Organic compound, organic electroluminescent device, and electronic device

Abstract

The invention belongs to the technical field of organic electroluminescence, and relates to an organic compound, an organic electroluminescence device using the organic compound and an electronic device, the organic compound has a structure as shown in a formula 1, and when the organic compound is used in the organic electroluminescence device, the performance of the organic electroluminescence device can be remarkably improved.

Description

Technical Field

[0001] This application relates to the field of organic compound technology, and more particularly to an organic compound and an organic electroluminescent device and electronic device containing the organic compound. Background Technology

[0002] With the development of electronic technology and the advancement of materials science, the application range of electronic components used to achieve electroluminescence is becoming increasingly wide. 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 organic light-emitting layer, a hole transport layer located between the organic light-emitting layer and the anode, and an electron transport layer located between the organic light-emitting layer and the cathode. Taking an organic electroluminescent device as an example, it generally includes an anode, a hole transport layer, a light-emitting adjustment layer, an organic light-emitting layer, an electron transport layer, an electron injection 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 organic light-emitting layer, and holes on the anode side also move towards 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.

[0003] Existing technologies disclose host materials for fabricating organic light-emitting layers in organic electroluminescent devices. However, it remains necessary to continue developing novel materials to further improve the performance of organic electroluminescent devices. Summary of the Invention

[0004] To address the aforementioned problems, this application aims to provide an organic compound and a composition containing the organic compound, an organic electroluminescent device, and an electronic device, wherein the organic compound can improve the performance of the organic electroluminescent device and the electronic device, for example, by reducing the driving voltage of the device and improving the device efficiency and lifespan.

[0005] In a first aspect, this application provides an organic compound having the structure shown in Formula 1:

[0006]

[0007] Wherein, group A is the group shown in Formula 2, group B is the group shown in Formula 3, and group A and group B are connected to the adjacent positions of the phenanthrene group in Formula 1;

[0008] L, L1, and L2 may be the same or different, and are independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms.

[0009] Ar1 and Ar2 may be the same or different, and are independently selected from substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms, respectively.

[0010] The substituents in L, L1, L2, Ar1, and Ar2 may be the same or different, and are independently selected from deuterium, halogen groups, cyano, alkyl groups with 1 to 10 carbon atoms, cycloalkyl groups with 1 to 20 carbon atoms, aryl groups with 6 to 20 carbon atoms, deuterated aryl groups with 6 to 20 carbon atoms, and haloaryl groups with 6 to 20 carbon atoms;

[0011] Each R1 is independently selected from deuterium, halogen group, cyano, alkyl with 1 to 10 atoms, cycloalkyl with 1 to 20 carbon atoms, aryl with 6 to 20 carbon atoms, deuterated aryl with 6 to 20 carbon atoms, haloaryl with 6 to 20 carbon atoms, and heteroaryl with 3 to 30 carbon atoms;

[0012] n1 is the number of R1s, selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8. When n1 is greater than 1, any two R1s are the same or different.

[0013] A second aspect of this application provides an organic electroluminescent device, 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 disclosed in the first aspect of this application.

[0014] A third aspect of this application provides an electronic device including the organic electroluminescent device disclosed in the second aspect of this application.

[0015] The core structure of the organic compound in this application consists of a triazine group, a phenanthrene group, and an N-carbazole group. The triazine group and the N-carbazole group are attached to adjacent positions on the phenanthrene group. This connection method gives the compound higher electron mobility and a higher T1 energy level, while also enhancing the compound's steric effect. When the organic compound of this application is used as the host material of the organic light-emitting layer in an organic electroluminescent device, it can improve the device's luminous efficiency and lifetime.

[0016] Other features and advantages of this application will be described in detail in the following detailed description section. Attached Figure Description

[0017] 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.

[0018] Figure 1 This is a schematic diagram of the structure of an organic electroluminescent device according to this application.

[0019] Figure 2This is a schematic diagram of the structure of an electronic device according to this application.

[0020] Figure Labels

[0021] 100, Anode 200, Cathode 300, Functional Layer 310, Hole Injection Layer

[0022] 320, Hole transport layer; 330, Luminescent adjustment layer; 340, Organic light-emitting layer; 350, Electron transport layer

[0023] 360°, electron injection layer 400°, electronic device Detailed Implementation

[0024] In view of the above-mentioned problems existing in the prior art, the purpose of this application is to provide an organic compound and an organic electroluminescent device and electronic device containing the organic compound. The organic compound can improve the performance of the organic electroluminescent device and electronic device, such as reducing the driving voltage of the device and improving the device efficiency and lifespan.

[0025] A first aspect of this application provides an organic compound having a structure as shown in Formula 1:

[0026]

[0027] Wherein, group A is the group shown in Formula 2, group B is the group shown in Formula 3, and group A and group B are connected in adjacent positions to the phenanthrene group in Formula 1.

[0028] L, L1, and L2 may be the same or different, and are independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms.

[0029] Ar1 and Ar2 may be the same or different, and are independently selected from substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms, respectively.

[0030] The substituents in L, L1, L2, Ar1, and Ar2 may be the same or different, and are independently selected from deuterium, halogen groups, cyano, alkyl groups with 1 to 10 carbon atoms, cycloalkyl groups with 1 to 20 carbon atoms, aryl groups with 6 to 20 carbon atoms, deuterated aryl groups with 6 to 20 carbon atoms, and haloaryl groups with 6 to 20 carbon atoms;

[0031] Each R1 is independently selected from deuterium, halogen group, cyano, alkyl with 1 to 10 atoms, cycloalkyl with 1 to 20 carbon atoms, aryl with 6 to 20 carbon atoms, deuterated aryl with 6 to 20 carbon atoms, haloaryl with 6 to 20 carbon atoms, and heteroaryl with 3 to 30 carbon atoms;

[0032] n1 is the number of R1s, selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8. When n1 is greater than 1, any two R1s are the same or different.

[0033] In this application, the descriptive phrases "each...independently is," "...each independently is," and "...each independently is" 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.

[0034] 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, cyano, halogen groups, alkyl, aryl, heteroaryl, deuterated aryl, haloaryl, cycloalkyl, etc. The number of substituents can be one or more.

[0035] In this application, "multiple" means two or more, such as two, three, four, five, six, etc.

[0036] 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.

[0037] In this application, aryl refers to any optional functional group or substituent derived from an aromatic carbon ring. The aryl group can be a monocyclic aryl (e.g., phenyl) or a polycyclic aryl; in other words, the aryl group can be a monocyclic aryl, a fused-ring aryl, two or more monocyclic aryl groups linked by carbon-carbon bonds, a monocyclic aryl and a fused-ring aryl linked by carbon-carbon bonds, or two or more fused-ring aryl groups linked by carbon-carbon bonds. That is, unless otherwise stated, two or more aromatic groups linked by carbon-carbon bonds can also be considered as the aryl group 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, anthracene, phenanthryl, biphenyl, terphenyl, triphenylene, perylene, benzo[9,10]phenanthryl, pyrene, benzofluoranthracene, 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.

[0038] In this application, terphenyl includes

[0039] In this application, the number of carbon atoms in the 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 with 18 carbon atoms refers to a total number of 18 carbon atoms in the aryl group and the substituents.

[0040] In this application, the number of carbon atoms in the substituted or unsubstituted aryl group can be 6, 10, 12, 13, 14, 15, 16, 17, 18, 20, 24, 25, or 30. In some embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group with 6 to 30 carbon atoms; in other embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group with 6 to 25 carbon atoms; in still other embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group with 6 to 20 carbon atoms; and in yet another embodiment, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group with 6 to 12 carbon atoms.

[0041] In this application, aryl groups used as substituents for L1, L2, Ar1, and Ar2 include, but are not limited to, phenyl, naphthyl, etc.

[0042] In this application, a heteroaryl group refers to a monovalent aromatic ring or its derivative containing 1, 2, 3, 4, 5, or 6 heteroatoms. The heteroatoms 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 system of multiple aromatic rings linked by carbon-carbon bonds, and any 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, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, isoquinolinyl, indolyl, carbazoleyl, benzoxazolyl, benzoimidazolyl, benzothiazolyl, benzocarbazoleyl, benzothiaphenyl, dibenzothiaphenyl, thiaphenothiaphenyl, benzofuranyl, phenanthrololinyl, isoxazolyl, thiadiazolyl, phenthiaazinyl, silfluorenyl, dibenzofuranyl, and N-phenylcarbazoleyl, N-pyridylcarbazoleyl, N-methylcarbazoleyl, etc.

[0043] In this application, the number of carbon atoms in the substituted or unsubstituted heteroaryl group can be selected from 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, or 30. In some embodiments, the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group with 5 to 20 carbon atoms, and in other embodiments, the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group with 12 to 18 carbon atoms.

[0044] In this application, the substituted heteroaryl group can 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, deuterated aryl groups, and haloaryl groups. It should be understood that the number of carbon atoms in the substituted heteroaryl group refers to the total number of carbon atoms in the heteroaryl group and the substituents on the heteroaryl group.

[0045] In this application, alkyl groups having 1 to 10 carbon atoms can include straight-chain alkyl groups having 1 to 10 carbon atoms and branched alkyl groups having 3 to 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, and n-hexyl.

[0046] In this application, the halogen group may be, for example, fluorine, chlorine, bromine, or iodine.

[0047] In this application, specific embodiments of deuterated aryl groups include, but are not limited to, pentadeuterated phenyl and pentadeuterated biphenyl.

[0048] In this application, the number of carbon atoms in cycloalkyl groups with 3 to 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, cyclohexyl, and adamantyl.

[0049] In this application, the non-positioned connecting key refers to the single bond extending from the loop system. This indicates that one end of the linker can be connected to any position in the ring system that the linker penetrates, and the other end is connected to the rest of the compound molecule. For example, as shown in equation (f) below, the naphthyl group represented by equation (f) is connected to other positions in the molecule through two non-positional linkers that penetrate the bicyclic ring. This means that any possible connection mode shown in equations (f-1) to (f-10) is included.

[0050]

[0051] For example, as shown in the following formula (X'), the dibenzofuran group represented by formula (X') is connected to other positions of the molecule through 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.

[0052]

[0053] In some embodiments of this application, the organic compound is selected from the structures shown in Formula 1-1 and Formula 1-2:

[0054]

[0055] In Equations 1-1 and 1-2,

[0056] L, L1, and L2 may be the same or different, and are independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms.

[0057] Ar1 and Ar2 may be the same or different, and are independently selected from substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms, respectively.

[0058] The substituents in L, L1, L2, Ar1, and Ar2 may be the same or different, and are independently selected from deuterium, halogen groups, cyano, alkyl groups with 1 to 10 carbon atoms, cycloalkyl groups with 1 to 20 carbon atoms, aryl groups with 6 to 20 carbon atoms, deuterated aryl groups with 6 to 20 carbon atoms, and haloaryl groups with 6 to 20 carbon atoms;

[0059] Each R1 is selected from deuterium, halogen groups, cyano, alkyl with 1 to 10 atoms, cycloalkyl with 1 to 20 carbon atoms, aryl with 6 to 20 carbon atoms, deuterated aryl with 6 to 20 carbon atoms, haloaryl with 6 to 20 carbon atoms, and heteroaryl with 3 to 30 carbon atoms.

[0060] n1 is the number of R1s, selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8. When n1 is greater than 1, any two R1s are the same or different.

[0061] In some embodiments of this application, the organic compound is selected from the structures represented by formulas A to G:

[0062]

[0063] In equations A to G

[0064] L, L1, and L2 may be the same or different, and are independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms.

[0065] Ar1 and Ar2 may be the same or different, and are independently selected from substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms, respectively.

[0066] The substituents in L, L1, L2, Ar1, and Ar2 may be the same or different, and are independently selected from deuterium, halogen groups, cyano, alkyl groups with 1 to 10 carbon atoms, cycloalkyl groups with 1 to 20 carbon atoms, aryl groups with 6 to 20 carbon atoms, deuterated aryl groups with 6 to 20 carbon atoms, and haloaryl groups with 6 to 20 carbon atoms;

[0067] Each R1 is selected from deuterium, halogen groups, cyano, alkyl with 1 to 10 atoms, cycloalkyl with 1 to 20 carbon atoms, aryl with 6 to 20 carbon atoms, deuterated aryl with 6 to 20 carbon atoms, haloaryl with 6 to 20 carbon atoms, and heteroaryl with 3 to 30 carbon atoms.

[0068] n1 is the number of R1s, selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8. When n1 is greater than 1, any two R1s are the same or different.

[0069] In some embodiments of this application, L is selected from substituted or unsubstituted aryl groups with a single bond and 6 to 12 carbon atoms.

[0070] Optionally, the substituents in L may be the same or different, and may be independently selected from deuterium, halogen groups, cyano groups, alkyl groups having 1 to 5 carbon atoms, phenyl groups, or pentadeuterated phenyl groups.

[0071] In other embodiments of this application, L is selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, and substituted or unsubstituted biphenylene.

[0072] Optionally, the substituents in L may be the same or different, and may be independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl or pentadeuterated phenyl.

[0073] In some embodiments of this application, L is selected from the group consisting of single bonds or groups consisting of:

[0074]

[0075] Specifically, L is selected from the group consisting of single bonds or groups consisting of:

[0076]

[0077] In some embodiments of this application, L1 and L2 may be the same or different, and are independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 12 carbon atoms, and substituted or unsubstituted heteroaryl groups with 12 to 18 carbon atoms.

[0078] Optionally, the substituents in L1 and L2 may be the same or different, and may be independently selected from deuterium, halogen groups, cyano groups, alkyl groups having 1 to 5 carbon atoms, phenyl groups, or pentadeuterated phenyl groups.

[0079] In other embodiments of this application, L1 and L2 may be the same or different, and are independently selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, and substituted or unsubstituted dibenzothiophene.

[0080] Optionally, the substituents in L1 and L2 may be the same or different, and may be independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl or pentadeuterated phenyl.

[0081] In some embodiments of this application, L1 and L2 may be the same or different, and are each independently selected from the group consisting of single bonds or groups consisting of:

[0082]

[0083] Specifically, L1 and L2 may be the same or different, and are independently selected from the group consisting of single bonds or groups of the following:

[0084]

[0085]

[0086] In some embodiments of this application, Ar1 and Ar2 may be the same or different, and are independently selected from substituted or unsubstituted aryl groups having 6 to 20 carbon atoms, and substituted or unsubstituted heteroaryl groups having 12 to 18 carbon atoms.

[0087] Optionally, the substituents in Ar1 and Ar2 may be the same or different, and may be independently selected from deuterium, halogen groups, cyano groups, alkyl groups having 1 to 5 carbon atoms, phenyl groups, naphthyl groups, or pentadeuterated phenyl groups.

[0088] In other embodiments of this application, Ar1 and Ar2 may be the same or different, and are independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, and substituted or unsubstituted dibenzothiophene.

[0089] Optionally, the substituents in Ar1 and Ar2 may be the same or different, and may be independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl or pentadeuterated phenyl.

[0090] In some embodiments of this application, Ar1 and Ar2 may be the same or different, and are each independently selected from the group consisting of:

[0091]

[0092] Specifically, Ar1 and Ar2 may be the same or different, and are each independently selected from the group consisting of the following groups:

[0093]

[0094]

[0095] In some embodiments of this application, Whether identical or different, each is independently selected from the group consisting of the following groups:

[0096]

[0097] Specifically, Whether identical or different, each is independently selected from the group consisting of the following groups:

[0098]

[0099] In some embodiments of this application, group A contains Selected from the group consisting of the following groups:

[0100] Specifically, in group A Selected from the group consisting of the following groups:

[0101]

[0102]

[0103] In some embodiments of this application, each R1 is independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, biphenyl, or pentadeuterated phenyl.

[0104] Optionally, each R1 is independently selected from the group consisting of deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, or the group consisting of the following groups;

[0105]

[0106] Specifically, each R1 is independently selected from the group consisting of deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, or the group consisting of the following groups;

[0107]

[0108] In some embodiments of this application, Equation 3 Selected from the group consisting of the following groups:

[0109]

[0110] In some embodiments of this application, the organic compound is selected from the compounds shown in claim 12.

[0111] In one embodiment of this application, the organic electroluminescent device is a phosphorescent device.

[0112] In one specific embodiment of this application, the organic electroluminescent device is a green phosphorescent organic electroluminescent device.

[0113] In some embodiments of this application, the organic electroluminescent device sequentially includes an anode (ITO substrate), a hole transport layer, a light-emitting modulator, an organic light-emitting layer, an electron transport layer, an electron injection layer, a cathode (Mg-Ag mixture), and an organic capping layer.

[0114] In one specific embodiment of this application, such as Figure 1 As shown, the organic electroluminescent device of this application includes an anode 100, a cathode 200, and at least one functional layer 300 between the anode layer and the cathode layer. The functional layer 300 includes a hole injection layer 310, a hole transport layer 320, a light emission adjustment layer 330, an organic light emission layer 340, an electron transport layer 350, and an electron injection layer 360.

[0115] Optionally, the anode 100 comprises an anode material, preferably one with a high work function that facilitates hole injection into the functional layer. Specific examples of anode materials include: metals such as nickel, platinum, vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; or conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, and polyaniline, but are not limited thereto. Preferably, a transparent electrode comprising indium tin oxide (ITO) as the anode is included.

[0116] Optionally, the hole transport layer 320 may include one or more hole transport materials, which may be selected from carbazole polymers, carbazole-linked triarylamine compounds, or other types of compounds. This application does not impose any specific limitations on these materials. For example, in some embodiments of this application, the hole transport layer 320 is composed of HT-1.

[0117] Optionally, the light-emitting adjustment layer 330 (also referred to as a hole adjustment layer, electron blocking layer, hole auxiliary layer, hole buffer layer, light-emitting auxiliary layer, or second hole transport layer) may include one or more hole transport materials. The hole transport material may be selected from carbazole polymers, carbazole-linked triarylamine compounds, or other types of compounds; this application does not impose any special limitations on this. For example, in some embodiments of this application, the light-emitting adjustment layer 330 is composed of HT-2.

[0118] Optionally, the organic light-emitting layer 340 may be composed of a single light-emitting material, or it may include a host material and a guest material. Optionally, the organic light-emitting layer 340 is composed of a host material and a guest material. Holes and electrons injected into the organic light-emitting layer 330 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 guest material, thereby enabling the guest material to emit light.

[0119] The guest material of the organic light-emitting layer 340 can be a compound or its derivative having a condensed aryl ring, a compound or its derivative having a heteroaryl ring, an aromatic amine derivative, or other materials, and this application does not impose any special restrictions on this.

[0120] In some embodiments of this application, the organic electroluminescent device is a green organic electroluminescent device, which includes an organic light-emitting layer, and the organic light-emitting layer includes the organic compound of this application, compound GH-1, and guest material GD-01.

[0121] The electron transport layer 350 can be a single-layer structure or a multi-layer structure, and it can include one or more electron transport materials. The electron transport materials can be selected from benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials, and this application does not make any special limitations in this regard. For example, in some embodiments of this application, the electron transport layer 350 can be composed of ET-1 and LiQ.

[0122] Optionally, the cathode 200 comprises a cathode material having a small work function that 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. Preferably, a metal electrode comprising silver and magnesium is included as the cathode.

[0123] 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, and this application does not impose any special limitations on this. In some embodiments of this application, the hole injection layer 310 may be composed of PD-1 and HT-1.

[0124] 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).

[0125] A fourth aspect of this application also provides an electronic device comprising the organic electroluminescent device described in this application.

[0126] For example, such as Figure 2 As shown, the electronic device provided in this application is a first electronic device 400, which includes any of the organic electroluminescent devices described in the above-described embodiments. This electronic device can be a display device, a lighting device, an optical communication device, or other types of electronic devices, such as, but not limited to, computer screens, mobile phone screens, televisions, electronic paper, emergency lighting, optical modules, etc. Since the first electronic device 400 has the aforementioned organic electroluminescent device, it has the same beneficial effects, which will not be repeated here.

[0127] The present application will now be described in detail with reference to embodiments. However, the following description is intended to explain the present application and not to limit the scope of the present application in any way.

[0128] Synthesis Examples

[0129] Those skilled in the art will recognize that the chemical reactions described herein can be suitably used to prepare many of the organic compounds of this application, and other methods for preparing the compounds of this application are considered to be within the scope of this application. For example, the synthesis of those non-illustrative compounds according to this application can be successfully accomplished by those skilled in the art through modification methods, such as appropriately protecting interfering groups, utilizing other known reagents besides those described herein, or making some conventional modifications to the reaction conditions. Compounds for which synthetic methods are not mentioned in this application are commercially available starting materials.

[0130] Synthesis of intermediate A-1

[0131]

[0132] Under nitrogen protection, SMA-1 (30.00 g, 109.04 mmol), SMB-1 (30.21 g, 109.01 mmol), tetra(triphenylphosphine)palladium (1.26 g, 1.09 mmol), anhydrous potassium carbonate (30.14 g, 218.08 mmol), tetrabutylammonium bromide (3.51 g, 10.90 mmol), toluene (240 mL), anhydrous ethanol (120 mL), and deionized water (60 mL) were added sequentially to a three-necked flask. Stirring and heating were initiated, and the mixture was refluxed for 16 h. After cooling to room temperature, the mixture was extracted with dichloromethane (100 mL × 3 times). The organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the solvent was removed by vacuum distillation to obtain the crude product. The crude product was purified by silica gel column chromatography using n-heptane / dichloromethane as the mobile phase to obtain intermediate A-1 (32.62 g, yield: 70%).

[0133] Following the synthesis method of intermediate A-1, reactant A in Table 1 was used instead of SMA-1, and reactant B was used instead of SMB-1 to synthesize intermediates A-2 to A-13 and B-1 to B-10.

[0134] Table 1

[0135]

[0136]

[0137]

[0138] Synthesis of Compound 1

[0139]

[0140] Under nitrogen protection, A-1 (20.00 g, 46.78 mmol), SMC-1 (8.95 g, 51.06 mmol), potassium phosphate (29.79 g, 140.35 mmol), and NMP (N-methylpyrrolidone, 100 mL) were added sequentially to a three-necked flask. Stirring and heating were initiated, and the mixture was refluxed for 16 h. After the system cooled to room temperature, 150 mL of water was added, and stirring continued for 30 min. A solid precipitated, which was directly filtered to obtain the crude product. The crude product was purified by silica gel column chromatography using n-heptane / dichloromethane as the mobile phase to obtain compound 1 (18.54 g, yield: 68%).

[0141] Following the synthetic method of compound 1, reactant C from Table 2 was used instead of A-1, and reactant D was used instead of SMC-1 to synthesize the compounds shown in Table 2.

[0142] Table 2

[0143]

[0144]

[0145]

[0146] Synthesis of compound 209:

[0147]

[0148] The following compounds were reacted: B-1 (20.00 g, 45.05 mmol), SMC-1 (8.68 g, 49.51 mmol), potassium carbonate (12.45 g, 90.11 mmol), cuprous iodide (1.71 g, 9.01 mmol), 18-crown ether-6 (1.19 g, 4.50 mmol), 1,10-phenanthroline (3.25 g, 18.02 mmol), and N,N-dimethylformamide (200 mL). After 24 h, the reaction was complete. The mixture was cooled to room temperature, and 500 mL of water was added. A large amount of solid precipitated. The solid was filtered, and the filter cake was completely dissolved in 300 mL of dichloromethane. The solution was washed with water until neutral, and the organic layer was dried over anhydrous magnesium sulfate. The solution was then concentrated. The crude product was purified by silica gel column chromatography using n-heptane / dichloromethane as the mobile phase to give compound 209 (18.37 g, yield: 70%).

[0149] Following the synthetic method of compound 209, reactant E was used instead of B-1 in Table 3 below, and reactant F was used instead of SMC-1 to synthesize the compound.

[0150] Table 3

[0151]

[0152]

[0153]

[0154] Mass spectrometry data of some compounds are shown in Table 4 below.

[0155] Table 4

[0156]

[0157] NMR data for some compounds are shown in Table 5 below.

[0158] Table 5

[0159]

[0160] Fabrication of organic electroluminescent devices

[0161] Example 1: Fabrication of Green Organic Electroluminescent Devices

[0162] Devices are fabricated using the following process.

[0163] At ITO / Ag / ITO thickness On the experimental substrate, surface treatment is performed using ultraviolet light, ozone, and O2:N2 ions to increase the work function of the anode. Organic solvents can be used to clean the surface of the experimental substrate to remove impurities and oil stains.

[0164] Compounds HT-1 and PD-1 were co-deposited on the experimental substrate at a deposition rate of 97%:3%, forming a layer with a thickness of [missing information]. Hole injection layer.

[0165] Compound HT-1 was deposited onto the hole injection layer to form a thickness of [missing information]. The hole transport layer.

[0166] Compound HT-2 was deposited on the hole transport layer to form a thickness of [missing information]. The light-emitting adjustment layer.

[0167] On the light-emitting adjustment layer, GH-1 (first host compound), compound 1 (second host compound), and GD-1 (doped guest) were co-deposited at a deposition rate of 60%:40%:10% to form a layer with a thickness of [missing information]. The organic light-emitting layer.

[0168] On the organic light-emitting layer, compounds ET-1 and LiQ were co-deposited at a 50%:50% evaporation rate to form a layer with a thickness of [missing information]. The electron transport layer.

[0169] Yb is deposited on the electron transport layer to form a thickness of An electron-injected layer is formed; then, magnesium (Mg) and silver (Ag) are co-deposited on the electron-injected layer at a deposition rate of 10%:90%, forming a layer with a thickness of [missing information]. The cathode.

[0170] Compound CP-1 was deposited on the cathode to form a thickness of [missing information]. The organic coating layer is used to complete the fabrication of green organic electroluminescent devices.

[0171] Examples 2 to 34:

[0172] Except that, when preparing the organic light-emitting layer, the compound listed in Table 6 (collectively referred to as "Compound X") was used instead of Compound 1 in Example 1, the organic electroluminescent device compound 1 was prepared using the same method as in Example 1.

[0173] Comparative Examples 1 to 2:

[0174] Except that, when preparing the organic light-emitting layer, compounds A and B from Table 6 were used to replace compound 1 in Example 1, the organic electroluminescent device was prepared using the same method as in Example 1.

[0175] The compounds used in the preparation of the various examples and comparative examples have the following structures:

[0176]

[0177] The performance of the green organic electroluminescent devices prepared in Examples 1-34 and Comparative Examples 1-2 was tested, specifically at 15 mA / cm². 2 The IVL performance of the device was tested under the condition of 20 mA / cm. 2 The lifetime of the T95 device was tested under the following conditions, and the test results are shown in Table 6 below.

[0178] Table 6

[0179]

[0180]

[0181] As can be seen from Table 6 above, compared with Comparative Examples 1 and 2, when the organic compound of this application is used as the main material of the green organic electroluminescent device, the current efficiency of the device is increased by at least 12.7% and the T95 lifetime is increased by at least 13.1%.

[0182] Compared to Comparative Examples 1 and 2, when the organic compounds of this application are used as the host materials for green photoelectronic devices, the resulting devices exhibit significantly improved lifetime characteristics at similar operating voltages. This is likely because, compared to compound A, the carbazole and phenanthrene groups in the compounds of this application are linked by single bonds, resulting in a wider conjugation range, higher carrier mobility, and more balanced transport, thereby improving the luminous efficiency of the devices. Compared to compound B, the compounds of this application possess a higher T1 energy level, significantly improving the electron injection characteristics of the material. When used as the host material for the organic light-emitting layer of organic light-emitting electroluminescent devices, they can improve the efficiency and lifetime of the devices.

[0183] The embodiments of this application have been described in detail above with reference to the accompanying drawings. However, this application is not limited to the specific details of the above embodiments. Within the scope of the technical concept of this application, various simple modifications can be made to the technical solution of this application, and these simple modifications all fall within the protection scope of this application.

Claims

1. An organic compound, characterized in that, This organic compound has the structure shown in Formula 1: Wherein, group A is the group shown in Formula 2, group B is the group shown in Formula 3, and group A and group B are connected to the adjacent positions of the phenanthrene group in Formula 1; L, L1, and L2 may be the same or different, and are independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms. Ar1 and Ar2 may be the same or different, and are independently selected from substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms, respectively. The substituents in L, L1, L2, Ar1, and Ar2 may be the same or different, and are independently selected from deuterium, halogen groups, cyano, alkyl groups with 1 to 10 carbon atoms, cycloalkyl groups with 1 to 20 carbon atoms, aryl groups with 6 to 20 carbon atoms, deuterated aryl groups with 6 to 20 carbon atoms, and haloaryl groups with 6 to 20 carbon atoms; Each R1 is independently selected from deuterium, halogen group, cyano, alkyl with 1 to 10 atoms, cycloalkyl with 1 to 20 carbon atoms, aryl with 6 to 20 carbon atoms, deuterated aryl with 6 to 20 carbon atoms, haloaryl with 6 to 20 carbon atoms, and heteroaryl with 3 to 30 carbon atoms; n1 is the number of R1s, selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8. When n1 is greater than 1, any two R1s are the same or different.

2. The organic compound according to claim 1, characterized in that, The organic compound is selected from the structures shown in formulas A to G: In equations A to G L, L1, L2, Ar1, Ar2, R1, and n1 are as defined in claim 1.

3. The organic compound according to claim 1, characterized in that, L is selected from single bonds and substituted or unsubstituted aryl groups with 6 to 12 carbon atoms; Optionally, the substituents in L may be the same or different, and may be independently selected from deuterium, halogen groups, cyano groups, alkyl groups having 1 to 5 carbon atoms, phenyl groups, or pentadeuterated phenyl groups.

4. The organic compound according to claim 1, characterized in that, L is selected from single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene; Optionally, the substituents in L may be the same or different, and may be independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl or pentadeuterated phenyl.

5. The organic compound according to claim 1, characterized in that, L1 and L2 may be the same or different, and are independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 12 carbon atoms, and substituted or unsubstituted heteroaryl groups with 12 to 18 carbon atoms. Optionally, the substituents in L1 and L2 may be the same or different, and may be independently selected from deuterium, halogen groups, cyano groups, alkyl groups having 1 to 5 carbon atoms, phenyl groups, or pentadeuterated phenyl groups.

6. The organic compound according to claim 1, characterized in that, L1 and L2 may be the same or different, and are independently selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene. Optionally, the substituents in L1 and L2 may be the same or different, and may be independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl or pentadeuterated phenyl.

7. The organic compound according to claim 1, characterized in that, Ar1 and Ar2 may be the same or different, and are independently selected from substituted or unsubstituted aryl groups with 6 to 20 carbon atoms and substituted or unsubstituted heteroaryl groups with 12 to 18 carbon atoms. Optionally, the substituents in Ar1 and Ar2 may be the same or different, and may be independently selected from deuterium, halogen groups, cyano groups, alkyl groups having 1 to 5 carbon atoms, phenyl groups, naphthyl groups, or pentadeuterated phenyl groups.

8. The organic compound according to claim 1, characterized in that, Ar1 and Ar2 may be the same or different, and are independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene. Optionally, the substituents in Ar1 and Ar2 may be the same or different, and may be independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl or pentadeuterated phenyl.

9. The organic compound according to claim 1, characterized in that, and Whether identical or different, each is independently selected from the group consisting of the following groups: Optionally, and Whether identical or different, each is independently selected from the group consisting of the following groups:

10. The organic compound according to claim 1, characterized in that, In group A Selected from the group consisting of the following groups: Optionally, in group A Selected from the group consisting of the following groups:

11. The organic compound according to claim 1, characterized in that, Each R1 is independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, biphenyl, or pentadeuterated phenyl.

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

13. An organic electroluminescent device, characterized in that, It includes an anode and a cathode arranged opposite to each other, and a functional layer disposed between the anode and the cathode; The functional layer comprises an organic compound as described in any one of claims 1 to 12; Optionally, the functional layer includes an organic light-emitting layer, which comprises an organic compound according to any one of claims 1 to 12; Optionally, the functional layer further includes a hole injection layer, a hole transport layer, a light emission adjustment layer, an electron transport layer, and an electron injection layer.

14. An electronic device, characterized in that, Including the organic electroluminescent device as described in claim 13.

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