] Comparative Examples 1-3

[0160] Except that, when fabricating the light-emitting layer, compounds A, B, and C were used instead of compound A003 in Example 1, the organic electroluminescent device was prepared using the same method as in Example 1.

[0161] The structures of the main materials used in each embodiment and comparative example are as follows.

[0162] The performance of the red organic electroluminescent devices prepared in Examples 1-41 and Comparative Examples 1-3 was tested, 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.

[0163] Table 8

[0164] Referring to Table 8 above, compared with Comparative Examples 1 to 3 which used compounds A to C, the luminous efficiency (Cd / A) of the devices in Examples 1 to 41, which used the compounds of the present invention as the main material of the light-emitting layer of the red organic electroluminescent device, was increased by at least 12.2%, and the T95 lifetime was increased by at least 14.1%.

[0165] Example 42: Red Organic Electroluminescent Device

[0166] First, anodizing pretreatment is performed through the following process: [The process is repeated in the original text, so the translation is incomplete.] On the ITO / Ag / ITO substrate, surface treatment is performed using ultraviolet light, ozone, and O2:N2 plasma to increase the work function of the anode. Alternatively, organic solvents can be used to clean the surface of the ITO substrate to remove impurities and oil.

[0167] On the experimental substrate (anode), PD:HT-1 was co-deposited at a deposition rate of 2%:98% to form a thickness of [missing information]. A hole injection layer (HIL) is formed, and then HT-1 is vacuum-deposited on the hole injection layer to form a thickness of [missing information]. A hole transport layer. Compound HT-3 is vacuum-deposited onto the hole transport layer to form a layer with a thickness of [missing information]. The light-emitting auxiliary layer.

[0168] Next, on the light-emitting auxiliary layer, compounds B001:RH-N:RD were co-deposited at a deposition rate of 49%:49%:2% to form a layer with a thickness of [missing information]. The red light emitting layer (EML).

[0169] On the red light emitting layer, compounds ET-1 and LiQ were co-deposited at a 1:1 evaporation rate ratio to form... A thick electron transport layer (ETL) is formed by depositing Yb onto the electron transport layer to create a layer with a thickness of [thickness value missing]. An electron-injected layer (EIL) was formed, and then magnesium (Mg) and silver (Ag) were vacuum-deposited onto the electron-injected layer at a evaporation rate ratio of 1:9, forming a layer with a thickness of [missing information]. The cathode.

[0170] Furthermore, the vacuum evaporation thickness on the aforementioned cathode is [missing information]. The CP is used to complete the fabrication of a red organic electroluminescent device.

[0171] Examples 43-90

[0172] Except that when fabricating the red light emitting layer, compound Y from Table 9 is used instead of compound B001 from Example 42 as the host of the hole transport type emitting layer, the organic electroluminescent device is prepared using the same method as in Example 42.

[0173] Comparative Examples 4-6

[0174] Except that when fabricating the red light emitting layer, compounds D, E, and F were used to replace compound B001 in Example 42, the organic electroluminescent device was prepared using the same method as in Example 42.

[0175] The structures of the main materials used in each embodiment and comparative example are as follows.

[0176] The performance of the red organic electroluminescent devices prepared in Examples 42-90 and Comparative Examples 4-6 was tested, 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 9.

[0177] Table 9

[0178] Referring to Table 9 above, compared with Comparative Examples 4 to 6 which used compounds D to F, the luminous efficiency (Cd / A) of the devices in Examples 42 to 90, which used the compounds of the present invention as the main material of the light-emitting layer of the red organic electroluminescent device, was increased by at least 14.5%, and the T95 lifetime was increased by at least 11.7%.

Claims

1. An organic compound, characterized in that, The organic compound has a structure represented by Formula 1: Where X1 and X2 are the same or different, and are each independently selected from O, S or C(R) a R b ); Each R a and R b They may be the same or different, and each is independently selected from alkyl groups having 1 to 10 carbon atoms, haloalkyl groups having 1 to 10 carbon atoms, and deuteralkyl groups having 1 to 10 carbon atoms; Each of R1, R2, and R3 may be the same or different, and each is independently selected from hydrogen, 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 18 carbon atoms, deuterated aryl groups with 6 to 18 carbon atoms, heteroaryl groups with 3 to 12 carbon atoms, or... The structure shown is such that exactly one of R1, R2, and R3 is selected from... The structure shown; n1 represents the number of R1s, n2 represents the number of R2s, and n3 represents the number of R3s. n1 is selected from 1, 2, 3, 4, 5, or 6, n2 is selected from 1, 2, 3, or 4, and n3 is selected from 1, 2, 3, or 4. A is selected from either Equation 2-1 or Equation 2-2: L, L1, L2, L3 and L4 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms. The substituents in L, L1, L2, L3, and L4 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, deuteratedalkyl with 1 to 10 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, aryl with 6 to 18 carbon atoms, deuteratedaryl with 6 to 18 carbon atoms, heteroaryl with 3 to 12 carbon atoms, and cycloalkyl with 5 to 10 carbon atoms; Ar1, Ar2, Ar3 and Ar4 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms. The substituents in Ar1, Ar2, Ar3, and Ar4 may be the same or different, and each is independently selected from deuterium, cyano, halogen group, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuteratedalkyl with 1 to 10 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, aryl with 6 to 18 carbon atoms, deuterated aryl with 6 to 18 carbon atoms, heteroaryl with 3 to 12 carbon atoms, or cycloalkyl with 5 to 10 carbon atoms; optionally, any two adjacent substituents form a saturated or unsaturated 5 to 13-membered ring.

2. The organic compound according to claim 1, wherein, Ar1, Ar2, Ar3, and Ar4 may be the same or different, and each is independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraceneyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrene, substituted or unsubstituted perylene, substituted or unsubstituted Benz[c]phenanthryl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted carbazolyl, substituted or unsubstituted naphthobenzofuran, substituted or unsubstituted phenanthrenebenzofuran, substituted or unsubstituted benzooxazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted naphthooxazolyl, substituted or unsubstituted naphthothiazolyl; Optionally, the substituents in Ar1, Ar2, Ar3 and Ar4 may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, trideuterated methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, pyridyl, dibenzofuranyl, dibenzothiopheneyl or carbazoyl; optionally, any two adjacent substituents may form a benzene ring or a fluorene ring.

3. The organic compound according to claim 1 or 2, wherein, L, L1, L2, L3, and L4 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 dibenzothiophene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted fluorene, substituted or unsubstituted phenanthroline, and substituted or unsubstituted carbazolyl. Optionally, the substituents in L, L1, L2, L3 and L4 may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl or phenyl; Each R a and R b They may be the same or different, and each is independently selected from methyl, ethyl or trideuterated methyl.

4. The organic compound according to any one of claims 1 to 3, wherein, Ar1, Ar2, Ar3, and Ar4 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 any one of claims 1 to 4, wherein, L is selected from single bonds or the following groups: Optionally, L1, L2, L3, and L4 may be the same or different, and each may be independently selected from the group consisting of single bonds or the following groups:

6. The organic compound according to any one of claims 1 to 5, wherein, They may be the same or different, and each is independently selected from the following groups:

7. The organic compound according to any one of claims 1 to 6, wherein, Formula 2-1 is selected from the following groups: Optionally, Formula 2-2 is selected from the following groups:

8. The organic compound according to any one of claims 1 to 7, wherein, L is selected from the group consisting of single bonds or the following groups: Optionally, L1, L2, L3, and L4 may be the same or different, and each may be independently selected from the group consisting of single bonds or the following groups:

9. The organic compound according to any one of claims 1 to 8, wherein, Ar1, Ar2, Ar3, and Ar4 may be the same or different, and each is independently selected from the group consisting of the following groups:

10. The organic compound according to any one of claims 1 to 9, selected from the structures shown in formulas (1-1) to (1-12): In equations (1-1) to (1-12), X1 and X2 may be the same or different, and each is independently selected from O or S; n4 is selected from 0, 1, 2 or 3; n5 is selected from 0, 1, 2, 3, 4 or 5; Optionally, each of R1, R2 and R3 may be the same or different, and each may be independently selected from hydrogen, deuterium, cyano, fluorine, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl or phenyl.

11. The organic compound according to any one of claims 1 to 10, wherein the organic compound is selected from the group consisting of:

12. 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 the organic compound according to any one of claims 1 to 11; Optionally, the functional layer includes a light-emitting layer containing the organic compound.

13. An electronic device, characterized in that, Including the organic electroluminescent device as described in claim 12.

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