Organic compound, organic electroluminescent device comprising same, and electronic device

Abstract

The present application belongs to the technical field of organic electroluminescence. Provided are an organic compound, an organic electroluminescent device comprising same, and an electronic device. The organic compound has a structure as shown in formula I. An organic electroluminescent device prepared by using the compound as an organic light-emitting layer has good photoelectric performance.

Description

Organic compound and organic electroluminescent device and electronic device containing the same

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims priority to Chinese patent application No. CN202310789272.3 filed on June 29, 2023. The full text of the above-mentioned Chinese patent application is hereby cited as part of this application. Technical Field

[0003] The present invention relates to the field of organic electroluminescence, and in particular to an organic compound and an organic electroluminescent device and an electronic device containing the same. Background Art

[0004] Organic electroluminescent devices, such as organic light-emitting diodes (OLEDs), typically include a cathode and an anode positioned opposite each other, and a functional layer disposed between the cathode and the anode. The functional layer is composed of multiple organic or inorganic film layers and generally includes an organic light-emitting layer, a hole transport layer, an electron transport layer, and the like. When a voltage is applied between the cathode and the anode, an electric field is generated between the two electrodes. Under the action of the electric field, electrons on the cathode side move toward the electroluminescent layer, and holes on the anode side also move toward the light-emitting layer. The electrons and holes combine in the electroluminescent layer to form excitons, which are in an excited state and release energy outward, thereby causing the electroluminescent layer to emit light outward.

[0005] The main problems with existing organic electroluminescent devices are lifespan and efficiency. As displays become larger, the driving voltage also increases, and the luminous efficiency and current efficiency also need to be improved. Therefore, it is necessary to continue to develop new materials to further improve the performance of organic electroluminescent devices.

[0006] Summary of the Invention

[0007] The purpose of the present application is to provide an organic compound and an organic electroluminescent device and an electronic device containing the same. The organic compound can be used in an organic electroluminescent device to improve the performance of the device.

[0008] According to the first aspect of the present application, an organic compound is provided, wherein the organic compound has a structure shown in Formula I:

[0009] wherein each R is independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 12 carbon atoms;

[0010] n is the number of R, and n is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; when n is greater than 1, any two R are the same or different;

[0011] 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;

[0012] 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;

[0013] The substituents in Ar1, Ar2, L, L1 and L2 are the same or different and are independently selected from deuterium, a halogen group, a cyano 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 deuterated aryl group having 6 to 12 carbon atoms, an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 3 to 20 carbon atoms; optionally, any two adjacent substituents in Ar1 form a saturated or unsaturated 3-15 membered ring; optionally, any two adjacent substituents in Ar2 form a saturated or unsaturated 3-15 membered ring.

[0014] According to a second aspect of the present application, an organic electroluminescent device is provided, comprising an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer comprises the above-mentioned organic compound.

[0015] According to a third aspect of the present application, an electronic device is provided, comprising the organic electroluminescent device according to the second aspect.

[0016] The structure of the compound of the present application contains the parent core structure of phenanthro[3,2-b]benzofuran, which is connected to the electron-deficient heteroaryl of the triazine class as an electron-transmitting red light host material. On the one hand, the special fusion mode of phenanthro[3,2-b]benzofuran ensures that the parent core of phenanthro[3,2-b]benzofuran has a more suitable first excited triplet energy level, which is suitable as a fragment of the red light host material; on the other hand, the parent core structure of phenanthro[3,2-b]benzofuran has a larger conjugated system. After connecting it to the electron-deficient heteroaryl of the triazine class, it can enhance the intermolecular force and improve the electron mobility of the compound. When the compound of the present application is used as an electron-transmitting material in a mixed red light host material, it can improve the carrier balance in the light-emitting layer, broaden the carrier recombination area, improve the exciton generation and utilization efficiency, and improve the luminous efficiency and life of the device.

[0017] Other features and advantages of the present application will be described in detail in the subsequent detailed description. 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 , second 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] In a first aspect, the present application provides an organic compound having a structure shown in Formula I:

[0024] wherein each R is independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 12 carbon atoms;

[0025] n is the number of R, and n is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; when n is greater than 1, any two R are the same or different;

[0026] 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;

[0027] 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;

[0028] The substituents in Ar1, Ar2, L, L1 and L2 are the same or different and are independently selected from deuterium, a halogen group, a cyano 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 deuterated aryl group having 6 to 12 carbon atoms, an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 3 to 20 carbon atoms; optionally, any two adjacent substituents in Ar1 form a saturated or unsaturated 3-15 membered ring; optionally, any two adjacent substituents in Ar2 form a saturated or unsaturated 3-15 membered ring.

[0029] In this application, the terms "optional", "optionally" and "optionally" mean that the event or environment described subsequently may or may not occur. For example, "optionally, any two adjacent substituents in Ar1 form a saturated or unsaturated 3-15 membered ring" includes: the scenario where any two adjacent substituents in Ar1 form a ring, and the scenario where any two adjacent substituents in Ar1 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 commonly connected; when there is one substituent on each of two adjacent atoms, the two substituents can be fused into a ring.

[0030] 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.

[0031] 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" refers to an aryl group having a substituent Rc or an aryl group without a substituent. The above-mentioned substituent, i.e., Rc, can be, for example, deuterium, a halogen group, a cyano group, a heteroaryl group, an aryl group, a deuterated aryl group, a trialkylsilyl group, an alkyl group, a haloalkyl group, a deuterated alkyl group, etc. The number of substituents can be one or more.

[0032] In this application, "plurality" refers to two or more, for example, 2, 3, 4, 5, 6, etc.

[0033] In the present application, the number of carbon atoms in a substituted or unsubstituted functional group refers to the number of all carbon atoms.

[0034] 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).

[0035] “D” in the structural formula of the compound of the present application represents deuteration.

[0036] In the present application, " aryl " refers to the optional functional group or substituent derived from aromatic carbocyclic ring.Aryl can be monocyclic aryl (such as phenyl) or polycyclic aryl. In other words, aryl can be monocyclic aryl, condensed ring aryl, two or more monocyclic aryl connected by carbon-carbon bond, monocyclic aryl and condensed ring aryl connected by carbon-carbon bond, two or more condensed ring aryl connected by carbon-carbon bond. That is, unless otherwise indicated, two or more aromatic groups connected by carbon-carbon bond can also be regarded 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 groups include, but are not limited to, phenyl, naphthyl, fluorenyl, spirobifluorenyl, anthracenyl, phenanthrenyl, biphenyl, terphenyl, triphenylene, peryl, benzo[9,10]phenanthrenyl, pyrenyl, benzofluoranthenyl, Ji et al.

[0037] In the present application, "arylene group" refers to a divalent group formed by further losing one or more hydrogen atoms from an aryl group.

[0038] In this application, terphenyl includes

[0039] In the present application, the number of carbon atoms in the substituted or unsubstituted aryl (arylene) group can be 6, 8, 10, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 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 20 carbon atoms.

[0040] 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.

[0041] In the present application, examples of aryl groups as substituents for Ar1, Ar2, L, L1 and L2 include, but are not limited to, phenyl, naphthyl, phenanthrenyl, biphenyl, pentadeuterated phenyl and the like.

[0042] 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.

[0043] 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.

[0044] In the present application, the number of carbon atoms in the substituted or unsubstituted heteroaryl (heteroarylene) 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, 30.

[0045] In some embodiments, the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group having 5 to 25 carbon atoms in total.

[0046] In the present application, examples of heteroaryl groups as substituents for Ar1, Ar2, L, L1 and L2 include, but are not limited to, pyridyl, carbazolyl, dibenzothiophenyl, dibenzofuranyl, benzoxazolyl, benzothiazolyl and benzimidazolyl.

[0047] 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, -CN, an aryl group, a heteroaryl group, a deuterated aryl group, a trialkylsilyl group, an alkyl group, a deuterated alkyl group, a haloalkyl group, or the like.

[0048] 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.

[0049] In the present application, the halogen group may be, for example, fluorine, chlorine, bromine, or iodine.

[0050] In the present application, specific examples of trialkylsilyl include, but are not limited to, trimethylsilyl, triethylsilyl, and the like.

[0051] In the present application, the number of carbon atoms in a deuterated alkyl group having 1 to 10 carbon atoms is, for example, 1, 2, 3, 4, 5, 6, 7, 8 or 10. Specific examples of the deuterated alkyl group include, but are not limited to, trideuterated methyl.

[0052] 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 or 10. Specific examples of the haloalkyl group include, but are not limited to, trifluoromethyl.

[0053] In this application, a ring system formed by n atoms is referred to as an n-membered ring. For example, a phenyl group is a 6-membered ring. A saturated or unsaturated 3-15-membered ring refers to a saturated or unsaturated cyclic group having 3-15 ring atoms. Examples of saturated or unsaturated 3-15-membered rings include cyclopentane, cyclohexane, fluorene, and benzene rings.

[0054] In this application, Refers to the chemical bonds that connect to other groups.

[0055] 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).

[0056] For another example, as shown in the following formula (X'), the dibenzofuranyl group represented by formula (X') is connected to other positions in the molecule through a non-positional connecting bond extending from the middle of one side of the benzene ring, and the meaning represented by it includes any possible connection method shown in formulas (X'-1) to (X'-4).

[0057] A non-positional substituent as used 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 Formula (Y) below, 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).

[0058] In some embodiments of the present application, the organic compound is selected from the group consisting of the structures shown in Formulas I-1 to I-4:

[0059] Wherein, R, L, L1, L2, Ar1, Ar2, and n are defined the same as in Formula I.

[0060] In some embodiments, each R is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, or phenyl.

[0061] In the present application, L, L1, and L2 are the same or different and can be independently selected from the group consisting of a single bond, a substituted or unsubstituted arylene group 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, or 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, or 30 carbon atoms.

[0062] 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 18 carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 18 carbon atoms.

[0063] Optionally, 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, an aryl group having 6 to 12 carbon atoms or a deuterated aryl group having 6 to 12 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 phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted pyridylene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenylene group, or a substituted or unsubstituted carbazolylene group.

[0065] 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, trimethylsilyl, deuterated phenyl, phenyl or naphthyl.

[0066] In some embodiments, L, L1, and L2 are each independently selected from the group consisting of a single bond or the following groups:

[0067] In some embodiments, L is selected from the group consisting of a single bond or the following groups:

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

[0069] In some embodiments, L, L1, and L2 are each independently selected from the group consisting of a single bond or the following groups:

[0070] In the present application, Ar1 and Ar2 are the same or different and can be independently selected from: substituted or unsubstituted aryl groups having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, or 30 carbon atoms; and substituted or unsubstituted heteroaryl groups having 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, or 30 carbon atoms.

[0071] 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, or a substituted or unsubstituted heteroaryl group having 12 to 25 carbon atoms.

[0072] 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, or a substituted or unsubstituted heteroaryl group having 12 to 18 carbon atoms.

[0073] Optionally, the substituents in Ar1 and Ar2 are the same or different and are independently selected from deuterium, fluorine, cyano, alkyl having 1-5 carbon atoms, haloalkyl having 1-5 carbon atoms, deuterated alkyl having 1-5 carbon atoms, trialkylsilyl having 3-7 carbon atoms, deuterated aryl having 6-12 carbon atoms, aryl having 6-12 carbon atoms, heteroaryl having 5-12 carbon atoms; optionally, any two adjacent substituents in Ar1 form a benzene ring or a fluorene ring; optionally, any two adjacent substituents in Ar2 form a benzene ring or a fluorene ring.

[0074] 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 phenanthrenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, or substituted or unsubstituted carbazolyl.

[0075] 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, naphthyl, biphenyl, pyridyl, dibenzofuranyl, dibenzothiophenyl or carbazolyl.

[0076] In some embodiments, Ar1 and Ar2 are the same or different and are each independently selected from a substituted or unsubstituted group W, wherein the unsubstituted group W is selected from the following groups:

[0077] The substituted group W has one or more substituents, each of which is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, pentadeuterophenyl, phenyl, naphthyl, biphenyl, pyridyl, dibenzofuranyl, dibenzothiophenyl or carbazolyl; and when the number of substituents in the group W is greater than 1, each substituent is the same or different.

[0078] In some embodiments, Ar1 and Ar2 are each independently selected from the group consisting of:

[0079] In some embodiments, Ar1 and Ar2 are each independently selected from the group consisting of:

[0080] In some embodiments, Each is independently selected from the group consisting of:

[0081] Specifically, the organic compound can be selected from the group consisting of the following compounds:

[0082] In a second aspect, the present application provides an organic electroluminescent device 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.

[0083] In the present application, the organic electroluminescent device may be a blue light device, a red light device or a green light device, preferably a red light device.

[0084] According to one embodiment, the structure of the organic electroluminescent device is shown in FIG1 , including an anode 100 and a cathode 200 disposed opposite to each other, and a functional layer 300 disposed between the anode 100 and the cathode 200 ; the functional layer 300 comprises the organic compound provided in this application.

[0085] Optionally, the functional layer 300 includes an organic light-emitting layer 330 , wherein the organic light-emitting layer 330 includes the organic compound provided in this application.

[0086] The 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. The light-emitting layer can be one layer or two or more layers.

[0087] In one embodiment of the present application, an organic electroluminescent device may include an anode 100, a first hole transport layer 321, a second hole transport layer 322, an organic light-emitting layer 330 serving as an energy conversion layer, an electron transport layer 340, and a cathode 200, which are sequentially stacked. The organic compound provided herein can be applied to the organic light-emitting layer 330 of the organic electroluminescent device, effectively improving the luminous efficiency of the organic electroluminescent device and reducing the driving voltage of the organic electroluminescent device.

[0088] In the present application, the anode 100 includes an anode material, which is optionally 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. Optionally, a transparent electrode comprising indium tin oxide (ITO) as an anode is included.

[0089] Optionally, the first hole transport layer 321 and the second hole transport layer 322 each include one or more hole transport materials, and the hole transport material can be selected from carbazole polymers, carbazole-linked aromatic amine compounds, dibenzofuran-linked aromatic amine compounds, substituted fluorenyl-linked triarylamine compounds or other types of compounds, which are not specifically limited in this application. The first hole transport layer 321 can be made of compound HT-1 The second hole transport layer 322 can be composed of compound HT-2 composition.

[0090] Optionally, a hole injection layer 310 is further provided between the anode 100 and the hole transport layer 321 to enhance the ability to inject holes into the 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 is, for example, selected from the following compounds or any combination thereof:

[0091] In one embodiment of the present application, the hole injection layer 310 is composed of PD and HT-1.

[0092] Alternatively, the organic light-emitting layer 330 may be composed of a single light-emitting material, or may include a host material and a guest material. Alternatively, the organic light-emitting layer 330 may be composed of a host material and a 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.

[0093] The main material of the organic light emitting layer 330 can be a single compound or a combination of two or more compounds. In one embodiment of the present application, the main material of the organic light emitting layer 330 includes the organic compound provided in the present application and

[0094] The guest material of the organic light-emitting layer 330 can be a compound having a condensed aryl ring or its derivative, a compound having a heteroaryl ring or its derivative, an aromatic amine derivative, or other materials, which are not particularly limited in this application. The guest material is also called a dopant material or a dopant.

[0095] In some specific embodiments of the present application, the guest material of the organic light emitting layer 330 is RD

[0096] 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 material may be selected from, but not limited to, LiQ, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials, and this application does not impose any particular restrictions on this. The materials of the electron transport layer 340 include, but are not limited to, the following compounds:

[0097] In one embodiment of the present application, the electron transport layer 340 is composed of ET and LiQ.

[0098] In the present application, cathode 200 includes a cathode material having 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. Alternatively, a metal electrode containing magnesium and silver may be used as the cathode.

[0099] Optionally, 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 a lanthanide metal, an alkali metal sulfide, an alkali metal halide, or may include a complex of an alkali metal and an organic matter. In one embodiment of the present application, the electron injection layer 350 includes metal Yb.

[0100] A third aspect of the present application provides an electronic device comprising the organic electroluminescent device described in the second aspect of the present application.

[0101] According to one embodiment, as shown in FIG2 , an electronic device provided is electronic device 400, which includes the above-mentioned organic electroluminescent device. 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, etc.

[0102] The synthesis method of the organic compound of the present application is described in detail below with reference to synthesis examples, but the present application is not limited thereto.

[0103] Synthesis Example

[0104] Those skilled in the art will recognize that the chemical reactions described herein can be used to appropriately prepare many of the organic 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 not described herein are commercially available starting materials.

[0105] 1. Synthesis of intermediates

[0106] (1) Synthesis of Sub-a1 to Sub-a4:

[0107] Under a nitrogen atmosphere, 2-bromo-3-methoxyphenanthrene (14.34 g, 50 mmol), 4-chloro-2-fluorophenylboronic acid (9.58 g, 55 mmol), tetrakis(triphenylphosphine)palladium (0.58 g, 0.5 mmol), tetrabutylammonium bromide (TBAB, 1.61 g, 5 mmol), anhydrous sodium carbonate (10.60 g, 100 mmol), toluene (140 mL), anhydrous ethanol (35 mL), and deionized water (35 mL) were added sequentially to a 500 mL three-necked flask. Stirring and heating were initiated, and the temperature was raised to reflux and the reaction was allowed to proceed overnight. After the system cooled to room temperature, extraction with dichloromethane (100 mL × 3 times) was performed. 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 a white solid (12.1 g, 72% yield).

[0108] Referring to the synthesis of Sub-a1, Sub-a2 to Sub-a4 were synthesized by using reactant A shown in Table 1 instead of 4-chloro-2-fluorophenylboronic acid.

[0109] Table 1

[0110] (2) Synthesis of intermediates Sub-b1 to Sub-b2:

[0111] Under a nitrogen atmosphere, Sub-a1 (22.73 g, 67.5 mmol) and dry dichloromethane (220 mL) were added to a 500 mL three-necked flask. The system was cooled to 0±5°C and a dichloromethane solution of boron tribromide (135 mL, 1 M) was added dropwise using a constant pressure dropping funnel. The temperature was strictly controlled within the range of 0±5°C during the addition. After the addition was completed, the temperature was maintained at 0±5°C for 2 h, after which the system was allowed to warm to room temperature naturally and stirred overnight. The system was cooled again to -78°C and methanol (11 mL) was slowly added dropwise using a constant pressure dropping funnel to quench the reaction. After the system warmed to room temperature, the reaction solution was extracted with dichloromethane (100 mL × 3 times). The organic phase was dried over 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 / dichloromethane as the mobile phase to obtain the white solid product Sub-b1 (16.77 g, 77% yield).

[0112] Referring to the synthesis of Sub-b1, reactant B shown in Table 2 was used instead of Sub-a1 to synthesize Sub-b2 to Sub-b4.

[0113] Table 2

[0114] (3) Synthesis of intermediates Sub-c1 to Sub-c4:

[0115] Under a nitrogen atmosphere, Sub-b1 (16.14 g, 50 mmol), cesium carbonate (32.58 g, 100 mmol), and DMSO (160 mL) were added to a 250 mL three-necked flask. Stirring and heating were initiated, and the temperature was raised to 80°C for 4 h. After the system cooled to room temperature, extraction was performed with dichloromethane (100 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 n-heptane as the mobile phase to obtain Sub-c1 (13.47 g, 89% yield) as a white solid.

[0116] Referring to the synthesis of Sub-c1, reactant C shown in Table 3 was used instead of Sub-b1 to synthesize Sub-c2 to Sub-c4.

[0117] Table 3

[0118] (4) Synthesis of intermediates Sub-d1 to Sub-d4:

[0119] Under nitrogen atmosphere, Sub-c1 (15.1 g, 50 mmol), pinacol diboron (14.0 g, 55 mmol), potassium acetate (10.8 g, 110 mmol) and 1,4-dioxane (150 mL) were added in sequence to a 500 mL three-necked flask. 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 filter cake was filtered under reduced pressure to obtain a filter cake. The filter cake was dissolved in dichloromethane, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by distillation under reduced pressure to obtain a crude product. The crude product was slurried once with n-heptane to obtain Sub-d1 (14.4 g, 73% yield) as a white solid.

[0120] 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-d4.

[0121] Table 4

[0122] (5) Synthesis of intermediates Sub-e1 to Sub-e11:

[0123] Under a nitrogen atmosphere, RM-1 (18.44 g, 50 mmol), 3-chlorophenylboronic acid (8.60 g, 55 mmol), tetrakis(triphenylphosphine)palladium (Pd(PPh3)4, 0.58 g, 0.5 mmol), anhydrous sodium carbonate (10.60 g, 100 mmol), toluene (180 mL), tetrahydrofuran (45 mL), and deionized water (45 mL) were added sequentially to a 1000 mL three-necked flask. Stirring and heating were started, and the temperature was raised to reflux and the reaction was allowed to proceed overnight. After the system was cooled to room temperature, it was extracted with dichloromethane (100 mL × 3 times). The organic phases were combined and dried over anhydrous magnesium sulfate. After filtration, the solvent was distilled off 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 a white solid (19.80 g, yield 89%).

[0124] Referring to the synthesis of Sub-e1, Sub-e2 to Sub-e11 were synthesized by using reactant E shown in Table 5 instead of RM-1 and reactant F instead of 3-chlorophenylboronic acid.

[0125] Table 5

[0126] 2. Synthesis of compounds:

[0127] Synthesis of compound 4

[0128] Under a nitrogen atmosphere, Sub-d1 (10.84 g, 27.5 mmol), RM-2 (9.04 g, 25 mmol), palladium acetate (0.12 g, 0.5 mmol), 2-dicyclohexylphosphino-2',4',6'triisopropylbiphenyl (Xphos, 0.48 g, 1 mmol), potassium carbonate (6.91 g, 50 mmol), toluene (100 mL), tetrahydrofuran (25 mL), and deionized water (25 mL) were added sequentially to a 500 mL three-necked flask. The mixture was heated to reflux and stirred overnight. After the system cooled to room temperature, it was extracted with dichloromethane (100 mL × 3 times). The organic phases were combined and dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure to obtain a crude product. The crude product was purified by silica gel column chromatography using n-heptane / dichloromethane as the mobile phase to obtain a white solid (10.83 g, yield 73%, m / z = 594.20 [M+H] + ).

[0129] Referring to the synthesis of compound 4, reactant G shown in Table 6 was used instead of Sub-d1, and reactant H was used instead of RM-2 to synthesize the compounds of the present application in the following table.

[0130] Table 6

[0131] The NMR data of some compounds are shown in Table a below:

[0132] Table a

[0133] Example 1: Red organic electroluminescent device

[0134] First, the anode pretreatment is carried out through the following process: On the ITO / Ag / ITO substrate, the surface treatment is performed using ultraviolet ozone and O2:N2 plasma to increase the work function of the anode. The surface of the ITO substrate can also be cleaned with an organic solvent to remove impurities and oil stains on the surface of the ITO substrate.

[0135] On the experimental substrate (anode), PD:HT-1 was co-evaporated at an evaporation rate ratio of 2%:98% to form a thickness of Then HT-1 was vacuum evaporated on the hole injection layer to form a hole injection layer with a thickness of The first hole transport layer (HTL-1) is formed by vacuum evaporation of compound HT-2 to form a first hole transport layer with a thickness of The second hole transport layer (HTL-2) is formed.

[0136] Next, compound 4:RH-P:RD was co-evaporated on the second hole transport layer at an evaporation rate ratio of 49%:49%:2% to form a layer with a thickness of red light emitting layer (EML).

[0137] On the 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 mixed at a 1:9 evaporation rate and vacuum evaporated on the electron injection layer to form a layer with a thickness of cathode.

[0138] In addition, the thickness of the vacuum evaporation layer on the cathode is CP, thereby completing the manufacture of red organic electroluminescent devices.

[0139] Example 2-Example 64

[0140] An organic electroluminescent device was prepared by the same method as in Example 1, except that the compound shown in Table 7 below was used instead of Compound 4 in Example 1 when preparing the light-emitting layer.

[0141] Comparative Example 1-Comparative Example 5

[0142] An organic electroluminescent device was prepared using the same method as in Example 1, except that Compound A, Compound B, Compound C, Compound D, and Compound E were used to replace Compound 4 in Example 1 when preparing the light-emitting layer.

[0143] When preparing the organic electroluminescent device, the structures of the materials used in the comparative examples and the examples are as follows:

[0144] The performance of the red organic electroluminescent devices prepared in Examples 1-64 and Comparative Examples 1-4 was tested. Specifically, at 10 mA / cm 2 The IVL performance of the device was tested under the conditions of T 95 Device life at 20mA / cm 2 The test was carried out under the conditions of , and the test results are shown in Table 7.

[0145] Table 7

[0146] Referring to Table 7 above, it can be seen that when the compound of the present application is used as the host material of a red organic electroluminescent device, the efficiency is increased by at least 16.5% and the lifespan is increased by at least 12.2%. The structure of the compound of the present application contains a parent core structure of phenanthro[3,2-b]benzofuran, which is connected to an electron-deficient heteroaryl group of a triazine, as an electron-transporting red light host material. On the one hand, the special fusion method of phenanthro[3,2-b]benzofuran ensures that the parent core of phenanthro[3,2-b]benzofuran has a relatively suitable first excited triplet energy level, suitable as a fragment of a red light host material; on the other hand, the parent core structure of phenanthro[3,2-b]benzofuran has a large conjugated system. After connecting it to the electron-deficient heteroaryl group of a triazine, it can enhance the intermolecular force and improve the electron mobility of the compound. When the compound of the present application is used as an electron-transporting material in a hybrid red light host material, it can improve the carrier balance in the light-emitting layer, broaden the carrier recombination area, improve the exciton generation and utilization efficiency, and improve the device luminous efficiency and lifespan.

[0147] The preferred embodiments of the present invention are described in detail above. However, the present application is not limited to the specific details in the above embodiments. Within the technical concept of the present application, various simple modifications can be made to the technical solution of the present invention, and these simple modifications all fall within the scope of protection of the present invention.

Claims

1. An organic compound having a structure shown in Formula I: in, Each R is independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 12 carbon atoms; n is the number of R, and n is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; when n is greater than 1, any two R are the same or different; 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, and 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 Ar1, Ar2, L, L1 and L2 are the same or different and are independently selected from deuterium, a halogen group, a cyano 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 deuterated aryl group having 6 to 12 carbon atoms, an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 3 to 20 carbon atoms; optionally, any two adjacent substituents in Ar1 form a saturated or unsaturated 3-15 membered ring; optionally, any two adjacent substituents in Ar2 form a saturated or unsaturated 3-15 membered ring.

2. The organic compound according to claim 1, wherein Each R is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl or phenyl.

3. 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 arylene group having 6 to 18 carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 18 carbon atoms; Optionally, the substituents in L, L1 and L2 are each independently selected from deuterium, fluorine, cyano, an alkyl group having 1-4 carbon atoms, a haloalkyl group having 1-4 carbon atoms, a deuterated alkyl group having 1-4 carbon atoms, a trialkylsilyl group having 3-7 carbon atoms, an aryl group having 6-12 carbon atoms or a deuterated aryl group having 6-12 carbon atoms.

4. 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 phenanthrenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted pyridylene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, or a substituted or unsubstituted carbazolyl group; Optionally, the substituents in L, L1 and L2 are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trimethylsilyl, deuterated phenyl, phenyl or naphthyl.

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

6. The organic compound according to claim 1, wherein 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, or a substituted or unsubstituted heteroaryl group having 12 to 18 carbon atoms; Optionally, the substituents in Ar1 and Ar2 are the same or different and are independently selected from deuterium, fluorine, cyano, alkyl having 1-5 carbon atoms, haloalkyl having 1-5 carbon atoms, deuterated alkyl having 1-5 carbon atoms, trialkylsilyl having 3-7 carbon atoms, deuterated aryl having 6-12 carbon atoms, aryl having 6-12 carbon atoms, heteroaryl having 5-12 carbon atoms; optionally, any two adjacent substituents in Ar1 form a benzene ring or a fluorene ring; optionally, any two adjacent substituents in Ar2 form a benzene ring or a fluorene ring.

7. The organic compound according to claim 1, 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 phenanthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl; 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, trideuterated methyl, trimethylsilyl, pentadeuterated phenyl, phenyl, naphthyl, biphenyl, pyridyl, dibenzofuranyl, dibenzothiophenyl or carbazolyl.

8. The organic compound according to claim 1, wherein Ar1 and Ar2 are each independently selected from the group consisting of:

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

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

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