Fused ring compound, organic electroluminescent device and electronic device

Abstract

The application relates to the technical field of organic electroluminescent materials, and provides a fused ring compound, an organic electroluminescent device containing the same and an electronic device. The compound provided by the application takes phenanthroindole connecting a benzene ring as a core structure of the compound, and when the compound provided by the application is used as a main body material of a light-emitting layer, the carrier balance in the light-emitting layer can be improved, the carrier recombination area can be widened, the excitation generation and utilization efficiency can be improved, and the light-emitting efficiency and the service life of the device can be improved.

Description

Technical Field

[0001] This application relates to the field of organic electroluminescent materials technology, and more particularly to fused ring compounds and organic electroluminescent devices and electronic devices containing them. 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 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 a fused ring compound and an organic electroluminescent device and electronic device containing the same, wherein the fused ring compound used in the organic electroluminescent device can improve the performance of the device.

[0005] According to a first aspect of this application, a fused-ring compound is provided, the fused-ring compound having a structure shown in Formula 1.

[0006]

[0007] Group A is selected from the groups shown in a-1, a-2, or a-3:

[0008]

[0009] L, L1, L2, L3, L4 and L5 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.

[0010] Ar3 is selected from the group shown in a-4 or a-5:

[0011]

[0012] Rings E, F, P, and Q are each independently selected from 6–14 aryl rings;

[0013] Het is a nitrogen-containing heteroaryl group with 3 to 20 carbon atoms, and Het contains at least 2 nitrogen atoms;

[0014] Ar1 and Ar2 may be the same or different, and each is independently selected from hydrogen, substituted or unsubstituted aryl groups with 6 to 40 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 40 carbon atoms.

[0015] Ar4, Ar5, and Ar6 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] Each of R1, R2, R3, R4, R5, R6, and R7 may be the same or different, and each is independently selected from deuterium, cyano, halogen group, alkyl group with 1 to 10 carbon atoms, haloalkyl group with 1 to 10 carbon atoms, deuterated alkyl group with 1 to 10 carbon atoms, trialkylsilyl group with 3 to 12 carbon atoms, triphenylsilyl group, aryl group with 6 to 20 carbon atoms, deuterated aryl group with 6 to 20 carbon atoms, haloaryl group with 6 to 20 carbon atoms, heteroaryl group with 3 to 20 carbon atoms, and cycloalkyl group with 3 to 10 carbon atoms;

[0017] n1, n2, and n3 are each independently selected from 0, 1, 2, 3, or 4;

[0018] n4 is selected from 0, 1, 2, or 3;

[0019] n5, n6 and n7 are each independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8;

[0020] The substituents in Ar1, Ar2, Ar4, Ar5, Ar6, L, L1, L2, L3, L4, and L5 may be the same or different, and each is independently selected from deuterium, cyano, halogen groups, alkyl groups with 1 to 10 carbon atoms, haloalkyl groups with 1 to 10 carbon atoms, deuterated alkyl groups with 1 to 10 carbon atoms, trialkylsilyl groups with 3 to 12 carbon atoms, triphenylsilyl groups, aryl groups with 6 to 20 carbon atoms, deuterated aryl groups with 6 to 20 carbon atoms, haloaryl groups with 6 to 20 carbon atoms, heteroaryl groups with 3 to 20 carbon atoms, and cycloalkyl groups with 3 to 10 carbon atoms; optionally, any two adjacent substituents may form a saturated or unsaturated 3 to 15-membered ring.

[0021] 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 fused ring compound.

[0022] According to a third aspect of this application, an electronic device is provided, including the organic electroluminescent device described in the second aspect.

[0023] The compounds in this application comprise a macrocyclic fused-ring core structure formed by phenanthreneindole and a benzene ring. This core is linked to a triarylamine, a carbazole group, or a nitrogen-containing electron-deficient heteroaryl group. Specifically, the benzene ring attached to the nitrogen atom in the core is covalently connected to the carbon atom at position 1 of the phenanthrene ring. This specific connection method forms a fused-ring macrocyclic structure with a large conjugated system, thereby endowing the phenanthreneindole group with superior hole transport capabilities. When the compounds of this application are used as hole transport materials in hybrid host materials or as a single host material, they can improve carrier balance in the luminescent layer, broaden the carrier recombination region, improve exciton generation and utilization efficiency, and enhance device luminous efficiency and lifetime. Attached Figure Description

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

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

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

[0027] Figure Labels

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

[0029] 321. First hole transport layer; 322. Second hole transport layer; 330. Organic light-emitting layer; 340. Electron transport layer

[0030] 350, Electron injection layer; 400, Electronic device Detailed Implementation

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

[0032] In a first aspect, this application provides a fused-ring compound having a structure as shown in Formula 1.

[0033]

[0034] Group A is selected from the groups shown in a-1, a-2, or a-3:

[0035]

[0036] L, L1, L2, L3, L4 and L5 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.

[0037] Ar3 is selected from the group shown in a-4 or a-5:

[0038]

[0039] Rings E, F, P, and Q are each independently selected from 6–14 aryl rings;

[0040] Het is a nitrogen-containing heteroaryl group with 3 to 20 carbon atoms, and Het contains at least 2 nitrogen atoms;

[0041] Ar1 and Ar2 may be the same or different, and each is independently selected from hydrogen, substituted or unsubstituted aryl groups with 6 to 40 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 40 carbon atoms.

[0042] Ar4, Ar5, and Ar6 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.

[0043] Each of R1, R2, R3, R4, R5, R6, and R7 may be the same or different, and each is independently selected from deuterium, cyano, halogen group, alkyl group with 1 to 10 carbon atoms, haloalkyl group with 1 to 10 carbon atoms, deuterated alkyl group with 1 to 10 carbon atoms, trialkylsilyl group with 3 to 12 carbon atoms, triphenylsilyl group, aryl group with 6 to 20 carbon atoms, deuterated aryl group with 6 to 20 carbon atoms, haloaryl group with 6 to 20 carbon atoms, heteroaryl group with 3 to 20 carbon atoms, and cycloalkyl group with 3 to 10 carbon atoms;

[0044] n1, n2, and n3 are each independently selected from 0, 1, 2, 3, or 4;

[0045] n4 is selected from 0, 1, 2, or 3;

[0046] n5, n6 and n7 are each independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8;

[0047] The substituents in Ar1, Ar2, Ar4, Ar5, Ar6, L, L1, L2, L3, L4, and L5 may be the same or different, and each is independently selected from deuterium, cyano, halogen groups, alkyl groups with 1 to 10 carbon atoms, haloalkyl groups with 1 to 10 carbon atoms, deuterated alkyl groups with 1 to 10 carbon atoms, trialkylsilyl groups with 3 to 12 carbon atoms, triphenylsilyl groups, aryl groups with 6 to 20 carbon atoms, deuterated aryl groups with 6 to 20 carbon atoms, haloaryl groups with 6 to 20 carbon atoms, heteroaryl groups with 3 to 20 carbon atoms, and cycloalkyl groups with 3 to 10 carbon atoms; optionally, any two adjacent substituents may form a saturated or unsaturated 3 to 15-membered ring.

[0048] The compounds in this application comprise a macrocyclic fused-ring core structure formed by phenanthreneindole and a benzene ring. This core is connected to a triarylamine, a carbazole group, or a nitrogen-containing electron-deficient heteroaryl group. Specifically, the benzene ring attached to the nitrogen atom in the core is covalently linked to the carbon atom at position 1 of the phenanthrene ring. This specific connection method forms a fused-ring macrocyclic structure with a large conjugated system, thereby endowing the phenanthreneindole group with superior hole transport capabilities. When the core is connected to a triarylamine or carbazole group, the hole transport capability of the compound can be further improved, making the compound more suitable as a hole-transporting host material in mixed host materials. When the core is connected to a nitrogen-containing electron-deficient heteroaryl group, it is more suitable as a bipolar host material with excellent electron and hole transport capabilities.

[0049] In this application, the terms "optionally" and "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 among Ar1, Ar2, Ar4, Ar5, Ar6, L, L1, L2, L3, L4, and L5 form a ring" means that any two adjacent substituents among Ar1, Ar2, Ar4, Ar5, Ar6, L, L1, L2, L3, L4, and L5 are connected to each other to form a ring, or that any two adjacent substituents among Ar1, Ar2, Ar4, Ar5, Ar6, L, L1, L2, L3, L4, and L5 can also exist independently. "Any two adjacent" can include two substituents on the same atom, or two adjacent atoms each having one substituent; wherein, when two substituents are on the same atom, the two substituents can form a saturated or unsaturated spirocyclic ring with the atom they are connected to; when two adjacent atoms each have one substituent, the two substituents can fused together to form a ring.

[0050] In this application, the descriptive phrases "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.

[0051] 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.

[0052] In this application, "multiple" means two or more, such as two, three, four, five, six, etc.

[0053] The hydrogen atoms in the compound structure of this application include various isotopes of hydrogen, such as hydrogen (H), deuterium (D), or tritium (T).

[0054] 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.

[0055] 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.

[0056] 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.

[0057] In this application, terphenyl includes

[0058] 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.

[0059] 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, 30, 31, 33, 34, 35, 36, 38, or 40 carbon atoms. In some embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group with 6 to 40 carbon atoms; in other embodiments, it is a substituted or unsubstituted aryl group with 6 to 30 carbon atoms; in still other embodiments, it is a substituted or unsubstituted aryl group with 6 to 25 carbon atoms; and in yet another embodiment, it is a substituted or unsubstituted aryl group with 6 to 15 carbon atoms.

[0060] 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: etc., but not limited to this.

[0061] In this application, the aryl groups used as substituents for Ar1, Ar2, Ar4, Ar5, Ar6, L, L1, L2, L3, L4 and L5 are, for example, but not limited to, phenyl, naphthyl, phenanthryl, biphenyl, fluorenyl, dimethylfluorenyl and so on.

[0062] In this application, a 6- to 14-membered aromatic ring refers to an aromatic ring having 6 to 14 ring atoms, such as, but not limited to, a benzene ring, a naphthalene ring, an anthracene ring, or a phenanthrene ring.

[0063] 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.

[0064] 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.

[0065] In this application, the number of carbon atoms in the substituted or unsubstituted heteroaryl group (hybrid aryl 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 other embodiments, the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group with a total carbon number of 3 to 30; and in still other embodiments, the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group with a total carbon number of 5 to 12.

[0066] In this application, the heteroaryl groups that serve as substituents for Ar1, Ar2, Ar4, Ar5, Ar6, L, L1, L2, L3, L4, and L5 are, for example but not limited to, pyridyl, carbazolyl, quinolinyl, isoquinolinyl, phenantholinyl, benzoxazolyl, benzothiazolyl, benzoimidazolyl, dibenzothiophene, and dibenzofuranyl.

[0067] 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.

[0068] 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.

[0069] In this application, the halogen group may be, for example, fluorine, chlorine, bromine, or iodine.

[0070] In this application, specific examples of trialkylsilyl groups include, but are not limited to, trimethylsilyl, triethylsilyl, etc.

[0071] In this application, specific examples of alkyl halogens include, but are not limited to, trifluoromethyl.

[0072] In this application, specific examples of deuterated alkyl groups include, but are not limited to, trideuterated methyl groups.

[0073] In this application, deuterated aryl refers to an aryl group having a deuteration, such as, but not limited to, deuterated phenyl, deuterated naphthyl, deuterated biphenyl, etc.

[0074] In this application, halogenated aryl refers to an aryl group with a halogen substituent, such as, but not limited to, fluorophenyl, fluoronaphthyl, fluorobiphenyl, etc.

[0075] In this application, the number of carbon atoms in cycloalkyl groups with 3 to 10 carbon atoms can be, for example, 3, 4, 5, 6, 7, 8, or 10. Specific examples of cycloalkyl groups include, but are not limited to, cyclopentyl, cyclohexyl, and adamantyl.

[0076] 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.

[0077]

[0078]

[0079] 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.

[0080]

[0081] 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):

[0082]

[0083] In some embodiments, the fused-ring compound has the structures shown in formulas (1-1) to (1-4):

[0084]

[0085] In some embodiments, rings E, F, P, and Q are each independently selected from benzene rings, naphthalene rings, or phenanthrene rings.

[0086] Alternatively, rings E, F, P, and Q can each be independently selected from the following structures:

[0087] The location indicates the fusion site.

[0088] In some embodiments, Het is selected from the following groups:

[0089]

[0090]

[0091] -# represents the bond connected to L, represents the bond connected to L1, represents the bond connected to L2; the formula does not contain then it represents the one connected at this position wherein, L2 is a single bond and Ar2 is hydrogen.

[0092] Optionally, Het is selected from the following groups:

[0093]

[0094] -# represents the bond connected to L, represents the bond connected to L1, represents the bond connected to L2; the formula does not contain then it represents the one connected at this position wherein, L2 is a single bond and Ar2 is hydrogen.

[0095] In some embodiments, L, L1, L2, L3, L4 and L5 are the same or different, and each independently selected from a single bond, a substituted or unsubstituted arylene having 6 to 15 carbon atoms, a substituted or unsubstituted heteroarylene having 5 to 18 carbon atoms.

[0096] In some embodiments, L, L1, L2, L3, L4 and L5 are the same or different, and each independently selected from a single bond, a substituted or unsubstituted arylene having 6, 7, 8, 9, 10, 11, 12, 13, 14 or 15 carbon atoms, a substituted or unsubstituted heteroarylene having 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17 or 18 carbon atoms.

[0097] Optionally, the substituents in L, L1, L2, L3, L4 and L5 are each independently selected from deuterium, fluorine, cyano, an alkyl group having 1 to 5 carbon atoms, a trialkylsilyl group having 3 to 8 carbon atoms, a fluoroalkyl group having 1 to 4 carbon atoms, a deuterated alkyl group having 1 to 4 carbon atoms, phenyl or naphthyl.

[0098] In some embodiments, L, L1, L2, L3, L4 and L5 are the same or different, and each independently selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted phenanthrylene, a substituted or unsubstituted fluorene, a substituted or unsubstituted dibenzothiophene, a substituted or unsubstituted dibenzofuran, a substituted or unsubstituted carbazole.

[0099] Optionally, the substituents in L, L1, L2, L3, L4 and L5 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.

[0100] In some embodiments, L is selected from the group consisting of single bonds or the following groups:

[0101]

[0102] In some embodiments, L3 is selected from the group consisting of single bonds or the following groups:

[0103]

[0104] In some embodiments, L1, L2, L4, and L5 are each independently selected from the group consisting of single bonds or the following groups:

[0105]

[0106] In some embodiments, Ar1, Ar4, Ar5, and Ar6 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 7 to 20 carbon atoms; Ar2 is selected from hydrogen, substituted or unsubstituted aryl groups having 6 to 25 carbon atoms, or substituted or unsubstituted heteroaryl groups having 7 to 20 carbon atoms.

[0107] In some embodiments, Ar1, Ar4, Ar5, and Ar6 are each independently selected from substituted or unsubstituted aryl groups having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, or 25 carbon atoms, and substituted or unsubstituted heteroaryl groups having 7, 8, 9, 10, 12, 13, 14, 15, 16, 17, 18, 19, or 20 carbon atoms.

[0108] Optionally, Ar2 is selected from hydrogen, 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 7, 8, 9, 10, 12, 13, 14, 15, 16, 17, 18, 19 or 20 carbon atoms.

[0109] In some embodiments, the substituents in Ar1, Ar2, Ar4, Ar5, and Ar6 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 12 carbon atoms, heteroaryl groups with 5 to 12 carbon atoms, and trialkylsilyl groups with 3 to 8 carbon atoms. Optionally, any two adjacent substituents form a benzene ring or a fluorene ring.

[0110] In some embodiments, Ar1, Ar4, Ar5, and Ar6 are each independently selected from substituted or unsubstituted groups V; Ar2 is selected from hydrogen, substituted or unsubstituted groups V; wherein the unsubstituted group V is selected from the group consisting of:

[0111]

[0112] The substituted group V 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, dibenzothiophenyl, carbazoleyl, benzoxazolyl, or benzothiazolyl, and when the number of substituents on group V is greater than 1, the substituents may be the same or different.

[0113] In some embodiments, Ar1, Ar4, and Ar5 are selected from the group consisting of: ; Ar2 is selected from hydrogen or the group consisting of:

[0114]

[0115] In some embodiments, Ar6 is selected from the group consisting of:

[0116]

[0117] In some embodiments, Ar3 is selected from the group consisting of:

[0118]

[0119] In some embodiments, Ar3 is selected from the group consisting of:

[0120]

[0121]

[0122] In some implementations... Selected from the following groups:

[0123]

[0124]

[0125] In some implementations... and Each is independently selected from the following groups, Selected from hydrogen or the following groups:

[0126]

[0127] In some embodiments, group A is selected from the following groups:

[0128]

[0129]

[0130] 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 deuterium, cyano, trideuterated methyl, trimethylsilyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl or phenyl.

[0131] Optionally, the fused-ring compound is selected from the group consisting of the following compounds:

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150] 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 fused ring compound described in the first aspect of this application.

[0151] The fused ring compounds provided in this application can be used to form at least one organic film layer in a functional layer to improve the luminous efficiency and lifetime of organic electroluminescent devices.

[0152] Optionally, the functional layer includes an organic light-emitting layer, which comprises the fused-ring compound. The organic light-emitting layer may be composed of the fused-ring compound provided in this application, or it may be composed of the fused-ring compound provided in this application and other materials.

[0153] According to a specific implementation method, such as Figure 1 As shown, the organic electroluminescent device may include an anode 100, a hole injection layer 310, a first hole transport layer 321, a second hole transport layer (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.

[0154] 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.

[0155] In this application, the hole transport layer may include one or more hole transport materials. The 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:

[0156]

[0157] In one embodiment, the first hole transport layer 321 is composed of HT-1.

[0158] In one embodiment, the second hole transport layer 322 is composed of HT-2 or HT-3.

[0159] 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;

[0160]

[0161] In one embodiment, the hole injection layer 310 is composed of a PD.

[0162] 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.

[0163] The host material of the organic light-emitting layer 330 may comprise metal chelating compounds, bis(styrene) derivatives, aromatic amine derivatives, dibenzofuran derivatives, or other types of materials. Optionally, the host material comprises the fused-ring compounds of this application.

[0164] 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,

[0165]

[0166]

[0167] In one embodiment of this application, the organic electroluminescent device is a red organic electroluminescent device. In a more specific embodiment, the host material of the organic light-emitting layer 330 comprises the fused-ring compound of this application. The guest material is, for example, RD-1 or GD.

[0168] 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 fused-ring compound of this application. The guest material may be, for example, fac-Ir(ppy)3.

[0169] 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:

[0170]

[0171] In one embodiment of this application, the electron transport layer 340 may be composed of ET-1 and LiQ, or ET-2 and LiQ.

[0172] 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.

[0173] 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).

[0174] A third aspect of this application provides an electronic device including the organic electroluminescent device described in the second aspect of this application.

[0175] According to one implementation method, such as Figure 2As 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.

[0176] The following synthetic examples illustrate the synthetic method of the fused ring compounds of this application, but this disclosure is not limited thereto.

[0177] Synthesis Examples

[0178] 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.

[0179] Synthesis of Sub-a1:

[0180]

[0181] Under a nitrogen atmosphere, 9-phenanthreneboronic acid (12.21 g, 55 mmol), o-bromonitrobenzene (10.10 g, 50 mmol), tetrakis(triphenylphosphine)palladium (Pd(PPh3)4, 0.58 g, 0.5 mmol), anhydrous potassium carbonate (13.82 g, 100 mmol), toluene (120 mL), anhydrous ethanol (30 mL), and deionized water (30 mL) were added sequentially to a 500 mL three-necked flask. Stirring and heating were initiated, and the mixture was refluxed for 16 h. After cooling to room temperature, the mixture was extracted with dichloromethane (100 mL × 3 times). The organic phases were combined and dried over anhydrous sodium 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 / dichloromethane as the mobile phase to give a white solid Sub-a1 (11.67 g, yield 78%).

[0182] Sub-a2 to Sub-a4 were synthesized using the same method as Sub-a1, except that reactant A shown in Table 1 was used instead of o-bromonitrobenzene.

[0183] Table 1: Synthesis of Sub-a2 to Sub-a4

[0184]

[0185] Synthesis of Sub-b1:

[0186]

[0187] Under a nitrogen atmosphere, Sub-a1 (14.96 g, 50 mmol), triphenylphosphine (32.78 g, 125 mmol), and o-dichlorobenzene (150 mL) were added to a 250 mL three-necked flask. Stirring and heating were initiated, and the mixture was refluxed for 16 h. After cooling to room temperature, 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 give a white solid, Sub-b1 (7.48 g, 56% yield).

[0188] Sub-b2 to Sub-b4 were synthesized using the same method as Sub-a1, except that reactant B shown in Table 2 was used instead of Sub-a1.

[0189] Table 2: Synthesis of Sub-b2 to Sub-b4

[0190]

[0191] Synthesis of Sub-c1:

[0192]

[0193] Under a nitrogen atmosphere, Sub-b1 (13.36 g, 50 mmol), 2,4-dichloro-1-iodobenzene (15.00 g, 55 mmol), tris(dibenzylideneacetone)palladium (Pd2(dba)3, 0.916 g, 1 mmol), 2-dicyclohexylphosphine-2′,4′,6′triisopropylbiphenyl (XPhos, 0.95 g, 2 mmol), sodium tert-butoxide (9.61 g, 100 mmol), and toluene (150 mL) were added sequentially to a 500 mL three-necked flask. The mixture was heated to reflux and stirred overnight. 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 sodium sulfate. The solvent was removed by filtration and vacuum distillation to obtain the crude product. The crude product was purified by silica gel column chromatography using n-heptane / dichloromethane as the mobile phase to give a white solid Sub-c1 (15.05 g, yield 73%).

[0194] Sub-c2 to Sub-c7 were synthesized using the same method as Sub-c1, except that reactant C shown in Table 3 was used instead of Sub-b1, and reactant D was used instead of 2,4-dichloro-1-iodobenzene.

[0195] Table 3: Synthesis of Sub-c2 to Sub-c11

[0196]

[0197]

[0198] Synthesis of Sub-d1:

[0199]

[0200] Under a nitrogen atmosphere, Sub-c1 (10.31 g, 25 mmol), dichlorobis(tricyclohexylphosphine)palladium (0.92 g, 1.25 mmol), tert-valeric acid (5.10 g, 50 mmol), cesium carbonate (16.29 g, 50 mmol), and dimethylacetamide (100 mL) were added to a 250 mL three-necked flask. The mixture was heated to reflux and stirred for 6 hours. After the reaction system cooled to room temperature, the organic layer was extracted with dichloromethane (50 mL × 3 times). The organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the solvent was removed by vacuum distillation to obtain the crude product. The crude product was purified by silica gel column chromatography using n-heptane / ethyl acetate as the mobile phase to give a white solid Sub-d1 (3.94 g, yield 42%).

[0201] Sub-d2 to Sub-d7 were synthesized using the same method as Sub-d1, except that reactant E shown in Table 4 was used instead of Sub-c1.

[0202] Table 4: Synthesis of Sub-d2 to Sub-d7

[0203]

[0204]

[0205] Synthesis of Sub-e1:

[0206]

[0207] Under a nitrogen atmosphere, Sub-d1 (18.79 g, 50 mmol), pinacol diborate (15.24 g, 60 mmol), potassium acetate (10.80 g, 110 mmol), and 1,4-dioxane (180 mL) were added sequentially to a 500 mL three-necked flask. Stirring and heating were initiated, and the system was heated to 40 °C. Tris(dibenzylacetone)dipalladium (0.46 g, 0.5 mmol) and 2-dicyclohexylphosphine-2′,6′-dimethoxy-1,1′-dibiphenyl (SPhos, 0.41 g, 1.0 mmol) were then rapidly added. The mixture was further heated to reflux and stirred overnight. After cooling to room temperature, 200 mL of water was added, and the mixture was stirred thoroughly for 30 min. The mixture was then filtered under reduced pressure, and the filter cake was collected. The filter cake was dissolved in dichloromethane and dried over anhydrous sodium sulfate. After filtration, the solvent was removed by reduced pressure distillation to obtain the crude product. The crude product was purified by silica gel column chromatography using n-heptane / dichloromethane as the mobile phase, finally yielding a white solid Sub-e1 (17.29 g, yield 74%).

[0208] Sub-e2 to Sub-e7 were synthesized using the same method as Sub-e1, except that reactant F shown in Table 5 was used instead of Sub-d1.

[0209] Table 5: Synthesis of Sub-e2 to Sub-e7

[0210]

[0211]

[0212] Synthesis of Sub-f1:

[0213]

[0214] Under a nitrogen atmosphere, Sub-e1 (23.37 g, 50 mmol), m-chlorobromobenzene (9.57 g, 50 mmol), tetrakis(triphenylphosphine)palladium (Pd(PPh3)4, 0.58 g, 0.5 mmol), anhydrous potassium carbonate (13.82 g, 100 mmol), toluene (240 mL), anhydrous ethanol (60 mL), and deionized water (60 mL) were added sequentially to a 500 mL three-necked flask. Stirring and heating were initiated, and the mixture was refluxed for 16 h. After cooling to room temperature, the mixture was extracted with dichloromethane (100 mL × 3 times). The organic phases were combined and dried over anhydrous sodium 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 / dichloromethane as the mobile phase to obtain a white solid, Sub-f1 (17.85 g, yield 79%).

[0215] Sub-f2 to Sub-f17 were synthesized using the same method as Sub-f1, except that reactant G, as shown in Table 6, was used instead of Sub-e1, and reactant H was used instead of m-chlorobromobenzene.

[0216] Table 6: Synthesis of Sub-f2 to Sub-f17

[0217]

[0218]

[0219] Synthesis of Sub-g1:

[0220]

[0221] Under a nitrogen atmosphere, Sub-f1 (11.29 g, 25 mmol), pinacol diborate (7.62 g, 30 mmol), potassium acetate (5.40 g, 55 mmol), and 1,4-dioxane (120 mL) were added sequentially to a 500 mL three-necked flask. Stirring and heating were initiated, and the system was heated to 40 °C. Tris(dibenzylacetone)dipalladium (0.43 g, 0.25 mmol) and 2-biscyclohexylphosphine-2′,6′-dimethoxy-1,1′-dibiphenyl (SPhos, 0.21 g, 0.5 mmol) were then rapidly added. The mixture was further heated to reflux and stirred overnight. After cooling to room temperature, 200 mL of water was added, and the mixture was stirred thoroughly for 30 min. The mixture was then filtered under reduced pressure to obtain the crude product. The crude product was dissolved in dichloromethane and dried over anhydrous sodium sulfate. After filtration, the solvent was removed by reduced pressure distillation to obtain the crude product. The crude product was purified by silica gel column chromatography using n-heptane / dichloromethane as the mobile phase, and finally a white solid sub-g1 (8.42 g, yield 62%) was obtained.

[0222] Sub-g2 to Sub-g13 were synthesized using the same method as Sub-g1, except that reactant J shown in Table 7 was used instead of Sub-f1.

[0223] Table 7: Synthesis of Sub-g2 to Sub-g13

[0224]

[0225]

[0226] Synthesis of compound A-12:

[0227]

[0228] Under a nitrogen atmosphere, Sub-d2 (9.40 g, 25 mmol), RA-1 (CAS: 897671-78-2, 7.75 g, 26.25 mmol), tris(dibenzylacetone)palladium (0.46 g, 0.5 mmol), 2-bicyclohexylphosphine-2′,6′-dimethoxy-1,1′-diphenyl (SPhos, 0.41 g, 1 mmol), sodium tert-butoxide (4.8 g, 50 mmol), and xylene (100 mL) were added sequentially to a 500 mL three-necked flask. The mixture was heated to reflux and stirred overnight. After the system cooled to room temperature, it was extracted with dichloromethane (50 mL × 3 times). The organic phases were combined and dried over anhydrous sodium sulfate. The solvent was removed by filtration under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography using n-heptane / dichloromethane as the mobile phase to give a white solid, compound A-12 (8.25 g; yield 52%), m / z = 635.2 [M+H]. + .

[0229] The compound of this application was synthesized using the same method as compound A-12, except that reactant K was used instead of Sub-d2 and reactant L was used instead of RA-1. The synthesized compound, its yield, and mass spectrometry characterization results are shown in Table 8.

[0230] Table 8: Synthesis of the compounds in this application

[0231]

[0232]

[0233]

[0234]

[0235] Synthesis of compound B-5:

[0236]

[0237] Under a nitrogen atmosphere, RM-2 (CAS: 1883265-40-4, 9.35 g, 25 mmol), Sub-g6 (14.95 g, 27.5 mmol), tetrakis(triphenylphosphine)palladium (Pd(PPh3)4, 0.29 g, 0.25 mmol), anhydrous potassium carbonate (6.91 g, 50 mmol), toluene (140 mL), tetrahydrofuran (35 mL), and deionized water (35 mL) were added sequentially to a 500 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 and dried over anhydrous sodium 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 / dichloromethane as the mobile phase to give a white solid, namely compound B-5 (10.0 g, yield 53%), m / z = 755.2 [M+H]. + .

[0238] The compound of this application was synthesized using the same method as compound B-5, except that reactant M was used instead of RM-2 and reactant N was used instead of Sub-g6. The synthesized compound, its yield, and mass spectrometry characterization results are shown in Table 9.

[0239] Table 9: Synthesis of the compounds in this application

[0240]

[0241]

[0242]

[0243]

[0244]

[0245] NMR data for some compounds:

[0246] NMR of compound A-51: 1 H-NMR(400MHz,CD2Cl2)δppm 8.51(d,1H),8.22-8.08(m,5H),8.01(d,1H),7.97-7.93(m,2H),7.68(d,1H),7.62(t,1H),7.5 6-7.37(m,12H),7.32(t,1H),7.26(s,1H),7.18(t,1H),7.06(d,1H),6.63(d,1H),6.46(d,2H).

[0247] NMR of compound B-50: 1H-NMR(400MHz,CD2Cl2)δppm 8.88(s,1H),8.76(s,1H),8.69(d,1H),8.63(d,1H),8.53(d,1H),8.37(d,1H),8.28(d,1H),8.21-8.16(m,2H),8.11(t,1H),8.05-7.98(m 5H),7.92-7.86(m,2H),7.79-7.72(m,3H),7.70-7.43(m,8H),7.42-7.31(m,3H),7.18(t,1H).

[0248] Fabrication and evaluation of organic electroluminescent devices:

[0249] Example 1: Red Organic Electroluminescent Device

[0250] 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. Organic solvents are used to clean the surface of the ITO substrate to remove impurities and oil stains.

[0251] PD was vacuum-deposited on the experimental substrate (anode) to form a thickness of [thickness value missing]. 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]. The first hole transport layer.

[0252] The compound HT-2 was vacuum-deposited on the first hole transport layer to form a thickness of [missing information]. The second hole transport layer.

[0253] Next, on the second hole transport layer, compound A-12:RH-N:RD-1 was co-deposited at a deposition rate ratio of 49%:49%:2% to form a layer with a thickness of [missing information]. The red light emitting layer (EML).

[0254] On the light-emitting layer, compound ET-1 and LiQ are mixed in a 1:1 weight ratio and deposited by vapor deposition. 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.

[0255] Furthermore, CP-1 is vacuum-deposited onto the aforementioned cathode to form a thickness of [missing information]. The coating layer is used to complete the fabrication of the red organic electroluminescent device.

[0256] Examples 2-27

[0257] Except that, when fabricating the light-emitting layer, compound X from Table 10 is used instead of compound A-12 in Example 1, the organic electroluminescent device is prepared using the same method as in Example 1.

[0258] Comparative Examples 1-3

[0259] Except that, when fabricating the light-emitting layer, compounds A, B, and C were used instead of compound A-12 in Example 1, the organic electroluminescent device was prepared using the same method as in Example 1.

[0260] The compounds used in Examples 1-27 and Comparative Examples 1-3 have the following structures:

[0261]

[0262]

[0263] The performance of the red organic electroluminescent devices prepared in Examples 1-27 and Comparative Examples 1-3 was tested, specifically at 10 mA / cm². 2 The IVL performance of the device was tested under the specified conditions. The lifetime of the T95 device was 20 mA / cm. 2 The test was conducted under the specified conditions, and the test results are shown in Table 10.

[0264] Table 10

[0265]

[0266]

[0267] As can be seen from Table 10 above, when the compound of the present invention is used as the hole transport host material of a red organic electroluminescent device, the luminous efficiency of the device is increased by at least 14.2% and the T95 lifetime is increased by at least 12.7%.

[0268] Example 28: Red Organic Electroluminescent Device

[0269] 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. Organic solvents are used to clean the surface of the ITO substrate to remove impurities and oil stains.

[0270] PD was vacuum-deposited on the experimental substrate (anode) to form a thickness of [thickness value missing]. 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]. The first hole transport layer.

[0271] Compound HT-3 was vacuum-deposited onto the first hole transport layer to form a thickness of [missing information]. The second hole transport layer.

[0272] Next, on the second hole transport layer, compound B-5:RD-1 was co-deposited at a deposition rate of 98%:2% to form a layer with a thickness of [missing information]. The red light emitting layer (EML).

[0273] On the light-emitting layer, compounds ET-2 and LiQ are mixed in a 1:1 weight ratio and deposited by vapor deposition. 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.

[0274] Furthermore, CP-1 is vacuum-deposited onto the aforementioned cathode to form a thickness of [missing information]. The coating layer is used to complete the fabrication of the red organic electroluminescent device.

[0275] Examples 29-57

[0276] Except that, when fabricating the light-emitting layer, compound Y from Table 11 is used instead of compound B-5 in Example 28, the organic electroluminescent device is prepared using the same method as in Example 28.

[0277] Comparative Examples 4-6

[0278] Except that, when fabricating the light-emitting layer, compounds D, E, and F were used instead of compound B-5 in Example 28, the organic electroluminescent device was prepared using the same method as in Example 28.

[0279] The compounds used in Examples 28-57 and Comparative Examples 4-6 have the following structures:

[0280]

[0281] The performance of the red organic electroluminescent devices prepared in Examples 28-57 and Comparative Examples 4-6 was tested, specifically at 10 mA / cm². 2 The IVL performance of the device was tested under the specified conditions. The lifetime of the T95 device was 20 mA / cm. 2The test was conducted under the specified conditions, and the test results are shown in Table 11.

[0282] Table 11

[0283]

[0284]

[0285] As can be seen from Table 11 above, when the compound of the present invention is used as the bipolar light-emitting host material of a red organic electroluminescent device, the luminous efficiency of the device is increased by at least 10.3% and the T95 lifetime is increased by at least 14.7%.

[0286] The reason for the above test results lies in the fact that the compounds in this application include a macrocyclic fused-ring core structure formed by phenanthreneindole and a benzene ring. This core is connected to a triarylamine, a carbazole group, or a nitrogen-containing electron-deficient heteroaryl group. Specifically, the benzene ring attached to the nitrogen atom in the core is covalently connected to the carbon atom at position 1 of the phenanthrene ring. This specific connection method forms a fused-ring macrocyclic structure with a large conjugated system, thereby endowing the phenanthreneindole group with superior hole transport capability. When the compounds of this application are used as hole transport materials in hybrid host materials or as a single host material, they can improve carrier balance in the luminescent layer, broaden the carrier recombination region, improve exciton generation and utilization efficiency, and enhance the luminous efficiency and lifetime of the device. When the parent nucleus is attached to a triarylamine or carbazole group, the hole transport capability of the compound can be further improved, making the compound more suitable as a hole transport host material in a mixed host material; when the parent nucleus is attached to a nitrogen-containing electron-deficient heteroaryl group, it is more suitable as a bipolar host material with excellent electron and hole transport capabilities.

[0287] 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. A fused-ring compound, characterized in that, It has a structure as shown in equation (1-1) or (1-2): Group A is selected from the groups shown in a-1, a-2, or a-3: L, L1, L2, L3, L4 and L5 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 phenanthylene, substituted or unsubstituted fluorene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl; The substituents in L, L1, L2, L3, L4 and L5 may be the same or different, and each is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl or phenyl; Ar3 is selected from the group shown in a-4 or a-5: Rings E, F, P, and Q are each independently selected from benzene rings and naphthalene rings; Het is selected from the following groups: -# represents the key connected to L, represents the key connected to L1, represents the key connected to L2; the formula does not contain if it is not, it represents the connection at this position in which, L2 is a single bond and Ar2 is hydrogen; Ar1, Ar4, Ar5, and Ar6 are each independently selected from substituted or unsubstituted groups V; Ar2 is selected from hydrogen, substituted or unsubstituted groups V; wherein the unsubstituted groups V are selected from the group consisting of: The substituted group V has one or more substituents, and each substituent in group V is independently selected from deuterium, fluorine, cyano, trideuterated methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, and naphthyl. When the number of substituents on group V is greater than 1, the substituents may be the same or different. Each of R1, R2, R3, R4, R5, R6 and R7 may be the same or different, and each is independently selected from deuterium, cyano, trideuterated methyl, trimethylsilyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl or phenyl; n1, n2, and n3 are each independently selected from 0, 1, 2, 3, or 4; n4 is selected from 0, 1, 2, or 3; n5, n6 and n7 are each independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8.

2. The fused-ring compound according to claim 1, wherein, Het is selected from the following groups: - # represents the key connected to L, represents the key connected to L1, represents the key connected to L2; the formula does not contain if not, it represents the where L2 is a single bond and Ar2 is hydrogen.

3. The fused-ring compound according to claim 1, wherein, Ar3 is selected from the group consisting of the following groups:

4. The fused-ring compound according to claim 1, wherein, Selected from the following groups:

5. The fused-ring compound according to claim 1, wherein, Each is independently selected from the following groups, Selected from hydrogen or the following groups:

6. The fused-ring compound according to claim 1, wherein, Group A is selected from the following groups:

7. The fused-ring compound according to claim 1, wherein, The fused-ring compound is selected from the group consisting of the following compounds:

8. 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 the fused ring compound according to any one of claims 1 to 7.

9. The organic electroluminescent device according to claim 8, characterized in that, The functional layer includes an organic light-emitting layer, which contains the fused ring compound.

10. An electronic device, characterized in that, It includes the organic electroluminescent device as described in claim 8 or 9.

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