Organic compound, electronic component using same, and electronic apparatus

Abstract

The present invention relates to an organic compound, an electronic component using same, and an electronic apparatus. The organic compound has a structure shown in formula I. The organic compound is applied to an organic electroluminescence device to significantly improve the performance of the device.

Description

Organic compound and electronic component and electronic device using the same

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims priority to Chinese patent application No. CN202410338286.8 filed on March 22, 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 electroluminescence, and in particular to an organic compound and an electronic component and an electronic device using 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 organic light-emitting layer, and holes on the anode side also move toward the organic light-emitting layer. Electrons and holes combine in the organic light-emitting layer to form excitons. The excitons are in an excited state and release energy outward, thereby causing the organic light-emitting layer to emit light outward.

[0005] Organic electroluminescent devices can be of various structures, such as single-layer structures and stacked structures. Single-layer organic electroluminescent devices include only one light-emitting unit between the anode and cathode, while stacked organic electroluminescent devices are composed of multiple light-emitting units stacked together. A light-emitting unit generally includes at least one light-emitting layer, at least one hole transport layer and at least one electron transport layer. On this basis, the light-emitting unit may 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 of existing organic electroluminescent devices are lifespan and efficiency. Furthermore, as displays become larger, the voltage required for display becomes higher. Therefore, it is necessary to continue developing new materials to further improve the performance of organic electroluminescent devices. Summary of the Invention

[0007] The purpose of the present application is to provide an organic compound and an electronic component and an electronic device using the same, wherein the organic compound is 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 I:

[0009] Where Q is

[0010] Each R1 is independently hydrogen or

[0011] Each R2 is independently hydrogen or

[0012] X1 and X2 are the same or different and are each independently selected from O or S;

[0013] m represents the number of R1, m is selected from 1, 2 or 3; when m is greater than 1, any two R1 are the same or different;

[0014] n represents the number of R2, and n is selected from 1, 2, 3 or 4; when n is greater than 1, any two R2 are the same or different;

[0015] Ar a and Ar b are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms;

[0016] 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 40 carbon atoms;

[0017] L a , L b , 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;

[0018] L a , L b 、L1、L2、Ar a 、Ar b , the substituents in Ar1 and Ar2 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, 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 10 carbon atoms, an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 3 to 20 carbon atoms.

[0019] A second aspect of the present application provides an electronic component, 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 above-mentioned organic compound.

[0020] A third aspect of the present application provides an electronic device comprising the electronic component described in the second aspect of the present application.

[0021] The purpose of the present application is to provide a method for preparing an oxazolo[4,5-b]pyridine or thiazolo[4,5-b]pyridine A compound having a substituted pyridine as a parent nucleus and an oxazolo[4,5-b]pyridine or thiazolo[4,5-b]pyridine attached thereto has a large conjugated plane and high interatomic bond energy, which is conducive to solid-state stacking between molecules and exhibits good thermodynamic stability. In addition, the oxazolo[4,5-b]pyridine or thiazolo[4,5-b]pyridine can enhance the polarity of the compound, increase electron mobility, and facilitate charge transport. Furthermore, the structure provided by the present invention can effectively complex with metals and, when used as a charge generation layer material, can improve the efficiency of charge generation, thereby improving luminous efficiency and extending the service life of organic electroluminescent devices.

[0022] Other features and advantages of the present application will be described in detail in the subsequent detailed description. BRIEF DESCRIPTION OF THE DRAWINGS

[0023] 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.

[0024] FIG1 is a schematic structural diagram of an organic electroluminescent device according to an embodiment of the present application.

[0025] FIG2 is a schematic structural diagram of an organic electroluminescent device according to another embodiment of the present application.

[0026] FIG3 is a schematic structural diagram of an electronic device according to an embodiment of the present application.

[0027] Reference numerals

[0028] 100, anode 200, cathode 300, functional layer 310, hole injection layer

[0029] 321, hole transport layer 322, electron blocking layer 330, organic light emitting layer 340, electron transport layer

[0030] 350, electron injection layer 411, first hole transport layer 412, first hole adjustment layer 413, first light emitting layer

[0031] 414, first electron transport layer 421, n-type charge generation layer 422, p-type charge generation layer 431, second hole transport layer

[0032] 432, second hole adjustment layer 433, second light-emitting layer 434, second electron transport layer 410, first light-emitting unit

[0033] 420, charge generation layer 430, second light emitting unit 400, electronic device DETAILED DESCRIPTION

[0034] 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.

[0035] In a first aspect, the present application provides an organic compound having a structure shown in Formula I:

[0036] Where Q is

[0037] Each R1 is independently hydrogen or

[0038] Each R2 is independently hydrogen or

[0039] X1 and X2 are the same or different and are each independently selected from O or S;

[0040] m represents the number of R1, m is selected from 1, 2 or 3; when m is greater than 1, any two R1 are the same or different;

[0041] n represents the number of R2, and n is selected from 1, 2, 3 or 4; when n is greater than 1, any two R2 are the same or different;

[0042] Ar a and Ar b are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms;

[0043] 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 40 carbon atoms;

[0044] L a 、L b , 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;

[0045] L a 、L b 、L1、L2、Ar a 、Ar b , the substituents in Ar1 and Ar2 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, 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 10 carbon atoms, an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 3 to 20 carbon atoms.

[0046] 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.

[0047] 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.

[0048] 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.

[0049] 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.

[0050] 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, dibenzothiophene-substituted phenyl, pyridine-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.

[0051] In the present application, a heteroaryl group refers to a monovalent aromatic ring or a derivative thereof that includes 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 a plurality of aromatic ring systems connected by conjugated 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.

[0052] 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 cycloalkyl group, a haloalkyl group, a deuterated alkyl 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.

[0053] 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.

[0054] 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.

[0055] 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.

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

[0057] In the present application, specific examples of trialkylsilyl include, but are not limited to, trimethylsilyl, triethylsilyl, and the like.

[0058] In the present application, specific examples of the haloalkyl group include, but are not limited to, trifluoromethyl.

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

[0060] 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):

[0061] 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):

[0062] In some embodiments of the present application, Each is independently selected from the group consisting of:

[0063] In some embodiments of the present application, Each is independently selected from the group consisting of:

[0064] In some embodiments of the present application, Ar a and Ar bare the same or different and are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted anthracenyl, and substituted or unsubstituted phenanthrenyl.

[0065] In some embodiments of the present application, Ar a and Ar b The substituents in are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl, phenyl or naphthyl.

[0066] In some embodiments of the present application, Ar a and Ar b Each is independently selected from the group consisting of:

[0067] In some embodiments of the present application, Ar a and Ar b Each is independently selected from the group consisting of:

[0068] In some embodiments of the present application, Ar1 and Ar2 are the same or different and 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 5 to 28 carbon atoms. For example, Ar1 and Ar2 are the same or different and 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 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27 or 28 carbon atoms.

[0069] In some embodiments of the present application, the substituents in Ar1 and Ar2 are each independently selected from deuterium, fluorine, cyano, 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 7 carbon atoms, an aryl group having 6 to 12 carbon atoms, or a heteroaryl group having 3 to 9 carbon atoms.

[0070] In some embodiments of the present application, Ar1 and Ar2 are the same or different and are each independently selected from a substituted or unsubstituted group W, wherein the unsubstituted group W is selected from the group consisting of the following groups:

[0071] Wherein, the substituted group W has one or more substituents, and the substituents are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, phenyl, phenyl, naphthyl, biphenyl, pyridyl, quinolyl or isoquinolyl; when the number of the substituents is greater than 1, the substituents are the same or different.

[0072] In some embodiments of the present application, Ar1 and Ar2 are each independently selected from the group consisting of the following groups:

[0073] In some embodiments of the present application, Ar1 and Ar2 are each independently selected from the group consisting of the following groups:

[0074] In some embodiments of the present application, L a , L b , L1 and L2 are the same or different and are 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 3 to 20 carbon atoms. For example, L a , L b , 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, and a substituted or unsubstituted heteroarylene group having 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20 carbon atoms.

[0075] In some embodiments of the present application, L a , L b The substituents in L1 and L2 are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, an aryl group having 6 to 12 carbon atoms, or a heteroaryl group having 5 to 12 carbon atoms.

[0076] In some embodiments of the present application, L a , L b , L1 and L2 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted group U, wherein the unsubstituted group U is selected from the group consisting of the following groups:

[0077] The substituted group U has one or more substituents, each of which is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, phenyl, naphthyl, biphenyl, pyridyl, quinolyl or isoquinolyl. When the number of substituents is greater than 1, the substituents are the same or different.

[0078] In some embodiments of the present application, L a 、L b , 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:

[0079] In some embodiments of the present application, L a 、L b , 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:

[0080] In some embodiments of the present application, Selected from the group consisting of:

[0081] In some embodiments of the present application, Selected from the group consisting of:

[0082] In some embodiments of the present application, Selected from the group consisting of:

[0083] In some embodiments of the present application, Selected from the group consisting of:

[0084] In some embodiments of the present application, the organic compound has a structure shown in the following Formula II or Formula I-II:

[0085] In some embodiments of the present application, in the above formula II, each R1 is independently selected from the group consisting of hydrogen or the following groups:

[0086] Each R2 is independently selected from hydrogen or In some embodiments of the present application, in the above formula II, each R1 is independently selected from hydrogen or Each R2 is independently selected from the group consisting of hydrogen or:

[0087] In some embodiments of the present application, in the above formula I-II, R1 is selected from the group consisting of hydrogen or the following groups:

[0088] Specifically, the organic compound is selected from the group consisting of the following compounds:

[0089] In a second aspect, the present application provides an electronic component comprising an anode and a cathode arranged opposite to each other, and a functional layer arranged between the anode and the cathode; wherein the functional layer comprises the organic compound of the present application.

[0090] In one embodiment of the present application, the functional layer includes an organic hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer and an electron injection layer, and the electron transport layer includes the organic compound.

[0091] In some embodiments of the present application, the electronic component is an organic electroluminescent device.

[0092] In one embodiment, the electronic component is an organic electroluminescent device. As shown in FIG1 , the organic electroluminescent device may include a stacked anode 100 and cathode 200, and a functional layer 300 disposed between the anode 100 and cathode 200. The functional layer 300 includes a hole injection layer 310, a hole transport layer 321, a hole adjustment layer 322, a light-emitting layer 330, an electron transport layer 340, and an electron injection layer 350. The electron transport layer 340 includes the organic compound described herein.

[0093] In some embodiments of 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. Preferably, the transparent electrode comprising indium tin oxide (ITO) is used as the anode.

[0094] In some embodiments of the present application, the hole transport layer material may be selected from carbazole polymers, carbazole-linked triarylamine compounds, or other types of compounds, and this application does not make special provisions for this. For example, the hole transport layer material is selected from the group consisting of the following compounds:

[0095] In one specific embodiment, the hole transport layer 321 is HT-1.

[0096] 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. In some embodiments of the present application, the electron blocking layer 322 is composed of compound EB-1 composition.

[0097] In some embodiments of the present application, the organic light-emitting layer 330 may be composed of a single light-emitting layer material, or may include a host material and a guest material. In some embodiments of the present application, 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.

[0098] In some embodiments of the present application, the main material of the organic light-emitting layer 330 can be a metal chelate compound, a bisphenylethylene derivative, an aromatic amine derivative, a dibenzofuran derivative or other types of materials, and the present application does not impose any special restrictions on this. The main material can 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

[0099] The guest material of the organic light-emitting layer 330 can be selected with reference to the prior art, for example, it can be selected from iridium (III) organometallic complexes, platinum (II) organometallic complexes, ruthenium (II) complexes, etc. Specific examples of the guest material include, but are not limited to,

[0100] In one embodiment of the present application, the guest material of the organic light emitting layer 330 is BD-1

[0101] In some embodiments of the present application, the electron transport layer 340 can be a single-layer structure or a multi-layer structure, which can include one or more electron transport materials. According to the embodiment of the present application, the electron transport material includes the compound provided in the present application. In addition, the electron transport material can generally also include a metal complex and / or a nitrogen-containing heterocyclic derivative, wherein the metal complex material can be selected from LiQ, Alq3, etc.; the nitrogen-containing heterocyclic derivative can be an aromatic ring having a nitrogen-containing six-membered ring or five-membered ring skeleton, a fused aromatic ring compound having a nitrogen-containing six-membered ring or five-membered ring skeleton, etc. Specific examples include but are not limited to 1,10-phenanthroline compounds such as Bphen, NBphen, ET-21, BimiBphen, or anthracene compounds, triazines or pyrimidine compounds containing hetero-nitrogen aromatic groups as shown below. In one embodiment of the present application, the electron transport layer 340 includes ET-1 and LiQ. In one embodiment of the present application, the electron transport layer 340 includes the compound provided in the present application and LiQ.

[0102] 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. A metal electrode comprising magnesium and silver is preferred as the cathode.

[0103] In some embodiments of the present application, as shown in FIG1 , 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. For example, the compound contained in the hole injection layer 310 is selected from the group consisting of the following compounds:

[0104] In a specific embodiment of the present application, the hole injection layer 310 is HT-1 and NDP-9.

[0105] In some embodiments of the present application, as shown in FIG1 , 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 compound. For example, the electron injection layer 350 includes Yb.

[0106] 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 charge-generating layer, and a second light-emitting unit. The charge-generating layer includes the organic compound described in the present application. The organic electroluminescent device shown in Figure 2 is hereinafter also referred to as a stacked organic electroluminescent device.

[0107] In one embodiment of the present application, a stacked organic electroluminescent device 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, and 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 includes the organic compound described in the present application.

[0108] 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.

[0109] 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.

[0110] In one embodiment of the present application, the n-type charge generation layer is composed of the organic compound described herein and a metal doping material. In some embodiments, the metal doping material is Li, Ca, Ag, Cs, or Yb.

[0111] In one embodiment of the present application, the P-type charge generation layer includes HT-1 and NDP-9.

[0112] In the present application, the anode 100 includes an anode material. Optionally, the anode material includes indium tin oxide (ITO).

[0113] In one embodiment of the present application, the hole injection layer 310 is composed of compound HT-1 and compound NDP-9.

[0114] In one embodiment of the present application, the first hole transport layer 411 and the second hole transport layer 431 include HT-1.

[0115] In one embodiment of the present application, the first hole adjustment layer 412 and the second hole adjustment layer 432 include RP-1

[0116] In the present application, the first light-emitting layer of the first light-emitting unit and the second light-emitting layer of the second light-emitting unit may each include the same or different host materials and the same or different guest materials.

[0117] In a specific embodiment of the present application, the main material of the first light-emitting layer 413 and the second light-emitting layer 433 is RH-1

[0118] In a specific embodiment of the present application, the guest material of the first light-emitting layer 413 and the second light-emitting layer 433 is RD-1

[0119] In a specific embodiment of the present application, the first electron transport layer 414 and the second electron transport layer 434 include ET-1.

[0120] In one embodiment of the present application, the electron injection layer 350 includes Yb.

[0121] In a specific embodiment of the present application, the cathode 200 includes a cathode material including magnesium and silver.

[0122] In a third aspect, the present application provides an electronic device comprising the electronic component provided in the second aspect of the present application.

[0123] According to one embodiment, as shown in FIG3 , the electronic device is a first electronic device 400, which includes the organic electroluminescent device described above. The first 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, and the like.

[0124] The synthesis method of the organic compound of the present application is specifically described below with reference to synthesis examples, but the present application is not limited thereto.

[0125] The compounds whose synthesis methods are not mentioned in this application are all raw materials obtained through commercial channels.

[0126] Synthesis example

[0127] 1. Synthesis of intermediate IM A-1

[0128] 4-Chloro-2,6-bispinacolatoyl ester pyridine (20 g, 54.7 mmol) and 2-bromo-6-phenylpyridine (12.8 g, 54.7 mmol) were dissolved in 120 mL of toluene. Tetrakis(triphenylphosphine)palladium (0.64 g, 0.55 mmol), K2CO3 (11.3 g, 82.1 mmol), 60 mL of ethanol, and 20 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 recrystallized from dichloromethane:n-heptane = 1:3 (v / v) to afford Intermediate IM A-1 (10.5 g, 49% yield).

[0129] The intermediates IM Ax (x is 2 to 4) shown in Table 1 were synthesized by the same method as for the intermediate IM A-1, except that raw material 1 was used instead of 4-chloro-2,6-bispinacolato ester pyridine, and raw material 2 was used instead of 2-bromo-6-phenylpyridine. The main raw materials used, the synthesized intermediates, and their yields are shown in Table 1.

[0130] Table 1

[0131] 2. Synthesis of intermediate IM Bx

[0132] The intermediates IM Bx (x is 1 to 9) shown in Table 2 were synthesized by the same method as for the intermediate IM A-1, except that the raw material 3 was used instead of 2-bromo-6-phenylpyridine, and the raw material 4 was used instead of 4-chloro-2,6-bispinacolato ester pyridine. The main raw materials used, the synthesized intermediates, and their yields are shown in Table 2.

[0133] Table 2

[0134] 3. Synthesis of intermediate IM B-3

[0135] 4-Chloro-2,6-bispinacolatoyl ester pyridine (20 g, 54.7 mmol) and 5-bromo-2-benzoxazolo[4,5-b]pyridine (33.11 g, 120.34 mmol) were dissolved in 120 mL of toluene. Tetrakis(triphenylphosphine)palladium (0.128 g, 1.10 mmol), K2CO3 (22.6 g, 164.2 mmol), 60 mL of ethanol, and 20 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 recrystallized from dichloromethane:n-heptane = 1:3 (v / v) to afford Intermediate IM B-3 (14 g, 51% yield).

[0136] Intermediate IM B-9 shown in Table 3 was synthesized by the same method as intermediate IM B-3, except that raw material 5 was used instead of 5-bromo-2-benzoxazolo[4,5-b]pyridine. The main raw materials used, the synthesized intermediates and their yields are shown in Table 3.

[0137] Table 3

[0138] Synthesis Example 1: Synthesis of Compound 1

[0139] Intermediate IM B-1 (5 g, 10.8 mmol) and 4-biphenylboronic acid (2.6 g, 13.1 mmol) were dissolved in 30 mL of toluene. Tetrakis(triphenylphosphine)palladium (0.13 g, 0.11 mmol), K2CO3 (3.0 g, 21.7 mmol), 10 mL of ethanol, and 5 mL of water were added. The mixture was heated under reflux for 8 h under a nitrogen atmosphere. After cooling to room temperature, 100 mL of water was added and stirred for 30 min. The solid was collected by suction filtration and rinsed with 100 mL of ethanol. This was repeated three times. The obtained solid was recrystallized from dichloromethane to obtain compound 1 (3.9 g, yield 62%). Mass spectrum (m / z) = 579.21 [M+H] + .

[0140] Compound X shown in Table 4 was synthesized in the same manner as compound 1, except that starting material 6 was used instead of IM B-1, and starting material 7 was used instead of 4-biphenylboronic acid. The main starting materials used, the synthesized compounds, their yields, and their mass spectra are shown in Table 4.

[0141] Table 4

[0142] NMR data of some compounds:

[0143] Compound 1

[0144] 1 H-NMR(CD3Cl,400MHz):8.77(d,2H),8.59-8.56(m,2H),8.34(d,2H),8.26(d,2H),8.06(d ,1H),7.91(t,3H),7.82(d,1H),7.72-7.63(m,4H),7.54-7.50(m,6H),7.46-7.36(m,3H).

[0145] Compound 66

[0146] 1 H-NMR(CD3Cl,400MHz):8.82-8.74(m,7H),8.59-8.51(m,4H),8.34(d,2H), 8.07-8.02(m,5H),7.89-7.85(m,3H),7.67-7.63(m,2H),7.46-7.36(m,4H).

[0147] Example of fabrication and evaluation of organic electroluminescent devices

[0148] Example 1: Blue organic electroluminescent device

[0149] 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 ITO substrate was cleaned with an organic solvent to remove impurities and oil stains on the surface of the ITO substrate.

[0150] On the experimental substrate (anode), compound HT-1 and compound NDP-9 were co-evaporated at an evaporation rate ratio of 98:2 to form a layer with a thickness of hole injection layer.

[0151] On the hole injection layer, compound HT-1 was vacuum-deposited to form a layer with a thickness of hole transport layer.

[0152] On the hole transport layer, compound EB-1 was vacuum evaporated to form a layer with a thickness of electron blocking layer.

[0153] 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.

[0154] On the organic light-emitting layer, compound 63 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 co-evaporated on the electron injection layer at an evaporation rate ratio of 1:9 to form a layer with a thickness of cathode.

[0155] In addition, compound CP-1 was 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.

[0156] Example 2 to Example 14

[0157] An organic electroluminescent device was prepared by the same method as in Example 1, except that the compound in Table 5 was used instead of Compound 63 in Example when forming the electron transport layer.

[0158] Comparative Example 1 to Comparative Example 3

[0159] 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 63 in Example 1 when forming the electron transport layer.

[0160] The main material structures used in the above embodiments and comparative examples are as follows:

[0161] The performance of the blue organic electroluminescent devices prepared in Examples 1 to 14 and Comparative Examples 1 to 3 was tested. Specifically, at 10 mA / cm 2 The IVL performance (driving voltage, current efficiency) of the device was tested under the conditions of T 95 Device life at 15mA / cm 2 The test was carried out under the conditions of , and the test results are shown in the following Table 5:

[0162] Table 5

[0163] As shown in Table 5 above, the current efficiency of Examples 1-14 using the compounds of the present invention as electron transport layer materials is improved by at least 11.7% compared with Comparative Examples 1-3. 95 The life span is increased by at least 12.6%. It can be seen that the use of the organic compound of the present application in the electron transport layer of the organic electroluminescent device can improve the current efficiency and T 95 life.

[0164] In order to further illustrate the application of the compound of the present invention as a charge generation layer in an organic electroluminescent device, the performance of the material of the present invention is studied by constructing a stacked device.

[0165] Example 15: Red stacked organic electroluminescent device

[0166] 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 cathode, 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 ITO substrate was cleaned with an organic solvent to remove impurities and oil stains on the surface of the ITO substrate.

[0167] On the experimental substrate (anode), compound HT-1 and compound NDP-9 were co-evaporated at an evaporation rate ratio of 98%:2% to form a film with a thickness of hole injection layer.

[0168] Preparation of the first light-emitting unit

[0169] On the hole injection layer, compound HT-1 was vacuum-deposited to form a layer with a thickness of On the first hole transport layer, compound RP-1 is vacuum evaporated to form a first hole transport layer with a thickness of The first hole adjustment layer.

[0170] 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.

[0171] 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 layer with a thickness of The first electron transport layer is formed. Thus, the first light-emitting unit is prepared.

[0172] Preparation of charge generation layer (CGL)

[0173] On the first electron transport layer, compound 1 and Yb were co-evaporated at an evaporation rate ratio of 99:1 to form a layer with a thickness of Then, compound HT-1 and compound NDP-9 were co-evaporated on the n-type charge generation layer at an evaporation rate ratio of 95:5 to form a layer with a thickness of p-type charge generation layer.

[0174] 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.

[0175] 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.

[0176] 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.

[0177] 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 layer with a thickness of The second electron transport layer is thus prepared.

[0178] Yb is evaporated on the second electron transport layer to form a layer with 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 thickness of cathode.

[0179] In addition, compound CP-1 was 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.

[0180] Example 16-Example 51:

[0181] An organic electroluminescent device was prepared by the same method as in Example 15, except that the compounds in Table 6 were used instead of Compound 1 in Example 15 when preparing the n-type charge generation layer.

[0182] Comparative Example 4-Comparative Example 6

[0183] An organic electroluminescent device was prepared by the same method as in Example 15, except that Compound D, Compound E and Compound F were used instead of Compound 1 in Example 15 when preparing the n-type charge generation layer.

[0184] The main material structures used in the above embodiments and comparative examples are as follows:

[0185] The performance of the red stacked organic electroluminescent devices prepared in Examples 15 to 51 and Comparative Examples 4 to 6 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 30mA / cm 2 The test was carried out under the conditions of , and the test results are shown in Table 6 below.

[0186] Table 6

[0187] As shown in Table 6 above, in Examples 15 to 51, the compounds of the present invention are used as n-type charge generation layer materials. Compared with Comparative Examples 4 to 6, the current efficiency is improved by at least 11.4%. 95 The lifespan is increased by at least 13.4%. It can be seen that using the organic compound of the present application in the n-type charge generation layer of an organic electroluminescent device can significantly improve the luminous efficiency and device lifespan of the organic electroluminescent device.

[0188] The preferred embodiments of the present invention are described in detail above in conjunction with the accompanying drawings. However, the present invention is not limited to the specific details in the above embodiments. Within the technical concept of the present invention, various simple modifications can be made to the technical solution of the present invention, and these simple modifications all fall within the scope of protection of the present invention.

Claims

1. An organic compound having the structure shown in Formula I: in, Q is Each R1 is independently hydrogen or Each R2 is independently hydrogen or X1 and X2 are the same or different and are each independently selected from O or S; m represents the number of R1, m is selected from 1, 2 or 3; when m is greater than 1, any two R1 are the same or different; n represents the number of R2, and n is selected from 1, 2, 3 or 4; when n is greater than 1, any two R2 are the same or different; Ar a and Ar b are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 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 40 carbon atoms; L a 、L b , 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; L a 、L b 、L1、L2、Ar a 、Ar b , the substituents in Ar1 and Ar2 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, 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 10 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 Ar a and Ar b are the same or different and are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl; Optionally, Ar a and Ar b The substituents in are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl, phenyl or naphthyl.

3. The organic compound according to claim 1, wherein Ar a and Ar b Each is independently selected from the group consisting of:

4. The organic compound according to claim 1, wherein Ar1 and Ar2 are the same or different and are each independently selected from a substituted or unsubstituted group W, wherein the unsubstituted group W is selected from the group consisting of the following groups: Wherein, the substituted group W has one or more substituents, and the substituents are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, phenyl, phenyl, naphthyl, biphenyl, pyridyl, quinolyl or isoquinolyl; when the number of the substituents is greater than 1, the substituents are the same or different.

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

6. The organic compound according to claim 1, wherein L a 、L b , L1 and L2 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted group U, wherein the unsubstituted group U is selected from the group consisting of the following groups: The substituted group U has one or more substituents, each of which is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, phenyl, naphthyl, biphenyl, pyridyl, quinolyl or isoquinolyl. When the number of substituents is greater than 1, the substituents are the same or different.

7. The organic compound according to claim 1, wherein L a , L b , 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:

8. The organic compound according to claim 1, wherein Selected from the group consisting of:

9. The organic compound according to claim 1, wherein Selected from the group consisting of:

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

11. An organic electroluminescent device comprising an anode and a cathode, and a functional layer disposed between the anode and the cathode; wherein: The functional layer comprises the organic compound according to any one of claims 1 to 10; Optionally, the functional layer comprises an electron transport layer, and the electron transport layer comprises the organic compound according to any one of claims 1 to 10; Optionally, 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 according to any one of claims 1 to 10.

12. An electronic device comprising the organic electroluminescent device according to claim 11.

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