CN114075215A

CN114075215A - Organic compound, organic electroluminescent device comprising same, and electronic device

Info

Publication number: CN114075215A
Application number: CN202110647816.3A
Authority: CN
Inventors: 马天天; 杨敏; 杨雷
Original assignee: Material Science Co Ltd
Current assignee: Shaanxi Lighte Optoelectronics Material Co Ltd
Priority date: 2021-06-10
Filing date: 2021-06-10
Publication date: 2022-02-22
Anticipated expiration: 2041-06-10
Also published as: CN114075215B

Abstract

The application provides an organic compound, an organic electroluminescent device comprising the organic compound and an electronic device comprising the organic compound, and belongs to the field of organic electroluminescence. The structure of the organic compound is shown as a formula 1, and the organic compound is applied to an organic electroluminescent device, so that the performance of the organic electroluminescent device can be obviously improved.

Description

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

Technical Field

The application relates to the technical field of organic electroluminescence, in particular to an organic compound, an organic electroluminescent device comprising the organic compound and an electronic device comprising the organic compound.

Background

With the development of electronic technology and the progress of material science, the application range of electronic components for realizing electroluminescence or photoelectric conversion is more and more extensive. Such electronic components generally include a cathode and an anode that are oppositely disposed, 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 energy conversion layer, a hole transport layer between the energy conversion layer and the anode, and an electron transport layer between the energy conversion layer and the cathode.

Taking an organic electroluminescent device as an example, the organic electroluminescent device generally comprises an anode, a hole transport layer, an electroluminescent layer as an energy conversion layer, an electron transport layer and a cathode, which are sequentially stacked. When voltage is applied to the anode and the cathode, the two electrodes generate an electric field, electrons on the cathode side move to the electroluminescent layer under the action of the electric field, holes on the anode side also move to the luminescent layer, the electrons and the holes are combined in the electroluminescent layer to form excitons, and the excitons are in an excited state and release energy outwards, so that the electroluminescent layer emits light outwards.

At present, for a red organic electroluminescent device, the problems of reduced luminous efficiency, shortened service life and the like still exist, so that the performance of the device is reduced. Therefore, organic materials must solve these efficiency or lifetime problems, and there is a continuing need to develop new materials for organic light emitting devices that have high efficiency, long lifetime, and are suitable for mass production.

It is to be noted that the information disclosed in the above background section is only for enhancement of understanding of the background of the present application and therefore may include information that does not constitute prior art known to a person of ordinary skill in the art.

Disclosure of Invention

It is an object of the present invention to overcome the above-mentioned deficiencies in the prior art and to provide an organic compound, an organic electroluminescent device and an electronic apparatus including the same, which can improve the luminous efficiency and prolong the lifetime of the device.

In order to achieve the purpose of the invention, the following technical scheme is adopted in the application:

according to a first aspect of the present application, there is provided an organic compound having a structure represented by formula 1:

wherein X is selected from O or S;

L、L₁、L₂each 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;

L₃selected from substituted or unsubstituted arylene having 6 to 30 carbon atoms, substituted or unsubstituted heteroarylene having 3 to 30 carbon atoms;

Ar₁、Ar₂each group is independently selected from substituted or unsubstituted aryl with 6-40 carbon atoms and substituted or unsubstituted heteroaryl with 3-30 carbon atoms;

each R₁、R₂、R₃And R₄Each independently selected from deuterium, a halogen group, a cyano group, an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 5 to 20 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, and a cycloalkyl group having 3 to 10 carbon atoms;

n₁represents a substituent R₁Number of (2), n₁Selected from 0, 1,2, 3 or 4, when n is₁When greater than 1, any two R₁The same or different;

n₂represents a substituent R₂Number of (2), n₂Selected from 0, 1 or 2, when n₂When greater than 1, any two R₂The same or different;

n₃represents a substituent R₃Number of (2), n₃Selected from 0, 1 or 2, when n₃When greater than 1, any two R₃The same or different;

n₄represents a substituent R₄Number of (2), n₄Selected from 0, 1,2 or 3, when n is₄When greater than 1, any two R₄The same or different;

the L, L₁、L₂、L₃、Ar₁、Ar₂Wherein the substituents are independently selected from deuterium, a halogen group, a cyano group, a heteroaryl group having 3 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a substituted heteroaryl group having 3 to 20 carbon atoms, a substituted heteroaryl group having a halogen atom, a substituted heteroaryl group having 3 to 12 carbon atoms, a substituted heteroaryl group having 3 to 10 carbon atoms, a substituted heteroaryl group having 3 to 20 carbon atoms, a substituted heteroaryl group having 3 to 12 carbon atoms, a substituted heteroaryl group having 1 to 10 carbon atoms, a substituted heteroaryl group having a halogen atom, a substituted heteroaryl group having 3 to 20 carbon atoms, a substituted heteroaryl group having 3 to 12 carbon atoms, a substituted heteroaryl group having 1 to 10 carbon atoms, a substituted heteroaryl group having 3 to 10 carbon atoms, a halogen atom-substituted heteroaryl group, a substituted heteroaryl group having 1 to 10 carbon atom-substituted heteroaryl group, a halogen atom-substituted heteroaryl group, a substituted heteroaryl group, a substituted alkyl,Deuterated alkyl with 1-10 carbon atoms, triarylsilyl with 18-24 carbon atoms, cycloalkyl with 3-10 carbon atoms, heterocycloalkyl with 2-10 carbon atoms and alkoxy with 1-10 carbon atoms;

optionally, in Ar₁、Ar₂In (b), any two adjacent substituents form a ring.

The application uses a special carbazole fused ring derivative structure as a core, and combines with triarylamine, so that the molecule has high hole mobility, a proper T1 energy level (triplet state energy level) and a stable chemical structure. The organic compound is suitable for being used as a main body material of an organic electroluminescent device, and can improve the performance of the organic electroluminescent device.

According to a second aspect of the present application, there is provided an organic electroluminescent device comprising an anode, a cathode, and at least one functional layer interposed between the anode and the cathode, the functional layer comprising the organic compound described above.

According to a third aspect of the present application, there is provided an electronic apparatus comprising the above-described organic electroluminescent device.

It is to be understood that both the foregoing general description and the following detailed description are exemplary and explanatory only and are not restrictive of the application.

Drawings

The accompanying drawings, which are incorporated in and constitute a part of this specification, illustrate embodiments consistent with the present application and together with the description, serve to explain the principles of the application.

In the drawings:

fig. 1 is a schematic structural view of an organic electroluminescent device of the present application.

Fig. 2 is a schematic structural diagram of an electronic device according to an embodiment of the present application.

Description of the reference numerals

100. An anode; 200. a cathode; 300. a functional layer; 310. a hole injection layer; 321. a hole transport layer; 322. a hole assist layer; 330. an organic electroluminescent layer; 340. a hole blocking layer; 350. an electron transport layer; 360. an electron injection layer; 400. an electronic device.

With the above figures, there are shown specific embodiments of the present application, which will be described in more detail below. These drawings and written description are not intended to limit the scope of the inventive concepts in any manner, but rather to illustrate the inventive concepts to those skilled in the art by reference to specific embodiments.

Detailed Description

Example embodiments will now be described more fully with reference to the accompanying drawings. Example embodiments may, however, be embodied in many different forms and should not be construed as limited to the examples set forth herein; rather, these embodiments are provided so that this disclosure will be thorough and complete, and will fully convey the concept of example embodiments to those skilled in the art. The described features, structures, or characteristics may be combined in any suitable manner in one or more embodiments. In the following description, numerous specific details are provided to give a thorough understanding of embodiments of the application.

In the drawings, the thickness of regions and layers may be exaggerated for clarity. The same reference numerals denote the same or similar structures in the drawings, and thus detailed descriptions thereof will be omitted.

The described features, structures, or characteristics may be combined in any suitable manner in one or more embodiments. In the following description, numerous specific details are provided to give a thorough understanding of embodiments of the application. One skilled in the relevant art will recognize, however, that the subject matter of the present application can be practiced without one or more of the specific details, or with other methods, components, materials, and so forth. In other instances, well-known structures, materials, or operations are not shown or described in detail to avoid obscuring major technical ideas of the application.

The application provides an organic compound, the structural general formula of which is shown as formula 1:

wherein X is selected from O or S;

Ar₁、Ar₂each independently selected from substituted or unsubstituted aryl groups having 6 to 40 carbon atoms, and substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms;

the L, L₁、L₂、L₃、Ar₁、Ar₂Wherein the substituents are independently selected from deuterium, a halogen group, a cyano group, a heteroaryl group having 3 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having carbon atoms, and a halogen atom having carbon atoms1-10 deuterated alkyl, 18-24 carbon triarylsilyl, 3-10 carbon cycloalkyl, 2-10 carbon heterocycloalkyl, and 1-10 carbon alkoxy;

optionally, in Ar₁、Ar₂In (b), any two adjacent substituents form a ring.

In the present application, the description "independently selected" and "independently selected" are used interchangeably and should be understood in a broad sense, which means that the specific options expressed between the same symbols in different groups do not affect each other, or that the specific options expressed between the same symbols in the same groups do not affect each other. For example,') "

Wherein each q is independently 0, 1,2 or 3, each R "is independently selected from hydrogen, deuterium, fluoro, chloro" and has the meaning: the formula Q-1 represents that Q substituent groups R ' are arranged on a benzene ring, each R ' can be the same or different, and the options of each R ' are not influenced mutually; the formula Q-2 represents that each benzene ring of biphenyl has Q substituent groups R ', the number Q of the substituent groups R' on the two benzene rings can be the same or different, each R 'can be the same or different, and the options of each R' are not influenced with each other.

In the present application, the term "substituted or unsubstituted" means that a functional group described later in the term may or may not have a substituent (hereinafter, for convenience of description, the substituent is collectively referred to as Rc). For example, "substituted or unsubstituted aryl" refers to an aryl group or an unsubstituted aryl group having a substituent Rc. Wherein Rc as the substituent may be, for example, deuterium, a halogen group, a cyano group, a heteroaryl group having 3 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, 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 triarylsilyl group having 18 to 24 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a heterocycloalkyl group having 2 to 10 carbon atoms, or an alkoxy group having 1 to 10 carbon atoms.

In the present application, a "substituted" functional group may be substituted with one or 2 or more substituents in the above Rc; when two substituents Rc are attached to the same atom, these two substituents Rc may be independently present or attached to each other to form a ring with the atom; when two adjacent substituents Rc exist on a functional group, the adjacent two substituents Rc may exist independently or may form a ring fused with the functional group to which they are attached.

In this application, the terms "optional" and "optionally" mean that the subsequently described event can occur, but need not occur, and that the description includes instances where the event occurs or does not. For example, "optionally, two adjacent substituents x form a ring; "means that these two substituents may but need not form a ring, including: a case where two adjacent substituents form a ring and a case where two adjacent substituents do not form a ring.

In the present application, "any two adjacent substituents form a ring," any two adjacent "may include two substituents on the same atom, and may also include one substituent on each of two adjacent atoms; wherein, when two substituents are present on the same atom, the two substituents may form a saturated or unsaturated ring with the atom to which they are both attached; when two adjacent atoms have a substituent on each, the two substituents may be fused to form a ring. For example, when Ar₁When 2 or more substituents are present in the (A) group and any adjacent substituents form a ring, the resulting ring is a saturated or unsaturated ring having 5 to 13 carbon atoms, for example: fluorene rings, benzene rings, naphthalene rings, cyclopentane, cyclohexane, adamantane, and the like.

In this application, "optionally, at Ar₁、Ar₂Wherein any two adjacent substituents form a ring with each other "means that in Ar₁Or Ar₂In (3), any two adjacent substituents may or may not form a ring. For example, when Ar₁When two adjacent substituents form a ring, the carbon number of the ring is 5 to 13, and the ring may be saturated or unsaturated. For example: cyclohexaneAlkane, cyclopentane, adamantane, benzene ring, naphthalene ring, fluorene ring, etc., but are not limited thereto.

In the present application, the number of carbon atoms of the substituted or unsubstituted functional group means all the number of carbon atoms. For example, if L is selected from substituted arylene having 12 carbon atoms, then all of the carbon atoms of the arylene and the substituents thereon are 12. For example: ar is

The number of carbon atoms is 7; l is

The number of carbon atoms is 12.

In the present application, when a specific definition is not otherwise provided, "hetero" means that at least 1 hetero atom of B, N, O, S, P, Si or Se or the like is included in one functional group and the remaining atoms are carbon and hydrogen. An unsubstituted alkyl group can be a "saturated alkyl group" without any double or triple bonds.

In the present application, "alkyl" may include straight chain alkyl or branched alkyl. Alkyl groups may have 1 to 10 carbon atoms, and numerical ranges such as "1 to 10" refer herein to each integer in the given range; for example, "1 to 10 carbon atoms" refers to an alkyl group that may contain 1,2, 3,4, 5, 6, 7, 8, 9, or 10 carbon atoms. Further, the alkyl group may be substituted or unsubstituted.

Preferably, the alkyl group is selected from alkyl groups having 1 to 5 carbon atoms, and specific examples include, but are not limited to, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl and pentyl.

In the present application, cycloalkyl refers to a saturated hydrocarbon containing an alicyclic structure, including monocyclic and fused ring structures. Cycloalkyl groups may have 3-10 carbon atoms, a numerical range such as "3 to 10" refers to each integer in the given range; for example, "3 to 10 carbon atoms" refers to a cycloalkyl group that may contain 3 carbon atoms, 4 carbon atoms, 5 carbon atoms, 6 carbon atoms, 7 carbon atoms, 8 carbon atoms, 9 carbon atoms, or 10 carbon atoms. Cycloalkyl groups may be substituted or unsubstituted. Examples of cycloalkyl groups are cyclopentyl, cyclohexyl, adamantyl.

In this application, aryl refers to an optional functional group or substituent derived from an aromatic carbocyclic ring. The aryl group can be a monocyclic aryl group (e.g., phenyl) or a polycyclic aryl group, in other words, the aryl group can be a monocyclic aryl group, a fused ring aryl group, two or more monocyclic aryl groups joined by carbon-carbon bond conjugation, monocyclic aryl and fused ring aryl groups joined by carbon-carbon bond conjugation, two or more fused ring aryl groups joined by carbon-carbon bond conjugation. That is, unless otherwise specified, two or more aromatic groups conjugated through a carbon-carbon bond may also be considered as aryl groups herein. The fused ring aryl group may include, for example, a bicyclic fused aryl group (e.g., naphthyl group), a tricyclic fused aryl group (e.g., phenanthryl group, fluorenyl group, anthracyl group), and the like. The aryl group does not contain a hetero atom such as B, N, O, S, P, Se or Si. For example, biphenyl, terphenyl, and the like are aryl groups in this application. Examples of the aryl group may include, but are not limited to, phenyl, naphthyl, fluorenyl, anthracyl, phenanthryl, biphenyl, terphenyl, quaterphenyl, pentabiphenyl, triphenylene, pyrenyl, benzofluoranthenyl, phenanthrenyl, biphenyl, terphenyl, biphenyl, and the like,

And the like.

As used herein, a "substituted or unsubstituted aryl" group can contain from 6 to 40 carbon atoms, and in some embodiments the number of carbon atoms in a substituted or unsubstituted aryl group can be from 6 to 30, in some embodiments the number of carbon atoms in a substituted or unsubstituted aryl group can be from 6 to 25, in other embodiments the number of carbon atoms in a substituted or unsubstituted aryl group can be from 6 to 20, and in other embodiments the number of carbon atoms in a substituted or unsubstituted aryl group can be from 6 to 12. For example, in the present application, the number of carbon atoms of the substituted or unsubstituted aryl group may be 6, 12, 13, 14, 15, 18, 20, 24, 25, 28, 29, 30, 40, and of course, the number of carbon atoms may be other numbers, which are not listed here. In the present application, biphenyl is understood to mean phenyl-substituted aryl radicals and also unsubstituted aryl radicals.

In this application, reference to arylene is to a divalent group formed by an aryl group further deprived of a hydrogen atom.

In the present application, substituted aryl groups may be aryl groups in which one or two or more hydrogen atoms are substituted with groups such as deuterium atoms, halogen groups, cyano groups, aryl groups, heteroaryl groups, trialkylsilyl groups, alkyl groups, cycloalkyl groups, alkoxy groups, and the like. It is understood that the number of carbon atoms in a substituted aryl group refers to the total number of carbon atoms in the aryl group and the substituents on the aryl group, for example, a substituted aryl group having a carbon number of 18, refers to a total number of carbon atoms in the aryl group and its substituents of 18.

In the present application, as the aryl group as the substituent, specific examples include, but are not limited to: phenyl, naphthyl, anthracyl, phenanthryl, dimethylfluorenyl, biphenyl, and the like.

In the present application, heteroaryl refers to a monovalent aromatic ring containing 1,2, 3,4, or 5 heteroatoms in the ring, which may be at least one of B, O, N, P, Si, Se, and S, or derivatives thereof. The heteroaryl group may be a monocyclic heteroaryl group or a polycyclic heteroaryl group, in other words, the heteroaryl group may be a single aromatic ring system or a plurality of aromatic ring systems connected by carbon-carbon bonds in a conjugated manner, and any one of the aromatic ring systems is an aromatic monocyclic ring or an aromatic fused ring. Exemplary heteroaryl groups can include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thienothienyl, benzofuranyl, phenanthrolinyl, isoxazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, silafluorenyl, dibenzofuranyl, and N-arylcarbazolyl (e.g., N-phenylcarbazolyl), N-heteroarylcarbazolyl (e.g., N-pyridylcarbazolyl), N-alkylcarbazolyl (e.g., N-methylcarbazolyl), and the like, without limitation. Wherein, thienyl, furyl, phenanthroline group and the like are heteroaryl of a single aromatic ring system type, and the N-phenylcarbazolyl and the N-pyridylcarbazolyl are heteroaryl of a polycyclic system type connected by carbon-carbon bond conjugation.

As used herein, a "substituted or unsubstituted heteroaryl" group can contain from 3 to 30 carbon atoms, and in some embodiments the number of carbon atoms in the substituted or unsubstituted heteroaryl group can be from 12 to 24, in some embodiments the number of carbon atoms in the substituted or unsubstituted heteroaryl group can be from 12 to 20, in other embodiments the number of carbon atoms in the substituted or unsubstituted heteroaryl group can be from 12 to 18, and in other embodiments the number of carbon atoms in the substituted or unsubstituted heteroaryl group can be from 5 to 12. For example, the number of carbon atoms may be 3,4, 5, 7, 12, 13, 18, 20, 24, 25 or 30, and of course, other numbers may be used, which are not listed here.

In this application, a heteroarylene group refers to a divalent group formed by a heteroaryl group further lacking one hydrogen atom.

In the present application, substituted heteroaryl groups may be heteroaryl groups in which one or more hydrogen atoms are substituted with groups such as deuterium atoms, halogen groups, cyano groups, aryl groups, heteroaryl groups, trialkylsilyl groups, alkyl groups, cycloalkyl groups, alkoxy groups, and the like. It is understood that the number of carbon atoms in the substituted heteroaryl group refers to the total number of carbon atoms in the heteroaryl group and the substituent on the heteroaryl group.

In the present application, specific examples of the heteroaryl group as the substituent include, but are not limited to: pyridyl, carbazolyl, dibenzofuranyl, dibenzothienyl.

In the present application, the halogen group may include fluorine, iodine, bromine, chlorine, and the like.

In the present application, specific examples of the trialkylsilyl group having 3 to 12 carbon atoms include, but are not limited to, a trimethylsilyl group, a triethylsilyl group, and the like.

In the present application, specific examples of the haloalkyl group having 1 to 10 carbon atoms include, but are not limited to, a trifluoromethyl group.

As used herein, an delocalized linkage refers to a single bond extending from a ring system

It means that one end of the linkage may be attached to any position in the ring system through which the linkage extends, and the other end to the rest of the compound molecule.

For example, as shown in formula (f), naphthyl represented by formula (f) is connected to other positions of the molecule through two non-positioned bonds through the bicyclic ring, and the meaning of the naphthyl represented by the formula (f-1) includes any possible connection mode as shown in formula (f-10).

As another example, as shown in the following formula (X '), the dibenzofuranyl group represented by formula (X') is attached to another position of the molecule via an delocalized bond extending from the middle of the phenyl ring on one side, and the meaning thereof includes any of the possible attachment means as shown in the formulas (X '-1) -formula (X' -4).

The meaning of the connection or substitution is the same as that of the connection or substitution, and will not be described further.

In one embodiment of the present application, n₁，n₂，n₃，n₄Are all 0.

In one embodiment of the present application, L, L₁、L₂Each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroarylene group having 12 to 20 carbon atoms.

Optionally, said L, L₁、L₂Wherein the substituents are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, and an aryl group having 6 to 12 carbon atoms。

Specifically, the L, L₁、L₂Specific examples of the substituent in (1) include, but are not limited to: deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl.

In another embodiment of the present application, L, L₁、L₂Each independently selected from the group consisting of 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 phenanthrylene group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted dibenzothiophenylene group, and a substituted or unsubstituted carbazolyl group.

In a particular embodiment herein, L is selected from a single bond or phenylene.

Alternatively, L is selected from a single bond or the group consisting of:

in one specific embodiment of the present application, L₁、L₂Each independently selected from a single bond, a substituted or unsubstituted group V selected from the group consisting of:

wherein,

represents a chemical bond; the substituted group V has one or more substituents thereon, each of which is independently selected from deuterium, cyano, fluoro, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl; when the number of the substituents of V is more than 1, the substituents may be the same or different.

Alternatively, L₁、L₂Each independently selected from the group consisting of:

in one embodiment of the present application, L₃Is selected from substituted or unsubstituted arylene with 6-20 carbon atoms and substituted or unsubstituted heteroarylene with 12-20 carbon atoms.

Optionally, said L₃Wherein the substituents are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, and an aryl group having 6 to 12 carbon atoms.

Specifically, the L₃Specific examples of the substituent in (1) include, but are not limited to: deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl.

In another embodiment of the present application, L₃Each independently selected from the group consisting of substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted fluorenylene, substituted or unsubstituted dibenzofuranylene, substituted or unsubstituted dibenzothiophenylene, and substituted or unsubstituted carbazolyl.

In one specific embodiment of the present application, L₃Each independently selected from the group consisting of substituted or unsubstituted groups H, unsubstituted groups H selected from the group consisting of:

wherein,

represents a chemical bond; the substituted group H has one or more substituents thereon, each of which is independently selected from deuterium, cyano, fluoro, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl; when the number of substituents of H is more than 1, each substituent may be the same or different.

Optionally, said L₃Is selected from the group consisting of:

in one embodiment of the present application, Ar₁、Ar₂Each independently selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms and substituted or unsubstituted heteroaryl groups having 12 to 24 carbon atoms.

Optionally, the Ar is₁、Ar₂Wherein the substituents are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, a triphenylsilyl group, a trialkylsilyl group having 3 to 6 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, and a deuterated alkyl group having 1 to 5 carbon atoms.

Optionally, in Ar₁、Ar₂In which any two adjacent substituents form a saturated or unsaturated ring having 5 to 13 ring carbon atoms. For example, in Ar₁、Ar₂Wherein any two adjacent substituents form a cyclohexane, cyclopentane, adamantane, phenyl, naphthalene ring, or fluorene ring.

Specifically, Ar is₁、Ar₂Specific examples of the substituent in (1) include, but are not limited to: deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, adamantyl, triphenylsilyl, trimethylsilyl, trifluoromethyl, trideuteromethyl.

In another embodiment of the present application, Ar₁、Ar₂Each 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 2,3 benzofluorenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted anthryl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted anthryl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted anthrylOr unsubstituted dibenzothienyl.

Optionally, the Ar is₁、Ar₂Each substituent in (a) is independently selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, adamantyl, triphenylsilyl, trimethylsilyl, trifluoromethyl, trideuteromethyl;

optionally, in Ar₁、Ar₂Wherein any two adjacent substituents form a fluorene ring

In a specific embodiment of the present application, Ar is₁、Ar₂Each independently selected from substituted or unsubstituted groups W, wherein the unsubstituted groups W are selected from the group consisting of:

wherein,

represents a chemical bond; the substituted group W has one or more substituents thereon, each independently selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, adamantyl, triphenylsilyl, trimethylsilyl, trifluoromethyl, trideuteromethyl; when the number of substituents of W is more than 1, the substituents may be the same or different.

Alternatively, Ar₁、Ar₂Each independently selected from the group consisting of:

optionally, the organic compound is selected from the group consisting of:

the present application also provides an organic electroluminescent device comprising an anode and a cathode arranged opposite to each other, and at least one functional layer interposed between the anode and the cathode, the functional layer comprising the organic compound of the present application.

In one embodiment of the present application, the organic electroluminescent device is a red organic electroluminescent device.

In one embodiment, as shown in fig. 1, the organic electroluminescent device of the present application includes an anode 100, a cathode 200, and at least one functional layer 300 interposed between the anode layer and the cathode layer, wherein the functional layer 300 includes a hole injection layer 310, a hole transport layer 321, a hole auxiliary layer 322, an organic electroluminescent layer 330, an electron transport layer 350, and an electron injection layer 360.

Alternatively, a hole blocking layer 340 may be disposed between the organic electroluminescent layer 330 and the electron transport layer 350. The organic electroluminescent layer 330 may contain an organic compound as described in the first aspect of the present application.

Optionally, the anode 100 comprises an anode material, preferably a material with a large work function that facilitates hole injection into the functional layer. Specific examples of the anode material include metals such as nickel, platinum, vanadium, chromium, copper, zinc and gold or alloys thereof; metal oxides such as zinc oxide, Indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); combined metals and oxides, e.g. ZnO: Al or SnO₂Sb; or a conductive polymer such as poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene](PEDT), polypyrrole, and polyaniline, but are not limited thereto. Preferably, a transparent electrode including Indium Tin Oxide (ITO) as an anode is included.

Alternatively, the hole transport layer 321 may include one or more hole transport materials, and the hole transport material may be selected from carbazole multimer, carbazole-linked triarylamine-based compound, or other types of compounds, which are not specifically limited herein. For example, in one embodiment of the present application, hole transport layer 321 is comprised of HT-01.

Alternatively, the hole assist layer 322 may include one or more hole transport materials, and the hole transport materials may be selected from carbazole multimers, carbazole-linked triarylamine-based compounds, or other types of compounds, which are not specifically limited herein. For example, in one embodiment of the present application, the hole assist layer 322 is comprised of HT-02.

Alternatively, the organic electroluminescent layer 330 may be composed of a single light emitting material, and may include a host material and a guest material. Alternatively, the organic electroluminescent layer 330 may be composed of a host material and a guest material, and holes and electrons injected into the organic electroluminescent layer 330 may be combined in the organic electroluminescent layer 330 to form excitons, which transfer energy to the host material and transfer energy to the guest material, so that the guest material can emit light.

The guest material of the organic electroluminescent layer 330 may be a compound having a condensed aryl ring or a derivative thereof, a compound having a heteroaryl ring or a derivative thereof, an aromatic amine derivative, or other materials, which is not particularly limited in the present application.

In one embodiment of the present application, a red organic electroluminescent device, organic electroluminescent layer 330, comprises the organic compound described herein, RH-N and guest material Ir (piq)₂(acac)。

The electron transport layer 350 may have a single-layer structure or a multi-layer structure, and may include one or more electron transport materials, and the electron transport materials may be selected from benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials, which is not particularly limited in this application. For example, in one embodiment of the present application, electron transport layer 350 may be comprised of ET-01 and LiQ.

Alternatively, a hole blocking layer 340 is disposed on the organic electroluminescent layer 330 and the electron transport layer 350. The hole blocking layer may include one or more hole blocking materials, which are not particularly limited in this application.

Optionally, the cathode 200 comprises a cathode material, which is a material with a small work function that facilitates electron injection into the functional layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; or multi-layer materials such as LiF/Al, Liq/Al, LiO₂Al, LiF/Ca, LiF/Al and BaF₂But not limited thereto,/Ca. Preferably, a metal electrode comprising silver and magnesium is included as a cathode.

Optionally, a hole injection layer 310 may be further disposed between the anode 100 and the hole transport layer 320 to enhance the ability to inject holes into the hole transport layer 320. The hole injection layer 310 may be made of benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives, or other materials, which are not limited in this application. In one embodiment of the present application, the hole injection layer 310 may be composed of PtPC.

Optionally, an electron injection layer 360 may be further disposed between the cathode 200 and the electron transport layer 350 to enhance the ability to inject electrons into the electron transport layer 350. The electron injection layer 360 may include 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 360 may include ytterbium (Yb).

The application also provides an electronic device comprising the organic electroluminescent device.

For example, as shown in fig. 2, the electronic device provided in the present application is a first electronic device 400, and the first electronic device 400 includes any one of the organic electroluminescent devices described in the above embodiments of the organic electroluminescent device. The electronic device may be a display device, a lighting device, an optical communication device, or other types of electronic devices, which may include, but are not limited to, a computer screen, a mobile phone screen, a television, electronic paper, an emergency light, an optical module, and the like. Since the first electronic device 400 has the organic electroluminescent device, the same advantages are obtained, and the description of the present application is omitted.

The present application will be described in detail below with reference to examples, but the following description is intended to explain the present application, and not to limit the scope of the present application in any way.

Synthetic examples

One skilled in the art will recognize that the chemical reactions described herein may be used to suitably prepare a number of other compounds of the present application, and that other methods for preparing the compounds of the present application are considered to be within the scope of the present application. For example, the synthesis of those non-exemplified compounds according to the present application can be successfully accomplished by those skilled in the art by modification, such as appropriate protection of interfering groups, by the use of other known reagents other than those described herein, or by some routine modification of reaction conditions. In addition, the synthesis of the counter compounds disclosed herein.

Synthesis of intermediate a 1-1:

adding 12H-benzofuran [3,2-a ] carbazole (32.5 g; 126.2mmol), 2-chloro-3-fluoronitrobenzene (22.2; 126.2mmol), cesium carbonate (25.4 g; 126.2mmol) and dried DMSO (300mL) into a nitrogen-protected round-bottom flask, and heating to 100 ℃ under stirring for reaction for 20 hours; cooling the reaction mixture to room temperature, extracting the mixed solution by using toluene, collecting an organic phase, drying by using anhydrous magnesium sulfate, and removing the solvent under reduced pressure; the crude product was purified by column chromatography on silica gel using toluene/n-heptane as eluent to give intermediate a1-1(30.7 g; 59%)

Referring to the synthesis of intermediate a1-1, the intermediate compounds shown in the following table were synthesized using reactant a in table 1 below instead of 12H-benzofuran [3,2-a ] carbazole:

TABLE 1

Synthesis of intermediate a 1-2:

adding the intermediate a1-1(35.5 g; 86.0mmol), cesium carbonate (84.1 g; 258mmol) and DMAC (500mL) into a round-bottom flask, heating to 140 ℃ under the protection of nitrogen and stirring, dividing water for half an hour, then cooling to 80 ℃, adding tricyclohexylphosphine fluoborate (4.8 g; 12.9mmol) and palladium acetate (1.5 g; 6.9mmol), heating to 140 ℃ under stirring, and reacting for 16 hours; cooling the reaction mixture to room temperature, washing with water, separating the organic phase, drying over anhydrous magnesium sulfate, and removing the solvent under reduced pressure; the crude product was purified by column chromatography on silica gel using dichloromethane/n-heptane as eluent to give intermediate a1-2(17.2 g; 53%).

Referring to the synthesis of intermediate a1-2, intermediate compounds shown in table 2 below were synthesized using reactant C in table 2 below instead of intermediate a 1-1:

TABLE 2

Synthesis of intermediate a 1:

adding the intermediate a1-2(23.6 g; 62.7mmol), triphenylphosphine (41.1 g; 156.8mmol) and o-dichlorobenzene (250mL) into a flask, heating to 175 ℃ under the protection of nitrogen, and stirring for 36 hours; cooling to room temperature, washing the reaction solution with water, separating liquid, washing the organic phase with water, drying with anhydrous magnesium sulfate, and removing the solvent at high temperature under reduced pressure to obtain a crude product; the crude product was purified by column chromatography on silica gel using a dichloromethane/n-heptane system to give intermediate a1(15.1g, 70%) as a white solid.

Referring to the synthesis of intermediate a1, the intermediates shown in table 3 below were synthesized by substituting intermediate a1-2 with reactant D in table 3 below:

TABLE 3

Synthesis of SM-A-1:

adding the intermediate a1(5.0 g; 14.5mmol), p-bromoiodobenzene (4.9 g; 17.4mmol), tris (dibenzylideneacetone) dipalladium (0.27 g; 0.29mmol), tri-tert-butylphosphine (0.12 g; 0.58mmol), sodium tert-butoxide (2.09 g; 21.8mmol) and xylene (100mL) into a round-bottomed flask, and stirring at 135 ℃ for 16 hours under the protection of nitrogen; cooling to room temperature, washing the reaction liquid with water, separating liquid, drying an organic phase with anhydrous magnesium sulfate, and removing the solvent under reduced pressure to obtain a crude product; the crude product was purified by silica gel column chromatography using dichloromethane/n-heptane as eluent to give SM-A-1(3.6 g; 55%)

Referring to the synthesis of SM-a-1, the intermediate compounds shown in table 4 below were synthesized using reactant E instead of intermediate a1 and reactant F instead of p-bromoiodobenzene in table 4 below:

TABLE 4

Synthesis of SM-B-1:

into a reaction flask were charged 3-aminodibenzofuran (5g, 27.3mmol), SM1(8.4g, 27.3mmol), tris (dibenzylideneacetone) dipalladium (0.25g, 0.27mmol), 2-dicyclohexylphosphine-2 ', 4 ', 6 ' -triisopropylbiphenyl (0.26g, 0.55mmol), sodium tert-butoxide (3.9g, 41.9mmol) and toluene solvent (50mL), and the mixture was heated to 110 ℃ under nitrogen protection, refluxed and stirred for 8 hours. After the reaction solution was cooled to room temperature, the reaction solution was extracted and washed with dichloromethane (50mL) and water (50mL) 3 times, the organic layer was dried over anhydrous magnesium sulfate and filtered, after which the filtrate was passed through a short silica gel column, the solvent was removed under reduced pressure, and the crude product was purified by recrystallization using a dichloromethane/n-heptane system to give SM-B-1(7.1g, yield 63%).

Referring to the synthesis method of intermediate SM-B-1, intermediate compounds SM-B-X shown in table 5 below were synthesized using reactant W instead of 3-aminodibenzofuran and reactant Q instead of SM1 in table 5 below:

TABLE 5

Synthesis of Compound A-1:

into a reaction flask, SM-A-1(5g, 10.0mmol), diphenylamine (1.7g, 10.0mmol), tris (dibenzylideneacetone) dipalladium (0.09g, 0.1mmol), 2-dicyclohexylphosphine-2 ', 6' -dimethoxy-biphenyl (0.08g, 0.2mmol), sodium tert-butoxide (1.4g, 15.0mmol) and toluene solvent (100mL) were charged, heated to 110 ℃ under nitrogen protection, heated under reflux and stirred for 8 h. After the reaction solution was cooled to room temperature, the reaction solution was extracted and washed with dichloromethane and water 3 times, the organic layer was dried over anhydrous magnesium sulfate and filtered, and after filtration, the filtrate was passed through a short silica gel column, the solvent was removed under reduced pressure, and the crude product was purified by recrystallization using a dichloromethane/n-heptane system to give a1(4.1g, yield 70%).

Referring to the synthesis of compound a1, the compounds shown in table 6 below were synthesized using reactant X instead of SM-a-1 and reactant Y instead of diphenylamine in table 6 below:

TABLE 6

The mass spectra data of some compounds are shown in Table 7 below

TABLE 7

A1	m/z＝588.2[M+H]⁺	A3	m/z＝638.2[M+H]⁺
				A15	m/z＝714.3[M+H]⁺	A23	m/z＝738.3[M+H]⁺
A37	m/z＝714.3[M+H]⁺	A55	m/z＝829.3[M+H]⁺
				A63	m/z＝829.3[M+H]⁺	A69	m/z＝780.3[M+H]⁺
A78	m/z＝830.3[M+H]⁺	A85	m/z＝846.3[M+H]⁺
				A91	m/z＝756.2[M+H]⁺	B4	m/z＝664.2[M+H]⁺
B33	m/z＝878.3[M+H]⁺	B46	m/z＝866.3[M+H]⁺
				B75	m/z＝856.3[M+H]⁺	C4	m/z＝678.2[M+H]⁺
C19	m/z＝770.2[M+H]⁺	C42	m/z＝856.3[M+H]⁺
				D1	m/z＝638.2[M+H]⁺	D10	m/z＝688.3[M+H]⁺
D13	m/z＝664.2[M+H]⁺	D20	m/z＝780.3[M+H]⁺
				D41	m/z＝826.3[M+H]⁺	D42	m/z＝764.3[M+H]⁺
D43	m/z＝776.4[M+H]⁺	D44	m/z＝681.3[M+H]⁺
				D45	m/z＝846.3[M+H]⁺	D46	m/z＝782.2[M+H]⁺
D47	m/z＝804.3[M+H]⁺	A56	m/z＝816.3[M+H]⁺
				D38	m/z＝820.2[M+H]⁺	D48	m/z＝862.2[M+H]⁺
D49	m/z＝790.3[M+H]⁺

Part of the compound NMR data are shown in Table 8 below

TABLE 8

Preparation and performance evaluation of organic electroluminescent device

Example 1

Red organic electroluminescent device

Example 1

The thickness of ITO is set as

The substrate was cut into a size of 40mm x 0.7mm, and an experimental substrate having a cathode, an anode and an insulating layer pattern was prepared using a photolithography process using ultraviolet ozone and O₂:N₂The plasma performs a surface treatment to remove surface particles and increase the anode work function.

Vacuum evaporating PtPC on a substrate by PVD to form a thin film of

And depositing HT-01 on the hole injection layer to form a layer with a thickness of

The hole transport layer of (1).

The hole transport layer is vapor-deposited to a thickness of

HT-02, and a hole assist layer.

On the hole assist layer, compound a 1: the compound RH-N: ir (piq)₂(acac) at 49%: 49%: 2% (evaporation rate) of the mixture is subjected to co-evaporation to form

An organic electroluminescent layer (red light-emitting layer).

ET-01 and LiQ are mixed according to the weight ratio of 1:1 and evaporated to form

A thick electron transport layer formed by depositing Yb on the electron transport layer

Then the magnesium and silver are mixed in a ratio of 1: 10, vacuum evaporation on the electron injection layer

The cathode of (1).

Vapor deposition on the cathode

And forming an organic capping layer (CPL) with the thickness of CP-01 to complete the manufacture of the organic light-emitting device.

Examples 2 to 31:

in the formation of the red light-emitting layer, an organic electroluminescent device was produced in the same manner as in example 29, except that the compound shown in table 10 was used instead of the compound a1 in example 1.

Comparative example 1:

referring to table 10, organic electroluminescent devices were prepared in the same manner as in example 1, except that compound 1 was used instead of compound a1 in example 1.

Comparative example 2:

referring to table 10, organic electroluminescent devices were prepared in the same manner as in example 1, except that compound 2 was used instead of compound a1 in example 1.

In examples 2 to 31 and comparative examples 1 to 2, the structural formula of each material used is shown in the following Table 9:

TABLE 9

For the organic electroluminescent device prepared as above, at 20mA/cm²The IVL performance of the device is analyzed under the condition of (1), and the T95 life time is 15mA/cm²The results are shown in Table 10 below:

watch 10

As can be seen from table 10 above, when the compound in the present application is used as a hole-type host material in a red light dual host material, the current efficiency is improved by at least 13.5% and the lifetime is improved by at least 24.6% as compared to comparative examples 1-2.

When the compound in the present application is used as a hole-type host material in a red light dual host material, the device has improved efficiency and lifetime compared to comparative example 1; the reason for this is probably that the compound in the present application has higher hole mobility than compound 1, thereby improving the carrier recombination efficiency. Compared with comparative example 2, when the compound is used as an organic electroluminescent device, the service life of the device is obviously improved, and the reason for the improvement is probably that the parent molecular structure of the compound is more stable.

The application uses a special carbazole fused ring derivative structure as a core, and combines with triarylamine, so that the molecule has high hole mobility, a proper T1 energy level (triplet state energy level) and a stable chemical structure; the hole type host material is suitable for being used as a hole type host material in a red light dual-host material, so that a red light device has improved luminous efficiency and service life.

Other embodiments of the present application will be apparent to those skilled in the art from consideration of the specification and practice of the invention disclosed herein. This application is intended to cover any variations, uses, or adaptations of the invention following, in general, the principles of the application and including such departures from the present disclosure as come within known or customary practice within the art to which the invention pertains. It is intended that the specification and examples be considered as exemplary only, with a true scope and spirit of the application being indicated by the following claims.

Claims

1. An organic compound having a structure represented by formula 1:

wherein X is selected from O or S;

Ar₁、Ar₂each independently selected from substituted or unsubstituted aryl groups having 6 to 40 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms;

the L, L₁、L₂、L₃、Ar₁、Ar₂Wherein the substituents are independently selected from deuterium, halogen group, cyano, heteroaryl with 3-20 carbon atoms, aryl with 6-20 carbon atoms, trialkylsilyl with 3-12 carbon atoms, alkyl with 1-10 carbon atoms, haloalkyl with 1-10 carbon atoms, deuterated alkyl with 1-10 carbon atoms, triarylsilyl with 18-24 carbon atoms, cycloalkyl with 3-10 carbon atoms, heterocycloalkyl with 2-10 carbon atoms, and alkoxy with 1-10 carbon atoms;

optionally, in Ar₁、Ar₂In (b), any two adjacent substituents form a ring.

2. The organic compound of claim 1, wherein L, L₁、L₂Each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroarylene group having 12 to 20 carbon atoms;

optionally, said L, L₁、L₂Wherein the substituents are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, and an aryl group having 6 to 12 carbon atoms.

3. The organic compound of claim 1, wherein L, L₁、L₂Each independently selected from the group consisting of 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 dibenzofuranylene group, a substituted or unsubstituted dibenzothiophenylene group, and a substituted or unsubstituted carbazolyl group;

optionally, said L, L₁、L₂The substituents in (a) are each independently selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl.

4. The organic compound of claim 1, wherein L₁、L₂Each independently selected from a single bond, a substituted or unsubstituted group V selected from the group consisting of:

wherein,

5. The organic compound of claim 1, wherein L₃Selected from substituted or unsubstituted arylene group having 6 to 20 carbon atoms, substituted or unsubstituted arylene group having 12 to 20 carbon atomsA substituted heteroarylene group;

6. The organic compound of claim 1, wherein L₃Selected from the group consisting of substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted fluorenylene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl;

optionally, said L₃The substituents in (a) are each independently selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl.

7. The organic compound according to claim 1, wherein Ar is Ar₁、Ar₂Each independently selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 12 to 24 carbon atoms;

optionally, the Ar is₁、Ar₂Wherein the substituents are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, a triphenylsilyl group, a trialkylsilyl group having 3 to 6 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, and a deuterated alkyl group having 1 to 5 carbon atoms;

optionally, in Ar₁、Ar₂In which any two adjacent substituents form a saturated or unsaturated ring having 5 to 13 ring carbon atoms.

8. The organic compound according to claim 1, wherein Ar is Ar₁、Ar₂Each 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 naphthyl2,3 benzofluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted anthracyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl;

optionally, in Ar₁、Ar₂Wherein any two adjacent substituents form a fluorene ring.

9. The organic compound of claim 1, wherein the Ar is₁、Ar₂Each independently selected from substituted or unsubstituted groups W, wherein the unsubstituted groups W are selected from the group consisting of:

wherein,

10. The organic compound of claim 1, wherein n is₁，n₂，n₃，n₄Are all 0.

11. The organic compound of claim 1, wherein the organic compound is selected from the group consisting of:

12. an organic electroluminescent device comprising an anode, a cathode, and at least one functional layer interposed between the anode and the cathode, the functional layer comprising the organic compound according to any one of claims 1 to 11;

optionally, the functional layer comprises an organic electroluminescent layer comprising the organic compound;

optionally, the organic electroluminescent device is a red organic electroluminescent device.

13. An electronic device comprising the organic electroluminescent element according to claim 12.