Organic compound and organic electroluminescent device comprising same, and electronic device

Abstract

The present application relates to the technical field of organic electroluminescent materials, and provides an organic compound, an organic electroluminescent device and an electronic device. The organic compound of the present application has a structure as represented by formula I, and can significantly improve the performance of a device.

Description

Organic compound and organic electroluminescent device and electronic device containing the same

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims priority to the Chinese patent application with application number CN202410373346.X filed on March 28, 2024. The full text of the above-mentioned Chinese patent application is hereby cited as part of this application. Technical Field

[0003] The present application relates to the technical field of organic electroluminescent materials, and in particular to an organic compound and an organic electroluminescent device and an electronic apparatus containing the same. Background Art

[0004] Nowadays, with the rapid development of organic synthesis and materials science, organic electroluminescent device (OLED) display technology has been applied in fields such as smartphones and tablets, and will further expand to large-size application fields such as televisions. The optoelectronic functional materials used in OLED devices can be divided into charge injection transport materials and luminescent materials based on their uses; according to the functions of each layer of materials, charge injection transport materials can also be divided into electron injection transport materials, electron blocking materials, hole injection transport materials and hole blocking materials. Therefore, the optoelectronic functional material film layer that constitutes the OLED device includes at least two or more layers. The structure of OLED devices used in the industry includes a variety of film layers such as hole injection layer, hole transport layer, electron blocking layer, organic light-emitting layer, hole blocking layer, electron transport layer, electron injection layer, etc., and the material types and matching forms are rich and diverse. In addition, for the matching of OLED devices with different structures, the optoelectronic functional materials used have strong selectivity, and the performance of the same material in devices with different structures may also be completely different.

[0005] Generally speaking, the choice of host material is crucial in a host / dopant system, as it significantly impacts the efficiency and lifetime of a light-emitting device. High-performance host materials should possess an appropriate molecular weight, a 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, they must exhibit excellent carrier transport capabilities and possess appropriate triplet energy levels to ensure efficient energy transfer from the host material to the guest material during light emission, thereby achieving high device efficiency.

[0006] The main challenges facing existing organic electroluminescent devices are lifespan and efficiency. As displays become larger, driving voltages increase, and luminous efficiency and current efficiency also need to be improved. Therefore, it is necessary to continue researching and developing new materials to further enhance the performance of organic electroluminescent devices. Summary of the Invention

[0007] In view of the above problems existing in the prior art, the purpose of this application is to provide an organic compound and an organic electroluminescent device and an electronic device containing the same. The organic compound can be used in an organic electroluminescent device to improve the performance of the device.

[0008] The first aspect of the present application provides an organic compound having a structure shown in Formula 1:

[0009] wherein X and Y are selected from a single bond, O or S, and one of X and Y is selected from O or S, and the other is a single bond;

[0010] L, L1 and L2 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;

[0011] Ar1 and Ar2 are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;

[0012] The substituents in L, L1, L2, Ar1 and Ar2 are the same or different and are each independently selected from deuterium, cyano, a halogen group, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 3 to 20 carbon atoms.

[0013] A second aspect of the present application provides an organic electroluminescent device, comprising an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer comprises the above-mentioned organic compound.

[0014] A third aspect of the present application provides an electronic device comprising the organic electroluminescent device described in the second aspect.

[0015] The compounds of this application are phenanthrenyl Based on, benzofuran or benzothiophene are fused at positions 1 and 2 to form a mother core structure, and an electron-deficient heteroaryl of a triazine is connected at position 3, which can be used as an electron-transporting red light host material. First, the mother core of the phenanthrenyl group fused at positions 1 and 2 to benzofuran or benzothiophene has a more suitable first excited triplet energy level, which is suitable as a fragment of the light-emitting host material; secondly, the larger conjugated area of ​​the mother core and the presence of lone pairs of electrons on the oxygen atom or sulfur atom in the mother core can significantly enhance the carrier transport performance of the target compound; thirdly, the electron-deficient heteroaryl of the triazine connected at position 3 and the presence of lone pairs of electrons on its adjacent hydrogen atoms and oxygen / sulfur atoms make the molecule more twisted, which can give the compound of the present application better film-forming properties. Therefore, when the compound of the present application is used as an electron-transporting host material in a mixed red light host material, it can improve the carrier balance in the light-emitting layer, broaden the carrier recombination area, and improve the exciton generation and utilization efficiency, thereby improving the luminous efficiency and life of the device. BRIEF DESCRIPTION OF THE DRAWINGS

[0016] The accompanying drawings are used to provide further understanding of the present application and constitute a part of the specification. Together with the following specific embodiments, they are used to explain the present application, but do not constitute a limitation to the present application.

[0017] FIG1 is a schematic structural diagram of an organic electroluminescent device according to an embodiment of the present application.

[0018] FIG2 is a schematic structural diagram of an electronic device according to an embodiment of the present application.

[0019] Reference numerals 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 DETAILED DESCRIPTION

[0020] The exemplary embodiments will now be described more fully with reference to the accompanying drawings. However, the exemplary embodiments can be implemented in various 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 concepts of the 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 provide a full understanding of the embodiments of the present application.

[0021] In a first aspect, the present application provides a compound having a structure shown in Formula I:

[0022] wherein X and Y are selected from a single bond, O or S, and one of X and Y is selected from O or S, and the other is a single bond;

[0023] L, L1 and L2 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;

[0024] Ar1 and Ar2 are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;

[0025] The substituents in L, L1, L2, Ar1 and Ar2 are the same or different and are each independently selected from deuterium, cyano, a halogen group, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 3 to 20 carbon atoms.

[0026] In the present application, X and Y are selected from a single bond, 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; when Y is S, X is a single bond.

[0027] In this application, the descriptions used are “each independently”, “each independently” and “each independently” and should be understood in a broad sense. They can mean that in different groups, the specific options expressed by the same symbols do not affect each other, or in the same group, the specific options expressed by the same symbols do not affect each other. For example, Wherein, each q is independently 0, 1, 2 or 3, and each R" is independently selected from hydrogen, deuterium, fluorine, and chlorine. The meaning is: Formula Q-1 represents that there are q substituents R" on the benzene ring, and each R" can be the same or different, and the options of each R" do not affect each other; Formula Q-2 represents that there are q substituents R" on each benzene ring of biphenyl, and the number q of R" substituents on the two benzene rings can be the same or different, and each R" can be the same or different, and the options of each R" do not affect each other.

[0028] In the present application, the term "substituted or unsubstituted" means that the functional group recorded after the term may or may not have a substituent (hereinafter, for the sake of convenience of description, the substituents will be 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 above-mentioned substituent, i.e., Rc, can be, for example, deuterium, a halogen group, a cyano group, an alkyl group, a cycloalkyl group, an aryl group, a heteroaryl group, a deuterated aryl group, a halogenated aryl group, a trialkylsilyl group, a halogenated alkyl group or a deuterated alkyl group. The number of substituents Rc can be one or more. When two substituents Rc are connected to the same atom, the two substituents Rc can exist independently or be connected to each other to form a ring with the atom; when there are two adjacent substituents Rc on the functional group, the adjacent substituents Rc can exist independently or be fused to form a ring with the functional group to which they are connected.

[0029] In the present application, "plurality" means two or more, for example, 2, 3, 4, 5, 6, etc.

[0030] The hydrogen atoms in the structures of the compounds of the present application include various isotope atoms of the hydrogen element, such as hydrogen (H), deuterium (D) or tritium (T).

[0031] In this application, the number of carbon atoms in a substituted or unsubstituted functional group refers to the total number of carbon atoms. For example, if L1 is a substituted arylene group with 12 carbon atoms, the total number of carbon atoms in the arylene group and its substituents is 12.

[0032] In the present application, aryl refers to an optional functional group or substituent derived from an aromatic carbocyclic ring. Aryl can be a monocyclic aryl (such as phenyl) or a polycyclic aryl. In other words, aryl can be a monocyclic aryl, a condensed ring aryl, two or more monocyclic aryl groups connected by carbon-carbon bond conjugation, a monocyclic aryl and a condensed ring aryl connected by carbon-carbon bond conjugation, two or more condensed ring aryl groups connected by carbon-carbon bond conjugation. That is, unless otherwise indicated, two or more aromatic groups connected by carbon-carbon bond conjugation can also be considered as aryl of the present application. Wherein, condensed ring aryl, for example, can include bicyclic condensed aryl (such as naphthyl), tricyclic condensed aryl (such as phenanthrenyl, fluorenyl, anthracenyl) etc. Aryl does not contain heteroatoms such as B, N, O, S, P, Se and Si. Examples of aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, spirobifluorenyl, anthracenyl, phenanthrenyl, biphenyl, terphenyl, triphenylene, peryl, benzo[9,10]phenanthrenyl, pyrenyl, benzofluoranthenyl, Ji et al.

[0033] In the present application, the arylene group refers to a divalent group formed by further losing one or more hydrogen atoms from an aryl group.

[0034] In the present application, a substituted aryl group may be an aryl group in which one or more hydrogen atoms are replaced by groups such as a deuterium atom, a halogen group, a cyano group, an aryl group, a heteroaryl group, a trialkylsilyl group, an alkyl group, a cycloalkyl group, a haloalkyl group, a deuterated alkyl group, a haloaryl group, a deuterated aryl group, etc. It should be understood that the number of carbon atoms in a 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 having 18 carbon atoms means that the total number of carbon atoms in the aryl group and the substituents is 18.

[0035] In the present application, the fluorenyl group may be substituted by one or more substituents. In the case where the fluorenyl group is substituted, the substituted fluorenyl group may be: etc., but not limited thereto.

[0036] In the present 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, wherein the heteroatoms may be one or more of B, O, N, P, Si, Se and S. A heteroaryl group may be a monocyclic heteroaryl group or a polycyclic heteroaryl group. In other words, a heteroaryl group may be a single aromatic ring system or a plurality of aromatic ring systems connected by conjugated carbon-carbon bonds, and any aromatic ring system may be a single aromatic ring or a condensed aromatic ring. For example, the heteroaryl group may include a thienyl group, a furyl group, a pyrrolyl group, an imidazolyl group, a thiazolyl group, an oxazolyl group, an oxadiazolyl group, a triazolyl group, a pyridyl group, a bipyridyl group, a pyrimidyl group, a triazinyl group, an acridinyl group, a pyridazinyl group, a pyrazinyl group, a quinolyl group, a quinazolinyl group, a quinoxalinyl group, a phenoxazinyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyrazinyl group, a pyrazinopyrazinyl group, an isoquinolyl group, an indolyl group, a carbazolyl group, a benzoxazolyl group, a benzimidazolyl group, a benzothiazolyl group, a benzocarbazolyl group, a benzothienyl group, a dibenzothienyl group, a thienothiphenyl 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, and the like, without being limited thereto. Among them, thienyl, furyl, phenanthroline, etc. are heteroaryl groups of a single aromatic ring system type, and N-phenylcarbazolyl and N-pyridylcarbazolyl are heteroaryl groups of a polycyclic system type connected by conjugation through carbon-carbon bonds.

[0037] In the present application, the heteroarylene group refers to a divalent group formed by further losing one or more hydrogen atoms from a heteroaryl group.

[0038] In the present application, a substituted heteroaryl group may be a heteroaryl group in which one or more hydrogen atoms are replaced by a group such as a deuterium atom, a halogen group, a cyano group, an aryl group, a heteroaryl group, a trialkylsilyl group, an alkyl group, a haloalkyl group, a deuterated alkyl group, a haloaryl group, a deuterated aryl group, etc. Specific examples of aryl-substituted heteroaryl groups include, but are not limited to, a phenyl-substituted dibenzofuranyl group, a phenyl-substituted dibenzothienyl group, a phenyl-substituted pyridyl group, etc. It should be understood that the number of carbon atoms in a substituted heteroaryl group refers to the total number of carbon atoms in the heteroaryl group and the substituents on the heteroaryl group.

[0039] In the present application, the number of carbon atoms of 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, 20. Specific examples of the aryl group as a substituent include, but are not limited to, phenyl, biphenyl, naphthyl, anthracenyl, base.

[0040] In the present application, the number of carbon atoms of the heteroaryl group as a substituent can be 3 to 20, for example, the number of carbon atoms can be 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20. Specific examples of the heteroaryl group as a substituent include, but are not limited to, pyridyl, pyrimidinyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, quinolyl, quinazolinyl, quinoxalinyl, and isoquinolyl.

[0041] In the present application, the number of carbon atoms in the alkyl group with a carbon number of 1 to 10 can be, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10. Specific examples of the alkyl group include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, and n-hexyl.

[0042] In the present application, the halogen group may be, for example, fluorine, chlorine, bromine, or iodine.

[0043] In the present application, specific examples of the haloalkyl group include, but are not limited to, trifluoromethyl.

[0044] In the present application, specific examples of deuterated alkyl groups include, but are not limited to, trideuterated methyl groups.

[0045] In the present application, specific examples of the trialkylsilyl group include, but are not limited to, trimethylsilyl, ethyldimethylsilyl, triethylsilyl, and the like.

[0046] In this application, no single bond extending from the ring system is indicated by a linking bond. It means that one end of the connecting bond can be connected to any position in the ring system that the bond passes through, and the other end is connected to the rest of the compound molecule.

[0047] For example, as shown in the following formula (f), the naphthyl group represented by formula (f) is connected to other positions of the molecule through two non-positional connecting bonds that pass through the bicyclic ring, and its meaning includes any possible connection method shown in formulas (f-1) to (f-10).

[0048] For another example, as shown in the following formula (X'), the dibenzofuranyl group represented by formula (X') is connected to other positions of the molecule through a non-positional connecting bond extending from the middle of one side of the benzene ring, and its meaning includes any possible connection method shown in formulas (X'-1) to (X'-4).

[0049] A non-positional substituent as used herein refers to a substituent connected via a single bond extending from the center of the ring system, indicating that the substituent can be attached at any possible position within 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 non-positional bond, and its meaning includes any possible connection method shown in Formulas (Y-1) to (Y-7).

[0050] In some embodiments of the present application, Formula I is selected from the structure shown in Formula I-1, Formula I-2, Formula I-3 or Formula I-4:

[0051] In some embodiments of the present application, L, L1 and L2 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 18 carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 18 carbon atoms. For example, L, L1 and L2 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17 or 18 carbon atoms, or a substituted or unsubstituted heteroarylene group having 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17 or 18 carbon atoms.

[0052] In some embodiments of the present application, the substituents in L, L1 and L2 are each independently selected from deuterium, fluorine, cyano, an alkyl group having 1 to 5 carbon atoms, a trialkylsilyl group having 3 to 8 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, a deuterated alkyl group having 1 to 5 carbon atoms or a phenyl group.

[0053] In some embodiments of the present application, L, L1 and L2 are the same or different and are 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 dibenzofuranyl group, or a substituted or unsubstituted carbazolyl group.

[0054] In some embodiments of the present application, the substituents in L, L1 and L2 are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl or phenyl.

[0055] In some embodiments of the present application, L, L1 and L2 are the same or different and are each independently selected from a single bond or the following groups:

[0056] In some embodiments of the present application, L is selected from a single bond or the group consisting of the following groups:

[0057] In some embodiments of the present application, L1 and L2 are the same or different, and are each independently selected from the group consisting of a single bond or the following groups:

[0058] In some embodiments of the present application, Ar1 and Ar2 are each independently selected from a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroaryl group having 12 to 18 carbon atoms. For example, Ar1 and Ar2 are each independently selected from a substituted or unsubstituted aryl group having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20 carbon atoms, or a substituted or unsubstituted heteroaryl group having 12, 13, 14, 15, 16, 17 or 18 carbon atoms.

[0059] In some embodiments of the present application, the substituents in Ar1 and Ar2 are each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, a deuterated alkyl group having 1 to 5 carbon atoms, a trialkylsilyl group having 3 to 8 carbon atoms, an aryl group having 6 to 12 carbon atoms, or a heteroaryl group having 5 to 12 carbon atoms.

[0060] In some embodiments of the present application, Ar1 and Ar2 are each 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 phenanthrenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group.

[0061] In some embodiments of the present application, the substituents in Ar1 and Ar2 are each independently selected from deuterium, fluorine, cyano, trideuteromethyl, trimethylsilyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, phenyl or naphthyl.

[0062] In some embodiments of the present application, Ar1 and Ar2 are the same or different and are each independently selected from the group consisting of the following groups:

[0063] In some embodiments of the present application, Ar1 and Ar2 are the same or different and are each independently selected from the group consisting of the following groups:

[0064] In some embodiments of the present application, and Each is independently selected from the group consisting of:

[0065] In some embodiments of the present application, and Each is independently selected from the group consisting of:

[0066] In some embodiments of the present application, the organic compound of formula I is selected from the group consisting of the compounds shown below:

[0067] In a second aspect, the present application provides an organic electroluminescent device comprising an anode, a cathode, and a functional layer disposed between the anode and the cathode; wherein the functional layer comprises the organic compound described in the first aspect of the present application.

[0068] The compound provided in the present application can be used to form at least one organic film layer in a functional layer to improve the current efficiency, lifespan and other characteristics of an organic electroluminescent device.

[0069] In some embodiments, the functional layer includes an organic light-emitting layer, and the organic light-emitting layer includes the organic compound. The organic light-emitting layer can be composed of the organic compound provided in this application, or can be composed of the organic compound provided in this application and other materials.

[0070] According to a specific embodiment, the organic electroluminescent device is shown in FIG1 , and 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 stacked in sequence.

[0071] In the present 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. Preferably, a transparent electrode comprising indium tin oxide (ITO) as the anode is included.

[0072] In the present 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, and may specifically be selected from the following compounds or any combination thereof:

[0073] Those skilled in the art may make their selections by referring to the existing technologies, and this application does not impose any special limitation on this.

[0074] In one embodiment of the present application, the hole transport layer 321 is HT-1.

[0075] In one embodiment of the present application, the electron blocking layer 322 is HT-2.

[0076] In some embodiments of the present application, a hole injection layer 310 is further provided 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 made of a benzidine derivative, a starburst arylamine compound, a phthalocyanine derivative, or other materials, and this application does not impose any particular limitation thereto. The material of the hole injection layer 310 may be selected from the following compounds or any combination thereof, for example:

[0077] In one embodiment of the present application, the hole injection layer 310 is composed of PD and HT-1.

[0078] In the present application, the organic light-emitting layer 330 may be composed of a single light-emitting material or may include a host material and a guest material. Optionally, the organic light-emitting layer 330 is composed of a host material and a guest material. Holes and electrons injected into the organic light-emitting layer 330 may 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.

[0079] The host material of the organic light-emitting layer 330 may include metal chelate compounds, bis(phenylvinyl) derivatives, aromatic amine derivatives, dibenzofuran derivatives or other types of materials.

[0080] In some embodiments of the present application, the main material of the organic light emitting layer 330 is the compound of the present application and RH-P

[0081] The guest material of the organic light-emitting layer 330 can be a compound having a condensed aromatic ring or its derivative, a compound having a heteroaromatic ring or its derivative, an aromatic amine derivative or other materials, and this application does not impose any special restrictions on this. The guest material is also called a doping material or dopant. According to the type of luminescence, it can be divided into fluorescent dopants and phosphorescent dopants. Specific examples of the phosphorescent dopant include, but are not limited to,

[0082] In one embodiment of the present application, the organic electroluminescent device is a red organic electroluminescent device.

[0083] The object material is RD

[0084] The electron transport layer 340 may 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 not limited to, BTB, LiQ, ET-1, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials, and this application does not impose any particular restrictions on this. The materials of the electron transport layer 340 may include, but are not limited to, the following compounds:

[0085] In one embodiment of the present application, the electron transport layer 340 may be composed of ET-1 and LiQ.

[0086] In the present application, cathode 200 may include a cathode material having a small work function that 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. Alternatively, a metal electrode containing magnesium and silver may be included as the cathode.

[0087] In some embodiments, an electron injection layer 350 is further provided 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 an inorganic material such as an alkali metal sulfide or an alkali metal halide, or may include a complex of an alkali metal and an organic matter. In one embodiment of the present application, the electron injection layer 350 may include LiQ.

[0088] In a third aspect, the present application provides an electronic device comprising the organic electroluminescent device described in the second aspect of the present application.

[0089] According to one embodiment, as shown in FIG2 , an electronic device provided is electronic device 400, which includes the above-mentioned 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, including but not limited to computer screens, mobile phone screens, televisions, electronic paper, emergency lighting, optical modules, etc.

[0090] The synthesis method of the compound of the present application is specifically described below in conjunction with synthesis examples, but the present disclosure is not limited thereto.

[0091] Synthesis Example

[0092] 1. Synthesis of intermediate Sub-a1:

[0093] Under nitrogen atmosphere, 3-bromo-1-chlorodibenzo[B,D]furan (19.70 g, 70 mmol) and dry tetrahydrofuran (200 mL) were added to a 500 mL three-necked flask, the system was cooled to -78 ° C, n-butyl lithium solution (2.0 M n-hexane solution, 38.5 mL, 77 mmol) was added dropwise, and after the addition was completed, the temperature was kept (-78 ° C) and stirred for 1 h; trimethyl borate (10.91 g, 105 mL) was added dropwise while maintaining -78 ° C. mol), and after the addition was complete, the temperature was maintained at -78°C for 1 h, and then the system was allowed to warm to room temperature naturally; dilute hydrochloric acid (2M, 58 mL) was added dropwise to the reaction solution, and stirred for 30 min; extraction was performed with dichloromethane (100 mL × 3 times), and the organic phases were combined and dried over anhydrous magnesium sulfate. After filtration, the solvent was removed by distillation under reduced pressure to obtain a crude product; the crude product was slurried with n-heptane and filtered to obtain the intermediate Sub-a1 (11.56 g, yield 67%) as a white solid.

[0094] Intermediates Sub-a2 to Sub-a4 listed in Table 1 were synthesized by the same method as intermediate Sub-a1, except that reactant A was used instead of 3-bromo-1-chlorodibenzo[B,D]furan. The main raw materials used, the synthesized intermediates and their yields are shown in Table 1.

[0095] Table 1

[0096] 2. Synthesis of intermediate Sub-b1:

[0097] 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 added to a 500 mL three-necked flask. Stirring and heating were initiated, and the temperature was raised to reflux 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 distillation under reduced pressure to obtain a crude product. The crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as the mobile phase to obtain intermediate Sub-b1 (11.20 g, 73% yield) as a white solid.

[0098] Intermediates Sub-b2 to Sub-b4 listed in Table 2 were synthesized using the same method as intermediate Sub-b1, except that reactant B was used instead of intermediate Sub-a1. The main raw materials used, the synthesized intermediates and their yields are shown in Table 2.

[0099] Table 2

[0100] 3. Synthesis of intermediate Sub-c1:

[0101] 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. The temperature was cooled to -15°C and maintained for 30 min. Sub-b1 (39.90 g, 130 mmol) was then weighed and dissolved in anhydrous tetrahydrofuran (200 mL). This solution was slowly added dropwise to the reaction system using a constant pressure dropping funnel. The temperature was maintained at -15°C during the addition. After the addition was complete, the reaction was stirred at -15°C for 1 h. The reaction system was then allowed to warm to room temperature and extracted with dichloromethane (3 times, 200 mL). The organic phases were combined, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by distillation under reduced pressure 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 intermediate Sub-c1 (29.60 g, yield 68%) as a red solid.

[0102] Intermediates Sub-c2 to Sub-c4 listed in Table 3 were synthesized using the same method as intermediate Sub-c1, except that reactant C was used instead of intermediate Sub-b1. The main raw materials used, the synthesized intermediates and their yields are shown in Table 3.

[0103] Table 3

[0104] 4. Synthesis of intermediate Sub-d1:

[0105] Under a nitrogen atmosphere, Sub-c1 (39.84 g, 119 mmol), Eaton's reagent (4.5 mL), and chlorobenzene (500 mL) were added sequentially to a 1000 mL three-necked flask. The temperature was raised to reflux and the reaction was stirred for 4 h. After the reaction system reached room temperature, the reaction solution was poured into 1000 mL of deionized water and neutralized with saturated sodium hydroxide solution. The mixture was then extracted with dichloromethane (250 mL × 3 times). The organic phases were combined and dried over anhydrous magnesium sulfate. After filtration, the solvent was removed by distillation under reduced pressure to obtain a crude product. The crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as the mobile phase to obtain Sub-d1 (17.29 g, 48% yield) as a white solid.

[0106] Intermediates Sub-d2 to Sub-d4 listed in Table 4 were synthesized using the same method as intermediate Sub-d1, except that reactant D was used instead of intermediate Sub-c1. The main raw materials used, the synthesized intermediates and their yields are shown in Table 4.

[0107] Table 4

[0108] 5. Synthesis of intermediate Sub-e1:

[0109] Under nitrogen atmosphere, Sub-d1 (15.14 g, 50 mmol), diboronic acid pinacol ester (14.0 g, 55 mmol), potassium acetate (10.8 g, 110 mmol) and 1,4-dioxane (160 mL) were added in sequence to a 500 mL three-necked flask. Stirring and heating were started. When the system was heated 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 quickly added. The temperature was continued to rise to reflux and the reaction was stirred overnight. After the system was cooled to room temperature, 200 mL of water was added to the system, 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, and then rinsed with 100 mL of anhydrous ethanol to obtain a gray solid. The crude product was slurried once with n-heptane, dissolved with 200 mL of toluene, and passed through a silica gel column to remove the catalyst. After concentration, the intermediate Sub-e1 (13.21 g, yield 67%) was obtained as a white solid.

[0110] Intermediates Sub-e2 to Sub-e4 listed in Table 5 were synthesized using the same method as intermediate Sub-e1, except that reactant E was used instead of intermediate Sub-d1. The main raw materials used, the synthesized intermediates and their yields are shown in Table 5.

[0111] Table 5

[0112] 6. Synthesis of intermediate Sub-f1:

[0113] Under nitrogen, 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 added sequentially to a 500 mL three-necked flask. Stirring and heating were initiated, and the temperature was raised to reflux for 8 h. After cooling to room temperature, the mixture was extracted with dichloromethane (100 mL x 3). The organic phases were combined, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by distillation under reduced pressure 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).

[0114] Intermediates Sub-f2 to Sub-f10 listed in Table 6 were synthesized by the same method 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 raw materials used, the synthesized intermediates and their yields are shown in Table 6.

[0115] Table 6

[0116] Synthesis Example 1: Synthesis of Compound 3:

[0117] Under nitrogen, to a 250 mL three-necked flask were added 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-dicyclohexylphosphino-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). The mixture was stirred and heated to reflux for 16 h. After cooling to room temperature, the mixture was extracted with dichloromethane (3 times with 100 mL). The organic phases were combined, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by distillation under reduced pressure 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%) as a yellow-green solid. Mass spectrum (m / z) = 550.19 [M+H] + .

[0118] 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 raw materials used, the synthesized compounds, their mass spectra, and yields are shown in Table 7.

[0119] Table 7

[0120] NMR data of some compounds:

[0121] Compound 9 NMR: 1 H-NMR(400MHz,Methylene-Chloride-D2)δppm 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).

[0122] Compound 177 NMR: 1 H-NMR(400MHz,Methylene-Chloride-D2)δppm 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).

[0123] Example of fabrication and evaluation of organic electroluminescent devices

[0124] Example 1: Preparation of red organic electroluminescent device

[0125] Anodic pretreatment is performed by the following process: the thickness is The ITO / Ag / ITO substrate was cut into a size of 40mm (length) × 40mm (width) × 0.7mm (thickness) and prepared into an experimental substrate with anode and insulating layer patterns using a photolithography process. The surface was treated with ultraviolet ozone and O2:N2 plasma to increase the work function of the substrate anode.

[0126] On the experimental substrate (anode), PD:HT-1 was co-evaporated at an evaporation rate ratio of 2%:98% to form a thickness of hole injection layer.

[0127] Compound HT-1 was vacuum evaporated on the hole injection layer to form a layer with a thickness of hole transport layer.

[0128] Compound HT-2 was vacuum evaporated on the hole transport layer to form a layer with a thickness of electron blocking layer.

[0129] On the electron blocking layer, compound 3:RH-P:RD was co-evaporated at an evaporation rate ratio of 49%:49%:2% to form a film with a thickness of organic light-emitting layer.

[0130] On the organic light-emitting layer, compound ET-1 and LiQ were co-evaporated at an evaporation rate ratio of 1:1 to form a film with a thickness of The electron transport layer is formed by evaporating Yb on the electron transport layer to form a layer with a thickness of Then magnesium (Mg) and silver (Ag) are evaporated on the electron injection layer at an evaporation rate of 1:9 to form a thickness of cathode.

[0131] Finally, compound CP-1 is evaporated on the cathode to form a layer with a thickness of An organic covering layer is formed, thereby completing the manufacture of a red organic electroluminescent device.

[0132] Examples 2 to 75

[0133] An organic electroluminescent device was prepared by the same method as in Example 1, except that the compound in Table 8 was used instead of Compound 3 in Example 1 when forming the organic light-emitting layer.

[0134] Comparative Examples 1 to 3

[0135] An organic electroluminescent device was prepared by the same method as in Example 1, except that Compound A, Compound B and Compound C were used instead of Compound 3 in Example 1 when forming the organic light-emitting layer.

[0136] The main material structures used in the above embodiments and comparative examples are as follows:

[0137] The performance of the red organic electroluminescent devices prepared in Examples 1-75 and Comparative Examples 1-3 was tested. Specifically, at 10 mA / cm 2 The IVL performance of the device was tested under the conditions of T 95 Device life at 20mA / cm 2 The test was carried out under the conditions of , and the test results are shown in Table 8.

[0138] Table 8

[0139] As shown in Table 8, when the compound of the present invention is used as the host material of the red organic electroluminescent device, the current efficiency is increased by at least 10.2% and the life is increased by at least 12.3% compared with Comparative Examples 1 to 3.

[0140] Those skilled in the art will readily appreciate other embodiments of the present invention after considering the specification and practicing the invention disclosed herein. This application is intended to cover any variations, uses, or adaptations of the present invention that follow the general principles of this application and include common knowledge or customary techniques in the art that are not disclosed herein.

Claims

1. An organic compound having the structure shown in Formula 1: in, X and Y are selected from a single bond, 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 are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms; Ar1 and Ar2 are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms; The substituents in L, L1, L2, Ar1 and Ar2 are the same or different and are each independently selected from deuterium, cyano, a halogen group, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 3 to 20 carbon atoms.

2. The organic compound according to claim 1, wherein Formula I is selected from the structure shown in Formula I-1, Formula I-2, Formula I-3 or Formula I-4:

3. The organic compound according to claim 1, wherein L, L1 and L2 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 18 carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 18 carbon atoms; Optionally, the substituents in L, L1 and L2 are each independently selected from deuterium, fluorine, cyano, an alkyl group having 1 to 5 carbon atoms, a trialkylsilyl group having 3 to 8 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, a deuterated alkyl group having 1 to 5 carbon atoms or a phenyl group.

4. The organic compound according to claim 1, wherein L, L1 and L2 are the same or different and are 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, or a substituted or unsubstituted carbazolylene group; Optionally, the substituents in L, L1 and L2 are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl or phenyl.

5. The organic compound according to claim 1, wherein L, L1 and L2 are the same or different and are each independently selected from a single bond or the following groups:

6. The organic compound according to claim 1, wherein Ar1 and Ar2 are each independently selected from a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroaryl group having 12 to 18 carbon atoms; Optionally, the substituents in Ar1 and Ar2 are each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, a deuterated alkyl group having 1 to 5 carbon atoms, a trialkylsilyl group having 3 to 8 carbon atoms, an aryl group having 6 to 12 carbon atoms, or a heteroaryl group having 5 to 12 carbon atoms.

7. The organic compound according to claim 1, wherein Ar1 and Ar2 are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl; Optionally, the substituents in Ar1 and Ar2 are each independently selected from deuterium, fluorine, cyano, trideuteromethyl, trimethylsilyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, phenyl or naphthyl.

8. The organic compound according to claim 1, wherein Ar1 and Ar2 are the same or different and are each independently selected from the group consisting of:

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

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

11. 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 10; Optionally, 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.

12. An electronic device, characterized in that The organic electroluminescent device according to claim 11 is included.

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