Organic compounds, organic electroluminescent devices and electronic devices
By using organic compounds with a benzo[phenanthrene]oxazole/thiazole core structure as electron transport materials, the shortcomings of organic electroluminescent devices in terms of lifetime and efficiency are solved, the carrier mobility and exciton generation efficiency are improved, and the luminescence performance of the devices is enhanced.
Patent Information
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- SHAANXI LIGHTE OPTOELECTRONICS MATERIAL CO LTD
- Filing Date
- 2023-04-07
- Publication Date
- 2026-07-31
AI Technical Summary
Existing organic electroluminescent devices have shortcomings in terms of lifespan and efficiency, especially in large-area displays where the driving voltage is high, and luminous efficiency and current efficiency need to be improved.
An organic compound containing a benzo[phenanthrene]oxazole/thiazole core structure is provided as the host material for an electron transport-type luminescent layer. It is connected to electron-feeding groups to enhance intermolecular forces, improve carrier mobility, and increase exciton generation and utilization efficiency.
By improving carrier balance and widening the carrier recombination region, the luminous efficiency and lifetime of the device can be improved.
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Figure CN118005622B_ABST
Abstract
Description
Technical Field
[0001] This application relates to the field of organic electroluminescent materials technology, and more particularly to organic compounds and organic electroluminescent devices and electronic devices containing the same. 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 or photoelectric conversion is becoming increasingly wide. Organic light-emitting diodes (OLEDs) 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 first hole transport layer, and an electron transport layer. When a voltage is applied to the cathode and anode, 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 light-emitting layer. Electrons and holes combine in the electroluminescent layer to form excitons. The excitons are in an excited state and release energy outward, thereby causing the electroluminescent layer to emit light.
[0003] The main problems with existing organic electroluminescent devices are lifespan and efficiency. As displays become larger, driving voltages also increase, and luminous efficiency and current efficiency need to be improved. Therefore, it is necessary to continue to develop new materials to further improve the performance of organic electroluminescent devices. Summary of the Invention
[0004] 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 be used in organic electroluminescent devices to improve the performance of the devices.
[0005] According to a first aspect of this application, an organic compound is provided having a structure as shown in Formula 1:
[0006]
[0007] In this case, one of X and Y is O or S, and the other is...
[0008] Each of R1, R2, and R3 may be the same or different, and is independently selected from hydrogen, deuterium, cyano, halogen group, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, alkoxy with 1 to 10 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, triphenylsilyl, aryl with 6 to 20 carbon atoms, deuterated aryl with 6 to 20 carbon atoms, heteroaryl with 3 to 20 carbon atoms, cycloalkyl with 3 to 10 carbon atoms, or a group shown in Formula 2, and each of R1, R2, and R3 has one and only one group shown in Formula 2;
[0009]
[0010] n1 is the number of R1s, selected from 0, 1, 2, 3 or 4; when n1 is greater than 1, any two R1s are the same or different.
[0011] n2 is the number of R2, selected from 0, 1 or 2; when n2 is greater than 1, any two R2 are the same or different;
[0012] n3 is the number of R3s, selected from 0, 1, 2, 3 or 4; when n3 is greater than 1, any two R3s are the same or different.
[0013] Z1, Z2 and Z3 are each independently selected from C(H) or N, and at least two of Z1, Z2 and Z3 are N;
[0014] 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 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms.
[0015] Ar1, Ar2, and Ar3 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups with 6 to 40 carbon atoms, or substituted or unsubstituted heteroaryl groups with 3 to 40 carbon atoms.
[0016] The substituents in L, L1, L2, Ar1, Ar2, and Ar3 may be the same or different, and each is independently selected from deuterium, cyano, halogen group, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, alkoxy with 1 to 10 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, triphenylsilyl, aryl with 6 to 20 carbon atoms, deuterated aryl with 6 to 20 carbon atoms, heteroaryl with 3 to 20 carbon atoms, cycloalkyl with 3 to 10 carbon atoms, alkylthio with 1 to 10 carbon atoms, aryloxy with 6 to 20 carbon atoms, or arylthio with 6 to 20 carbon atoms; optionally, any two adjacent substituents form a cycloalkyl with 5 to 10 carbon atoms or a 6 to 15-membered unsaturated ring.
[0017] According to a second aspect of this application, an organic electroluminescent device 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.
[0018] According to a third aspect of this application, an electronic device is provided, including the organic electroluminescent device described in the second aspect.
[0019] The compound structure of this application contains a benzo[pphenanthro[x]azole / thiazole core structure, with an electron-transfer group attached to the core, making it suitable as a host material for an electron-transporting luminescent layer. The benzo[pphenanthro[x]azole / thiazole has a large conjugated system; attaching it to the electron-transfer group enhances intermolecular forces and improves the compound's carrier mobility. When this compound is used as an electron-transporting material in a hybrid host material, it can improve carrier balance in the luminescent layer, broaden the carrier recombination region, increase exciton generation and utilization efficiency, and ultimately improve device luminous efficiency and lifetime. Attached Figure Description
[0020] 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.
[0021] Figure 1 This is a schematic diagram of the structure of an organic electroluminescent device according to one embodiment of this application.
[0022] Figure 2 This is a schematic diagram of the structure of an electronic device according to one embodiment of this application.
[0023] Figure Labels
[0024] 100, Anode 200, Cathode 300, Functional Layer 310, Hole Injection Layer
[0025] 321. First hole transport layer; 322. Second hole transport layer; 330. Organic light-emitting layer; 340. Electron transport layer
[0026] 350, Electron injection layer; 400, Electronic device Detailed Implementation
[0027] 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.
[0028] According to a first aspect of this application, an organic compound is provided having a structure as shown in Formula 1:
[0029]
[0030] In this case, one of X and Y is O or S, and the other is...
[0031] Each of R1, R2, and R3 may be the same or different, and is independently selected from hydrogen, deuterium, cyano, halogen group, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, alkoxy with 1 to 10 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, triphenylsilyl, aryl with 6 to 20 carbon atoms, deuterated aryl with 6 to 20 carbon atoms, heteroaryl with 3 to 20 carbon atoms, cycloalkyl with 3 to 10 carbon atoms, or a group shown in Formula 2, and each of R1, R2, and R3 has one and only one group shown in Formula 2;
[0032]
[0033] n1 is the number of R1s, selected from 0, 1, 2, 3 or 4; when n1 is greater than 1, any two R1s are the same or different.
[0034] n2 is the number of R2, selected from 0, 1 or 2; when n2 is greater than 1, any two R2 are the same or different;
[0035] n3 is the number of R3s, selected from 0, 1, 2, 3 or 4; when n3 is greater than 1, any two R3s are the same or different.
[0036] Z1, Z2 and Z3 are each independently selected from C(H) or N, and at least two of Z1, Z2 and Z3 are N;
[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 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms.
[0038] Ar1, Ar2, and Ar3 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups with 6 to 40 carbon atoms, or substituted or unsubstituted heteroaryl groups with 3 to 40 carbon atoms.
[0039] The substituents in L, L1, L2, Ar1, Ar2, and Ar3 may be the same or different, and each is independently selected from deuterium, cyano, halogen group, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, alkoxy with 1 to 10 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, triphenylsilyl, aryl with 6 to 20 carbon atoms, deuterated aryl with 6 to 20 carbon atoms, heteroaryl with 3 to 20 carbon atoms, cycloalkyl with 3 to 10 carbon atoms, alkylthio with 1 to 10 carbon atoms, aryloxy with 6 to 20 carbon atoms, or arylthio with 6 to 20 carbon atoms; optionally, any two adjacent substituents form a cycloalkyl with 5 to 10 carbon atoms or a 6 to 15-membered unsaturated ring.
[0040] In this application, the terms "optionally" or "optionally" mean that the events or circumstances described below may or may not occur. For example, "optionally, any two adjacent substituents form a ring" means that the two substituents may or may not form a ring, that is, it includes both the scenario where two adjacent substituents form a ring and the scenario where two adjacent substituents do not form a ring. As another example, "optionally, any two adjacent substituents form a ring" means that any two adjacent substituents are connected to each other to form a ring, or that any two adjacent substituents may exist independently. "Any two adjacent" can include having two substituents on the same atom, and can also include having one substituent on each of two adjacent atoms; wherein, when there are two substituents on the same atom, the two substituents can form a saturated or unsaturated spirocyclic ring with the atom they are connected to; when there is one substituent on each of two adjacent atoms, the two substituents can fuse into a ring.
[0041] In this application, saturated or unsaturated 5- to 13-membered rings refer to carbon rings or heterocycles containing 5 to 13 ring atoms; for example, but not limited to, cyclopentane, cyclohexane, benzene ring, fluorene ring, pyran ring, tetrahydropyran ring, piperidine ring, tetrahydropiperidine ring, etc.
[0042] In this application, cycloalkyl with 5 to 10 carbon atoms refers to cycloalkyl formed by 5 to 10 carbon atoms, such as, but not limited to, cyclopentyl, cyclohexyl, adamantyl, etc.
[0043] In this application, a 6- to 15-membered unsaturated ring refers to an unsaturated ring formed by 6 to 15 ring atoms, such as, but not limited to, benzene rings, fluorene rings, furan rings, pyran rings, etc.
[0044] In this application, the descriptive phrases "each...independently is," "each...independently is," and "...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.
[0045] 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, deuterylaryl, haloaryl, cycloalkyl, etc. The number of substituents can be one or more.
[0046] In this application, "multiple" means two or more, such as two, three, four, five, six, etc.
[0047] The hydrogen atoms in the compound structure of this application include various isotopes of hydrogen, such as hydrogen (H), deuterium (D), or tritium (T).
[0048] 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 L is a substituted arylene with 12 carbon atoms, then the total number of carbon atoms in the arylene and its substituents is 12.
[0049] 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 single bonds, a monocyclic aryl and a fused-ring aryl group conjugated by carbon-carbon single bonds, or two or more fused-ring aryl groups conjugated by carbon-carbon single bonds. That is, unless otherwise stated, two or more aromatic groups conjugated by carbon-carbon single 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, phenyl-naphthyl, spirodifluorenyl, anthracene, phenanthryl, biphenyl, terphenyl, triphenylene, perylene, benzo[9,10]phenanthryl, pyrene, benzofluoranthyl, etc. Base, etc.
[0050] In this application, the term "arylene" refers to a divalent or polyvalent group formed by the further loss of one or more hydrogen atoms from an aryl group.
[0051] In this application, terphenyl includes
[0052] 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.
[0053] In this application, the substituted or unsubstituted aryl (arylene) group can have 6, 8, 10, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 28, or 30 carbon atoms. 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, it is a substituted or unsubstituted aryl group with 6 to 20 carbon atoms; in still other embodiments, it is a substituted or unsubstituted aryl group with 6 to 25 carbon atoms; in yet another embodiment, it is a substituted or unsubstituted aryl group with 6 to 18 carbon atoms; and in still another embodiment, it is a substituted or unsubstituted aryl group with 6 to 15 carbon atoms.
[0054] In this application, the fluorene group can be substituted by one or more substituents. When the fluorene group is substituted, the substituted fluorene group can be: But it is not limited to this.
[0055] In this application, aryl groups that are substituents in L, L1, L2, Ar1, Ar2, and Ar3 include, but are not limited to, phenyl, naphthyl, phenanthryl, biphenyl, fluorene, etc.
[0056] 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 connected by carbon-carbon single bonds in conjugation. 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, 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.
[0057] In this application, the term "hybrid aryl" refers to a divalent or polyvalent group formed by the further loss of one or more hydrogen atoms from a heteroaryl group.
[0058] In this application, the number of carbon atoms in the substituted or unsubstituted heteroaryl (hybrid aryl) can be selected from 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, or 30. In some embodiments, the substituted or unsubstituted heteroaryl is a substituted or unsubstituted heteroaryl with a total carbon number of 3 to 18; in other embodiments, the substituted or unsubstituted heteroaryl is a substituted or unsubstituted heteroaryl with a total carbon number of 3 to 12; and in still other embodiments, the substituted or unsubstituted heteroaryl is a substituted or unsubstituted heteroaryl with a total carbon number of 5 to 12. In this application, the heteroaryl groups that serve as substituents in L, L1, L2, Ar1, Ar2, and Ar3 are, for example but not limited to, pyridyl, carbazolyl, quinolinyl, isoquinolinyl, phenantholinyl, benzoxazolyl, benzothiazolyl, benzoimidazolyl, dibenzothiophene, and dibenzofuranyl.
[0059] 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, -CN, aryl, heteroaryl, trialkylsilyl, alkyl, cycloalkyl, haloalkyl, 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.
[0060] 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.
[0061] In this application, the halogen group is, for example, fluorine, chlorine, bromine, or iodine.
[0062] In this application, specific examples of trialkylsilyl groups include, but are not limited to, trimethylsilyl, triethylsilyl, etc.
[0063] In this application, specific examples of alkyl halogens include, but are not limited to, trifluoromethyl.
[0064] In this application, specific examples of deuterated alkyl groups include, but are not limited to, trideuterated methyl groups.
[0065] In this application, deuterated aryl refers to an aryl group containing deuteration, such as, but not limited to, pentadeuterated phenyl, heptadeuterated naphthyl, deuterated biphenyl, etc.
[0066] In this application, halogenated aryl refers to an aryl group with a halogen substituent, such as, but not limited to, fluorophenyl, fluoronaphthyl, fluorobiphenyl, etc.
[0067] In this application, the cycloalkyl group having 3 to 10 carbon atoms has, for example, 3, 4, 5, 6, 7, 8, or 10 carbon atoms. Specific examples of cycloalkyl groups include, but are not limited to, cyclopentyl, cyclohexyl, and adamantyl.
[0068] 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 connect to any position in the ring system it traverses, and the other end connects 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 traverse the bicyclic ring. This means that any possible connection mode shown in equations (f-1) to (f-10) is included.
[0069]
[0070] For another example, as shown in equation (X'), the dibenzofuran group represented by equation (X') is connected to other positions in the molecule via a non-positional linker extending from the middle of one side of the benzene ring. This means that any possible connection mode shown in equations (X'-1) to (X'-4) is included.
[0071]
[0072] In this application, a non-orienting substituent refers to a substituent connected by a single bond extending from the center of the ring system, indicating that the substituent can be attached to any possible position in the ring system. For example, as shown in equation (Y) below, the substituent R' represented by equation (Y) is connected to the quinoline ring by a non-orienting linking bond, which means that it includes any possible connection mode shown in equations (Y-1) to (Y-7):
[0073]
[0074] In some embodiments, formula 1 is selected from the structures shown in formulas (1-1) to (1-2):
[0075]
[0076] In some embodiments, one of R1 has the structure shown in Formula 2, and the remaining R1 and each of R2 and R3 are independently selected from hydrogen, deuterium, cyano, halogen group, alkyl with 1 to 4 carbon atoms, deuterated alkyl with 1 to 4 carbon atoms, haloalkyl with 1 to 4 carbon atoms, aryl with 6 to 12 carbon atoms, deuterated aryl with 6 to 12 carbon atoms, or heteroaryl with 5 to 12 carbon atoms.
[0077] In some embodiments, one of R2 has the structure shown in Formula 2, and the remaining R2 and each of R1 and R3 are independently selected from hydrogen, deuterium, cyano, halogen group, alkyl with 1 to 4 carbon atoms, deuterated alkyl with 1 to 4 carbon atoms, haloalkyl with 1 to 4 carbon atoms, aryl with 6 to 12 carbon atoms, deuterated aryl with 6 to 12 carbon atoms, or heteroaryl with 5 to 12 carbon atoms.
[0078] In some embodiments, one of R3 has the structure shown in Formula 2, and the remaining R3 and each of R1 and R2 are independently selected from hydrogen, deuterium, cyano, halogen group, alkyl with 1 to 4 carbon atoms, deuterated alkyl with 1 to 4 carbon atoms, haloalkyl with 1 to 4 carbon atoms, aryl with 6 to 12 carbon atoms, deuterated aryl with 6 to 12 carbon atoms, or heteroaryl with 5 to 12 carbon atoms.
[0079] In some embodiments, each of R1, R2, and R3 may be the same or different, and each of R1, R2, and R3 has one and only one group represented by Formula 2, while the others are each independently selected from hydrogen, deuterium, cyano, fluorine, trideuterated methyl, trimethylsilyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, pyridyl, dibenzofuranyl, dibenzothiopheneyl, or carbazoyl.
[0080] In some implementations, Z1 and Z3 are N, and Z2 is selected from C(H) or N; or Z1 and Z2 are N, and Z3 is selected from C(H) or N; or Z1, Z2 and Z3 are all N.
[0081] In some embodiments, Ar1, Ar2, and Ar3 may be the same or different, and each is 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 5, 6, 7, 8, 9, 10, 12, 13, 14, 15, 16, 17, or 18 carbon atoms.
[0082] In some embodiments, Ar1, Ar2, and Ar3 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups having 6 to 25 carbon atoms, or substituted or unsubstituted heteroaryl groups having 5 to 18 carbon atoms.
[0083] In some embodiments, the substituents in Ar1, Ar2, and Ar3 are each independently selected from deuterium, halogen groups, cyano groups, haloalkyl groups with 1 to 4 carbon atoms, deuteralkyl groups with 1 to 4 carbon atoms, alkyl groups with 1 to 4 carbon atoms, cycloalkyl groups with 5 to 10 carbon atoms, aryl groups with 6 to 15 carbon atoms, heteroaryl groups with 5 to 12 carbon atoms, trialkylsilyl groups with 3 to 8 carbon atoms, or deuteralkyl groups with 6 to 15 carbon atoms; optionally, any two adjacent substituents form a benzene ring or a fluorene ring.
[0084] In some embodiments, Ar1, Ar2, and Ar3 are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraquinyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrene, substituted or unsubstituted perylene, substituted or unsubstituted pyridyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted benzooxazolyl, substituted or unsubstituted benzimidazolyl.
[0085] Optionally, the substituents in Ar1, Ar2 and Ar3 are each independently selected from deuterium, fluorine, cyano, trideuterated methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, pyridyl, dibenzofuranyl, dibenzothiopheneyl or carbazoyl. Optionally, any two adjacent substituents in Ar1 and Ar2 form a benzene ring or a fluorene ring.
[0086] In some embodiments, Ar1 and Ar2 are each independently selected from substituted or unsubstituted groups W; wherein the unsubstituted group W is selected from the group consisting of:
[0087]
[0088] The substituted group W has one or more substituents, each of which is independently selected from deuterium, fluorine, cyano, trideuterated methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, pyridyl, dibenzofuranyl, dibenzothiopheneyl, or carbazoyl. When the number of substituents on the group W is greater than 1, the substituents may be the same or different.
[0089] In some embodiments, Ar1 and Ar2 may be the same or different, and each is independently selected from the following groups:
[0090]
[0091] In some embodiments, Ar1 and Ar2 are each independently selected from the group consisting of:
[0092]
[0093]
[0094] In some embodiments, Ar3 is selected from substituted or unsubstituted groups Q; wherein the unsubstituted group Q is selected from the group consisting of:
[0095]
[0096] The substituted group Q has one or more substituents, each of which is independently selected from deuterium, fluorine, cyano, trideuterated methyl, trimethylsilyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, phenyl or naphthyl, and when the number of substituents on group Q is greater than 1, the substituents may be the same or different.
[0097] In some embodiments, Ar3 is selected from the following groups:
[0098]
[0099] In some embodiments, Ar3 is selected from the following groups:
[0100]
[0101]
[0102] In some embodiments, L1, L2, and L may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 15 carbon atoms, and substituted or unsubstituted heteroaryl groups with 12 to 18 carbon atoms.
[0103] In some embodiments, L1, L2, and L may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted aryl groups having 6, 7, 8, 9, 10, 11, 12, 13, 14, or 15 carbon atoms, and substituted or unsubstituted heteroaryl groups having 12, 13, 14, 15, 16, 17, or 18 carbon atoms.
[0104] Optionally, the substituents in L1, L2 and L are each independently selected from deuterium, fluorine, cyano, alkyl with 1 to 5 carbon atoms, trialkylsilyl with 3 to 8 carbon atoms, fluoroalkyl with 1 to 4 carbon atoms, deuterated alkyl with 1 to 4 carbon atoms, phenyl or naphthyl.
[0105] In some embodiments, L1, L2, and L may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted fluorene, substituted or unsubstituted phenanthylene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuran, and substituted or unsubstituted carbazolyl.
[0106] Optionally, the substituents in L1, L2 and L may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl or phenyl.
[0107] In some embodiments, L is selected from the group consisting of single bonds or the following groups:
[0108]
[0109] In some embodiments, L is selected from the group consisting of single bonds or the following groups:
[0110]
[0111] In some embodiments, L1 and L2 are each independently selected from the group consisting of single bonds or the following groups:
[0112]
[0113] In some embodiments, L1 and L2 are each independently selected from the group consisting of single bonds or the following groups:
[0114]
[0115] In some implementations... Each is independently selected from the following groups:
[0116]
[0117]
[0118] In some implementations, in Equation 2 Selected from the following groups:
[0119]
[0120]
[0121] In some embodiments, the organic compound is selected from the structures shown in formulas (2-1) to (2-5).
[0122]
[0123]
[0124] In some embodiments, the organic compounds of this application are selected from the group consisting of:
[0125]
[0126]
[0127]
[0128]
[0129]
[0130]
[0131]
[0132]
[0133]
[0134]
[0135] A second aspect of this application provides an organic electroluminescent device, including an anode, a cathode, and a functional layer disposed between the anode and the cathode; wherein the functional layer comprises the organic compound described in the first aspect of this application.
[0136] The organic compounds provided in this application can be used to form at least one organic film layer in the functional layer to improve the luminous efficiency and lifetime of organic electroluminescent devices.
[0137] Optionally, the functional layer includes an organic light-emitting layer, which comprises the organic compound. The organic light-emitting layer may be composed of the organic compound provided in this application, or it may be composed of the organic compound provided in this application and other materials.
[0138] According to one specific embodiment, the organic electroluminescent device, such as Figure 1 As shown, an organic electroluminescent device may include an anode 100, a hole injection layer 310, a first hole transport layer 321, a second hole transport layer (also called a hole auxiliary layer) 322, an organic light-emitting layer 330, an electron transport layer 340, an electron injection layer 350, and a cathode 200, which are stacked sequentially.
[0139] In this application, the anode 100 includes an anode material, which is preferably a material with a large work function that facilitates hole injection into the functional layer. Specific examples of anode materials include: metals such as nickel, platinum, vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; or conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, and polyaniline, but are not limited thereto. Preferably, a transparent electrode comprising indium tin oxide (ITO) as the anode is included.
[0140] In this application, the first hole transport layer may include one or more hole transport materials. The first hole transport layer material may be selected from carbazole polymers, carbazole-linked triarylamine compounds, or other types of compounds, specifically from the compounds listed below or any combination thereof:
[0141]
[0142] In one embodiment, the first hole transport layer 321 is composed of HT-1.
[0143] In one embodiment, the second hole transport layer 322 is composed of HT-2.
[0144] Optionally, a hole injection layer 310 is further provided between the anode 100 and the first hole transport layer 321 to enhance the ability to inject holes into the first hole transport layer 321. The hole injection layer 310 can 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 be selected from, for example, the following compounds or any combination thereof;
[0145]
[0146]
[0147] In one embodiment, the hole injection layer 310 is composed of PD and HT-1.
[0148] In this application, the organic light-emitting layer 330 can be composed of a single light-emitting material, or it can include a host material and a guest material. Optionally, the organic light-emitting layer 330 is composed of a host material and a guest material. Holes and electrons injected into the organic light-emitting layer 330 can recombine in the organic light-emitting layer 330 to form excitons. The excitons transfer energy to the host material, and the host material transfers energy to the guest material, thereby enabling the guest material to emit light.
[0149] The host material of the organic light-emitting layer 330 may include metal chelating compounds, bis(styrene) derivatives, aromatic amine derivatives, dibenzofuran derivatives, or other types of materials. Optionally, the host material may include the organic compounds of this application.
[0150] The guest material of the organic light-emitting layer 330 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. Specific examples of phosphorescent dopant include, but are not limited to,
[0151]
[0152]
[0153] In one embodiment of this application, the organic electroluminescent device is a red organic electroluminescent device. In one embodiment, the host material of the organic light-emitting layer 330 comprises the organic compound of this application. The guest material is, for example, RD. In another embodiment, the host material of the organic light-emitting layer 330 comprises the organic compound of this application and RH-P. The object material is, for example, RD.
[0154] In one embodiment of this application, the organic electroluminescent device is a green organic electroluminescent device. In a more specific embodiment, the host material of the organic light-emitting layer 330 comprises the organic compound of this application. The guest material is, for example, fac-Ir(ppy)3.
[0155] The electron transport layer 340 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, BTB, LiQ, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials. This application does not impose any specific limitations on these materials. The material of the electron transport layer 340 includes, but is not limited to, the following compounds:
[0156]
[0157] In one embodiment of this application, the electron transport layer 340 may be composed of ET and LiQ.
[0158] 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.
[0159] Optionally, an electron injection layer 350 is further disposed between the cathode 200 and the electron transport layer 340 to enhance the ability to inject electrons into the electron transport layer 340. The electron injection layer 350 may include inorganic materials such as alkali metal sulfides and alkali metal halides, or may include complexes of alkali metals and organic materials. In one embodiment of this application, the electron injection layer 350 may include ytterbium (Yb).
[0160] A third aspect of this application provides an electronic device including the organic electroluminescent device described in the second aspect of this application.
[0161] 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.
[0162] The following examples illustrate the synthesis method of the organic compounds of this application, but this disclosure is not limited thereto.
[0163] Synthesis Examples
[0164] 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. The compounds synthesized by methods not mentioned in this application are all commercially available starting materials.
[0165] Synthesis of Sub-a1:
[0166]
[0167] Under a nitrogen atmosphere, 1-bromo-3-hydroxynaphthalene (11.1 g, 50 mmol), benzylamine (10.71 g, 100 mmol), ammonium persulfate (22.82 g, 100 mmol), 2,2,6,6-tetramethylpiperidine oxide (TEMPO, 15.63 g, 100 mmol), and acetonitrile (150 mL) were added sequentially to a 250 mL three-necked flask. Stirring and heating were initiated, and the mixture was heated to 50 °C and stirred for 24 h. After the system cooled to room temperature, it was extracted with dichloromethane (100 mL × 3 times). The organic phases were combined and dried over anhydrous magnesium sulfate. After filtration, the solvent was removed by vacuum distillation to obtain the crude product. The crude product was purified by silica gel column chromatography using ethyl acetate / n-heptane as the mobile phase to obtain a grayish-white solid, Sub-a1 (11.0 g, yield 68%).
[0168] Referring to the synthesis of Sub-a1, Sub-a2 to Sub-a5 were synthesized by replacing benzylamine with reactant A shown in Table 1 and 1-bromo-3-hydroxynaphthalene with reactant B.
[0169] Table 1: Synthesis of Sub-a2 and Sub-a3
[0170]
[0171] Synthesis of Sub-b1:
[0172]
[0173] Under a nitrogen atmosphere, Sub-a1 (16.20 g, 50 mmol), 5-chloro-2-carboxyphenylboronic acid (10.14 g, 55 mmol), tetrakis(triphenylphosphine)palladium (0.58 g, 0.5 mmol), anhydrous sodium carbonate (10.60 g, 100 mmol), toluene (160 mL), anhydrous ethanol (40 mL), and deionized water (40 mL) were added sequentially to a 500 mL three-necked flask. Stirring and heating were initiated, and the mixture was refluxed for 8 h. After cooling to room temperature, the mixture was extracted with dichloromethane (100 mL × 3 times). The organic phases were combined and dried over anhydrous magnesium sulfate. After filtration, the solvent was removed by vacuum distillation to obtain the crude product. The crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as the mobile phase to obtain a white solid (12.85 g, yield 67%).
[0174] Referring to the synthesis of Sub-a1, Sub-b2 to Sub-b7 were synthesized by replacing Sub-a1 with reactant C shown in Table 2 and replacing 5-chloro-2-formylphenylboronic acid with reactant D.
[0175] Table 2: Synthesis of Sub-b2 to Sub-b7
[0176]
[0177] Synthesis of Sub-c1:
[0178]
[0179] Under a nitrogen atmosphere, Sub-b1 (49.9 g, 130 mmol), (methoxymethyl)triphenylphosphonium chloride (74.38 g, 217 mmol), and anhydrous tetrahydrofuran (500 mL) were added sequentially to a 1000 mL three-necked flask. The system was cooled to 0 °C using an ice-water bath. Then, an anhydrous tetrahydrofuran solution of potassium tert-butoxide (1 M, 220 mL) was slowly added dropwise. After the addition was complete, the system was slowly heated to room temperature, and the reaction was stirred for 6 h. The reaction solution was poured into 1000 mL of deionized water and extracted with ethyl acetate (250 mL × 3 times). The organic phases were combined and dried over anhydrous magnesium sulfate. After filtration, 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 as the mobile phase to obtain a white solid (41.76 g, yield 78%).
[0180] Following the synthesis procedure of Sub-c1, reactant E shown in Table 3 was used to replace Sub-b1 to synthesize Sub-c2 to Sub-c7.
[0181] Table 3: Synthesis of Sub-c2 to Sub-c7
[0182]
[0183] Synthesis of Sub-d1:
[0184]
[0185] Under a nitrogen atmosphere, Sub-Cl (49.0 g, 119 mmol), Eaton reagent (4.5 mL), and chlorobenzene (500 mL) were added sequentially to a 1000 mL three-necked flask. The mixture was heated to reflux and stirred for 4 h. After the reaction system cooled to room temperature, the reaction solution was poured into 1000 mL of deionized water, neutralized with saturated sodium hydroxide solution, and then extracted with dichloromethane (250 mL × 3 times). The organic phases were combined, dried over anhydrous magnesium 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 dichloromethane / n-heptane as the mobile phase to obtain a solid (24.0 g, yield 53%).
[0186] Referring to the synthesis of Sub-d1, Sub-d2 to Sub-d7 were synthesized by replacing Sub-c1 with reactant F shown in Table 4.
[0187] Table 4: Synthesis of Sub-d2 to Sub-d7
[0188]
[0189]
[0190] Synthesis of Sub-e1:
[0191]
[0192] Under a nitrogen atmosphere, Sub-d1 (19.0 g, 50 mmol), pinacol diborate (14.0 g, 55 mmol), potassium acetate (10.8 g, 110 mmol), and 1,4-dioxane (160 mL) were added sequentially to a 500 mL three-necked flask. The mixture was stirred and heated until it reached 40 °C. Then, tris(dibenzylideneacetone)dipalladium (Pd2(dba)3, 0.46 g, 0.50 mmol) and 2-dicyclohexylphosphine-2',4',6'triisopropylbiphenyl (XPhos, 0.48 g, 1.0 mmol) were quickly added. The mixture was then heated to reflux and stirred overnight. After the system cooled to room temperature, 200 mL of water was added to the system and stirred thoroughly for 30 min. The mixture was then filtered under reduced pressure. The filter cake was washed with deionized water until neutral and then rinsed with 100 mL of anhydrous ethanol to obtain a gray solid. The crude product was slurried once with n-heptane, then dissolved in 200 mL of toluene and passed through a silica gel column to remove the catalyst. After concentration, a white solid Sub-e1 (14.85 g, yield 63%) was obtained.
[0193] Referring to the synthesis of Sub-e1, Sub-e2 to Sub-e7 were synthesized by replacing Sub-d1 with reactant G shown in Table 5.
[0194] Table 5: Synthesis of Sub-e2 to Sub-e7
[0195]
[0196] Synthesis of compound 11:
[0197]
[0198] Under a nitrogen atmosphere, Sub-e1 (11.78 g, 25 mmol), RM-1 (9.85 g, 25 mmol), tetra(triphenylphosphine)palladium (0.29 g, 0.25 mmol), anhydrous potassium carbonate (6.9 g, 50 mmol), tetrabutylammonium bromide (0.8 g, 2.5 mmol), toluene (120 mL), tetrahydrofuran (30 mL), and deionized water (30 mL) were added sequentially to a 250 mL three-necked flask. Stirring and heating were started, and the mixture was refluxed for 16 h. After the system cooled to room temperature, it was extracted with dichloromethane (100 mL × 3 times). The organic phases were combined, dried over anhydrous magnesium 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 dichloromethane / n-heptane as the mobile phase to give a white solid compound 11 (9.31 g, yield 53%, m / z = 703.24 [M+H]). + ).
[0199] Referring to the synthesis of compound 11, reactant H was used instead of Sub-e1 and reactant J was used instead of RM-1 as shown in Table 6 to synthesize the compounds of this application in Table 6.
[0200] Table 6: Synthesis of the compounds in this application
[0201]
[0202]
[0203]
[0204]
[0205]
[0206]
[0207]
[0208] NMR of Compound 61: 1H-NMR(400MHz,Methylene-Chloride-D2)δppm 9.67(s,1H),8.87(d,1H),8.81(s,2H),8.63-8.59(m,2H),8.53(d,2H),8.3 1(d,2H),8.27-8.23(m,2H),8.13(d,2H),8.08(d,2H),8.03(d,1H),7.96(d 2H),7.80(t,1H),7.64(t,2H),7.57(t,2H),7.49(t,2H),7.40-7.32(m,2H).
[0209] Fabrication and evaluation of organic electroluminescent devices:
[0210] Example 1: Red Organic Electroluminescent Device
[0211] First, anodizing pretreatment is performed through the following process: [The process is repeated in the original text, so the translation is incomplete.] On the ITO / Ag / ITO substrate, surface treatment is performed using ultraviolet ozone and O2:N2 plasma to increase the work function of the anode. Alternatively, organic solvents can be used to clean the surface of the ITO substrate to remove impurities and oil stains.
[0212] On the experimental substrate (anode), PD:HT-1 was co-deposited at a deposition rate of 2%:98% to form a thickness of [missing information]. A hole injection layer (HIL) is formed, and then HT-1 is vacuum-deposited on the hole injection layer to form a thickness of [missing information]. A hole transport layer. Compound HT-2 is vacuum-deposited onto the first hole transport layer to form a layer with a thickness of [missing information]. Second hole transport layer
[0213] Next, on the second hole transport layer, compound 11:RH-P:RD was co-deposited in a ratio of 49%:49%:2% to form a layer with a thickness of [missing information]. The red light-emitting layer (EML)
[0214] On the light-emitting layer, compounds ET and LiQ are co-deposited at a 1:1 evaporation rate to form... A thick electron transport layer (ETL) is formed by depositing Yb onto the electron transport layer to create a layer with a thickness of [thickness value missing]. An electron-injected layer (EIL) was formed, and then magnesium (Mg) and silver (Ag) were mixed at a evaporation rate of 1:9 and vacuum-deposited onto the electron-injected layer to form a layer with a thickness of [missing information]. The cathode.
[0215] Furthermore, the vacuum evaporation thickness on the aforementioned cathode is [missing information]. The CP is used to complete the fabrication of a red organic electroluminescent device.
[0216] Examples 2-37
[0217] Except that, when fabricating the light-emitting layer, compound X in Table 7 is used instead of compound 11 in Example 1, the organic electroluminescent device is prepared using the same method as in Example 1.
[0218] Comparative Examples 1-4
[0219] Except that, when fabricating the light-emitting layer, compounds A, B, C, and D were used instead of compound 11 in Example 1, the organic electroluminescent device was prepared using the same method as in Example 1.
[0220] The structures of the compounds used in the various embodiments and comparative examples are as follows:
[0221]
[0222] The performance of the red organic electroluminescent devices prepared in Examples 1-37 and Comparative Examples 1-4 was tested, specifically at 10 mA / cm². 2 The IVL performance of the device was tested under the following conditions: T 95 Device lifetime is 20 mA / cm 2 The test was conducted under the specified conditions, and the test results are shown in Table 7.
[0223] Table 7
[0224]
[0225]
[0226] Referring to Table 7 above, when the compounds of the present invention are used as the main material of red organic electroluminescent devices, the luminous efficiency Cd / A is increased by at least 12.3%, and the T95 lifetime is increased by at least 12.8%.
[0227] The reason for this is that the compound structure of this application contains a core structure of benzo[a]phenanthrene-oxazole / thiazole, with an electron-transfer group attached to the core, making it suitable as an electron-transporting red light host material. The benzo[a]phenanthrene-oxazole / thiazole has a large conjugated system; connecting it to the electron-transfer group enhances intermolecular forces and increases the compound's carrier mobility. When this compound is used as an electron-transporting material in a hybrid host material, it can improve carrier balance in the emitting layer, broaden the carrier recombination region, improve exciton generation and utilization efficiency, and ultimately enhance the device's luminous efficiency and lifetime.
[0228] The preferred embodiments of the present invention have been described in detail above with reference to the accompanying drawings. However, the present invention is not limited to the specific details of the above embodiments. Within the scope of the technical concept of the present invention, various simple modifications can be made to the technical solution of the present invention, and these simple modifications all fall within the protection scope of the present invention.
Claims
1. Organic compound, characterized in that, It has the structure shown in Equation 1: Formula 1 wherein one of X and Y is O and the other is ; Each R1 and R3 may be the same or different, and are independently selected from hydrogen, deuterium or the group shown in Formula 2, and there is one and only one of each R1 and R3 that is the group shown in Formula 2; Each R2 is independently selected from hydrogen or deuterium; Formula 2 n1 is the number of R1s, selected from 0, 1, 2, 3 or 4; when n1 is greater than 1, any two R1s are the same or different. n2 is the number of R2, selected from 0, 1 or 2; when n2 is greater than 1, any two R2 are the same or different; n3 is the number of R3s, selected from 0, 1, 2, 3 or 4; when n3 is greater than 1, any two R3s are the same or different. Z1, Z2 and Z3 are each independently selected from C(H) or N, and at least two of Z1, Z2 and Z3 are N; L is selected from single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene; L1 and L2 may be the same or different, and each is independently selected from single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl. The substituents in L1, L2 and L may be the same or different, and each is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl or phenyl; Ar1 and Ar2 are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl; The substituents in Ar1 and Ar2 are each independently selected from deuterium, fluorine, cyano, trideuterated methyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, and naphthyl. Ar3 is selected from substituted or unsubstituted phenyl groups and substituted or unsubstituted naphthyl groups; The substituents in Ar3 are each independently selected from deuterium, fluorine, cyano, trideuterated methyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, and phenyl. and the organic compound is not 。 2. The organic compound according to claim 1, wherein One of R1 has the structure shown in Equation 2, and the remaining R1 and each R3 are independently selected from hydrogen and deuterium; or One of R3 has the structure shown in Equation 2, and the remaining R3 and each R1 are independently selected from hydrogen and deuterium.
3. The organic compound according to claim 1, wherein Ar1 and Ar2 are each independently selected from substituted or unsubstituted groups W; wherein the unsubstituted group W is selected from the group consisting of: ; The substituted group W has one or more substituents, and each substituent on the substituted group W is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, phenyl, and naphthyl. When the number of substituents on the group W is greater than 1, the substituents may be the same or different.
4. The organic compound according to claim 1, wherein Ar3 is selected from substituted or unsubstituted groups Q; wherein the unsubstituted group Q is selected from the group consisting of: ; The substituted group Q has one or more substituents, and the substituents on the substituted group Q are each independently selected from deuterium, fluorine, methyl, ethyl, isopropyl, tert-butyl, and phenyl. When the number of substituents on the group Q is greater than 1, the substituents may be the same or different.
5. The organic compound according to claim 1, wherein Ar1 and Ar2 may be the same or different, and each is independently selected from the following groups: 。 6. The organic compound according to claim 1, wherein Ar3 is selected from the following groups: 。 7. The organic compound according to claim 1, wherein L is selected from the group consisting of single bonds or the following groups: 。 8. The organic compound according to claim 1, wherein L1 and L2 are each independently selected from the group consisting of single bonds or the following groups: 。 9. The organic compound according to claim 1, wherein and each independently is selected from the group consisting of: 。 10. The organic compound according to claim 1, wherein, in formula 2 is selected from the group consisting of 。 11. The organic compound according to claim 1, wherein The organic compound is selected from the group consisting of the following compounds: 。 12. An organic electroluminescent device, comprising an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; characterized in that, The functional layer comprises any one of the organic compounds according to claims 1 to 11.
13. The organic electroluminescent device according to claim 12, characterized in that The functional layer includes an organic light-emitting layer, which contains the organic compound.
14. An electronic device, characterized by Including the organic electroluminescent device as described in claim 12 or 13.