Organic compound, organic electroluminescent device, and electronic apparatus

Abstract

The present invention relates to the technical field of organic electroluminescent materials, and provides an organic compound, an organic electroluminescent device comprising same, and an electronic apparatus. The compound comprises a polycyclic conjugated parent core structure. When used as a host material of a light-emitting layer, the compound can improve carrier balance in the light-emitting layer, broaden the carrier recombination zone, and improve exciton generation and utilization efficiency, thereby increasing the luminous efficiency and service life of the device.

Description

Organic compounds and organic electroluminescent devices and electronic devices

[0001] Cross-reference of related applications

[0002] This application claims priority to Chinese patent application No. 202510216061.X, filed on February 25, 2025, 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 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 electroluminescent 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 organic electroluminescent layer, and holes on the anode side also move towards the organic electroluminescent 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 most significant challenges in existing organic light-emitting diodes (OLEDs) lie in their lifespan and efficiency. With the increasing size of displays, the driving voltage also increases, necessitating improvements in luminous efficiency and current efficiency. Research on improving the performance of OLEDs includes reducing the driving voltage, increasing luminous efficiency, and extending lifespan. To enhance OLED performance, multi-layered sandwich structures are typically employed in device design, consisting of an anode, a cathode, and multiple organic functional layers forming a complete device. The host material for the light-emitting layer can be one or more materials. This host material is capable of accepting and combining positively charged holes and negatively charged electrons for efficient energy transfer, typically possessing a high first triplet energy level, making it a crucial component of organic light-emitting diodes. Therefore, continued research and development of new materials are necessary to further improve the performance of organic light-emitting diodes. 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 electronic components and devices containing the same, wherein the organic compound can be used in organic electroluminescent devices to improve the performance of the devices.

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

[0008] In Equation 1, X is selected from O, S, or C(R) a R b );

[0009] 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;

[0010] Each of R1, R2, and R3 has exactly one selected from... The structure shown has R1, R2 and R3 that are the same or different, and each of them is independently selected from hydrogen, deuterium, cyano or halogen groups;

[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, or 4, n2 is selected from 1, 2, 3, or 4, and n3 is selected from 1, 2, 3, 4, 5, or 6.

[0012] A is selected from the group shown in Formula 2-1 or Formula 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, deuterated alkyl 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, 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 in Ar1, Ar2, Ar3, and Ar4 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] In some embodiments, the functional layer of the organic electroluminescent device of this application includes a light-emitting layer, which contains a light-emitting layer host material and a dopant, wherein the dopant includes at least one phosphorescent dopant optionally selected from Pt, Os, Re, Cu, Au or Ir complexes.

[0019] According to a third aspect of this application, an electronic device is provided, including the organic electroluminescent device described in the second aspect.

[0020] The compound structure provided in this application contains a bis(dibenzo-5-membered ring)benzene core structure, which is connected to a triazine fragment and a diarylamine fragment, respectively. The resulting compounds serve as electron-transporting and hole-transporting host materials, respectively. On the one hand, the bis(dibenzo-5-membered ring)benzene core has a suitable first excited triplet state energy level, making it suitable as a fragment for the red light host material in phosphorescent devices. On the other hand, the bis(dibenzo-5-membered ring)benzene core has a large conjugated area, which helps to enhance the intermolecular packing of the target compound and improve the charge carrier transport efficiency of the compound. When the compound of this application is used as an electron-transporting and / or hole-transporting host material in a hybrid host material, it can improve the carrier balance in the emitting layer, broaden the carrier recombination region, improve exciton generation and utilization efficiency, and improve the stability of the morphology of the emitting layer film, thereby improving the luminous efficiency and lifetime of the device. Attached Figure Description

[0021] 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.

[0022] Figure 1 is a schematic diagram of the structure of an organic electroluminescent device according to one embodiment of this application.

[0023] Figure 2 is a schematic diagram of the structure of an electronic device according to one embodiment of this application.

[0024] 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

[0025] Exemplary embodiments will now be described more fully with reference to the accompanying drawings. However, exemplary embodiments can be implemented in many forms and should not be construed as limited to the examples set forth herein; rather, these embodiments are provided to make this application more comprehensive and complete, and to fully convey the concept of exemplary embodiments to those skilled in the art. The described features, structures, or characteristics may be combined in any suitable manner in one or more embodiments. In the following description, numerous specific details are provided to give a full understanding of embodiments of this application.

[0026] In a first aspect, this application provides an organic compound having a structure as shown in Formula 1:

[0027] In Equation 1, X is selected from O, S, or C(R) a R b );

[0028] 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;

[0029] Each of R1, R2, and R3 has exactly one selected from... The structure shown has R1, R2 and R3 that are the same or different, and each of them is independently selected from hydrogen, deuterium, cyano or halogen groups;

[0030] 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, or 4, n2 is selected from 1, 2, 3, or 4, and n3 is selected from 1, 2, 3, 4, 5, or 6.

[0031] A is selected from the group shown in Formula 2-1 or Formula 2-2:

[0032] 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.

[0033] 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, deuterated alkyl 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, and cycloalkyl with 5 to 10 carbon atoms;

[0034] 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.

[0035] 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 in Ar1, Ar2, Ar3, and Ar4 form a saturated or unsaturated 5 to 13-membered ring.

[0036] 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.

[0037] 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.

[0038] 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.

[0039] In this application, "multiple" means two or more, such as two, three, four, five, six, etc.

[0040] In this application, saturated or unsaturated 5- to 13-membered rings refer to rings containing 5 to 13 ring atoms; examples of 5- to 13-membered rings include cyclopentane (5-membered ring), furan ring (5-membered ring), cyclohexane (6-membered ring), benzene ring (6-membered ring), naphthalene ring (10-membered ring), fluorene ring (13-membered ring), etc.

[0041] The hydrogen atoms in the compound structure of this application include various isotopes of hydrogen, such as hydrogen (H), deuterium (D), or tritium (T).

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

[0043] In this application, 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 with 6 to 30 carbon atoms may include, but are not limited to, phenyl, naphthyl, fluorenyl, and spirodifluorenyl. Anthrayl, phenanthrene, biphenyl, terphenyl, triphenylene Peryl, benzo[9,10]phenanthryl, pyrene Benzofluoranthyl, base Benz[c]phenanthrene wait.

[0044] 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.

[0045] In this application, terphenyl includes

[0046] 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.

[0047] 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.

[0048] 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.

[0049] 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.

[0050] 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 or polycyclic heteroaryl group; in other words, a heteroaryl group can be a single aromatic ring system or a system of multiple aromatic rings linked by carbon-carbon bonds, and any aromatic ring system can be a single aromatic monocyclic ring or a fused aromatic ring. For example, heteroaryl groups with 3 to 30 carbon atoms can include thiophene, furanyl, pyrrole, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinel, pyridazinyl, quinolinyl, quinazolinyl, quinoxolinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, iso Quinolinyl, indolyl, carbazole, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazole, benzothiophene, dibenzothiophene, thiophene-thiophene, benzofuranyl, phenanthrolinel, isoxazolyl, thiadiazolyl, phenothiazinyl, silanyl, dibenzofuranyl, and N-phenylcarbazole, N-pyridylcarbazole, N-methylcarbazole, naphthobenzofuranyl (e.g.) ), phenanthrenebenzofuranyl (e.g.) (and others, but not limited to these.)

[0051] 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.

[0052] In this application, the number of carbon atoms in the substituted or unsubstituted heteroaryl (hybrid aryl) 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 is a substituted or unsubstituted heteroaryl with 3 to 30 carbon atoms; in other embodiments, the substituted or unsubstituted heteroaryl is a substituted or unsubstituted heteroaryl with 3 to 18 total carbon atoms; and in still other embodiments, the substituted or unsubstituted heteroaryl is a substituted or unsubstituted heteroaryl with 5 to 12 total carbon atoms.

[0053] 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.

[0054] 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.

[0055] 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.

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

[0057] In this application, specific examples of trialkylsilyl groups include, but are not limited to, trimethylsilyl, triethylsilyl, etc.

[0058] In this application, specific examples of alkyl halogens include, but are not limited to, trifluoromethyl.

[0059] In this application, specific examples of deuterated alkyl groups include, but are not limited to, trideuterated methyl groups.

[0060] 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, or 10. Specific examples of cycloalkyl groups include, but are not limited to, cyclopentyl, cyclohexyl, and adamantyl.

[0061] In this application, the number of carbon atoms in the deuterated aryl group with 6 to 18 carbon atoms is, for example, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, or 18. Specific examples of deuterated aryl groups include, but are not limited to, pentadeuterated phenyl, nonadeuterated naphthyl, and undeuterated biphenyl.

[0062] 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.

[0063] For another 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.

[0064] 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):

[0065] In some embodiments, the organic compounds of this application are selected from structures represented by any of the following formulas (1-1) to (1-18):

[0066] In equations (1-1) to (1-18), X is selected from O or S; n1 is selected from 1, 2, 3 or 4; n2 is selected from 1, 2, 3 or 4; n3 is selected from 1, 2, 3, 4, 5 or 6; n4 and n5 are each independently selected from 1, 2 or 3; n6 is selected from 1, 2, 3, 4 or 5.

[0067] Each of R1, R2, and R3 may be the same or different, and each is independently selected from hydrogen, deuterium, cyano or fluorine.

[0068] The parent nucleus of this type of di(dibenzo-p-5-membered ring)benzene possesses suitable energy levels and stereoconfigurations, enabling it to be paired with metal complex phosphorescent dopants to exhibit superior energy transport performance. When used as the host material for electron transport-type luminescent layers in red phosphorescent OLED devices, the compounds shown in formulas (1-1), (1-5), (1-6), and (1-8) demonstrate superior luminous efficiency, while the compounds shown in formulas (1-2), (1-3), (1-4), (1-7), and (1-9) exhibit better lifetime characteristics in terms of T95 lifetime. When used as the host material for hole transport type emitting layers in red phosphorescent OLED devices, the compounds shown in formulas (1-10), (1-11), (1-14), (1-17), and (1-18) exhibit better performance in terms of luminous efficiency, while the compounds shown in formulas (1-12), (1-13), (1-15), and (1-16) show better lifetime characteristics in terms of T95 lifetime.

[0069] 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.

[0070] 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.

[0071] 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.

[0072] 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... Benzyl, substituted or unsubstituted benzo[c]phenanthryl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted naphthobenzofuranyl, substituted or unsubstituted phenanthrenebenzofuranyl, substituted or unsubstituted benzooxazolyl, substituted or unsubstituted benzothiazoyl, substituted or unsubstituted pyridyl.

[0073] 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.

[0074] In some embodiments, Ar1, Ar2, Ar3, and Ar4 may be the same or different, and each is independently selected from the group consisting of:

[0075] In some embodiments, Ar1, Ar2, Ar3, and Ar4 may be the same or different, and each is independently selected from the group consisting of:

[0076] 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.

[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 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.

[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, 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.

[0079] 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.

[0080] 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.

[0081] 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.

[0082] In some embodiments, L is selected from single bonds or the following groups:

[0083] In some embodiments, L is selected from the group consisting of single bonds or the following groups:

[0084] 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:

[0085] 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:

[0086] In some implementations... They may be the same or different, and each is independently selected from the following groups:

[0087] In some embodiments, the formula 2-1 group Selected from the group consisting of the following groups:

[0088] In some embodiments, the formula 2-2 group Selected from the group consisting of the following groups:

[0089] In some embodiments, the organic compounds described in this application are selected from the group consisting of the following compounds:

[0090] 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.

[0091] 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.

[0092] 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.

[0093] 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.

[0094] 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, a transparent electrode comprising indium tin oxide (ITO) is used as the anode.

[0095] 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:

[0096] In one embodiment, the hole transport layer 321 may be composed of HT-1.

[0097] In one embodiment, the light-emitting auxiliary layer 322 is composed of HT-2 or HT-3.

[0098] 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 particular limitation on this. In one specific embodiment, the material of the hole injection layer 310 is selected, for example, from the following compounds or any combination thereof;

[0099] In one embodiment, the hole injection layer 310 is composed of PD and HT-1.

[0100] 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.

[0101] 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.

[0102] 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,

[0103] 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.

[0104] In one embodiment, the host material of the organic light-emitting layer 330 comprises the organic compounds of this application and

[0105] In one embodiment, the host material of the organic light-emitting layer 330 comprises the organic compounds of this application and

[0106] 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.

[0107] 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:

[0108] In one embodiment of this application, the electron transport layer 340 may be composed of ET and LiQ.

[0109] In this application, the cathode 200 may include a cathode material that has a small work function and facilitates electron injection into the functional layer. Specific examples of cathode materials include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; or multilayer materials such as LiF / Al, Liq / Al, LiO2 / Al, LiF / Ca, LiF / Al, and BaF2 / Ca. In some embodiments, a metal electrode containing magnesium and silver is used as the cathode.

[0110] 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).

[0111] A third aspect of this application provides an electronic device including the organic electroluminescent device described in the second aspect of this application.

[0112] 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.

[0113] The following examples illustrate the synthesis method of the organic compounds of this application, but this disclosure is not limited thereto.

[0114] Synthesis Examples

[0115] 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.

[0116] Synthesis of Sub-a1:

[0117] Under a nitrogen atmosphere, 19.60 g (70 mmol) of 3-bromo-4-chlorodibenzofuran and 200 mL (dry) of tetrahydrofuran were added to a 500 mL three-necked flask. The system was cooled to -78 °C, and 38.5 mL (77 mmol) of n-butyllithium solution (2.0 M n-hexane solution) was added dropwise. After the addition was complete, the mixture was kept at -78 °C and stirred for 1 hour. Anhydrous N,N-dimethylformamide (6.2 g, 84 mmol) was added dropwise while maintaining the temperature at -78 °C. After the addition was complete, the mixture was kept at -78°C for 1 hour, and then allowed to warm to room temperature naturally. 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), and the combined organic phases were dried over anhydrous magnesium sulfate. The solvent was removed by vacuum distillation after filtration to obtain the crude product. The crude product was purified by silica gel column chromatography using a mixed solvent of dichloromethane and n-heptane as the mobile phase to finally obtain a white solid Sub-a1 (10.8 g, yield 67%).

[0118] Referring to the synthesis of Sub-a1, Sub-a2 was synthesized by replacing 3-bromo-4-chlorodibenzofuran with reactant A shown in Table 1.

[0119] Table 1: Synthesis of Sub-a2

[0120] Synthesis of Sub-b1:

[0121] 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. 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.

[0122] Referring to the synthesis of Sub-b1, Sub-b2 was synthesized by replacing Sub-a1 with reactant B shown in Table 2.

[0123] Table 2: Synthesis of Sub-b2

[0124] Synthesis of Sub-c1:

[0125] Under a nitrogen atmosphere, 1-bromo-3-chlorodibenzofuran (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 heated to reflux and stirred 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 a mixed solvent of dichloromethane and n-heptane as the mobile phase to obtain a white solid, Sub-c1 (10.7 g, yield 54%).

[0126] Referring to the synthesis of Sub-c1, Sub-b1 was synthesized by replacing reactant C shown in Table 3 with reactant D with reactant D, and Sub-c2 to Sub-c9 were synthesized.

[0127] Table 3: Synthesis of Sub-c2 to Sub-c9

[0128] Synthesis of Sub-d1:

[0129] 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 completed, the reaction was stirred at -15 °C for 1 h. The reaction system was then allowed to warm naturally to room temperature, extracted with dichloromethane (200 mL × 3 times), and the combined organic phases were 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 a mixed solvent of dichloromethane and n-heptane as the mobile phase to obtain a red solid Sub-d1 (42.5 g, yield 77%).

[0130] Referring to the synthesis of Sub-d1, Sub-d2 to Sub-d9 were synthesized by replacing Sub-c1 with reactant E shown in Table 4.

[0131] Table 4: Synthesis of Sub-d2 to Sub-d4

[0132] Synthesis of Sub-e1:

[0133] 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 combined organic phases were 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 a mixed solvent of dichloromethane and n-heptane as the mobile phase to obtain a white solid Sub-e1 (27.3 g, yield 58%).

[0134] Referring to the synthesis of Sub-e1, Sub-e2 to Sub-e9 were synthesized by replacing Sub-d1 with reactant F shown in Table 5.

[0135] Table 5: Synthesis of Sub-e2 to Sub-e5

[0136] Synthesis of Sub-e10:

[0137] Under a nitrogen atmosphere, Sub-e7 (9.80 g, 25 mmol) and Benzene-D6 were added to a 100 mL three-necked flask. The mixture was heated to 60 °C, and then trifluoromethanesulfonic acid (22.51 g, 150 mmol) was added. The mixture was then heated to boiling and stirred for 24 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 solution. The organic layer was extracted with dichloromethane (50 mL × 3 times). The combined organic phases were dried over anhydrous sodium sulfate, filtered, and the solvent was removed by vacuum distillation to obtain the crude product. The crude product was purified by silica gel column chromatography using a mixed solvent of dichloromethane and n-heptane as the mobile phase to obtain a white solid, Sub-e10 (6.80 g, yield 67%).

[0138] Synthesis of Sub-f1:

[0139] 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. Stirring and heating were started, and once the system reached 40 °C, tris(dibenzylacetone)dipalladium (Pd2(dba)3) (0.46 g, 0.50 mmol) and 2-dicyclohexylphosphine-2',4',6'trimethylammonium chloride (DBA) were quickly added. Isopropylbiphenyl (Xphos, 0.48 g, 1.0 mmol) was heated to reflux and stirred overnight. After the system cooled to room temperature, 200 mL of water was added, and the mixture was 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 crude product as a gray solid. 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-f1 (17.2 g, yield 71%) was obtained.

[0140] Referring to the synthesis of Sub-f1, Sub-f2 to Sub-f10 were synthesized by replacing Sub-e1 with reactant G shown in Table 6.

[0141] Table 6: Synthesis of Sub-f2 to Sub-f10

[0142] Synthesis of compound A003:

[0143] Under a nitrogen atmosphere, Sub-f4 (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), tetrahydrofuran (30 mL), and deionized water (30 mL) were added sequentially to a 250 mL three-necked flask. Stirring and heating were initiated, and the mixture was refluxed for 16 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 a mixed solvent of dichloromethane and n-heptane as the mobile phase, yielding a white solid A003 (12.0 g, yield 75%, m / z = 640.20 [M+H]). + ).

[0144] Referring to the synthesis of compound A003, reactant H was used instead of Sub-f4, and reactant J was used instead of 2-chloro-4-(2-naphthyl)-6-phenyl-1,3,5-triazine, as shown in Table 7, to synthesize the Class A compounds of this application listed in Table 7.

[0145] Table 7: Synthesis of Class A Compounds in this Application

[0146] Synthesis of compound B001:

[0147] Under a nitrogen atmosphere, Sub-e4 (9.80 g, 25 mmol), di(4-biphenyl)amine (8.44 g, 26.25 mmol), tris(dibenzylacetone)palladium (0.916 g, 0.5 mmol), 2-dicyclohexylphosphine-2',4',6'triisopropylbiphenyl (Xphos, 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 combined organic phases were dried over anhydrous sodium sulfate, filtered, and the solvent was removed by vacuum distillation to obtain the crude product. The crude product was purified by silica gel column chromatography using a mixed solvent of dichloromethane and n-heptane as the mobile phase, yielding a yellow solid B001 (13.2 g; yield 78%, m / z = 678.24 [M+H]). + ).

[0148] Referring to the synthesis of compound B001, reactant K as shown in Table 8 was used to replace Sub-e4, and reactant L was used to replace di(4-biphenyl)amine to synthesize the Class B compounds of this application listed in Table 8.

[0149] Table 8: Synthesis of Class B Compounds in this Application

[0150] NMR of compound A076: 1¹H-NMR (400MHz, CD₂Cl₂) δppm: 8.90 (s, 1H), 8.85 (s, 1H), 8.81 (d, 2H), 8.69 (d, 1H), 8.46 (d, 1H), 8.40–8.27 (m, 3H), 8.21 (d, 1H), 8.04 (d, 1H), 7.78–7.71 (m, 2H), 7.67–7.46 (m, 9H), 7.45–7.31 (m, 3H); NMR of compound B036: 1 ¹H-NMR (400MHz, CD₂Cl₂) δppm: 8.38-8.32 (m, 2H), 8.21 (d, 1H), 8.09-7.96 (m, 3H), 7.83 (d, 1H), 7.59-7.49 (m, 11H), 7.47-7.37 (m, 9H), 7.35-7.27 (m, 3H), 6.91 (s, 1H), 6.82-6.73 (m, 2H), 6.52 (d, 2H). 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 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 stains.

[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 were co-deposited in a ratio of 49%:49%:2% to form a layer with a thickness of [missing information]. The red light emitting layer (EML).

[0155] On the light-emitting layer, compounds ET and LiQ are co-deposited at a 1:1 evaporation rate 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 mixed at a evaporation rate of 1:9 and vacuum-deposited onto the electron-injected layer to form a layer with a thickness of [missing information]. The cathode.

[0156] Furthermore, the vacuum evaporation thickness on the aforementioned cathode is [missing information]. The CP 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 9 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 9.

[0163] Table 9

[0164] Referring to Table 9 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 15.1%, and the T95 lifetime was increased by at least 15.6%.

[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 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 stains.

[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 in a ratio of 49%:49%:2% to form a layer with a thickness of [missing information]. The red light emitting layer (EML).

[0169] On the light-emitting layer, compounds ET and LiQ are co-deposited at a 1:1 evaporation rate 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 mixed at a evaporation rate of 1:9 and vacuum-deposited onto the electron-injected layer to form 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 43-92

[0172] Except that when fabricating the red light emitting layer, compound Y from Table 10 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 42-92 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 10.

[0177] Table 10

[0178] Referring to Table 10 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 92, 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 14.4%, and the T95 lifetime was increased by at least 14.8%.

Claims

1. An organic compound, characterized in that, The organic compound has a structure as shown in formula (1): Where X is 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 has exactly one selected from... The structure shown has the same or different R1, R2 and R3, and each of them is independently selected from hydrogen, deuterium, cyano or halogen groups; 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, or 4, n2 is selected from 1, 2, 3, or 4, and n3 is selected from 1, 2, 3, 4, 5, or 6. A is selected from the group shown in Formula 2-1 or Formula 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, deuterated alkyl 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, 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 in Ar1, Ar2, Ar3, and Ar4 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 dibenzofuranyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted naphthobenzofuranyl, substituted or unsubstituted phenanthrenebenzofuranyl, substituted or unsubstituted benzooxazolyl, substituted or unsubstituted benzothiazoyl, substituted or unsubstituted pyridinyl; 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 group Selected from the group consisting of the following groups: Optionally, the formula 2-2 group Selected from the group consisting of 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, wherein the organic compound is selected from any structure shown in formula (1-1) to formula (1-18): In equations (1-1) to (1-18), X is selected from O or S; n1 is selected from 1, 2, 3 or 4; n2 is selected from 1, 2, 3 or 4; n3 is selected from 1, 2, 3, 4, 5 or 6; n4 and n5 are each independently selected from 1, 2 or 3; n6 is selected from 1, 2, 3, 4 or 5. Each of R1, R2, and R3 may be the same or different, and each is independently selected from hydrogen, deuterium, cyano or fluorine.

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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