Organic compound, organic electroluminescent device containing said compound, and electronic apparatus

Abstract

The present application relates to an organic compound, an organic electroluminescent device containing said compound, and an electronic apparatus. The organic compound has a structure as represented by formula 1. Applying the organic compound in an organic electroluminescent device can significantly improve the performance of the 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 Chinese patent application No. CN202311780849.0 filed on December 21, 2023. 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 electroluminescence, and in particular to an organic compound and an organic electroluminescent device and an electronic apparatus containing the same. Background Art

[0004] Currently, organic electroluminescent devices are considered the next generation of display and lighting technology due to their advantages such as active light emission, high current efficiency, low power consumption, light weight, thinness, fast response speed, and wide viewing angle. Organic electroluminescent devices generally include a cathode and an anode arranged relative to each other, as well as a functional layer arranged between the cathode and the anode. When voltage is applied to the cathode and anode, the two electrodes generate an electric field. Under the action of the electric field, electrons on the cathode side move toward the electroluminescent layer, and holes on the anode side also move toward the organic light-emitting layer. Electrons and holes combine in the electroluminescent layer to form excitons. The excitons are in an excited state and release energy outward, thereby causing the electroluminescent layer to emit light outward.

[0005] Organic electroluminescent devices can be of various structures, such as single-layer structures and stacked structures. A single-layer organic electroluminescent device contains only one light-emitting unit between the anode and cathode, while a stacked organic electroluminescent device is composed of multiple light-emitting units stacked together. A light-emitting unit usually contains at least one organic light-emitting layer, a hole transport layer and an electron transport layer. On this basis, the light-emitting unit can further include a hole injection layer, an electron injection layer, a hole blocking layer and an electron blocking layer. There is a charge generation layer (CGL) between adjacent light-emitting units for charge generation and movement. The CGL is constructed in a pn form, including an n-type charge generation layer (n-CGL) and a p-type charge generation layer (p-CGL). Among them, the p-type material mainly generates holes, while the n-type material is doped with a low work function metal through the electron transport layer material to generate electrons.

[0006] The main challenges facing existing organic electroluminescent devices are lifespan and efficiency. As displays become larger, the voltage required for display increases. Therefore, it is necessary to continue developing new materials to further improve the performance of organic electroluminescent devices.

[0007] Summary of the Invention

[0008] The purpose of the present application is to provide an organic compound and an organic electroluminescent device and an electronic device comprising the same. The use of the organic compound in an organic electroluminescent device can improve the performance of the device.

[0009] The first aspect of the present application provides an organic compound having a structure shown in Formula 1:

[0010] Wherein, Q is Formula 2 or Formula 3;

[0011] 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;

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

[0013] Each R is the same or different and is independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms;

[0014] The substituents in R are the same or different and are each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms, or a heteroaryl group having 3 to 12 carbon atoms;

[0015] n is the number of R, and n is selected from 0, 1, 2, 3, 4, 5, 6 or 7. When n is greater than 1, any two Rs are the same or different; optionally, any two adjacent Rs form an aromatic ring with 6 to 14 carbon atoms.

[0016] The second aspect of the present application provides an organic electroluminescent device, comprising an anode and a cathode arranged opposite to each other, and a functional layer arranged between the anode and the cathode; the functional layer comprises the organic compound described in the first aspect of the present application.

[0017] The third aspect of the present application provides an electronic device, comprising the organic electroluminescent device described in the second aspect of the present application.

[0018] The compound of the present application is a structure formed by a phenanthroline group and two quinolyl-substituted pyridyl groups. This structure has a large conjugated plane, effectively adjusting the intermolecular stacking, thereby improving electron mobility and facilitating charge transport. At the same time, the compound of the present application can effectively complex with metals. When used as a charge generation layer material, it can improve the efficiency of charge generation, thereby improving current efficiency and extending the service life of organic electroluminescent devices.

[0019] Other features and advantages of the present application will be described in detail in the subsequent detailed description. BRIEF DESCRIPTION OF THE DRAWINGS

[0020] 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.

[0021] FIG1 is a schematic structural diagram of an organic electroluminescent device according to an embodiment of the present application.

[0022] FIG2 is a schematic structural diagram of an organic electroluminescent device according to another embodiment of the present application.

[0023] FIG3 is a schematic structural diagram of an electronic device according to an embodiment of the present application.

[0024] Description of Reference Numerals

[0025] 100, anode 200, cathode 300, functional layer 310, hole injection layer

[0026] 321, hole transport layer 322, electron blocking layer 330, organic light emitting layer 340, electron transport layer

[0027] 350, electron injection layer 411, first hole transport layer 412, first hole adjustment layer 413, first organic light emitting layer

[0028] 414, first electron transport layer 421, n-type charge generation layer 422, p-type charge generation layer 431, second hole transport layer

[0029] 432, second hole adjustment layer 433, second organic light-emitting layer 434, second electron transport layer 410, first light-emitting unit

[0030] 420 , charge generation layer 430 , second light emitting unit 500 , electronic device. DETAILED DESCRIPTION

[0031] The exemplary embodiments will now be described more fully with reference to the accompanying drawings. However, the exemplary embodiments can be implemented in a variety of forms and should not be construed as limited to the examples set forth herein; rather, these embodiments are provided so that this application will be more comprehensive and complete and will fully convey the 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.

[0032] In a first aspect, the present application provides an organic compound having a structure shown in Formula 1:

[0033] Wherein, Q is Formula 2 or Formula 3;

[0034] 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;

[0035] The substituents in L1 and L2 are the same or different and are each independently selected from deuterium, a halogen group, a cyano group, a haloalkyl group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms;

[0036] Each R is the same or different and is independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms;

[0037] The substituents in R are the same or different and are each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms, or a heteroaryl group having 3 to 12 carbon atoms;

[0038] n is the number of R, and n is selected from 0, 1, 2, 3, 4, 5, 6 or 7. When n is greater than 1, any two Rs are the same or different; optionally, any two adjacent Rs form an aromatic ring with 6 to 14 carbon atoms.

[0039] In this application, the descriptions “each independently selected from” and “respectively independently selected from” are interchangeable 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.

[0040] In this application, the terms "optionally" and "optionally" mean that the event or circumstances described subsequently may but need not occur, and the description includes situations where the event or circumstances occur or do not occur. For example, "optionally, any two adjacent substituents form an xx ring" means that the two substituents can form a ring but do not have to form a ring, including: situations where two adjacent substituents form a ring and situations where two adjacent substituents do not form a ring. For another example, "optionally, any two adjacent R forms an aromatic ring with 6 to 14 carbon atoms" means that the two adjacent R together with the carbon atoms to which they are attached form an aromatic ring with 6 to 14 carbon atoms, or the two R can also exist independently.

[0041] In this application, the term "substituted or unsubstituted" means that the functional group described after the term may or may not have a substituent (hereinafter, for ease of description, the substituents are collectively referred to as Rc). For example, "substituted or unsubstituted aryl" refers to an aryl group or an unsubstituted aryl group having the substituent Rc. The substituent Rc can be, for example, deuterium, a halogen group, a cyano group, an alkyl group, a trialkylsilyl group, a haloalkyl group, a cycloalkyl group, an aryl group, a heteroaryl group, etc.

[0042] 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.

[0043] 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 a carbon-carbon bond, a monocyclic aryl and a condensed ring aryl connected by a carbon-carbon bond, two or more condensed ring aryl groups connected by a carbon-carbon bond. That is, unless otherwise indicated, two or more aromatic groups connected by a carbon-carbon bond can also be considered as aryl of the present application. Wherein, condensed ring aryl can, for example, 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. For example, in the present application, biphenyl, terphenyl etc. are aryl. Examples of aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, anthracenyl, phenanthrenyl, biphenyl, terphenyl, benzo[9,10]phenanthrenyl, pyrenyl, benzofluoranthenyl, In the present application, the arylene group refers to a divalent group formed by further losing a hydrogen atom from an aryl group.

[0044] In the present application, a substituted aryl group may be an aryl group in which one or more hydrogen atoms are substituted 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, etc. Specific examples of heteroaryl-substituted aryl groups include, but are not limited to, dibenzofuranyl-substituted phenyl, dibenzothienyl-substituted phenyl, pyridyl-substituted phenyl, 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 refers to a total number of carbon atoms in the aryl group and the substituents.

[0045] In the present application, a heteroaryl group refers to a monovalent aromatic ring or a derivative thereof containing at least one heteroatom in the ring, and the heteroatom can be one or more of B, O, N, P, Si, Se and S. A heteroaryl group can be a monocyclic heteroaryl group or a polycyclic heteroaryl group. In other words, a heteroaryl group can be a single aromatic ring system or multiple aromatic ring systems connected by carbon-carbon bonds, and any aromatic ring system can be an aromatic monocyclic ring or an aromatic condensed 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. In the present application, the heteroarylene group refers to a divalent group formed by further losing a hydrogen atom from a heteroaryl group.

[0046] In the present application, a substituted heteroaryl group may be a heteroaryl group in which one or more hydrogen atoms are replaced by groups such as deuterium atoms, halogen groups, cyano groups, aryl groups, heteroaryl groups, trialkylsilyl groups, alkyl groups, haloalkyl groups, etc. Specific examples of aryl-substituted heteroaryl groups include, but are not limited to, phenyl-substituted dibenzofuranyl groups, phenyl-substituted dibenzothienyl groups, phenyl-substituted pyridyl groups, 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.

[0047] 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, and specific examples of the aryl group as a substituent include, but are not limited to, phenyl, biphenyl, naphthyl, anthracenyl, base.

[0048] 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.

[0049] In the present application, the alkyl group having 1 to 10 carbon atoms may include a straight-chain alkyl group having 1 to 10 carbon atoms and a branched-chain alkyl group having 3 to 10 carbon atoms. The number of carbon atoms in the alkyl group may 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, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, nonyl, decyl, 3,7-dimethyloctyl, and the like.

[0050] In the present application, the halogen group may be, for example, fluorine, chlorine, bromine, or iodine.

[0051] In the present application, specific examples of trialkylsilyl include, but are not limited to, trimethylsilyl, triethylsilyl, and the like.

[0052] In the present application, specific examples of haloalkyl include, but are not limited to, trifluoromethyl.

[0053] In this application, a non-positioned connecting bond refers to a single bond extending from the ring system. This means that one end of the link can be connected to any position in the ring system that the link passes through, and the other end is connected to the rest of the compound molecule. For example, as shown in the following formula (f), the naphthyl represented by formula (f) is connected to other positions of the molecule via two non-positional linkers that pass through the bicyclic ring. The meaning of this includes any possible connection method shown in formulas (f-1) to (f-10):

[0054] For 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 benzene ring. The meaning represented by it includes any possible connection method shown in formulas (X'-1) to (X'-4):

[0055] In some embodiments of the present application, the organic compound has a structure shown in the following Formula II or Formula I-II:

[0056] R, L1, L2 and n in Formula II to Formula I-II are the same as defined in Formula 1.

[0057] In some embodiments of the present application, 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 22 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 18 carbon atoms. For example, 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, 18, 19, 20, 21, or 22 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, or 18 carbon atoms.

[0058] In some embodiments of the present application, the substituents in L1 and L2 are the same or different and are each independently selected from deuterium, fluorine, cyano, a haloalkyl group having 1 to 5 carbon atoms, a trialkylsilyl group having 3 to 6 carbon atoms, an alkyl group having 1 to 5 carbon atoms, an aryl group having 6 to 16 carbon atoms, or a heteroaryl group having 3 to 12 carbon atoms.

[0059] In some embodiments of the present application, 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 anthrylene group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyridinyl group, or a substituted or unsubstituted pyrazinyl group.

[0060] Optionally, the substituents in L1 and L2 are the same or different and are each independently selected from deuterium, fluorine, cyano, trifluoromethyl, trimethylsilyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, phenanthrenyl, anthracenyl, pyrenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, pyridyl, pyrimidinyl, pyrazinyl or quinolyl.

[0061] In some embodiments of the present application, L1 and L2 are the same or different, and are each independently selected from a single bond or the group consisting of the following groups:

[0062] In some embodiments of the present application, L1 and L2 are the same or different, and are each independently selected from a single bond or the group consisting of the following groups:

[0063] In some embodiments of the present application, is selected from the group consisting of a single bond or the following groups:

[0064] In some embodiments of the present application, is selected from the group consisting of a single bond or the following groups:

[0065] In one embodiment of the present application, each R is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted quinolyl, or substituted or unsubstituted isoquinolyl.

[0066] Optionally, the substituents in R are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl or phenyl. Optionally, any two adjacent Rs form a benzene ring or a naphthalene ring.

[0067] In one embodiment of the present application, each R is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, phenyl, pyridyl, pyrimidinyl, triazinyl, naphthyl, phenanthrenyl, anthracenyl, deuterated phenyl, pentadeuterated phenyl, pentamethyl-substituted phenyl, methyl-substituted phenyl, pentafluoro-substituted phenyl, fluorine-substituted phenyl, cyano-substituted phenyl, tert-butyl-substituted phenyl, and tetramethyl-substituted tetrahydronaphthyl.

[0068] Specifically, the organic compound is selected from the group consisting of the following compounds:

[0069] In a second aspect, the present application provides an organic electroluminescent device, comprising an anode and a cathode arranged opposite to each other, and a functional layer arranged between the anode and the cathode; the functional layer comprises the organic compound provided in the first aspect of the present application.

[0070] Optionally, the functional layer includes an electron transport layer, and the electron transport layer includes the organic compound described in this application.

[0071] In one embodiment of the present application, the structure of the organic electroluminescent device is shown in Figure 1, including an anode 100 and a cathode 200 arranged opposite to each other, and a functional layer 300 arranged between the anode 100 and the cathode 200; the functional layer 300 includes a hole injection layer 310, a hole transport layer 321, an electron blocking layer 322, an organic light-emitting layer 330, an electron transport layer 340 and an electron injection layer 350, and the electron transport layer 340 contains the organic compound described in this application.

[0072] In the present application, the anode 100 includes the following anode materials, which are preferably materials 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. Optionally, a transparent electrode comprising indium tin oxide (ITO) as the anode is included.

[0073] In the present application, the hole injection layer 310 may be made of benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives or other materials, and the present application does not impose any special restrictions on this. The material of the hole injection layer 310 is, for example, selected from the following compounds or any combination thereof:

[0074] In one embodiment of the present application, the hole injection layer 310 is composed of HT-1 and PD-1.

[0075] In some embodiments of the present application, the hole transport material may be selected from triarylamine compounds or other types of compounds, and those skilled in the art may select them according to the prior art. For example, the hole transport layer material is selected from the group consisting of the following compounds.

[0076] In one embodiment of the present application, the material of the hole transport layer 321 includes HT-1.

[0077] In one embodiment of the present application, the electron blocking layer 322 includes one or more electron blocking materials, which can be selected from carbazole polymers or other types of compounds, and the present application does not specifically limit this. For example, in some embodiments of the present application, the electron blocking layer 322 is compound EB-1

[0078] Alternatively, the organic light-emitting layer material may be composed of a single light-emitting material, or may include a host material and a guest material. Alternatively, the organic light-emitting layer 330 may be 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] Alternatively, the main material of the organic light-emitting layer 330 may include metal chelate compounds, bisphenylethylene derivatives, aromatic amine derivatives, dibenzofuran derivatives or other types of materials. The main material of the organic light-emitting layer 330 may be a single main material or a mixed main material. In one embodiment of the present application, the main material of the organic light-emitting layer 330 is BH-1

[0080] In a specific embodiment of the present application, the guest material of the organic light-emitting layer 330 is BD-1

[0081] In the present application, the electron injection layer 350 may include inorganic materials such as alkali metal sulfides, alkali metal halides, or may include a complex of alkali metals and organic matter. In one embodiment of the present application, the electron injection layer 350 includes Yb.

[0082] Optionally, 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 material may generally include a metal complex and / or a nitrogen-containing heterocyclic derivative, wherein the metal complex material may be selected from, for example, LiQ, Alq3, etc. In one embodiment of the present application, the electron transport layer 340 is composed of the compound of the present application and LiQ.

[0083] In the present application, cathode 200 includes 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. Optionally, a metal electrode containing magnesium and silver is included as the cathode.

[0084] In addition, the present application provides another organic electroluminescent device as shown in Figure 2 . The organic electroluminescent device includes an anode and a cathode, and a functional layer disposed between the anode and the cathode. The functional layer includes a first light-emitting unit, a second light-emitting unit, and a charge generation layer. The charge generation layer includes the organic compound described in the present application. The organic electroluminescent device shown in Figure 2 is hereinafter referred to as a stacked organic electroluminescent device.

[0085] The stacked organic electroluminescent device shown in FIG2 includes an anode 100, a cathode 200, a hole injection layer 310, an electron injection layer 350, a first light-emitting unit 410, a second light-emitting unit 430, and a charge generation layer 420. The first light-emitting unit 410, the second light-emitting unit 430, and the charge generation layer 420 are located between the cathode 100 and the anode 200. The charge generation layer 420 is located between the first light-emitting unit 410 and the second light-emitting unit 430. The charge generation layer 420 comprises the organic compound described herein.

[0086] In one embodiment of the present application, the first light-emitting unit 410 includes a first hole transport layer 411, a first hole adjustment layer 412, a first organic light-emitting layer 413 and a first electron transport layer 414; the second light-emitting unit 430 includes a second hole transport layer 431, a second hole adjustment layer 432, a second organic light-emitting layer 433, and a second electron transport layer 434.

[0087] In one embodiment of the present application, the charge generation layer 420 includes an n-type charge generation layer (n-CGL) 421 and a p-type charge generation layer (p-CGL) 422. The n-type charge generation layer 421 provides electrons to the first electron transport layer 414 of the first light-emitting unit 410, and the p-type charge generation layer 422 provides holes to the second hole transport layer 431 of the second light-emitting unit 430. In one embodiment of the present application, the n-type charge generation layer includes the organic compound described in the present application.

[0088] In one embodiment of the present application, the n-type charge generation layer is composed of the organic compound described in the present application and a metal doping material. Optionally, the metal doping material is Li, Ca, Ag, Cs or Yb.

[0089] In one embodiment of the present application, the p-CGL layer comprises HT-1 and PD-1.

[0090] In the present application, the anode 100 includes an anode material. Optionally, the anode material includes indium tin oxide (ITO).

[0091] In one embodiment of the present application, the hole injection layer 310 is composed of HT-1 and PD-1.

[0092] In one embodiment of the present application, the material of the first hole transport layer 411 and the second hole transport layer 431 includes RP-1.

[0093] In one embodiment of the present application, the material of the first hole adjustment layer 412 and the second hole adjustment layer 432 includes RP-1.

[0094] In the present application, the first organic light-emitting layer of the first light-emitting unit; and the second organic light-emitting layer of the second light-emitting unit, each may include the same or different host materials and the same or different guest materials.

[0095] In a specific embodiment of the present application, the main material of the first organic light-emitting layer 413 and the second organic light-emitting layer 433 is RH-1

[0096] In a specific embodiment of the present application, the guest material of the first organic light-emitting layer 413 and the second organic light-emitting layer 433 is RD-1

[0097] In a specific embodiment of the present application, the materials of the first electron transport layer 414 and the second electron transport layer 434 include ET-1 and LiQ.

[0098] In one embodiment of the present application, the electron injection layer 350 includes Yb.

[0099] In a specific embodiment of the present application, the cathode 200 includes a cathode material, and the cathode material includes magnesium (Mg) and silver (Ag).

[0100] In a third aspect, the present application provides an electronic device comprising the organic electroluminescent device according to the second aspect of the present application.

[0101] According to one embodiment, as shown in FIG3 , an electronic device 500 is provided, which includes the above-mentioned organic electroluminescent device. Electronic device 500 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.

[0102] The following is a detailed description of the synthesis method of the organic compound of the present application in conjunction with the synthesis examples, but the present application is not limited thereto. The following is a detailed description of the synthesis method of the organic compound of the present application in conjunction with the synthesis examples, but the present application is not limited thereto.

[0103] The compounds whose synthesis methods are not mentioned in this application are all raw materials obtained through commercial channels.

[0104] Synthesis example

[0105] 1. Synthesis of intermediate IM A-1

[0106] 2,6-Dibromo-4-chloropyridine (10 g, 36.85 mmol) and quinoline-2-boronic acid (14.03 g, 81.08 mmol) were dissolved in 80 mL of toluene. Tetrakis(triphenylphosphine)palladium (0.43 g, 0.369 mmol), K2CO3 (20.34 g, 147.42 mmol), 10 mL of ethanol, and 10 mL of water were added. The mixture was heated to reflux under a nitrogen atmosphere for 12 h. After cooling to room temperature, the mixture was extracted with water and dichloromethane, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting solid was purified by column chromatography using ethyl acetate:n-heptane = 1:9 (v / v) to afford IM A-1 (7.18 g, 53% yield).

[0107] IM A-2 was synthesized in the same manner as IM A-1, except that starting material 1 was used instead of quinoline-2-boronic acid. The main starting materials used, the synthesized IM A-2, and their yields are shown in Table 1.

[0108] Table 1

[0109] 2. Synthesis of IM B-1

[0110] 2,9-Dibromo-1,10-phenanthroline (20 g, 59.17 mmol) and phenylboronic acid (7.21 g, 59.17 mmol) were dissolved in 160 mL of toluene. Tetrakis(triphenylphosphine)palladium (0.34 g, 0.296 mmol), K2CO3 (16.33 g, 118.34 mmol), 20 mL of ethanol, and 20 mL of water were added. The mixture was heated under reflux for 12 h under a nitrogen atmosphere. After cooling to room temperature, the mixture was extracted with water and dichloromethane, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting solid was purified by column chromatography using ethyl acetate:n-heptane = 1:9 (v / v) to yield IM B-1 (8.13 g, 41% yield).

[0111] IM BX was synthesized in the same manner as IM B-1, except that starting material 2 was used instead of 2,9-dibromo-1,10-phenanthroline, and starting material 3 was used instead of phenylboronic acid. The main starting materials used, the synthesized IM BX, and their yields are shown in Table 2.

[0112] Table 2

[0113] 3. Synthesis of IM C-1

[0114] IM B-1 (8 g, 23.87 mmol) and 4-chlorophenylboronic acid (3.73 g, 23.87 mmol) were dissolved in 64 mL of toluene. Tetrakis(triphenylphosphine)palladium (0.14 g, 0.119 mmol), KCO (6.59 g, 47.73 mmol), 8 mL of ethanol, and 8 mL of water were added. The mixture was heated to reflux under a nitrogen atmosphere for 6 h. After cooling to room temperature, the mixture was extracted with water and dichloromethane, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting solid was recrystallized from dichloromethane:n-heptane = 1:4 (v / v) to yield IM C-1 (5.52 g, 63% yield).

[0115] IM CX was synthesized in the same manner as IM C-1, except that starting material 4 was used instead of IM B-1, and starting material 5 was used instead of 4-chlorophenylboronic acid. The main starting materials used, the synthesized IM CX, and their yields are shown in Table 3.

[0116] Table 3

[0117] 4. Synthesis of IMD-1

[0118] IM C-1 (5 g, 13.63 mmol) and pinacol diboronate (4.15 g, 16.36 mmol) were dissolved in 50 mL of 1,4-dioxane, followed by the addition of Pd(dba2)3 (0.12 g, 0.136 mmol), X-phos (0.13 g, 0.273 mmol), and potassium acetate (2.01 g, 20.44 mmol). The mixture was heated under reflux for 5 h under a nitrogen atmosphere. After cooling to room temperature, the mixture was extracted with water and dichloromethane, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting solid was recrystallized from dichloromethane:n-heptane = 1:3 (v / v) to afford IM D-1 (4.87 g, 78% yield).

[0119] IM DX was synthesized in the same manner as IM D-1, except that starting material 6 was used instead of IM C-1. The main starting materials used, the synthesized IM DX and their yields are shown in Table 4.

[0120] Table 4

[0121] Synthesis Example 1. Synthesis of Compound 3

[0122] IM A-1 (5 g, 13.6 mmol) and IM D-28 (5.2 g, 13.6 mmol) were dissolved in 40 mL of toluene. Tetrakis(triphenylphosphine)palladium (0.16 g, 0.136 mmol), K2CO3 (3.8 g, 27.2 mmol), 5 mL of ethanol, and 5 mL of water were added. The mixture was heated to reflux under a nitrogen atmosphere for 12 h. After cooling to room temperature, 100 mL of water was added and stirred for 30 min. The solid was then filtered and rinsed with 100 mL of ethanol three times. The resulting solid was recrystallized from dichloromethane to obtain compound 3 (3.7 g, 46% yield). Mass spectrum (m / z) = 588.21 [M+H] + .

[0123] Compound X listed in Table 5 was synthesized in the same manner as compound 3, except that starting material 7 was used instead of IM A-1, and starting material 8 was used instead of IM D-28. The main starting materials used, the synthesized compounds, their yields, and mass spectra are shown in Table 5.

[0124] Table 5

[0125] NMR data of some compounds

[0126] NMR data of compound 3:

[0127] 1 H-NMR(CD3Cl,400MHz):9.15(d,1H),8.96(s,2H),8.89(s,1H),8.53(d,2H),8.33- 8.27(m,6H),8.06(d,1H),7.99-7.96(m,3H),7.85-7.81(m,5H),7.63-7.52(m,4H).

[0128] NMR data of compound 117:

[0129] 1H-NMR(CD3Cl,400MHz):8.96(s,2H),8.89(s,1H),8.53(d,2H),8.35-8.27(m,8 H),8.19-8.11(m,2H),7.99-7.96(m,3H),7.87-7.79(m,5H),7.62-7.42(m,6H).

[0130] Example 1: Blue organic electroluminescent device

[0131] The anode was prepared by the following process: the thickness of The ITO / Ag / ITO substrate was cut into a size of 40 mm (length) × 40 mm (width) × 0.7 mm (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 anode, and the surface of the experimental substrate was cleaned with an organic solvent to remove impurities and oil stains on the surface of the experimental substrate.

[0132] Compounds HT-1 and PD-1 were co-evaporated on the experimental substrate (anode) at an evaporation rate ratio of 97:3 to form a film with a thickness of hole injection layer.

[0133] Compound HT-1 was vacuum evaporated on the hole injection layer to form a layer with a thickness of hole transport layer.

[0134] Compound EB-1 was vacuum evaporated on the hole transport layer to form a layer with a thickness of electron blocking layer.

[0135] On the electron blocking layer, compound BH-1 and compound BD-1 were co-evaporated at an evaporation rate ratio of 98:2 to form a film with a thickness of Organic light-emitting layer

[0136] On the organic light emitting layer, compound 3 and LiQ were co-evaporated at an evaporation rate ratio of 1:1 to form a film with a thickness of electron transport layer.

[0137] On the electron transport layer, ytterbium (Yb) is vacuum evaporated to form a layer with a thickness of Then, magnesium (Mg) and silver (Ag) were co-evaporated on the electron injection layer at an evaporation rate ratio of 1:9 to form a layer with a thickness of cathode.

[0138] Finally, compound CP-1 was vacuum-evaporated on the cathode to form a layer with a thickness of The cathode covering layer is formed, thereby completing the manufacture of the blue organic electroluminescent device.

[0139] Example 2 to Example 10

[0140] An organic electroluminescent device was prepared by the same method as in Example 1, except that the compound in Table 6 was used instead of Compound 3 in Example 1 when preparing the electron transport layer.

[0141] Comparative Example 1 to Comparative Example 3

[0142] 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 preparing the electron transport layer.

[0143] The structures of the compounds used in preparing the devices of the above embodiments and comparative examples are shown below:

[0144] The performance of the blue organic electroluminescent devices prepared in Examples 1 to 10 and Comparative Examples 1 to 3 was tested. Specifically, the blue organic electroluminescent devices were tested at 15 mA / cm 2 The IVL performance and T95 device life of the device were tested under the conditions of , and the test results are shown in Table 6 below.

[0145] Table 6

[0146] As shown in Table 6 above, when the compounds of the present application are used in the electron transport layer of a blue organic electroluminescent device, device performance can be significantly improved. Specifically, compared to the devices of Comparative Examples 1-3, the current efficiency of the devices of Examples 1-10 is improved by at least 12.4%, and the device life is improved by at least 11.5%.

[0147] In order to further illustrate the application of the compound of the present application as a charge generation layer in a stacked organic electroluminescent device, the performance of the material of the present application is studied by constructing a stacked device.

[0148] Example 11: Red stacked organic electroluminescent device

[0149] The device was prepared by the following process: On the ITO / Ag / ITO experimental substrate, the surface was treated with ultraviolet, ozone and O2:N2 plasma to increase the work function of the anode, and the surface of the experimental substrate was cleaned with an organic solvent to remove impurities and oil stains on the surface of the experimental substrate.

[0150] HT-1 and PD-1 were co-evaporated on the above experimental substrate at an evaporation rate ratio of 98:2 to form a film with a thickness of hole injection layer.

[0151] Compound RP-1 was vacuum-deposited on the hole injection layer to form a layer with a thickness of The first hole transport layer.

[0152] Compound RP-1 was vacuum evaporated on the first hole transport layer to form a layer with a thickness of The first hole adjustment layer.

[0153] On the first hole adjustment layer, compound RH-1 and compound RD-1 were co-evaporated at an evaporation rate ratio of 98:2 to form a layer with a thickness of a first organic light-emitting layer.

[0154] On the first 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 first electron transport layer.

[0155] The above is the first light-emitting unit.

[0156] Next, compound 7 and Yb were co-evaporated on the first electron transport layer at an evaporation rate ratio of 99:1 to form a layer with a thickness of Then, compound HT-1 and PD-1 were co-evaporated at a deposition rate ratio of 95:5 to form an n-type charge generation layer with a thickness of p-type charge generation layer.

[0157] The above is the charge generating layer.

[0158] On the P-type charge generation layer, compound HT-1 was vacuum evaporated to form a layer with a thickness of a second hole transport layer.

[0159] On the second hole transport layer, compound RP-1 was vacuum evaporated to form a layer with a thickness of The second hole adjustment layer.

[0160] On the second hole adjustment layer, compound RH-1 and compound RD-1 were co-evaporated at an evaporation rate ratio of 98:2 to form a layer with a thickness of a second organic light-emitting layer.

[0161] On the second 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 second electron transport layer.

[0162] The above is the second light-emitting unit.

[0163] Finally, Yb was evaporated on the second electron transport layer to form a thickness of Then, magnesium (Mg) and silver (Ag) are co-evaporated on the electron injection layer at an evaporation rate ratio of 1:9 to form a film with a thickness of cathode.

[0164] In addition, compound CP-1 was vacuum-evaporated on the cathode to form a layer with a thickness of The cathode covering layer is formed, thereby completing the manufacture of the red stacked organic electroluminescent device.

[0165] Example 12 to Example 41

[0166] An organic electroluminescent device was prepared by the same method as in Example 11, except that the compound in Table 7 was used instead of Compound 7 in Example 11 when preparing the n-type charge generation layer.

[0167] Comparative Examples 4 to 7

[0168] An organic electroluminescent device was prepared by the same method as in Example 11, except that Compounds D, E, F, and G were used instead of Compound 7 in Example 11 when preparing the n-type charge generation layer.

[0169] The structures of the compounds used in preparing the devices of the above embodiments and comparative examples are shown below:

[0170] The performance of the red stacked organic electroluminescent devices prepared in Examples 11 to 41 and Comparative Examples 4 to 7 was tested. Specifically, at 15 mA / cm 2 The IVL performance of the device was tested under the conditions of 20mA / cm 2 The T95 device life was tested under the conditions of , and the test results are shown in Table 7 below.

[0171] Table 7

[0172] As shown in Table 7 above, when the compounds of the present application are used in the n-type charge generation layer of a red stacked organic electroluminescent device, device performance can be significantly improved. Specifically, compared to the devices of Comparative Examples 4-7, the current efficiency of the devices of Examples 11-41 is improved by at least 13.3%, and the lifetime is improved by at least 12.7%.

Claims

1. An organic compound, characterized in that The organic compound has a structure shown in Formula 1: Wherein, Q is Formula 2 or Formula 3; 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; The substituents in L1 and L2 are the same or different and are independently selected from deuterium, a halogen group, a cyano group, a haloalkyl group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 3 to 20 carbon atoms; Each R is the same or different and is independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms; The substituents in R are the same or different and are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms, or a heteroaryl group having 3 to 12 carbon atoms; n is the number of R, and n is selected from 0, 1, 2, 3, 4, 5, 6 or 7. When n is greater than 1, any two Rs are the same or different; optionally, any two adjacent Rs form an aromatic ring with 6 to 14 carbon atoms.

2. The organic compound according to claim 1, wherein 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 22 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 18 carbon atoms; Optionally, the substituents in L1 and L2 are the same or different and are each independently selected from deuterium, fluorine, cyano, a haloalkyl group having 1 to 5 carbon atoms, a trialkylsilyl group having 3 to 6 carbon atoms, an alkyl group having 1 to 5 carbon atoms, an aryl group having 6 to 16 carbon atoms, or a heteroaryl group having 3 to 12 carbon atoms.

3. The organic compound according to claim 1, wherein 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 anthrylene group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyridinyl group, or a substituted or unsubstituted pyrazinyl group; Optionally, the substituents in L1 and L2 are the same or different and are each independently selected from deuterium, fluorine, cyano, trifluoromethyl, trimethylsilyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, phenanthryl, anthracenyl, pyrenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, pyridyl, pyrimidinyl, pyrazinyl or quinolyl.

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

5. The organic compound according to claim 1, wherein is selected from the group consisting of a single bond or the following groups:

6. The organic compound according to claim 1, wherein each R is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted quinolyl, or substituted or unsubstituted isoquinolyl; Optionally, the substituents in R are the same or different and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl or phenyl. Optionally, any two adjacent R form a benzene ring or a naphthalene ring.

7. The organic compound according to claim 1, wherein Each R is the same or different and is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, phenyl, pyridyl, pyrimidinyl, triazinyl, naphthyl, phenanthryl, anthracenyl, deuterated phenyl, pentadeuterated phenyl, pentamethyl-substituted phenyl, methyl-substituted phenyl, pentafluoro-substituted phenyl, fluorine-substituted phenyl, cyano-substituted phenyl, tert-butyl-substituted phenyl, and tetramethyl-substituted tetrahydronaphthyl.

8. The organic compound according to claim 1, wherein The organic compound is selected from the group consisting of the following compounds:

9. An organic electroluminescent device comprising an anode and a cathode, and a functional layer disposed between the anode and the cathode; characterized in that: The functional layer contains the organic compound according to any one of claims 1 to 8.

10. The organic electroluminescent device according to claim 9, wherein: The functional layer includes an electron transport layer, and the electron transport layer includes the organic compound according to any one of claims 1 to 8. 11 . The organic electroluminescent device according to claim 9 , wherein the functional layer comprises a first light-emitting unit, a second light-emitting unit and a charge generation layer; and the charge generation layer comprises the organic compound according to claim 1 .

12. An electronic device comprising the organic electroluminescent device according to any one of claims 9 to 11.

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