Organic compounds, organic electroluminescent devices, and electronic devices
Patent Information
- Application Number
- CN202611080975.9
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Filing Date
- 2026-07-20
- Publication Date
- 2026-10-30
- Estimated Expiration
- 2046-07-20
AI Technical Summary
[0004]本申请的目的在于提供一种有机化合物、有机电致发光器件和电子装置,以解决现有敏化剂单线态-三线态能级差相对较大的问题,并减少分子间堆积,提升有机电致发光器件的发光效率
[0010]通过上述技术方案,本申请提供一种含双螺芴硼碳类结构的有机化合物,该有机化合物包含氮杂苯或其衍生物、芳胺或其衍生物、咔唑或其衍生物或者是恶嗪衍生物,且氮杂苯或其衍生物、芳胺或其衍生物、咔唑或其衍生物或者是恶嗪衍生物连接在与硼原子直接相连的苯环或氮杂环上,有利于提高反向系间窜越速率(krisc),使三线态激子能够高效转化为发光单线态激子,从而提高器件发光效率;同时,两个螺芴结构分别设于与硼原子直接相连的苯环或氮杂环的两侧,氮杂苯或其衍生物、芳胺或其衍生物、咔唑或其衍生物或者是恶嗪衍生物增加了空间位阻和化合物的刚性,从而可以有效阻止分子间堆叠,进一步提高了激子生成和利用效率,进而进一步提高器件发光效率。
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Figure CN122586936B_ABST
Abstract
Description
Technical Field
[0001] This application belongs to the field of solar cells, specifically relating to an organic compound, an organic electroluminescent device, and an electronic device. Background Technology
[0002] Multiple resonance thermally activated delayed fluorescence (MR-TADF) materials, with their unique molecular resonance framework, perfectly combine narrow-band emission with high radiative decay rates. However, they suffer from drawbacks such as efficiency roll-off and aggregation quenching. To address these issues, the thermally activated sensitized fluorescence (TSF) mechanism has been proposed. This mechanism uses conventional TADF materials as sensitizers to recover triplet excitons and transfer them to MR-TADF via Foster resonance energy transfer (FRET), while retaining the narrow-band advantage of MR-TADF.
[0003] However, traditional DA-type TADF sensitizers exhibit a singlet-triplet energy level difference (ΔE). ST The relatively large problem leads to a reverse intersystem crossing rate (k) risc The luminescence process is slower and the excited-state lifetime is longer, which leads to a decrease in the luminous efficiency of organic electroluminescent devices. Summary of the Invention
[0004] The purpose of this application is to provide an organic compound, an organic electroluminescent device, and an electronic device to solve the problem of the relatively large singlet-triplet energy level difference in existing sensitizers, reduce intermolecular stacking, and improve the luminous efficiency of organic electroluminescent devices.
[0005] To achieve the above objectives, a first aspect of this application provides an organic compound having a structure selected from that shown in Formula I:
[0006] Among them, X1 and X2 may be the same or different, and each is independently selected from C(R). a ) or N; R a R1, R2, R3, R4, R5, R6, and R7 may be the same or different, and each is independently selected from hydrogen, deuterium, halogen, cyano, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, substituted or unsubstituted bridged cycloalkyl with 4 to 30 carbon atoms, substituted or unsubstituted aryl with 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl with 3 to 40 carbon atoms, or group Q, and at least one of R1, R2, and R3 is selected from group Q; wherein group Q has the structure shown in formula I-1, formula I-2, formula I-3, formula I-4, or formula I-5;
[0007] In formulas I-1, I-2, I-3, I-4, or I-5, " " indicates the connection site with Equation I, where X3 and X4 may be the same or different, and each is independently selected from C(R) b ) or N; L1, L2, L3, L4, L5, and L6 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, or substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms. Ar1, Ar2, Ar3 and Ar4 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms. Rings C, D, E, and F may be the same or different, and each is independently selected from an aromatic ring having 6 to 30 carbon atoms or a heteroaromatic ring having 3 to 30 carbon atoms; optionally, when R1 and / or R2 are selected from formula I-5, formula I-5 is ring-fused with the ring of formula I. R b Each R8, each R9, each R 10 Each R 11 They may be the same or different, and each is independently selected from hydrogen, deuterium, halogen, cyano, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, substituted or unsubstituted aryl with 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl with 3 to 40 carbon atoms. n1 is the number of substituents R1, and n1 is 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 substituents R2, and n2 is selected from 0, 1, 2, 3 or 4. When n2 is greater than 1, any two R2s are the same or different. n4 is the number of substituents R4, and n4 is selected from 0, 1, 2, 3 or 4. When n4 is greater than 1, any two R4s are the same or different. n5 is the number of substituents R5, and n5 is selected from 0, 1, 2, 3 or 4. When n5 is greater than 1, any two R5s are the same or different. n6 is the number of substituents R6, and n6 is selected from 0, 1, 2, 3 or 4. When n6 is greater than 1, any two R6s are the same or different. n7 is the number of substituents R7, which can be selected from 0, 1, 2, 3 or 4. When n7 is greater than 1, any two R7s can be the same or different. n8 is the number of substituents R8, which is selected from 0 to the maximum number of substitutable elements. When n8 is greater than 1, any two R8s are the same or different. Optionally, any two adjacent R8s are connected to form a substituted or unsubstituted 6- to 15-membered ring X. n9 is the number of substituents R9, which is selected from 0 to the maximum number of substitutable elements. When n9 is greater than 1, any two R9s are the same or different. Optionally, any two adjacent R9s are connected to form a substituted or unsubstituted 6- to 15-membered ring Y. n 10 Indicates substituent R 10 The number of n 10 Selected from 0 to the largest substitutable number, when n 10 When greater than 1, any two R 10 Same or different; optionally, any two adjacent n 10 The links between them form substituted or unsubstituted 6-15 membered rings Z; n 11 Indicates substituent R 11 The number of n 11 Selected from 0 to the largest substitutable number, when n 11 When greater than 1, any two R 11 Same or different; optionally, any two adjacent R 11 The links between them form substituted or unsubstituted 6-15 membered rings W; R a R b Each R1, each R2, each R3, each R4, each R5, each R6, each R7, each R8, each R9, each R 10 Each R 11 The substituents in L1, L2, L3, L4, L5, L6, Ar1, Ar2, Ar3, and Ar4 may be the same or different, and each is independently selected from deuterium, halogen, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, cycloalkyl with 3 to 10 carbon atoms, aryl with 6 to 20 carbon atoms, and heteroaryl with 3 to 20 carbon atoms.
[0008] A second aspect of this application provides an organic electroluminescent device, including a cathode and an anode disposed opposite to each other, and a functional layer disposed between the cathode and the anode, the functional layer comprising the organic compound described in the first aspect of this application.
[0009] A third aspect of this application provides an electronic device, the electronic device including the organic electroluminescent device described in the second aspect of this application.
[0010] Through the above technical solution, this application provides an organic compound containing a double spirofluorene boron-carbon structure. This organic compound contains azirbenzene or its derivatives, aromatic amines or their derivatives, carbazole or its derivatives, or oxazine derivatives. The azirbenzene or its derivatives, aromatic amines or their derivatives, carbazole or its derivatives, or oxazine derivatives are connected to the benzene ring or azirene ring directly connected to the boron atom, which is beneficial to improve the reverse intersystem crossing rate (Krisc), enabling triplet excitons to be efficiently converted into luminescent singlet excitons, thereby improving the luminescence efficiency of the device. At the same time, the two spirofluorene structures are respectively located on both sides of the benzene ring or azirene ring directly connected to the boron atom. The azirbenzene or its derivatives, aromatic amines or their derivatives, carbazole or its derivatives, or oxazine derivatives increase the steric hindrance and rigidity of the compound, thereby effectively preventing intermolecular stacking, further improving the exciton generation and utilization efficiency, and thus further improving the luminescence efficiency of the device.
[0011] Other features and advantages of this application will be described in detail in the following detailed description section. Attached Figure Description
[0012] The accompanying drawings are provided to further illustrate the present application and form part of the specification. They are used together with the following detailed description to explain the present application, but do not constitute a limitation thereof. In the drawings: Figure 1 This is a schematic diagram of the structure of an organic electroluminescent device according to one embodiment of this application.
[0013] Explanation of reference numerals in the attached figures: 100, Anode; 200, Cathode; 300, Functional layer; 310, Hole injection layer; 320, Hole transport layer; 321, First hole transport layer; 322, Second hole transport layer; 330, Organic light-emitting layer; 340, Hole blocking layer; 350, Electron transport layer; 360, Electron injection layer. Detailed Implementation
[0014] The specific embodiments of this application are described in detail below. It should be understood that the specific embodiments described herein are for illustration and explanation only and are not intended to limit this application.
[0015] 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 R2 groups may connect to form a ring" includes: a scenario where any two adjacent substituents R2 form a ring, and a scenario where any two adjacent substituents R2 exist independently without forming a ring. "Any two adjacent" can include having two substituents on the same atom, or having one substituent on each of two adjacent atoms; wherein, when there are two substituents on the same atom, the two substituents may 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 may fuse to form a ring.
[0016] In this application, the terms "optionally", "preferredly", and "in some embodiments" have the same meaning.
[0017] In this application, a ring system consisting of n atoms is called an n-membered ring. When the ring is substituted by a substituent, the number of atoms contained in the substituent is not included in "n". For example, a substituted or unsubstituted phenyl group is a 6-membered aryl group, a substituted or unsubstituted naphthalene ring is a 10-membered aryl ring, and a substituted or unsubstituted benzofuran ring is a 9-membered ring. These are not listed here.
[0018] 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, " "and" In the formula Q-1, each q is independently 0, 1, 2 or 3, and each R is independently selected from hydrogen, deuterium, fluorine or chlorine. The meaning is: Formula Q-1 represents 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 represents that there are q substituents R" on each benzene ring of biphenyl. The number of substituents q on the two benzene rings R" 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.
[0019] In this application, the term "substituted or unsubstituted" means that the functional group described after the term may or may not have substituents. For example, "substituted or unsubstituted aryl" refers to an aryl group with substituents or an aryl group without substituents. The substituents mentioned above can be, for example, deuterium, fluorine, cyano, heteroaryl, aryl, deuterated aryl, alkyl, haloalkyl, deuterated alkyl, cycloalkyl, etc. The number of substituents can be one or more.
[0020] In this application, "multiple" means two or more, such as two, three, four, five, six, etc.
[0021] In this application, the number of carbon atoms in a substituted or unsubstituted functional group refers to the total number of carbon atoms in that group, including the substituents. For example, if L1 is a substituted arylene with 18 carbon atoms, then the total number of carbon atoms in the arylene and its substituents is 18.
[0022] The hydrogen atoms in the compound structure of this application include various isotopes of hydrogen, such as hydrogen (H), deuterium (D), or tritium (T).
[0023] In this application, the bridged cycloalkyl group, whether substituted or unsubstituted, may have 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 carbon atoms. For example, the bridged cycloalkyl group may include adamantyl alkyl.
[0024] 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 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 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 include, but are not limited to, phenyl, naphthyl, fluorenyl, spirodifluorenyl, anthracene, phenanthryl, biphenyl, terphenyl, tetraphenyl, pentaphenyl, triphenylene, perylene, benzo[9,10]phenanthryl, pyrene, benzofluoranthryl, phenylene, etc. Furthermore, alicyclic aromatic hydrocarbons are also classified as aryl in this application, such as substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydroanthryl, substituted or unsubstituted indenyl, substituted or unsubstituted acenaphthene, etc., which are also within the scope of aryl groups described in this application.
[0025] In this application, the substituted aryl group can be one or more hydrogen atoms of the aryl group that are substituted by groups such as deuterium, halogen groups, cyano, aryl, deuterated aryl, heteroaryl, trialkylsilyl, alkyl, haloalkyl, deuterated alkyl, etc. Specific examples of heteroaryl-substituted aryl groups include, but are not limited to, dibenzofuranyl-substituted phenyl, dibenzothiophene-substituted phenyl, pyridine-substituted phenyl, etc. It should be understood that the number of carbon atoms in the substituted aryl group refers to the total number of carbon atoms of the aryl group and the substituents on the aryl group. For example, a substituted aryl group with 18 carbon atoms means that the total number of carbon atoms of the aryl group and the substituents is 18.
[0026] 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 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, benzimidazolyl, benzothiazolyl, benzocarbazoleyl, benzothiaphenyl, dibenzothiaphenyl, thiaphenothiaphenyl, benzofuranyl, phenanthrololinyl, isoxazolyl, thiadiazolyl, phenthiaazinyl, silfluorenyl, dibenzofuranyl, and N -Phenylacetazolyl, N -pyridylcarbazole group, N- Methylcarbazolyl, etc., but not limited to these.
[0027] 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, haloalkyl groups, deuteralkyl groups, etc. Specific examples of aryl-substituted heteroaryl groups include, but are not limited to, N -Phenyl-substituted carbazolyl, etc. It should be understood that the number of carbon atoms in a substituted heteroaryl group refers to the total number of carbon atoms in the heteroaryl group and the substituents on the heteroaryl group.
[0028] In this application, the number of carbon atoms in the substituted or unsubstituted aryl group can be 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 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 20 carbon atoms; in still other embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group with 6 to 18 carbon atoms; in yet another embodiment, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group with 6 to 15 carbon atoms; and in some embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group with 6 to 12 carbon atoms.
[0029] 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, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39 or 40. In some embodiments, the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group with a total carbon number of 3 to 40; in some embodiments, the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group with a total carbon number of 12 to 40; in some embodiments, the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group with a total carbon number of 3 to 30; in still other embodiments, the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group with a total carbon number of 3 to 20; in still other embodiments, the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group with a total carbon number of 3 to 18; and in still other embodiments, the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group with a total carbon number of 3 to 12.
[0030] In this application, arylene refers to a divalent group derived from an aromatic carbon ring in an aromatic hydrocarbon. The number of carbon atoms in a substituted or unsubstituted arylene can be 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 arylene is a substituted or unsubstituted arylene with 6 to 30 carbon atoms; in other embodiments, the substituted or unsubstituted arylene is a substituted or unsubstituted arylene with 6 to 20 carbon atoms; in yet another embodiment, the substituted or unsubstituted arylene is a substituted or unsubstituted arylene with 6 to 18 carbon atoms; in still another embodiment, the substituted or unsubstituted arylene is a substituted or unsubstituted arylene with 6 to 15 carbon atoms; and in some embodiments, the substituted or unsubstituted arylene is a substituted or unsubstituted arylene with 6 to 12 carbon atoms.
[0031] In this application, a heteroaryl group refers to a divalent group derived from a heteroaryl hydrocarbon. The number of carbon atoms in a substituted or unsubstituted heteroaryl group can be 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 group is a substituted or unsubstituted heteroaryl group having 6 to 30 carbon atoms; in other embodiments, the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group having 6 to 20 carbon atoms; in yet another embodiment, the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group having 6 to 18 carbon atoms; in still another embodiment, the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group having 6 to 15 carbon atoms; and in some embodiments, the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group having 6 to 12 carbon atoms.
[0032] In this application, the number of carbon atoms of the aryl group as a substituent can be 6 to 30, for example, the number of carbon atoms can be 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29 or 30. Specific examples of the aryl group as a substituent include, but are not limited to, phenyl, biphenyl, naphthyl, anthracene, hydroxyl or tetrahydronaphthyl.
[0033] In this application, the number of carbon atoms in the heteroaryl group used as a substituent can be 3 to 30, for example, the number of carbon atoms can be 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29 or 30. Specific examples of heteroaryl groups used as substituents include, but are not limited to, pyridinyl, pyrimidinyl, carbazoleyl, etc. N -Phenylcarbazolyl, dibenzofuranyl, dibenzothiophenyl, quinolinyl, quinazolinyl, quinoxalinyl, or isoquinolinyl.
[0034] In this application, the number of carbon atoms in alkyl groups having 1 to 10 carbon atoms can be, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10. Specific examples of alkyl groups include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, nonyl, decyl, 3,7-dimethyloctyl, etc.
[0035] In this application, the halogen group can be fluorine, chlorine, bromine or iodine.
[0036] In this application, halogenated alkyl refers to halogen-substituted alkyl groups.
[0037] In this application, the number of carbon atoms in the alkyl halogroup is, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10. Specific examples of alkyl halogroups include, but are not limited to, trifluoromethyl.
[0038] In this application, " "" refers to a chemical bond that is attached to other substituents or binding sites.
[0039] In this application, a non-positioned linker bond refers to a single bond extending from the ring system. The term "" indicates that one end of the linker bond can connect to any position in the ring system that the bond penetrates, while the other end connects to the rest of the compound molecule.
[0040] For 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. .
[0041] In a first aspect, this application provides an organic compound having the structure shown in Formula I:
[0042] Among them, X1 and X2 may be the same or different, and each is independently selected from C(R). a ) or N; R a R1, R2, R3, R4, R5, R6, and R7 may be the same or different, and each is independently selected from hydrogen, deuterium, halogen, cyano, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, substituted or unsubstituted bridged cycloalkyl with 4 to 30 carbon atoms, substituted or unsubstituted aryl with 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl with 3 to 40 carbon atoms, or group Q, and at least one of R1, R2, and R3 is selected from group Q; wherein group Q has the structure shown in formula I-1, formula I-2, formula I-3, formula I-4, or formula I-5;
[0043] In formulas I-1, I-2, I-3, I-4, or I-5, " " indicates the connection site with Equation I, where X3 and X4 may be the same or different, and each is independently selected from C(R) b ) or N; L1, L2, L3, L4, L5, and L6 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, or substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms. Ar1, Ar2, Ar3 and Ar4 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms. Rings C, D, E, and F may be the same or different, and each is independently selected from an aromatic ring having 6 to 30 carbon atoms or a heteroaromatic ring having 3 to 30 carbon atoms; optionally, when R1 and / or R2 are selected from formula I-5, formula I-5 is ring-fused with the ring of formula I. R b Each R8, each R9, each R 10 Each R 11 They may be the same or different, and each is independently selected from hydrogen, deuterium, halogen, cyano, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, substituted or unsubstituted aryl with 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl with 3 to 40 carbon atoms. n1 is the number of substituents R1, and n1 is 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 substituents R2, and n2 is selected from 0, 1, 2, 3 or 4. When n2 is greater than 1, any two R2s are the same or different. n4 is the number of substituents R4, and n4 is selected from 0, 1, 2, 3 or 4. When n4 is greater than 1, any two R4s are the same or different. n5 is the number of substituents R5, and n5 is selected from 0, 1, 2, 3 or 4. When n5 is greater than 1, any two R5s are the same or different. n6 is the number of substituents R6, and n6 is selected from 0, 1, 2, 3 or 4. When n6 is greater than 1, any two R6s are the same or different. n7 is the number of substituents R7, which can be selected from 0, 1, 2, 3 or 4. When n7 is greater than 1, any two R7s can be the same or different. n8 is the number of substituents R8, which is selected from 0 to the maximum number of substitutable elements. When n8 is greater than 1, any two R8s are the same or different. Optionally, any two adjacent R8s are connected to form a substituted or unsubstituted 6- to 15-membered ring X. n9 is the number of substituents R9, which is selected from 0 to the maximum number of substitutable elements. When n9 is greater than 1, any two R9s are the same or different. Optionally, any two adjacent R9s are connected to form a substituted or unsubstituted 6- to 15-membered ring Y. n 10 Indicates substituent R 10 The number of n 10 Selected from 0 to the largest substitutable number, when n 10 When greater than 1, any two R 10 Same or different; optionally, any two adjacent n 10 The links between them form substituted or unsubstituted 6-15 membered rings Z; n 11 Indicates substituent R 11 The number of n 11 Selected from 0 to the largest substitutable number, when n 11 When greater than 1, any two R 11 Same or different; optionally, any two adjacent R 11 The links between them form substituted or unsubstituted 6-15 membered rings W; R a R b Each R1, each R2, each R3, each R4, each R5, each R6, each R7, each R8, each R9, each R 10 Each R 11 The substituents in L1, L2, L3, L4, L5, L6, Ar1, Ar2, Ar3, and Ar4 may be the same or different, and each is independently selected from deuterium, halogen, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, cycloalkyl with 3 to 10 carbon atoms, aryl with 6 to 20 carbon atoms, and heteroaryl with 3 to 20 carbon atoms.
[0044] In some embodiments, L1, L2, L3, L4, L5, and L6 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 26 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 18 carbon atoms. Ar1, Ar2, Ar3 and Ar4 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups with 6 to 26 carbon atoms, or substituted or unsubstituted heteroaryl groups with 3 to 18 carbon atoms; Rings C, D, E, and F may be the same or different, and each is independently selected from aromatic rings with 6 to 26 carbon atoms or heteroaromatic rings with 3 to 30 carbon atoms; R b Each R8, each R9, each R 10 Each R 11 They may be the same or different, and each is independently selected from hydrogen, deuterium, halogen, cyano, alkyl with 1 to 6 carbon atoms, haloalkyl with 1 to 6 carbon atoms, substituted or unsubstituted aryl with 6 to 18 carbon atoms, and substituted or unsubstituted heteroaryl with 3 to 18 carbon atoms. n8 is the number of substituents R8, and n8 is selected from 0, 1, 2, 3, 4, 5 or 6. When n8 is greater than 1, any two R8s are the same or different. Optionally, any two adjacent R8s are connected to form a substituted or unsubstituted 6-15 membered ring X. n9 is the number of substituents R9, and n9 is selected from 0, 1, 2, 3, 4, 5 or 6. When n9 is greater than 1, any two R9s are the same or different. Optionally, any two adjacent R9s are connected to form a substituted or unsubstituted 6- to 15-membered ring Y. n 10 Indicates substituent R 10 The number of n 10 Choose from 0, 1, 2, 3, 4, 5, or 6, when n 10 When greater than 1, any two R 10 Same or different; optionally, any two adjacent n 10 The links between them form substituted or unsubstituted 6-15 membered rings Z; n 11 Indicates substituent R 11 The number of n 11 Choose from 0, 1, 2, 3, 4, 5, or 6, when n 11 When greater than 1, any two R 11 Same or different; optionally, any two adjacent R 11 The links between them form substituted or unsubstituted 6-15 membered rings W; R b Each R8, each R9, each R 10 Each R 11The substituents in L1, L2, L3, L4, L5, and L6 may be the same or different, and each is independently selected from deuterium, halogen, alkyl with 1 to 5 carbon atoms, haloalkyl with 1 to 5 carbon atoms, cycloalkyl with 3 to 8 carbon atoms, aryl with 6 to 18 carbon atoms, and heteroaryl with 3 to 20 carbon atoms.
[0045] In some embodiments, L1, L2, L3, L4, L5, and L6 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 18 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 12 carbon atoms. Ar1, Ar2, Ar3 and Ar4 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups with 6 to 12 carbon atoms, or substituted or unsubstituted heteroaryl groups with 3 to 12 carbon atoms. Rings C, D, E, and F may be the same or different, and each is independently selected from aromatic rings with 6 to 12 carbon atoms or heteroaromatic rings with 3 to 12 carbon atoms; R b Each R8, each R9, each R 10 Each R 11 They may be the same or different, and each is independently selected from hydrogen, deuterium, halogen, cyano, alkyl with 1 to 5 carbon atoms, haloalkyl with 1 to 5 carbon atoms, substituted or unsubstituted aryl with 6 to 18 carbon atoms, and substituted or unsubstituted heteroaryl with 3 to 20 carbon atoms. R b Each R8, each R9, each R 10 Each R 11 The substituents in L1, L2, L3, L4, L5, and L6 may be the same or different, and each is independently selected from deuterium, halogen, alkyl with 1 to 4 carbon atoms, haloalkyl with 1 to 4 carbon atoms, cycloalkyl with 3 to 8 carbon atoms, aryl with 6 to 12 carbon atoms, and heteroaryl with 3 to 12 carbon atoms.
[0046] In some embodiments, L1, L2, L3, L4, L5, and L6 may be the same or different, and each is independently selected from the group consisting of single-bonded, deuterated, or undeuterated groups: , , , ; "Indicates the connection site with Equation I, " "Indicates the connection site with Ar1, Ar2, Ar3, or Ar4; Ar1, Ar2, Ar3, and Ar4 may be the same or different, and each is independently selected from the group consisting of deuterated or undeuterated groups: , ; Rings C, D, E, and F may be the same or different, and each is independently selected from benzene rings or naphthalene rings; R b Each R8, each R9, each R 10 Each R 11 The same or different, and each independently selected from the group consisting of hydrogen, deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, deuterated or undeuterated groups: , , .
[0047] In some implementations, rings X, Y, Z, and W may be the same or different, and each is independently [defined as such]. “ " indicates that rings X, Y, Z, and W are connected to R8, R9, and R 10 R 11 The fusion site of the substituted benzene ring.
[0048] In some embodiments, at least one of R1, R2, and R3 is selected from the group consisting of deuterated or undeuterated groups: .
[0049] In some embodiments, Formula I of this application is selected from one of the following structures, whether deuterated or undeuterated: .
[0050] In some embodiments, each R1, each R2, each R3, each R4, each R5, each R6 and each R7 may be the same or different, and each is independently selected from hydrogen, deuterium, halogen, cyano, alkyl with 1 to 6 carbon atoms, haloalkyl with 1 to 6 carbon atoms, substituted or unsubstituted bridged cycloalkyl with 4 to 10 carbon atoms, substituted or unsubstituted aryl with 6 to 18 carbon atoms, substituted or unsubstituted heteroaryl with 3 to 18 carbon atoms, or group Q; The substituents in each of R1, R2, R3, R4, R5, R6 and R7 are the same or different, and are each independently selected from halogens, alkyl groups having 1 to 10 carbon atoms, haloalkyl groups having 1 to 10 carbon atoms, cycloalkyl groups having 3 to 10 carbon atoms, aryl groups having 6 to 20 carbon atoms, and heteroaryl groups having 3 to 20 carbon atoms; n1 is the number of substituents R1, and n1 is 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 substituents R2, and n2 is selected from 0, 1, 2, 3 or 4. When n2 is greater than 1, any two R2s are the same or different. n4 is the number of substituents R4, and n4 is selected from 0, 1, 2, 3 or 4. When n4 is greater than 1, any two R4s are the same or different. n5 is the number of substituents R5, and n5 is selected from 0, 1, 2, 3 or 4. When n5 is greater than 1, any two R5s are the same or different. n6 is the number of substituents R6, and n6 is selected from 0, 1, 2, 3 or 4. When n6 is greater than 1, any two R6s are the same or different. n7 is the number of substituents R7, which can be selected from 0, 1, 2, 3 or 4. When n7 is greater than 1, any two R7s can be the same or different.
[0051] In some embodiments, each of R1, R2, R3, R4, R5, R6, and R7 may be the same or different, and each is independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, isopropyl, tert-butyl, trifluoromethyl, phenyl, group Q, or deuterated or undeuterated groups of the following: .
[0052] In some embodiments, the organic compounds of this application are selected from the group consisting of: .
[0053] In a second aspect, this application provides an organic electroluminescent device, which includes a cathode and an anode disposed opposite to each other, and a functional layer disposed between the cathode and the anode, the functional layer containing the organic compound of the first aspect of this application.
[0054] In some embodiments, the functional layer includes an organic light-emitting layer, which includes a sensitizer comprising an organic compound of the first aspect of this application.
[0055] In some implementations, the ΔE of the sensitizer ST The value is 0.01 eV to 0.30 eV, where ΔE ST This is the difference between the lowest excited singlet state energy level and the lowest excited triplet state energy level of the sensitizer. Using the organic compound of the first aspect of this application as the sensitizer results in a smaller ΔE. ST This is beneficial for increasing the reverse intersystem crossing rate (k risc This enables triplet excitons to be efficiently converted into luminescent singlet excitons, thereby improving the luminous efficiency of the device.
[0056] In one specific embodiment, the organic electroluminescent device includes: an anode, a hole transport layer, an organic light-emitting layer, an electron transport layer, and a cathode, which are stacked sequentially.
[0057] Optionally, a hole injection layer may be provided between the anode and the hole transport layer to enhance the ability to inject holes into the hole transport layer.
[0058] Optionally, an electron injection layer may be provided between the cathode and the electron transport layer to enhance the ability to inject electrons into the electron transport layer.
[0059] Optionally, an organic coating layer may also be provided on the cathode.
[0060] In one specific embodiment, the structure of the green organic electroluminescent device is as follows: Figure 1 As shown, the device includes an anode 100, a hole injection layer 310, a first hole transport layer 321, a second hole transport layer 322, an organic light-emitting layer 330, a hole blocking layer 340, an electron transport layer 350, an electron injection layer 360, and a cathode 200, which are stacked sequentially. The hole injection layer 310, the first hole transport layer 321, the second hole transport layer 322, the organic light-emitting layer 330, the hole blocking layer 340, the electron transport layer 350, and the electron injection layer 360 constitute the functional layer 300 of the organic electroluminescent device; the first hole transport layer 321 and the second hole transport layer (light-emitting adjustment layer) 322 constitute the hole transport layer 320.
[0061] Optionally, the anode 100 comprises the following anode materials, preferably those 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. A transparent electrode comprising indium tin oxide (ITO) is preferably used as the anode.
[0062] In some embodiments, the hole transport region 320 includes one or more hole transport materials, which may be selected from carbazole polymers, carbazole-linked triarylamine compounds, or other types of compounds, and will not be listed here.
[0063] In one specific embodiment of this application, the first hole transport layer 321 is composed of compound HT-1 ( The second hole transport layer 322 is composed of compound HT-2 ( ) )composition.
[0064] 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 may be selected from benzidine derivatives, starburst-like aryl amine compounds, phthalocyanine derivatives, or other materials, and this application does not impose any special restrictions on this.
[0065] In one embodiment of this application, the hole injection layer 310 is composed of PD-1 ( ) and compound HT-1 ( )composition.
[0066] Optionally, the organic light-emitting layer 330 may be composed of a single light-emitting material.
[0067] 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. The host material of the organic light-emitting layer 330 may be one compound or a combination of two or more compounds. This application does not impose any limitations on this.
[0068] In one embodiment of this application, the host material of the organic light-emitting layer 330 includes a first host compound P ( ) and the second main compound N ( ).
[0069] In one embodiment of this application, the organic light-emitting layer 330 includes a sensitizer, which is an organic compound of this application.
[0070] In one embodiment of this application, the hole-blocking layer 340 includes compound HB-1 ( ).
[0071] In some embodiments of this application, the electron transport layer 350 can be a single-layer structure or a multi-layer structure, and can include one or more electron transport materials. The electron transport materials can typically include metal complexes and / or nitrogen-containing heterocyclic derivatives. The metal complex material can be selected from, for example, LiQ, Alq3, Bepq2, etc.; the nitrogen-containing heterocyclic derivative can be an aromatic ring with a nitrogen-containing six-membered or five-membered ring skeleton, a fused aromatic ring compound with a nitrogen-containing six-membered or five-membered ring skeleton, etc. Specific examples include, but are not limited to, 1,10-phenanthroline compounds such as ET-15, Bphen, NBphen, DBimiBphen, and BimiBphen, or anthracene compounds, triazine compounds, or pyrimidine compounds containing heteroazo aryl groups. The embodiments of this application do not limit the scope of the invention.
[0072] In one embodiment of this application, the electron transport layer 350 is composed of ET-1 ( ) and LiQ ( )composition.
[0073] In this application, cathode 200 includes 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 is included as the cathode.
[0074] Optional, such as Figure 1 As shown, an electron injection layer 360 is further disposed 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 one embodiment of this application, the electron injection layer 360 includes ytterbium (Yb).
[0075] In some embodiments of this application, an organic coating layer may also be provided on the cathode 200, said organic coating layer being composed of CP-1 ( )composition.
[0076] Thirdly, this application provides an electronic device, which includes the above-mentioned organic electroluminescent device.
[0077] In this application, the electronic device may be, for example, a common device including the aforementioned organic electroluminescent device. The electronic device may be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices, including but not limited to computer screens, mobile phone screens, televisions, electronic paper, emergency lighting, optical modules, etc.
[0078] The following examples illustrate the method for synthesizing the organic compounds of this application, but this application is not limited thereto.
[0079] The present application is further described in detail below through examples. The following examples describe the disclosure of this application in more detail. These examples are merely illustrative, as various modifications and variations within the scope of the disclosure of this application will be apparent to those skilled in the art. Unless otherwise stated, all parts, percentages, and ratios reported in the following examples are based on weight, and all reagents used in the examples are commercially available or synthesized using conventional methods, as are the instruments used in the examples.
[0080] Synthesis Example: In all synthesis examples, the high-resolution mass spectrometry (MS) data were determined using an Orbitrap Exploris 120 mass spectrometer HPLC-M (column model: Zorbax SB-C18, 2.1 × 30 mm, 3.5 μm), for 10 min at a flow rate of 0.4 mL / min. The mobile phase was 100% acetonitrile (containing 0.1% formic acid), and electrospray ionization (ESI) was performed at 210 nm / 254 nm, with UV detection.
[0081] 1H NMR: JEOL 400MHz NMR spectrometer, room temperature, CD2Cl2 as solvent (in ppm), TMS (0ppm) as reference standard.
[0082] 1.1 Synthesis of intermediate IM B-1
[0083] Under nitrogen protection, reactant IMA-1 (50.00 g, 261.16 mmol), 5 iodine grains, and 500 mL of anhydrous tetrahydrofuran were added to a three-necked flask. The mixture was stirred at 0 °C for 15 min until intermediate IMA-1 was completely dissolved. Then, magnesium shavings (6.98 g, 287.28 mmol) were added to the flask, and the reaction was initiated by heating. The system was then heated to 60 °C and refluxed for 3 h. After the reaction was completed, the reaction solution was allowed to cool naturally to room temperature to obtain intermediate IMA-1-Gr.
[0084] At 0 °C, intermediate IM A-1-Gr was slowly added dropwise to 250 mL of anhydrous tetrahydrofuran solution of intermediate CN-1 (25.73 g, 130.60 mmol). The mixture was stirred for 30 min, and then allowed to warm naturally to 25 °C and stirred for 24 h. After the reaction was complete, a saturated aqueous solution of ammonium chloride was slowly added dropwise to quench the reaction, followed by extraction with ethyl acetate. The combined organic phases were dried over anhydrous magnesium sulfate and concentrated to give the crude product. The crude product was purified by recrystallization from a mixed solvent of ethyl acetate and n-hexane to give intermediate IM B-1 (27.38 g, 49% yield).
[0085] 1.2 Synthesis of intermediate IM C-1
[0086] 2-Bromobiphenyl (38.48 g, 165.06 mmol), 4 grains of iodine, and anhydrous tetrahydrofuran (350 mL) were added sequentially to a three-necked flask. The mixture was stirred at 0 °C for 15 min to completely dissolve the 2-bromobiphenyl. Then, magnesium shavings (4.41 g, 181.56 mmol) were added to the flask, and the reaction was initiated by heating. The reaction mixture was then refluxed at 60 °C for 3 h to obtain a freshly prepared Grignard reagent. Next, the freshly prepared Grignard reagent was slowly added dropwise to an anhydrous tetrahydrofuran (350 mL) solution of intermediate IM B-1 (35.00 g, 82.53 mmol) at 0 °C, and the mixture was stirred for 30 min. The mixture was then allowed to rise naturally to 25 °C and the reaction was continued with stirring for 24 h. After the reaction was complete, a saturated ammonium chloride aqueous solution was slowly added dropwise to the flask to quench the reaction. The reaction mixture was extracted with dichloromethane, and the organic phases were combined and concentrated under reduced pressure to remove the solvent, yielding the intermediate. The obtained intermediate was dissolved in glacial acetic acid (200 mL), and concentrated hydrochloric acid (10 mL, 30 wt%) was added to the reaction system. The reaction system was refluxed for 12 h under nitrogen protection. After the reaction was completed, the reaction solution was cooled to room temperature and then slowly poured into 400 mL of deionized water. The solid precipitated, filtered, and washed with deionized water until neutral. The obtained solid was recrystallized from toluene to give intermediate IM C-1 (31.20 g, yield 54%).
[0087] 1.3 Synthesis of intermediate IM D-1
[0088] Under nitrogen protection, intermediate IM C-1 (30.00 g, 43.07 mmol) was dissolved in a round-bottom flask containing tert-butylbenzene (300 mL). The system was cooled to -40 °C, and a 1.5 M solution of tert-butyllithium n-pentane (86 mL, 129.22 mmol) was added dropwise. The resulting mixture was heated to 100 °C and stirred at this temperature for 6 h. The reaction system was then cooled to -40 °C, and boron triiodide (50.59 g, 129.22 mmol) was added dropwise. The reaction solution was then heated to 100 °C and stirred for 4 h. The reaction system was then cooled to room temperature, cooled to 0 °C in an ice bath, and N,N-diisopropylethylamine (50 mL, 288.59 mmol) was added. After the addition was complete, the temperature was raised to room temperature and stirred for 30 min. The reaction solution was then heated to 120 °C and stirred at 120 °C for 4 h. After the reaction system was cooled to room temperature, sodium carbonate aqueous solution was added to the reaction solution to quench the reaction, followed by extraction with ethyl acetate and combining the organic phases. The solvent was removed by vacuum concentration to obtain the crude product. The crude product was separated by column chromatography (mobile phase: n-heptane / dichloromethane) to obtain intermediate IM D-1 (7.20 g, yield 28%).
[0089] 1.4 Synthesis of Compound A3
[0090] Under nitrogen protection, intermediate IM D-1 (6.00 g, 9.98 mmol), reactant IM E-1 (1.84 g, 10.98 mol), tris(dibenzylacetone)dipalladium (0.09 g, 0.10 mmol), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (0.10 g, 0.20 mmol), sodium tert-butoxide (1.44 g, 14.98 mmol), and xylene (60 mL) were added to a round-bottom flask and stirred at 135 °C for 8 h. After the reaction was completed, the reaction system was cooled to room temperature, the reaction solution was washed with water and separated, and the organic phase was dried over anhydrous magnesium sulfate and concentrated to obtain the crude product. The crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane mixed solvent as the eluent. The resulting sample was then purified by recrystallization using a dichloromethane / ethanol mixed solvent to give compound A3 (4.20 g, yield: 57%), mass spectrometry m / z = 732.29 [M+H]. + .
[0091] 1.5 Synthesis of compounds A9 and A16 Following the synthesis of compound A3, the compounds shown in Table 1 below were synthesized. In this synthesis, reactant IM EX replaced IM E-1, resulting in the compounds shown in Table 1 below.
[0092] Table 1
[0093] 2.1 Synthesis of intermediate IM E-4-1
[0094] Under nitrogen protection, the reactants 1-bromo-3-chlorocarbazole (5.00 g, 17.82 mmol), 1-iodo-9H-carbazole (5.22 g, 17.82 mmol), tris(dibenzylacetone)palladium (0.49 g, 0.53 mmol), tri-tert-butylphosphine (0.22 g, 1.07 mmol), and sodium tert-butoxide (5.14 g, 53.47 mmol) were added to toluene (100 mL). The reaction system was heated to 65 °C and reacted with stirring for 12 h. After the reaction was completed, the mixture was cooled to room temperature, diluted with water, and extracted with dichloromethane. The combined organic phases were dried, filtered, and concentrated to obtain the crude product. The crude product was separated by column chromatography (eluent: dichloromethane / petroleum ether system) to obtain intermediate IM E-4-1 (3.83 g, yield: 59%).
[0095] 2.2 Synthesis of intermediate IME-4
[0096] Under nitrogen protection, intermediate IM E-4-1 (3.00 g, 8.22 mmol), pinacol diborate (2.30 g, 9.05 mmol), tris(dibenzylacetone)dipalladium (0.15 g, 0.16 mmol), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (0.16 g, 0.33 mmol), and potassium acetate (1.61 g, 16.45 mmol) were added to a dry container of 1,4-dioxane (50 mL). The reaction mixture was heated to 80 °C and stirred for 8 h. After the reaction was complete, the mixture was cooled to room temperature, diluted with water, and extracted with ethyl acetate. The combined organic phases were dried, filtered, and concentrated to obtain a crude product. The crude product was then purified by recrystallization using a dichloromethane / n-heptane mixed solvent to obtain intermediate IM E-4 (2.73 g, yield: 73%).
[0097] 2.3 Synthesis of Compound A31
[0098] Under nitrogen protection, IM D-1 (2.00 g, 3.33 mmol), IM E-4 (1.67 g, 3.66 mmol), tetratetraphenylphosphine palladium (0.08 g, 0.07 mmol), tetrabutylammonium bromide (0.11 g, 0.33 mmol), and potassium carbonate (0.92 g, 6.66 mmol) were added to a reaction flask. Then, toluene (20 mL), ethanol (10 mL), and water (5 mL) were added as solvents. The mixture was stirred and heated to reflux for 12 h. After the reaction was complete, the mixture was cooled to room temperature and extracted with dichloromethane. The resulting organic phase was washed with water until neutral, dried, filtered, and concentrated to obtain a crude product. The crude product was then purified by recrystallization using a dichloromethane / petroleum ether mixed solvent to obtain compound A31 (2.24 g, yield: 75%), mass spectrometry m / z = 895.33 [M+H]. + .
[0099] 2.4 Synthesis of compounds A34 and A41 Following the synthesis of compound A31, the compounds shown in Table 2 below were synthesized, with intermediate IM EX replacing IM E-4.
[0100] Table 2
[0101] 3.1 Synthesis of intermediate IMA-2
[0102] Under nitrogen protection, reactants IMA-2-1 (6.56 g, 19.68 mmol), IMA-7 (5.00 g, 17.89 mmol), tris(dibenzylacetone)dipalladium (0.16 g, 0.18 mmol), 4,5-bis(diphenylphosphine-9,9-dimethyloxanthracene) (0.21 g, 0.36 mmol), sodium tert-butoxide (2.58 g, 26.84 mmol), and toluene (120 mL) were added to a round-bottom flask and reacted at 80 °C with stirring for 8 h. After the reaction was complete, the mixture was cooled to room temperature, washed with water, and separated. The organic phase was dried over anhydrous magnesium sulfate, and the solvent was removed by concentration under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (using a toluene / n-heptane mixed solvent as eluent), and then the purified sample was recrystallized using a toluene / n-heptane mixed solvent to obtain compound IMA-2 (5.30 g, yield: 61%).
[0103] 3.2 Synthesis of intermediates IMA-3 to IMA-6 Following the synthesis of intermediate IM A-2, the intermediates shown in Table 3 were synthesized. In this synthesis, reactant IM AXN replaced IM A-2-1, and reactant IM EX replaced IM E-7, resulting in the intermediates shown in Table 3.
[0104] Table 3
[0105] 3.3 Synthesis of intermediate IMA-7
[0106] Under nitrogen protection, IMA-3-1 (5.00 g, 15.76 mmol), IME-4 (7.91 g, 17.33 mmol), tetratetraphenylphosphine palladium (0.36 g, 0.32 mmol), tetrabutylammonium bromide (0.51 g, 1.58 mmol), and potassium carbonate (4.35 g, 31.51 mmol) were added to the reaction flask. Then, toluene (80 mL), ethanol (40 mL), and water (20 mL) were added. The mixture was stirred and heated to 60 °C for 12 h. After the reaction was completed, the mixture was cooled to room temperature and extracted with dichloromethane. The organic phase was separated and washed with water until neutral. After drying, filtration, and concentration, the crude product was obtained. The crude product was purified by silica gel column chromatography (using a dichloromethane / n-heptane mixed solvent as the eluent). The purified sample was then recrystallized and purified using a toluene / ethanol mixed solvent to obtain intermediate IMA-7 (3.85 g, yield: 47%).
[0107] 3.4 Synthesis of intermediates IMA-8 to IMA-15 Following the synthesis of intermediate IM A-7, the intermediates shown in Table 4 were synthesized. In this synthesis, reactant IM AXN replaced IM A-3-1, and reactant IM EX replaced IM E-4, resulting in the intermediates shown in Table 4.
[0108] Table 4
[0109] 3.5 Synthesis of intermediates IM A-2-Gr to IM A-15-Gr Following the synthesis of intermediate IM A-1-Gr, the intermediates shown in Table 5 were synthesized. In this case, intermediate IM AX was used instead of IM A-1, resulting in the intermediates shown in Table 5.
[0110] Table 5
[0111] 3.6 Synthesis of intermediate IM B-2-1
[0112] At 0 °C, intermediate IM A-1-Gr was slowly added dropwise to an anhydrous tetrahydrofuran solution (400 mL) of intermediate CN-2 (42.5 g, 261.42 mmol) to obtain a mixture. The mixture was stirred at 0 °C for 30 min, and then naturally heated to 25 °C and stirred for 24 h. After the reaction was completed, a saturated ammonium chloride aqueous solution was slowly added dropwise to quench the reaction, followed by extraction with ethyl acetate. The combined organic phases were dried over anhydrous magnesium sulfate, and the crude product was concentrated and purified by silica gel column chromatography (using a dichloromethane / n-heptane mixed solvent as eluent), followed by recrystallization (using a tetrahydrofuran / ethanol mixed solvent) to obtain intermediate IM B-2-1 (7.21 g, yield 10%).
[0113] 3.7 Synthesis of other intermediates Following the synthesis of intermediate IM B-2-1, the intermediates shown in Table 6 were synthesized. Intermediate IM AX-Gr replaced IM A-1-Gr, and intermediate CN-X replaced CN-2, resulting in the intermediates shown in Table 6.
[0114] Table 6
[0115] 4.1 Synthesis of intermediate IM B-2
[0116] Step 1: IM B-2-1 (72.00 g, 260.76 mmol) and ethylene glycol (29.08 mL, 521.52 mmol) were added to a three-necked flask containing toluene (700 mL). Then, p-toluenesulfonic acid (4.49 g, 26.08 mmol) was slowly added dropwise to the reaction solution. After the addition was complete, the reaction system was naturally heated to 140 °C and stirred at this temperature for 3 h. After the reaction was completed, the reaction solution was cooled to room temperature, and the solvent was removed by vacuum concentration. The residue was dissolved and concentrated with ethyl acetate, and then washed successively with water and saturated sodium bicarbonate solution. The resulting organic phase was dried over anhydrous magnesium sulfate and concentrated. The crude product was purified by silica gel column chromatography (using a dichloromethane / n-heptane mixed solvent as eluent) to obtain intermediate IM B-2-2 (79.32 g, yield 95%).
[0117] Step 2: At 0°C, intermediate IM A-2-Gr was slowly added dropwise to an anhydrous tetrahydrofuran solution (600 mL) of IM B-2-2 (83.00 g, 259.24 mmol) to obtain a mixture. The mixture was stirred at 0°C for 30 min, and then naturally heated to 25°C and stirred for 24 h. After the reaction was completed, a saturated ammonium chloride aqueous solution was slowly added dropwise to the reaction flask to quench the reaction. The quenched reaction solution was extracted with ethyl acetate, and the extracted organic phases were combined. The organic phases were dried with anhydrous magnesium sulfate, and the crude product obtained by concentration was purified by silica gel column chromatography (using a dichloromethane / n-heptane mixed solvent as eluent). The obtained sample was then purified by recrystallization (tetrahydrofuran / ethanol mixed solvent) to obtain intermediate IM B-2-3 (85.65 g, yield 45%).
[0118] Step 3: Dissolve IM B-2-3 (85.65 g, 117.79 mmol) in tetrahydrofuran solution (800 mL), then add 3 mol / L hydrochloric acid solution (800 mL), and stir the reaction at room temperature for 1 h. After the reaction is complete, adjust the pH of the reaction solution to 7-8 with saturated sodium bicarbonate solution until no bubbles are generated, then extract with ethyl acetate. Combine the organic phases, dry with anhydrous magnesium sulfate and filter. Concentrate the filtrate under reduced pressure and purify the crude product using silica gel column chromatography (with dichloromethane / n-heptane mixed solvent as eluent) to obtain intermediate IM B-2 (73.07 g, yield 93%).
[0119] 4.2 Synthesis of other intermediates Referring to the synthesis of intermediate IM B-2, the intermediates shown in Table 7 below were synthesized. In step 1, intermediate IM BXN replaced IM B-2-1, and in step 2, intermediate IM AX-Gr replaced IM A-2-Gr, resulting in the intermediates shown in Table 7 below.
[0120] Table 7
[0121] Note: In Table 7, the yield... a This indicates the yield of the corresponding step in the preparation process of intermediate IMB-X, which corresponds to step 1 in the preparation process of intermediate IMB-2. b This indicates the yield of the corresponding step in the preparation process of intermediate IMBX, which corresponds to step 2 in the preparation process of intermediate IMB-2. cThe yield represents the yield of the corresponding step in the preparation process of intermediate IMBX, which corresponds to step 3 in the preparation process of intermediate IMB-2. The total yield represents the combined yield of steps 1, 2, and 3 in the preparation process of intermediate IMBX.
[0122] 4.3 Synthesis of intermediate IM CX Following the synthesis of intermediate IM C-1, synthesize the intermediates shown in Table 8 below. Intermediate IM BX replaces IM B-1, resulting in the intermediates shown in Table 8 below.
[0123] Table 8
[0124] 5.1 Synthesis of Compound A11
[0125] Under nitrogen protection, intermediate IM C-2 (3.00 g, 3.19 mmol) was dissolved in a round-bottom flask containing tert-butylbenzene (30 mL). When the system was cooled to -40 °C, a 1.5 M solution of tert-butyllithium n-pentane (6.40 mL, 9.58 mmol) was added dropwise to obtain a mixture. The mixture was heated to 100 °C and stirred for 6 h. The reaction system was then cooled to -40 °C, and boron tribromide (0.92 mL, 9.58 mmol) was added dropwise. After the addition was complete, the reaction system was reheated to 100 °C and stirred for 4 h. The reaction system was then cooled to room temperature, cooled to 0 °C in an ice bath, and N,N-diisopropylethylamine (3.73 mL, 21.40 mmol) was added. After the addition was complete, the temperature was raised to room temperature and stirred for 30 min, then further raised to 120 °C and stirred for 4 h. After the reaction system cooled to room temperature, the reaction was quenched with water, followed by extraction with dichloromethane and combining the organic phases. The solvent was removed by concentration under reduced pressure to obtain a crude product. The crude product was then separated by column chromatography (mobile phase: n-heptane / dichloromethane) to obtain compound A11 (0.82 g, yield 30%), mass spectrometry m / z = 844.41 [M+H]. + .
[0126] 5.2 Synthesis of other compounds Following the synthesis of compound A11, the compounds shown in Table 9 below were synthesized. In this synthesis, intermediate IM CX was used instead of IM C-2, resulting in the compounds shown in Table 9 below.
[0127] Table 9
[0128] 6.1 Synthesis of Compound B43 (1) Following the synthesis of intermediate IM D-1, synthesize the intermediates shown in Table 10 below. In this case, intermediate IM CX replaces IM C-1, and synthesize the intermediates shown in Table 10 below.
[0129] Table 10
[0130] (2) Following the synthesis of compound A3, synthesize the compounds shown in Table 11 below. In this case, intermediate IM DX replaces IMD-1, and intermediate IM EX replaces IM E-1, to synthesize the compounds shown in Table 11 below.
[0131] Table 11
[0132] 6.2 Synthesis of other compounds Following the synthesis of compound A31, the compounds shown in Table 12 below were synthesized. Intermediate IM DX replaced IM D-1, and intermediate IM EX replaced IM E-4, resulting in the compounds shown in Table 12 below.
[0133] Table 12
[0134] 7.1 Synthesis of intermediates IM B-11 to IM B-13 Following the synthesis of intermediate IM B-1, the intermediates shown in Table 13 below were synthesized. Intermediate IM AX-Gr replaced IM A-1-Gr, and intermediate CN-X replaced CN-1, resulting in the intermediates shown in Table 13 below.
[0135] Table 13
[0136] 7.2 Synthesis of intermediates IM C-11 to IM C-13 Following the synthesis of intermediate IM C-1, the intermediates shown in Table 14 below were synthesized. Intermediate IM BX was used instead of IMB-1, and the intermediates were synthesized as shown in Table 14 below.
[0137] Table 14
[0138] 7.3 Synthesis of intermediates IM D-5 and IM D-6 Following the synthesis of intermediate IM D-1, the intermediates shown in Table 15 below were synthesized. Intermediate IM CX was used instead of IMC-1, resulting in the intermediates shown in Table 15 below.
[0139] Table 15
[0140] 7.4 Synthesis of Compound B85 Following the synthesis of compound A11, the compounds shown in Table 16 below were synthesized, wherein intermediate IM CX was used instead of IM C-2, resulting in the compounds shown in Table 16 below.
[0141] Table 16
[0142] 7.5 Synthesis of Compound C1 Following the synthesis of compound A3, the compounds shown in Table 17 below were synthesized. Intermediate IM DX replaced IM D-1, and intermediate IM EX replaced IM E-1, resulting in the compounds shown in Table 17 below.
[0143] Table 17
[0144] 7.6 Synthesis of Compound C4 Following the synthesis of compound A31, the compounds shown in Table 18 below were synthesized. Intermediate IM DX replaced IM D-1, and intermediate IM EX replaced IM E-4, resulting in the compounds shown in Table 18 below.
[0145] Table 18
[0146] 8.1 Synthesis of intermediate IM F-1
[0147] At room temperature, 2,6-dibromo-3-fluorochlorobenzene (17.78 g, 61.65 mmol), 1-phenylcarbazole (10.00 g, 41.10 mmol), cesium carbonate (26.78 g, 82.20 mmol), and N,N-dimethylformamide (200 mL) were sequentially added to a three-necked flask. The reaction mixture was heated to reflux and reacted for 12 h. After the reaction was completed, the reaction solution was cooled to room temperature, diluted with saturated brine, extracted with dichloromethane, and the organic phases were combined and dried with anhydrous magnesium sulfate. After filtration, the filtrate was distilled under reduced pressure to remove the solvent. The residue was separated by column chromatography using a dichloromethane / n-heptane system as the eluent to obtain intermediate IM F-1 (19.20 g, 91% yield).
[0148] 8.2 Preparation of intermediate IM G-1
[0149] Under nitrogen protection, intermediate IM F-1 (10.00 g, 19.54 mmol) was dissolved in a flask containing anhydrous diethyl ether (100 mL). The reaction solution was cooled to -78 °C, and a 2.5 M n-butyllithium n-hexane solution (8.60 mL, 21.50 mmol) was slowly added dropwise. After the addition was complete, the mixture was stirred at -78 °C for 2 h. Then, benzocyanine (4.39 mL, 43.00 mmol) was slowly added dropwise. After the addition was complete, the mixture was stirred at -78 °C for 1 h. After the reaction was completed, the reaction solution was allowed to rise naturally to room temperature. A 10% hydrochloric acid solution was added dropwise to quench the reaction, and then a saturated sodium carbonate aqueous solution was added to adjust the reaction solution to neutral. The solution was then extracted with ethyl acetate. The organic phase was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to remove the solvent. The residue was separated by column chromatography using a dichloromethane / petroleum ether system as the eluent to obtain intermediate IMG-1 (6.59 g, yield 60%).
[0150] 8.3 Synthesis of intermediate IM H-1 Following the synthesis of intermediate IM C-1, the intermediates shown in Table 19 below were synthesized. Intermediate IM GX was used instead of IMB-1, and the intermediates were synthesized as shown in Table 19 below.
[0151] Table 19
[0152] 8.4 Synthesis of Compound A50 Following the synthesis of compound A11, the compounds shown in Table 20 below were synthesized. In this synthesis, intermediate IM HX was used instead of IM C-2, resulting in the compounds shown in Table 20 below.
[0153] Table 20
[0154] NMR data for some compounds: Table 21
[0155] Fabrication and performance evaluation of organic electroluminescent devices: Example 1: Green Organic Electroluminescent Device The anode pretreatment is first performed through the following process: A substrate is provided, which sequentially comprises a first ITO layer, an Ag layer, and a second ITO layer, wherein the thickness of the first ITO layer is 100 Å, the thickness of the Ag layer is 1000 Å, and the thickness of the second ITO layer is 100 Å. The substrate is then surface-treated using ultraviolet ozone and O2:N2 plasma to increase the work function of the anode. The substrate surface is then cleaned with an organic solvent (ethanol or isopropanol) to remove impurities and oil.
[0156] On the cleaned substrate (anode), PD-1:HT-1 were co-deposited at a deposition rate ratio of 2%:98% to form a hole injection layer with a thickness of 100 Å.
[0157] Compound HT-1 was vacuum-deposited onto the hole injection layer to form a first hole transport layer with a thickness of 1045 Å.
[0158] Compound HT-2 was vacuum-deposited onto the first hole transport layer to form a second hole transport layer with a thickness of 405 Å.
[0159] On the second hole transport layer, an organic light-emitting layer was prepared by co-evaporation using compound P as the first host, compound N as the second host, and compound A3 as the sensitizer. Specifically, compound P, compound N, and compound A3 were co-deposited at a deposition rate ratio of 60%:40%:1% to form an organic light-emitting layer with a thickness of 350 Å.
[0160] On the organic light-emitting layer, compound HB-1 is vacuum-deposited to form a hole-blocking layer with a thickness of 50 Å.
[0161] On the hole blocking layer, compounds ET-1 and LiQ were co-deposited at a 1:1 evaporation rate ratio to form an electron transport layer with a thickness of 300 Å.
[0162] Yb was deposited on the electron transport layer to form an electron injection layer with a thickness of 10 Å. Then, magnesium (Mg) and silver (Ag) were co-deposited at a deposition rate ratio of 1:9 and vacuum-deposited on the electron injection layer to form a cathode with a thickness of 130 Å.
[0163] Furthermore, compound CP-1 is vacuum-deposited onto the aforementioned cathode to form an organic coating layer with a thickness of 660 Å, thereby completing the fabrication of the green organic electroluminescent device.
[0164] Examples 2-20: The methods for preparing organic electroluminescent devices in Examples 2-20 are the same as those in Example 1, except that when preparing the organic light-emitting layer, the compounds listed in Table 22 below are used to replace compound A3 in Example 1.
[0165] Comparative Examples 1-5 Except that when forming the organic light-emitting layer, compound A3 was replaced with compounds A, B, C, D, and E from Table 22 below, the organic electroluminescent device was prepared using the same method as in Example 1.
[0166] The main materials used in the above embodiments and comparative examples are shown below: .
[0167] The singlet-triplet band gap (ΔE) was measured for the compounds in Table 22. ST The phosphorescence and fluorescence at 77K were measured using a HITACHI F-7000 spectrometer, and the results are shown in Table 22.
[0168] Table 22
[0169] As can be seen from Table 22, the compounds provided in this application, by linking azirbenzene derivatives, aromatic amine / aromatic amine derivatives, carbazole / carbazole derivatives, or oxazine derivatives to the benzene ring or azirbenzene ring directly bonded to the boron atom in Formula I, have a molecular structure design that yields compounds with ΔE. ST The voltage ranges from 0.01 to 0.30 eV, down to as low as 0.01 eV, exhibiting a small ΔE. ST This is beneficial for increasing the reverse intersystem crossing rate (k risc This enables triplet excitons to be efficiently converted into luminescent singlet excitons, thereby improving the luminous efficiency of the device.
[0170] The performance of the green photosensitized devices prepared in Examples 1-20 and Comparative Examples 1-5 was tested. Specifically, the voltage, efficiency, J30 lifetime characteristics and CIE(x, y) of the devices were tested under J15. The test results are shown in Table 23.
[0171] Table 23
[0172] Referring to Table 23 above, in Examples 1-20, the compounds of this application were used as sensitizers. Compared with Comparative Examples 1-5, the luminous efficiency of the organic electroluminescent devices was improved by at least 4.8%, and the device lifetime was improved by at least 21.1%. It is evident that using the organic compounds of this application in the organic light-emitting layer of organic electroluminescent devices can effectively improve the luminous efficiency and lifetime of the organic electroluminescent devices. 95 life.
[0173] The preferred embodiments of this application have been described in detail above. 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.
[0174] It should also be noted that the various specific technical features described in the above embodiments can be combined in any suitable manner without contradiction. To avoid unnecessary repetition, this application will not describe the various possible combinations separately.
[0175] Furthermore, various different implementations of this application can be combined in any way, as long as they do not violate the spirit of this application, they should also be regarded as the content disclosed in this application.
Claims
1. An organic compound, characterized in that, The organic compound has a structure selected from that shown in Formula I: Among them, X1 and X2 may be the same or different, and each is independently selected from C(R). a ) or N; R a R1, R2, R3, R4, R5, R6, and R7 may be the same or different, and each is independently selected from hydrogen, deuterium, halogen, cyano, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, substituted or unsubstituted bridged cycloalkyl with 4 to 10 carbon atoms, substituted or unsubstituted aryl with 6 to 18 carbon atoms, substituted or unsubstituted heteroaryl with 3 to 18 carbon atoms, or group Q, and at least one of R1, R2, and R3 is selected from group Q; wherein group Q has the structure shown in formula I-2, formula I-3, formula I-4, or formula I-5. ; In formulas I-2, I-3, I-4, or I-5, " " indicates the connection point with Equation I; L3, L4, L5, and L6 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted arylene groups with 6 to 18 carbon atoms, and substituted or unsubstituted heteroarylene groups with 3 to 18 carbon atoms. Ar3 and Ar4 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups with 6 to 18 carbon atoms; Rings C, D, E, and F may be the same or different, and each is independently selected from an aromatic ring having 6 to 18 carbon atoms; optionally, when R1 and / or R2 are selected from formula I-5, formula I-5 is fused with the ring of formula I; Each R8, each R9, each R 10 Each R 11 They may be the same or different, and each is independently selected from hydrogen, deuterium, halogen, cyano, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, substituted or unsubstituted aryl with 6 to 18 carbon atoms, and substituted or unsubstituted heteroaryl with 3 to 18 carbon atoms. n1 is the number of substituents R1, and n1 is 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 substituents R2, and n2 is selected from 0, 1, 2, 3 or 4. When n2 is greater than 1, any two R2s are the same or different. n4 is the number of substituents R4, and n4 is selected from 0, 1, 2, 3 or 4. When n4 is greater than 1, any two R4s are the same or different. n5 is the number of substituents R5, and n5 is selected from 0, 1, 2, 3 or 4. When n5 is greater than 1, any two R5s are the same or different. n6 is the number of substituents R6, and n6 is selected from 0, 1, 2, 3 or 4. When n6 is greater than 1, any two R6s are the same or different. n7 is the number of substituents R7, which can be selected from 0, 1, 2, 3 or 4. When n7 is greater than 1, any two R7s can be the same or different. n8 is the number of substituents R8, which is selected from 0 to the maximum number of substitutable elements. When n8 is greater than 1, any two R8s are the same or different. Optionally, any two adjacent R8s are connected to form a substituted or unsubstituted ring X. n9 is the number of substituents R9, which is selected from 0 to the maximum number of substitutable elements. When n9 is greater than 1, any two R9s are the same or different. Optionally, any two adjacent R9s are connected to form a substituted or unsubstituted ring Y. Ring X and ring Y are " "" indicates the fusion sites of ring X, ring Y, and the benzene rings substituted by R8 and R9; n 10 Indicates substituent R 10 The number of n 10 Selected from 0 to the largest substitutable number, when n 10 When greater than 1, any two R 10 Same or different; n 11 Indicates substituent R 11 The number of n 11 Selected from 0 to the largest substitutable number, when n 11 When greater than 1, any two R 11 Same or different; R a Each R1, each R2, R3, each R4, each R5, each R6, each R7, each R8, each R9, each R 10 Each R 11 The substituents in L3, L4, L5, L6, Ar3, and Ar4 may be the same or different, and each is independently selected from deuterium, halogen, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, cycloalkyl with 3 to 10 carbon atoms, aryl with 6 to 12 carbon atoms, and heteroaryl with 3 to 12 carbon atoms.
2. The organic compound according to claim 1, wherein, L3, L4, L5, and L6 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 18 carbon atoms, or substituted or unsubstituted heteroaryl groups with 3 to 12 carbon atoms. Ar3 and Ar4 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups with 6 to 12 carbon atoms, or substituted or unsubstituted heteroaryl groups with 3 to 12 carbon atoms; Rings C, D, E, and F may be the same or different, and each is independently selected from aromatic rings having 6 to 12 carbon atoms; Each R8, each R9, each R 10 Each R 11 They may be the same or different, and each is independently selected from hydrogen, deuterium, halogen, cyano, alkyl with 1 to 5 carbon atoms, haloalkyl with 1 to 5 carbon atoms, substituted or unsubstituted aryl with 6 to 12 carbon atoms, and substituted or unsubstituted heteroaryl with 3 to 18 carbon atoms. Each R8, each R9, each R 10 Each R 11 The substituents in L3, L4, L5, and L6 may be the same or different, and each is independently selected from deuterium, halogen, alkyl with 1 to 4 carbon atoms, haloalkyl with 1 to 4 carbon atoms, cycloalkyl with 3 to 8 carbon atoms, aryl with 6 to 12 carbon atoms, and heteroaryl with 3 to 12 carbon atoms.
3. The organic compound according to claim 1, wherein, L5 and L6 are each single bonds, and L3 and L4 may be the same or different, and each is independently selected from the group consisting of single bonds, deuterated or undeuterated groups: , , , ;" "Indicates the connection site with Equation I," "Indicates the connection site with Ar3 or Ar4; Ar3 and Ar4 may be the same or different, and each is independently selected from the group consisting of deuterated or undeuterated groups: , ; Rings C, D, E, and F may be the same or different, and each is independently selected from benzene rings or naphthalene rings; Each R8, each R9, each R 10 Each R 11 The same or different, and each independently selected from the group consisting of hydrogen, deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, deuterated or undeuterated groups: , , .
4. The organic compound according to claim 1, wherein, Formula I is selected from one of the following structures, whether deuterated or undeuterated: 。 5. The organic compound according to claim 1, wherein, Each of R1, R2, R3, R4, R5, R6 and R7 may be the same or different, and each is independently selected from hydrogen, deuterium, halogen, cyano, alkyl with 1 to 6 carbon atoms, haloalkyl with 1 to 6 carbon atoms, or group Q; The substituents in each of R1, R2, R3, R4, R5, R6 and R7 are defined as in claim 1; The definitions of n1, n2, n4, n5, n6 and n7 are the same as in claim 1.
6. The organic compound according to claim 1, wherein, Each of R1, R2, R3, R4, R5, R6, and R7 may be the same or different, and each is independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, isopropyl, tert-butyl, trifluoromethyl, phenyl, group Q, or deuterated or undeuterated groups of the following: 。 7. The organic compound according to claim 1, wherein, The organic compound is selected from the group consisting of the following compounds: 。 8. An organic compound, characterized in that, The organic compound is selected from the group consisting of the following compounds: .
9. An organic electroluminescent device, comprising a cathode and an anode disposed opposite to each other, and a functional layer disposed between the cathode and the anode, characterized in that, The functional layer includes the organic compound described in any one of claims 1 to 8.
10. The device according to claim 9, wherein, The functional layer includes an organic light-emitting layer, the organic light-emitting layer includes a sensitizer, and the sensitizer includes the organic compound.
11. The device according to claim 10, wherein, The ΔE of the sensitizer ST The value is 0.01 eV to 0.30 eV, where ΔE ST It is the difference between the lowest excited singlet state energy level and the lowest excited triplet state energy level of the sensitizer.
12. An electronic device, characterized in that, The electronic device includes the organic electroluminescent device according to any one of claims 9 to 11.
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