Organic compounds and electronic components and devices containing them

Abstract

This application relates to an organic compound and electronic components and devices comprising the same. The organic compound of this application has the structural formula shown in Formula 1. Applying this organic compound to an organic electroluminescent device can significantly improve the device's performance.

Description

Technical Field

[0001] This application belongs to the field of organic materials technology, and in particular relates to an organic compound and electronic components and devices containing the same. Background Technology

[0002] With the development of electronic technology and the advancement of materials science, electronic components used to achieve electroluminescence or photoelectric conversion are finding increasingly wider applications. These electronic components typically include a cathode and an anode positioned opposite each other, and a functional layer disposed between the cathode and anode. This functional layer consists of multiple organic or inorganic film layers and generally includes an energy conversion layer, a hole transport layer located between the energy conversion layer and the anode, and an electron transport layer located between the energy conversion layer and the cathode.

[0003] For example, when the electronic component is an organic electroluminescent device, it generally includes an anode, a hole transport layer, an electroluminescent layer as an energy conversion layer, an electron transport layer, and a cathode stacked sequentially. When a voltage is applied to the anode and cathode, an electric field is generated between the two electrodes. Under the influence of the electric field, electrons on the cathode side move towards the electroluminescent layer, and holes on the anode side also move towards the electroluminescent 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.

[0004] Typically, electron transport materials have poor stability and low transport efficiency. When used in organic electroluminescent devices, they cannot truly balance hole-electron transport, resulting in reduced device luminous efficiency and shortened lifespan.

[0005] Currently, although a large number of high-performance organic electroluminescent materials have been developed, it is still necessary to continue to develop new materials to further improve the performance of electronic components. Summary of the Invention

[0006] In view of the above-mentioned problems existing in the prior art, the purpose of this application is to provide an organic compound and electronic components and devices containing the same, wherein the organic compound can improve the performance of electronic components and devices, such as improving device efficiency and lifespan.

[0007] To achieve the above-mentioned objectives, this application adopts the following technical solution:

[0008] According to a first aspect of this application, an organic compound is provided having a structure as represented by Formula 1:

[0009]

[0010] Ar3 is a substituted or unsubstituted aryl group with 6-12 carbon atoms;

[0011] The substituents in Ar3 may be the same or different, and are independently selected from deuterium, halogen groups, cyano groups, alkyl groups or phenyl groups having 1-5 carbon atoms;

[0012] X1, X2, and X3 represent C(H) or N atoms, and at least one of X1, X2, and X3 is an N atom;

[0013] L, L1, and L2 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted aryl groups with 6-30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 5-30 carbon atoms.

[0014] Ar1 and Ar2 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups with 6-30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 5-30 carbon atoms.

[0015] The substituents in L, L1, L2, Ar1, and Ar2 may be the same or different, and are each independently selected from deuterium, halogen groups, cyano, alkyl groups with 1-10 carbon atoms, haloalkyl groups with 1-10 carbon atoms, deuteralkyl groups with 1-10 carbon atoms, trialkylsilyl groups with 3-12 carbon atoms, aryl groups with 6-20 carbon atoms, heteroaryl groups with 5-15 carbon atoms, or cycloalkyl groups with 3-10 carbon atoms;

[0016] Optionally, any two adjacent substituents in Ar1 and Ar2 form a ring;

[0017] R1 and R2 may be the same or different, and each is independently selected from deuterium, halogen group, cyano, alkyl with 1-10 carbon atoms, haloalkyl with 1-10 carbon atoms, deuterated alkyl with 1-10 carbon atoms, and aryl with 6-20 carbon atoms.

[0018] n1 represents the number of R1s, and is selected from 0, 1, 2, 3 or 4; when n1 is greater than 1, any two R1s are the same or different.

[0019] n2 represents the number of R2s, and is selected from 0, 1, 2 or 3; when n2 is greater than 1, any two R2s are the same or different.

[0020] According to a second aspect of this application, an electronic component is provided, comprising an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer comprising the aforementioned organic compound.

[0021] According to a third aspect of this application, an electronic device is provided, comprising the electronic components described in the second aspect.

[0022] The organic compounds of this application are composed of aryl-substituted adamantane groups and triazine groups. Generally, adamantane has excellent sublimation properties due to its large steric dimensionality and robustness, and has a stable chemical structure, thus exhibiting excellent thermal stability. The hydrogen on the aryl-substituted adamantane can saturate the substituted carbon, further enhancing its stability. Combined with triazine groups, it can significantly improve device efficiency and lifespan.

[0023] Other features and advantages of this application will be described in detail in the following detailed description section. Attached Figure Description

[0024] The accompanying drawings are provided to further understand this application and form part of the specification. They are used together with the following detailed description to explain this application, but do not constitute a limitation thereof.

[0025] Figure 1 This is a schematic diagram of the structure of an organic electroluminescent device according to this application.

[0026] Figure 2 This is a schematic diagram of the structure of an electronic device according to this application.

[0027] Figure Labels

[0028] 100, Anode 200, Cathode 300, Functional Layer 310, Hole Injection Layer

[0029] 320, Hole transport layer; 330, Electron blocking layer; 340, Organic light-emitting layer; 350, Electron transport layer

[0030] 360°, electron injection layer 400°, electronic device Detailed Implementation

[0031] Exemplary embodiments will now be described more fully with reference to the accompanying drawings. However, exemplary embodiments can be implemented in many forms and should not be construed as limited to the examples set forth herein; rather, these embodiments are provided so that this application will be more comprehensive and complete, and will fully convey the concept of exemplary embodiments to those skilled in the art. The described features, structures, or characteristics may be combined in any suitable manner in one or more embodiments. In the following description, numerous specific details are provided to give a full understanding of embodiments of this application.

[0032] In a first aspect, this application provides an organic compound having a structure as represented by Formula 1:

[0033]

[0034] Ar3 is a substituted or unsubstituted aryl group with 6-12 carbon atoms;

[0035] The substituents in Ar3 may be the same or different, and are independently selected from deuterium, halogen groups, cyano groups, alkyl groups or phenyl groups having 1-5 carbon atoms;

[0036] X1, X2, and X3 represent C(H) or N atoms, and at least one of X1, X2, and X3 is an N atom;

[0037] L, L1, and L2 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted aryl groups with 6-30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 5-30 carbon atoms.

[0038] Ar1 and Ar2 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups with 6-30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 5-30 carbon atoms.

[0039] The substituents in L, L1, L2, Ar1, and Ar2 may be the same or different, and are each independently selected from deuterium, halogen groups, cyano, alkyl groups with 1-10 carbon atoms, haloalkyl groups with 1-10 carbon atoms, deuteralkyl groups with 1-10 carbon atoms, trialkylsilyl groups with 3-12 carbon atoms, aryl groups with 6-20 carbon atoms, heteroaryl groups with 5-15 carbon atoms, or cycloalkyl groups with 3-10 carbon atoms;

[0040] Optionally, any two adjacent substituents in Ar1 and Ar2 form a ring;

[0041] R1 and R2 may be the same or different, and each is independently selected from deuterium, halogen group, cyano, alkyl with 1-10 carbon atoms, haloalkyl with 1-10 carbon atoms, deuterated alkyl with 1-10 carbon atoms, and aryl with 6-20 carbon atoms.

[0042] n1 represents the number of R1s, and is selected from 0, 1, 2, 3 or 4; when n1 is greater than 1, any two R1s are the same or different.

[0043] n2 represents the number of R2s, and is selected from 0, 1, 2 or 3; when n2 is greater than 1, any two R2s are the same or different.

[0044] In this application, the fluorene group can be replaced by one or two substituents. Specifically, when the fluorene group is replaced, the substitution can be: etc., but not limited to this.

[0045] In this application, the descriptive phrases "each...independently is," "...each independently is," and "...each independently selected from" are interchangeable and should be interpreted broadly. They can mean either that the specific options expressed by the same symbol in different groups do not affect each other, or that the specific options expressed by the same symbol in the same group do not affect each other. For example, " In this formula, each q is independently 0, 1, 2 or 3, and each R is independently selected from hydrogen, deuterium, fluorine or chlorine. The meaning is as follows: Formula Q-1 indicates that there are q substituents R on the benzene ring. Each R can be the same or different, and the options of each R do not affect each other. Formula Q-2 indicates that there are q substituents R on each benzene ring of biphenyl. The number q of substituents R on the two benzene rings can be the same or different, and each R can be the same or different. The options of each R do not affect each other.

[0046] In this application, the term "substituted or unsubstituted" means that the functional group described after the term may or may not have substituents (hereinafter, for ease of description, substituents are collectively referred to as Rc). For example, "substituted or unsubstituted aryl" refers to an aryl group having a substituent Rc or an unsubstituted aryl group. The aforementioned substituents, i.e., Rc, can be, for example, deuterium, halogen groups, cyano, heteroaryl, aryl, trialkylsilyl, alkyl, haloalkyl, deuterylalkyl, cycloalkyl, etc.

[0047] In this application, the number of carbon atoms in substituted or unsubstituted functional groups refers to the total number of carbon atoms. For example, if L1 is a substituted arylene with 12 carbon atoms, then the total number of carbon atoms in the arylene and its substituents is 12.

[0048] In this application, aryl refers to any optional functional group or substituent derived from an aromatic carbon ring. An aryl group can be a monocyclic aryl (e.g., phenyl) or a polycyclic aryl; in other words, an aryl group can be a monocyclic aryl, a fused-ring aryl, two or more monocyclic aryl groups conjugated by carbon-carbon bonds, a monocyclic aryl and a fused-ring aryl group conjugated by carbon-carbon bonds, or two or more fused-ring aryl groups conjugated by carbon-carbon bonds. That is, unless otherwise stated, two or more aromatic groups conjugated by carbon-carbon bonds can also be considered as aryl groups in this application. Fused-ring aryl groups may include, for example, bicyclic fused aryl (e.g., naphthyl), tricyclic fused aryl (e.g., phenanthrene, fluorene, anthracene), etc. The aryl group does not contain heteroatoms such as B, N, O, S, P, Se, and Si. Examples of aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, anthraceneyl, phenanthryl, biphenyl, terphenyl, benzo[9,10]phenanthryl, pyrene, benzofluoranthraceneyl, etc. Aryl, spirodifluorenyl, etc. In this application, the aryl group refers to a divalent group formed by the further loss of a hydrogen atom from an aryl group.

[0049] In this application, terphenyl includes

[0050] In this application, the substituted aryl group can be one or more hydrogen atoms of the aryl group that are replaced by groups such as deuterium atoms, halogen groups, cyano groups, aryl groups, heteroaryl groups, alkyl groups, cycloalkyl groups, etc. It should be understood that the number of carbon atoms in the substituted aryl group refers to the total number of carbon atoms of the aryl group and the substituents on the aryl group. For example, a substituted aryl group with 18 carbon atoms means that the total number of carbon atoms of the aryl group and the substituents is 18.

[0051] In this application, a heteroaryl group refers to a monovalent aromatic ring or its derivative containing 1, 2, 3, 4, 5, 6, or 7 heteroatoms. The heteroatoms can be at least one 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 system of multiple aromatic rings connected by carbon-carbon bonds in a conjugated manner. Each aromatic ring system can be an aromatic monocyclic ring or an aromatic fused ring. For example, heteroaryl groups may include, but are not limited to, thiopheneyl, furanyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridineyl, pyridazinyl, quinolinyl, quinazolinyl, quinoxazinyl, phenothiazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, isoquinolinyl, indolyl, carbazoleyl, benzoxazolyl, benzoimidazolyl, benzothiazolyl, benzocarbazoleyl, benzothiaphenyl, dibenzothiaphenyl, thiaphenothiaphenyl, benzofuranyl, phenanthrololinyl, isoxazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, silfluorenyl, dibenzofuranyl, and N-phenylcarbazoleyl, N-pyridylcarbazoleyl, N-methylcarbazoleyl, etc. Among them, thienyl, furanyl, and phenanthroline are heteroaryl groups of the single aromatic ring type, while N-phenylcarbazoyl and N-pyridylcarbazoyl are heteroaryl groups of the polycyclic system type connected by carbon-carbon bonds. In this application, the hypoaryl group refers to the divalent group formed by the further loss of a hydrogen atom from a heteroaryl group.

[0052] In this application, the substituted heteroaryl group may be one or more hydrogen atoms of the heteroaryl group that are replaced by groups such as deuterium atoms, halogen groups, cyano groups, aryl groups, heteroaryl groups, alkyl groups, cycloalkyl groups, etc. It should be understood that the number of carbon atoms in the substituted heteroaryl group refers to the total number of carbon atoms of the heteroaryl group and the substituents on the heteroaryl group.

[0053] In this application, the number of carbon atoms in the substituted or unsubstituted aryl group can be 6-25, for example, the number of carbon atoms can be 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, or 25.

[0054] In this application, specific examples of aryl groups as substituents include, but are not limited to, phenyl, biphenyl, naphthyl, fluorenyl, phenanthryl, anthracene, etc. base.

[0055] In this application, the number of carbon atoms in the substituted or unsubstituted heteroaryl group can be 12-20, for example, the number of carbon atoms can be 12, 13, 14, 15, 16, 17, 18, 19, or 20.

[0056] In this application, specific examples of heteroaryl groups as substituents include, but are not limited to, triazinyl, pyridinyl, pyrimidinyl, carbazolyl, dibenzofuranyl, dibenzothiopheneyl, quinolinyl, quinazolinyl, quinoxalinyl, isoquinolinyl, carbazolyl, and N-phenylcarbazolyl.

[0057] In this application, the non-positioned linker refers to a single bond extending from the ring system. This means that one end of the linking bond can connect to any position in the ring system that the bond passes through, and the other end connects to the rest of the compound molecule.

[0058] In this application, alkyl groups having 1-10 carbon atoms can include straight-chain alkyl groups having 1-10 carbon atoms and branched alkyl groups having 3-10 carbon atoms. The number of carbon atoms in an alkyl group can be, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10. Specific examples of alkyl groups include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, n-octyl, 2-ethylhexyl, nonyl, decyl, and 3,7-dimethyloctyl.

[0059] In this application, the halogen group may be, for example, fluorine, chlorine, bromine, or iodine.

[0060] In this application, the number of carbon atoms in cycloalkyl groups with 3-10 carbon atoms can be, for example, 3, 4, 5, 6, 7, 8, or 10. Specific examples of cycloalkyl groups include, but are not limited to, cyclopentyl and cyclohexyl.

[0061] For example, as shown in equation (f) below, the naphthyl group represented by equation (f) is connected to other positions in the molecule by two non-positional linkages that span the bicyclic ring, which means that any possible connection mode is shown as in equations (f-1) to (f-10).

[0062]

[0063] For another example, as shown in the following formula (X'), the dibenzofuran group represented by formula (X') is connected to other positions of the molecule by a non-positional linker extending from the middle of one side of the benzene ring. This means that any possible connection mode shown in formulas (X'-1) to (X'-4) is included.

[0064]

[0065] In some embodiments of this application, X1 is N, and X2 and X3 are C(H); or X2 is N, and X1 and X3 are C(H); or X3 is N, and X1 and X2 are C(H).

[0066] In some embodiments of this application, X1 and X2 are N, and X3 is C(H); or X1 and X3 are N, and X2 is C(H); or X2 and X3 are N, and X1 is C(H).

[0067] In some embodiments of this application, X1, X2 and X3 are all N.

[0068] In some embodiments of this application, the organic compound has the structure shown in Formula 1-A, Formula 1-B, Formula 1-C, or Formula 1-D:

[0069]

[0070] In some embodiments of this application, Ar1 and Ar2 are each independently selected from substituted or unsubstituted aryl groups having 6-25 carbon atoms and substituted or unsubstituted heteroaryl groups having 12-20 carbon atoms.

[0071] Optionally, Ar1 and Ar2 are each independently selected from substituted or unsubstituted aryl groups having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, or 25 carbon atoms, and substituted or unsubstituted heteroaryl groups having 12, 13, 14, 15, 16, 17, 18, 19, or 20 carbon atoms.

[0072] Optionally, the substituents in Ar1 and Ar2 may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, alkyl with 1-5 carbon atoms, trimethylsilyl, trifluoromethyl or aryl with 6-12 carbon atoms;

[0073] Optionally, any two adjacent substituents in Ar1 form a saturated or unsaturated 5-13 membered ring;

[0074] Optionally, any two adjacent substituents in Ar2 form a saturated or unsaturated 5-13 membered ring.

[0075] In other embodiments of this application, Ar1 and Ar2 are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted phenanthrene, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, or substituted or unsubstituted carbazoleyl.

[0076] Optionally, the substituents in Ar1 and Ar2 are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trimethylsilyl, trifluoromethyl, phenyl, naphthyl, or biphenyl.

[0077] Optionally, any two adjacent substituents in Ar1 and Ar2 can form cyclohexane. Cyclopentane Benzene ring, naphthalene ring or fluorene ring

[0078] In some embodiments of this application, Ar1 and Ar2 are each independently selected from substituted or unsubstituted groups W, wherein the unsubstituted group W is selected from the following groups:

[0079]

[0080] Wherein, the substituted group W has one or more substituents, wherein the substituents are independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trimethylsilyl or phenyl, and when the number of substituents is greater than 1, the substituents may be the same or different.

[0081] Alternatively, Ar1 and Ar2 are each independently selected from the group consisting of:

[0082]

[0083] In some specific embodiments, Ar1 and Ar2 are each independently selected from the following groups:

[0084]

[0085]

[0086] In some embodiments of this application, Ar3 is selected from phenyl, monodeuterated phenyl, dideuterated phenyl, trideuterated phenyl, tetradeuterated phenyl, or pentadeuterated phenyl.

[0087] Specifically, Ar3 is selected from

[0088] In some embodiments of this application, L, L1, and L2 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted aryl groups with 6-20 carbon atoms, and substituted or unsubstituted heteroaryl groups with 12-20 carbon atoms.

[0089] Optionally, L, L1, and L2 may be the same or different, each independently selected from single bonds, substituted or unsubstituted aryl groups with 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20 carbon atoms, and substituted or unsubstituted heteroaryl groups with 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20 carbon atoms.

[0090] Optionally, the substituents in L, L1 and L2 may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, alkyl or phenyl with 1-5 carbon atoms.

[0091] Optionally, L, L1, and L2 may be the same or different, and each may be independently selected from single bonds, substituted or unsubstituted aryl groups with 6-15 carbon atoms, or substituted or unsubstituted heteroaryl groups with 12-18 carbon atoms.

[0092] Further optionally, L is selected from a single bond or a substituted or unsubstituted aryl group having 6-15 carbon atoms.

[0093] Optionally, L, L1, and L2 may be the same or different, and each may be independently selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted anthracene, substituted or unsubstituted phenanthrene, substituted or unsubstituted fluorene, or substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, or substituted or unsubstituted carbazolyl.

[0094] Optionally, the substituents in L, L1 and L2 may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl or phenyl.

[0095] Further optionally, L is selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, or a substituted or unsubstituted fluorene.

[0096] Further optionally, L1 and L2 may be the same or different, and each may be independently selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted phenanthylene, substituted or unsubstituted anthracene, substituted or unsubstituted fluorene, or substituted or unsubstituted dibenzofuranyl.

[0097] In some embodiments of this application, L, L1, and L2 may be the same or different, and each is independently selected from single-bonded, substituted, or unsubstituted groups Q; wherein, the unsubstituted group Q is selected from the group consisting of:

[0098]

[0099] Wherein, the substituted group Q has one or more substituents, wherein the substituents are independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl or phenyl, and when the number of substituents is greater than 1, the substituents may be the same or different.

[0100] Optionally, L, L1, and L2 may be the same or different, and each may be independently selected from the group consisting of single bonds or the following groups:

[0101]

[0102] Further, optionally, L is selected from a single bond or the following groups:

[0103]

[0104] Alternatively, L1 and L2 may each be independently selected from single bonds or the following groups:

[0105]

[0106] In some embodiments of this application, Each group is independently selected from the group consisting of the following groups:

[0107]

[0108] Specifically, Each group is independently selected from the group consisting of the following groups:

[0109]

[0110] In some embodiments of this application, R1 and R2 are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, or phenyl.

[0111] In some embodiments of this application, n1 and n2 may be the same or different, and are independently selected from 0 or 1.

[0112] Optionally, the organic compound is selected from the group consisting of:

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124] Secondly, this application provides an electronic component, including an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer contains the organic compound of this application.

[0125] Optionally, the electronic component is an organic electroluminescent device.

[0126] In some embodiments of this application, the electronic component is an organic electroluminescent device. For example... Figure 1 As shown, an organic electroluminescent device may include an anode 100, a hole transport layer 320, an electron blocking layer 330, an organic light-emitting layer 340, an electron transport layer 350, and a cathode 200, which are stacked sequentially.

[0127] In some specific embodiments of this application, the organic electroluminescent device is a blue organic electroluminescent device.

[0128] Optionally, the anode 100 includes an anode material that is preferably a material with a large work function that facilitates hole injection into the functional layer. Specific examples of anode materials include: metals such as nickel, platinum, vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; or conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, and polyaniline, but are not limited thereto. Preferably, indium tin oxide (ITO) is included as the transparent electrode for the anode.

[0129] Optionally, the hole transport layer 320 includes one or more hole transport materials, which may be selected from carbazole polymers, carbazole-linked triarylamine compounds, or other types of compounds. Those skilled in the art can make selections by referring to the prior art.

[0130] In one specific implementation, the hole transport layer 320 is PAPB.

[0131] Optionally, the electron blocking layer 330 comprises one or more electron blocking materials, which may be selected from carbazole polymers or other types of compounds, and this application does not impose any special limitations on them. For example, the material of the electron blocking layer 330 is selected from the group consisting of the following compounds:

[0132]

[0133]

[0134] In some embodiments of this application, the electron blocking layer 330 is HT-17.

[0135] Optionally, a hole injection layer 310 may be provided between the anode 100 and the hole transport layer 320 to enhance the ability to inject holes into the hole transport layer 320. The hole injection layer 310 may be selected from benzidine derivatives, starburst-like aryl amine compounds, phthalocyanine derivatives, or other materials; this application does not impose any special limitations on this. The material of the hole injection layer 310 may, for example, be selected from the following compounds or any combination thereof;

[0136]

[0137] In some embodiments of this application, the hole injection layer 310 is composed of HI-01 and PAPB.

[0138] Optionally, the organic light-emitting layer 340 may be composed of a single light-emitting layer material, or it may include a host material and a dopant material. Optionally, the organic light-emitting layer 340 is composed of a host material and a dopant material. Holes and electrons injected into the organic light-emitting layer 340 can recombine in the organic light-emitting layer 340 to form excitons. The excitons transfer energy to the host material, and the host material transfers energy to the dopant material, thereby enabling the dopant material to emit light.

[0139] The main material of the organic light-emitting layer 340 can be a metal chelate compound, a bis(styrene) derivative, an aromatic amine derivative, a dibenzofuran derivative, or other types of materials. This application does not impose any special restrictions on this.

[0140] In some embodiments of this application, the main material of the organic light-emitting layer 340 is BH-01.

[0141] The guest material of the organic light-emitting layer 340 can be a compound with a condensed aryl ring or its derivative, a compound with a heteroaryl ring or its derivative, an aromatic amine derivative, or other materials; this application does not impose any special limitations on this. The guest material is also called a dopant or dopant. According to the type of light emission, it can be divided into fluorescent dopant and phosphorescent dopant. For example, specific examples of the blue fluorescent dopant include, but are not limited to:

[0142]

[0143] In some specific embodiments of this application, the guest material of the organic light-emitting layer 340 is BD-01.

[0144] The electron transport layer 350 can be a single-layer structure or a multi-layer structure, and may include one or more electron transport materials. The electron transport materials may be selected from, but are not limited to, ET-1, LiQ, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials. This application does not impose any specific limitations on these materials. The materials of the electron transport layer 350 include, but are not limited to, the following compounds:

[0145]

[0146]

[0147] In some specific embodiments of this application, the electron transport layer 350 is composed of the organic compounds of this application and LiQ.

[0148] In this application, the cathode 200 may include a cathode material that has a small work function and facilitates electron injection into the functional layers. 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 comprising magnesium and silver may be included as the cathode.

[0149] Optionally, an electron injection layer 360 may be provided between the cathode 200 and the electron transport layer 350 to enhance the ability to inject electrons into the electron transport layer 350. The electron injection layer 360 may include inorganic materials such as alkali metal sulfides and alkali metal halides, or may include complexes of alkali metals and organic materials. In some embodiments of this application, the electron injection layer 360 may include ytterbium (Yb).

[0150] A third aspect of this application provides an electronic device including the electronic components described in the second aspect of this application.

[0151] According to one implementation method, such as Figure 2 As shown, the provided electronic device is electronic device 400, which includes the aforementioned organic electroluminescent device. Electronic device 400 can be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices, such as including but not limited to computer screens, mobile phone screens, televisions, electronic paper, emergency lighting, optical modules, etc.

[0152] The following examples illustrate the synthesis method of the organic compounds of this application, but this application is not limited thereto.

[0153] Compounds synthesized using methods not mentioned in this application are all raw material products obtained through commercial means.

[0154] Synthesis Examples

[0155] I. Synthesis of intermediates

[0156] 1. Synthesis of intermediate IM a1-dX

[0157] The synthesis of IM a1-dX is illustrated using IM a1-d1 as an example:

[0158]

[0159] (1) 5-hydroxy-2-adamantanone (25.00 g, 150.40 mmol) was placed in a 150 mL round-bottom flask with deuterated benzene (250 mL) and trifluoromethanesulfonic acid (22.57 g, 150.40 mmol) and heated to 80 °C for 3 h. The reaction solution was cooled to room temperature and washed with water several times until neutral. The solution was separated and dried with anhydrous magnesium sulfate and filtered. The solvent was removed from the organic phase under reduced pressure to obtain crude product. The crude product was then crystallized with dichloromethane / n-heptane to obtain 5-deuterated phenyl-2-adamantanone (22.10 g, yield 63.5%).

[0160]

[0161] (2) 2-Bromo-4-chloroiodobenzene (70.00 g, 220.58 mmol), phenylboronic acid (26.89 g, 220.58 mmol), potassium carbonate (60.97 g, 441.15 mmol), tetrabutylammonium bromide (7.11 g, 22.06 mmol), toluene (560 mL), ethanol (140 mL), and deionized water (140 mL) were added to a three-necked flask. The mixture was stirred for 15 min under nitrogen protection. Tetra(triphenylphosphine)palladium (2.55 g, 1.21 mmol) was added, and the temperature was raised to 75-80 °C. The mixture was stirred for 26 hours. The reaction solution was cooled to room temperature, washed several times with water until neutral, and then separated. The organic phase was dried with anhydrous magnesium sulfate, filtered, and the solvent was removed from the organic phase under reduced pressure. The solution was then recrystallized from dichloromethane / n-heptane to obtain a white solid IM a1-a1 (30.20 g, yield 51.2%).

[0162]

[0163] (3) IM a1-a1 (28.0 g, 104.65 mmol) and THF (168 mL) were added to a 500 mL round-bottom flask. The system was cooled to -90 °C to -78 °C, and a tetrahydrofuran solution of n-butyllithium (2 mol / L; 62.80 mL, 125.58 mmol) was added dropwise. The reaction was carried out at -90 °C to -78 °C for 1 h. Then, 5-phenyl-2-adamantanone (23.69 g, 104.65 mmol) was dissolved in THF (120 mL) and slowly added dropwise to the reaction system. The reaction was carried out at -78 °C to -90 °C for 1 h, and then allowed to rise naturally to room temperature and stirred for 6 h. Water (200 mL) was added to the reaction system to terminate the reaction, and the mixture was extracted with ethyl acetate and water. The mixture was then dried, filtered, and the organic layer was concentrated under reduced pressure to obtain the crude product. The crude product was recrystallized with acetonitrile to obtain IM. a1-b1 (24.8g, yield 57.1%).

[0164]

[0165] (4) IM a1-b1 (24.5 g, 51.93 mmol) was added to a 500 mL round-bottom flask with acetic acid (200 mL) and sulfuric acid (98 wt%, 1 mL). The mixture was heated to 75 °C and reacted for 3 h. As the reaction proceeded, a solid was precipitated. After the reaction was completed, the system was cooled to room temperature and then filtered. The filter cake was washed with water and ethanol several times to obtain the crude product. The crude product was then crystallized with dichloromethane / n-heptane to obtain IM a1-c1 (21.2 g, yield 90.4%).

[0166]

[0167] (5) IM a1-c1 (21.0 g, 52.90 mmol), pinacol diborate (13.43 g, 45.89 mmol), tris(dibenzylideneacetone)palladium (0.48 g, 0.53 mmol), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (0.44 g, 1.06 mmol), potassium acetate (10.38 g, 105.80 mmol), and 1,4-dioxane (210 mL) were added to a three-necked round-bottom flask, heated to 80 °C under nitrogen protection, and stirred for 4 h. Then, the mixture was cooled to room temperature, washed with water, separated, and the organic phase was dried with magnesium sulfate. After filtration, the solvent was removed from the filtrate under reduced pressure. The crude product was purified by recrystallization using a toluene system to obtain solid IMa1-d1 (19.2 g, yield 76.7%).

[0168] Other IM a1-dX listed in Table 1 were synthesized using the same method as IM a1-d1. The difference was that raw material 1 was used instead of 2-bromo-4-chloroiodobenzene in step (2), raw material 2 was used instead of phenylboronic acid in step (2), and raw material 3 was used instead of 5-phenyl-2-adamantanone in step (3) and the product 5-deuterated phenyl-2-adamantanone in step (1). The main raw materials used, the synthesis of IM a1-dX, and the yield of the last step are shown in Table 1.

[0169] Table 1

[0170]

[0171]

[0172]

[0173] 2. Synthesis of intermediate IM a1-d-bX

[0174] The synthesis of IM a1-d-bX is illustrated using IM a1-d-b1 as an example:

[0175]

[0176] (1) IM a1-d1 (5.50 g, 11.26 mmol), 4-chlorobromobenzene (2.16 g, 11.26 mmol), potassium carbonate (3.11 g, 22.52 mmol), tetrabutylammonium bromide (0.32 g, 1.13 mmol), toluene (45 mL), ethanol (15 mL) and deionized water (15 mL) were added to a three-necked flask. After stirring for 15 min under nitrogen protection, tetra(triphenylphosphine)palladium (0.13 g, 0.11 mmol) was added and the temperature was raised to 75 °C-80 °C and stirred for 6 h. The reaction solution was cooled to room temperature, washed with water several times until neutral, separated, and the organic phase was dried with anhydrous magnesium sulfate. After filtration, the solvent was removed from the organic phase under reduced pressure, and then recrystallized from dichloromethane / n-heptane to obtain a white solid, namely IM a1-d-a1 (3.61 g, yield 67.9%).

[0177]

[0178] (2) IM a1-d-a1 (3.5 g, 7.40 mmol), pinacol diborate (1.88 g, 7.40 mmol), tris(dibenzylideneacetone)palladium (0.07 g, 0.07 mmol), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (0.07 g, 0.15 mmol), potassium acetate (1.45 g, 14.80 mmol), and 1,4-dioxane (40 mL) were added to a three-necked round-bottom flask, heated to 80 °C under nitrogen protection, and stirred for 3.5 h. Then, the mixture was cooled to room temperature, washed with water, separated, and the organic phase was dried with magnesium sulfate. After filtration, the solvent was removed from the filtrate under reduced pressure. The crude product was purified by recrystallization using a toluene system to obtain solid IMa1-d-b1 (2.95 g, yield 70.6%).

[0179] Other IM a1-d-bX were synthesized using the same method as IM a1-d-b1, except that raw material 4 was used instead of IM a1-d-a1 in step (1), and raw material 5 was used instead of 4-chlorobromobenzene. The main raw materials used, the synthesized IM a1-d-bX, and the yield of the last step are shown in Table 2.

[0180] Table 2

[0181]

[0182]

[0183]

[0184] 3. Synthesis of intermediate IM a1-X

[0185] Using IM a1-1 as an example, the synthesis of IM a1-X is explained.

[0186]

[0187] IM a1-d1 (13.00 g, 26.61 mmol), cyanuric chloride (4.91 g, 26.61 mmol), potassium carbonate (7.36 g, 53.23 mmol), tetrabutylammonium bromide (0.86 g, 2.66 mmol), toluene (104 mL), ethanol (26 mL), and deionized water (26 mL) were added to a three-necked flask. The mixture was stirred for 15 min under nitrogen protection, then tetra(triphenylphosphine)palladium (0.31 g, 0.27 mmol) was added and the temperature was raised to 75 °C-80 °C and stirred for 5 h. The reaction solution was cooled to room temperature, washed several times with water until neutral, and then separated. The organic phase was dried with anhydrous magnesium sulfate, filtered, and the solvent was removed from the organic phase under reduced pressure. The solution was then recrystallized from dichloroethane / n-heptane to obtain a white solid IM a1-1 (8.1 g, yield 59.6%). Other IM a1-X were synthesized using the same method as IM a1-1, except that raw material 6 was used instead of IM a1-d1 and raw material 7 was used instead of cyanuric chloride. Raw materials 6, 7 and IM a1-X and their yields are shown in Table 3.

[0188] Table 3

[0189]

[0190]

[0191]

[0192]

[0193] II. Synthesis of Compounds

[0194] Synthesis Example 1: Synthesis of Compound 1-1

[0195]

[0196] (1) IM a1-1 (7.9 g, 15.48 mmol), phenylboronic acid (1.89 g, 15.48 mmol), potassium carbonate (4.28 g, 30.95 mmol), tetrabutylammonium bromide (0.50 g, 1.55 mmol), toluene (64 mL), ethanol (16 mL) and deionized water (16 mL) were added to a three-necked flask. After stirring for 15 min under nitrogen protection, tetra(triphenylphosphine)palladium (0.18 g, 0.15 mmol) was added and the temperature was raised to 75 °C-80 °C and stirred for 8 hours. The reaction solution was cooled to room temperature, washed with water several times until neutral, separated, and the organic phase was dried with anhydrous magnesium sulfate. After filtration, the solvent was removed from the organic phase under reduced pressure, and then recrystallized from dichloromethane / n-heptane to obtain a white solid IM A1-a1 (5.2 g, yield 60.8%).

[0197]

[0198] (2) IM A1-a1 (5.0 g, 9.06 mmol), 1-naphthylboronic acid (1.56 g, 9.06 mmol), potassium carbonate (2.50 g, 18.11 mmol), tetrabutylammonium bromide (0.29 g, 0.10 mmol), toluene (40 mL), ethanol (10 mL), and deionized water (10 mL) were added to a three-necked flask. Under nitrogen protection, the mixture was stirred for 15 min, then tetra(triphenylphosphine)palladium (0.10 g, 0.09 mmol) was added, and the temperature was raised to 75-80 °C and stirred for 10 h. The reaction mixture was cooled to room temperature, washed several times with water until neutral, and then separated. The organic phase was dried with anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. The organic phase was then slurried with toluene to obtain a white solid, compound 1-1 (3.70 g, yield 63.5%). Mass spectrometry: m / z = 644.3 [M+H] + .

[0199] The compounds listed in Table 4 were synthesized using the same method as compound 1-1, except that raw material 8 was used instead of IM a1-1, raw material 9 was used instead of phenylboronic acid, and raw material 10 was used instead of 1-naphthoboronic acid. The main raw materials used, the synthesized compounds, their yields, and mass spectrometry results are shown in Table 4.

[0200] Table 4

[0201]

[0202]

[0203]

[0204]

[0205]

[0206]

[0207] NMR data for some intermediates and compounds are shown in Table 5 below:

[0208] Table 5

[0209]

[0210] Fabrication and evaluation of organic electroluminescent devices:

[0211] This application also provides an organic electroluminescent device, including an anode, a cathode, and an organic layer between the anode and the cathode, wherein the organic layer includes the aforementioned organic compound of this application. The organic electroluminescent device of this application will be described in detail below through embodiments. However, the following embodiments are merely examples of this application and are not intended to limit the scope of this application.

[0212] Example 1: Fabrication of a blue organic electroluminescent device

[0213] The anode is prepared through the following process: ITO / Ag / ITO with a thickness of [missing information] is [missing information]. The substrate (manufactured by Corning) is cut to a size of 40mm×40mm×0.7mm and prepared into an experimental substrate with cathode, anode and insulating layer patterns by photolithography. The surface is treated with ultraviolet ozone and O2:N2 plasma to increase the work function of the anode (experimental substrate) and remove scum.

[0214] HI-01:PAPB was co-deposited at a weight ratio of 2%:98% using vacuum evaporation on the experimental substrate to form... A hole injection layer is formed, and PAPB is deposited on the hole injection layer to form a thickness of [missing information]. The hole transport layer (HTL).

[0215] HT-17 was vacuum-deposited onto the hole transport layer to form a layer with a thickness of [missing information]. The electron blocking layer.

[0216] On the electron blocking layer, BH-01 and BD-01 were co-deposited at a weight ratio of 97%:3% to form a layer with a thickness of [missing information]. Organic light-emitting layer (EML, blue light-emitting layer).

[0217] Compound 1-1 and LiQ were deposited on the organic light-emitting layer at a 1:1 evaporation rate ratio to form... A thick electron transport layer.

[0218] Yb is deposited onto the electron transport layer to form a thickness of [missing information]. An electron-injected layer (EIL) was formed, and then magnesium (Mg) and silver (Ag) were vacuum-deposited onto the electron-injected layer at a deposition rate ratio of 1:9, forming a layer with a thickness of [missing information]. The cathode.

[0219] Finally, a thickness of [thickness] is deposited on the aforementioned cathode. The organic capping layer CP-01 is used to complete the fabrication of the organic light-emitting device.

[0220] Examples 2-29

[0221] Organic electroluminescent devices were prepared using the same method as in Example 1, except that compounds 1-1 were replaced with the compounds shown in Table 6 when preparing the electron transport layer.

[0222] Comparative Examples 1 to 3:

[0223] Organic electroluminescent devices were prepared using the same method as in Example 1, except that when preparing the electron transport layer, compound 1-1 was replaced with compound a, compound b, and compound c, respectively.

[0224] The structures of the materials used in the comparative and example studies for fabricating organic electroluminescent devices are as follows:

[0225]

[0226] The performance of the blue organic electroluminescent devices prepared in Examples 1-29 and Comparative Examples 1-3 was tested, specifically at 10 A / cm. 2 The photoelectric performance and lifetime data of the device under the specified conditions were analyzed, and the results are shown in Table 6 below.

[0227] Table 6

[0228]

[0229]

[0230] Referring to the table above, Examples 1-29, which used the organic compounds of this application as the electron transport layer, showed an improvement in current efficiency of at least 10.8% and lifetime of at least 11.1% compared to Comparative Examples 1-3. Therefore, when the organic compounds of this application are used to prepare organic electroluminescent devices, they can effectively reduce the driving voltage of the device and also improve the device lifetime.

[0231] The organic compounds of this application are composed of aryl-substituted adamantane groups and triazine groups. Generally, adamantane has excellent sublimation properties due to its large steric dimensionality and robustness, and has a stable chemical structure, thus exhibiting excellent thermal stability. The hydrogen on the aryl-substituted adamantane can saturate the substituted carbon, further enhancing its stability. Combined with triazine groups, it can significantly improve device efficiency and lifespan.

[0232] Those skilled in the art will understand that the above embodiments are specific implementations of this application, and in practical applications, various changes can be made in form and detail without departing from the spirit and scope of this application.

Claims

1. An organic compound, characterized in that, This organic compound has the structure shown in Formula 1: Ar3 is selected from phenyl and pentadeuterated phenyl; X1, X2, and X3 represent C(H) or N atoms, and at least one of X1, X2, and X3 is an N atom; L is selected from single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted fluorene; The substituents in L may be the same or different, and each is independently selected from deuterium, methyl or phenyl; L1 and L2 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene; The substituents in L1 and L2 may be the same or different, and each is independently selected from deuterium or phenyl; Ar1 and Ar2 are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl or substituted or unsubstituted carbazoyl. Ar1 and Ar2 may have the same or different substituents, each independently selected from deuterium, fluorine, cyano, methyl, tert-butyl, trimethylsilyl, and phenyl. R1 and R2 may be the same or different, and each is independently selected from cyano, methyl, tert-butyl or phenyl; n1 represents the number of R1s, and is selected from 0, 1, 2, 3 or 4; when n1 is greater than 1, any two R1s are the same or different. n2 represents the number of R2s, and is selected from 0, 1, 2 or 3; when n2 is greater than 1, any two R2s are the same or different.

2. The organic compound according to claim 1, characterized in that, Each group is independently selected from the group consisting of the following groups:

3. The organic compound according to claim 1, characterized in that, The organic compound is selected from the group consisting of the following compounds:

4. An electronic component, comprising an anode and a cathode disposed opposite to each other, 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 1-3.

5. The electronic component according to claim 4, wherein, The electronic component is an organic electroluminescent device.

6. The electronic component according to claim 4, wherein, The functional layer includes an electron transport layer, which contains the organic compound.

7. An electronic device comprising the electronic element according to any one of claims 4-6.

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