Organic compound, organic electroluminescent device and electronic apparatus

By using an organic compound with a fused structure of benzo[5,6]phenanthrene[2,1-b]benzofuran and triazine as the host material for red light, the problem of low efficiency in existing organic electroluminescent devices has been solved, and the device performance has been improved.

WO2026007592A1PCT designated stage Publication Date: 2026-01-08SHAANXI LIGHTE OPTOELECTRONICS MATERIAL CO LTD
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Patent Information

Application Number
PCT/CN2025/098892
Authority / Receiving Office
WO · WO
Patent Type
Applications
Current Assignee / Owner
Priority Date
2024-07-02
Filing Date
2025-06-03
Publication Date
2026-01-08

AI Technical Summary

Technical Problem

Existing organic electroluminescent devices have low internal quantum efficiency. Traditional fluorescent materials can only emit light using 25% of singlet excitons. Although phosphorescent materials have high efficiency, their device performance still needs further improvement.

Method used

An organic compound is provided, which adopts a fused structure of benzo[5,6]phenanthrene[2,1-b]benzofuran and triazine, and the triazine is connected by replacing the triazine with dibenzofuran or dibenzothiophene group, thereby improving the molecular flatness and intermolecular forces, making it suitable as a host material for red light.

Benefits of technology

It improves the luminous efficiency and lifetime of the device, reduces the driving voltage, and enhances electron mobility.

✦ Generated by Eureka AI based on patent content.

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Abstract

The present application belongs to the technical field of organic electroluminescence, and relates to an organic compound, and an organic electroluminescent device and an electronic apparatus using same. The organic compound has a structure as represented by formula (1). The organic compound is used in the organic electroluminescent device, and can significantly improve the performance of the organic electroluminescent device.
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Description

Organic compound, organic electroluminescent device and electronic device

[0001] Cross-reference to related applications

[0002] This application claims priority to Chinese Patent Application No. 202410883271.X, filed on July 2, 2024, the contents of which are incorporated herein in their entirety. TECHNICAL FIELD

[0003] The present application relates to the technical field of organic compounds, in particular to an organic compound, an organic electroluminescent device and an electronic device. BACKGROUND

[0004] Since 1987, organic electroluminescent devices (OLEDs) have gradually become the next generation of flat panel display technology recognized by the industry. OLEDs belong to self-emitting devices. When charges (electrons and holes) are injected into the organic film between the anode and the cathode, electrons and holes recombine to form excitons and transfer energy to light-emitting molecules, thereby exciting electrons to transition from the ground state to the excited state. The excited state energy is deactivated by radiation to emit light. OLEDs have the advantages of self-emission, low driving voltage, thinness, wide light-emitting viewing angle, fast response speed, bendable folding, low energy consumption, and large-area production, thus having broad application prospects in the fields of information display and solid-state lighting. Traditional organic fluorescent materials can only utilize 25% of the singlet excitons formed by electrical excitation to emit light, and the internal quantum efficiency of the device is relatively low (the highest is 25%). The external quantum efficiency is generally lower than 5%, which is still far from the efficiency of phosphorescent devices. Phosphorescent materials can effectively utilize singlet and triplet excitons formed by electrical excitation to emit light due to the strong spin-orbit coupling of heavy atom centers, which can effectively utilize singlet and triplet excitons formed by electrical excitation to emit light, making the internal quantum efficiency of the device reach 100%.

[0005] The prior art discloses a host material that can be used to prepare an organic light-emitting layer in an organic electrophosphorescent light-emitting device. However, there is still a need to continue to develop new materials to further improve the performance of organic electroluminescent devices. SUMMARY

[0006] To solve the above problems, the present application aims to provide an organic compound, an organic electroluminescent device and an electronic device, which can improve the performance of the organic electroluminescent device and the electronic device, such as reducing the driving voltage of the device, improving the efficiency and lifetime of the device.

[0007] In a first aspect, the present application provides an organic compound having a structure as shown in formula 1:

[0008] wherein D represents deuterium;

[0009] n and m are the number of D, n is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; m is selected from 0, 1, 2 or 3;

[0010] L, L1 and L2 are the same or different, and each is independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;

[0011] Ar1 is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;

[0012] Ar2 is a group represented by formula 2;

[0013] Y is O or S;

[0014] each R1 and each R2 are the same or different, and each is independently selected from deuterium, a halogen, a cyano group, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms;

[0015] n1 is the number of R1, and is selected from 0, 1, 2 or 3, and when n1 is greater than 1, any two R1 are the same or different;

[0016] n2 is the number of R2, and is selected from 0, 1, 2, 3 or 4, and when n2 is greater than 1, any two R2 are the same or different;

[0017] the substituents in L, L1, L2 and Ar1 are the same or different, and each is independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms.

[0018] In a second aspect, the present application provides an organic electroluminescence device, comprising an anode and a cathode arranged oppositely, and a functional layer arranged between the anode and the cathode; the functional layer comprises the organic compound disclosed in the first aspect of the present application.

[0019] In a third aspect, the present application provides an electronic device comprising the organic electroluminescence device disclosed in the second aspect of the present application.

[0020] The organic compound provided by the present application is a benzo[5,6]phenanthro[2,1-b]benzofuran and the triazine must be connected with a dibenzofuranyl group or a dibenzothiophenyl group, which can effectively avoid the intermolecular stacking and improve the film-forming property of the compound. The special fused mode of the phenanthro[5,6]phenanthro[2,1-b]benzofuran in the compound of the present application ensures that the benzofuro[5,6]phenanthro[2,1-b]benzofuran has a relatively appropriate first excited triplet energy level, which is suitable as a fragment of a red light host material. On the other hand, the connection of the benzofuro[5,6]phenanthro[2,1-b]benzofuran and the triazine substituted with a dibenzofuranyl group or a dibenzothiophenyl group can make the compound molecule more flat, which is conducive to the stacking of the molecules and can enhance the intermolecular force and improve the electron mobility of the compound. Therefore, when the organic compound of the present application is used as a red light host material, the luminous efficiency and the service life of the device can be significantly improved.

[0021] Other features and advantages of the present application will be described in detail in the following specific embodiments BRIEF DESCRIPTION OF DRAWINGS

[0022] The accompanying drawings are included to provide a further understanding of the present application, and constitute a part of the specification, and are used to explain the present application together with the following specific embodiments, but do not constitute a limitation on the present application.

[0023] FIG. 1 is a schematic structural diagram of an organic electroluminescent device of the present application.

[0024] FIG. 2 is a schematic structural diagram of an electronic device of the present application.

[0025] Reference numerals 100, anode 200, cathode 300, functional layer 310, hole injection layer 320, hole transport layer 330, light-emitting adjustment layer 340, organic light-emitting layer 350, electron transport layer 360, electron injection layer 400, electronic device DETAILED DESCRIPTION

[0026] In view of the above problems existing in the prior art, the purpose of the present application is to provide an organic compound, an organic electroluminescent device and an electronic device, which can improve the performance of the organic electroluminescent device and the electronic device, such as reducing the driving voltage of the device, improving the efficiency and service life of the device.

[0027] In a first aspect of the present application, an organic compound having a structure as shown in formula 1 is provided:

[0028] wherein D represents deuterium;

[0029] n and m are the number of D, n is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; m is selected from 0, 1, 2 or 3;

[0030] L, L1and L2are the same or different, and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;

[0031] Ar1is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;

[0032] Ar2is a group represented by formula 2;

[0033] Y is O or S;

[0034] Each R1and each R2are the same or different, and are each independently selected from deuterium, a halogen, a cyano group, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms;

[0035] n1is the number of R1, and is selected from 0, 1, 2 or 3, and when n1is greater than 1, any two R1are the same or different;

[0036] n2is the number of R2, and is selected from 0, 1, 2, 3 or 4, and when n2is greater than 1, any two R2are the same or different;

[0037] The substituents in L, L1, L2and Ar1are the same or different, and are each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms.

[0038] In the present application, the description manner "each... is independently" and "each... is independently selected from" can be interchangeable, and should be interpreted in a broad sense, which can mean that in different groups, the specific options expressed by the same symbols do not affect each other, or in the same group, the specific options expressed by the same symbols do not affect each other. For example, "each R1is independently selected from a halogen, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms" can be expressed as "each R1is independently selected from a halogen, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms". wherein each q is independently 0, 1, 2, or 3, and each R" is independently selected from hydrogen, deuterium, fluorine, chlorine, the meaning of which is that formula Q-1 represents a benzene ring having q number of substituents R", each of which can be the same or different, and the options for each R" are independent of each other; and formula Q-2 represents a biphenyl having q number of substituents R" on each of the benzene rings, the number q of R" substituents on the two benzene rings can be the same or different, and each R" can be the same or different, and the options for each R" are independent of each other.

[0039] In the present application, the term "substituted or unsubstituted" used herein means that the functional group recited after the term can or can not have a substituent (hereinafter, the substituents are collectively referred to as Rc). For example, "substituted or unsubstituted aryl" means aryl having a substituent Rc, or aryl having no substituent. The substituents Rc are, for example, deuterium, a halogen group, a cyano group, an alkyl group, a haloalkyl group, a deuterated alkyl group, a cycloalkyl group, an aryl group, a heteroaryl group, a deuterated aryl group, and the like. The number of substitutions can be one or more.

[0040] In the present application, a non-positioning connecting bond means a single bond extending from a ring system which means that one end of the connecting bond can be connected to any position in the ring system through which the bond passes, and the other end is connected to the rest of the molecule.

[0041] For example, as shown in the following formula (f), the naphthyl group represented by formula (f) is connected to the rest of the molecule through two non-positioning connecting bonds that pass through the bicyclic ring, the meaning of which includes any of the possible connection modes shown in formulae (f-1) to (f-10).

[0042] For another example, as shown in the following formula (X'), the dibenzofuranyl group represented by formula (X') is connected to the rest of the molecule through a non-positioning connecting bond extending from the middle of one of the benzene rings, the meaning of which includes any of the possible connection modes shown in formulae (X'-1) to (X'-4).

[0043] In the present application, a non-positioning substituent means a substituent connected by a single bond extending from the center of a ring system, which means that the substituent can be connected to any possible position in the ring system. For example, as shown in the following formula (Y), the substituent R' represented by formula (Y) is connected to the quinoline ring through a non-positioning connecting bond, the meaning of which includes any of the possible connection modes shown in formulae (Y-1) to (Y-7).

[0044] In the present application, the number of carbon atoms of L, L1, L2, Ar1, R1, and R2 refers to the total number of carbon atoms. For example, if L1 is selected from a substituted arylene group having 12 carbon atoms, the total number of carbon atoms of the arylene group and the substituents thereon is 12.

[0045] In the present application, "alkyl" can include a linear alkyl group or a branched alkyl group. The alkyl group can have 1 to 10 carbon atoms, and in the present application, a numerical range such as "1 to 10" means each integer in the given range; for example, "1 to 10 carbon atoms" means an alkyl group that can include 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10 carbon atoms. Specific examples thereof include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, t-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, heptyl, n-octyl, 2-ethylhexyl, nonyl, decyl, 3,7-dimethyloctyl, and the like.

[0046] In the present application, "cycloalkyl" refers to a group derived from a saturated cyclic carbon chain structure. The cycloalkyl group can have 3 to 10 carbon atoms, and in the present application, a numerical range such as "3 to 10" means each integer in the given range; for example, "5 to 10 carbon atoms" means a cycloalkyl group that can include 5 carbon atoms, 6 carbon atoms, 7 carbon atoms, 8 carbon atoms, 9 carbon atoms, 10 carbon atoms. Alternatively, specific examples of cycloalkyl groups include, but are not limited to, cyclopentyl, cyclohexyl, adamantyl, norbornyl, and the like.

[0047] In the present application, "aryl" refers to an optional functional group or substituent derived from an aromatic carbon ring. The aryl group can be a monocyclic aryl group (e.g., phenyl) or a polycyclic aryl group, in other words, the aryl group can be a monocyclic aryl group, a fused ring aryl group, two or more monocyclic aryl groups connected by a carbon-carbon bond, a monocyclic aryl group and a fused ring aryl group connected by a carbon-carbon bond, two or more fused ring aryl groups connected by a carbon-carbon bond. That is, unless otherwise specified, two or more aromatic groups connected by a carbon-carbon bond can also be considered as an aryl group in the present application. Among them, the fused ring aryl group can include, for example, a bicyclic fused aryl group (such as naphthyl), a tricyclic fused aryl group (such as phenanthryl, fluorenyl, anthryl), and the like. The aryl group does not contain heteroatoms such as B, N, O, S, P, Se, and Si. Examples of the aryl group can include, but are not limited to, phenyl, naphthyl, fluorenyl, spirobifluorenyl, anthryl, phenanthryl, biphenyl, terphenyl, triphenylenyl (also known as benzo[9,10]phenanthryl), perylenyl, pyrenyl, benzofluoranthene, chrysenyl, pyranthrene, indenothiophenyl, indenopyrenyl, indenochrysenyl, indenofluoranthene, indenobenzophenanthrene, indenopyranthrene, indenochrysene, indenonaphthyl, indenonaphthyl, and the like.

[0048] ​In the present application, the number of carbon atoms of a 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, 30, etc. In the present application, a biphenyl group can be understood as an aryl group substituted with a phenyl group, or can be understood as an unsubstituted aryl group. In some embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, in other embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having 6 to 26 carbon atoms, and in other embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

[0049] In the present application, an arylene group refers to a divalent group formed by further losing one hydrogen atom from an aryl group.

[0050] In the present application, a substituted aryl group refers to an aryl group in which one or more hydrogen atoms are replaced with other groups. For example, at least one hydrogen atom is replaced with a deuterium group, a halogen group, a cyano group, an alkyl group, a deuterated alkyl group, a halogenated alkyl group, a cycloalkyl group, an aryl group, a heteroaryl group, a deuterated aryl group, etc. It can be understood that the number of carbon atoms of a substituted aryl group refers to the total number of carbon atoms of the aryl group and the substituents on the aryl group. For example, when Ar1 is the number of carbon atoms is 10.

[0051] In the present application, examples of an aryl group as a substituent include, but are not limited to, a phenyl group, a naphthyl group, etc.

[0052] In the present application, a fluorenyl group can be substituted with one or more substituents. In the case where the above fluorenyl group is substituted, the substituted fluorenyl group can be: etc., but is not limited thereto.

[0053] In the present application, a terphenyl group includes

[0054] In the present application, a heteroaryl group refers to a monovalent aromatic ring or its derivative containing 1, 2, 3, 4, 5, or 6 heteroatoms in the ring, and the heteroatoms can be at least one of B, O, N, P, Si, Se, and S. The heteroaryl group can be a monocyclic heteroaryl group or a polycyclic heteroaryl group, in other words, the heteroaryl group can be a single aromatic ring system or a plurality of aromatic ring systems connected by carbon-carbon bonds, and any of the aromatic ring systems is an aromatic monocyclic ring or an aromatic fused ring. Illustratively, the heteroaryl group can include a thienyl group, a furanyl group, a pyrrolyl group, an imidazolyl group, a thiazolyl group, an oxazolyl group, an oxadiazolyl group, a triazolyl group, a pyridyl group, a bipyridyl group, a pyrimidinyl group, a triazinyl group, an acridinyl group, a pyridazinyl group, a pyrazinyl group, a quinolinyl group, a quinazolinyl group, a quinoxalinyl group, a phenoxazinyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyrazinyl group, a pyrazinopyrazinyl group, an isoquinolinyl group, an indolyl group, a carbazolyl group, a benzoxazolyl group, a benzimidazolyl group, a benzothiazolyl group, a benzcabazolyl group, a benzothiophenyl group, a dibenzothiophenyl group, a thienothiophenyl group, a benzofuranyl group, a phenanthrolinyl group, an isoxazolyl group, a thiadiazolyl group, a benzothiazolyl group, a phenothiazinyl group, a silafluorenyl group, a dibenzofuranyl group, and an N-arylcarbazolyl group (such as an N-phenylcarbazolyl group), an N-heteroarylcarbazolyl group (such as an N-pyridylcarbazolyl group), an N-alkylcarbazolyl group (such as an N-methylcarbazolyl group), and the like, without being limited thereto. Among them, the thienyl group, the furanyl group, the phenanthrolinyl group, and the like are the heteroaryl group of the single aromatic ring system type, and the N-arylcarbazolyl group (such as the N-phenylcarbazolyl group), the N-heteroarylcarbazolyl group are the heteroaryl group of the polycyclic system type connected by carbon-carbon bonds.

[0055] In the present application, the number of carbon atoms of the substituted or unsubstituted heteroaryl group can be selected from 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, or 30. In some embodiments, the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms, in other embodiments, the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group having 5 to 18 carbon atoms, and in other embodiments, the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group having 12 to 18 carbon atoms.

[0056] In the present application, the heteroarylene group referred to is a divalent group formed by further losing one hydrogen atom from the heteroaryl group.

[0057] In the present application, the substituted heteroaryl group can be a heteroaryl group in which one or more than two hydrogen atoms in the heteroaryl group is substituted with a group such as deuterium, a halogen group, a cyano group, an alkyl group, a deuterated alkyl group, a halogenated alkyl group, a cycloalkyl group, an aryl group, a heteroaryl group, a deuterated aryl group, and the like. It should be understood that the number of carbon atoms of the substituted heteroaryl group refers to the total number of carbon atoms of the heteroaryl group and the substituents on the heteroaryl group.

[0058] In the present application, "deuterated" means that at least one hydrogen (H) in a compound or a group is replaced by deuterium (D); specifically, a deuterated compound or a deuterated group can be a compound or a group in which one, more or all available hydrogens are replaced by deuterium.

[0059] In the present application, a halogen group can be fluorine, chlorine, bromine, iodine.

[0060] In the present application, a haloalkyl group can be an alkyl group in which one or more than two hydrogen atoms are replaced by a halogen atom, and specific examples of the haloalkyl group include, but are not limited to, trifluoromethyl.

[0061] In the present application, a deuterated alkyl group can be an alkyl group in which one or more than two hydrogen atoms are replaced by deuterium, and specific examples of the deuterated alkyl group include, but are not limited to, trideuteromethyl.

[0062] In the present application, a deuterated aryl group can be an aryl group in which one or more than two hydrogen atoms (H) are replaced by deuterium (D), and specific examples of the deuterated aryl group include, but are not limited to, pentadeuterophenyl and heptadeuteronaphthyl.

[0063] In some embodiments of the present application, L, L1and L2are the same or different, and each is independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 15 carbon atoms, or a substituted or unsubstituted heteroarylene group having 12 to 18 carbon atoms.

[0064] Optionally, L and L2are the same or different, and each is independently selected from a single bond or a substituted or unsubstituted arylene group having 6 to 12 carbon atoms.

[0065] Optionally, L1is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 15 carbon atoms, or a substituted or unsubstituted heteroarylene group having 12 to 18 carbon atoms.

[0066] Optionally, the substituents in L, L1and L2are the same or different, and each is independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, a phenyl group or a pentadeuterophenyl group.

[0067] In some embodiments of the present application, L, L1and L2are the same or different, and each is independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted carbazolylene group, a substituted or unsubstituted diphenylfuranylene group or a substituted or unsubstituted diphbenzothiophenylene group.

[0068] Optionally, L and L2are the same or different, and each is independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group or a substituted or unsubstituted biphenylene group.

[0069] Optionally, L1is selected from a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted anthrylene, substituted or unsubstituted phenanthrylene, substituted or unsubstituted carbazolylene, substituted or unsubstituted diphenylfuranylene, or substituted or unsubstituted diphneylthienylene.

[0070] Optionally, the substituents in L, L1and L2are the same or different, each independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, i-propyl, t-butyl, phenyl or penta-deuterated phenyl.

[0071] In some embodiments of the present application, L and L2are the same or different, each independently selected from a single bond or a group consisting of:

[0072] In particular, L and L2are the same or different, each independently selected from a single bond or a group consisting of:

[0073] In some embodiments of the present application, L1is selected from a single bond or a group consisting of:

[0074] In particular, L1is selected from a single bond or a group consisting of:

[0075] In some embodiments of the present application, Ar1is selected from substituted or unsubstituted aryl having 6 to 26 carbon atoms or substituted or unsubstituted heteroaryl having 12 to 18 carbon atoms.

[0076] Optionally, the substituents in Ar1are the same or different, each independently selected from deuterium, halogen group, cyano, alkyl having 1 to 5 carbon atoms, aryl having 6 to 12 carbon atoms or deuterated aryl having 6 to 12 carbon atoms.

[0077] In some embodiments of the present application, Ar1is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted anthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted triphenylylene, substituted or unsubstituted diphenylfuranylene, substituted or unsubstituted diphneylthienylene, substituted or unsubstituted carbazolylene or substituted or unsubstituted spirobifluorenyl.

[0078] Optionally, the substituents in Ar1are the same or different, each independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, i-propyl, t-butyl, phenyl, naphthyl or penta-deuterated phenyl.

[0079] In some embodiments of the application, Ar1is selected from the group consisting of:

[0080] In particular, Ar1is selected from the group consisting of:

[0081] In some embodiments of the application, each R1and each R2are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, i-propyl, t-butyl, phenyl, naphthyl, or penta-deuterated phenyl.

[0082] In some embodiments of the application, Ar2is selected from the group consisting of:

[0083] In particular, Ar2is selected from the group consisting of:

[0084] In some embodiments of the application, is selected from the group consisting of:

[0085] In particular, is selected from the group consisting of:

[0086] In some embodiments of the application, is selected from the group consisting of:

[0087] In particular, is selected from the group consisting of:

[0088] In some embodiments of the application, in Formula 1 is selected from the group consisting of:

[0089] In particular, in Formula 1 is selected from the group consisting of:

[0090] In some embodiments of the application, the organic compound is selected from the group consisting of:

[0091] In a second aspect, the present application provides an organic electroluminescent device, comprising an anode and a cathode oppositely arranged, and a functional layer arranged between the anode and the cathode; the functional layer comprises the organic compound disclosed in the first aspect of the present application.

[0092] In an embodiment of the present application, the organic electroluminescent device is a phosphorescent device.

[0093] In a specific embodiment of the present application, the organic electroluminescent device is a red phosphorescent organic electroluminescent device.

[0094] In an embodiment of the present application, the functional layer comprises an organic light-emitting layer, and the organic light-emitting layer comprises the organic compound disclosed in the first aspect of the present application.

[0095] Optionally, the functional layer further comprises a hole injection layer, a hole transport layer, a light-emitting adjustment layer, an electron transport layer and an electron injection layer.

[0096] In some embodiments of the present application, the organic electroluminescent device comprises, in sequence, an anode (ITO substrate), a hole transport layer, a light-emitting adjustment layer, an organic light-emitting layer, an electron transport layer, an electron injection layer, a cathode (Mg-Ag mixture) and an organic capping layer.

[0097] In a specific embodiment of the present application, as shown in FIG. 1, the organic electroluminescent device of the present application comprises an anode 100, a cathode 200, and at least one functional layer 300 arranged between the anode layer and the cathode layer, wherein the functional layer 300 comprises a hole injection layer 310, a hole transport layer 320, a light-emitting adjustment layer 330, an organic light-emitting layer 340, an electron transport layer 350 and an electron injection layer 360.

[0098] Optionally, the anode 100 comprises 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. In some embodiments of the present application, the anode is a transparent electrode comprising indium tin oxide (ITO).

[0099] Optionally, the hole transport layer 320 can comprise one or more hole transport materials, which can be selected from carbazole polymers, carbazole-linked triarylamine compounds, or other types of compounds, without being particularly limited in the present application. For example, in some embodiments of the present application, the hole transport layer 320 consists of compound HT-1.

[0100] Optionally, the light-emitting adjustment layer 330 (also referred to as a hole adjustment layer, an electron blocking layer, a hole auxiliary layer, a hole buffer layer, a light-emitting auxiliary layer, or a second hole transport layer) can comprise one or more hole transport materials, which can be selected from carbazole polymers, carbazole-linked triarylamine compounds, or other types of compounds, without being particularly limited in the present application. For example, in some embodiments of the present application, the light-emitting adjustment layer 330 consists of compound HT-2.

[0101] Optionally, the organic light-emitting layer 340 can consist of a single light-emitting material, or can comprise a host material and a guest material. Optionally, the organic light-emitting layer 340 consists of a host material and a guest material, and holes and electrons injected into the organic light-emitting layer 340 can recombine in the organic light-emitting layer 340 to form excitons, which transfer energy to the host material, the host material transfers energy to the guest material, and the guest material is capable of emitting light.

[0102] The guest material of the organic light-emitting layer 340 can be a compound or derivative thereof having a condensed aryl ring, a compound or derivative thereof having a heteroaryl ring, an aromatic amine derivative, or other materials, without being particularly limited in the present application.

[0103] In some embodiments of the present application, the organic electroluminescent device is a red organic electroluminescent device, and the organic electroluminescent device comprises an organic light-emitting layer, and the organic light-emitting layer comprises the organic compound of the present application, compound RH-P, and guest material RD-01.

[0104] 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 selected from benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials, without special limitation. For example, in some embodiments of the present application, the electron transport layer 350 can be composed of compound ET-1 and LiQ.

[0105] Optionally, the cathode 200 includes a cathode material that is a material with a small work function that facilitates electron injection into the functional layer. Specific examples of the cathode material include a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or an alloy thereof; or a multi-layer material such as LiF / Al, Liq / Al, LiO2 / Al, LiF / Ca, LiF / Al, and BaF2 / Ca, but are not limited thereto. Preferably, a metal electrode including silver and magnesium is included as the cathode.

[0106] Optionally, an organic capping layer is further provided on the cathode 200.

[0107] Optionally, a hole injection layer 310 can be further provided between the anode 100 and the hole transport layer 320 to enhance the ability to inject holes into the hole transport layer 320. The hole injection layer 310 can be selected from a benzidine derivative, a starburst arylamine compound, a phthalocyanine derivative, or other materials, without special limitation. In some embodiments of the present application, the hole injection layer 310 can be composed of compound PD-1 and compound HT-1.

[0108] Optionally, an electron injection layer 360 can be further provided between the cathode 200 and the electron transport layer 350 to enhance the ability to inject electrons into the electron transport layer 350. The electron injection layer 360 can include an inorganic material such as an alkali metal sulfide, an alkali metal halide, or the like, or can include a complex of an alkali metal and an organic material. In some embodiments of the present application, the electron injection layer 360 can include ytterbium (Yb).

[0109] The third aspect of the present application also provides an electronic device including the organic electroluminescent device of the second aspect of the present application.

[0110] For example, as shown in FIG. 2, the electronic device provided by the present application is an electronic device 400 comprising any one of the organic electroluminescent devices described in the above embodiments of the organic electroluminescent device. The electronic device can be a display device, a lighting device, an optical communication device, or other types of electronic devices, for example, can include but is not limited to computer screens, mobile phone screens, televisions, electronic paper, emergency lighting, optical modules, etc. Since the electronic device 400 has the above-mentioned organic electroluminescent device, it has the same beneficial effects, and the present application will not be described here.

[0111] The present application will be described in detail below with reference to examples, but the following description is used to explain the present application, and is not in any way limiting the scope of the present application.

[0112] Synthetic Examples

[0113] It should be appreciated by those skilled in the art that the chemical reactions described in the present application can be used to suitably prepare many of the organic compounds of the present application, and other methods for preparing the compounds of the present application are considered to be within the scope of the present application. For example, the synthesis of those non-exemplified compounds according to the present application can be successfully performed by a person skilled in the art by modifying the methods, such as appropriately protecting interfering groups, by using other known reagents instead of those described in the present application, or by making some routine modifications of the reaction conditions. The compounds in the present application for which the synthetic methods are not mentioned are all raw material products obtained by commercial means.

[0114] Synthesis of Intermediate a-1

[0115] Under nitrogen protection, 2-bromo-6-chlorodibenzofuran (50.00 g, 177.62 mmol) and dry tetrahydrofuran (400 mL) were added to a flask, cooled to minus 80°C, and a solution of n-butyllithium in tetrahydrofuran (2.0 M) (106 mL, 213.12 mmol) was added dropwise under stirring. After the dropwise addition was completed, the mixture was stirred for 1 hour, and trimethyl borate (24.00 g, 230.88 mmol) was added dropwise while maintaining the temperature at minus 80°C. After the dropwise addition was completed, the mixture was maintained at room temperature for 1 hour, and stirred for 24 hours. A dilute hydrochloric acid (2 M, 120 mL) solution was added to the reaction liquid, and stirred for 1 hour. The organic phase was washed with water until neutral, dried by adding anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain a crude product. The crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane system to obtain a white solid a-1 (35.00 g, yield: 80%).

[0116] Referring to the synthesis method of intermediate a-1, the intermediates a-2 to a-4 shown in Table 1 were synthesized by using the reactant A in Table 1 instead of 2-bromo-6-chlorodibenzofuran.

[0117] Table 1

[0118] Synthesis of intermediate b-1

[0119] Into a 500 mL three-necked flask, intermediate a-1 (30.00 g, 121.73 mmol), 1-bromo-2-naphthaldehyde (28.50 g, 121.73 mmol), tetrakis(triphenylphosphine)palladium (Pd(PPh3)4, 1.41 g, 1.22 mmol), anhydrous potassium carbonate (37.01 g, 267.80 mmol), tetrabutylammonium bromide (7.84 g, 24.34 mmol), toluene (240 mL), ethanol (120 mL) and deionized water (60 mL) were added successively under nitrogen protection. The reaction was heated to reflux with stirring. After 10 h, the reaction system was cooled to room temperature. The product was extracted with dichloromethane (100 mL x 3 times). The organic phase was combined and dried over anhydrous magnesium sulfate. After filtration, the solvent was removed by distillation under reduced pressure to obtain a crude product. The crude product was purified by silica gel column chromatography with n-heptane as the mobile phase to obtain white solid b-1 (32.60 g, yield: 75%).

[0120] Referring to the synthesis method of intermediate b-1, the intermediates b-2 to b-4 shown in Table 2 were synthesized by replacing intermediate a-1 with the reactant B in Table 2.

[0121] Table 2

[0122] Synthesis of intermediate c-1

[0123] Into a 1 L three-necked flask, (methoxymethyl)triphenylphosphonium chloride (37.47 g, 109.31 mmol) and dry tetrahydrofuran (380 mL) were added. The reaction system was cooled to -15 °C. Potassium tert-butoxide (14.15 g, 126.12 mmol) was quickly added. The reaction solution turned red quickly and remained red during the whole process. After 1 h, intermediate b-1 (30.00 g, 84.08 mmol) was completely dissolved in THF (300 mL) and added dropwise into the flask at -15 °C. After the dropwise addition, the temperature was allowed to rise to room temperature naturally. After 1 h, the reaction was quenched by adding a large amount of water. The product was extracted with dichloromethane (100 mL x 3 times). The organic phase was combined and dried over anhydrous magnesium sulfate. After filtration, the solvent was removed by distillation under reduced pressure to obtain a crude product. The crude product was purified by silica gel column chromatography with dichloromethane / n-heptane as the mobile phase to obtain intermediate c-1 (25.80 g, yield: 80%).

[0124] The intermediates c-2 to c-4 shown in Table 3 were synthesized according to the synthetic method of intermediate c-1 by using the reactant C in Table 3 instead of intermediate b-1.

[0125] Table 3

[0126] Synthesis of intermediate d-1

[0127] Under nitrogen protection, into a 500 mL three-necked flask were added intermediate c-1 (25.00 g, 64.95 mmol), p-toluenesulfonic acid (1.12 g, 6.49 mmol), ethylene glycol (20.16 g, 324.81 mmol) and toluene (200 mL) successively, and then stirring and heating were started, and the temperature was raised to reflux, and the reaction was allowed to proceed for 2 h. After the system was cooled to room temperature, extraction was performed with dichloromethane (100 mL x 3 times), the organic phases were combined and dried over anhydrous magnesium sulfate, filtration was performed, and then the solvent was removed by distillation under reduced pressure to obtain a crude product. Purification was performed by silica gel column chromatography of the crude product with dichloromethane / n-heptane as the mobile phase to obtain intermediate d-1 (22.90 g, yield: 85%).

[0128] The intermediates d-2 to d-4 shown in Table 4 were synthesized according to the synthetic method of intermediate d-1 by using the reactant D in Table 4 instead of intermediate c-1.

[0129] Table 4

[0130] Synthesis of intermediate e-1

[0131] Under nitrogen protection, into a 500 mL three-necked flask were added intermediate d-1 (20.00 g, 48.20 mmol) and tetrahydrofuran (160 mL), and then the solution was cooled to -10 °C, and trifluoromethanesulfonic acid (20 mL) was added dropwise, and the reaction was allowed to proceed for 1 h, and then the temperature was allowed to rise to room temperature, and stirring was performed for 1 h. The reaction was quenched by adding water, extraction was performed with dichloromethane (100 mL x 3 times), the organic phases were combined and dried over anhydrous magnesium sulfate, filtration was performed, and then the solvent was removed by distillation under reduced pressure to obtain a crude product. Purification was performed by silica gel column chromatography of the crude product with dichloromethane / n-heptane as the mobile phase to obtain white solid e-1 (6.80 g, yield: 40%).

[0132] The intermediates e-2 to e-4 shown in Table 5 were synthesized according to the synthetic method of intermediate e-1 by using the reactant E in Table 5 instead of intermediate d-1.

[0133] Table 5

[0134] Synthesis of intermediate f-1

[0135] Into a 500 mL three-necked flask, was added intermediate e-1 (6.80 g, 19.30 mmol), bis(pinacolato)diboron (5.87 g, 23.12 mmol), potassium acetate (3.78 g, 38.50 mmol) and 1,4-dioxane (70 mL) under nitrogen protection. The stirring and heating were started, and the system was heated to 40 °C. Then tris(dibenzylideneacetone)dipalladium (Pd2(dba)3, 0.17 g, 0.19 mmol) and 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (XPhos, 0.18 g, 0.38 mmol) were added quickly. The system was heated to reflux, and the reaction was stirred overnight. After the system was cooled to room temperature, 200 mL of water was added, and the mixture was stirred for 30 min. The mixture was filtered under reduced pressure. The filter cake was washed with deionized water until neutral, and then washed with 100 mL of anhydrous ethanol. The crude product was obtained. The crude product was washed with n-heptane once, and then dissolved in 200 mL of toluene. The catalyst was removed by passing through a silica gel column. After concentration, white solid f-1 (6.80 g, yield: 80%) was obtained.

[0136] Referring to the synthesis method of intermediate f-1, the intermediates f-2 to f-4 shown in Table 6 were synthesized by using reactant F in Table 6 instead of intermediate e-1.

[0137] Table 6

[0138] Synthesis of intermediate g-1

[0139] Into a 500 mL three-necked flask, was added intermediate f-3 (6.80 g, 15.30 mmol), 4-bromochlorobenzene (2.93 g, 15.30 mmol), tetrakis(triphenylphosphine)palladium (Pd(PPh3)4, 0.17 g, 0.15 mmol), anhydrous potassium carbonate (4.65 g, 33.66 mmol), tetrabutylammonium bromide (0.99 g, 3.06 mmol), toluene (70 mL), ethanol (35 mL) and deionized water (17 mL) under nitrogen protection. The stirring and heating were started, and the system was heated to reflux. The reaction was stirred for 10 h. After the system was cooled to room temperature, the mixture was extracted with dichloromethane (100 mL x 3 times). The organic phases were combined and dried with anhydrous magnesium sulfate. After filtration, the solvent was removed by distillation under reduced pressure. The crude product was obtained. The crude product was purified by silica gel column chromatography using n-heptane as the mobile phase. White solid g-1 (4.92 g, yield: 75%) was obtained.

[0140] Referring to the synthesis method of intermediate g-1, the intermediates g-2 to g-11 shown in Table 7 were synthesized by using reactant G in Table 7 instead of intermediate f-3, and reactant H instead of 4-bromochlorobenzene.

[0141] Table 7

[0142] Synthesis of intermediate h-1

[0143] Into a 500 mL three-necked flask, intermediate g-1 (4.90 g, 11.42 mmol), bis(pinacolato)diboron (3.50 g, 13.78 mmol), potassium acetate (2.24 g, 22.82 mmol) and 1,4-dioxane (50 mL) were sequentially added under nitrogen protection. After the flask was stirred and heated, the system was warmed to 40 °C, and then tris(dibenzylideneacetone)dipalladium (Pd2(dba)3, 0.10 g, 0.11 mmol) and 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (XPhos, 0.11 g, 0.23 mmol) were quickly added. The system was continuously warmed to reflux, and the reaction was stirred overnight. After the system was cooled to room temperature, 200 mL of water was added to the system, which was stirred thoroughly for 30 min. The filter cake was washed with deionized water until it was neutral, and then washed with 100 mL of anhydrous ethanol. The crude product was obtained as a white solid (4.80 g, yield: 81%).

[0144] Referring to the synthesis method of intermediate f-1, the intermediates h-2 to h-11 shown in Table 8 were synthesized by using the reactant J in Table 8 instead of intermediate g-1.

[0145] Table 8

[0146] Synthesis of intermediate j-1

[0147] Into a flask, 2,4-dichloro-6-(dibenzofuran-4-yl)-1,3,5-triazine (20.00 g, 63.27 mmol), 4-(naphthalen-2-yl)benzeneboronic acid (10.50 g, 42.32 mmol), tetrakis(triphenylphosphine)palladium (0.49 g, 0.42 mmol), and potassium carbonate (12.80 g, 92.62 mmol) were added under nitrogen protection, and a mixed solvent of toluene (160 mL) and water (80 mL) was added. The system was warmed to 60 °C, and stirred for 24 hours. After the system was cooled to room temperature, the stirring was stopped, and the organic phase was separated after the reaction solution was washed with water. The organic phase was dried with anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain a crude product. The crude product was purified by silica gel column chromatography using n-heptane as the mobile phase to obtain white solid j-1 (12.20 g, yield: 60%).

[0148] Synthesis of compound 1

[0149] Into a 500 mL three-necked flask, under nitrogen protection, were added successively intermediate f-1 (5.00 g, 11.25 mmol), 2-chloro-4-(dibenzo[B,D]furan-3-yl)-6-phenyl-1,3,5-triazine (4.03 g, 11.26 mmol), Pd(PPh3)4 (0.13 g, 0.11 mmol), anhydrous potassium carbonate (3.42 g, 24.75 mmol), tetrabutylammonium bromide (0.73 g, 2.25 mmol), toluene (50 mL), tetrahydrofuran (25 mL) and deionized water (13 mL), stirring and heating were started, and the temperature was raised to reflux, and the reaction was allowed to proceed for 10 h. After the system was cooled to room temperature, extraction was performed with dichloromethane (100 mL x 3 times), the combined organic phase was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by distillation under reduced pressure to obtain a crude product. Purification was performed by silica gel column chromatography using n-heptane as the mobile phase, and white solid compound 1 (5.20 g, yield: 73%) was obtained.

[0150] Referring to the synthesis method of compound 1, using reactant K in Table 9 instead of intermediate f-1, and reactant L instead of 2-chloro-4-(dibenzo[B,D]furan-3-yl)-6-phenyl-1,3,5-triazine, the compounds shown in Table 9 were synthesized.

[0151] Table 9

[0152] The mass spectrometry data of some of the compounds are shown in Table 10 below

[0153] Table 10

[0154] The nuclear magnetic resonance data of some of the compounds are shown in Table 11 below.

[0155] Table 11

[0156] Preparation of an organic electroluminescent device

[0157] Example 1: Preparation of a red organic electroluminescent device

[0158] First, an anode pre-treatment was performed by the following process: on an ITO / Ag / ITO substrate with thicknesses of 1500 nm / 10 nm / 1500 nm, respectively, surface treatment was performed using ultraviolet ozone and O2:N2 plasma to increase the work function of the anode, or organic solvent cleaning was performed on the ITO substrate surface to remove impurities and oil stains on the ITO substrate surface.

[0159] ​On the experimental substrate (anode), the compound PD-1: compound HT-1 was co-evaporated at a rate ratio of 2%:98% to form a hole injection layer (HIL) having a thickness of 100 A.

[0160] On the hole injection layer, the compound HT-1 was vacuum evaporated to form a hole transport layer having a thickness of 100 A.

[0161] On the hole transport layer, the compound HT-2 was vacuum evaporated to form a light emitting adjustment layer having a thickness of 100 A.

[0162] On the light emitting adjustment layer, the compound 1: RH-P: RD-01 was co-evaporated at a rate ratio of 49%:49%:2% to form an organic light emitting layer (EML) having a thickness of 100 A.

[0163] On the organic light emitting layer, the compound ET-1 and LiQ were co-evaporated at a rate ratio of 1:1 to form an electron transport layer (ETL) having a thickness of 100 A.

[0164] Yb was evaporated on the electron transport layer to form an electron injection layer (EIL) having a thickness of 100 A, and then magnesium (Mg) and silver (Ag) were co-evaporated on the electron injection layer at a rate ratio of 1:9 to form a cathode having a thickness of 100 A.

[0165] On the above cathode, the compound CP-1 was vacuum evaporated to form an organic cover layer having a thickness of 100 A, thereby completing the manufacture of a red organic electroluminescent device.

[0166] Examples 2 to 27

[0167] An organic electroluminescent device was manufactured using the same method as in Example 1, except that the compound of Table 12 below was used instead of the compound 1 of Example 1 in the manufacture of the organic light emitting layer.

[0168] Comparative Examples 1 to 3

[0169] An organic electroluminescent device was manufactured using the same method as in Example 1, except that the compound A, the compound B, and the compound C were used instead of the compound 1 of Example 1 in the manufacture of the organic light emitting layer, respectively.

[0170] In the manufacture of each of the examples and the comparative examples, the compounds used had the following structures:

[0171] ​​​​​​​​The red organic electroluminescent devices prepared in Examples 1-27 and Comparative Examples 1-3 were tested for performance, specifically the IVL performance of the devices was tested at 10 mA / cm 2 The T95 device lifetime was tested at 20 mA / cm 2 The test results are shown in Table 12.

[0172] Table 12

[0173] As shown in the above table, when the compound of the present application is used as the host material of the organic light-emitting layer of the organic electroluminescent device, the current efficiency is at least 18.2% higher and the T95 lifetime is at least 15.7% higher than Comparative Examples 1-3.

[0174] Compared with Comparative Examples 1 and 2, when the organic compound of the present application is used as the red electron-type host material, the prepared device has a significantly reduced driving voltage and improved current efficiency and lifetime. The reason is that the triazine of the compound of the present application is connected with the dibenzofuranyl or the dibenzothiophenyl, which makes the compound molecule more flat, is conducive to the packing of the molecule, and can enhance the intermolecular force and improve the electron mobility of the compound.

[0175] Compared with Comparative Example 3, when the organic compound of the present application is used as the red electron-type host material, the driving voltage of the prepared device can be significantly reduced and the current efficiency and lifetime can be improved. The reason is that the triazine of the compound of the present application is connected with the 1, 2, 3 or 4 position of the benzo[5,6]phenanthro[2,1-b]benzofuran, which can promote energy transfer and further improve the electron transport capability, thereby improving the luminous efficiency of the device.

[0176] The above describes some embodiments of the present application in detail in combination with the drawings, but the present application is not limited to the specific details of the above embodiments. Within the technical concept of the present application, various simple modifications can be made to the technical solutions of the present application, and these simple modifications all belong to the protection scope of the present application.

Claims

1. Organic compound, characterized in that, The organic compound has a structure as shown in Formula 1: wherein D represents deuterium; n and m are the number of D, n is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; m is selected from 0, 1, 2 or 3; L, L1and L2are the same or different, and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms; Ar1is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms; Ar2is a group represented by formula 2; Y is O or S; each R1and each R2are the same or different, and are each independently selected from deuterium, a halogen, a cyano group, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms; n1is the number of R1, and is selected from 0, 1, 2 or 3, and when n1is greater than 1, any two R1are the same or different; n2is the number of R2, and is selected from 0, 1, 2, 3 or 4, and when n2is greater than 1, any two R2are the same or different; the substituents in L, L1, L2and Ar1are the same or different, and are each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms.

2. The organic compound according to claim 1, characterized by L, L1and L2are the same or different, and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 15 carbon atoms, or a substituted or unsubstituted heteroarylene group having 12 to 18 carbon atoms; optionally, the substituents in L, L1and L2are the same or different, and are each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, a phenyl group or a penta-deuterated phenyl group.

3. The organic compound according to claim 1, characterized by L, L1and L2are the same or different, and are each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted carbazolylene group, a substituted or unsubstituted dibenzofuranylene group, or a substituted or unsubstituted dibenzothiophenylene group; optionally, the substituents in L, L1and L2are the same or different, and are each independently selected from deuterium, fluorine, a cyano group, a methyl group, an ethyl group, a n-propyl group, an i-propyl group, a t-butyl group, a phenyl group or a penta-deuterated phenyl group.

4. The organic compound according to claim 1, wherein Ar1is selected from a substituted or unsubstituted aryl group having 6 to 26 carbon atoms, or a substituted or unsubstituted heteroaryl group having 12 to 18 carbon atoms; optionally, the substituents in Ar1are the same or different, and are each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, an aryl group having 6 to 12 carbon atoms, or a deuterated aryl group having 6 to 12 carbon atoms.

5. The organic compound according to claim 1, wherein Ar1is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted anthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, or substituted or unsubstituted spirobifluorenyl; Optionally, the substituents in Ar1are the same or different, each independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, i-propyl, t-butyl, phenyl, naphthyl, or penta-deuterated phenyl.

6. The organic compound according to claim 1, wherein each R1and each R2are the same or different, each independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, i-propyl, t-butyl, phenyl, naphthyl, or penta-deuterated phenyl.

7. The organic compound according to claim 1, wherein Ar2is selected from the group consisting of: Optionally, Ar2is selected from the group consisting of:

8. The organic compound according to claim 1, wherein selected from the group consisting of:

9. The organic compound according to claim 1, wherein selected from the group consisting of:

10. The organic compound according to claim 1, characterized by in formula 1 is selected from the group consisting of:

11. The organic compound according to claim 1, characterized by The organic compound is selected from the group consisting of:

12. An organic electroluminescent device, characterized by comprising oppositely disposed anode and cathode, and a functional layer disposed between the anode and the cathode; the functional layer comprises the organic compound according to any one of claims 1 to 11; Optionally, the functional layer comprises an organic light-emitting layer, and the organic light-emitting layer comprises the organic compound according to any one of claims 1 to 11. Optionally, the functional layer further comprises a hole injection layer, a hole transport layer, an emission adjusting layer, an electron transport layer, and an electron injection layer.

13. An electronic device, characterized by comprising the organic electroluminescence device according to claim 12. comprising the organic electroluminescence device according to claim 12.

Citation Information

Patent Citations

  • Heterocyclic compound and organic light emitting diode comprising the same

    CN103804333A

  • Organic electroluminescent compound and organic electroluminescent device comprising same

    CN113402508A

  • Organic compound, organic electroluminescent device, and electronic device

    CN117466912A

  • Organic compound and organic electroluminescent device using same

    WO2024014866A1

  • Composition for organic optoelectronic diode, organic optoelectronic diode and display device

    WO2024014934A1