Organic compounds and organic electroluminescent devices containing them, and electronic devices

Abstract

This application relates to the technical field of organic electroluminescent materials and provides organic compounds, organic electroluminescent devices, and electronic devices. The organic compounds of this application have the structure shown in Formula 1 and can significantly improve the performance of the devices. JPEG2026521481000083.jpg3442 Formula I

Description

Technical Field

[0001] [Cross-reference to Related Applications] This application claims the priority of the Chinese patent application with application number CN202410373346.X filed on March 28, 2024, the entire content of which is hereby incorporated by reference and made a part of this application.

[0002] This application relates to the technical field of organic electroluminescent materials, and particularly to organic compounds, organic electroluminescent devices containing the same, and electronic devices.

Background Art

[0003] Currently, with the rapid development of organic synthesis and materials science, organic electroluminescent device (OLED) display technology has already been applied in fields such as smartphones and tablet PCs, and its application fields are further expanding to large sizes such as televisions. The optoelectronic functional materials applied to OLED devices can be divided into charge injection / transport materials and light-emitting materials according to their uses. According to the functions of the materials in each layer, the charge injection / transport materials can be further divided into electron injection / transport materials, electron blocking materials, hole injection / transport materials, and hole blocking materials. Therefore, the optoelectronic functional material film layers constituting the OLED device include at least a structure of two or more layers. The OLED device structure applied in the industry includes various film layers such as a hole injection layer, a hole transport layer, an electron blocking layer, an organic light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer, and the types and combination forms of the materials have the characteristics of richness and diversity. Also, for the combination of OLED devices with different structures, the optoelectronic functional materials used have strong selectivity, and the performance expressions of the same material in devices with different structures may be completely different.

[0004] In general, in host material / dopant systems, the host material significantly affects the efficiency and lifespan of the light-emitting device, making the selection of the host material crucial. A host material with superior performance should have an appropriate molecular weight, high glass transition temperature and thermal decomposition temperature, high electrochemical stability, and good interfacial contact with adjacent functional layer materials. For light-emitting host materials, good carrier transport capability is required, and having an appropriate triplet energy level ensures that energy can be efficiently transferred from the host material to the guest material during the light-emitting process, thereby achieving high device efficiency.

[0005] In conventional organic electroluminescent devices, the main challenges are lifespan and efficiency. As displays become larger in area, the driving voltage also increases, and both luminous efficiency and current efficiency need to be improved. Therefore, it is necessary to continue developing new materials to further improve the performance of organic electroluminescent devices. [Overview of the project]

[0006] In response to the above-mentioned problems in the prior art, the object of this application is to provide an organic compound, an organic electroluminescent device containing the same, and an electronic device in which the performance of the device can be improved by using the organic compound in the organic electroluminescent device.

[0007] A first aspect of this application provides an organic compound having the structure shown in Formula 1. JPEG2026521481000002.jpg3442 Formula I However, X and Y are selected from single bonds, O, or S, and one of X and Y is selected from O or S, and the other is a single bond. L, L1, and L2 are the same or different, and each is independently selected from single bonds, substituted or unsubstituted arylene groups having 6 to 30 carbon atoms, and substituted or unsubstituted heteroarylene groups having 3 to 30 carbon atoms. Ar1 and Ar2 are the same or different, and are independently selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms and substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms. The substituents in L, L1, L2, Ar1, and Ar2 are the same or different and are independently selected from deuterium, a cyano group, a halogen group, a C1-C10 alkyl group, a C1-C10 halogenated alkyl group, a C1-C10 deuterated alkyl group, a C3-C12 trialkylsilyl group, a C6-C20 aryl group, or a C3-C20 heteroaryl group.

[0008] A second aspect of this application provides an organic electroluminescent device comprising an anode and a cathode provided opposite to each other, and a functional layer provided between the anode and the cathode, wherein the functional layer contains the above-mentioned organic compound.

[0009] A third aspect of this application provides an electronic device including the organic electroluminescent device described in the second aspect.

[0010] The compound in this application has a phenanthryl group ( Based on JPEG2026521481000003.jpg1921), a parent structure is formed by condensation of benzofuran or benzothiophene at the 1st and 2nd positions, and an electron-withdrawing heteroaryl group of a triazine is linked at the 3rd position, making it usable as an electron-transporting red light host material. First, the parent structure, in which benzofuran or benzothiophene is condensed at the 1st and 2nd positions of the phenanthryl group, has a relatively suitable first excited triplet energy level and is suitable as a fragment of a light-emitting host material. Second, the relatively large conjugated area of ​​the parent structure and the presence of lone pairs of electrons on the oxygen or sulfur atom in the parent structure can significantly enhance the carrier transport performance of the target compound. Furthermore, the electron-withdrawing heteroaryl group of a triazine linked at the 3rd position and the presence of the hydrogen atom at its ortho position and the lone pairs of electrons on the oxygen / sulfur atom can relatively increase the degree of strain of the molecule, thereby conferring relatively good film-forming properties to the compound of this application. Therefore, when the compound of this application is used as an electron transport host material in a hybrid red light host material, it is possible to improve the carrier balance in the light-emitting layer, expand the carrier recombination region, improve the generation and utilization efficiency of excitons, and improve the luminescence efficiency and lifetime of the device. [Brief explanation of the drawing]

[0011] The drawings are provided to provide a further understanding of this application, constitute part of the specification, and are used in conjunction with the following specific embodiments to interpret this application, but do not constitute any limitation to this application. [Figure 1] This is a schematic diagram of the structure of an organic electroluminescent device according to one embodiment of this application. [Figure 2] This is a schematic diagram of the structure of an electronic device according to one embodiment of this application. [Modes for carrying out the invention]

[0012] Illustrative embodiments will be described in detail below with reference to the drawings. However, the illustrative embodiments can be carried out in various forms and should not be understood as being limited to the examples described herein. On the contrary, by providing these embodiments, the application becomes more comprehensive and complete, and the concept of the illustrative embodiments is fully communicated to those skilled in the art. The described features, structures, or characteristics can be combined in one or more embodiments in any suitable manner. The following description provides many specific details in order to fully understand the embodiments of the application.

[0013] In a first embodiment, the present application provides a compound having the structure shown in formula I. JPEG2026521481000004.jpg3442 Formula I However, X and Y are selected from single bonds, O, or S, and one of X and Y is selected from O or S, and the other is a single bond. L, L1, and L2 are the same or different, and each is independently selected from single bonds, substituted or unsubstituted arylene groups having 6 to 30 carbon atoms, and substituted or unsubstituted heteroarylene groups having 3 to 30 carbon atoms. Ar1 and Ar2 are the same or different, and are independently selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms and substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms. The substituents in L, L1, L2, Ar1, and Ar2 are the same or different and are independently selected from deuterium, a cyano group, a halogen group, a C1-C10 alkyl group, a C1-C10 halogenated alkyl group, a C1-C10 deuterated alkyl group, a C3-C12 trialkylsilyl group, a C6-C20 aryl group, or a C3-C20 heteroaryl group.

[0014] In this application, X and Y are selected from single bonds, O, or S, and one of X and Y is selected from O or S, and the other is a single bond; that is, when X is O, Y is a single bond; when X is S, Y is a single bond; when Y is O, X is a single bond; and when Y is S, X is a single bond.

[0015] In this application, the explanatory phrases "each... independently," "...each independently," and "...each independently" are interchangeable and should be understood in a broad sense. They may refer to specific choices expressed between the same symbols in different bases that do not influence each other, or they may refer to specific choices expressed between the same symbols in the same base that do not influence each other. For example, In "JPEG2026521481000005.jpg2547", each q is independently 0, 1, 2, or 3, and each R'' is independently selected from hydrogen, deuterium, fluorine, and chlorine, meaning that formula Q-1 represents that there are q substituents R'' on a benzene ring, each R'' may be the same or different, and the choices of R'' do not influence each other; formula Q-2 represents that there are q substituents R'' on each benzene ring of biphenyl, the number q of R'' substituents on two benzene rings may be the same or different, each R'' may be the same or different, and the choices of R'' do not influence each other.

[0016] 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 convenience of explanation, substituents will be collectively referred to as Rc). For example, "substituted or unsubstituted aryl group" means an aryl group having substituent Rc or an unsubstituted aryl group. Here, the substituent, i.e., Rc, may be, for example, deuterium, halogen group, cyano group, alkyl group, cycloalkyl group, aryl group, heteroaryl group, deuterated aryl group, halide aryl group, trialkylsilyl group, halide alkyl group, or deuterated alkyl group. The number of substituent Rc may be one or more. When two substituent Rc are linked to the same atom, these two substituent Rc may exist independently or may be linked to each other to form a ring with the atom. When two adjacent substituent Rc are present on a functional group, these two adjacent substituent Rc may exist independently or may condense with the functional group to which they are linked to form a ring.

[0017] In this application, "plural" means two or more, for example, two, three, four, five, six, etc.

[0018] The hydrogen atoms in the structure of the compounds of this application include various isotope atoms of hydrogen element, such as hydrogen (H), deuterium (D) or tritium (T).

[0019] In this application, the number of carbon atoms of a substituted or unsubstituted functional group refers to all the carbon atoms. For example, when L1 is a substituted arylene group with 12 carbon atoms, the total number of carbon atoms of the arylene group and its substituents is 12.

[0020] In this application, the aryl group refers to any functional group or substituent derived from an aromatic carbon ring. The aryl group may be a monocyclic aryl group (such as a phenyl group) or a polycyclic aryl group. In other words, the aryl group may be a monocyclic aryl group, a fused-ring aryl group, two or more monocyclic aryl groups conjugated through a carbon-carbon bond, a monocyclic aryl group and a fused-ring aryl group conjugated through a carbon-carbon bond, or two or more fused-ring aryl groups conjugated through a carbon-carbon bond. That is, unless otherwise specified, two or more aromatic groups conjugated through a carbon-carbon bond can also be regarded as the aryl groups of this application. Here, the fused-ring aryl group may include, for example, a bicyclic fused aryl group (such as a naphthyl group), a tricyclic fused aryl group (such as a phenanthryl group, a fluorenyl group, an anthryl group), 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 group, naphthyl group, fluorenyl group, spirobifluorenyl group, anthryl group, phenanthryl group, biphenyl group, terphenyl group, triphenylenyl group, perylenyl group, benzo[9,10]phenanthryl group, pyrenyl group, benzofluoranthenyl group, chrysenyl group, etc.

[0021] In this application, such an arylene group refers to a divalent group formed by the aryl group losing one or more hydrogen atoms.

[0022] In this application, a substituted aryl group may be one in which one or more hydrogen atoms in an aryl group are substituted with groups such as deuterium, halogen groups, cyano groups, aryl groups, heteroaryl groups, trialkylsilyl groups, alkyl groups, cycloalkyl groups, alkyl halides, deuterated alkyl groups, aryl halides, or aryl deuterated groups. It should be understood that the carbon number of a substituted aryl group refers to the total carbon number of the aryl group and its substituents. For example, a substituted aryl group with 18 carbon atoms means that the aryl group and its substituents have a total of 18 carbon atoms.

[0023] In this application, the fluorenyl group may be substituted with one or more substituents. If the fluorenyl group is substituted, the substituted fluorenyl group is The file name may also be JPEG2026521481000006.jpg2091, but is not limited to these.

[0024] In this application, a heteroaryl group refers to a monovalent aromatic ring or a derivative thereof containing 1, 2, 3, 4, 5, 6, or 7 heteroatoms in the ring, and the heteroatoms may be one or more of B, O, N, P, Si, Se, and S. The heteroaryl group may be a monocyclic heteroaryl group or a polycyclic heteroaryl group; in other words, the heteroaryl group may be a single aromatic ring system or a plurality of aromatic ring systems conjugated via carbon-carbon bonds, and any aromatic ring system may be one aromatic monoring or one aromatic fused ring. Examples of heteroaryl groups include thienyl, furanyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridadinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, and indoquinyl. The group may include, but is not limited to, a lyl group, a carbazolyl group, a benzoxazolyl group, a benzimidazolyl group, a benzothiazolyl group, a benzocarbazolyl group, a benzothienyl group, a dibenzothienyl group, a thienothienyl group, a benzofuranyl group, a phenanthrolinyl group, an isoxazolyl group, a thiadiazolyl group, a phenothiazinyl group, a silafluorenyl group, a dibenzofuranyl group, and an N-phenylcarbazolyl group, an N-pyridylcarbazolyl group, an N-methylcarbazolyl group, etc. Here, the thienyl group, the furanyl group, the phenanthrolinyl group, etc. are single aromatic ring type heteroaryl groups, while the N-phenylcarbazolyl group and the N-pyridylcarbazolyl group are polycyclic type heteroaryl groups conjugated by carbon-carbon bonds.

[0025] In this application, such heteroarylene group refers to a divalent group formed by the loss of one or more hydrogen atoms from a heteroaryl group.

[0026] In this application, a substituted heteroaryl group may be one in which one or more hydrogen atoms in the heteroaryl group are substituted with groups such as deuterium atoms, halogen groups, cyano groups, aryl groups, heteroaryl groups, trialkylsilyl groups, alkyl groups, alkyl halides, deuterated alkyl groups, aryl halides, and aryl deuterated groups. Specific examples of aryl-substituted heteroaryl groups include, but are not limited to, phenyl-substituted dibenzofuranyl groups, phenyl-substituted dibenzothienyl groups, and phenyl-substituted pyridyl groups. It should be understood that the carbon number of a substituted heteroaryl group refers to the total carbon number of the heteroaryl group and the substituents in the heteroaryl group.

[0027] In this application, the number of carbon atoms in the aryl group as a substituent may be 6 to 20, for example, the number of carbon atoms may be 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20. Specific examples of the aryl group as a substituent include, but are not limited to, phenyl, biphenyl, naphthyl, anthryl, and chrysenyl groups.

[0028] In this application, the number of carbon atoms in the heteroaryl group as a substituent may be 3 to 20. For example, the number of carbon atoms may be 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20. Specific examples of heteroaryl groups as substituents include, but are not limited to, pyridyl, pyrimidyl, carbazolyl, dibenzofuranyl, dibenzothienyl, quinolinyl, quinazolinyl, quinoxalinyl, and isoquinolinyl groups.

[0029] In this application, the number of carbon atoms in an alkyl group having 1 to 10 carbon atoms may be, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, and 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 groups.

[0030] In this application, the halogen group may be, for example, fluorine, chlorine, bromine, or iodine.

[0031] In this application, specific examples of alkyl halogens include, but are not limited to, trifluoromethyl groups.

[0032] In this application, specific examples of deuterated alkyl groups include, but are not limited to, methyl trideuterated groups.

[0033] In this application, specific examples of trialkylsilyl groups include, but are not limited to, trimethylsilyl, ethyldimethylsilyl, and triethylsilyl groups.

[0034] In this application, a single bond extending from a ring system relating to a non-fixed position bond " "JPEG2026521481000007.jpg910" shows that one end of the bond can be connected to any position in the ring system through which the bond passes, and the other end can be connected to the rest of the compound molecule.

[0035] For example, as shown in formula (f) below, the naphthyl group represented by formula (f) is linked to other positions on the molecule via two position-free bonds that penetrate the double ring, meaning that any of the possible linkages represented by formulas (f-1) to (f-10) are included. JPEG2026521481000008.jpg22130 JPEG2026521481000009.jpg21126

[0036] To give another example, as shown in formula (X') below, the dibenzofuranyl group represented by formula (X') is linked to other positions on the molecule via position-free bonds extending from the middle of one benzene ring, meaning that any of the possible linkages represented by formulas (X'-1) to (X'-4) are included. JPEG2026521481000010.jpg18114

[0037] In this application, a non-positional substituent refers to a substituent connected by a single bond extending from the center of the ring system, indicating that the substituent may be connected at any possible position in the ring system. For example, as shown in formula (Y) below, the substituent R' represented by formula (Y) is connected to the quinoline ring via a single non-positional bond, which means that any of the possible connection methods represented by formulas (Y-1) to (Y-7) are included. JPEG2026521481000011.jpg4098

[0038] In some embodiments of this application, formula I is selected from structures represented by formula I-1, formula I-2, formula I-3, or formula I-4. JPEG2026521481000012.jpg37170

[0039] In some embodiments of this application, L, L1, and L2 are the same or different and each independently selected from single bonds, substituted or unsubstituted arylene groups having 6 to 18 carbon atoms, and substituted or unsubstituted heteroarylene groups having 5 to 18 carbon atoms. For example, L, L1, and L2 are the same or different and each independently selected from single bonds, substituted or unsubstituted arylene groups having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, or 18 carbon atoms, and substituted or unsubstituted heteroarylene groups having 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, or 18 carbon atoms.

[0040] In some embodiments of this application, the substituents in L, L1, and L2 are each independently selected from deuterium, fluorine, a cyano group, a C1-C5 alkyl group, a C3-C8 trialkylsilyl group, a C1-C5 halogenated alkyl group, a C1-C5 deuterated alkyl group, or a phenyl group.

[0041] In some embodiments of this application, L, L1 and L2 are the same or different and each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted dibenzothiophenylene group, a substituted or unsubstituted dibenzofuranylene group, and a substituted or unsubstituted carbazoylene group.

[0042] In some embodiments of this application, the substituents in L, L1 and L2 are the same or different and each is independently selected from deuterium, fluorine, cyano group, methyl group, ethyl group, isopropyl group, tert-butyl group, trifluoromethyl group, trideuterated methyl group, trimethylsilyl group, or phenyl group.

[0043] In some embodiments of this application, L, L1, and L2 are the same or different and each is independently selected from a single bond or the following groups. JPEG2026521481000013.jpg53148

[0044] In some embodiments of this application, L is selected from the group consisting of a single bond or the following groups. JPEG2026521481000014.jpg22170

[0045] In some embodiments of this application, L1 and L2 are the same or different, and each is independently selected from the group consisting of a single bond or the following groups. JPEG2026521481000015.jpg86170

[0046] In some embodiments of this application, Ar1 and Ar2 are each independently selected from substituted or unsubstituted aryl groups having 6 to 20 carbon atoms and substituted or unsubstituted heteroaryl groups having 12 to 18 carbon atoms. For example, Ar1 and Ar2 are each independently selected from substituted or unsubstituted aryl groups having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20 carbon atoms and substituted or unsubstituted heteroaryl groups having 12, 13, 14, 15, 16, 17, or 18 carbon atoms.

[0047] In some embodiments of this application, the substituents in Ar1 and Ar2 are independently selected from deuterium, a halogen group, a cyano group, a C1-C5 alkyl group, a C1-C5 halogenated alkyl group, a C1-C5 deuterated alkyl group, a C3-C8 trialkylsilyl group, a C6-C12 aryl group, or a C5-C12 heteroaryl group.

[0048] In some embodiments of this application, Ar1 and Ar2 are independently selected from a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, or a substituted or unsubstituted carbazolyl group.

[0049] In some embodiments of this application, the substituents in Ar1 and Ar2 are independently selected from deuterium, fluorine, cyano group, trideuterated methyl group, trimethylsilyl group, trifluoromethyl group, methyl group, ethyl group, isopropyl group, tert-butyl group, phenyl group, or naphthyl group.

[0050] In some embodiments of this application, Ar1 and Ar2 are the same or different and each is independently selected from the group consisting of the following groups. JPEG2026521481000016.jpg66170

[0051] In some embodiments of this application, Ar1 and Ar2 are the same or different and each is independently selected from the group consisting of the following groups. JPEG2026521481000017.jpg166169

[0052] In some embodiments of this application, JPEG2026521481000018.jpg621 and Each JPEG2026521481000019.jpg621 image is independently selected from the following group of elements. JPEG2026521481000020.jpg88170

[0053] In some embodiments of this application, JPEG2026521481000021.jpg721 and Each JPEG2026521481000022.jpg620 image is independently selected from the following group of elements. JPEG2026521481000023.jpg42170 JPEG2026521481000024.jpg160170

[0054] In some embodiments of this application, the organic compound of formula I is selected from the group consisting of the following compounds. JPEG2026521481000025.jpg58170 JPEG2026521481000026.jpg218165 JPEG2026521481000027.jpg215162 JPEG2026521481000028.jpg212163 JPEG2026521481000029.jpg197163 JPEG2026521481000030.jpg214170 JPEG2026521481000031.jpg225170 JPEG2026521481000032.jpg225170 JPEG2026521481000033.jpg202163 JPEG2026521481000034.jpg174162

[0055] In a second aspect, the application provides an organic electroluminescent device comprising an anode, a cathode, and a functional layer provided between the anode and the cathode, wherein the functional layer comprises the organic compound described in the first aspect of the application.

[0056] The compounds provided in this application can be used to form at least one organic film layer in a functional layer to improve properties such as current efficiency and lifetime of an organic electroluminescent device.

[0057] In some embodiments, the functional layer includes an organic light-emitting layer containing the organic compound. Here, 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 together.

[0058] According to one specific embodiment, the organic electroluminescent device may include an anode 100, a hole transport layer 321, an electron blocking layer 322, an organic light-emitting layer 330, an electron transport layer 340, and a cathode 200, which are arranged in a stacked manner as shown in Figure 1.

[0059] In this application, the anode 100 includes an anode material, preferably a material having a large work function that contributes to the injection of holes into the functional layer. Specific examples of anode materials include, but are not limited to, 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. Preferably, the anode includes a transparent electrode containing indium tin oxide (indium tin oxide) (ITO).

[0060] In this application, the hole transport layer may include one or more types of hole transport materials, and the hole transport layer material may be selected from carbazole polymers, carbazole-bound triarylamine compounds, or other types of compounds, and specifically from the compounds shown below or any combination thereof. JPEG2026521481000035.jpg133159

[0061] Those skilled in the art can select by reference to the prior art, and this application is not particularly limited thereto.

[0062] In one embodiment of this application, the hole transport layer 321 is HT-1.

[0063] In one embodiment of this application, the electronic blocking layer 322 is HT-2.

[0064] In some embodiments of this application, a hole injection layer 310 is further provided between the anode 100 and the hole transport layer 321 to improve the hole injection capability into the hole transport layer 321. The hole injection layer 310 can be selected from benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives, or other materials, and is not particularly limited in this application. The material of the hole injection layer 310 can be selected from, for example, the following compounds or any combination thereof. JPEG2026521481000036.jpg106164

[0065] In one embodiment of this application, the hole injection layer 310 is composed of PD and HT-1.

[0066] In this application, the organic light-emitting layer 330 may consist of a single light-emitting material, or it may include a host material and a guest material. Optionally, the organic light-emitting layer 330 may consist of a host material and a guest material, and holes injected into the organic light-emitting layer 330 and electrons injected into the organic light-emitting layer 330 recombine in the organic light-emitting layer 330 to form excitons. These excitons transfer energy to the host material, and the host material transfers energy to the guest material, thereby causing the guest material to emit light.

[0067] The host material of the organic light-emitting layer 330 may include metal chelate compounds, bistyryl derivatives, aromatic amine derivatives, dibenzofuran derivatives, or other types of materials.

[0068] In some embodiments of this application, the host material of the organic light-emitting layer 330 is the compound of this application and RH-P The filename is JPEG2026521481000037.jpg2442.

[0069] The guest material of the organic light-emitting layer 330 may be a compound or derivative thereof having a condensed aryl ring, a compound or derivative thereof having a heteroaryl ring, an aromatic amine derivative, or other material, and is not particularly limited in this application. The guest material is also called a dopant material or dopant. Depending on the type of light emission, it can be divided into fluorescent dopants and phosphorescent dopants. Specific examples of the phosphorescent dopants include, but are not limited to, the following. JPEG2026521481000038.jpg83169

[0070] In one embodiment of this application, the organic electroluminescent device is a red organic electroluminescent device. An example of a guest material is RD. The filename is JPEG2026521481000039.jpg2442.

[0071] The electron transport layer 340 may have a single-layer structure or a multilayer structure, and may contain one or more types of electron transport materials, the electron transport materials may be selected from BTB, LiQ, ET-1, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials, and are not particularly limited in this application. The material of the electron transport layer 340 may contain, but is not limited to, the following compounds. JPEG2026521481000040.jpg103165

[0072] In one embodiment of this application, the electron transport layer 340 may be composed of ET-1 and LiQ.

[0073] In this application, the cathode 200 may include a cathode material which is a material having a small work function that contributes to 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. Optionally, a metallic electrode containing magnesium and silver may be included as the cathode.

[0074] In some embodiments, an additional electron injection layer 350 is provided between the cathode 200 and the electron transport layer 340 to enhance the electron injection capability into the electron transport layer 340. The electron injection layer 350 may contain inorganic materials such as alkali metal sulfides and alkali metal halides, or it may contain complexes of alkali metals and organic substances. In one embodiment of this application, the electron injection layer 350 may contain LiQ.

[0075] In a third aspect, the present application provides an electronic device including an organic electroluminescent device as described in a second aspect of the present application.

[0076] According to one embodiment, as shown in Figure 2, the provided electronic device is an electronic device 400 including the organic electroluminescent device. The electronic device 400 may be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices, and may include, but is not limited to, computer screens, mobile phone screens, televisions, electronic paper, emergency lighting, optical modules, etc.

[0077] The following describes in detail the synthesis method of the compounds of this application in accordance with the synthesis examples, but this disclosure is not limited thereto. Synthesis Examples

[0078] 1. Synthesis of intermediate Sub-a1: Under a nitrogen atmosphere, 19.70 g, 70 mmol of 3-bromo-1-chlorodibenzo[B,D]furan and 200 mL of dried tetrahydrofuran were added to a 500 mL three-necked flask. The system was cooled to -78°C, and n-butyllithium solution (2.0 M n-hexane solution, 38.5 mL, 77 mmol) was added dropwise. After the addition was complete, the temperature was maintained (-78°C) and the mixture was stirred for 1 hour. The reaction system was maintained at -78°C, and trimethyl borate (10.91 g, 105 mmol) was added dropwise. After the addition was complete, the mixture was kept warm for 1 hour (-78°C). Then, the reaction system was allowed to rise naturally to room temperature. Dilute hydrochloric acid (2 M, 58 mL) was added dropwise to the reaction mixture, and the mixture was stirred for 30 minutes. The mixture was extracted with dichloromethane (100 mL x 3 times), the organic phases were combined and dried over anhydrous magnesium sulfate, filtered, and then the solvent was removed by vacuum distillation to obtain the crude product. The crude product was beaten with n-heptane and filtered to obtain the intermediate Sub-a1 (11.56 g, yield 67%), which was a white solid. Sub-a4 was synthesized from intermediate Sub-a2, listed in Table 1, using the same method as for intermediate Sub-a1, except that reactant A was used instead of 3-bromo-1-chlorodibenzo[B,D]furan. The main starting materials used, the synthesized intermediates, and their yields are shown in Table 1. JPEG2026521481000042.jpg94122

[0079] 2. Synthesis of intermediate Sub-b1: Under a nitrogen atmosphere, o-bromobenzaldehyde (9.25 g, 50 mmol), intermediate Sub-a1 (13.55 g, 55 mmol), tetrakis(triphenylphosphine)palladium (0.58 g, 0.5 mmol), anhydrous sodium carbonate (10.60 g, 100 mmol), toluene (140 mL), anhydrous ethanol (35 mL), and deionized water (35 mL) were sequentially added to a 500 mL three-necked flask. Stirring and heating were started, and the temperature was raised to reflux for 8 hours. After the reaction system was cooled to room temperature, it was extracted with dichloromethane (100 mL x 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 obtain the white solid intermediate Sub-b1 (11.20 g, 73% yield). Sub-b4 was synthesized from intermediate Sub-b2, as listed in Table 2, using the same method as for intermediate Sub-b1, except that reactant B was used instead of intermediate Sub-a1. The main starting materials used, the synthesized intermediates, and their yields are shown in Table 2. JPEG2026521481000044.jpg91108

[0080] 3. Synthesis of intermediate Sub-c1: Under a nitrogen atmosphere, (methoxymethyl)triphenylphosphonium chloride (51.25 g, 149.5 mmol) and anhydrous tetrahydrofuran (200 mL) were added to a 1000 mL three-necked flask, and the system was cooled to -15°C and held for 30 mins. Then, Sub-b1 (39.90 g, 130 mmol) was weighed and dissolved in anhydrous tetrahydrofuran (200 mL), and the solution was slowly added dropwise to the reaction system using an isobaric dropping funnel. The temperature was maintained at -15°C during the addition, and after the addition was complete, the temperature was maintained at -15°C and the reaction was stirred for 1 hour. Then, the reaction system was allowed to rise naturally to room temperature, extracted with dichloromethane (200 mL x 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 n-heptane / dichloromethane as the mobile phase to obtain the red solid intermediate Sub-c1 (29.60 g, 68% yield). Sub-c4 was synthesized from intermediate Sub-c2, as listed in Table 3, using the same method as for intermediate Sub-c1, except that reactant C was used instead of intermediate Sub-c1. The main starting materials used, the synthesized intermediates, and their yields are shown in Table 3. JPEG2026521481000046.jpg86105

[0081] 4. Synthesis of intermediate Sub-d1: Under a nitrogen atmosphere, Sub-c1 (39.84 g, 119 mmol), Eaton's reagent (4.5 mL), and chlorobenzene (500 mL) were sequentially added to a 1000 mL three-necked flask, and the mixture was heated to reflux and stirred for 4 hours. After the reaction system was cooled to room temperature, the reaction mixture was poured into 1000 mL of deionized water, neutralized with saturated sodium hydroxide solution, and then extracted with dichloromethane (250 mL x 3 times). The organic phases were combined and dried over anhydrous magnesium sulfate, filtered, and then the solvent was removed by vacuum distillation to obtain the crude product. The crude product was purified by silica gel column chromatography with dichloromethane / n-heptane as the mobile phase to obtain Sub-d1 (17.29 g, yield 48%), a white solid. Sub-d4 was synthesized from intermediate Sub-d2, as listed in Table 4, using the same method as for intermediate Sub-d1, except that reactant D was used instead of intermediate Sub-d1. The main raw materials used, the synthesized intermediates, and their yields are shown in Table 4. JPEG2026521481000048.jpg89111

[0082] 5. Synthesis of intermediate Sub-e1: Under a nitrogen atmosphere, Sub-d1 (15.14 g, 50 mmol), bis(pinacolato)divoton (14.0 g, 55 mmol), potassium acetate (10.8 g, 110 mmol), and 1,4-dioxane (160 mL) were sequentially added to a 500 mL three-necked flask. Stirring and heating were started, and the system was raised to 40 °C. 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 rapidly added, and the temperature was continued to rise until reflux was achieved, and the mixture was stirred overnight. After cooling the reaction system to room temperature, 200 mL of water was added to the system, and the mixture was stirred thoroughly for 30 minutes. The mixture was then filtered under reduced pressure and suction. The filter cake was washed with deionized water to neutralize it, and then washed again with 100 mL of anhydrous ethanol to obtain a gray solid. The crude product was beaten once with n-heptane, and then dissolved in 200 mL of toluene to form a clear solution. This solution was then passed through a silica gel column to remove the catalyst, and after concentration, a white solid intermediate, Sub-e1 (13.21 g, yield 67%), was obtained. Sub-e4 was synthesized from intermediate Sub-e2, as listed in Table 5, using the same method as for intermediate Sub-e1, except that reactant E was used instead of intermediate Sub-d1. The main starting materials used, the synthesized intermediates, and their yields are shown in Table 5. JPEG2026521481000050.jpg97106

[0083] 6. Synthesis of intermediate Sub-f1: Under a nitrogen atmosphere, 2-chloro-4-(1-naphthyl)-6-phenyl-1,3,5-triazine (15.94 g, 50 mmol), 3-chlorophenylboronic acid (8.60 g, 55 mmol), tetrakis(triphenylphosphine)palladium (0.58 g, 0.5 mmol), anhydrous sodium carbonate (10.60 g, 100 mmol), toluene (180 mL), anhydrous ethanol (45 mL), and deionized water (45 mL) were sequentially added to a 500 mL three-necked flask. Stirring and heating were started, and the temperature was increased until reflux was achieved, and the reaction was carried out for 8 hours. After the system was cooled to room temperature, it was extracted with dichloromethane (100 mL x 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 obtain a white solid (15.36 g, 78% yield). Sub-f10 was synthesized from intermediate Sub-f2, listed in Table 6, in the same manner as intermediate Sub-f1, except that reactant F was used instead of 2-chloro-4-(1-naphthyl)-6-phenyl-1,3,5-triazine and reactant G was used instead of 3-chlorophenylboronic acid. The main starting materials used, the synthesized intermediates, and their yields are shown in Table 6. JPEG2026521481000052.jpg251130

[0084] Synthesis Example 1: Synthesis of Compound 3 Under a nitrogen atmosphere, Sub-e1 (10.35 g, 26.25 mmol), 2-chloro-4-(2-naphthyl)-6-phenyl-1,3,5-triazine (7.94 g, 25 mmol), palladium acetate (42 mg, 0.25 mmol), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (XPhos, 0.24 g, 0.5 mmol), anhydrous potassium carbonate (6.9 g, 50 mmol), tetrabutylammonium bromide (0.8 g, 2.5 mmol), toluene (100 mL), tetrahydrofuran (25 mL), and deionized water (25 mL) were sequentially added to a 250 mL three-necked flask. Stirring and heating were started, and the temperature was raised to reflux for 16 hours. After cooling the system to room temperature, it was extracted with dichloromethane (100 mL x 3 times), the organic phases were combined and dried over anhydrous magnesium sulfate, filtered, and then 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 compound 3 (9.20 g, yield 67%), a yellowish-green solid, with a mass spectrum (m / z) of 550.19 [M+H]. + That was the case. The compounds listed in Table 7 were synthesized in the same manner as compound 3, except that reactant H was used instead of Sub-e1, and reactant J was used instead of 2-chloro-4-(2-naphthyl)-6-phenyl--1,3,5-triazine. The main starting materials used, the synthesized compounds, their mass spectra, and yields are shown in Table 7. JPEG2026521481000054.jpg246113 JPEG2026521481000055.jpg220163 JPEG2026521481000056.jpg220164 JPEG2026521481000057.jpg226164 JPEG2026521481000058.jpg219164 JPEG2026521481000059.jpg206168 JPEG2026521481000060.jpg220166 JPEG2026521481000061.jpg227165 JPEG2026521481000062.jpg217167 JPEG2026521481000063.jpg145165

[0085] Nuclear magnetic data for some compounds: Nuclear magnetism of compound 9: 1 H-NMR (400MHz, Methylene-Chloride-D2) δ ppm 9.41(s, 1H), 8.85(d, 2H), 8.79(d, 1H), 8.62(d, 1H), 8.35(d, 1H), 8.26(d, 1H), 8.17-8.09(m, 2H), 7.93(d, 1H), 7.75-7.45(m, 13H). Nuclear magnetism of compound 177: 1 H-NMR (400MHz, Methylene-Chloride-D2) δ ppm 9.54(s, 1H), 8.82(d, 2H), 8.71(d, 1H), 8.60(d, 1H), 8.33-8.24(m, 3H), 8.01-7.85(m, 5H), 7.80-7.69(m, 3H), 7.68-7.31(m, 11H).

[0086] Examples of Fabrication and Evaluation of Organic Electroluminescent Devices Example 1: Fabrication of a red organic electroluminescent device The following process was used for anodic pretreatment. ITO / Ag / ITO substrates with thicknesses of 100 Å, 1000 Å, and 100 Å were cut to a size of 40 mm (length) × 40 mm (width) × 0.7 mm (thickness). Experimental substrates with anode and insulating layer patterns were fabricated using a photolithography process, and the surface treatment was performed using ultraviolet ozone and O2:N2 plasma to increase the work function of the substrate anode. A hole injection layer with a thickness of 100 Å was formed by co-depositing PD:HT-1 onto an experimental substrate (anode) at a deposition rate of 2%:98%. A hole transport layer with a thickness of 1060 Å was formed by vacuum deposition of compound HT-1 onto a hole injection layer. The compound HT2 was vacuum-deposited onto a hole transport layer to form an electron blocking layer with a thickness of 880 Å. A 400 Å thick organic luminescent layer was formed by co-depositing compound 3:RH-P:RD on an electron block layer at a deposition rate of 49%:49%:2%. On an organic light-emitting layer, compound ET-1 and LiQ were co-deposited at a 1:1 deposition rate to form an electron transport layer with a thickness of 350 Å. Then, Yb was deposited on the electron transport layer to form an electron injection layer with a thickness of 10 Å. Finally, magnesium (Mg) and silver (Ag) were deposited on the electron injection layer at a 1:9 deposition rate to form a cathode with a thickness of 130 Å. Finally, compound CP-1 was deposited onto the cathode to form an organic coating layer with a thickness of 800 Å, completing the fabrication of the red organic electroluminescent device.

[0087] Examples 2-75 An organic electroluminescent device was fabricated in the same manner as in Example 1, except that the compound shown in Table 8 was used instead of compound 3 in Example 1 when forming the organic light-emitting layer.

[0088] Comparative Examples 1-3 An organic electroluminescent device was fabricated in the same manner as in Example 1, except that compounds A, B, and C were used instead of compound 3 in Example 1 when forming the organic light-emitting layer.

[0089] The main material structures used in the above examples and comparative examples are shown below. JPEG2026521481000064.jpg116157

[0090] Performance tests were conducted on the red organic electroluminescent devices manufactured in Examples 1-75 and Comparative Examples 1-3, specifically, at 10 mA / cm². 2 The IVL performance of the device was tested under the following conditions, 95 Device lifespan 20mA / cm 2 The tests were conducted under these conditions, and the test results are shown in Table 8.

[0091] JPEG2026521481000065.jpg245157 JPEG2026521481000066.jpg192170

[0092] Referring to Table 8 above, when the compound of the present invention was used as a host material for a red organic electroluminescent device, the current efficiency was improved by at least 10.2% and the lifetime was improved by at least 12.3% compared to Comparative Examples 1-3.

[0093] A person skilled in the art will readily conceive of other embodiments of this application after considering the specification and implementing the invention disclosed herein. This application is intended to cover any variations, uses, or adaptive changes of this application, which will follow the general principles of this application and include common or conventional technical means in the art not disclosed herein. [Explanation of symbols]

[0094] 100 Anode, 200 Cathode, 300 Functional layer, 310 Hole injection layer, 321 Hole transport layer, 322 Electron blocking layer, 330 Organic light-emitting layer, 340 Electron transport layer, 350 Electron injection layer, 400 Electronic device

Claims

1. An organic compound having the structure shown in Formula 1, Equation I However, X and Y are selected from single bonds, O, or S, and one of X and Y is selected from O or S, and the other is a single bond. L, L 1 and L 2 These are the same or different, and each is independently selected from single bonds, substituted or unsubstituted arylene groups having 6 to 30 carbon atoms, and substituted or unsubstituted heteroarylene groups having 3 to 30 carbon atoms. Ar 1 and Ar 2 These are the same or different, and each is independently selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms. L, L 1 , L 2 Ar 1 and Ar 2 The substituents in are the same or different and are independently selected from deuterium, a cyano group, a halogen group, a C1-C10 alkyl group, a C1-C10 halogenated alkyl group, a C1-C10 deuterated alkyl group, a C3-C12 trialkylsilyl group, a C6-C20 aryl group, or a C3-C20 heteroaryl group.

2. The organic compound according to claim 1, wherein formula I is selected from the structures represented by formula I-1, formula I-2, formula I-3, or formula I-4.

3. L, L 1 and L 2 are the same or different and each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 18 carbon atoms, and a substituted or unsubstituted heteroarylene group having 5 to 18 carbon atoms, Available in sizes L and L 1 and L 2 The organic compound according to claim 1, wherein each substituent is independently selected from deuterium, fluorine, a cyano group, a C1-C5 alkyl group, a C3-C8 trialkylsilyl group, a C1-C5 halogenated alkyl group, a C1-C5 deuterated alkyl group, or a phenyl group.

4. L, L 1 and L 2 These are the same or different, and each is independently selected from single bonds, substituted or unsubstituted phenylene groups, substituted or unsubstituted naphthylene groups, substituted or unsubstituted biphenylene groups, substituted or unsubstituted dibenzothiophenylene groups, substituted or unsubstituted dibenzofuranylene groups, and substituted or unsubstituted carbasolylene groups. Available in sizes L and L 1 and L 2 The organic compound according to claim 1, wherein the substituents in are the same or different and each is independently selected from deuterium, fluorine, cyano group, methyl group, ethyl group, isopropyl group, tert-butyl group, trifluoromethyl group, trideuterated methyl group, trimethylsilyl group, or phenyl group.

5. L, L 1 and L 2 The organic compound according to claim 1, wherein the groups are the same or different, and each is independently selected from a single bond or the following groups.

6. Ar 1 and Ar 2 Each of these is independently selected from substituted or unsubstituted aryl groups having 6 to 20 carbon atoms and substituted or unsubstituted heteroaryl groups having 12 to 18 carbon atoms. Selectable, Ar 1 and Ar 2 The organic compound according to claim 1, wherein each substituent is independently selected from deuterium, a halogen group, a cyano group, a C1-C5 alkyl group, a C1-C5 halogenated alkyl group, a C1-C5 deuterated alkyl group, a C3-C8 trialkylsilyl group, a C6-C12 aryl group, or a C5-C12 heteroaryl group.

7. Ar 1 and Ar 2 Each of these groups is independently selected from substituted or unsubstituted phenyl groups, substituted or unsubstituted naphthyl groups, substituted or unsubstituted biphenyl groups, substituted or unsubstituted terphenyl groups, substituted or unsubstituted phenanthryl groups, substituted or unsubstituted triphenylenyl groups, substituted or unsubstituted fluorenyl groups, substituted or unsubstituted spirobifluorenyl groups, substituted or unsubstituted dibenzofuranyl groups, substituted or unsubstituted dibenzothienyl groups, and substituted or unsubstituted carbazolyl groups. Selectable, Ar 1 and Ar 2 The organic compound according to claim 1, wherein each substituent is independently selected from deuterium, fluorine, cyano group, trideuterated methyl group, trimethylsilyl group, trifluoromethyl group, methyl group, ethyl group, isopropyl group, tert-butyl group, phenyl group, or naphthyl group.

8. Ar 1 and Ar 2 The organic compound according to claim 1, wherein the group is the same or different and each is independently selected from the group consisting of the following groups.

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

10. The aforementioned compound is an organic compound according to claim 1, selected from the following structures.

11. An organic electroluminescent device comprising an anode and a cathode arranged opposite each other, and a functional layer provided between the anode and the cathode, The functional layer comprises the organic compound described in any one of claims 1 to 10. Selectively, the functional layer includes an organic light-emitting layer, and the organic light-emitting layer includes the organic compound. Preferably, the organic electroluminescent device is a red organic electroluminescent device, characterized in that the organic electroluminescent device is a red organic electroluminescent device.

12. An electronic device characterized by comprising the organic electroluminescent device described in claim 11.

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