Organic compound, organic electroluminescent device, and electronic device

Abstract

The present application relates to the technical field of organic electroluminescent materials, and provides a compound, an organic electroluminescent device comprising the compound, and an electronic device. The structure of the compound of the present application comprises a parent nucleus structure of dibenzofurano-naphthalene with a specific fusion pattern, wherein the parent nucleus is connected to substituted triazinyl as an electron transport type host material. When the compound of the present application is used as an electron transport type host material, the carrier balance in a light-emitting layer can be improved, a carrier recombination region is widened, the exciton generation and utilization efficiency is improved, and the luminous efficiency and service life of a device is improved.

Description

Organic compounds, organic electroluminescent devices and electronic devices

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims priority to Chinese patent application No. CN202410174120.7 filed on February 7, 2024. The full text of the above-mentioned Chinese patent application is hereby cited as part of this application. Technical Field

[0003] The present application relates to the technical field of organic electroluminescent materials, and in particular to an organic compound and an organic electroluminescent device and an electronic device comprising the same. Background Art

[0004] In recent years, organic electroluminescent devices (OLEDs) have become a very popular emerging flat-panel display product both at home and abroad. This is because OLED displays have the characteristics of self-luminescence, wide viewing angle, short response time, high efficiency, and wide color gamut.

[0005] An organic electroluminescent device (OLED) typically includes an anode, a cathode, and an organic layer formed between the two electrodes. The organic layer may include a hole injection layer, a hole transport layer, a hole auxiliary layer, an electron blocking layer, a light-emitting layer (containing a host and a dopant material), a hole blocking layer, an electron transport layer, and an electron injection layer. When a voltage is applied to the organic electroluminescent device, holes and electrons are injected into the light-emitting layer by the anode and cathode, respectively. Then, in the light-emitting layer, the injected holes and electrons recombine to form excitons. The excitons are in an excited state and release energy outward, causing the light-emitting layer to emit light outward.

[0006] Currently, organic electroluminescent devices (OLEDs) still face performance issues such as excessively high driving voltages, low luminous efficiency, and short lifespans, which hinder their application. Therefore, further research is necessary to improve the performance of OLEDs. Summary of the Invention

[0007] In view of the above problems existing in the prior art, the purpose of this application is to provide an organic compound and an organic electroluminescent device and an electronic device comprising the same. The organic compound is used in the organic electroluminescent device to improve the performance of the device.

[0008] According to a first aspect of the present application, an organic compound is provided, which has a structure represented by the following formula 1:

[0009] wherein each R1 and each R2 are the same or different and are independently selected from hydrogen, deuterium, an alkyl group having 1 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 15 carbon atoms, or a deuterated aryl group having 6 to 15 carbon atoms;

[0010] m represents the number of R1, m is selected from 0, 1, 2, 3, 4 or 5;

[0011] n represents the number of R2, and n is selected from 0, 1, 2, 3, 4, 5 or 6;

[0012] L, L1 and L2 are 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;

[0013] Ar1 and Ar2 are the same or different and are each independently 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;

[0014] The substituents in L, L1, L2, Ar1 and Ar2 are the same or different and are 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, aryl group with 6 to 20 carbon atoms, deuterated aryl group with 6 to 20 carbon atoms, heteroaryl group with 3 to 20 carbon atoms or cycloalkyl group with 5 to 10 carbon atoms; optionally, any two adjacent substituents form a saturated or unsaturated 5-13 membered ring.

[0015] According to a second aspect of the present application, an organic electroluminescent device is provided, comprising an anode and a cathode arranged opposite to each other, and a functional layer arranged between the anode and the cathode; the functional layer comprises the above-mentioned organic compound.

[0016] According to a third aspect of the present application, an electronic device is provided, comprising the organic electroluminescent device according to the second aspect.

[0017] The present application compound is the compound formed by the parent nucleus structure including two (benzofuran) naphthalene and the triazine structure, which can be used as electron transmission type luminescent host material. On the one hand, the parent nucleus of two (benzofuran) naphthalene has a larger conjugated area, which helps to enhance the intermolecular stacking of the target compound, improves the carrier transport ability of the compound; the oxygen atom in two benzofurans has two pairs of lone pairs of electrons, can also enhance the interaction between the compound molecules to a certain extent, further improve the carrier mobility of the compound; on the other hand, two dibenzofuran rings in the parent nucleus adopt a special condensed mode, and the hydrogen atoms on the two benzene rings can make the ring plane produce a certain deflection, and then improve the compound film forming property. When the present application compound is used as the electron transmission type host material in the hybrid host material, it is possible to improve the carrier balance in the luminescent layer, widen the carrier recombination region, improve exciton generation and utilization efficiency, improve device luminous efficiency and lifespan. BRIEF DESCRIPTION OF THE DRAWINGS

[0018] The accompanying drawings are used to provide further understanding of the present application and constitute a part of the specification. Together with the following specific embodiments, they are used to explain the present application, but do not constitute a limitation to the present application.

[0019] FIG1 is a schematic structural diagram of an organic electroluminescent device according to an embodiment of the present application.

[0020] FIG2 is a schematic structural diagram of an electronic device according to an embodiment of the present application.

[0021] Reference numerals 100 , anode 200 , cathode 300 , functional layer 310 , hole injection layer 321 , first hole transport layer 322 , luminescence adjustment layer 320 , hole transport layer 330 , organic light emitting layer 340 , electron transport layer 350 , electron injection layer 400 , electronic device DETAILED DESCRIPTION

[0022] The exemplary embodiments will now be described more fully with reference to the accompanying drawings. However, the exemplary embodiments can be implemented in a variety of 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 concepts of the 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 provide a full understanding of the embodiments of the present application.

[0023] According to a first aspect of the present application, an organic compound is provided, which has a structure represented by the following formula 1:

[0024] wherein each R1 and each R2 are the same or different and are independently selected from hydrogen, deuterium, an alkyl group having 1 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 15 carbon atoms, or a deuterated aryl group having 6 to 15 carbon atoms;

[0025] m represents the number of R1, m is selected from 0, 1, 2, 3, 4 or 5;

[0026] n represents the number of R2, and n is selected from 0, 1, 2, 3, 4, 5 or 6;

[0027] L, L1 and L2 are 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;

[0028] Ar1 and Ar2 are the same or different and are each independently 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;

[0029] The substituents in L, L1, L2, Ar1 and Ar2 are the same or different and are 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, aryl group with 6 to 20 carbon atoms, deuterated aryl group with 6 to 20 carbon atoms, heteroaryl group with 3 to 20 carbon atoms or cycloalkyl group with 5 to 10 carbon atoms; optionally, any two adjacent substituents form a saturated or unsaturated 5-13 membered ring.

[0030] In the present application, a saturated or unsaturated 5- to 13-membered ring refers to a carbon ring or heterocyclic ring containing 5 to 13 ring atoms, such as, but not limited to, a cyclopentane ring, a cyclohexane ring, a benzene ring, a fluorene ring, a pyran ring, a tetrahydropyran ring, a piperidine ring, and a tetrahydropiperidine ring.

[0031] In this application, the terms "optionally" and "optionally" mean that the event or environment described subsequently may or may not occur. For example, "optionally, any two adjacent substituents form a saturated or unsaturated 5-13 membered ring" includes: the scenario where any two adjacent substituents form a ring, and the scenario where any two adjacent substituents exist independently and do not form a ring. "Any two adjacent" can include two substituents on the same atom, and can also include one substituent on each of two adjacent atoms; wherein, when there are two substituents on the same atom, the two substituents can form a saturated or unsaturated spiro ring with the atom to which they are connected; when there is one substituent on each of two adjacent atoms, the two substituents can be fused into a ring.

[0032] In this application, the descriptions “each independently is”, “each independently is” and “each independently is” are interchangeable and should be understood in a broad sense. They 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, Wherein, each q is independently 0, 1, 2 or 3, and each R" is independently selected from hydrogen, deuterium, fluorine, and chlorine. The meaning is: Formula Q-1 represents that there are q substituents R" on the benzene ring, and each R" can be the same or different, and the options of each R" do not affect each other; Formula Q-2 represents that there are q substituents R" on each benzene ring of biphenyl, and 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 of each R" do not affect each other.

[0033] In this application, the term "substituted or unsubstituted" means that the functional group described after the term may or may not have a substituent (hereinafter, for ease of description, the substituents are collectively referred to as Rc). For example, "substituted or unsubstituted aryl" means an aryl group having the substituent Rc or an unsubstituted aryl group. The substituent Rc can be, for example, deuterium, cyano, a halogen group, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, a triphenylsilyl group, an aryl group having 6 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, an aryloxy group having 6 to 20 carbon atoms, or an arylthio group having 6 to 20 carbon atoms. The number of substituents can be one or more.

[0034] In the present application, "plurality" refers to two or more, for example, 2, 3, 4, 5, 6, etc.

[0035] In the present application, the number of carbon atoms in a substituted or unsubstituted functional group refers to the number of all carbon atoms.

[0036] The hydrogen atoms in the structures of the compounds of the present application include various isotope atoms of the hydrogen element, such as hydrogen (H), deuterium (D) or tritium (T).

[0037] “D” in the structural formula of the compound of the present application represents deuteration.

[0038] In the present application, aryl refers to an optional functional group or substituent derived from an aromatic carbocyclic ring. Aryl can be a monocyclic aryl (such as phenyl) or a polycyclic aryl. In other words, aryl can be a monocyclic aryl, a condensed ring aryl, two or more monocyclic aryl groups connected by a carbon-carbon bond, a monocyclic aryl and a condensed ring aryl connected by a carbon-carbon bond, two or more condensed ring aryl groups connected by a carbon-carbon bond. That is, unless otherwise indicated, two or more aromatic groups connected by a carbon-carbon bond can also be considered as aryl of the present application. Wherein, condensed ring aryl can, for example, include bicyclic condensed aryl (such as naphthyl), tricyclic condensed aryl (such as phenanthrenyl, fluorenyl, anthracenyl) etc. Aryl does not contain heteroatoms such as B, N, O, S, P, Se and Si. Examples of aryl include, but are not limited to, phenyl, naphthyl, fluorenyl, spirobifluorenyl anthracenyl, phenanthrenyl, biphenyl, terphenyl, triphenylene Peryl, benzo[9,10]phenanthryl, pyrenyl, benzofluoranthenyl, Ji et al.

[0039] In the present application, the arylene group refers to a divalent or multivalent group formed by further losing one or more hydrogen atoms from an aryl group.

[0040] In this application, terphenyl includes

[0041] In the present application, the number of carbon atoms of the substituted or unsubstituted aryl (arylene) group can be 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29 or 30. In some embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group 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 25 carbon atoms, in other embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, and in other embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having 6 to 15 carbon atoms.

[0042] In the present application, the fluorenyl group may be substituted by one or more substituents. In the case where the fluorenyl group is substituted, the substituted fluorenyl group may be: etc., but not limited thereto.

[0043] In the present application, examples of aryl groups as substituents include, but are not limited to, phenyl, naphthyl, phenanthrenyl, biphenyl, fluorenyl, dimethylfluorenyl, and the like.

[0044] In the present application, a heteroaryl group refers to a monovalent aromatic ring or a derivative thereof containing 1, 2, 3, 4, 5 or 6 heteroatoms in the ring, wherein the heteroatoms may be one or more of B, O, N, P, Si, Se and S. A heteroaryl group may be a monocyclic heteroaryl group or a polycyclic heteroaryl group. In other words, a heteroaryl group may be a single aromatic ring system or multiple aromatic ring systems connected by carbon-carbon bonds, and any aromatic ring system may be an aromatic monocyclic ring or an aromatic condensed ring. For example, the heteroaryl group may include a thienyl group, a furyl 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 pyrimidyl group, a triazinyl group, an acridinyl group, a pyridazinyl group, a pyrazinyl group, a quinolyl group, a quinazolinyl group, a quinoxalinyl group, a phenoxazinyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyrazinyl group, a pyrazinopyrazinyl group, an isoquinolyl group, an indolyl group, a carbazolyl group, a benzoxazolyl group, a benzimidazolyl group, a benzothiazolyl group, a benzocarbazolyl group, a benzothienyl group, a dibenzothienyl group, a thienothiphenyl group, a benzofuranyl group, a phenanthrolinyl group, an isoxazolyl group, a thiadiazolyl group, a phenothiazinyl group, a silafluorenyl group, a dibenzofuranyl group, and an N-phenylcarbazolyl group, an N-pyridylcarbazolyl group, an N-methylcarbazolyl group, and the like, without being limited thereto.

[0045] In the present application, the heteroarylene group refers to a divalent or multivalent group formed by further losing one or more hydrogen atoms from a heteroaryl group.

[0046] In the present application, the number of carbon atoms in the substituted or unsubstituted heteroaryl group (heteroarylene 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 a total carbon number of 3 to 30, in other embodiments, the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group having a total carbon number of 12 to 18, and in other embodiments, the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group having a total carbon number of 5 to 12.

[0047] In the present application, examples of heteroaryl groups as substituents include, but are not limited to, pyridyl, carbazolyl, dibenzothiophenyl, dibenzofuranyl, benzoxazolyl, benzothiazolyl, and benzimidazolyl.

[0048] In the present application, the substituted heteroaryl group may be a heteroaryl group in which one or more hydrogen atoms are replaced by groups such as a deuterium atom, a halogen group, a cyano group, an aryl group, a heteroaryl group, a trialkylsilyl group, an alkyl group, a cycloalkyl group, a haloalkyl group, or the like.

[0049] In the present application, the alkyl group having 1 to 10 carbon atoms may include a straight-chain alkyl group having 1 to 10 carbon atoms and a branched-chain alkyl group having 3 to 10 carbon atoms. The number of carbon atoms in the alkyl group may be, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10. Specific examples of the alkyl group include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, and n-hexyl.

[0050] In the present application, the halogen group may be, for example, fluorine, chlorine, bromine, or iodine.

[0051] In the present application, specific examples of trialkylsilyl include, but are not limited to, trimethylsilyl, triethylsilyl, and the like.

[0052] In the present application, specific examples of the haloalkyl group include, but are not limited to, trifluoromethyl.

[0053] In the present application, the number of carbon atoms in the cycloalkyl group having 3 to 10 carbon atoms may be, for example, 3, 4, 5, 6, 7, 8, 9 or 10. Specific examples of the cycloalkyl group include, but are not limited to, cyclopentanyl, cyclohexanyl, and adamantyl.

[0054] In the present application, the number of carbon atoms in a deuterated alkyl group having 1 to 10 is, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10. Specific examples of the deuterated alkyl group include, but are not limited to, trideuterated methyl.

[0055] In the present application, the carbon number of the haloalkyl group having 1 to 10 is, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10. Specific examples of the haloalkyl group include, but are not limited to, trifluoromethyl.

[0056] In this application, Refers to the chemical bonds that connect to other groups.

[0057] In this application, no single bond extending from the ring system is involved in the positioning of the connecting bond. This means that one end of the link can be connected to any position in the ring system that the link passes through, and the other end is connected to the rest of the compound molecule. For example, as shown in the following formula (f), the naphthyl represented by formula (f) is connected to other positions of the molecule via two non-positional linkers that pass through the bicyclic ring. The meaning of this includes any possible connection method shown in formulas (f-1) to (f-10):

[0058] For example, as shown in the following formula (X'), the dibenzofuranyl group represented by formula (X') is connected to other positions of the molecule through a non-positional connecting bond extending from the middle of one benzene ring. The meaning represented by it includes any possible connection method shown in formulas (X'-1) to (X'-4):

[0059] A non-positional substituent herein refers to a substituent connected via a single bond extending from the center of the ring system, indicating that the substituent can be attached at any possible position within 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 via a non-positional bond, and its meaning includes any possible connection method shown in formulas (Y-1) to (Y-7):

[0060] In some embodiments, each R1 and R2 is the same or different and is independently selected from hydrogen, deuterium, fluorine, cyano, trimethylsilyl, trideuteromethyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, or pentadeuterophenyl.

[0061] In some embodiments, the organic compound of the present application is selected from the structures shown in the following formulas (1-1) to (1-5):

[0062] The position and direction of the two benzofurans fused on the central naphthalene ring in the parent nucleus of the compound of the present application affect the first triplet energy level of the compound. When the compound has the structure shown in formula (1-1) and formula (1-3), T1 is higher, and the energy transfer efficiency of the compound is slightly lower than that of the compounds shown in formula (1-2), formula (1-4) and (1-5).

[0063] In some embodiments, L, L1 and L2 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6, 7, 8, 9, 10, 11, 12, 13, 14 or 15 carbon atoms, and a substituted or unsubstituted heteroarylene group having 5, 6, 7, 8, 9, 10, 12, 13, 14, 15, 16, 17 or 18 carbon atoms.

[0064] In some embodiments, L, L1 and L2 are 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 5 to 18 carbon atoms.

[0065] In some embodiments, the substituents in L, L1 and L2 are the same or different and are each independently selected from deuterium, fluorine, cyano, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, a deuterated alkyl group having 1 to 4 carbon atoms, a trialkylsilyl group having 3 to 7 carbon atoms, a phenyl group or a deuterated phenyl group.

[0066] In some embodiments, L, L1 and L2 are 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 fluorenylene group, a substituted or unsubstituted phenanthrenylene group, a substituted or unsubstituted dibenzothienylene group, a substituted or unsubstituted dibenzofuranylene group or a substituted or unsubstituted carbazolylene group.

[0067] In some embodiments, the substituents in L, L1 and L2 are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, pentadeuterophenyl or phenyl.

[0068] In some embodiments, L1 and L2 are the same or different and are each independently selected from the group consisting of a single bond or the following groups:

[0069] In some embodiments, L is selected from the group consisting of a single bond or the following groups:

[0070] In the compound of the present application, when L is selected from a single bond, the distance between the electron transport group and the parent nucleus in the compound is closer, which is beneficial to the effective arrangement of the compound molecules in the functional film layer and further improves the T95 life of the device.

[0071] In some embodiments, L1 and L2 are the same or different and are each independently selected from the group consisting of a single bond or the following groups:

[0072] In some embodiments, L is selected from the group consisting of a single bond or the following groups:

[0073] In some embodiments, Ar1 and Ar2 are the same or different and are each independently selected from substituted or unsubstituted aryl having 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, 38, 39 or 40 carbon atoms and substituted or unsubstituted heteroaryl having 5, 6, 7, 8, 9, 10, 12, 13, 14, 15, 16, 17, 18, 19, 20 carbon atoms.

[0074] In some embodiments, Ar1 and Ar2 are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 25 carbon atoms and a substituted or unsubstituted heteroaryl group having 5 to 18 carbon atoms.

[0075] In some embodiments, the substituents in Ar1 and Ar2 are the same or different and are each independently selected from deuterium, a halogen group, a cyano group, a haloalkyl group having 1 to 4 carbon atoms, a deuterated alkyl group having 1 to 4 carbon atoms, an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an aryl group having 6 to 15 carbon atoms, a heteroaryl group having 5 to 12 carbon atoms, a trialkylsilyl group having 3 to 7 carbon atoms, or a deuterated aryl group having 6 to 15 carbon atoms. Optionally, any two adjacent substituents form a benzene ring or a fluorene ring.

[0076] In some embodiments, Ar1 and Ar2 are the same or different and are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, or substituted or unsubstituted pyridyl.

[0077] In some embodiments, the substituents in Ar1 and Ar2 are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, pentadeuterophenyl, phenyl or naphthyl; optionally, any two adjacent substituents form a benzene ring or a fluorene ring.

[0078] In some embodiments, Ar1 and Ar2 are the same or different and are each independently selected from the following groups:

[0079] In some embodiments, Ar1 and Ar2 are the same or different and are each independently selected from the following groups:

[0080] In some embodiments, The same or different, and each independently selected from the following groups:

[0081] In some embodiments, in Formula 2 Selected from the following groups:

[0082] In some embodiments, the organic compound of the present application is selected from the group consisting of the following compounds:

[0083] In a second aspect of the present application, an organic electroluminescent device is provided, comprising an anode, a cathode, and a functional layer disposed between the anode and the cathode; wherein the functional layer comprises the organic compound described in the first aspect of the present application.

[0084] The organic compound provided in the present application can be used to form at least one organic film layer in a functional layer to improve the luminous efficiency, lifespan and other characteristics of an organic electroluminescent device.

[0085] In some embodiments, the functional layer includes an organic light-emitting layer, and the organic light-emitting layer includes the organic compound. The organic light-emitting layer can be composed of the organic compound provided in this application, or can be composed of the organic compound provided in this application and other materials.

[0086] According to a specific embodiment, the organic electroluminescent device is shown in Figure 1. The organic electroluminescent device may include an anode 100, a hole injection layer 310, a first hole transport layer 321, a luminescence adjustment layer (also called a hole auxiliary layer or a second hole transport 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 in sequence.

[0087] In the present 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 their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO) and indium zinc oxide (IZO); combined 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 (indium tin oxide) (ITO).

[0088] In the present application, the hole transport layer or the hole adjustment layer may include one or more hole transport materials, respectively. The hole transport layer material may be selected from carbazole polymers, carbazole-linked triarylamine compounds, or other types of compounds, and may specifically be selected from the following compounds or any combination thereof:

[0089] In one embodiment, the first hole transport layer 321 is composed of HT-1.

[0090] In one embodiment, the luminescence adjustment layer 322 is composed of HT-2.

[0091] In some embodiments, a hole injection layer 310 is further provided between the anode 100 and the first hole transport layer 321 to enhance the ability to inject holes into the first hole transport layer 321. The hole injection layer 310 may be made of a benzidine derivative, a starburst arylamine compound, a phthalocyanine derivative, or other materials, and this application does not impose any particular limitation thereto. The material of the hole injection layer 310 may be selected from the following compounds or any combination thereof, for example:

[0092] In one embodiment of the present application, the hole injection layer 310 is composed of PD and HT-1.

[0093] In some embodiments, the organic light-emitting layer 330 may include the host material and the guest material. In some embodiments, the organic light-emitting layer 330 is composed of the host material and the guest material. Holes and electrons injected into the organic light-emitting layer 330 may 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.

[0094] The host material of the organic light-emitting layer 330 may include metal chelate compounds, bisphenylethylene derivatives, aromatic amine derivatives, dibenzofuran derivatives, or other types of materials. In some embodiments, the host material includes the organic compound of the present application.

[0095] The guest material of the organic light-emitting layer 330 can be a compound having a condensed aromatic ring or a derivative thereof, a compound having a heteroaromatic ring or a derivative thereof, an aromatic amine derivative or other materials, and this application does not impose any special restrictions on this. The guest material is also called a doping material or a dopant. According to the type of luminescence, it can be divided into fluorescent dopants and phosphorescent dopants. For example, specific examples of the phosphorescent dopant include, but are not limited to, [Ir(flq)2(acac)], (Ir(Mphq)3), (RD).

[0096] In one embodiment of the present 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 is composed of the organic compound described in the present application. The guest material may be, for example, RD.

[0097] In another embodiment, the main material of the organic light emitting layer 330 includes the organic compound of the present application and RH-P The guest material is, for example, RD.

[0098] In one embodiment of the present 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 includes the organic compound of the present application. The guest material is, for example, fac-Ir(ppy)3.

[0099] The electron transport layer 340 may 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 not limited to, BmPyPhB, LiQ, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, triazine derivatives, and other electron transport materials. This application does not impose any special restrictions on this. The materials of the electron transport layer 340 include LiQ and other electron transport materials. The other electron transport materials may be selected from, but not limited to, the following compounds:

[0100] (ET), (BmPyPhB)

[0101] In one embodiment of the present application, the electron transport layer 340 is composed of ET and LiQ.

[0102] In the present application, cathode 200 includes a cathode material, which is a material with a small work function that facilitates electron injection into the functional layer. 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. In some embodiments, the cathode is a metal electrode comprising magnesium and silver.

[0103] In some embodiments, an electron injection layer 350 is further provided 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 an inorganic material such as an alkali metal sulfide or an alkali metal halide, or may include a complex of an alkali metal and an organic material. In one embodiment of the present application, the electron injection layer 350 includes ytterbium (Yb).

[0104] The present application not only provides the organic electroluminescent device comprising the organic compound represented by Formula 1 for use in the organic light-emitting layer, but also provides an electronic device comprising the organic electroluminescent device of the present application.

[0105] According to one embodiment, as shown in FIG2 , the provided electronic device is an electronic device 400. The electronic device 400 may be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices, including but not limited to computer screens, mobile phone screens, televisions, electronic paper, emergency lighting, optical modules, and the like.

[0106] The synthesis method of the organic compound of the present application is described in detail below with reference to synthesis examples, but the present disclosure is not limited thereby.

[0107] Synthesis Example

[0108] Those skilled in the art will recognize that the chemical reactions described herein can be used to appropriately prepare many of the heterocyclic compounds described herein, and that other methods for preparing the compounds described herein are considered within the scope of this application. For example, the synthesis of compounds not exemplified herein can be successfully accomplished by one skilled in the art through modifications such as appropriate protection of interfering groups, the use of known reagents other than those described herein, or conventional modifications of reaction conditions. Compounds for which no synthetic method is described herein are commercially available raw materials.

[0109] Synthesis of Sub-a1:

[0110] Under nitrogen, RM-1 (11.25 g, 50 mmol), RM-2 (13.55 g, 55 mmol), tetrakistriphenylphosphine palladium (0.58 g, 0.5 mmol), anhydrous sodium carbonate (10.60 g, 100 mmol), TBAB (1.61 g, 5 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 temperature was raised to reflux for 8 h. After cooling to room temperature, the mixture was extracted with dichloromethane (100 mL x 3). The organic phases were combined, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by distillation under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as the mobile phase to obtain Sub-a1 (9.88 g, 57% yield) as a white solid.

[0111] Referring to the synthesis of Sub-a1, reactant A shown in Table 1 was used instead of RM-2 to synthesize Sub-a2 to Sub-a5.

[0112] Table 1: Synthesis of Sub-a2 and Sub-a5

[0113] Synthesis of Sub-b1:

[0114] Under a nitrogen atmosphere, to a 1000 mL three-necked flask, (methoxymethyl)triphenylphosphonium chloride (51.25 g, 149.5 mmol), potassium tert-butoxide (18.10 g, 161 mmol), and anhydrous tetrahydrofuran (225 mL) were added sequentially. The system was cooled to -15°C and maintained for 30 min. Sub-a1 (45.10 g, 130 mmol) was then weighed and dissolved in anhydrous tetrahydrofuran (225 mL). This solution was slowly added dropwise to the reaction system using a constant pressure dropping funnel. The temperature was maintained at -15°C during the addition. After the addition was complete, the reaction was stirred at -15°C for 1 h. The reaction system was then allowed to warm to room temperature and extracted with dichloromethane (3 times, 200 mL). The organic phases were combined, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by distillation 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 obtain a red solid Sub-b1 (38.0 g, yield 78%).

[0115] Referring to the preparation process of Sub-b1, reactant B shown in Table 2 was used instead of Sub-a1 to synthesize Sub-b2 to Sub-b5.

[0116] Table 2: Synthesis of Sub-b2 to Sub-b5

[0117] Synthesis of Sub-c1:

[0118] Under a nitrogen atmosphere, Sub-b1 (44.60 g, 119 mmol), Eaton's reagent (4.5 mL), and chlorobenzene (500 mL) were added sequentially to a 1000 mL three-necked flask. The temperature was raised to reflux and the reaction was stirred for 4 h. After the reaction system reached room temperature, the reaction solution was poured into 1000 mL of deionized water and neutralized with saturated sodium hydroxide solution. The mixture was then extracted with dichloromethane (250 mL x 3). The organic phases were 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 using dichloromethane / n-heptane as the mobile phase to obtain Sub-c1 (21.62 g, 53% yield) as a white solid.

[0119] Referring to the synthesis method of Sub-c1, reactant C shown in Table 3 was used instead of Sub-b1 to synthesize Sub-c2 to Sub-c5.

[0120] Table 3: Synthesis of Sub-c2 to Sub-c5

[0121] Synthesis of Sub-d1:

[0122] Under nitrogen atmosphere, Sub-c1 (17.14 g, 50 mmol), pinacol diboron (14.0 g, 55 mmol), potassium acetate (10.8 g, 110 mmol) and 1,4-dioxane (160 mL) were added to a 500 mL three-necked flask in sequence. Stirring and heating were started. When the system was heated to 40 ° C, tris(dibenzylideneacetone)dipalladium (Pd2(dba)3, 0.46 g, 0.50 mmol) and 2-dicyclohexylphosphine-2',4',6'triisopropylbiphenyl (XPhos, 0.48 g, 1.0 mmol) were quickly added. The temperature was continued to rise 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, and the mixture was stirred thoroughly for 30 min. The mixture was filtered under reduced pressure, and the filter cake was washed with deionized water until neutral, and then rinsed with 100 mL of anhydrous ethanol to obtain a gray solid. The crude product was slurried once with n-heptane, completely dissolved in 200 mL of toluene, and then passed through a silica gel column to remove the catalyst. After concentration, a white solid Sub-d1 (15.63 g, 72% yield) was obtained.

[0123] Referring to the synthesis of Sub-d1, reactant D shown in Table 4 was used instead of Sub-c1 to synthesize Sub-d2 to Sub-d5.

[0124] Table 4: Synthesis of Sub-d2 to Sub-d5

[0125] Synthesis of Sub-e1:

[0126] Under nitrogen, RM-3 (17.90 g, 50 mmol), 3-chlorophenylboronic acid (8.60 g, 55 mmol), tetrakis(triphenylphosphine)palladium (0.58 g, 0.5 mmol), anhydrous sodium carbonate (10.60 g, 100 mmol), toluene (180 mL), anhydrous ethanol (45 mL), and deionized water (45 mL) were added sequentially to a 500 mL three-necked flask. Stirring and heating were initiated, and the temperature was raised to reflux for 8 h. After cooling to room temperature, the mixture was extracted with dichloromethane (100 mL x 3). The organic phases were combined, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by distillation under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as the mobile phase to obtain Sub-e1 (16.27 g, 75% yield) as a white solid.

[0127] Referring to the synthesis method of Sub-e1, reactant E shown in Table 5 was used instead of RM-3, and reactant F was used instead of 3-chlorophenylboronic acid to synthesize Sub-e2 to Sub-e7.

[0128] Table 5: Synthesis of Sub-e2 to Sub-e7

[0129] Synthesis of compound 4:

[0130] Under nitrogen, to a 250 mL three-necked flask were added Sub-d1 (11.40 g, 26.25 mmol), RM-4 (8.60 g, 25 mmol), palladium acetate (42 mg, 0.25 mmol), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (XPhos, 0.24 g, 0.5 mmol), anhydrous potassium carbonate (6.9 g, 50 mmol), tetrabutylammonium bromide (0.8 g, 2.5 mmol), toluene (100 mL), tetrahydrofuran (25 mL), and deionized water (25 mL). Stirring and heating were initiated, and the temperature was raised to reflux for 16 h. After cooling the system to room temperature, the mixture was extracted with dichloromethane (100 mL × 3 times). The organic phases were combined, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by distillation under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as the mobile phase to obtain yellow-green solid compound 4 (12.0 g, yield 78%, m / z = 616.19 [M+H] + ).

[0131] Referring to the synthesis method of compound 4, reactant G shown in Table 6 was used instead of Sub-d1, and reactant H was used instead of RM-4 to synthesize the organic compounds of the present application in Table 6.

[0132] Table 6: Synthesis of compounds of the present application

[0133] Compound 216 NMR: 1 H-NMR (400MHz, CD2Cl2) δppm: 8.82 (d, 2H), 8.66 (s, 1H), 8.33-8.25 (m, 3H), 8.18 (d, 2H), 7.94-7.81 (m, 7H), 7.77 (d, 1H), 7.68-7.38 (m, 11H).

[0134] Preparation and evaluation of organic electroluminescent devices:

[0135] Example 1: Preparation of red organic electroluminescent device

[0136] First, the anode pretreatment is carried out through the following process: On the ITO / Ag / ITO substrate, the surface treatment was performed using ultraviolet ozone and O2:N2 plasma to increase the work function of the anode, and the surface of the ITO substrate was cleaned with an organic solvent to remove impurities and oil stains on the surface of the ITO substrate.

[0137] PD:HT-1 was co-evaporated on the experimental substrate (anode) at an evaporation rate ratio of 2%:98% to form a film with a thickness of The hole injection layer (HIL) is then vacuum-deposited with HT-1 to form The first hole transport layer.

[0138] Compound HT-2 is vacuum evaporated on the first hole transport layer to form a layer with a thickness of Glow adjustment layer.

[0139] Next, compound 4: RH-P: RD were co-evaporated at a ratio of 49%: 49%: 2% on the luminescence adjustment layer to form a film with a thickness of red light emitting layer (EML).

[0140] On the red light emitting layer, compound ET and LiQ are co-evaporated at a 1:1 evaporation rate ratio to form Yb is evaporated on the electron transport layer to form a layer with a thickness of Then magnesium (Mg) and silver (Ag) were co-evaporated on the electron injection layer at an evaporation rate of 1:9 to form an electron injection layer with a thickness of cathode.

[0141] In addition, the thickness of the vacuum evaporation layer on the cathode is CP, thereby completing the manufacture of red organic electroluminescent devices.

[0142] Examples 2 to 75

[0143] An organic electroluminescent device was prepared by the same method as in Example 1, except that Compound X in Table 7 below was used instead of Compound 4 in Example 1 when preparing the red light emitting layer.

[0144] Comparative Examples 1 to 3

[0145] An organic electroluminescent device was prepared by the same method as in Example 1, except that Compound A, Compound B and Compound C in Table 7 were used instead of Compound 4 in Example 1 when preparing the red light emitting layer.

[0146] When preparing each embodiment and comparative example, the compound structure used is as follows:

[0147] The performance of the red organic electroluminescent devices prepared in Examples 1 to 75 and Comparative Examples 1 to 3 was tested. Specifically, at 10 mA / cm 2 The IVL performance of the device was tested under the conditions of T95 device life at 20mA / cm 2 The test was carried out under the conditions of , and the test results are shown in Table 7.

[0148] Table 7

[0149] As shown in Table 7 above, compared with Comparative Examples 1-3 using Compounds A-C, when the compounds of the present invention are used as host materials for red organic electroluminescent devices, the operating voltage of the devices decreases, the luminous efficiency (Cd / A) increases by at least 12.2%, and the T95 lifespan increases by at least 15.2%.

[0150] The main reason for this is that the special fusion mode of di(benzofuran)naphthalene in the organic compound provided in this application ensures that the parent nucleus has a more suitable first excited triplet energy level. The hydrogen atoms on the two benzene rings in the parent nucleus can cause a certain deflection of the ring plane, thereby improving the film-forming property of the compound, making it suitable as a luminescent host material.

Claims

1. An organic compound having a structure as shown in Formula 1: in, each R1 and each R2 are the same or different and are independently selected from hydrogen, deuterium, an alkyl group having 1 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 15 carbon atoms, or a deuterated aryl group having 6 to 15 carbon atoms; m represents the number of R1, m is selected from 0, 1, 2, 3, 4 or 5; n represents the number of R2, and n is selected from 0, 1, 2, 3, 4, 5 or 6; L, L1 and L2 are 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; Ar1 and Ar2 are the same or different and are each independently 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; The substituents in L, L1, L2, Ar1 and Ar2 are the same or different and are 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, aryl group with 6 to 20 carbon atoms, deuterated aryl group with 6 to 20 carbon atoms, heteroaryl group with 3 to 20 carbon atoms or cycloalkyl group with 5 to 10 carbon atoms; optionally, any two adjacent substituents form a saturated or unsaturated 5-13 membered ring.

2. The organic compound according to claim 1, wherein L, L1 and L2 are 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 fluorenylene group, a substituted or unsubstituted phenanthrenylene group, a substituted or unsubstituted dibenzothienylene group, a substituted or unsubstituted dibenzofuranylene group or a substituted or unsubstituted carbazolylene group; Optionally, the substituents in L, L1 and L2 are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, pentadeuterophenyl or phenyl.

3. The organic compound according to claim 1 or 2, wherein L1 and L2 are the same or different and are each independently selected from the group consisting of a single bond or the following groups: Optionally, L is selected from the group consisting of a single bond or the following groups:

4. The organic compound according to any one of claims 1 to 3, wherein Ar1 and Ar2 are the same or different and are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, and substituted or unsubstituted pyridyl; Optionally, the substituents in Ar1 and Ar2 are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, pentadeuterophenyl, phenyl or naphthyl; optionally, any two adjacent substituents form a benzene ring or a fluorene ring.

5. The organic compound according to any one of claims 1 to 4, wherein Ar1 and Ar2 are the same or different and are each independently selected from the following groups:

6. The organic compound according to any one of claims 1 to 5, wherein The same or different, and each independently selected from the following groups:

7. The organic compound according to any one of claims 1 to 6, wherein Each of R1 and R2 is the same or different and is independently selected from hydrogen, deuterium, fluorine, cyano, trimethylsilyl, trideuteromethyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, phenyl or pentadeuterophenyl.

8. The organic compound according to any one of claims 1 to 7, wherein In formula 2 Selected from the following groups:

9. The organic compound according to any one of claims 1 to 8, wherein The organic compound is selected from the group consisting of the following compounds:

10. 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; wherein: The functional layer comprises the organic compound according to any one of claims 1 to 9; Optionally, the functional layer includes an organic light-emitting layer, and the organic light-emitting layer includes the organic compound.

11. An electronic device comprising the organic electroluminescent device according to claim 10.

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